KR100739952B1 - 막 형성용 조성물, 막의 형성 방법 및 실리카계 막 - Google Patents
막 형성용 조성물, 막의 형성 방법 및 실리카계 막 Download PDFInfo
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- KR100739952B1 KR100739952B1 KR1020010018551A KR20010018551A KR100739952B1 KR 100739952 B1 KR100739952 B1 KR 100739952B1 KR 1020010018551 A KR1020010018551 A KR 1020010018551A KR 20010018551 A KR20010018551 A KR 20010018551A KR 100739952 B1 KR100739952 B1 KR 100739952B1
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- SGZJOYFOVHWDFY-UHFFFAOYSA-N tri(butan-2-yloxy)-[3-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC([Si](OC(C)CC)(OC(C)CC)OC(C)CC)=C1 SGZJOYFOVHWDFY-UHFFFAOYSA-N 0.000 description 1
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- CQLAZINSWMHWAQ-UHFFFAOYSA-N tributoxy(dibutoxymethylsilylmethyl)silane Chemical compound CCCCOC(OCCCC)[SiH2]C[Si](OCCCC)(OCCCC)OCCCC CQLAZINSWMHWAQ-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- WAAWAIHPWOJHJJ-UHFFFAOYSA-N tributoxy(propyl)silane Chemical compound CCCCO[Si](CCC)(OCCCC)OCCCC WAAWAIHPWOJHJJ-UHFFFAOYSA-N 0.000 description 1
- MVXBTESZGSNIIB-UHFFFAOYSA-N tributoxy(tert-butyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(C)(C)C MVXBTESZGSNIIB-UHFFFAOYSA-N 0.000 description 1
- JXXQPVMVSMWLGZ-UHFFFAOYSA-N tributoxy(tributoxysilylmethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C[Si](OCCCC)(OCCCC)OCCCC JXXQPVMVSMWLGZ-UHFFFAOYSA-N 0.000 description 1
- ZYXLOEAJFSQDQG-UHFFFAOYSA-N tributoxy-(2-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1[Si](OCCCC)(OCCCC)OCCCC ZYXLOEAJFSQDQG-UHFFFAOYSA-N 0.000 description 1
- UYZUVKDKSJFNIN-UHFFFAOYSA-N tributoxy-(3-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC([Si](OCCCC)(OCCCC)OCCCC)=C1 UYZUVKDKSJFNIN-UHFFFAOYSA-N 0.000 description 1
- YBNXDKRALACDIA-UHFFFAOYSA-N tributoxy-(4-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=C([Si](OCCCC)(OCCCC)OCCCC)C=C1 YBNXDKRALACDIA-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-UHFFFAOYSA-N 0.000 description 1
- MUCRQDBOUNQJFE-UHFFFAOYSA-N triphenoxy(triphenoxysilyl)silane Chemical compound C=1C=CC=CC=1O[Si]([Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 MUCRQDBOUNQJFE-UHFFFAOYSA-N 0.000 description 1
- YRUALOZSEADDBR-UHFFFAOYSA-N triphenyl triphenoxysilyl silicate Chemical compound C=1C=CC=CC=1O[Si](O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 YRUALOZSEADDBR-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- BZIXIRYKSIMLOB-UHFFFAOYSA-N tripropoxy(tripropoxysilylmethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C[Si](OCCC)(OCCC)OCCC BZIXIRYKSIMLOB-UHFFFAOYSA-N 0.000 description 1
- FOUOZDXPXSKVEL-UHFFFAOYSA-N tripropoxy-(4-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=C([Si](OCCC)(OCCC)OCCC)C=C1 FOUOZDXPXSKVEL-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- GBGOZMPAPWGNGR-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]ethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)CC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C GBGOZMPAPWGNGR-UHFFFAOYSA-N 0.000 description 1
- NNKMRNUOGTXRCM-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[3-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)=C1 NNKMRNUOGTXRCM-UHFFFAOYSA-N 0.000 description 1
- PITXUFPLSLHXRV-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[4-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=C([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)C=C1 PITXUFPLSLHXRV-UHFFFAOYSA-N 0.000 description 1
- QJJZQRNPNLTSNS-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[tris[(2-methylpropan-2-yl)oxy]silylmethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C QJJZQRNPNLTSNS-UHFFFAOYSA-N 0.000 description 1
- KGOOITCIBGXHJO-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-phenylsilane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1 KGOOITCIBGXHJO-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- QCKKBOHAYRLMQP-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[SiH](OC(C)(C)C)OC(C)(C)C QCKKBOHAYRLMQP-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- 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
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Abstract
본 발명은 (A) 하기 화학식 1로 표시되는 화합물, 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물 군에서 선택되는 1종 이상의 실란 화합물을 수산화테트라알킬암모늄, 지방족 환상 유기 아민, 금속 수산화물 군에서 선택되는 1종 이상의 화합물과 물의 존재하에서 가수분해하고, 축합한 가수분해 축합물 및 (B) 유기 용매를 함유하는 것을 특징으로 하는 막 형성용 조성물을 제공한다.
<화학식 1>
RaSi(OR1)4-a
식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기, R1은 1가의 유기기, a는 1 내지 2의 정수를 나타낸다.
<화학식 2>
Si(OR2)4
식 중, R2는 1가의 유기기를 나타낸다.
<화학식 3>
R3
b(R4O)3-bSi-(R7)d-Si(OR5)
3-cR6
c
식 중, R3 내지 R6은 동일하거나 또는 상이하며 각각 1가의 유기기를 나타내고, b 및 c는 동일하거나 또는 상이하며 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)n-으로 표시되는 기 (여기에서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
실리카계 막, 막 형성용 조성물, 절연막
Description
본 발명은 막 형성용 조성물에 관한 것으로, 더욱 상세하게는 반도체 소자 등에서의 층간 절연막 재료로서 PCT(Presure Cooker Test) 후의 비유전율 특성, PCT 후의 CMP(Chemical Mechanical Polishing) 내성, PCT 후의 기판과의 밀착성이 우수한 실리카계 막을 형성할 수 있는 막 형성용 조성물에 관한 것이다.
종래부터, 반도체 소자 등에서의 층간 절연막으로서, CVD법 등의 진공 공정으로 형성된 실리카(SiO2)막이 많이 사용되고 있다. 그리고, 최근 보다 균일한 층간 절연막을 형성하는 것을 목적으로 SOG(Spin on Glass)막이라고 불리는 테트라알콕시실란의 가수분해 생성물을 주성분으로 하는 도포형 절연막도 사용되고 있다. 또한, 반도체 소자 등의 고집적화에 따라 유기 SOG라고 불리는 폴리오르가노실록산을 주성분으로 하는 저비유전율의 층간 절연막이 개발되고 있다.
특히, 반도체 소자 등의 고집적화 및 다층화가 계속됨에 따라, 보다 우수한 도체 간의 전기 절연성이 요구되고 있으며, 따라서 보다 저비유전율의 균열 내성이 우수한 층간 절연막 재료가 요구되고 있다.
저비유전율 재료로서는, 암모니아 존재하에 알콕시실란을 축합하여 얻어지는 미립자와 알콕시실란의 염기성 부분 가수분해물과의 혼합물로 이루어지는 조성물 (일본 특개평 5-263045, 5-315319) 및 폴리알콕시실란의 염기성 가수분해물을 암모니아 존재하에 축합함으로써 얻어진 도포액 (일본 특개평 11-340219, 11-340220)이 제안되어 있지만, 이들 방법으로 얻어지는 재료는 반응 생성물의 성질이 안정되어 있지 않고, PCT 후의 비유전율 특성, PCT 후의 CMP 내성, PCT 후의 기판과의 밀착성 등의 막 특성 변동도 크기 때문에 공업적 생산에는 부적합하였다.
본 발명은 상기 문제점을 해결하기 위한 막 형성용 조성물에 관한 것으로, 더욱 상세하게는 반도체 소자 등에서의 층간 절연막으로서 PCT 후의 비유전율 특성, PCT 후의 CMP 내성, PCT 후의 기판과의 밀착성이 우수한 막 형성용 조성물 및 이 조성물로부터 얻어지는 실리카계 막을 제공하는 것을 목적으로 한다.
본 발명은,
(A) 하기 화학식 1로 표시되는 화합물 (이하, "화합물 (1)"이라고 함), 하기 화학식 2로 표시되는 화합물 (이하, "화합물 (2)"라고 함) 및 하기 화학식 3으로 표시되는 화합물 (이하, "화합물 (3)"이라고 함)의 군에서 선택된 1종 이상의 실란 화합물을 수산화테트라알킬암모늄, 지방족 환상 유기 아민, 금속 수산화물의 군에서 선택되는 1종 이상의 화합물 (이하, "특정 염기성 화합물"이라고 함)과 물의 존 재하에서 가수분해하고, 축합한 가수분해 축합물 및
(B) 유기 용매를 함유하는 것을 특징으로 하는 막 형성용 조성물에 관한 것이다.
식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이며, a는 1 내지 2의 정수를 나타낸다.
식 중, R2는 1가의 유기기를 나타낸다.
식 중, R3 내지 R6은 동일하거나 또는 상이하며 각각 1가의 유기기를 나타내고, b 및 c는 동일하거나 또는 상이하며 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)n-으로 표시되는 기 (여기에서, n은 1 내지 6의 정수임)이고, d는 0 또는 1을 나타낸다.
이어서, 본 발명은 상기 막 형성용 조성물을 기판에 도포하고, 가열하는 것을 특징으로 하는 막 형성 방법에 관한 것이다.
이어서, 본 발명은 상기 막 형성 방법에 의해 얻어지는 실리카계 막에 관한 것이다.
본 발명에 있어서, (A) 가수분해 축합물이란, 상기 화합물 (1) 내지 (3)의 군에서 선택된 1종 이상의 가수분해물 및 그의 축합물 또는 그 중 어느 하나이다.
여기에서, (A) 성분에서의 가수분해물이란, 상기 (A)성분을 구성하는 화합물 (1) 내지 (3)에 포함되는 R1O-기, R2O-기, R4O-기 및 R5O-기 모두가 가수분해될 필요는 없으며, 예를 들면 1개만이 가수분해되어 있는 것, 2개 이상이 가수분해되어 있는 것, 또는 이들의 혼합물일 수도 있다.
또한, (A) 성분에서의 축합물은, (A) 성분을 구성하는 화합물 (1) 내지 (3)의 가수분해물의 실란올기가 축합하여 Si-O-Si 결합을 형성한 것이지만, 본 발명에서는 실란올기가 모두 축합될 필요는 없으며 약간 일부의 실란올이 축합된 것, 축합 정도가 다른 것의 혼합물 등도 포함한 개념이다.
(A) 가수분해 축합물
(A) 가수분해 축합물은 상기 화합물 (1) 내지 (3)의 군에서 선택된 1종 이상의 실란 화합물을 특정 염기성 화합물 존재하에서 가수분해, 축합하여 얻어진다.
화합물 (1);
상기 화학식 1에 있어서, R 및 R1의 1가의 유기기로서는 알킬기, 아릴기, 알 릴기, 글리시딜기 등을 들 수 있다. 또한, 화학식 1에 있어서, R은 1가의 유기기, 특히 알킬기 또는 페닐기인 것이 바람직하다.
