CN101134744A - 杂环的化合物,其用途、有机半导体材料和电子或光电元件 - Google Patents
杂环的化合物,其用途、有机半导体材料和电子或光电元件 Download PDFInfo
- Publication number
- CN101134744A CN101134744A CNA2007100889082A CN200710088908A CN101134744A CN 101134744 A CN101134744 A CN 101134744A CN A2007100889082 A CNA2007100889082 A CN A2007100889082A CN 200710088908 A CN200710088908 A CN 200710088908A CN 101134744 A CN101134744 A CN 101134744A
- Authority
- CN
- China
- Prior art keywords
- diradical
- compounds
- doping agent
- dipolymer
- spiro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 56
- 239000004065 semiconductor Substances 0.000 title claims description 25
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000002019 doping agent Substances 0.000 claims description 45
- -1 heterocyclic radicals Chemical class 0.000 claims description 42
- 150000003413 spiro compounds Chemical class 0.000 claims description 24
- 238000002156 mixing Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- 125000005266 diarylamine group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000005427 anthranyl group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical compound S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 claims 1
- 239000007772 electrode material Substances 0.000 claims 1
- 230000005669 field effect Effects 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Natural products O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 150000004867 thiadiazoles Chemical class 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000005000 thioaryl group Chemical group 0.000 claims 1
- 125000005296 thioaryloxy group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 5
- 239000000539 dimer Substances 0.000 abstract 1
- 230000005693 optoelectronics Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- 150000003254 radicals Chemical class 0.000 description 21
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 20
- 239000010410 layer Substances 0.000 description 18
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 14
- 238000000151 deposition Methods 0.000 description 13
- 230000008021 deposition Effects 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- 238000005406 washing Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000001291 vacuum drying Methods 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000005670 electromagnetic radiation Effects 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000002427 irreversible effect Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052728 basic metal Inorganic materials 0.000 description 3
- 150000003818 basic metals Chemical class 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical group NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- GTZCNONABJSHNM-UHFFFAOYSA-N 5,10,15,20-tetraphenyl-21,23-dihydroporphyrin zinc Chemical compound [Zn].c1cc2nc1c(-c1ccccc1)c1ccc([nH]1)c(-c1ccccc1)c1ccc(n1)c(-c1ccccc1)c1ccc([nH]1)c2-c1ccccc1 GTZCNONABJSHNM-UHFFFAOYSA-N 0.000 description 1
- DGWSNUKQRDJSLY-UHFFFAOYSA-N C(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC.[Zn] Chemical compound C(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC.[Zn] DGWSNUKQRDJSLY-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 229910001268 Ferrocerium Inorganic materials 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- FLNKWZNWHZDGRT-UHFFFAOYSA-N azane;dihydrochloride Chemical compound [NH4+].[NH4+].[Cl-].[Cl-] FLNKWZNWHZDGRT-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920003240 metallophthalocyanine polymer Polymers 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- GDJYIXGPYCKDOV-UHFFFAOYSA-N n-phenylthiohydroxylamine Chemical group SNC1=CC=CC=C1 GDJYIXGPYCKDOV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/611—Charge transfer complexes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hybrid Cells (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Physical Vapour Deposition (AREA)
Abstract
本发明涉及杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,涉及有机半导体材料和电子和光电元件。
Description
本发明涉及杂环的自由基或双自由基、其二聚物、低聚物、聚合物、二螺化合物和多环,其用途、有机半导体材料和电子或光电元件。
已知通过掺杂来调节有机半导体的电学性质,尤其是它们的导电性,对于无机半导体例如硅半导体亦然。在此,起初非常低的导电性通过在基体材料中产生载荷子而得以提高,并且取决于所用的掺杂剂类型,还可以实现半导体的Fermi级的改变。在这种情况下掺杂导致电荷传递层的传导率提高,由此欧姆损耗减少,接触物和有机层之间载荷子的传递提高。
目前所用的无机掺杂剂,例如碱金属或碱土金属(例如铯)或Lewis酸(例如FeCl3),由于其高的扩散系数,在有机基体材料的情形下通常是不利的,因为电子元件的功能和稳定性被损坏。这些无机掺杂剂还有生产困难的问题,因为它们在室温下通常具有高的蒸气压,可能在真空工艺中污染生产系统。由于其对空气的高反应性,碱金属或碱土金属的使用更加因难,因此其也就更为不利。也已知通过化学反应在半导体基体材料中释放掺杂剂以提供掺杂剂。但是以这种方式释放的掺杂剂的氧化电势通常不足以用于各种应用,例如尤其是有机发光二极管(OLEDs)。而且,当释放掺杂剂时,也产生了其他化合物和/或原子,例如原子氢,从而使掺杂层和相应的电子元件的性质遭到破坏。
此外,用作掺杂剂的化合物对于相应的应用而言通常不具有足够低的电离势。
本发明的目的是提供新型化合物,其可用作n型掺杂剂,用作注入层或用作阻挡层,其中所述化合物还具有足够低的氧化电势用于生产有机发光二极管的电子传递材料,而不会对基体材料有任何破坏性影响,和意欲提供基体材料中载荷子数量的有效增加并且相对容易处理。
本发明的其他目的包括指明这些化合物可能的用途,提供有机半导体材料和其中可以使用所述化合物的电子元件或光电元件,例如光引发存储器。
第一个目的通过权利要求1给出的杂环的自由基或双自由基、其二聚物、低聚物、聚合物、二螺化合物和多环而实现。其他目的通过其他独立权利要求的内容而实现,优选的实施方式在从属权利要求中给出。
更优选具有下列结构的化合物:
结构5e-5o和3h中的R0,R1-R12可从权利要求1中对于R’s的定义中选择。
另外,优选结构5c,其中R1-R16=H或R1,R4-R16=H和R2,R3=CH3。
另外,一种特别优选的化合物是基于结构1a,其中Y=NR21,其中R21=烷基,优选甲基;其中R0,R21=烷基,优选甲基;R1,R2=芳基,尤其是苯基、甲苯基、二甲苯基、茴香基、噻吩基、呋喃基、烷基,尤其是环己基、环戊基、正烷基;或混合变体,其中R1=烷基,尤其是甲基、乙基、丙基,和R2=芳基,尤其是苯基、甲苯基、二甲苯基、茴香基、噻吩基、呋喃基。
在本发明中,术语“二聚物”应理解为通过使两个单自由基或双自由基彼此反应而产生的化合物。
术语“低聚物”应理解为由多个双自由基组成的化合物,其中一个双自由基的第一自由基末端与其他双自由基的第一末端反应,新形成的较大双自由基的第二末端接着与第二其他双自由基反应。这种低聚物的末端可与单自由基反应。
术语“聚合物”应理解为,与低聚物相比,由较大量的双自由基组成的化合物。
根据本发明,“二螺化合物”是双自由基的分子内加成产物,其基团中心由结构单元隔开,该结构单元的类型使得所述结构单元连接载带自由基的碳原子(即彼此反应的碳原子)。
术语“多环”应理解为双自由基的分子内加成产物,其基团中心由结构单元隔开,该结构单元的类型使得所述结构单元连接除载带自由基的碳原子外的至少一个碳原子(例如,至少一个α-位的原子)。
R0-19,R21,R22和R23可优选为取代芳基,其中取代基优选为给电子基团,例如二烷基胺、julolidyl、二芳基胺、烷基芳基氨基、二杂环基胺、二杂烷基胺、烷氧基、芳氧基、烷基巯基、芳基巯基、烷基、甲硅烷基(sililyl)、卤代烷基、环烷基、卤代环烷基、烯基、炔基、三烷基甲硅烷基炔基或苯乙烯基。
所有要求保护的化合物可以是全氟化的或部分氟化的,特别是饱和的桥或柄。
出人意料地发现,如果自由基和双自由基、其二聚物、低聚物、聚合物、二螺化合物和多环以中性形式用作有机半导体基体材料的n型掺杂剂,则得到比从前已知的给体化合物更强和/或更稳定的掺杂剂。特别地,当根据本发明将所述化合物用作n型掺杂剂时,在诸如电子元件等的应用中,电荷传递层的传导率可显著提高,和/或接触物和有机层之间载荷子的传递可以显著提高。本发明的化合物本身也可用作传递材料。因此,在蒸气沉积过程中为产生有机半导体材料,例如自由基(或二聚物)与常规基体材料之间的浓度比可以是10∶1。
不欲被其所限制,认为根据本发明,当所公开的杂环化合物用于掺杂层时,尤其通过从相应的杂环的自由基或双自由基、其二聚物、低聚物、二螺化合物或多环传递至少一个电子到周围的基体材料,而形成与相应的杂环的自由基和双自由基相关的阳离子。在此过程中,也形成基体材料的阴离子,其可以在基体材料上移动。以这种方式,基体材料得到了比未掺杂基体材料更高的传导率。未掺杂基体材料的传导率通常<10-8S/cm,特别地通常<10-10S/cm。应确保基体材料具有足够高的纯度。可用常规方法例如梯度升华来获得这种纯度。通过掺杂,该基体材料的传导率可提高至大于10-8S/cm,通常>10-6S/cm。这尤其适用于还原电势小于-1V vs.Fc/Fc+,优选小于-1.7V vs.Fc/Fc+,特别小于-2.1V vs.Fc/Fc+的基体材料。符号Fc/Fc+涉及氧化还原对二茂铁/铁铈齐(ferrocenium),其在电化学电势确定例如循环伏安法中用作参照。
在本申请中,掺杂剂一方面理解为混入的材料(“该层用掺杂剂掺杂”)。另一方面,掺杂剂可以是氧化还原活性物质,其导致电荷传递传导率(“该掺杂剂导致n型掺杂”)。认为二聚物等是所述第一类型的掺杂剂,而相应的自由基则是第二类型的掺杂剂。
根据本发明还发现,所述杂环的自由基或双自由基和其衍生物可用作电子元件中的注入层,优选在电极和半导体层之间,其也可以是掺杂的,或用作阻挡层,优选在发光层和传递层之间,或用作电子元件中的半导体层。还发现通过本发明的化合物,有机半导体的光引发(photo-induced)或光引发(light-induced)的不可逆掺杂是可能的,特别是通过电磁辐射裂解它们的二聚物或低聚物或二螺化合物并随后进行n型传导半导体的不可逆掺杂来产生所述的自由基和双自由基。
