WO2002099531A2 - ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS - Google Patents
ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS Download PDFInfo
- Publication number
- WO2002099531A2 WO2002099531A2 PCT/US2002/015694 US0215694W WO02099531A2 WO 2002099531 A2 WO2002099531 A2 WO 2002099531A2 US 0215694 W US0215694 W US 0215694W WO 02099531 A2 WO02099531 A2 WO 02099531A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- light attenuating
- recurring monomers
- attenuating compound
- layer
- Prior art date
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S438/00—Semiconductor device manufacturing: process
- Y10S438/942—Masking
- Y10S438/948—Radiation resist
- Y10S438/952—Utilizing antireflective layer
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31525—Next to glass or quartz
Definitions
- the present invention is concerned with anti-reflective coatings including polymers comprising unreacted epoxide groups, and methods of using those coatings with low dielectric constant materials to inhibit or avoid via or photoresist poisoning normally associated with those materials.
- the dual damascene process is a multi-level interconnection process in which, in addition to forming the grooves of the single damascene process, conductive contact or via holes are formed as well.
- circuit performance increasingly becomes a function of delay time of electronic signals traveling between the millions of gates and transistors present on an integrated circuit chip.
- the integrated circuit R-C delay that determines device switching speeds was dominated by the CMOS transistor drive capacitance and load resistance.
- the increase in signal delay due to capacitance of multilayer devices has become a limitation to improving device performance.
- a typical dual damascene process involves optical lithography techniques. In processes using a low dielectric constant material, the process would involve successively applying a barrier layer, a low dielectric constant layer, a hard mask layer, and an anti-reflective layer on a semiconductor substrate.
- the anti-reflective layer and low dielectric constant layer are patterned by photolithography with a photoresist layer to create openings or trenches.
- a photoresist layer to create openings or trenches.
- via or photoresist poisoning which occurs as a result of the low k dielectric material lying beneath the organic anti-reflective material has hindered the removal of the photoresist from the openings in the anti-reflective material.
- this opening is critical to the subsequent steps of forming multilayer interconnects, the inability to clear the photoresist interferes with quality device fabrication.
- the present invention overcomes the problems associated with via or photoresist poisoning by providing anti-reflective coating compositions which inhibit and/or block this poisoning. More detail, comprise light attenuating compounds or chromophores which can be physically mixed in the composition, reacted with some of the epoxide rings present in the polymer(s) of the composition, and/or otherwise bonded with some or all of the polymers present in the composition, so long as the compositions comprise unreacted or intact epoxide rings in the previously recited quantities.
- the compositions include a polymer which comprises: recurring monomers comprising an epoxide ring reacted with a light attenuating compound so as to open the epoxide ring (e.g., one of the carbon atoms of the ring has bonded with an atom of the light attenuating compound); and recurring monomers comprising unreacted epoxide rings (i.e., closed or intact epoxide rings).
- the molar ratio of unreacted epoxide rings present in the composition to reacted epoxide rings present in the composition is preferably from about 10:90 to about 90: 10, more preferably from about 20:80 to about 80:20, and even more preferably from about 20:80 to about 50:50. These ratios are essentially the same in the cured composition as well.
- the average molecular weight of the polymer(s) is generally from about 1,000-15,000 Daltons, and more preferably from about 3,000-5,000 Daltons. a particularly preferred embodiment, the polymer comprises recurring monomers selected from the group consisting of
- R comprises a light attenuating compound
- Preferred light attenuating compounds comprise a moiety selected from the group consisting of carboxylic acids, phenols, and amines, with a particularly preferred light attenuating compound being 9-anthracene carboxylic acid.
- the polymers are preferably prepared by partially grafting an epoxy resin (or other polymer in applications where the light attenuating compound is not bonded with the epoxide moieties) with the light attenuating compound.
- an epoxy resin or other polymer in applications where the light attenuating compound is not bonded with the epoxide moieties
- the resulting polymers can then be used to prepare the anti-reflective compositions by dissolving or dispersing the polymers in a suitable solvent system. In applications where part or all of the light attenuating compound is physically mixed with the polymer(s), the light attenuating compound is also dissolved or dispersed in the solvent system.
- the solvent system should have a boiling point of from about 100- 180 ° C, and preferably from about 120-150°C.
- the amount of polymer dissolved in the solvent system is preferably from about 2-15% by weight polymer, and more preferably from about 3-7%) by weight polymer, based upon the total weight of the composition taken as 100% by weight.