여기에서, 알킬기로서는 메틸기, 에틸기, 프로필기, 부틸기 등을 들 수 있으며, 바람직하게는 탄소수 1 내지 5이고, 이들 알킬기는 쇄상일 수도, 분지될 수도, 또는 수소 원자가 불소 원자 등에 치환될 수도 있다.
화학식 1에 있어서, 아릴기로서는 페닐기, 나프틸기, 메틸페닐기, 에틸페닐기, 클로로페닐기, 브로모페닐기, 플루오로페닐기 등을 들 수 있다.
화학식 1로 표시되는 화합물의 구체예로서는, 트리메톡시실란, 트리에톡시실란, 트리-n-프로폭시실란, 트리-iso-프로폭시실란, 트리-n-부톡시실란, 트리-sec-부톡시실란, 트리-tert-부톡시실란, 트리페녹시실란, 플루오로 트리메톡시실란, 플루오로 트리에톡시실란, 플루오로 트리-n-프로폭시실란, 플루오로 트리-iso-프로폭시실란, 플루오로 트리-n-부톡시실란, 플루오로 트리-sec-부톡시실란, 플루오로 트리-tert-부톡시실란, 플루오로트리페녹시실란 등;
메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-iso-프로폭시실란, 메틸트리-n-부톡시실란, 메틸트리-sec-부톡시실란, 메틸트리 -tert-부톡시실란, 메틸트리페녹시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 에틸트리-n-프로폭시실란, 에틸트리-iso-프로폭시실란, 에틸트리-n-부톡시실란, 에틸트리-sec-부톡시실란, 에틸트리-tert-부톡시실란, 에틸트리페녹시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리-n-프로폭시실란, 비닐트리-iso-프로폭시실란, 비닐트리-n-부톡시실란, 비닐트리-sec-부톡시실란, 비닐트리-tert-부톡시 실란, 비닐트리페녹시실란, n-프로필트리메톡시실란, n-프로필트리에톡시실란, n-프로필트리-n-프로폭시실란, n-프로필트리-iso-프로폭시실란, n-프로필트리-n-부톡시실란, n-프로필트리-sec-부톡시실란, n-프로필트리-tert-부톡시실란, n-프로필트리페녹시실란, i-프로필트리메톡시실란, i-프로필트리에톡시실란, i-프로필트리-n-프로폭시실란, i-프로필트리-iso-프로폭시실란, i-프로필트리-n-부톡시실란, i-프로필트리-sec-부톡시실란, i-프로필트리-tert-부톡시실란, i-프로필트리페녹시실란, n-부틸트리메톡시실란, n-부틸트리에톡시실란, n-부틸트리-n-프로폭시실란, n-부틸트리-iso-프로폭시실란, n-부틸트리-n-부톡시실란, n-부틸트리-sec-부톡시실란, n-부틸트리-tert-부톡시실란, n-부틸트리페녹시실란, sec-부틸트리메톡시실란, sec-부틸트리에톡시실란, sec-부틸-트리-n-프로폭시실란, sec-부틸-트리-iso-프로폭시실란, sec-부틸-트리-n-부톡시실란, sec-부틸-트리-sec-부톡시실란, sec-부틸-트리-tert-부톡시실란, sec-부틸-트리페녹시실란, t-부틸트리메톡시실란, t-부틸트리에톡시실란, t-부틸트리-n-프로폭시실란, t-부틸트리-iso-프로폭시실란, t-부틸트리-n-부톡시실란, t-부틸트리-sec-부톡시실란, t-부틸트리-tert-부톡시실란, t-부틸트리페녹시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 페닐트리-n-프로폭시실란, 페닐트리-iso-프로폭시실란, 페닐트리-n-부톡시실란, 페닐트리-sec-부톡시실란, 페닐트리-tert-부톡시실란, 페닐트리페녹시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, γ-아미노프로필트리메톡시실란, γ-아미노프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, γ-글리시독시프로필트리에톡시실란, γ-트리플로로프로필트리메톡시실란, γ-트리플로로프로필트리에톡시실란 등;
디메틸디메톡시실란, 디메틸디에톡시실란, 디메틸-디-n-프로폭시실란, 디메틸-디-iso-프로폭시실란, 디메틸-디-n-부톡시실란, 디메틸-디-sec-부톡시실란, 디메틸-디-tert-부톡시실란, 디메틸디페녹시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디에틸-디-n-프로폭시실란, 디에틸-디-iso-프로폭시실란, 디에틸-디-n-부톡시실란, 디에틸-디-sec-부톡시실란, 디에틸-디-tert-부톡시실란, 디에틸디페녹시실란, 디-n-프로필디메톡시실란, 디-n-프로필디에톡시실란, 디-n-프로필-디-n-프로폭시실란, 디-n-프로필-디-iso-프로폭시실란, 디-n-프로필-디-n-부톡시실란, 디-n-프로필-디-sec-부톡시실란, 디-n-프로필-디-tert-부톡시실란, 디-n-프로필-디-페녹시실란, 디-iso-프로필디메톡시실란, 디-iso-프로필디에톡시실란, 디-iso-프로필-디-n-프로폭시실란, 디-iso-프로필-디-iso-프로폭시실란, 디-iso-프로필-디-n-부톡시실란, 디-iso-프로필-디-sec-부톡시실란, 디-iso-프로필-디-tert-부톡시실란, 디-iso-프로필-디-페녹시실란, 디-n-부틸디메톡시실란, 디-n-부틸디에톡시실란, 디-n-부틸-디-n-프로폭시실란, 디-n-부틸-디-iso-프로폭시실란, 디-n-부틸-디-n-부톡시실란, 디-n-부틸-디-sec-부톡시실란, 디-n-부틸-디-tert-부톡시실란, 디-n-부틸-디-페녹시실란, 디-sec-부틸디메톡시실란, 디-sec-부틸디에톡시실란, 디-sec-부틸-디-n-프로폭시실란, 디-sec-부틸-디-iso-프로폭시실란, 디-sec-부틸-디-n-부톡시실란, 디-sec-부틸-디-sec-부톡시실란, 디-sec-부틸-디-tert-부톡시실란, 디-sec-부틸-디-페녹시실란, 디-tert-부틸디메톡시실란, 디-tert-부틸디에톡시실란, 디-tert-부틸-디-n-프로폭시실란, 디-tert-부틸-디-iso-프로폭시실란, 디-tert-부틸-디-n-부톡시실란, 디-tert-부틸-디-sec-부톡시실란, 디-tert-부틸-디-tert-부톡 시실란, 디-tert-부틸-디-페녹시실란, 디페닐디메톡시실란, 디페닐-디-에톡시실란, 디페닐-디-n-프로폭시실란, 디페닐-디-iso-프로폭시실란, 디페닐-디-n-부톡시실란, 디페닐-디-sec-부톡시실란, 디페닐-디-tert-부톡시실란, 디페닐디페녹시실란, 디비닐트리메톡시실란 등을 들 수 있다.
화합물 (1)로서 바람직한 화합물은, 메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-iso-프로폭시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 디메틸디메톡시실란, 디메틸디에톡시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디페닐디메톡시실란, 디페닐디에톡시실란 등이다.
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
화합물 (2);
상기 화학식 2에 있어서, R2로 표시되는 1가의 유기기로서는 상기 화학식 1과 동일한 유기기를 들 수 있다.
화학식 2로 표시되는 화합물의 구체예로서는, 테트라메톡시실란, 테트라에톡시실란, 테트라-n-프로폭시실란, 테트라-iso-프로폭시실란, 테트라-n-부톡시실란, 테트라-sec-부톡시실란, 테트라-tert-부톡시실란, 테트라페녹시실란 등을 들 수 있다.
화합물 (3);
상기 화학식 3에 있어서, R3 내지 R6으로 표시되는 1가의 유기기로서는, 상기 화학식 1과 동일한 유기기를 들 수 있다.
화학식 3 중, R7이 산소 원자인 화합물로서는, 헥사메톡시디실록산, 헥사에톡시디실록산, 헥사페녹시디실록산, 1,1,1,3,3-펜타메톡시-3-메틸디실록산, 1,1,1, 3,3-펜타에톡시-3-메틸디실록산, 1,1,1,3,3-펜타페녹시-3-메틸디실록산, 1,1,1,3, 3-펜타메톡시-3-에틸디실록산, 1,1,1,3,3-펜타에톡시-3-에틸디실록산, 1,1,1,3,3-펜타페녹시-3-에틸디실록산, 1,1,1,3,3-펜타메톡시-3-페닐디실록산 1,1,1,3,3-펜타에톡시-3-페닐디실록산, 1,1,1,3,3-펜타페녹시-3-페닐디실록산, 1,1,3,3-테트라메톡시-1,3-디메틸디실록산, 1,1,3,3-테트라에톡시-1,3-디메틸디실록산, 1,1,3,3-테트라페녹시-1,3-디메틸디실록산, 1,1,3,3-테트라메톡시-1,3-디에틸디실록산, 1,1,3,3-테트라에톡시-1,3-디에틸디실록산, 1,1,3,3-테트라페녹시-1,3-디에틸디실록산, 1,1,3,3-테트라메톡시-1,3-디페닐디실록산, 1,1,3,3-테트라에톡시-1,3-디페닐디실록산, 1,1,3,3-테트라페녹시-1,3-디페닐디실록산, 1,1,3-트리메톡시-1,3,3-트리메틸디실록산, 1,1,3-트리에톡시-1,3,3-트리메틸디실록산, 1,1,3-트리페녹시-1,3,3-트리메틸디실록산, 1,1,3-트리메톡시-1,3,3-트리에틸디실록산, 1,1,3-트리에톡시-1,3,3-트리에틸디실록산, 1,1,3-트리페녹시-1,3,3-트리에틸디실록산, 1,1,3-트리메톡시-1,3,3-트리페닐디실록산, 1,1,3-트리에톡시-1,3,3-트리페닐디실록산, 1,1,3-트리페녹시-1,3,3-트리페닐디실록산, 1,3-디메톡시-1,1,3,3-테트라메틸디실록산, 1,3-디에톡시-1,1,3,3-테트라메틸디실록산, 1,3-디페녹시-1,1,3,3-테트라메틸디실록산, 1,3-디메톡시-1,1,3,3-테트라에틸디실록산, 1,3-디에톡시-1,1,3,3-테 트라에틸디실록산, 1,3-디페녹시-1,1,3,3-테트라에틸디실록산, 1,3-디메톡시-1,1,3,3-테트라페닐디실록산, 1,3-디에톡시-1,1,3,3-테트라페닐디실록산, 1,3-디페녹시-1,1,3,3-테트라페닐디실록산 등을 들 수 있다.