也可使用本发明的化合物作为食品工业、制药业中的自由基清除剂或抗氧化剂,用于消防或用作杀虫剂,特别用作杀昆虫剂、除草剂、杀真菌剂等等。也可用作自由基反应中的自由基引发剂(优选自由基引发的聚合或活性自由基聚合)。最后,应指出三重态双自由基也可在有机电子和光电元件中以存储器或开关结构的形式用作磁性化合物。
回到本发明的杂环的自由基、双自由基和其衍生物作为掺杂剂的优选用途,可例如通过下列三种机理以光引发的方式进行掺杂:
1.所述二聚物/低聚物/聚合物/二螺化合物或多环本身吸收适当波长的电磁辐射,从而裂解为掺杂自由基或双自由基。电子从自由基/双自由基的HOMO转移到基体材料的LUMO。
2.通过暴露于电磁辐射激发基体材料,从而电子从掺杂剂(二聚物/低聚物/聚合物/二螺化合物/多环)的HOMO转移到前一HOMO,该HOMO现在是单电子占据的(single occupied)。该掺杂剂然后进行不可逆反应。
3.光化学激发掺杂剂(二聚物/低聚物/聚合物/二螺化合物/多环),然后电子从掺杂剂的单电子占据的LUMO转移到基体材料的LUMO。该掺杂剂然后进行不可逆反应。
但是,各种机理同时发生也是可能的,最终可能通过此处未提及的机理而实现电子转移,例如通过键的热裂解。然而,一旦电磁辐射被关掉,全部的或部分的传导率被不可逆地和永久地保留。
现在基于下列实施例描述本发明的化合物的其他目的和优点,这些实施例仅是说明性的,不是用来限制本发明的范围。
本发明的掺杂剂就其与大气的反应性而言具有出人意料的高稳定性。
合成方法
可通过已知方法合成本发明的自由基、双自由基和其衍生物。应理解所引用的文献只是以例子的方式提及。
对于所有所述的化合物,以苯并咪唑为例未意性的显示获得自由基/双自由基的完整路径。
苯并咪唑c尤其可由邻苯二胺a和适当的羧酸衍生物(M.R.DeLuca,S.M.Kerwin Tetrahedron 1997,53 457-64)可醛类(M.Curini etal.Synlett 2004,10,1832-4)容易地合成。还参见:M.R.Grimmett“Imidazole and Benzimidazole Synthesis”Academic Press;Harcourt Brace& Company,Publishers,London,San Diego,New York,Boston。邻苯二胺是可商购的或可例如通过Suschitsky et al.的方法得到(J.Chem.Soc.Chem.Comm.1977,189-90)。苯并噻衍生物或嗯唑衍生物可通过邻巯基苯胺或邻羟基苯胺以相同的方式获得。在碱的存在下用硫酸二甲酯或硫酸二乙酯(H.Quast,E.Schmitt Chem.Ber.1968,101,4012-14)或用烷基卤化物进行五元杂环c中N原子的烷基化。相应的阳离子产物(杂芳端)d可以中性形式分离,例如作为高氯酸盐、四氟硼酸盐、卤化物、四苯基硼酸盐或六氟磷酸盐或与其他适当的反离子。
所述自由基可以通过碱金属化学制备,或通过还原反应由相应的杂芳阳离子电化学或光化学制备(T.Muramatsu et al.Chemistry Letters1996,151-2;Pragst et al.J.Electroanal.Chem.1984,180,141-56,J.Heinze.H.,Ber.Bunsenges.1972 76/294)。
但是,所述自由基通常进一步快速反应形成二聚物f、低聚物、聚合物、二螺化合物i或多环(三环)l。可通过ESR光谱法检测到所述自由基作为中间阶段发生这一事实。
双-[3-甲基-2-烷基-1,2-二氢苯并噻唑基-(2)]和双-[3-甲基-2-芳基-1,2-二氢苯并噻唑基-(2)]化合物可通过苯并噻唑鎓盐和适当的Grignard化合物直接得到(A.Kinya;S,Hiroaki;I.Naoki;Bull.Chem.Soc.Japan 1979 52/1,156-9)。
二螺化合物I可由2,2’-桥接苯并咪唑形成。
获得N-取代的杂芳阳离子
实施例1:
2-甲基巯基-1,3-二甲基苯并咪唑鎓高氯酸盐
在70ml水中悬浮0.1mol的2-巯基苯并咪唑。加入0.3mol的NaHCO3和0.5mol的硫酸二甲酯并在室温下搅拌过夜。向澄清溶液中逐滴加入12ml50%四氟硼酸,冷却并通过抽吸沉淀,从1,2-二氯乙烷中重结晶。
Fp.=160-3℃
实施例2:
2-哌啶基-1,3-二甲基苯并咪唑鎓高氯酸盐
将0.01mol的2-甲基巯基-1,3-二甲基苯并咪唑鎓高氯酸盐与0.01mol的哌啶在250ml二噁烷中回流加热4h。通过抽吸除去固体并从乙醇中重结晶。
Fp.179℃
实施例3:
2-二甲基氨基苯并咪唑鎓氯化物
在室温下在100ml二噁烷中搅拌0.05mol的邻苯二铵二氯化物和0.05mol的二氯亚甲基-N,N-二甲基亚铵氯化物2.5-3h,通过抽吸除去固体并用两者之一洗涤。从乙醇中重结晶。
Fp.293℃
实施例4:
1,4-双-1’,1”,3’,3”-四甲基苯并咪唑鎓-2’,2”-丁烷
在30ml由50%的水和50%的乙二醇单甲基醚组成的混合物中悬浮0.01mol的1,4-二苯并咪唑基-2’,2”-丁烷,加入0.06mol的碳酸氢钠和0.05mol的硫酸二甲酯并在室温下搅拌过夜。然后用10mol的浓高氯酸过滤并沉淀。
实施例5:
2,3,5,6-四氢-1H,4H-3a,10b-二氮杂-6a-氮鎓荧蒽
在205ml的DMF中于120℃加热0.1mol的2-氨基苯并咪唑与0.2mol的1,3-二溴丙烷和0.3mol的KCO3 8h。通过抽吸除去固体,充分浓缩溶剂,吸收甲醇,然后加入70%高氯酸。用甲醇、水并再用甲醇洗涤沉淀的白色晶体。
Fp.:242℃
实施例6:
2-异丙基-1,3-二甲基苯并咪唑鎓高氯酸盐
在70ml水中悬浮0.1mol的2-巯基苯并咪唑。加入0.3mol的NaHCO3和0.5mol的硫酸二甲酯并在室温下搅拌过夜。向澄清溶液中逐滴加入10ml 70%高氯酸,冷却并通过抽吸沉淀,从乙醇中重结晶。
Fp.=346℃
实施例7:
双-(N,N’,2,2’-四甲基-1H-苯并咪唑鎓)-1,3-丙烷二碘化物
在20ml二甲氧基乙烷中在氩气下悬浮0.02mol的NaH,在冰冷却下加入0.02mol的2-甲基苯并咪唑。气体发散结束后,在室温下继续搅拌60min,逐滴加入0.01mol的1,3-二溴丙烷并搅拌10min。在水浴中于60℃加热反应混合物4.5h,在室温下搅拌过夜,倾倒到冰/水上。通过抽吸除去沉淀的粗产物并真空干燥。将0.005mol的该中间产物置于30ml水中,加入0.015mol的NaHCO3和0.015mol的硫酸二甲酯,搅拌过夜并用1-2ml的浓盐酸沉淀。
Fp.:分解>306℃
实施例8:
1,2,3,5,6,7-六甲基苯并-1,7-二氢苯并[1,2-d,4,5-d’]二咪唑鎓二高氯酸盐
在约40-50ml水中悬浮0.013mol的2,6-二甲基苯并-1,7-二氢苯并[1,2-d,4,5-d’]二咪唑,加入0.078mol的NaHCO3和0.064mol的硫酸二甲酯。在室温下搅拌12h,逐滴加入4-5ml的70%高氯酸。通过抽吸除去白色沉淀,用乙醇、水并再用乙醇洗涤。
Fp.:>350℃
获得自由基、双自由基,和其二聚物、低聚物以及二螺化合物或多环
实施例a:
双-[1,3-二甲基-2-N-哌啶基-1,2-二氢苯并咪唑基-(2)]
在THF中回流加热0.01mol的2-N-哌啶基-1,3-二甲基苯并咪唑鎓四氟硼酸盐和钾,过滤,浓缩并冷却。通过抽吸除去沉淀晶体并用冷乙腈洗涤。
Fp:195℃
实施例b:
双-[1,3-二甲基-2-异丙基-1,2-二氢苯并咪唑基-(2)]
将1,3-二甲基-2-异丙基苯并咪唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐在乙腈中的溶液中,并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:146℃
实施例c:
双-[1,3-二甲基-2-N-哌啶基-1,2-二氢苯并咪唑基-(2)]
将1,3-二甲基-2-N-哌啶基苯并咪唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐/DMF中,并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:120℃
实施例d:
双-[1,3,5,6-四甲基-2-异丙基-1,2-二氢苯并咪唑基-(2)]
在THF中回流加热0.01mol的1,3,5,6-四甲基-2-异丙基苯并咪唑鎓四氟硼酸盐和钾,过滤,浓缩并冷却。通过抽吸除去沉淀晶体并用冷乙腈洗涤。
或者
将1,3,5,6-四甲基-2-异丙基苯并咪唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐/DMF中,并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:129-30℃
实施例e:
2-异丙基-1,3-二甲基-2,3,6,7-四氢-1H-5,8-二氧杂-1,3-二氮杂环五[b]萘
溶解0.1M的四丁基铵高氯酸盐/乙腈,并在-2.4V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:142℃
实施例f:
1,2,3,5,6,7-六甲基苯并-1,7-二氢苯并[1,2-d,4,5-d’]二咪唑基-(2)低聚双自由基
将0.01mol的1,2,3,5,6,7-六甲基苯并-1,7-二氢苯并[1,2-d,4,5-d’]二咪唑鎓二高氯酸盐溶解在0.1M的四丁基铵高氯酸盐/DMF中,并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:>250℃
实施例g:
双-[1,3-二甲基-2-异丙基-1,2,4,5,6,7-六氢苯并咪唑基-(2)]
将1,3-二甲基-2-异丙基-4,5,6,7-四氢苯并咪唑鎓六氟磷酸盐溶于0.1M的四丁基铵六氟磷酸盐在DMF中的溶液中,并在-2.6V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:127-9℃
实施例h:
双-[4,5-二苯基-2-异丙基-1,2-二氢咪唑基-(2)]
将4,5-二苯基-2-异丙基咪唑鎓六氟磷酸盐溶于0.1M的四丁基铵六氟磷酸盐在DMF中的溶液中,并在-2.45V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:160-3℃
实施例i:
双-[3-苯基-2-异丙基-1,2-二氢苯并噻唑基-(2)]
将3-苯基-2-异丙基苯并噻唑鎓高氯酸盐溶于0.1M的四丁基铵高氯酸盐在乙腈中的溶液中,并在-2.3V下在三室电解槽中利用汞电极沉淀。通过抽吸除去所述白色沉淀,用乙腈洗涤并真空干燥。
Fp:146℃
基体材料
作为n型掺杂(n-dopable)基体材料,可以使用喹啉络合物,例如铝或其他主族金属,其中所述的喹啉配体也可以被取代。特别地,所述基体材料可以是三(8-羟基喹啉)合铝。还可以任选使用其他带有O和/或N供电子原子的铝络合物。常见的基体材料还有酞菁锌(ZnPc)或四苯基卟啉锌(ZnTPP),仅列出几个酞菁或卟啉络合物的例子。
tris(8-hdroxy-quinolinato)-aluminium BPhen=bathophenanthroline
(4,7-Diphenyl-1,10-phenanthroline)
C24H16N2
B is-(2-m ethyl-8-quinolinolato)-4-(phenyl-phenolato)-aluminium-(III)
所述的喹啉络合物可含有例如一个、两个或三个喹啉配位体,其中另外的配位体优选与O和/或N供电子原子络合到中心原子上,如例如上述的Al络合物。
作为基体材料,还可使用菲咯啉,其可是取代或未取代的,特别是芳基取代的。例如苯基或萘基取代的。特别的,可使用Bphen作为基体材料。
作为基体材料,还可使用杂原子,例如特别是三唑,还可以是吡咯,咪唑,三唑,吡啶,嘧啶,哒嗪,喹喔啉,吡嗪并喹喔啉等。所述杂原子优选被取代,特别是芳基取代,例如苯基或萘基取代的。特别的,可使用下面的三唑作为基体材料。其他的基体材料例如可见A.P.Kulkarni et al.,Chem.Mater.16,4556ff.(2004)。
3-(4-B iphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole
C 30H 27N 3
所用的基体材料优选完全由金属酞青络合物组成,特别是ZnPc,卟啉络合物,或巴克明斯特·富勒烯,特别是C60富勒烯。
应理解为在本发明的范围内,所述的基体材料还可以用作彼此或与其他材料的混合物。应理解为还可使用适当的具有半导体特性的其他有机基体材料。
掺杂方法
在掺杂工艺中,作为开环的结果,所述的聚合、低聚或二聚化合物或二螺化合物分解得到实际的掺杂自由基。所述聚合物、低聚物和二聚物和二螺化合物的分解还可以在所述混合层的制备之前、其间或之后,以光引发方式进行,并从而将所述半导体层暴露于电磁辐射之下,优选在紫外和/或可见光下,有利地在所述混合汽相淀积(混合物由掺杂剂和基体组成)之前、其间或之后发生。此外,在所述汽相淀积过程中受热可引起所述聚合物、低聚物和二聚物或二螺化合物裂解成具有掺杂性质的自由基。对于某些应用,在生产其间或之后加热所述混合层也是有利的。
用本发明化合物对各基体材料的掺杂可以通过以下方法的一种或组合进行。
a)在真空中用一种用于基体材料和一种用于掺杂剂的源进行混合汽相淀积。
b)依次将所述基体材料和n型掺杂剂沉淀到基材上,随后所述掺杂剂向内扩散,特别是通过热处理。
c)用n型掺杂剂溶液掺杂基体层,随后蒸发溶剂、特别是通过热处理。
d)通过应用到表面上的掺杂剂层而表面掺杂基体材料层。
e)制备基体分子和掺杂剂的溶液,然后通过常规方法,例如溶剂蒸发或旋涂制备一层由该溶液组成的层。
所述掺杂还可以这样进行,即将掺杂剂从前体化合物中蒸发出来,其在加热和/或受辐射时释放出掺杂剂。所述前体化合物可使用例如,羰基化合物,二氮化合物或类似的在释放掺杂剂时释放出CO、氮等的物质,其中还可使用其他适当的前体,例如盐,如卤化物,氢化化合物等。可通过电磁辐射,尤其是可见光、UV光或IR光进行辐射照射,例如激光,或者通过其他类型的辐射。所述辐射照射可基本通过蒸发所需的热,并还可能以靶向方式将辐射引入所述待蒸发的化合物或前体或络合物化合物一例如电荷转移络合物一的特定波段, 以通过分离所述络合物促进所述化合物的蒸发,例如通过将它们转移到激发态。然而,所述络合物还可特别是足够稳定的以蒸发而无离解,或者在给定条件下被应用到所述基材上。应理解还可使用其他适当的方法进行所述掺杂。
这样,根据本发明,从而可以制得有机半导体的n型掺杂层,其可以多种方式使用。
掺杂使用实施例
提供了本发明自由基或其低聚物,优选二聚物,和双自由基或二螺化合物和其三环。
实施例 I:
与基体材料酞菁锌ZnPc一起使用中性二聚物双-[1,3-二乙基-2-甲基-1,2-二氢苯并咪唑基-(2)]。以ZnPc作为基体材料,通过基体和掺杂剂的混合汽相淀积制备掺杂比为掺杂剂:基体材料为1∶20的掺杂层。这里的传导率为3×10-4S/cm。