- the solvent system should be utilized at a level of from about 85- 98%o by weight, and more preferably from about 93-97%> by weight, based upon the total weight of the composition taken as 100% by weight.
- Preferred solvent systems include a solvent selected from the group consisting of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate, propylene glycol n-propyl ether, and mixtures thereof.
- a solvent selected from the group consisting of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate, propylene glycol n-propyl ether, and mixtures thereof.
- the inventive compositions can further include a crosslinking agent.
- a crosslinking agent separate from the polymer or, alternately, the polymer can include "built-in" crosslinking moieties.
- Preferred crosslinking agents include those selected from the group consisting of melamine and glycouril crosslinking agents.
- the crosslinking agent or moieties should be present in the composition at a level of from about 0.2-5% by weight, and preferably from about 0.5-1% by weight, based upon the total weight of all ingredients in the composition taken as 100%> by weight.
- the anti-reflective compositions should cross-link at a temperature of from about 85-250°C, and more preferably from about 100-220°C. It will be appreciated that numerous other optional compounds can be incorporated into the inventive anti-reflective or fill compositions if desired. Such other optional ingredients include 4,4'-sulfonyl diphonol and pyridinium tosylate.
- the anti-reflective coatings are applied according to conventional processes (e.g., spincoating), and can be used in conjunction with any low k (less than about 3.8) dielectric material including fluorinated silicate glass, amorphous-fluorinated carbon, fluorinated polyimides, fluorinated polyarylene ethers, and parylene-F.
- any low k (less than about 3.8) dielectric material including fluorinated silicate glass, amorphous-fluorinated carbon, fluorinated polyimides, fluorinated polyarylene ethers, and parylene-F.
- Fig. 2 is an SEM photograph (40X) depicting the photoresist layers of test wafers including anti-reflective coatings according to the invention.
- Scheme A depicts the reaction which occurred during this part of the example.
- An anti-reflective coating was prepared by mixing 12.0 g of the grafted polymer solution prepared in part 2 of this example with 17.9 g of PGMEA, 32.14 g of PGME, 0.0116 g of 7-toluenesulfonic acid, and 0.143 g of 4,4-sulfonyl diphenol. The ingredients were mixed until all of the solids were dissolved, followed by filtering of the mixture through a 0.1 ⁇ m filter.
- the filtered formulation was then spin-coated onto a silicon wafer at 2500 rpm for 60 seconds followed by baking on a hotplate at 205 °C for 60 seconds.
- the cured film had a thickness of 195 A and an optical density of 9.10/ ⁇ m.
- the anti-reflective composition prepared in Example 1 above was tested on wafers containing LCF pattern (refers to a pattern printed in reverse tone on the wafer scribbling), combination (trench and space pattern with vias under the trenches), stacked contact, and SEM bar features.
- An organosilicate dielectric material was applied to the wafers.
- the anti-reflective composition was coated onto the resulting low k dielectric layer (with vias patterned in it) by spincoating the anti-reflective composition at 500 rpm for 60 seconds followed by a 500 rpm final spin out and baking at 185°C for 90 seconds.
- a photoresist composition PEK-131, obtained from Sumitomo
- a second group of wafers was prepared by the same preparation procedure as described above except that these wafers were also subjected to a 440 °C passivation bake for 90 seconds prior to the application of the anti-reflective coating. Also, a control set of wafers using a prior art anti-reflective coating (RH2213-22-5 for conventional 248 nm BARC applications, Brewer Science, Inc.) was also tested.
- a prior art anti-reflective coating RH2213-22-5 for conventional 248 nm BARC applications, Brewer Science, Inc.
- Fig. 1 depicts SEM photographs of the photoresist layer after exposure of test samples utilizing an anti-reflective coating according to the invention.
- Fig. 2 shows the SEM photographs of the photoresist layer of the control sample.