이들 중 헥사메톡시디실록산, 헥사에톡시디실록산, 1,1,3,3-테트라메톡시-1,3-디메틸디실록산, 1,1,3,3-테트라에톡시-1,3-디메틸디실록산, 1,1,3,3-테트라메톡시-1,3-디페닐디실록산, 1,3-디메톡시-1,1,3,3-테트라메틸디실록산, 1,3-디에톡시-1,1,3,3-테트라메틸디실록산, 1,3-디메톡시-1,1,3,3-테트라페닐디실록산, 1,3-디에톡시-1,1,3,3-테트라페닐디실록산 등을 바람직한 예로서 들 수 있다.
또한, 화학식 3에 있어서, d가 0인 화합물로서는 헥사메톡시디실란, 헥사에톡시디실란, 헥사페녹시디실란, 1,1,1,2,2-펜타메톡시-2-메틸디실란, 1,1,1,2,2-펜타에톡시-2-메틸디실란, 1,1,1,2,2-펜타페녹시-2-메틸디실란, 1,1,1,2,2-펜타메톡시-2-에틸디실란, 1,1,1,2,2-펜타에톡시-2-에틸디실란, 1,1,1,2,2-펜타페녹시-2-에틸디실란, 1,1,1,2,2-펜타메톡시-2-페닐디실란, 1,1,1,2,2-펜타에톡시-2-페닐디실란, 1,1,1,2,2-펜타페녹시-2-페닐디실란, 1,1,2,2-테트라메톡시-1,2-디메틸디실란, 1,1,2,2-테트라에톡시-1,2-디메틸디실란, 1,1,2,2-테트라페녹시-1,2-디메틸디실란, 1,1,2,2-테트라메톡시-1,2-디에틸디실란, 1,1,2,2-테트라에톡시-1,2-디에틸디실란, 1,1,2,2-테트라페녹시-1,2-디에틸디실란, 1,1,2,2-테트라메톡시-1,2-디페닐디실란, 1,1,2,2-테트라에톡시-1,2-디페닐디실란, 1,1,2,2-테트라페녹시-1,2-디페닐디실란, 1,1,2-트리메톡시-1,2,2-트리메틸디실란, 1,1,2-트리에톡시-1,2,2-트리메틸디실란, 1,1,2-트리페녹시-1,2,2-트리메틸디실란, 1,1,2-트리메톡시-1,2,2-트리에틸디실란, 1,1,2-트리에톡시-1,2,2-트리에틸디실란, 1,1,2-트리페녹시-1,2,2-트리에틸디실란, 1,1,2-트리메톡시-1,2,2-트리페닐디실란, 1,1,2-트리에톡시-1,2,2-트리페닐디실란, 1,1,2-트리페녹시-1,2,2-트리페닐디실란, 1,2-디메톡시-1,1,2,2-테트라메틸디실란, 1,2-디에톡시-1,1,2,2-테트라메틸디실란, 1,2-디페녹시-1,1,2,2-테트라메틸디실란, 1,2-디메톡시-1,1,2,2-테트라에틸디실란, 1,2-디에톡시-1,1,2,2-테트라에틸디실란, 1,2-디페녹시-1,1,2,2-테트라에틸디실란, 1,2-디메톡시-1,1,2,2-테트라페닐디실란, 1,2-디에톡시-1,1,2,2-테트라페닐디실란, 1,2-디페녹시-1,1,2,2-테트라페닐디실란 등을 들 수 있다.
이들 중, 헥사메톡시디실란, 헥사에톡시디실란, 1,1,2,2-테트라메톡시-1,2-디메틸디실란, 1,1,2,2-테트라에톡시-1,2-디메틸디실란, 1,1,2,2-테트라메톡시-1,2 -디페닐디실란, 1,2-디메톡시-1,1,2,2-테트라메틸디실란, 1,2-디에톡시-1,1,2,2-테트라메틸디실란, 1,2-디메톡시-1,1,2,2-테트라페닐디실란, 1,2-디에톡시-1,1,2,2-테트라페닐디실란 등을 바람직한 예로서 들 수 있다.
또한, 화학식 3에 있어서 R7이 -(CH2)n-으로 표시되는 기의 화합물로서는, 비스(트리메톡시실릴)메탄, 비스(트리에톡시실릴)메탄, 비스(트리-n-프로폭시실릴)메탄, 비스(트리-i-프로폭시실릴)메탄, 비스(트리-n-부톡시실릴)메탄, 비스(트리-sec-부톡시실릴)메탄, 비스(트리-t-부톡시실릴)메탄, 1,2-비스(트리메톡시실릴)에탄, 1,2-비스(트리에톡시실릴)에탄, 1,2-비스(트리-n-프로폭시실릴)에탄, 1,2-비스 (트리-i-프로폭시실릴)에탄, 1,2-비스(트리-n-부톡시실릴)에탄, 1,2-비스(트리- sec-부톡시실릴)에탄, 1,2-비스(트리-t-부톡시실릴)에탄, 1-(디메톡시메틸실릴)-1-(트리메톡시실릴)메탄, 1-(디에톡시메틸실릴)-1-(트리에톡시실릴)메탄, 1-(디-n-프로폭시메틸실릴)-1-(트리-n-프로폭시실릴)메탄, 1-(디-i-프로폭시메틸실릴)-1-(트리-i-프로폭시실릴)메탄, 1-(디-n-부톡시메틸실릴)-1-(트리-n-부톡시실릴)메탄, 1-(디-sec-부톡시메틸실릴)-1-(트리-sec-부톡시실릴)메탄, 1-(디-t-부톡시메틸실릴)-1-(트리-t-부톡시실릴)메탄, 1-(디메톡시메틸실릴)-2-(트리메톡시실릴)에탄, 1-(디에톡시메틸실릴)-2-(트리에톡시실릴)에탄, 1-(디-n-프로폭시메틸실릴)-2-(트리-n-프로폭시실릴)에탄, 1-(디-i-프로폭시메틸실릴)-2-(트리-i-프로폭시실릴)에탄, 1-(디-n-부톡시메틸실릴)-2-(트리-n-부톡시실릴)에탄, 1-(디-sec-부톡시메틸실릴)-2-(트리-sec-부톡시실릴)에탄, 1-(디-t-부톡시메틸실릴)-2-(트리-t-부톡시실릴)에탄, 비스(디메톡시메틸실릴)메탄, 비스(디에톡시메틸실릴)메탄, 비스(디-n-프로폭시메틸실릴)메탄, 비스(디-i-프로폭시메틸실릴)메탄, 비스(디-n-부톡시메틸실릴)메탄, 비스(디-sec-부톡시메틸실릴)메탄, 비스(디-t-부톡시메틸실릴)메탄, 1,2-비스(디메톡시메틸실릴)에탄, 1,2-비스(디에톡시메틸실릴)에탄, 1,2-비스(디-n-프로폭시메틸실릴)에탄, 1,2-비스(디-i-프로폭시메틸실릴)에탄, 1,2-비스(디-n-부톡시메틸실릴)에탄, 1,2-비스(디-sec-부톡시메틸실릴)에탄, 1,2-비스(디-t-부톡시메틸실릴)에탄, 1,2-비스(트리메톡시실릴)벤젠, 1,2-비스(트리에톡시실릴)벤젠, 1,2-비스(트리-n-프로폭시실릴)벤젠, 1,2-비스(트리-i-프로폭시실릴)벤젠, 1,2-비스(트리-n-부톡시실릴)벤젠, 1,2-비스(트리-sec-부톡시실릴)벤젠, 1,2-비스(트리-t-부톡시실릴)벤젠, 1,3-비스(트리메톡시실릴)벤젠, 1,3-비스(트리에톡시실릴)벤젠, 1,3-비스(트리 -n-프로폭시실릴)벤젠, 1,3-비스(트리-i-프로폭시실릴)벤젠, 1,3-비스(트리-n-부톡시실릴)벤젠, 1,3-비스(트리-sec-부톡시실릴)벤젠, 1,3-비스(트리-t-부톡시실릴)벤젠, 1,4-비스(트리메톡시실릴)벤젠, 1,4-비스(트리에톡시실릴)벤젠, 1,4-비스(트리 -n-프로폭시실릴)벤젠, 1,4-비스(트리-i-프로폭시실릴)벤젠, 1,4-비스(트리-n-부톡시실릴)벤젠, 1,4-비스(트리-sec-부톡시실릴)벤젠, 1,4-비스(트리-t-부톡시실릴)벤젠 등을 들 수 있다.
이들 중, 비스(트리메톡시실릴)메탄, 비스(트리에톡시실릴)메탄, 1,2-비스(트리메톡시실릴)에탄, 1,2-비스(트리에톡시실릴)에탄, 1-(디메톡시메틸실릴)-1-(트리메톡시실릴)메탄, 1-(디에톡시메틸실릴)-1-(트리에톡시실릴)메탄, 1-(디메톡시메틸실릴)-2-(트리메톡시실릴)에탄, 1-(디에톡시메틸실릴)-2-(트리에톡시실릴)에탄, 비스(디메톡시메틸실릴)메탄, 비스(디에톡시메틸실릴)메탄, 1,2-비스(디메톡시메틸실릴)에탄, 1,2-비스(디에톡시메틸실릴)에탄, 1,2-비스(트리메톡시실릴)벤젠, 1,2-비스(트리에톡시실릴)벤젠, 1,3-비스(트리메톡시실릴)벤젠, 1,3-비스(트리에톡시실릴)벤젠, 1,4-비스(트리메톡시실릴)벤젠, 1,4-비스(트리에톡시실릴)벤젠 등을 바람직한 예로서 들 수 있다.
본 발명에 있어서, (A) 성분을 구성하는 화합물 (1) 내지 (3)으로서는, 상기 화합물 (1), (2) 및 (3) 중 1종 또는 2종 이상을 사용할 수 있다.
또한, 상기 화합물 (1) 내지 (3)의 군에서 선택된 1종 이상의 실란 화합물을 가수분해, 축합시킬 때, 화합물 (1) 내지 (3)의 군에서 선택된 1종 이상의 실란 화합물 1 몰 당 20 몰 초과 150 몰 이하의 물을 사용하는 것이 바람직하며, 20 몰 초 과 130 몰의 물을 첨가하는 것이 특히 바람직하다. 첨가하는 물의 양이 20 몰 이하이면 도포막의 내균열성이 떨어지는 경우가 있고, 150 몰을 넘으면 가수분해 및 축합 반응 중의 중합체 석출 및 겔화가 발생하는 경우가 있다.
또한, 상기 (A) 성분을 반응액에 첨가할 때에는, 일괄적으로 (A) 성분을 첨가할 수도, (A) 성분을 연속적 또는 단속적으로 첨가할 수도 있다. 연속적 또는 단속적으로 첨가하는 경우, 그 첨가 시간은 5분 내지 12시간이 바람직하다.
본 발명의 (A) 가수분해 축합물을 제조할 때에는, 상기 화합물 (1) 내지 (3)의 군에서 선택된 1종 이상의 실란 화합물을 가수분해, 축합시킬 때, 특정 염기성 화합물을 사용하는 것이 특징이다.
특정 염기성 화합물을 사용함으로써 저비유전율, 고탄성율, 나아가 기판과의 밀착성이 우수한 실리카계 막을 얻을 수 있다.
