KR101011841B1 - 트리아진 화합물을 포함하는 반사 방지 조성물 - Google Patents
트리아진 화합물을 포함하는 반사 방지 조성물 Download PDFInfo
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- KR101011841B1 KR101011841B1 KR1020057006597A KR20057006597A KR101011841B1 KR 101011841 B1 KR101011841 B1 KR 101011841B1 KR 1020057006597 A KR1020057006597 A KR 1020057006597A KR 20057006597 A KR20057006597 A KR 20057006597A KR 101011841 B1 KR101011841 B1 KR 101011841B1
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- KR
- South Korea
- Prior art keywords
- antireflective coating
- coating composition
- acid
- compound
- resin
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 106
- 230000003667 anti-reflective Effects 0.000 title abstract description 7
- 150000003918 triazines Chemical class 0.000 title description 4
- 239000006117 anti-reflective coating Substances 0.000 claims abstract description 121
- 229920005989 resin Polymers 0.000 claims abstract description 98
- 239000011347 resin Substances 0.000 claims abstract description 98
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 57
- -1 triazine compound Chemical class 0.000 claims abstract description 57
- 239000010410 layer Substances 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 20
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 13
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims abstract description 13
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- 238000005530 etching Methods 0.000 claims abstract description 8
- BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 26
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 14
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- 239000011247 coating layer Substances 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 6
- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 claims description 5
- 238000001459 lithography Methods 0.000 claims description 5
- 125000005577 anthracene group Chemical group 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims 2
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- 238000006243 chemical reaction Methods 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 5
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- 235000013772 propylene glycol Nutrition 0.000 description 5
- UIRWMICMOZDHAD-UHFFFAOYSA-N 2,2,2-tribromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(Br)(Br)Br UIRWMICMOZDHAD-UHFFFAOYSA-N 0.000 description 4
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- QMWOUSYSNFCKAZ-UHFFFAOYSA-N 3,7-DIHYDROXYNAPHTHALENE-2-CARBOXYLIC ACID Chemical compound OC1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 QMWOUSYSNFCKAZ-UHFFFAOYSA-N 0.000 description 3
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- 239000005711 Benzoic acid Substances 0.000 description 3
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- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- WSKHYOXDVZCOJP-UHFFFAOYSA-N naphthalene-1,6-diamine Chemical compound NC1=CC=CC2=CC(N)=CC=C21 WSKHYOXDVZCOJP-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 description 1
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- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N rac-1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
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- 229940035048 sorbitan monostearate Drugs 0.000 description 1
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- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015149 toffees Nutrition 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 229940029612 triethanolamine Drugs 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
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
- G03F7/09—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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon
Abstract
Description
반사 방지 코팅 조성물로서,
(A) 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나, 또는 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 트리아진 화합물로 이루어지고 중량 평균 분자량이 5000 이상인 수지와,
(B) 흡광 화합물 및 흡광 수지 중에서 어느 한 가지를 포함하거나, 또는 흡광 화합물 및 흡광 수지 두 가지를 모두 포함하는 반사 방지 코팅 조성물에 관한 것이다.
실시예 | 굴절율(n) | 광흡수인자(k) | 최초 최소 두께 (nm) | 식각 속도 | |
반사율(%) | 선택성 | ||||
1 | 1.78 | 0.51 | 42 | 0.04 | 1.3 |
2 | 1.82 | 0.53 | 40 | 0.03 | 1.3 |
3 | 1.84 | 0.53 | 39 | 0.04 | 1.4 |
4 | 1.86 | 0.56 | 38 | <0.01 | 1.4 |
5 | 1.91 | 0.58 | 35 | <0.01 | 1.5 |
6 | 1.97 | 0.60 | 33 | <0.01 | 1.5 |
7 | 1.88 | 0.56 | 37 | <0.01 | 1.6 |
8 | 1.93 | 0.58 | 35 | <0.01 | 1.6 |
9 | 1.74 | 0.53 | 45 | <0.01 | 1.3 |
10 | 1.79 | 0.55 | 41 | <0.01 | 1.3 |
비교예 1 | 1.50 | 0.48 | 57 | 0.19 | 1.3 |
Claims (18)
- 반사 방지 코팅 조성물로서,(A) 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나, 또는 상기 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 트리아진 화합물로 이루어지고 중량 평균 분자량이 5000 이상인 수지와,(B) 흡광 화합물 및 흡광 수지 중에서 어느 한 가지를 포함하거나, 또는 흡광 화합물 및 흡광 수지 두 가지를 모두 포함하며,상기 (A) 및 (B)의 성분은 용매에서 용해되는 반사 방지 코팅 조성물.