- a comparison of the photographs shows that using an anti-reflective coating according to the invention blocked the via poisoning, thus allowing for the substantially complete removal of the photoresist material from the holes and trenches (see Fig. 1) unlike the control samples (see Fig. 2) which had photoresist material remaining in the holes and trenches.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2003-7015928A KR20040030651A (en) | 2001-06-05 | 2002-05-14 | ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS |
AU2002259251A AU2002259251A1 (en) | 2001-06-05 | 2002-05-14 | Anti-reflective coating compositions for use with low k dielectric materials |
JP2003502584A JP2004538625A (en) | 2001-06-05 | 2002-05-14 | Anti-reflective coating composition for low dielectric constant (lowk) dielectric material |
EP20020729246 EP1446700A2 (en) | 2001-06-05 | 2002-05-14 | ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/874,783 | 2001-06-05 | ||
US09/874,783 US6670425B2 (en) | 2001-06-05 | 2001-06-05 | Anti-reflective coating of polymer with epoxide rings reacted with light attenuating compound and unreacted epoxide rings |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002099531A2 true WO2002099531A2 (en) | 2002-12-12 |
WO2002099531A3 WO2002099531A3 (en) | 2004-06-17 |
Family
ID=25364567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/015694 WO2002099531A2 (en) | 2001-06-05 | 2002-05-14 | ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS |
Country Status (6)
Country | Link |
---|---|
US (2) | US6670425B2 (en) |
EP (1) | EP1446700A2 (en) |
JP (1) | JP2004538625A (en) |
KR (1) | KR20040030651A (en) |
AU (1) | AU2002259251A1 (en) |
WO (1) | WO2002099531A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005038878A2 (en) | 2003-10-15 | 2005-04-28 | Brewer Science Inc. | Developer-soluble materials and methods of using the same in via-first dual damascene applications |
EP1567288A2 (en) * | 2002-12-03 | 2005-08-31 | Brewer Science, Inc. | ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6846612B2 (en) * | 2002-02-01 | 2005-01-25 | Brewer Science Inc. | Organic anti-reflective coating compositions for advanced microlithography |
US7323289B2 (en) * | 2002-10-08 | 2008-01-29 | Brewer Science Inc. | Bottom anti-reflective coatings derived from small core molecules with multiple epoxy moieties |
JP2004153073A (en) * | 2002-10-31 | 2004-05-27 | Renesas Technology Corp | Manufacture of semiconductor device |
US6933227B2 (en) | 2003-10-23 | 2005-08-23 | Freescale Semiconductor, Inc. | Semiconductor device and method of forming the same |
US7030201B2 (en) * | 2003-11-26 | 2006-04-18 | Az Electronic Materials Usa Corp. | Bottom antireflective coatings |
US8249853B2 (en) * | 2006-03-31 | 2012-08-21 | Intel Corporation | Exposing device features in partitioned environment |
US7833692B2 (en) * | 2007-03-12 | 2010-11-16 | Brewer Science Inc. | Amine-arresting additives for materials used in photolithographic processes |
US20090035704A1 (en) | 2007-08-03 | 2009-02-05 | Hong Zhuang | Underlayer Coating Composition Based on a Crosslinkable Polymer |
US8039201B2 (en) * | 2007-11-21 | 2011-10-18 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
US20100015550A1 (en) * | 2008-07-17 | 2010-01-21 | Weihong Liu | Dual damascene via filling composition |
JP2013060477A (en) * | 2010-01-27 | 2013-04-04 | Nissan Chem Ind Ltd | Composition for formation of insulating film, and insulating film |
JP6449145B2 (en) | 2012-04-23 | 2019-01-09 | ブルーワー サイエンス アイ エヌ シー. | Photosensitive, developer-soluble bottom antireflection film material |
US10698317B2 (en) * | 2018-02-23 | 2020-06-30 | Taiwan Semiconductor Manufacturing Co., Ltd. | Underlayer material for photoresist |
Citations (6)
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SU1682362A1 (en) * | 1989-08-21 | 1991-10-07 | Предприятие П/Я Г-4430 | Copolymers of 1,4-naphthoquinine and epoxy-dianic resin as a binder for thermostable materials in electric insulation and a method for preparation of theirs |
JPH05283560A (en) * | 1991-10-04 | 1993-10-29 | Nitto Denko Corp | Semiconductor sealing epoxy resin composition and semiconductor device using it |
EP0851300A1 (en) * | 1996-12-24 | 1998-07-01 | Fuji Photo Film Co., Ltd. | Bottom anti-reflective coating material composition and method of forming resist pattern using the same |