본 발명에서 사용할 수 있는 특정 염기성 화합물로서는, 예를 들면 수산화테트라메틸암모늄, 수산화테트라에틸암모늄, 수산화테트라프로필암모늄, 수산화테트라부틸암모늄 등의 수산화테트라알킬암모늄, 피페리딘, 1-메틸피페리딘, 2-메틸피페리딘, 3-메틸피페리딘, 4-메틸피페리딘, 피페라진, 1-메틸피페라진, 2-메틸피페라진, 1,4-디메틸피페라진, 피롤리딘, 1-메틸피롤리딘, 디아자비시클로옥탄, 디아자비시클로노난, 디아자비시클로운데센, 2-피라졸린, 3-피롤린, 퀴누클리딘 등의 지방족 환상 유기 아민, 수산화나트륨, 수산화칼륨, 수산화리튬, 수산화세슘 등의 금속 수산화물을 들 수 있고, 수산화테트라메틸암모늄, 수산화테트라에틸암모늄, 수산화테트라프로필암모늄, 수산화테트라부틸암모늄, 피페리딘, 1-메틸피페리딘, 피페라진, 1-메틸피페라진, 1,4-디메틸피페라진, 피롤리딘, 1-메틸피롤리딘, 디아자비시클로옥탄, 디아자비시클로노난, 디아자비시클로운데센, 수산화나트륨, 수산화칼륨, 수산화리튬이 실리카계 막의 기판으로의 밀착성의 관점에서 특히 바람직하다.
이들 특정 염기성 화합물은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
상기 특정 염기성 화합물의 사용량은, 화합물 (1) 내지 (3) 중의 R1O-기, R2O-기, R4O-기 및 R5O-기로 표시되는 기의 총량 1 몰에 대하여, 통상 0.00001 내지 10 몰, 바람직하게는 0.00005 내지 5 몰, 특히 바람직하게는 0.001 내지 1 몰, 더욱 바람직하게는 0.01 내지 0.5 몰이다. 특정 염기성 화합물의 사용량이 상기 범위 내이면, 반응 중의 중합체 석출이나 겔화의 우려가 적다.
이와 같이 하여 얻어지는 (A) 가수분해 축합물의 관성 반경은, GPC (굴절율, 점도, 광산란 측정)법에 의한 관성 반경이며, 바람직하게는 5 내지 50 nm, 더욱 바람직하게는 8 내지 40 nm, 특히 바람직하게는 9 내지 20 nm이다. 가수분해 축합물의 관성 반경이 5 내지 50 nm이면, 얻어지는 실리카계 막의 비유전율, 탄성율 및 막의 균일성이 특히 우수할 수 있다.
또한, 이와 같이 하여 얻어지는 (A) 가수분해 축합물은, 입자 형태를 취하고 있지 않음으로써 기판형으로의 도포성이 우수하다는 특징을 갖고 있다. 입자 형태를 취하고 있지 않은 것은, 예를 들면 투과형 전자 현미경 관찰(TEM)에 의해 확인된다.
또한, (A) 성분 중, 각 성분을 완전 가수분해 축합물로 환산했을 때, 화합물 (2)는 화합물 (1) 내지 (3)의 총량 중, 5 내지 75 중량%, 바람직하게는 10 내지 70 중량%, 더욱 바람직하게는 15 내지 70 중량%이다. 또한, 화합물 (1) 및(또는) (3)은, 화합물 (1) 내지 (3)의 총량 중, 95 내지 25 중량%, 바람직하게는 90 내지 30 중량%, 더욱 바람직하게는 85 내지 30 중량%이다. 화합물 (2)가, 화합물 (1) 내지 (3)의 총량 중, 5 내지 75 중량%인 것이 얻어지는 도포막의 탄성율이 높고, 또한 저유전성이 특히 우수하다.
여기에서, 본 발명에 있어서 완전 가수분해 축합물이란, 화합물 (1) 내지 (3) 중의 R1O-기, R2O-기, R4O-기 및 R5O-기가 1O0 % 가수분해하여 SiOH기가 되고, 더욱 완전히 축합하여 실록산 구조가 된 것을 말한다.
또한, (A) 성분으로서는 얻어지는 조성물의 저장 안정성이 보다 우수하기 때문에, 화합물 (1) 및 화합물 (2)의 가수분해 축합물이 바람직하다.
또한, (A) 가수분해 축합물에서는, 화합물 (1) 내지 (3)의 군에서 선택된 1종 이상의 실란 화합물을 특정 염기성 화합물의 존재하에서 가수분해·축합하여 가수분해 축합물로 하고, 바람직하게는 그 관성 반경을 5 내지 50 nm로 하는데, 그 후 조성물의 pH를 7 이하로 조정하는 것이 바람직하다.
pH를 조정하는 방법으로서는,
① pH 조정제를 첨가하는 방법,
② 상압 또는 감압하에서 조성물로부터 특정 염기성 화합물을 증류 제거하는 방법,
③ 질소, 아르곤 등의 가스를 버블링함으로써, 조성물 중에서 특정 염기성 화합물을 제거하는 방법,
④ 이온 교환 수지에 의해, 조성물 중에서 특정 염기성 화합물을 제거하는 방법,
⑤ 추출이나 세정에 의해 특정 염기성 화합물을 계 밖으로 제거하는 방법 등을 들 수 있다. 이들 방법은 각각, 조합하여 사용할 수 있다.
여기에서, 상기 pH 조정제로서는 무기산 및 유기산을 들 수 있다.
무기산으로서는, 예를 들면 염산, 질산, 황산, 불산, 인산, 붕산, 옥살산 등을 들 수 있다.
또한, 유기산으로서는 예를 들면, 아세트산, 프로피온산, 부탄산, 펜탄산, 헥산산, 헵탄산, 옥탄산, 노난산, 데칸산, 옥살산, 말레산, 메틸말론산, 아디프산, 세박산, 갈산, 부티르산, 멜리트산, 아라키돈산, 시킴산, 2-에틸헥산산, 올레산, 스테아르산, 리놀산, 리놀레산, 살리실산, 벤조산, p-아미노벤조산, p-톨루엔술폰산, 벤젠술폰산, 모노클로로아세트산, 디클로로아세트산, 트리클로로아세트산, 트리플루오로아세트산, 포름산, 말론산, 술폰산, 프탈산, 푸마르산, 시트르산, 타르타르산, 숙신산, 푸마르산, 이타콘산, 메사콘산, 시트라콘산, 말산, 글루타르산의 가수분해물, 무수 말레산의 가수분해물, 무수 프탈산의 가수분해물 등을 들 수 있다.
이들 화합물은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
상기 pH 조정제에 의한 조성물의 pH는 7 이하, 바람직하게는 1 내지 6으로 조정된다. 이와 같이 가수분해 축합물의 관성 반경을 5 내지 50 nm로 한 후, 상기 pH 조정제에 의해 상기 범위 내로 pH를 조정함으로써, 얻어지는 조성물의 저장 안정성이 향상된다는 효과를 얻을 수 있다.
pH 조정제의 사용량은 조성물의 pH가 상기 범위 내가 되는 양이며, 그 사용량은 적절히 선택된다.
(B)유기 용매
본 발명의 막 형성용 조성물은, (A) 성분을 통상 (B)유기 용매에 용해 또는 분산하여 이루어진다.
상기 (B)유기 용매로서는, 알콜계 용매, 케톤계 용매, 아미드계 용매, 에스테르계 용매 및 비프로톤계 용매 군에서 선택된 1종 이상을 들 수 있다.
여기에서, 알콜계 용매로서는 메탄올, 에탄올, n-프로판올, i-프로판올, n-부탄올, i-부탄올, sec-부탄올, t-부탄올, n-펜탄올, i-펜탄올, 2-메틸부탄올, sec-펜탄올, t-펜탄올, 3-메톡시부탄올, n-헥산올, 2-메틸펜탄올, sec-헥산올, 2-에틸부탄올, sec-헵탄올, 헵탄올-3, n-옥탄올, 2-에틸헥산올, sec-옥탄올, n-노닐알콜, 2,6-디메틸헵탄올-4, n-데칸올, sec-운데실알콜, 트리메틸노닐알콜, sec-테트라데실알콜, sec-헵타데실알콜, 페놀, 시클로헥산올, 메틸시클로헥산올, 3,3,5-트리메틸시클로헥산올, 벤질알콜, 디아세톤알콜 등의 모노알콜계 용매;
에틸렌글리콜, 1,2-프로필렌글리콜, 1,3-부틸렌글리콜, 펜탄디올-2,4, 2-메틸펜탄디올-2,4, 헥산디올-2,5, 헵탄디올-2,4, 2-에틸헥산디올-1,3, 디에틸렌글리 콜, 디프로필렌글리콜, 트리에틸렌글리콜, 트리프로필렌글리콜 등의 다가 알콜계 용매;
에틸렌글리콜 모노메틸에테르, 에틸렌글리콜 모노에틸에테르, 에틸렌글리콜 모노프로필에테르, 에틸렌글리콜 모노부틸에테르, 에틸렌글리콜 모노헥실에테르, 에틸렌글리콜 모노페닐에테르, 에틸렌글리콜 모노-2-에틸부틸에테르, 디에틸렌글리콜 모노메틸에테르, 디에틸렌글리콜 모노에틸에테르, 디에틸렌글리콜 모노프로필에테르, 디에틸렌글리콜 모노부틸에테르, 디에틸렌글리콜 모노헥실에테르, 프로필렌글리콜 모노메틸에테르, 프로필렌글리콜 모노에틸에테르, 프로필렌글리콜 모노프로필에테르, 프로필렌글리콜 모노부틸에테르, 디프로필렌글리콜 모노메틸에테르, 디프로필렌글리콜 모노에틸에테르, 디프로필렌글리콜 모노프로필에테르 등의 다가 알콜 부분 에테르계 용매 등을 들 수 있다.
이들 알콜계 용매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
케톤계 용매로서는, 아세톤, 메틸에틸케톤, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 디에틸케톤, 메틸-i-부틸케톤, 메틸-n-펜틸케톤, 에틸-n-부틸케톤, 메틸-n-헥실케톤, 디-i-부틸케톤, 트리메틸노나논, 시클로헥사논, 2-헥사논, 메틸시클로헥사논, 2,4-펜탄디온, 아세토닐아세톤, 아세토페논, 펜촌 등 외에 아세틸아세톤, 2,4-헥산디온, 2,4-헵탄디온, 3,5-헵탄디온, 2,4-옥탄디온, 3,5-옥탄디온, 2,4-노난디온, 3,5-노난디온, 5-메틸-2,4-헥산디온, 2,2,6,6-테트라메틸-3,5-헵탄디온, 1,1,1,5,5,5-헥사플루오로-2,4-헵탄디온 등의 β-디케톤류 등을 들 수 있다.
이들 케톤계 용매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
아미드계 용매로서는 포름아미드, N-메틸포름아미드, N,N-디메틸포름아미드, N-에틸포름아미드, N,N-디에틸포름아미드, 아세트아미드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-에틸아세트아미드, N,N-디에틸아세트아미드, N-메틸프로피온아미드, N-메틸피롤리돈, N-포르밀모르폴린, N-포르밀피페리딘, N-포르밀피롤리딘, N-아세틸모르폴린, N-아세틸피페리딘, N-아세틸피롤리딘 등을 들 수 있다.
