KR100594564B1 - 고분자 화합물, 화학 증폭 레지스트 재료 및 패턴 형성 방법 - Google Patents
고분자 화합물, 화학 증폭 레지스트 재료 및 패턴 형성 방법 Download PDFInfo
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- KR100594564B1 KR100594564B1 KR1020010007744A KR20010007744A KR100594564B1 KR 100594564 B1 KR100594564 B1 KR 100594564B1 KR 1020010007744 A KR1020010007744 A KR 1020010007744A KR 20010007744 A KR20010007744 A KR 20010007744A KR 100594564 B1 KR100594564 B1 KR 100594564B1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
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- QBOVXIMGMVOPQK-UHFFFAOYSA-N tert-butyl adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)OC(C)(C)C)C3 QBOVXIMGMVOPQK-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000233 ultraviolet lithography Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
-
- 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
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
-
- 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
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
중합체 | 투과율 248 nm (%) | 투과율 193 nm (%) | 투과율 157 nm (%) |
합성예 1 중합체 | 93 | 90 | 28 |
합성예 2 중합체 | 92 | 90 | 25 |
합성예 3 중합체 | 92 | 90 | 32 |
합성예 4 중합체 | 90 | 92 | 32 |
합성예 5 중합체 | 90 | 88 | 30 |
합성예 6 중합체 | 88 | 35 | 33 |
합성예 7 중합체 | 87 | 40 | 35 |
합성예 8 중합체 | 86 | 35 | 38 |
합성예 9 중합체 | 85 | 42 | 35 |
합성예 10 중합체 | 84 | 60 | 32 |
비교합성예 1 중합체 | 92 | 85 | 10 |
비교합성예 2 중합체 | 92 | 86 | 10 |
비교합성예 3 중합체 | 85 | 26 | 22 |
비교예 4 중합체 | 85 | 1 | 3 |
비교예 5 중합체 | 90 | 70 | 1 |
비교예 6 중합체 | 70 | 1 | 6 |
중합체 | CHF3/CF4계 가스 에칭 속도 (nm/분) | Cl2/BCl3계 가스 에칭 속도 (nm/분) |
합성예 1 중합체 | 95 | 115 |
합성예 2 중합체 | 92 | 110 |
합성예 3 중합체 | 93 | 112 |
합성예 4 중합체 | 110 | 125 |
합성예 5 중합체 | 116 | 128 |
합성예 6 중합체 | 96 | 116 |
합성예 7 중합체 | 93 | 112 |
합성예 8 중합체 | 95 | 110 |
합성예 9 중합체 | 110 | 120 |
합성예 10 중합체 | 112 | 122 |
비교합성예 1 중합체 | 96 | 115 |
비교합성예 2 중합체 | 90 | 105 |
비교합성예 3 중합체 | 97 | 117 |
비교예 4 중합체 | 90 | 103 |
비교예 5 중합체 | 180 | 350 |
비교예 6 중합체 | 88 | 100 |
중합체 | CHF3/CF4계 가스 에칭 후의 표면 조도 Rms (nm) |
합성예 1 중합체 | 3.3 |
합성예 2 중합체 | 3.0 |
합성예 3 중합체 | 2.8 |
합성예 4 중합체 | 3.5 |
합성예 5 중합체 | 6.6 |
합성예 6 중합체 | 3.1 |
합성예 7 중합체 | 2.9 |
합성예 8 중합체 | 2.6 |
비교합성예 1 중합체 | 3.2 |
비교합성예 2 중합체 | 10.8 |
비교합성예 3 중합체 | 3.6 |
비교예 4 중합체 | 2.2 |
비교예 5 중합체 | 20.5 |
비교예 6 중합체 | 1.5 |
중합체 (중량부) | 산발생제 (중량부) | 염기성 화합물 (중량부) | 용해 저지제 (중량부) | 용매 (중량부) | 감도 (mJ/cm2) | 해상도 (㎛) |
합성예 1 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 30 | 0.18 |
합성예 2 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 34 | 0.17 |
합성예 3 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 33 | 0.18 |
합성예 4 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 23 | 0.18 |
합성예 5 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 29 | 0.16 |
합성예 1 (100) | PAG1 (2) | 트리부틸아민 (0.1) | DRI (20) | PGMEA (800) | 33 | 0.18 |
합성예 1 (100) | PAG2 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 23 | 0.18 |