实施例II:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3-二甲基-2-异丙基-1,2-二氢苯并咪唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为10-3S/cm。
实施例III:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3-二甲基-2-异丙基-1,2-二氢苯并咪唑基-(2)]和ZnTTP的混合汽相淀积。得到的传导率为10-8S/cm。
实施例IV:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3-二甲基-2-乙基-1,2-二氢苯并咪唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为10-4S/cm。
实施例V:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3-二甲基-2-N-吡咯烷基-1,2-二氢苯并咪唑-(2)]和ZnTPP的混合汽相淀积。得到的传导率为10-4S/cm。
实施例VI:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3,5,6-四甲基-2-异丙基-1,2-二氢苯并咪唑基-(2)]和八乙基卟啉锌ZnOEP的混合汽相淀积。得到的传导率为5×10-8S/cm。
实施例VII:
以与实施例I类似的方式,以在实施例I中给出的比例进行2-异丙基-1,3-二甲基-2,3,6,7-四氢-1H-5,8-二氧杂-1,3-二氮杂环五[b]萘和ZnTPP的混合汽相淀积。得到的传导率为1.8×10-4S/cm。
实施例VIII:
以与实施例I类似的方式,以在实施例I中给出的比例进行2-异丙基-1,3-二甲基-2,3,6,7-四氢-1H-5,8-二氧杂-1,3-二氮杂环五[b]萘和ZnOEP的混合汽相淀积。得到的传导率为5×10-8S/cm。
实施例IX:
以与实施例I类似的方式,以在实施例I中给出的比例进行2-异丙基-1,3-二甲基-2,3,6,7-四氢-1H-5,8-二氧杂-1,3-二氮杂环五[b]萘和ZnPc的混合汽相淀积。得到的传导率为2.2×10-8 S/cm。
实施例X:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3-二甲基-2-异丙基-1,2-二氢苯并咪唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为10-3S/cm。
实施例XI:
以与实施例I类似的方式,以在实施例I中给出的比例进行双-[1,3-二乙基-2-甲基-1,2-二氢苯并噻唑基-(2)]和ZnPc的混合汽相淀积。得到的传导率为3.8×10-7S/cm。
在上述说明书和权利要求书中公开的本发明的特征可以单独或彼此组合方式来完成本发明的不同实施方式。
Claims (14)
1.一种杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,具有下式的结构:
其中结构3和4具有一个或多个环状连接A和/或A1和/或A2,其中A,A1和A2可以是碳环、杂环和/或多环环系,其可以是取代或未取代的;
其中A1和A2可以单独或一起存在,且A1和A2如对结构3和4所定义的,T=CR22,CR22R23,N,NR21,O或S;
其中结构7具有一个或多个桥键Z和/或Z1和/或Z2,且Z、Z1和Z2可独立选自烷基,烯基,炔基,环烷基,甲硅烷基;烷基甲硅烷基,重氮基,二硫化物,杂环烷基,杂环基,哌嗪基,二烷基醚,聚醚,伯烷基胺,芳基胺和多胺,芳基和杂芳基;
其中结构8a-8c中,各个杂环的环尺寸可在5-7个原子间变化;
其中X,Y=O,S,N,NR21,P或PR21;R0-19,R21,R22和R23独立选自取代或未取代的芳基,杂芳基,杂环,二芳基胺,二杂芳基胺,二烷基胺,杂芳基烷基胺,芳基烷基胺,H,F,环烷基,卤代环烷基,杂环烷基,烷基,烯基,炔基,三烷基甲硅烷基,三芳基甲硅烷基,卤素,苯乙烯基,烷氧基,芳氧基,硫代烷氧基,硫代芳氧基,甲硅烷基和三烷基甲硅烷基炔基,或R0-19,R21,R22和R23,单独或结合形成(杂)脂肪族或(杂)芳香族环系的部分;
条件是排除以下结构:
结构3a
结构3a
结构1
其中X=NR21,Y=NR22和R1,2,21,22=苯基,,4-甲苯基和/或4-茴香基,R0=苯基,4-甲苯基或4-茴香基。
2.根据权利要求1的杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,其特征在于A,A1和A2选自取代或未取代的芳香族和杂芳香族环系,优选为苯并,萘并,噻吩,呋喃,噻唑,咪唑,噁唑,噻二唑,吡嗪,噻喃,dithiine,邻苯二甲酸酰亚胺和二噻唑自由基,其中可存在一个或多个取代基,其选自R0-R19,R21,R22和R23。
3.根据权利要求1或2的杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,其特征在于Z,Z1和Z2选自哌嗪基和烷基或环烷基。
5.根据前述任一项权利要求的杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,其特征在于R0-19,R21,R22和R23选自取代或未取代的苯基,二苯基,萘基,anthranyl,噻吩基,咪唑基,吡咯基,噻唑基,噁唑基,噻二唑基,哌啶基,吡咯烷基,吗啡酚基和硫代吗啡酚基。
6.根据前述任一项权利要求的杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,其特征在于R0-19,R21,R22和R23选自烷基,环烷基,二烷基胺,二芳基胺,烷氧基,芳氧基,硫代芳基,硫代烷氧基,全氟烷基。
7.一种杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环,其特征在于所述的多环是三环。
8.根据前述权利要求1-6任一项的杂环的自由基或双自由基,其二聚物,低聚物,聚合物,二螺化合物和多环作为用于掺杂有机半导体基体材料的掺杂剂,作为阻挡层,作为电荷注入层,作为电极材料,作为记忆材料或作为电子和光电元件中的半导体层自身的用途。
9.一种含有至少一种有机基体化合物和掺杂剂的有机半导体材料,其特征在于所述的掺杂剂是权利要求1-7的至少一种化合物。
10.根据权利要求9的有机半导体材料,其特征在于掺杂剂与基体分子的掺杂摩尔比或掺杂剂与聚合物基体分子的单体单元的掺杂比为1∶1和1∶100000。
11.一种制备含有有机基体分子和掺杂剂的有机半导体材料的方法,其特征在于至少一种根据权利要求1-7任一项的化合物用作掺杂剂。
12.一种具有电功能活性区域的电子或光电元件,其特征在于所述的电活性区域包括至少一种权利要求1-7的化合物。
13.根据权利要求12的电子或光电元件,其特征在于所述的电活性区域包括有机半导体基体材料,所述有机半导体基体材料利用根据权利要求1-7的至少一种化合物,用至少一种掺杂剂掺杂以改性所述半导体基体材料的电子性能。
14.根据权利要求12或13的电子或光电元件,其为有机发光二极管,光电池,有机太阳能电池,有机二极管,有机场效应晶体管或光敏和磁存储器的形式。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06005687A EP1837926B1 (de) | 2006-03-21 | 2006-03-21 | Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement |
EP06005687.6 | 2006-03-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101134744A true CN101134744A (zh) | 2008-03-05 |
CN101134744B CN101134744B (zh) | 2012-07-04 |
Family
ID=36809608
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200780009954.7A Active CN101405884B (zh) | 2006-03-21 | 2007-03-21 | 制备掺杂的有机半导体材料的方法以及在该方法中使用的配方物 |
CN2007100896620A Active CN101093874B (zh) | 2006-03-21 | 2007-03-21 | 由基质和掺杂材料组成的混合物,及由其构成层的方法 |
CN2007100889082A Active CN101134744B (zh) | 2006-03-21 | 2007-03-21 | 杂环的化合物,其用途、有机半导体材料和电子或光电元件 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200780009954.7A Active CN101405884B (zh) | 2006-03-21 | 2007-03-21 | 制备掺杂的有机半导体材料的方法以及在该方法中使用的配方物 |
CN2007100896620A Active CN101093874B (zh) | 2006-03-21 | 2007-03-21 | 由基质和掺杂材料组成的混合物,及由其构成层的方法 |
Country Status (10)
Country | Link |
---|---|
US (2) | US8134146B2 (zh) |
EP (1) | EP1837926B1 (zh) |
JP (1) | JP4939988B2 (zh) |
KR (1) | KR100885582B1 (zh) |
CN (3) | CN101405884B (zh) |
AT (1) | ATE394800T1 (zh) |
DE (1) | DE502006000749D1 (zh) |
ES (1) | ES2310380T3 (zh) |
HK (1) | HK1104677A1 (zh) |
TW (1) | TWI436985B (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102456844A (zh) * | 2010-10-25 | 2012-05-16 | 乐金显示有限公司 | 有机发光二极管及其制造方法 |
CN103052643A (zh) * | 2010-08-05 | 2013-04-17 | 巴斯夫欧洲公司 | 由桥接二噻唑共聚物制备的半导体材料 |
CN104364925A (zh) * | 2012-01-20 | 2015-02-18 | 南加利福尼亚大学 | 作为用于有机电子的新型n-型材料的氮杂-并苯的合成 |
CN104685648A (zh) * | 2012-09-07 | 2015-06-03 | 诺瓦尔德股份有限公司 | 电荷传输半导体材料和半导体器件 |
CN107210364A (zh) * | 2015-01-19 | 2017-09-26 | 西门子公司 | 氨基磷腈碱作为有机电子产品中的n型掺杂剂 |
CN108218836A (zh) * | 2016-12-09 | 2018-06-29 | 南京工业大学 | 苯并咪唑类n-型材料及其在OLEDs中的应用 |
CN109320528A (zh) * | 2018-10-27 | 2019-02-12 | 湖北大学 | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 |
Families Citing this family (254)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE502005009802D1 (de) * | 2005-11-10 | 2010-08-05 | Novaled Ag | Dotiertes organisches Halbleitermaterial |
US7919010B2 (en) * | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
EP1837927A1 (de) * | 2006-03-22 | 2007-09-26 | Novaled AG | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
JP5683104B2 (ja) * | 2006-03-21 | 2015-03-11 | ノヴァレッド・アクチエンゲゼルシャフト | ドープされた有機半導体材料の製造方法及びそのために用いられる配合物 |
US7572482B2 (en) * | 2006-04-14 | 2009-08-11 | Bae Systems Information And Electronic Systems Integration Inc. | Photo-patterned carbon electronics |
EP1912268B1 (de) * | 2006-10-09 | 2020-01-01 | Novaled GmbH | Verfahren zur räumlichen Strukturierung der Leuchtdichte von lichtermittierenden organischen Halbleiterbauelementen, danach hergestelltes Halbleiterbauelement und Verwendung desselben |
DE102007012794B3 (de) * | 2007-03-16 | 2008-06-19 | Novaled Ag | Pyrido[3,2-h]chinazoline und/oder deren 5,6-Dihydroderivate, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial |
DE102007018456B4 (de) * | 2007-04-19 | 2022-02-24 | Novaled Gmbh | Verwendung von Hauptgruppenelementhalogeniden und/oder -pseudohalogeniden, organisches halbleitendes Matrixmaterial, elektronische und optoelektronische Bauelemente |
EP3457451B1 (de) | 2007-04-30 | 2019-07-17 | Novaled GmbH | Die verwendung von oxokohlenstoff-, pseudooxokohlenstoff- und radialenverbindungen |
EP1990847B1 (de) * | 2007-05-10 | 2018-06-20 | Novaled GmbH | Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials |
DE102007028236A1 (de) * | 2007-06-20 | 2009-01-02 | Siemens Ag | Halbleitendes Material und organische Gleichrichterdiode |
EP2009014B1 (de) * | 2007-06-22 | 2018-10-24 | Novaled GmbH | Verwendung eines Precursors eines n-Dotanden zur Dotierung eines organischen halbleitenden Materials, Precursor und elektronisches oder optoelektronisches Bauelement |
DE102007031220B4 (de) | 2007-07-04 | 2022-04-28 | Novaled Gmbh | Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen |
DE102008011185A1 (de) * | 2008-02-27 | 2009-09-03 | Osram Opto Semiconductors Gmbh | Verfahren zur Herstellung einer dotierten organischen halbleitenden Schicht |
US8057712B2 (en) * | 2008-04-29 | 2011-11-15 | Novaled Ag | Radialene compounds and their use |
GB2467316B (en) | 2009-01-28 | 2014-04-09 | Pragmatic Printing Ltd | Electronic devices, circuits and their manufacture |
JP5498680B2 (ja) * | 2008-10-02 | 2014-05-21 | 山本化成株式会社 | 有機トランジスタ |
DE102009013685B4 (de) | 2009-03-20 | 2013-01-31 | Novaled Ag | Verwendung einer organischen Diode als organische Zenerdiode und Verfahren zum Betreiben |
US8603642B2 (en) * | 2009-05-13 | 2013-12-10 | Global Oled Technology Llc | Internal connector for organic electronic devices |
GB2473200B (en) | 2009-09-02 | 2014-03-05 | Pragmatic Printing Ltd | Structures comprising planar electronic devices |
TWI388548B (zh) * | 2009-09-23 | 2013-03-11 | Benq Materials Corp | 離子性化合物、包含其之抗靜電壓感黏合劑以及偏光片 |
EP2312663B1 (en) | 2009-10-19 | 2014-10-15 | Novaled AG | Organic electronic device comprising an organic semiconducting material |
US20120205645A1 (en) | 2009-10-28 | 2012-08-16 | Basf Se | Heteroleptic carbene complexes and the use thereof in organic electronics |
KR101838199B1 (ko) | 2009-12-14 | 2018-04-26 | 유디씨 아일랜드 리미티드 | 디아자벤즈이미다졸로카르벤 리간드를 포함하는 금속 착물 및 oled에서의 그의 용도 |
JP5392778B2 (ja) * | 2010-01-14 | 2014-01-22 | 独立行政法人産業技術総合研究所 | 電池およびキャパシタの電極材料 |
US8691401B2 (en) | 2010-04-16 | 2014-04-08 | Basf Se | Bridged benzimidazole-carbene complexes and use thereof in OLEDS |
EP2395571B1 (en) | 2010-06-10 | 2013-12-04 | Novaled AG | Organic electronic device comprising an organic semiconducting material |
CN103038224A (zh) * | 2010-07-30 | 2013-04-10 | 日本瑞翁株式会社 | 醚化合物、非水系电池用电解液组合物、非水系电池电极用粘合剂组合物、非水系电池电极用浆料组合物、非水系电池用电极及非水系电池 |
US20140144509A1 (en) | 2010-09-10 | 2014-05-29 | Novaled Ag | Compounds for Organic Photovoltaic Devices |
US20120177813A1 (en) * | 2010-10-17 | 2012-07-12 | Thompson Mark E | Chemical annealing method for fabrication of organic thin films for optoelectronic devices |
JP2012195054A (ja) | 2011-03-14 | 2012-10-11 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2014520394A (ja) | 2011-06-09 | 2014-08-21 | ノヴァレッド・アクチエンゲゼルシャフト | 有機電子素子のための化合物 |
CN107501330A (zh) | 2011-06-14 | 2017-12-22 | Udc 爱尔兰有限责任公司 | 包含氮杂苯并咪唑碳烯配体的金属配合物及其在oled中的用途 |
US9315724B2 (en) | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
US9722183B2 (en) | 2011-11-30 | 2017-08-01 | Novaled Gmbh | Display |
EP2789028B1 (en) | 2011-12-06 | 2019-02-06 | Novaled GmbH | Organic light emitting device and method of producing |
DE102012205945A1 (de) | 2012-04-12 | 2013-10-17 | Siemens Aktiengesellschaft | Organische Superdonoren mit mindestens zwei gekoppelten Carben-Gruppen und deren Verwendung als n-Dotierstoffe |
KR102034916B1 (ko) | 2012-07-19 | 2019-10-21 | 유디씨 아일랜드 리미티드 | 카르벤 리간드를 포함하는 이핵 금속 착물 및 oled에서의 그의 용도 |
JP6333262B2 (ja) | 2012-09-20 | 2018-05-30 | ユー・ディー・シー アイルランド リミテッド | 電子用途のためのアザジベンゾフラン |
US9882150B2 (en) | 2012-09-24 | 2018-01-30 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
WO2014072320A1 (en) | 2012-11-06 | 2014-05-15 | Basf Se | Phenoxasiline based compounds for electronic application |
JP6377718B2 (ja) | 2013-03-20 | 2018-08-22 | ユー・ディー・シー アイルランド リミテッド | Oledにおける高効率ブースターとしてのアザベンズイミダゾールカルベン錯体 |
KR102098340B1 (ko) | 2013-04-29 | 2020-04-13 | 유디씨 아일랜드 리미티드 | 카르벤 리간드를 갖는 전이 금속 착물 및 oled에서의 그의 용도 |
KR102305557B1 (ko) | 2013-07-02 | 2021-09-29 | 유디씨 아일랜드 리미티드 | 유기 발광 다이오드에 사용하기 위한 일치환된 디아자벤즈이미다졸 카르벤 금속 착체 |
CN109021022B (zh) | 2013-07-31 | 2021-04-16 | Udc 爱尔兰有限责任公司 | 发光的二氮杂苯并咪唑碳烯金属配合物 |
EP2840622B1 (en) | 2013-08-19 | 2019-02-13 | Novaled GmbH | Electronic or optoelectronic device comprising an anchored thin molecular layer, process for its preparation and compound used therein |
DE102013013876A1 (de) | 2013-08-20 | 2015-03-12 | Merck Patent Gmbh | Metallkomplexe |
JP6804823B2 (ja) | 2013-10-14 | 2020-12-23 | アリゾナ・ボード・オブ・リージェンツ・オン・ビハーフ・オブ・アリゾナ・ステイト・ユニバーシティーArizona Board of Regents on behalf of Arizona State University | 白金錯体およびデバイス |
WO2015063046A1 (en) | 2013-10-31 | 2015-05-07 | Basf Se | Azadibenzothiophenes for electronic applications |
JP6107605B2 (ja) * | 2013-11-05 | 2017-04-05 | コニカミノルタ株式会社 | 有機エレクトロルミッセンス素子、及び照明装置 |
US10374170B2 (en) | 2013-12-06 | 2019-08-06 | Merck Patent Gmbh | Substituted oxepines |
EP3708634A1 (de) | 2013-12-19 | 2020-09-16 | Merck Patent GmbH | Heterocyclische spiroverbindungen |
CN105993083B (zh) | 2013-12-20 | 2018-07-03 | Udc 爱尔兰有限责任公司 | 具有极短衰变时间的高效oled装置 |
US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
CN106661068A (zh) | 2014-03-31 | 2017-05-10 | Udc 爱尔兰有限责任公司 | 包含具有o‑取代非环金属化芳基的碳烯配位体的金属络合物和其在有机发光二极管中的用途 |
US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
JP6525599B2 (ja) * | 2014-06-27 | 2019-06-05 | キヤノン株式会社 | 有機化合物、電界素子、有機発光素子、表示装置、画像情報処理装置、照明装置、画像形成装置、露光装置 |
KR102479149B1 (ko) | 2014-07-21 | 2022-12-19 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
WO2016016791A1 (en) | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
TWI690534B (zh) | 2014-08-08 | 2020-04-11 | 愛爾蘭商Udc愛爾蘭責任有限公司 | 電致發光咪唑并喹噁啉碳烯金屬錯合物 |
WO2016029137A1 (en) | 2014-08-22 | 2016-02-25 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light-emitting diodes with fluorescent and phosphorescent emitters |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
CN106687563B (zh) | 2014-09-05 | 2023-03-14 | 默克专利有限公司 | 制剂和电子器件 |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
WO2016079169A1 (en) | 2014-11-18 | 2016-05-26 | Basf Se | Pt- or pd-carbene complexes for use in organic light emitting diodes |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
KR102570137B1 (ko) | 2015-03-30 | 2023-08-23 | 메르크 파텐트 게엠베하 | 실록산 용매를 포함하는 유기 기능성 재료의 제형 |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
JP6552257B2 (ja) | 2015-04-30 | 2019-07-31 | キヤノン株式会社 | 1位、1’位、3位、3’位に複素単環基を有する、2,2’−ビベンゾ[d]イミダゾリデン化合物、それを有する有機発光素子、表示装置 |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9879039B2 (en) | 2015-06-03 | 2018-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
CN111668392B (zh) | 2015-06-03 | 2024-01-23 | Udc 爱尔兰有限责任公司 | 具有极短衰减时间的高效oled装置 |
WO2016198141A1 (en) | 2015-06-12 | 2016-12-15 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for oled formulations |