이들 아미드계 용매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
에스테르계 용매로서는, 디에틸카르보네이트, 탄산 에틸렌, 탄산 프로필렌, 탄산 디에틸, 아세트산 메틸, 아세트산 에틸, γ-부티로락톤, γ-발레로락톤, 아세트산 n-프로필, 아세트산 i-프로필, 아세트산 n-부틸, 아세트산 i-부틸, 아세트산 sec-부틸, 아세트산 n-펜틸, 아세트산 sec-펜틸, 아세트산 3-메톡시부틸, 아세트산 메틸펜틸, 아세트산 2-에틸부틸, 아세트산 2-에틸헥실, 아세트산 벤질, 아세트산 시클로헥실, 아세트산 메틸시클로헥실, 아세트산 n-노닐, 아세트아세트산메틸, 아세트아세트산에틸, 아세트산에틸렌글리콜 모노메틸에테르, 아세트산에틸렌글리콜 모노에틸에테르, 아세트산디에틸렌글리콜 모노메틸에테르, 아세트산디에틸렌글리콜 모노에틸에테르, 아세트산디에틸렌글리콜 모노-n-부틸에테르, 아세트산프로필렌글리콜 모노메틸에테르, 아세트산프로필렌글리콜 모노에틸에테르, 아세트산프로필렌글리콜 모노프로필에테르, 아세트산프로필렌글리콜 모노부틸에테르, 아세트산디프로필렌글리콜 모노메틸에테르, 아세트산디프로필렌글리콜 모노에틸에테르, 디아세트산글리콜, 아세트산메톡시트리글리콜, 프로피온산 에틸, 프로피온산 n-부틸, 프로피온산 i-아밀, 옥살산 디에틸, 옥살산 디-n-부틸, 젖산 메틸, 젖산 에틸, 젖산 n-부틸, 젖산 n-아밀, 말론산 디에틸, 프탈산 디메틸, 프탈산 디에틸 등을 들 수 있다.
이들 에스테르계 용매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
비프로톤계 용매로서는, 아세토니트릴, 디메틸술폭시드, N,N,N',N'-테트라에틸술파미드, 헥사메틸인산트리아미드, N-메틸모르포론, N-메틸피롤, N-에틸피롤, N-메틸-△3-피롤린, N-메틸피페리딘, N-에틸피페리딘, N,N-디메틸피페라진, N-메틸이미다졸, N-메틸-4-피페리돈, N-메틸-2-피페리돈, N-메틸-2-피롤리돈, 1,3-디메틸-2-이미다졸리디논, 1,3-디메틸테트라히드로-2(1H)-피리미디논 등을 들 수 있다.
이들 유기 용매 중에서 특히 하기 화학식 4로 표시되는 유기 용매가 바람직하다.
식 중, R8 및 R9는 각각 독립적으로 수소 원자, 탄소수 1 내지 4의 알킬기 또는 CH3CO-로부터 선택되는 1가의 유기기를 나타내고, e는 1 내지 2의 정수를 나타낸다.
상기한 유기 용매는 1종 또는 2종 이상을 혼합하여 사용할 수 있다.
본 발명에 있어서는, 화합물 (1) 내지 (3)을 가수분해하여 축합할 때, 상기 와 동일한 용매를 사용할 수 있다.
본 발명 조성물의 구체적인 제조 방법으로서는, 화합물 (1) 내지 (3)을 용해시킨 용매 중에 물 또는 용매로 희석한 물을 단속적 또는 연속적으로 첨가한다. 이 때, 특정 염기성 화합물은 용매 중에 미리 첨가해 둘 수도 있고, 수소 첨가시에 수중에 용해 또는 분산시킬 수도 있다. 이 때의 반응 온도는 통상 0 내지 100 ℃, 바람직하게는 15 내지 90 ℃이다.
그 밖의 첨가제
본 발명에서 얻어지는 막 형성용 조성물에는, 또한 콜로이드형 실리카, 콜로이드형 알루미나, 유기 중합체, 계면활성제, 실란 커플링제, 라디칼 발생제, 트리아젠 화합물 등의 성분을 첨가할 수도 있다.
콜로이드형 실리카란, 예를 들면 고순도의 무수 규산을 상기 친수성 유기 용매에 분산한 분산액이며, 통상 평균 입경이 5 내지 30 nm, 바람직하게는 10 내지 20 nm, 고형분 농도가 10 내지 40 중량% 정도의 것이다. 이러한 콜로이드형 실리카로서는, 예를 들면 닛산 가가꾸 고교(주) 제조의 메탄올 실리카 졸 및 이소프로판올 실리카 졸; 쇼꾸바이 가세이 고교(주) 제조의 오스칼 등을 들 수 있다.
콜로이드형 알루미나로서는, 닛산 가가꾸 고교(주) 제조의 알루미나 졸 520, 100, 200; 가와껭 파인 케미컬(주) 제조의 알루미나 클리어 졸, 알루미나 졸 10, 132 등을 들 수 있다.
유기 중합체로서는 예를 들면, 당쇄 구조를 갖는 화합물, 비닐아미드계 중합체, (메트)아크릴계 중합체, 방향족 비닐 화합물, 덴드리머, 폴리이미드, 폴리아미 드산, 폴리아릴렌, 폴리아미드, 폴리퀴녹살린, 폴리옥사디아졸, 불소계 중합체, 폴리알킬렌옥시드 구조를 갖는 화합물 등을 들 수 있다.
폴리알킬렌옥시드 구조를 갖는 화합물로서는, 폴리메틸렌옥시드 구조, 폴리에틸렌옥시드 구조, 폴리프로필렌옥시드 구조, 폴리테트라메틸렌옥시드 구조, 폴리부틸렌옥시드 구조 등을 들 수 있다.
구체적으로는, 폴리옥시메틸렌 알킬에테르, 폴리옥시에틸렌 알킬에테르, 폴리옥시에틸렌 알킬페닐에테르, 폴리옥시에틸렌 스테롤에테르, 폴리옥시에틸렌 라놀린 유도체, 알킬페놀포르말린 축합물의 산화에틸렌 유도체, 폴리옥시에틸렌 폴리옥시프로필렌 블록 공중합체, 폴리옥시에틸렌 폴리옥시프로필렌알킬에테르 등의 에테르형 화합물, 폴리옥시에틸렌 글리세린 지방산 에스테르, 폴리옥시에틸렌 소르비탄 지방산 에스테르, 폴리옥시에틸렌 소르비톨 지방산 에스테르, 폴리옥시에틸렌 지방산 알칸올아미드 황산염 등의 에테르에스테르형 화합물, 폴리에틸렌글리콜 지방산 에스테르, 에틸렌글리콜 지방산 에스테르, 지방산 모노글리세리드, 폴리글리세린 지방산 에스테르, 소르비탄 지방산 에스테르, 프로필렌글리콜 지방산 에스테르, 자당 지방산 에스테르 등의 에테르에스테르형 화합물 등을 들 수 있다.
폴리옥시에틸렌 폴리옥시프로필렌 블록 공중합체로서는, 하기와 같은 블록 구조를 갖는 화합물을 들 수 있다.
-(X)j-(Y)k-
-(X)j-(Y)k-(X)l-
식 중, X는 -CH2CH2O-로 표시되는 기, Y는 -CH2CH(CH3)O-로 표시되는 기를 나타내고, j는 1 내지 90, k는 10 내지 99, l은 0 내지 90의 수를 나타낸다.
이들 중에서 폴리옥시에틸렌 알킬에테르, 폴리옥시에틸렌 폴리옥시프로필렌 블록 공중합체, 폴리옥시에틸렌 폴리옥시프로필렌알킬에테르, 폴리옥시에틸렌 글리세린 지방산 에스테르, 폴리옥시에틸렌 소르비탄 지방산 에스테르, 폴리옥시에틸렌 소르비톨 지방산 에스테르 등의 에테르형 화합물을 보다 바람직한 예로서 들 수 있다.
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
계면활성제로서는, 예를 들면 비이온계 계면활성제, 음이온계 계면활성제, 양이온계 계면활성제, 양성 계면활성제 등을 들 수 있으며, 또한 불소계 계면활성제, 실리콘계 계면활성제, 폴리알킬렌옥시드계 계면활성제, 폴리(메트)아크릴레이트계 계면활성제 등을 들 수 있고, 바람직하게는 불소계 계면활성제, 실리콘계 계면활성제를 들 수 있다.
불소계 계면활성제로서는, 예를 들면 1,1,2,2-테트라플로로옥틸(1,1,2,2-테트라플로로프로필)에테르, 1,1,2,2-테트라플로로옥틸헥실에테르, 옥타에틸렌글리콜 디(1,1,2,2-테트라플로로부틸)에테르, 헥사에틸렌글리콜(1,1,2,2,3,3-헥사플로로펜틸)에테르, 옥타프로필렌글리콜 디(1,1,2,2-테트라플로로부틸)에테르, 헥사프로필렌글리콜 디(1,1,2,2,3,3-헥사플로로펜틸)에테르, 퍼플로로도데실술폰산나트륨, 1,1,2,2,8,8,9,9,10,10-데카플로로도데칸, 1,1,2,2,3,3-헥사플로로데칸, N-[3-(퍼 플루오로옥탄술폰아미드)프로필]-N,N'-디메틸-N-카르복시메틸렌암모늄베타인, 퍼플루오로알킬술폰아미드프로필 트리메틸암모늄염, 퍼플루오로알킬-N-에틸술포닐글리신염, 인산 비스(N-퍼플루오로옥틸술포닐-N-에틸아미노에틸), 모노퍼플루오로알킬에틸인산 에스테르 등의 말단, 주쇄 및 측쇄 중 한 군데 이상에 플루오로알킬 또는 플루오로알킬렌기를 갖는 화합물로 이루어지는 불소계 계면활성제를 들 수 있다.
또한, 시판품으로서는 메가팩 F142D, F172, F173, F183 (이상, 다이닛본 잉크 가가꾸 고교(주) 제조), 에프 톱 EF301, 303, 352 (신아끼다 가세이(주) 제조), 플루오라이드 FC-430, FC-431 (스미또모 스리엠(주) 제조), 아사히 가드 AG710, 서프론 S-382, SC-101, SC-102, SC-103, SC-104, SC-105, SC-106 (아사히 가라스(주) 제조), BM-1000, BM-1100 (유쇼(주) 제조), NBX-15 ((주)네오스) 등의 명칭으로 시판되고 있는 불소계 계면활성제를 들 수 있다. 이들 중에서도, 상기 메가팩 F172, BM-1000, BM-1100, NBX-15가 특히 바람직하다.
실리콘계 계면활성제로서는, 예를 들면 SH7PA, SH21PA, SH30PA, ST94PA (모두 도레이·다우 코닝·실리콘(주) 제조) 등을 사용할 수 있다. 이들 중에서도 상기 SH28PA, SH30PA가 특히 바람직하다.