- 제 1 항에 있어서, 상기 트리아진 화합물은 멜라민 화합물 및 벤조구아나민 화합물로 구성되는 군에서 선택되는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항에 있어서, 상기 수지는 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나, 또는 상기 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 멜라민 화합물과, 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나 또는 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 벤조구아나민 화합물로 이루어지고 중량 평균 분자량이 5000-50000인 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항에 있어서, 상기 수지는 헥사메톡시메틸멜라민 및 테트라메톡시메틸 벤조구아나민으로 이루어지고, 중량 평균 분자량이 7000-30000인 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항 내지 제 4 항중 어느 한 항에 있어서, 상기 흡광 화합물이 나프탈렌 화합물 및 안트라센 화합물로 구성되는 군에서 선택되는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항 내지 제 4 항중 어느 한 항에 있어서, 상기 흡광 화합물이 9-히드록시메틸안트라센인 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 6 항에 있어서, 상기 흡광 수지가 벤젠 고리 구조, 나프탈렌 고리 구조, 및 안트라센 고리 구조로 구성되는 군에서 선택된 하나 이상의 고리 구조를 갖는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항 내지 제 4 항 중 어느 한 항에 있어서, 산 및 산 발생제 중에서 어느 한 가지, 또는 산 및 산 발생제 두 가지 모두를 추가로 함유하는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 8 항에 있어서, 상기 산은 지방족 카르복시산, 지방족 설폰산, 방향족 카르복시산, 및 방향족 설폰산으로 구성되는 군에서 선택된 하나 이상인 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항 내지 제 4 항 중 어느 한 항에 있어서, 단위체내에서 하나 이상의 가교가능한 치환체가 있는 단위 구조체를 갖는 수지를 추가로 함유하는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 1 항 내지 제 4 항 중 어느 한 항에 있어서, 상기 성분 (A)의 양은 성분 (A)와 (B)의 전체 중량을 기준으로 50 내지 99 중량%인 것을 특징으로 하는 반사 방지 코팅 조성물.
- 반도체 소자를 제조하기 위한 리소그래피 공정에서 사용하기 위한 반사 방지 코팅층을 형성하는 방법으로서, 상기 코팅층은 제 1 항 내지 제 4 항중 어느 한 항에 따른 반사 방지 코팅 조성물을 기판상에 도포하고 베이킹함으로써 얻어지는 것을 특징으로 하는 방법.
- 반도체 소자를 제조하는 방법으로서, 제 1 항 내지 제 4 항 중 어느 한 항에 따른 반사 방지 코팅 조성물을 기판상에 도포하고, 베이킹하여 반사 방지 코팅층을 형성하고, 상기 코팅층에 포토레지스트를 도포하고, 상기 반사 방지 코팅층이 도포된 기판을 노광하고, 식각하여 상기 기판상에 이미지를 현상 및 전사하여 집적 회로 소자를 제조하는 것을 포함하는 것을 특징으로 하는 방법.
- 반사 방지 코팅 조성물로서,(A) 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나, 또는 상기 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 다수의 트리아진 부분들로 이루어지고, 상기 다수의 트리아진 부분들은 -CH2- 연결기 및 -CH2-O-CH2- 연결기 중 어느 한 연결기를 통해 결합되거나, 또는 -CH2- 연결기 및 -CH2-O-CH2- 연결기 모두를 통해 결합되며, 중량 평균 분자량이 5000 이상인 수지와,(B) 흡광 화합물 및 흡광 수지 중에서 어느 한 가지를 포함하거나, 또는 흡광 화합물 및 흡광 수지 두 가지를 모두 포함하는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제14항에 있어서,상기 (A) 및 (B)의 성분은 용매에서 용해되는 것을 특징으로 하는 반사 방지 코팅 조성물
- 제 14 항에 있어서, 상기 트리아진 부분은 멜라민 화합물 및 벤조구아나민 화합물로 구성되는 군에서 선택되는 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 14 항에 있어서, 상기 수지는 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나 또는 상기 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 멜라민 화합물과 히드록시메틸기 및 알콕시메틸기 중에서 어느 한가지 기로 치환되거나 또는 두 가지 기 모두로 치환된 두 개 이상의 질소 원자를 갖는 벤조구아나민 화합물로 이루어지고 중량 평균 분자량이 5000-50000인 것을 특징으로 하는 반사 방지 코팅 조성물.
- 제 14 항에 있어서, 상기 수지는 헥사메톡시메틸멜라민 및 테트라메톡시메틸 벤조구아나민으로 이루어지고, 중량 평균 분자량이 7000-30000인 것을 특징으로 하는 반사 방지 코팅 조성물.
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US10/271,646 | 2002-10-15 | ||
US10/271,646 US7038328B2 (en) | 2002-10-15 | 2002-10-15 | Anti-reflective compositions comprising triazine compounds |
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EP (1) | EP1556896B1 (ko) |
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KR (1) | KR101011841B1 (ko) |
AT (1) | AT392011T (ko) |
AU (1) | AU2003278870A1 (ko) |
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JP2006503331A (ja) | 2006-01-26 |
DE60320292T2 (de) | 2009-07-16 |
US7038328B2 (en) | 2006-05-02 |
EP1556896A4 (en) | 2007-05-09 |
EP1556896B1 (en) | 2008-04-09 |
AT392011T (de) | 2008-04-15 |
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WO2004036311A2 (en) | 2004-04-29 |
US20040072420A1 (en) | 2004-04-15 |
TW200413839A (en) | 2004-08-01 |
TWI303013B (en) | 2008-11-11 |
KR20050074962A (ko) | 2005-07-19 |
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