US5919598A (en) * | 1995-08-21 | 1999-07-06 | Brewer Science, Inc. | Method for making multilayer resist structures with thermosetting anti-reflective coatings |
WO2001015211A1 (en) * | 1999-08-26 | 2001-03-01 | Brewer Science | Improved fill material for dual damascene processes |
US6306459B1 (en) * | 1999-06-17 | 2001-10-23 | 3M Innovative Properties Company | Retroflective article having a colored layer containing reflective flakes and a dye covalently bonded to a polymer |
Family Cites Families (4)
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US5597868A (en) | 1994-03-04 | 1997-01-28 | Massachusetts Institute Of Technology | Polymeric anti-reflective compounds |
US6103456A (en) | 1998-07-22 | 2000-08-15 | Siemens Aktiengesellschaft | Prevention of photoresist poisoning from dielectric antireflective coating in semiconductor fabrication |
KR100465864B1 (en) | 1999-03-15 | 2005-01-24 | 주식회사 하이닉스반도체 | Organic anti-reflective polymer and method for manufacturing thereof |
KR100310252B1 (en) | 1999-06-22 | 2001-11-14 | 박종섭 | Organic anti-reflective polymer and method for manufacturing thereof |
-
2001
- 2001-06-05 US US09/874,783 patent/US6670425B2/en not_active Expired - Lifetime
-
2002
- 2002-05-14 JP JP2003502584A patent/JP2004538625A/en active Pending
- 2002-05-14 KR KR10-2003-7015928A patent/KR20040030651A/en not_active Application Discontinuation
- 2002-05-14 WO PCT/US2002/015694 patent/WO2002099531A2/en not_active Application Discontinuation
- 2002-05-14 AU AU2002259251A patent/AU2002259251A1/en not_active Abandoned
- 2002-05-14 EP EP20020729246 patent/EP1446700A2/en not_active Withdrawn
- 2002-06-18 US US10/174,173 patent/US6663916B2/en not_active Expired - Lifetime
Patent Citations (6)
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SU1682362A1 (en) * | 1989-08-21 | 1991-10-07 | Предприятие П/Я Г-4430 | Copolymers of 1,4-naphthoquinine and epoxy-dianic resin as a binder for thermostable materials in electric insulation and a method for preparation of theirs |
JPH05283560A (en) * | 1991-10-04 | 1993-10-29 | Nitto Denko Corp | Semiconductor sealing epoxy resin composition and semiconductor device using it |
US5919598A (en) * | 1995-08-21 | 1999-07-06 | Brewer Science, Inc. | Method for making multilayer resist structures with thermosetting anti-reflective coatings |
EP0851300A1 (en) * | 1996-12-24 | 1998-07-01 | Fuji Photo Film Co., Ltd. | Bottom anti-reflective coating material composition and method of forming resist pattern using the same |
US6306459B1 (en) * | 1999-06-17 | 2001-10-23 | 3M Innovative Properties Company | Retroflective article having a colored layer containing reflective flakes and a dye covalently bonded to a polymer |
WO2001015211A1 (en) * | 1999-08-26 | 2001-03-01 | Brewer Science | Improved fill material for dual damascene processes |
Non-Patent Citations (1)
Title |
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DATABASE CAPLUS [Online] COLUMBUS OHIO, USA KAL'YAN ET AL.: 'Protective action of complexing polymers containing hydroxyquinoline groups in neutral media', XP002954787 Database accession no. 1973:480423 & TR., KISHINEV. POLITEKH. INST. no. 24, 1971, pages 97 - 104 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1567288A2 (en) * | 2002-12-03 | 2005-08-31 | Brewer Science, Inc. | ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS |
EP1567288A4 (en) * | 2002-12-03 | 2006-06-07 | Brewer Science Inc | ANTI-REFLECTIVE COATING COMPOSITIONS FOR USE WITH LOW k DIELECTRIC MATERIALS |
WO2005038878A2 (en) | 2003-10-15 | 2005-04-28 | Brewer Science Inc. | Developer-soluble materials and methods of using the same in via-first dual damascene applications |
EP1673801A2 (en) * | 2003-10-15 | 2006-06-28 | Brewer Science, Inc. | Developer-soluble materials and methods of using the same in via-first dual damascene applications |
EP1673801A4 (en) * | 2003-10-15 | 2010-04-07 | Brewer Science Inc | Developer-soluble materials and methods of using the same in via-first dual damascene applications |
Also Published As
Publication number | Publication date |
---|---|
US6663916B2 (en) | 2003-12-16 |
US20030004283A1 (en) | 2003-01-02 |
JP2004538625A (en) | 2004-12-24 |
WO2002099531A3 (en) | 2004-06-17 |
KR20040030651A (en) | 2004-04-09 |
US6670425B2 (en) | 2003-12-30 |
US20020198333A1 (en) | 2002-12-26 |
EP1446700A2 (en) | 2004-08-18 |
AU2002259251A1 (en) | 2002-12-16 |
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