합성예 1 (100) | PAG1 (2) | 트리에탄올아민 (0.1) | - | PGMEA (800) | 35 | 0.17 |
합성예 1 (100) | PAG1 (2) | TMMEA (0.2) | - | PGMEA (800) | 35 | 0.17 |
비교합성예 1 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 30 | 0.18 |
비교합성예 2 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 25 | 0.16 |
중합체 (중량부) | 산발생제 (중량부) | 염기성 화합물 (중량부) | 용해 저지제 (중량부) | 용매 (중량부) | 감도 (mJ/cm2) | 해상도 (㎛) |
합성예 6 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 32 | 0.18 |
합성예 7 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 35 | 0.17 |
합성예 8 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 35 | 0.18 |
합성예 9 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 22 | 0.18 |
합성예 10 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 29 | 0.16 |
합성예 6 (100) | PAG1 (2) | 트리부틸아민 (0.1) | DRI (20) | PGMEA (800) | 30 | 0.18 |
합성예 6 (100) | PAG2 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 25 | 0.17 |
합성예 6 (100) | PAG1 (2) | 트리에탄올아민 (0.1) | - | PGMEA (800) | 38 | 0.17 |
합성예 6 (100) | PAG1 (2) | TMMEA (0.2) | - | PGMEA (800) | 40 | 0.17 |
비교합성예 3 (100) | PAG1 (2) | 트리부틸아민 (0.1) | - | PGMEA (800) | 45 | 0.18 |
Claims (13)
- 삭제
- 하기 화학식 1a 및 1b로 표시되는 반복 단위를 갖는 것을 특징으로 하는 고분자 화합물.<화학식 1a><화학식 1b>식 중,반복 단위 a는 단환, 복소환 또는 가교환식의 환상 탄화 수소 단위를 나타내고,Rp는 산불안정기 또는 친수성기를 포함하는 치환기이고,n은 0 내지 3의 정수이고,반복 단위 b는 불소화된 말레산 또는 말레이미드 단위를 나타내고,X는 산소 원자 또는 -NRq이며,Rq는 수소 원자, 탄소수 1 내지 10의 직쇄, 분지쇄 또는 환상 알킬기, 히드록실기, 카르복실기 또는 산불안정기를 포함하는 치환기이고,R1 및 R2는 수소 원자, 불소 원자, 또는 탄소수 1 내지 20의 직쇄, 분지쇄 또는 환상 알킬기 또는 불소화된 알킬기이고, R1 및 R2 중 적어도 1개는 불소 원자를 포함한다.
- 제2항 또는 제3항에 기재된 고분자 화합물을 포함하는 것을 특징으로 하는 화학 증폭 레지스트 재료.
- (A) 제2항 또는 제3항에 기재된 고분자 화합물,(B) 유기 용매, 및(C) 산발생제를 함유하는 것을 특징으로 하는 화학 증폭 포지형 레지스트 재료.
- 제5항에 있어서, 염기성 화합물을 더 함유하는 레지스트 재료.
- 제5항에 있어서, 용해 저지제를 더 함유하는 레지스트 재료.
- (1) 제4항에 기재된 레지스트 재료를 기판상에 도포하는 공정,(2) 이어서 가열 처리한 후, 포토마스크를 통하여 파장 300 nm 이하의 고에너지선 또는 전자선으로 노광하는 공정, 및(3) 가열 처리한 후, 현상액을 사용하여 현상하는 공정을 포함하는 것을 특징으로 하는 패턴 형성 방법.
- 제2항에 있어서, 상기 화학식 1b의 X가 산소 원자인 것을 특징으로 하는 고분자 화합물.
- 제9항 또는 제10 중 어느 한 항에 기재된 고분자 화합물을 포함하는 것을 특징으로 하는 화학 증폭 레지스트 재료.
- (A) 제9항 또는 제10항에 기재된 고분자 화합물,(B) 유기 용매, 및(C) 산발생제를 함유하는 것을 특징으로 하는 화학 증폭 포지형 레지스트 재료.
- 제12항에 있어서, 염기성 화합물을 더 함유하는 레지스트 재료.
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KR100389912B1 (ko) * | 1999-12-08 | 2003-07-04 | 삼성전자주식회사 | 지환식 감광성 폴리머 및 이를 포함하는 레지스트 조성물 |
KR100571453B1 (ko) * | 1999-12-15 | 2006-04-17 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 고분자 화합물, 화학 증폭 레지스트 재료 및 패턴 형성 방법 |
US6579658B2 (en) * | 2000-02-17 | 2003-06-17 | Shin-Etsu Chemical Co., Ltd. | Polymers, resist compositions and patterning process |
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Also Published As
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TWI237737B (en) | 2005-08-11 |
US6579658B2 (en) | 2003-06-17 |
US20010038969A1 (en) | 2001-11-08 |
KR20010088338A (ko) | 2001-09-26 |
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