CN106316960A (zh) * | 2015-07-02 | 2017-01-11 | 昆山国显光电有限公司 | 苯并咪唑类n-型掺杂剂及其在有机电致发光器件中的应用 |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11046884B2 (en) | 2015-08-28 | 2021-06-29 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
US10672996B2 (en) | 2015-09-03 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3356368B1 (en) | 2015-10-01 | 2021-07-21 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
WO2017056055A1 (en) | 2015-10-01 | 2017-04-06 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
US20180319813A1 (en) | 2015-11-04 | 2018-11-08 | Idemitsu Kosan Co., Ltd | Benzimidazole fused heteroaryls |
GB2544768A (en) * | 2015-11-25 | 2017-05-31 | Cambridge Display Tech Ltd | Charge transfer salt, electronic device and method of forming the same |
US11174258B2 (en) | 2015-12-04 | 2021-11-16 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
CN108368361A (zh) | 2015-12-10 | 2018-08-03 | 默克专利有限公司 | 含有包含非芳族环的酮的制剂 |
US11171294B2 (en) | 2015-12-15 | 2021-11-09 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
EP3390549B1 (en) | 2015-12-16 | 2022-06-29 | Merck Patent GmbH | Formulations containing a solid solvent |
KR20180095028A (ko) | 2015-12-16 | 2018-08-24 | 메르크 파텐트 게엠베하 | 둘 이상의 상이한 용매의 혼합물을 함유하는 제형 |
CN106898701B (zh) * | 2015-12-18 | 2018-11-13 | 昆山国显光电有限公司 | 一种有机电致发光器件 |
JP6375069B2 (ja) | 2015-12-21 | 2018-08-15 | 出光興産株式会社 | ヘテロ原子で架橋されたフェニルキナゾリン |
KR20170074170A (ko) | 2015-12-21 | 2017-06-29 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 oled에서의 이의 용도 |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2017140404A1 (en) | 2016-02-17 | 2017-08-24 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3208863B1 (en) | 2016-02-22 | 2019-10-23 | Novaled GmbH | Charge transporting semi-conducting material and electronic device comprising it |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
JP6851725B2 (ja) | 2016-03-29 | 2021-03-31 | 住友化学株式会社 | 新規化合物及びその製造方法 |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
WO2017216129A1 (en) | 2016-06-16 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
JP2019523998A (ja) | 2016-06-17 | 2019-08-29 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
TW201815998A (zh) | 2016-06-28 | 2018-05-01 | 德商麥克專利有限公司 | 有機功能材料之調配物 |
JP6980757B2 (ja) | 2016-08-04 | 2021-12-15 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10822363B2 (en) | 2016-10-12 | 2020-11-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Narrow band red phosphorescent tetradentate platinum (II) complexes |
EP3312899B1 (en) | 2016-10-24 | 2021-04-07 | Novaled GmbH | Electron transport layer stack for an organic light-emitting diode |
EP3312895B1 (en) | 2016-10-24 | 2021-07-28 | Novaled GmbH | Organic semiconducting material comprising an electrical n-dopant and an electron transport matrix and electronic device comprising the semiconducting material |
EP3312896B1 (en) | 2016-10-24 | 2021-03-31 | Novaled GmbH | Organic electroluminescent device comprising a redox-doped electron transport layer and an auxiliary electron transport layer |
US11538992B2 (en) | 2016-10-31 | 2022-12-27 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018077662A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
CN110036498B (zh) | 2016-12-06 | 2023-04-18 | 默克专利有限公司 | 电子器件的制备方法 |
CN110168047B (zh) | 2016-12-13 | 2023-08-08 | 默克专利有限公司 | 有机功能材料的制剂 |
US11183670B2 (en) | 2016-12-16 | 2021-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light emitting diode with split emissive layer |
TW201835300A (zh) | 2016-12-22 | 2018-10-01 | 德商麥克專利有限公司 | 包含至少二種有機官能性化合物之混合物 |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20190139835A (ko) | 2017-01-27 | 2019-12-18 | 아리조나 보드 오브 리젠츠 온 비하프 오브 아리조나 스테이트 유니버시티 | 피리도-피롤로-아크리딘 및 유사체를 사용하는 금속 보조 지연 형광 이미터 |
TWI763772B (zh) | 2017-01-30 | 2022-05-11 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
TWI791481B (zh) | 2017-01-30 | 2023-02-11 | 德商麥克專利有限公司 | 形成有機電致發光(el)元件之方法 |
EP3355378B1 (en) | 2017-01-30 | 2022-12-28 | Novaled GmbH | Electroluminescent device comprising a defined layer arrangement comprising a light emitting layer, a hole transport layer and an electron transport layer |
EP3369729B1 (en) | 2017-03-02 | 2022-01-12 | Novaled GmbH | Fused 9-phenyl-acridine derivatives for use in an electronic device and display device |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20190131554A (ko) | 2017-03-31 | 2019-11-26 | 메르크 파텐트 게엠베하 | 유기 발광 다이오드 (oled) 를 위한 인쇄 방법 |
CN110494514A (zh) | 2017-04-10 | 2019-11-22 | 默克专利有限公司 | 有机功能材料的制剂 |
TW201902891A (zh) | 2017-04-13 | 2019-01-16 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
JP7330898B2 (ja) | 2017-05-03 | 2023-08-22 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
DE102017111137A1 (de) | 2017-05-22 | 2018-11-22 | Novaled Gmbh | Organische elektrolumineszente Vorrichtung |
EP3407401A1 (en) | 2017-05-23 | 2018-11-28 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer and a device |
EP3406599B1 (en) | 2017-05-23 | 2023-02-22 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
GB2563430A (en) | 2017-06-15 | 2018-12-19 | Sumitomo Chemical Co | Compound |
EP3418285B1 (en) | 2017-06-20 | 2020-05-06 | Idemitsu Kosan Co., Ltd. | Composition comprising a substituted ir complex and a phenylquinazoline bridged with a heteroatom |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2019002198A1 (en) | 2017-06-26 | 2019-01-03 | Merck Patent Gmbh | HOMOGENEOUS MIXTURES |
US11591320B2 (en) | 2017-07-05 | 2023-02-28 | Merck Patent Gmbh | Composition for organic electronic devices |
KR102653984B1 (ko) | 2017-07-05 | 2024-04-02 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스용 조성물 |
KR20200030573A (ko) | 2017-07-18 | 2020-03-20 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3466954A1 (en) | 2017-10-04 | 2019-04-10 | Idemitsu Kosan Co., Ltd. | Fused phenylquinazolines bridged with a heteroatom |
EP3470412B1 (en) | 2017-10-13 | 2020-07-22 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
EP3470398B1 (en) | 2017-10-13 | 2022-05-04 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
KR20200065064A (ko) | 2017-10-17 | 2020-06-08 | 지안 리 | 표시 및 조명 분야용 단색성 이미터로서의, 바람직한 분자 배향을 갖는 인광성 엑시머 |
US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
EP3483154A1 (en) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine, fluorene and aryl groups and their use in organic electronic devices |
EP3483153A1 (en) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine group, fluorene-group and aryl group and their use in organic electronic devices |
TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20200093653A (ko) | 2017-12-15 | 2020-08-05 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3524593B1 (en) | 2018-02-07 | 2023-04-12 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
WO2019162483A1 (en) | 2018-02-26 | 2019-08-29 | Merck Patent Gmbh | Formulation of an organic functional material |
EP3533788A1 (en) | 2018-02-28 | 2019-09-04 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
KR20210016423A (ko) | 2018-05-30 | 2021-02-15 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스용 조성물 |
EP3582280B1 (en) | 2018-06-14 | 2024-03-20 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
JP7379389B2 (ja) | 2018-06-15 | 2023-11-14 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112740432A (zh) | 2018-09-24 | 2021-04-30 | 默克专利有限公司 | 用于生产粒状材料的方法 |
DE102018125307A1 (de) | 2018-10-12 | 2020-04-16 | Novaled Gmbh | Organische lichtemittierende Vorrichtung |
EP3878022A1 (en) | 2018-11-06 | 2021-09-15 | Merck Patent GmbH | Method for forming an organic element of an electronic device |
EP3653619A1 (en) | 2018-11-16 | 2020-05-20 | Novaled GmbH | Compound, organic electronic device comprising the same, and display device and lighting device comprising the same |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3667753A3 (en) | 2018-12-14 | 2020-12-23 | Novaled GmbH | Organic light emitting device and a compound for use therein |
CN109651370A (zh) * | 2018-12-17 | 2019-04-19 | 桂林理工大学 | 一种嘌呤类衍生物自由基前体分子及其制备方法 |
US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
EP3742513A1 (en) | 2019-05-21 | 2020-11-25 | Novaled GmbH | Organic light emitting diode |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3840080A1 (en) | 2019-12-17 | 2021-06-23 | Novaled GmbH | Organic electronic device and display device comprising the organic electronic device |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230151235A1 (en) | 2020-04-21 | 2023-05-18 | Merck Patent Gmbh | Formulation of an organic functional material |
US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
DE112021003032A5 (de) | 2020-05-29 | 2023-03-16 | Technische Universität Bergakademie Freiberg | Perimidin-Derivate und deren Verwendung |
EP3923364A1 (en) | 2020-06-12 | 2021-12-15 | Novaled GmbH | Organic light emitting diode and device comprising the same |
US20230225201A1 (en) | 2020-06-12 | 2023-07-13 | Novaled Gmbh | Organic Light Emitting Diode and Device Comprising the Same |
WO2021259824A1 (de) | 2020-06-23 | 2021-12-30 | Merck Patent Gmbh | Verfahren zur herstellung einer mischung |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220112232A1 (en) | 2020-10-02 | 2022-04-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20230114756A (ko) | 2020-12-08 | 2023-08-01 | 메르크 파텐트 게엠베하 | 잉크 시스템 및 잉크젯 인쇄를 위한 방법 |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
EP4326826A1 (en) | 2021-04-23 | 2024-02-28 | Merck Patent GmbH | Formulation of an organic functional material |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4340969A1 (de) | 2021-05-21 | 2024-03-27 | Merck Patent GmbH | Verfahren zur kontinuierlichen aufreinigung von mindestens einem funktionalen material und vorrichtung zur kontinuierlichen aufreinigung von mindestens einem funktionalen material |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
DE102021118308A1 (de) | 2021-07-15 | 2023-01-19 | Technische Universität Bergakademie Freiberg, Körperschaft des öffentlichen Rechts | Elektronenreiche heterocyclische Dimere und deren Verwendung |
EP4141979A1 (en) | 2021-08-24 | 2023-03-01 | Novaled GmbH | Organic light emitting diode and a compound for use therein |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4156314A1 (en) | 2021-09-27 | 2023-03-29 | Novaled GmbH | Organic electronic device and a compound |
TW202349760A (zh) | 2021-10-05 | 2023-12-16 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
CN114047156B (zh) * | 2021-10-09 | 2022-10-18 | 中南民族大学 | 一种霍山石斛栽培方式和年限的鉴别方法 |
EP4177978A1 (en) | 2021-11-05 | 2023-05-10 | Novaled GmbH | Organic light emitting diode, a display device comprising the same and a lighting device comprising the same |
CN117343078A (zh) | 2021-11-25 | 2024-01-05 | 北京夏禾科技有限公司 | 有机电致发光材料和器件 |
EP4198103A1 (en) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP4199125A1 (en) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organic light emitting diode, method for preparing the same and device comprising the same |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4199133A1 (en) | 2021-12-20 | 2023-06-21 | Novaled GmbH | Organic light emitting diode, display device comprising the same, and compound |
EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4273947A1 (en) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP4273948A1 (en) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organic light emitting diode and device comprising the same |
US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4299573A1 (en) | 2022-06-30 | 2024-01-03 | Novaled GmbH | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and a method for preparing the organic electronic device |
EP4321511A1 (en) | 2022-08-09 | 2024-02-14 | Novaled GmbH | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and display device comprising the same |
US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4346356A1 (en) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the semiconducting material and compound |
EP4346357A1 (en) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the organic semiconducting material, display device comprising the organic semiconducting device and compound |
Family Cites Families (78)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2566208A (en) | 1948-10-13 | 1951-08-28 | Monsanto Chemicals | Dielectric composition of halogenated aromatic hydrocarbon and organic antimony compound as a corrosion inhibitor |
CH354066A (de) | 1955-07-05 | 1961-05-15 | Metal & Thermit Corp | Verfahren zur Herstellung von Alkoholen |
CH354065A (de) | 1955-07-05 | 1961-05-15 | Metal & Thermit Corp | Verfahren zur Herstellung von Alkoholen |
US3083242A (en) | 1956-09-19 | 1963-03-26 | M & T Chemicals Inc | Preparation of certain organomagnesium chlorides in ethylene polyethers |
DE1140576B (de) | 1961-09-21 | 1962-12-06 | Bayer Ag | Verfahren zur Herstellung von Arylmagnesiumhalogeniden |
US3563751A (en) | 1967-07-20 | 1971-02-16 | Du Pont | Hexaarylbiimidazole-acridine dye compositions |
US3558671A (en) | 1967-08-30 | 1971-01-26 | Du Pont | Fluoro- and cyano-substituted 7,7,8,8-tetracyanoquinodimethans and intermediates thereto |
JPS4948172B1 (zh) * | 1970-12-28 | 1974-12-19 | ||
US4003943A (en) | 1974-12-20 | 1977-01-18 | E. I. Du Pont De Nemours And Company | Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same |