계면활성제의 사용량은, (A) 성분 (완전 가수분해 축합물)에 대하여 통상 0.0001 내지 10 중량부이다
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
실란 커플링제로서는, 예를 들면 3-글리시딜옥시프로필 트리메톡시실란, 3-아미노글리시딜옥시프로필 트리에톡시실란, 3-메타크릴옥시프로필 트리메톡시실란, 3-글리시딜옥시프로필메틸 디메톡시실란, 1-메타크릴옥시프로필메틸 디메톡시실란, 3-아미노프로필 트리메톡시실란, 3-아미노프로필 트리에톡시실란, 2-아미노프로필 트리메톡시실란, 2-아미노프로필 트리에톡시실란, N-(2-아미노에틸)-3-아미노프로필 트리메톡시실란, N-(2-아미노에틸)-3-아미노프로필메틸 디메톡시실란, 3-우레이드프로필 트리메톡시실란, 3-우레이드프로필 트리에톡시실란, N-에톡시카르보닐-3-아미노프로필 트리메톡시실란, N-에톡시카르보닐-3-아미노프로필 트리에톡시실란, N-트리에톡시실릴프로필 트리에틸렌트리아민, N-트리에톡시실릴프로필 트리에틸렌트리아민, 10-트리메톡시실릴-1,4,7-트리아자데칸, 10-트리에톡시실릴-1,4,7-트리아자데칸, 9-트리메톡시실릴-3,6-디아자노닐아세테이트, 9-트리에톡시실릴-3,6-디아자노닐아세테이트, N-벤질-3-아미노프로필 트리메톡시실란, N-벤질-3-아미노프로필 트리에톡시실란, N-페닐-3-아미노프로필 트리메톡시실란, N-페닐-3-아미노프로필 트리에톡시실란, N-비스(옥시에틸렌)-3-아미노프로필 트리메톡시실란, N-비스(옥시에틸렌)-3-아미노프로필 트리에톡시실란 등을 들 수 있다.
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
라디칼 발생제로서는, 예를 들면 이소부티릴퍼옥시드, α,α'-비스(네오데카노일퍼옥시)디이소프로필벤젠, 쿠밀퍼옥시네오데카노에이트, 디-n-프로필퍼옥시디카르보네이트, 디이소프로필퍼옥시디카르보네이트, 1,1,3,3-테트라메틸부틸퍼옥시네오데카노에이트, 비스(4-t-부틸시클로헥실)퍼옥시디카르보네이트, 1-시클로헥실-1-메틸에틸퍼옥시네오데카노에이트, 디-2-에톡시에틸퍼옥시디카르보네이트, 디(2-에틸헥실퍼옥시)디카르보네이트, t-헥실퍼옥시네오데카노에이트, 디메톡시부틸퍼옥 시디카르보네이트, 디(3-메틸-3-메톡시부틸퍼옥시)디카르보네이트, t-부틸퍼옥시네오데카노에이트, 2,4-디클로로벤조일퍼옥시드, t-헥실퍼옥시피발레이트, t-부틸퍼옥시피발레이트, 3,5,5-트리메틸헥사노일퍼옥시드, 옥타노일퍼옥시드, 라우로일퍼옥시드, 스테아로일퍼옥시드, 1,1,3,3-테트라메틸부틸퍼옥시-2-에틸헥사노에이트, 숙신퍼옥시드, 2,5-디메틸-2,5-디(2-에틸헥사노일퍼옥시)헥산, 1-시클로헥실-1-메틸에틸퍼옥시-2-에틸헥사노에이트, t-헥실퍼옥시-2-에틸헥사노에이트, t-부틸퍼옥시-2-에틸헥사노에이트, m-톨루오일 앤드 벤조일퍼옥시드, 벤조일퍼옥시드, t-부틸퍼옥시이소부틸레이트, 디-t-부틸퍼옥시-2-메틸시클로헥산, 1,1-비스(t-헥실퍼옥시)-3,3,5-트리메틸시클로헥산, 1,1-비스(t-헥실퍼옥시)시클로헥산, 1,1-비스(t-부틸퍼옥시)-3,3,5-트리메틸시클로헥산, 1,1-비스(t-부틸퍼옥시)시클로헥산, 2,2-비스(4,4-디-t-부틸퍼옥시시클로헥실)프로판, 1,1-비스(t-부틸퍼옥시)시클로데칸, t-헥실퍼옥시이소프로필 모노카르보네이트, t-부틸퍼옥시말레산, t-부틸퍼옥시-3,3,5-트리메틸헥사노에이트, t-부틸퍼옥시라우레이트, 2,5-디메틸-2,5-디(m-톨루오일퍼옥시)헥산, t-부틸퍼옥시이소프로필 모노카르보네이트, t-부틸퍼옥시-2-에틸헥실 모노카르보네이트, t-헥실퍼옥시벤조에이트, 2,5-디메틸-2,5-디(벤조일퍼옥시)헥산, t-부틸퍼옥시아세테이트, 2,2-비스(t-부틸퍼옥시)부탄, t-부틸퍼옥시벤조에이트, n-부틸-4,4-비스(t-부틸퍼옥시)발레에이트, 디-t-부틸퍼옥시이소프탈레이트, α,α'-비스(t-부틸퍼옥시)디이소프로필벤젠, 디쿠밀퍼옥시드, 2,5-디메틸-2,5-디(t-부틸퍼옥시)헥산, t-부틸쿠밀퍼옥시드, 디-t-부틸퍼옥시드, p-멘탄히드로퍼옥시드, 2,5-디메틸-2,5-디(t-부틸퍼옥시)헥신-3, 디이소프로필벤젠히드로퍼옥시 드, t-부틸트리메틸실릴퍼옥시드, 1,1,3,3-테트라메틸부틸히드로퍼옥시드, 쿠멘히드로퍼옥시드, t-헥실히드로퍼옥시드, t-부틸히드로퍼옥시드, 2,3-디메틸-2,3-디페닐부탄 등을 들 수 있다.
라디칼 발생제의 배합량은, 중합체 100 중량부에 대하여 0.1 내지 10 중량부가 바람직하다.
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
트리아젠 화합물로서는, 예를 들면 1,2-비스(3,3-디메틸트리아제닐)벤젠, 1,3-비스(3,3-디메틸트리아제닐)벤젠, 1,4-비스(3,3-디메틸트리아제닐)벤젠, 비스 (3,3-디메틸트리아제닐페닐)에테르, 비스(3,3-디메틸트리아제닐페닐)메탄, 비스 (3,3-디메틸트리아제닐페닐)술폰, 비스(3,3-디메틸트리아제닐페닐)술피드, 2,2-비스[4-(3,3-디메틸트리아제닐페녹시)페닐]-1,1,1,3,3,3-헥사플루오로프로판, 2,2-비스[4-(3,3-디메틸트리아제닐페녹시)페닐]프로판, 1,3,5-트리스(3,3-디메틸트리아제닐)벤젠, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[4-(3,3-디메틸트리아제닐)페닐]플루오렌, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[3-메틸-4-(3,3-디메틸트리아제닐)페닐]플루오렌, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[3-페닐-4-(3,3-디메틸트리아제닐)페닐]플루오렌, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[3-프로페닐-4-(3,3-디메틸트리아제닐)페닐]플루오렌, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[3-플루오로-4-(3,3-디메틸트리아제닐)페닐]플루오렌, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[3,5-디플루오로-4-(3,3-디메틸트리아제닐)페닐]플루오렌, 2,7-비스(3,3-디메틸트리아제닐)-9,9-비스[3-트리플루오로메틸-4-(3,3-디메틸트리 아제닐)페닐]플루오렌 등을 들 수 있다.
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
막 형성용 조성물의 제조 방법
본 발명의 막 형성용 조성물을 제조할 때에는, 예를 들면 용매 중에 화합물 (1) 내지 (3)을 혼합하고 물을 연속적 또는 단속적으로 첨가하여 가수분해하고, 축합하여 (A) 성분을 제조한 후, 여기에 (B)성분을 첨가할 수 있으며, 특히 이것으로 한정되는 것은 아니다.
본 발명 조성물의 제조 방법의 구체적인 예로서는, 하기 1) 내지 11)의 방법 등을 들 수 있다.
1) (A) 성분을 구성하는 화합물 (1) 내지 (3), 특정 염기성 화합물 및 유기 용매로 이루어지는 혼합물에 소정량의 물을 넣고, 가수분해·축합 반응을 행하는 방법.
2) (A) 성분을 구성하는 화합물 (1) 내지 (3), 특정 염기성 화합물 및 유기 용매로 이루어지는 혼합물에 소정량의 물을 연속적 또는 단속적으로 첨가하고, 가수분해, 축합 반응을 행하는 방법.
3) (A) 성분을 구성하는 화합물 (1) 내지 (3) 및 유기 용매로 이루어지는 혼합물에 소정량의 물 및 특정 염기성 화합물을 첨가하고, 가수분해·축합 반응을 행하는 방법.
4) (A) 성분을 구성하는 화합물 (1) 내지 (3) 및 유기 용매로 이루어지는 혼합물에 소정량의 물 및 특정 염기성 화합물을 연속적 또는 단속적으로 첨가하고, 가수분해, 축합 반응을 행하는 방법.
5) 유기 용매, 물 및 특정 염기성 화합물로 이루어지는 혼합물에 소정량의 (A) 성분을 구성하는 화합물 (1) 내지 (3)을 첨가하고, 가수분해·축합 반응을 행하는 방법.
6) 유기 용매, 물 및 특정 염기성 화합물로 이루어지는 혼합물에 소정량의 (A) 성분을 구성하는 화합물 (1) 내지 (3)을 연속적 또는 단속적으로 첨가하고, 가수분해·축합 반응을 행하는 방법.
7) 유기 용매, 물 및 특정 염기성 화합물로 이루어지는 혼합물에 소정량의 (A) 성분을 구성하는 화합물 (1) 내지 (3)을 첨가하고, 가수분해·축합 반응을 행한 후, pH 조정제를 첨가하는 방법.
8) 유기 용매, 물 및 특정 염기성 화합물로 이루어지는 혼합물에 소정량의 (A) 성분을 구성하는 화합물 (1) 내지 (3)을 첨가하고, 가수분해·축합 반응을 행하고, 용액의 일정 농도로 농축한 후 pH 조정제를 첨가하는 방법.
9) 상기 1) 내지 8)의 방법으로 얻어진 용액을 별도의 유기 용매로 추출하는 방법.
10) 상기 1) 내지 8)의 방법으로 얻어진 용액을 별도의 유기 용매로 치환하는 방법.
11) 상기 1) 내지 8)의 방법으로 얻어진 용액을 별도의 유기 용매로 추출한 후, 더욱 별도의 유기 용매로 치환하는 방법.
이와 같이 하여 얻어지는 본 발명 조성물의 전체 고형분 농도는 바람직하게 는 2 내지 30 중량%이고, 사용 목적에 따라 적절히 조정된다. 조성물의 전체 고형분 농도가 2 내지 30 중량%이면, 도포막의 막 두께가 적당한 범위가 되고, 보존 안정성도 보다 우수해진다.
또한, 이 전체 고형분 농도의 조정은, 필요에 따라 농축 및 상기 (D)유기 용매에 의한 희석에 의해 행해진다.