US4066569A (en) | 1975-12-30 | 1978-01-03 | Hughes Aircraft Company | Dopants for dynamic scattering liquid crystals |
US4133821A (en) | 1977-03-15 | 1979-01-09 | Wisconsin Alumni Research Foundation | Alkylidenediquinocyclopropanes and Diarylcyclopropenes and method for preparation |
JPS61254582A (ja) | 1985-05-04 | 1986-11-12 | Mitsubishi Chem Ind Ltd | テトラキス(1,3−ジチオ−ル−2−イリデン)〔4〕ラジアレン類 |
US4618453A (en) | 1985-05-30 | 1986-10-21 | The United States Of America As Represented By The Secretary Of The Navy | Conductive heterocyclic ladder polymers |
JPS63172274A (ja) | 1987-01-12 | 1988-07-15 | Alps Electric Co Ltd | 光導電性被膜およびそれを用いた電子写真感光体 |
JPS63172275A (ja) | 1987-01-12 | 1988-07-15 | Alps Electric Co Ltd | 光導電性被膜およびそれを用いた電子写真感光体 |
US4960916A (en) | 1989-09-29 | 1990-10-02 | United States Of America As Represented By The Secretary Of The Navy | Organometallic antimony compounds useful in chemical vapor deposition processes |
DE4024871A1 (de) | 1990-08-06 | 1992-02-13 | Basf Ag | Perlfoermige antistatische expandierbare styrolpolymerisate |
US5093698A (en) | 1991-02-12 | 1992-03-03 | Kabushiki Kaisha Toshiba | Organic electroluminescent device |
DE4106122A1 (de) | 1991-02-27 | 1992-09-03 | Bayer Ag | Neue naphthalimide, diese enthaltende toner und die verwendung der neuen naphthalimide als additive fuer toner |
JP2998268B2 (ja) | 1991-04-19 | 2000-01-11 | 三菱化学株式会社 | 有機電界発光素子 |
JPH04338760A (ja) | 1991-05-15 | 1992-11-26 | Konica Corp | 電子写真感光体 |
US5393614A (en) | 1992-04-03 | 1995-02-28 | Pioneer Electronic Corporation | Organic electroluminescence device |
US5281730A (en) | 1992-04-22 | 1994-01-25 | Ciba-Geigy Corporation | Substituted tetracyanoquinodimethanes, processes for their preparation and their use |
JPH07168377A (ja) | 1993-12-16 | 1995-07-04 | Konica Corp | 電子写真感光体 |
JP3256361B2 (ja) | 1993-12-29 | 2002-02-12 | 昭和電工株式会社 | ポリ(アルキル置換−2,5−ピリミジンジイル)及びその製造方法 |
FI95574C (fi) | 1994-02-16 | 1996-02-26 | Valtion Teknillinen | Elektroneja johtavia molekyylivalmisteita |
DE59510315D1 (de) | 1994-04-07 | 2002-09-19 | Covion Organic Semiconductors | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US5811833A (en) | 1996-12-23 | 1998-09-22 | University Of So. Ca | Electron transporting and light emitting layers based on organic free radicals |
JPH10270171A (ja) | 1997-01-27 | 1998-10-09 | Junji Kido | 有機エレクトロルミネッセント素子 |
DE19756361A1 (de) | 1997-12-18 | 1999-06-24 | Philips Patentverwaltung | Organische lichtemittierende Diode mit Terbiumkomplex |
JPH11251067A (ja) | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
DE19836408A1 (de) | 1998-08-12 | 2000-02-24 | Basf Ag | Verfahren zur Herstellung von Grignardverbindungen |
JP3389888B2 (ja) | 1998-11-09 | 2003-03-24 | 東レ株式会社 | 発光素子 |
DE19858856A1 (de) | 1998-12-19 | 2000-06-21 | Merck Patent Gmbh | Verfahren zur Herstellung von Arylmetallverbindungen und deren Umsetzung mit Elektrophilen |
US6103459A (en) | 1999-03-09 | 2000-08-15 | Midwest Research Institute | Compounds for use as chemical vapor deposition precursors, thermochromic materials light-emitting diodes, and molecular charge-transfer salts and methods of making these compounds |
JP2001131174A (ja) | 1999-11-02 | 2001-05-15 | Sony Corp | バソフェナントロリン化合物及びその製造方法 |
JP3924648B2 (ja) | 1999-11-02 | 2007-06-06 | ソニー株式会社 | 有機電界発光素子 |
AU2001257542A1 (en) | 2000-05-03 | 2001-11-12 | The Regents Of The University Of California | Soluble tetrahedral compounds for use in electroluminescent devices |
JP2001319698A (ja) | 2000-05-11 | 2001-11-16 | Fuji Photo Film Co Ltd | 光電変換素子および光電池 |
EP1160888A1 (en) | 2000-05-29 | 2001-12-05 | Sony International (Europe) GmbH | Hole transporting agents and photoelectric conversion device comprising the same |
JP3998903B2 (ja) | 2000-09-05 | 2007-10-31 | 出光興産株式会社 | 新規アリールアミン化合物及び有機エレクトロルミネッセンス素子 |
US6699597B2 (en) | 2001-08-16 | 2004-03-02 | 3M Innovative Properties Company | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein |
JP3823312B2 (ja) | 2001-10-18 | 2006-09-20 | 日本電気株式会社 | 有機薄膜トランジスタ |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
DE10207859A1 (de) | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
DE10212926A1 (de) | 2002-03-22 | 2003-10-16 | Infineon Technologies Ag | Halbleiterspeicherzelle und Halbleiterspeichereinrichtung |
AU2002323418A1 (en) | 2002-04-08 | 2003-10-27 | The University Of Southern California | Doped organic carrier transport materials |
TWI314947B (en) | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
DE10224021B4 (de) | 2002-05-24 | 2006-06-01 | Novaled Gmbh | Phosphoreszentes lichtemittierendes Bauelement mit organischen Schichten |
JP3960131B2 (ja) | 2002-06-05 | 2007-08-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、及びそれを用いた有機エレクトロルミネッセンス素子および表示装置 |
ES2197818B1 (es) | 2002-06-11 | 2005-02-01 | Institut Quimic De Sarria Cets | 2,7,12,17 alquenil, aril y heteroaril derivados del 3,6,13,16-tetraazaporficeno, y procedimiento, compuesto intermedio y utilizaciones correspondientes. |
US7074534B2 (en) | 2002-07-10 | 2006-07-11 | E. I. Du Pont De Nemours And Company | Polymeric charge transport compositions and electronic devices made with such compositions |
DE10261662A1 (de) | 2002-12-20 | 2004-07-01 | Friedrich-Schiller-Universität Jena | Neue mit Pyrazinen verknüpfte 1,4,5,8-Tetraazafulvalene und Verfahren zu ihrer Herstellung |
US20050042390A1 (en) | 2003-01-09 | 2005-02-24 | Siegel Stephen B. | Rotary UV curing method and apparatus |
BRPI0408493B1 (pt) | 2003-03-19 | 2018-09-18 | Heliatek Gmbh | componente fotoativo orgânico |
JP2004335557A (ja) | 2003-04-30 | 2004-11-25 | Ricoh Co Ltd | 縦型有機トランジスタ |
EP1477892B1 (en) | 2003-05-16 | 2015-12-23 | Sap Se | System, method, computer program product and article of manufacture for inputting data in a computer system |
WO2005032399A2 (en) * | 2003-05-30 | 2005-04-14 | The Regents Of The University Of California | Il4 receptor antagonists for horse, dog and cat |
US20050023974A1 (en) | 2003-08-01 | 2005-02-03 | Universal Display Corporation | Protected organic electronic devices and methods for making the same |
DE10338406A1 (de) | 2003-08-18 | 2005-03-24 | Novaled Gmbh | Dotierte organische Halbleitermaterialien sowie Verfahren zu deren Herstellung |
DE10339772B4 (de) | 2003-08-27 | 2006-07-13 | Novaled Gmbh | Licht emittierendes Bauelement und Verfahren zu seiner Herstellung |
US7655961B2 (en) | 2003-10-02 | 2010-02-02 | Maxdem Incorporated | Organic diodes and materials |
DE10357044A1 (de) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
DE102004010954A1 (de) | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
US7540978B2 (en) | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