본 발명의 조성물을 실리콘 웨이퍼, SiO2 웨이퍼, SiN 웨이퍼 등의 기재에 도포할 때에는, 스핀 코팅, 침지법, 롤 코팅법, 스프레이법 등의 도장 수단이 사용된다.
이 때의 막 두께는 건조막 두께로서 1회 도포에서 두께 0.05 내지 2.5 ㎛ 정도, 2회 도포에서 두께 0.1 내지 5.0 ㎛ 정도의 도포막을 형성할 수 있다. 그 후, 상온에서 건조하거나, 또는 80 내지 600 ℃ 정도의 온도에서 통상 5 내지 24O분 정도 가열하여 건조함으로써 유리질 또는 거대 고분자의 절연막을 형성할 수 있다.
이 때의 가열 방법으로서는 핫 플레이트, 오븐, 퍼니스 등을 사용할 수 있고, 가열 분위기로서는 대기 상태, 질소 분위기, 아르곤 분위기, 진공 상태, 산소 농도를 조절한 감압 상태 등에서 행할 수 있다.
또한, 전자선이나 자외선을 조사함으로써 도포막을 형성시킬 수도 있다.
또한, 상기 도포막의 경화 속도를 제어하기 위하여, 필요에 따라 단계적으로 가열하거나, 질소, 공기, 산소, 감압 등의 분위기를 선택할 수 있다.
이와 같이 하여 얻어지는 본 발명의 실리카계 막은, 막 밀도가 통상 0.35 내 지 1.2 g/㎤, 바람직하게는 O.4 내지 1.1 g/㎤, 더욱 바람직하게는 O.5 내지 1.O g/㎤이다. 막 밀도가 O.35 g/㎤ 미만에서는 도포막의 기계적 강도가 저하하고, 한편 1.2 g/㎤을 넘으면 저비유전율을 얻을 수 없다.
또한, 본 발명의 실리카계 막은 BJH 법에 의한 세공 분포 측정에 있어서, 10 nm 이상의 빈 구멍이 확인되지 않아 미세 배선간의 층간 절연막 재료로서 바람직하다.
또한, 본 발명의 실리카계 막은 흡수성이 낮은 점에 특징이 있으며, 예를 들어 도포막을 127 ℃, 2.5 atm, 100 %RH의 환경에 1시간 방치했을 경우, 방치 후 도포막의 IR 스펙트럼 관찰로부터는 도포막으로의 물 흡착은 확인되지 않는다.
이 흡수성은, 본 발명에서의 막 형성용 조성물에 사용되는 화합물 (1)의 테트라알콕시실란류의 양에 따라 조정할 수 있다.
또한, 본 발명의 실리카계 막의 비유전율은 통상 2.6 내지 1.2, 바람직하게는 2.5 내지 1.2, 더욱 바람직하게는 2.4 내지 1.2이다.
이렇게 해서 얻어지는 층간 절연막은 PCT 후의 비유전율 특성, PCT 후의 CMP 내성, PCT 후의 기판과의 밀착성을 나타내기 때문에, LSI, 시스템 LSI, DRAM, SDRAM, RDRAM, D-RDRAM 등의 반도체 소자용 층간 절연막이나 에칭 스토퍼막, 반도체 소자의 표면 코팅막 등의 보호막, 다층 레지스트를 이용한 반도체 제조 공정의 중간층, 다층 배선 기판의 층간 절연막, 액정 표시 소자용 보호막 및 절연막 등의 용도로 유용하다.
<실시예>
이하, 본 발명을 실시예를 들어 더욱 구체적으로 설명한다. 단, 이하의 기재는 본 발명의 태양례를 개괄적으로 나타낸 것으로, 특별한 이유가 있는 것은 아니며, 이러한 기재에 의해 본 발명이 한정되는 것은 아니다.
또한, 실시예 및 비교예 중의 "부" 및 "%"는 특별히 언급이 없는 한, 각각 "중량부" 및 "중량%"를 나타낸다.
또한, 각종 평가는, 다음과 같이 하여 행하였다.
관성 반경
하기 조건에 의한 겔 투과 크로마토그래피(GPC) (굴절율, 점도, 광산란 측정)법에 의해 측정하였다.
시료 용액: 실란 화합물의 가수분해 축합물을 고형분 농도가 0.25 %가 되도록 10 mM의 LiBr을 포함하는 메탄올로 희석하고, GPC (굴절율, 점도, 광산란 측정)용 시료 용액으로 사용하였다.
장치: 도소(주) 제조, GPC 시스템 모델 GPC-8020
도소(주) 제조, 칼럼 알파 5000/3000
비스코텍사 제조, 점도 검출기 및 광산란 검출기 모델 T-60 듀얼 미터
캐리어 용액: 10 mM의 LiBr을 포함하는 메탄올
캐리어 송액 속도: 1 ml/min
칼럼 온도: 40 ℃
PCT 후의 비유전율
8 인치 실리콘 웨이퍼 상에 스핀 코팅법을 사용하여 조성물 시료를 도포하 고, 핫 플레이트 상에서 90 ℃로 3분간, 질소 분위기 200 ℃에서 3분간 기판을 건조하고, 다시 450 ℃의 진공(50 mTorr) 핫 플레이트에서 30분간 기판을 소성하였다. 얻어진 막에 대하여 100 ℃, 습도 100 %RH, 2 기압의 조건으로 PCT를 1시간 행하고, 증착법에 의해 알루미늄 전극 패턴을 형성시켜 비유전율 측정용 샘플을 제작하였다. 이 샘플을 주파수 100 kHz의 주파수에서 요꼬가와·휴렛팩커드(주) 제조의 HP16451B 전극 및 HP4284A 프레시젼 LCR 미터를 사용하여 CVD 법에 의해 해당 도포막의 비유전율을 측정하였다.
PCT 후의 CMP 내성
8 인치 실리콘 웨이퍼 상에 스핀 코팅법을 사용하여 조성물 시료를 도포하고, 핫 플레이트 상에서 90 ℃로 3분간, 질소 분위기 200 ℃에서 3분간 기판을 건조하고, 더욱 450 ℃의 진공(50 mTorr) 핫 플레이트에서 30분간 기판을 소성하였다. 얻어진 막에 대하여 100 ℃, 습도 100 %RH, 2 기압의 조건으로 PCT를 1시간 행하였다.
얻어진 도포막을 이하의 조건으로 연마하였다.
슬러리: 실리카 과산화수소계
연마 압력: 160 g/㎠
연마 시간: 180초
CMP 후의 도포막의 외관을 35만 룩스의 표면 관찰용 램프로 관찰하고, 하기 기준으로 평가하였다.
도포막의 밀착성
8 인치 실리콘 웨이퍼 상에 스핀 코팅법을 사용하여 조성물 시료를 도포하고, 핫 플레이트 상에서 90 ℃로 3분간, 질소 분위기 200 ℃에서 3분간 기판을 건조하고, 더욱 450 ℃의 진공(50 mTorr) 핫 플레이트에서 30분간 기판을 소성하였다. 얻어진 막에 대하여 100 ℃, 습도 100 %RH, 2 기압의 조건으로 PCT를 1시간 행하였다. 얻어진 기판 상에 에폭시 수지를 사용하여 스터드 핀(stud pin) 10개를 고정하고, 150 ℃에서 1시간 건조시켰다. 이 스터드 핀에 대하여 세바스찬법을 사용하여 인발 시험을 행하고, 이하의 기준으로 밀착성을 평가하였다.
○: 스터드 핀 10개 모두 실리콘 웨이퍼와 도포막 계면에서의 박리 없음
×: 실리콘 웨이퍼와 도포막 계면에서의 박리 발생
<합성예 1>
석영제 세퍼러블 플라스크에 증류 에탄올 570 g, 이온 교환수 160 g, 10 % 수산화테트라메틸암모늄 수용액 30 g을 넣고, 균일하게 교반하였다. 이 용액에 메틸트리메톡시실란 136 g과 테트라에톡시실란 209 g의 혼합물을 첨가하였다. 용액을 55 ℃로 유지한 채, 2시간 반응을 행하였다. 이 용액에 프로필렌글리콜 모노프로필에테르 300 g을 첨가하고, 그 후 50 ℃의 증발기를 사용하여 용액을 10 % (완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후 아세트산의 10 % 프로필렌글리콜 모노프로필에테르 용액 1O g을 첨가하여 반응액 ①을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 13.4 nm였다.
<합성예 2>
합성예 1에 있어서, 10 % 수산화테트라메틸암모늄 수용액 대신에 10 % 피페 라진 수용액을 사용한 것 이외는, 합성예 1과 동일하게 하여 반응액 ②를 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 13.0 nm였다.
<합성예 3>
합성예 1에 있어서, 10 % 수산화테트라메틸암모늄 수용액 대신에 10 % 디아자비시클로운데센 수용액을 사용한 것 이외는, 합성예 1과 동일하게 하여 반응액 ③을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 15.0 nm였다.
<합성예 4>
합성예 1에 있어서, 10 % 수산화테트라메틸암모늄 수용액 대신에 10 % 수산화나트륨 수용액을 사용한 것 이외는, 합성예 1과 동일하게 하여 반응액 ④를 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 14.8 nm였다.
<합성예 5>
석영제 세퍼러블 플라스크에 증류 에탄올 470.9 g, 이온 교환수 226.5 g, 25 % 수산화테트라메틸암모늄 수용액 17.2 g을 넣고, 균일하게 교반하였다. 이 용액에 메틸트리메톡시실란 44.9 g과 테트라에톡시실란 68.6 g의 혼합물을 첨가하였다. 용액을 55 ℃로 유지한 채, 2시간 반응을 행하였다. 이 용액에 20 % 질산 수용액 50 g을 첨가하고, 충분히 교반한 후 실온까지 냉각하였다. 이 용액에 프로필렌글리콜 모노프로필에테르 4O g을 첨가하고, 그 후 50 ℃의 증발기를 사용하여 용액을 10 % (완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후, 말레산의 10 % 프로필렌글리콜 모노프로필에테르 용액 1O g을 첨가하여 반응액 ⑤를 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 20.9 nm였다.
<합성예 6>
합성예 5에 있어서, 25 % 수산화테트라메틸암모늄 수용액 대신에 25 % 수산화테트라부틸암모늄 수용액을 사용한 것 이외는, 합성예 5와 동일하게 하여 반응액 ⑥을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 22.8 nm였다.
<합성예 7>
합성예 5에 있어서, 프로필렌글리콜 모노프로필에테르 대신에 프로필렌글리콜 모노에틸에테르를 사용한 것 이외는, 합성예 5와 동일하게 하여 반응액 ⑦을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 20.8 nm였다.
<합성예 8>
석영제 세퍼러블 플라스크에 증류 에탄올 470.9 g, 이온 교환수 226.5 g, 25 % 수산화테트라메틸암모늄 수용액 17.2 g을 넣고, 균일하게 교반하였다. 이 용액에 메틸트리메톡시실란 44.9 g과 테트라에톡시실란 68.6 g의 혼합물을 2시간에 걸쳐 첨가하였다. 용액을 59 ℃로 유지한 채, 5시간 반응을 행하였다. 이 용액에 20 % 질산 수용액 50 g을 첨가하고, 충분히 교반한 후 실온까지 냉각하였다. 이 용액에 프로필렌글리콜 모노프로필에테르 4O0 g을 첨가하고, 그 후 50 ℃의 증발기를 사용하여 용액을 10 % (완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후, 말레산의 10 % 프로필렌글리콜 모노프로필에테르 용액 1O g을 첨가하여 반응액 ⑧을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 17.9 nm였다.
<합성예 9>
석영제 세퍼러블 플라스크에 증류 에탄올 470.9 g, 이온 교환수 233.3 g, 25 % 수산화칼륨 수용액 10.4 g을 넣고, 균일하게 교반하였다. 이 용액에 메틸트리메톡시실란 44.9 g과 테트라에톡시실란 68.6 g의 혼합물을 첨가하였다. 용액을 52 ℃로 유지한 채, 2시간 반응을 행하였다. 이 용액에 20 % 질산 수용액 50 g을 첨가하고, 충분히 교반한 후 실온까지 냉각하였다. 이 용액에 프로필렌글리콜 모노프로필에테르 4O0 g을 첨가하고, 그 후 50 ℃의 증발기를 사용하여 용액을 10 % (완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후, 말레산의 10 % 프로필렌글리콜 모노프로필에테르 용액 1O g을 첨가하여 반응액 ⑨를 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 24.6 nm였다.
<합성예 10>
석영제 세퍼러블 플라스크에 증류 에탄올 470.9 g, 이온 교환수 233.3 g, 25 % 수산화칼륨 수용액 10.4 g을 넣고, 균일하게 교반하였다. 이 용액에 메틸트리메톡시실란 44.9 g과 테트라에톡시실란 68.6 g의 혼합물을 30분에 걸쳐 첨가하였다. 용액을 52 ℃로 유지한 채, 1시간 반응을 행하였다. 이 용액에 20 % 질산 수용액 50 g을 첨가하고, 충분히 교반한 후 실온까지 냉각하였다. 이 용액에 프로필렌글리콜 모노프로필에테르 4O0 g을 첨가하고, 그 후 50 ℃의 증발기를 사용하여 용액 을 10 % (완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후, 말레산의 10 % 프로필렌글리콜 모노프로필에테르 용액 1O g을 첨가하여 반응액 ⑩을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 21.6 nm였다.
<비교 합성예 1>
합성예 1에 있어서, 10 % 수산화테트라메틸암모늄 수용액 대신에 10 % 피리딘 수용액을 사용한 것 이외는, 합성예 1과 동일하게 하여 반응액 ⑪을 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 3.8 nm였다.
<비교 합성예 2>
석영제 세퍼러블 플라스크에 메틸트리메톡시실란 154.24 g, 테트라메톡시실란 288.83 g, 증류 프로필렌글리콜 모노에틸에테르 250 g을 용해하고, 말레산 10 g을 용해한 이온 교환수 297 g을 1시간에 걸쳐 용액에 적하하였다. 이 용액을 50 ℃에서 3시간 반응시킴으로써 반응액 ⑫를 얻었다.
이와 같이 하여 얻어진 축합물 등의 관성 반경은 0.2 nm였다.
<실시예 1>
합성예 1에서 얻어진 반응액 ①을 0.2 ㎛ 공경의 테플론제 필터로 여과하여 본 발명의 막 형성용 조성물을 얻었다.
얻어진 조성물을 스핀 코팅법으로 실리콘 웨이퍼 상에 도포하였다.
도포막의 PCT 후의 비유전율은 2.27로 매우 낮은 값이었고, PCT 후의 도포막을 CMP해도 도포막에 손상은 확인되지 않았다. 또한, PCT 후의 도포막의 밀착성도 양호하였다.
<실시예 2 내지 10>
표 1에 나타낸 조성으로 막 형성용 조성물을 제조하고, 실시예 1과 동일하게 평가하였다. 평가 결과를 표 1에 함께 나타낸다.
실시예 | 반응액 | PCT 후의 비유전율 | PCT 후의 CMP 내성 | PCT 후의 밀착성 |
1 | 반응액 ① | 2.27 | O | O |
2 | 반응액 ② | 2.29 | O | O |
3 | 반응액 ③ | 2.14 | O | O |
4 | 반응액 ④ | 2.16 | O | O |
5 | 반응액 ⑤ | 2.15 | O | O |
6 | 반응액 ⑥ | 2.14 | O | O |
7 | 반응액 ⑦ | 2.16 | O | O |
8 | 반응액 ⑧ | 2.10 | O | O |
9 | 반응액 ⑨ | 2.06 | O | O |
10 | 반응액 ⑩ | 1.99 | O | O |
<비교예 1>
비교 합성예 1에서 얻어진 반응액 ⑪을 사용한 것 이외는, 실시예 1과 동일하게 하여 도포막을 평가하였다.
도포막의 PCT 후의 비유전율은 2.67로 비교적 낮은 값이었지만, PCT 후의 도포막을 CMP 처리했을 때 표면에 손상이 확인되었다. 또한, PCT 후의 도포막의 밀착성 평가를 행한 결과, 스터드 풀 핀의 5개에서 실리콘 웨이퍼와 도포막 계면에서의 박리가 발생하였다.
<비교예 2>
비교 합성예 2에서 얻어진 반응액 ⑫를 사용한 것 이외는, 실시예 1과 동일하게 하여 도포막을 평가하였다.
PCT 후의 도포막의 비유전율은 3.88로 높은 값이었다. 또한, PCT 후의 도포막의 밀착성 평가를 행한 결과, 스터드 풀 핀의 3개에서 실리콘 웨이퍼와 도포막 계면에서의 박리가 발생하였다.
본 발명에 따르면, 특정한 염기성 화합물과 물의 존재하에서 알콕시실란 가수분해 및(또는) 축합을 행함으로써, PCT 후의 비유전율 특성, PCT 후의 CMP 내성, PCT 후의 기판과의 밀착성이 우수한 막 형성용 조성물 (층간 절연막용 재료)을 제공할 수 있다.
Claims (9)
- (A) 하기 화학식 1로 표시되는 화합물, 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물 군에서 선택되는 1종 이상의 실란 화합물을 화합물 (1) 내지 (3) 중의 R1O-기, R2O-기, R4O-기 및 R5O-기로 표시되는 기의 총량 1 몰에 대하여 0.01 내지 0.5 몰인 수산화테트라알킬암모늄과 물의 존재하에서 가수분해하고, 축합한 가수분해 축합물 및(B) 유기 용매를 함유하는 것을 특징으로 하는 층간 절연막 형성용 조성물.<화학식 1>RaSi(OR1)4-a식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기, R1은 1가의 유기기, a는 1 내지 2의 정수를 나타낸다.<화학식 2>Si(OR2)4식 중, R2는 1가의 유기기를 나타낸다.<화학식 3>R3 b(R4O)3-bSi-(R7)d-Si(OR5)3-cR6 c식 중, R3 내지 R6은 동일하거나 또는 상이하며 각각 1가의 유기기를 나타내고, b 및 c는 동일하거나 또는 상이하며 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)n-으로 표시되는 기 (여기에서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
- 제1항에 있어서, 물이 상기 실란 화합물 1 몰 당 20 몰 초과 150 몰 이하인 것을 특징으로 하는 층간 절연막 형성용 조성물.
- 제1항에 있어서, 가수분해 축합물이 관성 반경 5 내지 50 nm인 것을 특징으로 하는 층간 절연막 형성용 조성물.
- 제2항에 있어서, 가수분해 축합물이 관성 반경 5 내지 50 nm인 것을 특징으로 하는 층간 절연막 형성용 조성물.
- 제1항에 있어서, 수산화테트라알킬암모늄이 수산화테트라메틸암모늄인 것을 특징으로 하는 층간 절연막 형성용 조성물.
- 제1항에 있어서, pH가 7 이하인 것을 특징으로 하는 층간 절연막 형성용 조성물.
- 제1항에 있어서, (B)유기 용매가 하기 화학식 4로 표시되는 용매인 것을 특징으로 하는 층간 절연막 형성용 조성물.<화학식 4>R8O(CHCH3CH2O)eR9식 중, R8 및 R9는 각각 독립적으로 수소 원자, 탄소수 1 내지 4의 알킬기 또는 CH3CO-로부터 선택되는 1가의 유기기를 나타내고, e는 1 내지 2의 정수를 나타낸다.
- 제1항 내지 제7항 중 어느 한 항에 기재된 층간 절연막 형성용 조성물을 기판에 도포하고, 가열하는 것을 특징으로 하는 막 형성 방법.
- 제8항에 기재된 막 형성 방법에 의해 얻어지는 실리카계 막.
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WO2016167892A1 (en) | 2015-04-13 | 2016-10-20 | Honeywell International Inc. | Polysiloxane formulations and coatings for optoelectronic applications |
US10947412B2 (en) * | 2017-12-19 | 2021-03-16 | Honeywell International Inc. | Crack-resistant silicon-based planarizing compositions, methods and films |
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Publication number | Priority date | Publication date | Assignee | Title |
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US4214057A (en) * | 1978-02-15 | 1980-07-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Coating composition for plastic substrates |
EP0226208A2 (en) * | 1985-12-17 | 1987-06-24 | Sumitomo Chemical Company, Limited | Insulating film for semiconductor, production of the same and liquid composition for producing the same |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US5733644A (en) * | 1994-04-15 | 1998-03-31 | Mitsubishi Chemical Corporation | Curable composition and method for preparing the same |
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2000
- 2000-11-29 JP JP2000363513A patent/JP4195773B2/ja not_active Expired - Fee Related
-
2001
- 2001-04-09 DE DE2001617631 patent/DE60117631T2/de not_active Expired - Lifetime
- 2001-04-09 KR KR1020010018551A patent/KR100739952B1/ko not_active IP Right Cessation
- 2001-04-09 US US09/827,902 patent/US6495264B2/en not_active Expired - Lifetime
- 2001-04-09 EP EP20010108846 patent/EP1146092B1/en not_active Expired - Lifetime
- 2001-04-10 TW TW90108711A patent/TWI286155B/zh not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4214057A (en) * | 1978-02-15 | 1980-07-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Coating composition for plastic substrates |
EP0226208A2 (en) * | 1985-12-17 | 1987-06-24 | Sumitomo Chemical Company, Limited | Insulating film for semiconductor, production of the same and liquid composition for producing the same |
Also Published As
Publication number | Publication date |
---|---|
US20020020327A1 (en) | 2002-02-21 |
DE60117631D1 (de) | 2006-05-04 |
EP1146092A2 (en) | 2001-10-17 |
KR20010100880A (ko) | 2001-11-14 |
JP4195773B2 (ja) | 2008-12-10 |
JP2001354904A (ja) | 2001-12-25 |
EP1146092B1 (en) | 2006-03-08 |
EP1146092A3 (en) | 2002-12-18 |
DE60117631T2 (de) | 2006-10-05 |
US6495264B2 (en) | 2002-12-17 |
TWI286155B (en) | 2007-09-01 |
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