EP1643568A1 (de) | 2004-10-04 | 2006-04-05 | Novaled GmbH | Verfahren zum Herstellen einer Schicht aus einem dotierten Halbleitermaterial und Vorrichtung |
WO2006062218A1 (en) | 2004-12-06 | 2006-06-15 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element and light-emitting device using the same |
WO2006067800A1 (en) | 2004-12-24 | 2006-06-29 | Council Of Scientific And Industrial Research | Triorganoantimony compounds for pesticidal use |
EP1869141B1 (de) | 2005-04-14 | 2020-03-11 | Merck Patent GmbH | Verbindungen für organische elektronische vorrichtungen |
US7563518B2 (en) | 2005-07-28 | 2009-07-21 | Eastman Kodak Company | Low voltage organic electroluminescent element |
US7582893B2 (en) | 2005-09-15 | 2009-09-01 | Spansion Llc | Semiconductor memory device comprising one or more injecting bilayer electrodes |
US20070116984A1 (en) | 2005-09-21 | 2007-05-24 | Doosan Corporation | Spiro-compound for electroluminescent display device and electroluminescent display device comprising the same |
DE502005009802D1 (de) | 2005-11-10 | 2010-08-05 | Novaled Ag | Dotiertes organisches Halbleitermaterial |
US7919010B2 (en) | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
DE102006039423A1 (de) | 2006-08-23 | 2008-02-28 | Werner, Johannes | Halbleitende Polyaddukte mit kolumnarer Struktur |
DE602007008337D1 (de) | 2006-10-24 | 2010-09-23 | Semiconductor Energy Lab | Anthrazenderivat und lichtemittierendes Element, lichtemittierende Vorrichtung und elektronische Vorrichtung mit Anthrazenderivat |
EP3457451B1 (de) | 2007-04-30 | 2019-07-17 | Novaled GmbH | Die verwendung von oxokohlenstoff-, pseudooxokohlenstoff- und radialenverbindungen |
-
2006
- 2006-03-21 EP EP06005687A patent/EP1837926B1/de active Active
- 2006-03-21 DE DE502006000749T patent/DE502006000749D1/de active Active
- 2006-03-21 AT AT06005687T patent/ATE394800T1/de not_active IP Right Cessation
- 2006-03-21 ES ES06005687T patent/ES2310380T3/es active Active
-
2007
- 2007-03-20 US US11/688,777 patent/US8134146B2/en active Active
- 2007-03-21 CN CN200780009954.7A patent/CN101405884B/zh active Active
- 2007-03-21 CN CN2007100896620A patent/CN101093874B/zh active Active
- 2007-03-21 TW TW096109810A patent/TWI436985B/zh active
- 2007-03-21 CN CN2007100889082A patent/CN101134744B/zh active Active
- 2007-03-21 KR KR1020070027688A patent/KR100885582B1/ko active IP Right Grant
- 2007-03-22 JP JP2007075182A patent/JP4939988B2/ja active Active
- 2007-11-27 HK HK07112942A patent/HK1104677A1/xx unknown
-
2012
- 2012-02-16 US US13/398,162 patent/US9118019B2/en active Active
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103052643A (zh) * | 2010-08-05 | 2013-04-17 | 巴斯夫欧洲公司 | 由桥接二噻唑共聚物制备的半导体材料 |
CN103052643B (zh) * | 2010-08-05 | 2016-03-09 | 巴斯夫欧洲公司 | 由桥接二噻唑共聚物制备的半导体材料 |
CN102456844A (zh) * | 2010-10-25 | 2012-05-16 | 乐金显示有限公司 | 有机发光二极管及其制造方法 |
CN104364925A (zh) * | 2012-01-20 | 2015-02-18 | 南加利福尼亚大学 | 作为用于有机电子的新型n-型材料的氮杂-并苯的合成 |
CN104685648A (zh) * | 2012-09-07 | 2015-06-03 | 诺瓦尔德股份有限公司 | 电荷传输半导体材料和半导体器件 |
CN104685648B (zh) * | 2012-09-07 | 2019-03-22 | 诺瓦尔德股份有限公司 | 电荷传输半导体材料和半导体器件 |
CN107210364A (zh) * | 2015-01-19 | 2017-09-26 | 西门子公司 | 氨基磷腈碱作为有机电子产品中的n型掺杂剂 |
CN107210364B (zh) * | 2015-01-19 | 2021-05-04 | 西门子公司 | 氨基磷腈碱作为有机电子产品中的n型掺杂剂 |
CN108218836A (zh) * | 2016-12-09 | 2018-06-29 | 南京工业大学 | 苯并咪唑类n-型材料及其在OLEDs中的应用 |
CN108218836B (zh) * | 2016-12-09 | 2020-09-04 | 南京工业大学 | 苯并咪唑类n-型材料及其在OLEDs中的应用 |
CN109320528A (zh) * | 2018-10-27 | 2019-02-12 | 湖北大学 | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 |
CN109320528B (zh) * | 2018-10-27 | 2021-04-13 | 湖北大学 | 室温下稳定发光的三杂芳基自由基及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN101093874B (zh) | 2013-02-13 |
TW200745050A (en) | 2007-12-16 |
US20070252140A1 (en) | 2007-11-01 |
US8134146B2 (en) | 2012-03-13 |
CN101134744B (zh) | 2012-07-04 |
ATE394800T1 (de) | 2008-05-15 |
CN101405884B (zh) | 2014-02-19 |
JP4939988B2 (ja) | 2012-05-30 |
US20120146012A1 (en) | 2012-06-14 |
TWI436985B (zh) | 2014-05-11 |
JP2007314513A (ja) | 2007-12-06 |
CN101405884A (zh) | 2009-04-08 |
EP1837926A1 (de) | 2007-09-26 |
US9118019B2 (en) | 2015-08-25 |
EP1837926B1 (de) | 2008-05-07 |
DE502006000749D1 (de) | 2008-06-19 |
HK1104677A1 (en) | 2008-01-18 |
KR100885582B1 (ko) | 2009-02-24 |
CN101093874A (zh) | 2007-12-26 |
KR20070095818A (ko) | 2007-10-01 |
ES2310380T3 (es) | 2009-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101134744B (zh) | 杂环的化合物,其用途、有机半导体材料和电子或光电元件 | |
JP2022116248A (ja) | 化合物 | |
CN108148073B (zh) | 有机半导体化合物 | |
Mikroyannidis et al. | Low band gap conjugated small molecules containing benzobisthiadiazole and thienothiadiazole central units: synthesis and application for bulk heterojunction solar cells | |
US10840450B2 (en) | Polymer, and mixture or formulation, and organic electronic device containing same, and monomer thereof | |
CN106800555B (zh) | 一种有机半导体主体材料及其有机发光二极管应用 | |
Yu et al. | Synthesis, metal complex formation, and electronic properties of a novel conjugate polymer with a tridentate 2, 6-bis (benzimidazol-2-yl) pyridine ligand | |
JP2010532555A (ja) | n−ドーパントの前駆物質の、有機半導体材料をドーピングするための使用、前駆物質ならびに電子素子または光電子素子 | |
KR20050042757A (ko) | 전자 활성 성분으로서 사용하기 위한2,1,3-벤조티아디아졸 | |
KR20120015354A (ko) | 유기 태양 전지에서 아릴 또는 헤트아릴 치환기를 갖는 프탈로시아닌 화합물의 용도 | |
TW200842140A (en) | Polymers comprising fused selenophene | |
CN106467548A (zh) | 一种含有苯并咪唑的化合物及其应用 | |
CN109791992B (zh) | 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 | |
Mikroyannidis et al. | Low band-gap phenylenevinylene and fluorenevinylene small molecules containing triphenylamine segments: Synthesis and application in bulk heterojunction solar cells | |
Lu et al. | Conjugated polymers containing sulfonic acid fluorene unit for achieving multiple interfacial modifications in fullerene-free organic solar cells | |
JP2020506897A (ja) | ヘテロ環化合物およびこれを含む有機電子素子 | |
KR102639497B1 (ko) | 헤테로환 화합물 및 이를 포함하는 유기 전자 소자 | |
KR102655911B1 (ko) | 헤테로환 화합물, 이를 포함하는 유기 전자 소자 및 이를 이용한 유기 전자 소자의 제조 방법 | |
KR101569854B1 (ko) | 벤조싸이아다이아졸 유도체 화합물, 이의 제조방법 및 이를 이용한 유기 태양전지 | |
KR20200004084A (ko) | 헤테로환 화합물, 이를 포함하는 조성물 및 이를 포함하는 유기 전자 소자 | |
WO2010019499A1 (en) | N-type conjugated compounds containing diborylene units, methods of making, and a device comprising the compound | |
JP2017507120A (ja) | フラーレン誘導体、これを用いた有機太陽電池及びこれの製造方法 | |
KR20190142948A (ko) | 중합체, 이를 포함하는 조성물 및 이를 포함하는 유기 태양 전지 | |
Gupta et al. | Triazine and Thiophene-Containing Conjugated Polymer Network Emitter-Based Solution-Processable Stable Blue Organic LEDs | |
KR102056515B1 (ko) | 조성물 및 이를 포함하는 유기전자소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant |