KR20110063351A - Radiation-sensitive resin composition, and interlayer insulating film and method for forming the same - Google Patents
Radiation-sensitive resin composition, and interlayer insulating film and method for forming the same Download PDFInfo
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- KR20110063351A KR20110063351A KR1020100121891A KR20100121891A KR20110063351A KR 20110063351 A KR20110063351 A KR 20110063351A KR 1020100121891 A KR1020100121891 A KR 1020100121891A KR 20100121891 A KR20100121891 A KR 20100121891A KR 20110063351 A KR20110063351 A KR 20110063351A
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- South Korea
- Prior art keywords
- compound
- acid
- resin composition
- sensitive resin
- mass
- Prior art date
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- 230000005855 radiation Effects 0.000 title claims abstract description 89
- 239000011342 resin composition Substances 0.000 title claims abstract description 61
- 239000011229 interlayer Substances 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 229920001577 copolymer Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 8
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 5
- -1 sulfophenyl group Chemical group 0.000 claims description 120
- 238000000576 coating method Methods 0.000 claims description 40
- 239000011248 coating agent Substances 0.000 claims description 37
- 239000000758 substrate Substances 0.000 claims description 29
- 230000008569 process Effects 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 36
- 238000001312 dry etching Methods 0.000 abstract description 20
- 230000035945 sensitivity Effects 0.000 abstract description 19
- 238000002834 transmittance Methods 0.000 abstract description 13
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- 239000010408 film Substances 0.000 description 108
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 36
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- 238000011161 development Methods 0.000 description 21
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- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 7
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- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 6
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
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- 239000007864 aqueous solution Substances 0.000 description 5
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 4
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- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 4
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 4
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical class SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- 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
- G03F7/022—Quinonediazides
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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Abstract
Description
본 발명은, 액정 표시 소자(LCD) 등의 층간 절연막을 형성하기 위한 재료로서 매우 적합한 포지티브형 감방사선성 수지 조성물, 그 조성물로 형성된 층간 절연막 및, 그 층간 절연막의 형성 방법에 관한 것이다. The present invention relates to a positive radiation-sensitive resin composition which is very suitable as a material for forming an interlayer insulating film such as a liquid crystal display device (LCD), an interlayer insulating film formed from the composition, and a method of forming the interlayer insulating film.
박막 트랜지스터(이하, 「TFT」라고 기재함)형 액정 표시 소자, 자기(磁氣) 헤드 소자, 집적 회로 소자, 고체 촬상 소자 등의 전자 부품에는, 일반적으로 층 형상으로 배치되는 배선의 사이를 절연하기 위해 층간 절연막이 형성되어 있다. 층간 절연막을 형성하는 재료로서는, 필요로 하는 패턴 형상을 얻기 위한 공정수가 적고, 게다가 충분한 평탄성을 갖는 것이 바람직한 점에서, 포지티브형 감방사선성 수지 조성물이 폭넓게 사용되고 있다(특허문헌 1 참조). Thin film transistors (hereinafter referred to as "TFT") type liquid crystal display elements, magnetic head elements, integrated circuit elements, and solid state imaging elements are generally insulated between wirings arranged in a layer shape. In order to do this, an interlayer insulating film is formed. As a material which forms an interlayer insulation film, the positive radiation sensitive resin composition is widely used by the point that there are few processes for obtaining the required pattern shape, and it is preferable to have sufficient flatness further (refer patent document 1).
상기 전자 부품 중, 예를 들면, TFT형 액정 표시 소자는, 층간 절연막의 위에 투명 전극막을 형성하고, 그 위에 액정 배향막을 형성하는 공정을 거쳐 제조된다. 이러한 TFT형 액정 표시 소자의 제조에서는, 층간 절연막은, 투명 전극막의 형성 공정에 있어서 고온 조건에 노출되거나, 전극의 패턴 형성에 사용되는 레지스트의 박리액에 노출되거나, 여러 가지 파장의 빛에 노출되게 되기 때문에, 충분한 내(耐)열성, 내용제성 및 내광성이 필요해진다. 또한, 층간 절연막은, 드라이 에칭 공정에 가해지는 경우도 있기 때문에, 드라이 에칭에 대한 충분한 내성이 필요해진다(특허문헌 2 및 특허문헌 3 참조). Among the electronic components, for example, a TFT type liquid crystal display element is manufactured through a process of forming a transparent electrode film on an interlayer insulating film and forming a liquid crystal alignment film thereon. In the manufacture of such a TFT type liquid crystal display element, the interlayer insulating film is exposed to high temperature conditions in the step of forming a transparent electrode film, exposed to a stripping solution of a resist used for pattern formation of the electrode, or exposed to light of various wavelengths. Therefore, sufficient heat resistance, solvent resistance and light resistance are required. Moreover, since an interlayer insulation film may be added to a dry etching process, sufficient tolerance to dry etching is needed (refer patent document 2 and patent document 3).
또한 최근, TFT형 액정 표시 소자는, 대화면화, 고(高)휘도화, 고정세화, 고속 응답화, 박형화 등의 동향에 있다. 그 때문에, TFT형 액정 표시 소자에 이용되는 층간 절연막 형성용의 감방사선성 수지 조성물로서는 방사선에 대하여 고감도임과 함께, 형성되는 층간 절연막으로서는 저(低)유전율, 고광선 투과율 등에 있어서, 종래보다 한층 더 우수한 성능이 요구되고 있다. 또한, 층간 절연막을 형성할 때의 현상 공정에 있어서는, 현상 시간이 최적 시간보다 근소하게라도 과잉이 되면, 패턴과 기판과의 사이에 현상액이 침투하여, 기판으로부터의 패턴의 벗겨짐이 발생하기 쉬워진다. 따라서, 층간 절연막 형성시의 현상 공정에 있어서는, 현상 시간을 엄밀하게 제어할 필요가 있어, 제품의 수율의 점에서 문제가 있었다. In recent years, TFT type liquid crystal display devices are in the trend of large screen, high luminance, high definition, high-speed response, and thinning. Therefore, the radiation sensitive resin composition for forming the interlayer insulation film used for the TFT type liquid crystal display element is highly sensitive to radiation, and as the interlayer insulation film formed, the dielectric constant, high light transmittance, and the like are much higher than before. Excellent performance is required. In the development step when forming the interlayer insulating film, if the developing time is excessively slightly smaller than the optimum time, the developer penetrates between the pattern and the substrate, and the peeling of the pattern from the substrate is likely to occur. . Therefore, in the development process at the time of forming an interlayer insulation film, it is necessary to strictly control development time, and there existed a problem in the point of product yield.
이와 같이, 감방사선성 수지 조성물로부터 층간 절연막을 형성함에 있어서, 조성물로서는, 도포성이 우수하고, 방사선에 대하여 고감도인 것이 요구되고, 또한, 층간 절연막의 형성시의 현상 공정에 있어서는, 현상 시간이 소정 시간보다 과잉이 된 경우라도, 양호한 패턴 형상을 나타내고, 그리고 형성되는 층간 절연막으로서는, 내열성, 내용제성, 광선 투과율, 내드라이 에칭성 등에 있어서 우수한 것이 요구된다. 그러나, 그러한 요구를 모두 만족하는 감방사선성 수지 조성물은, 종래 알려져 있지 않다. Thus, in forming an interlayer insulation film from a radiation sensitive resin composition, as a composition, it is required to be excellent in applicability | paintability and to be highly sensitive to radiation, and, in the developing process at the time of formation of an interlayer insulation film, developing time is Even if it exceeds the predetermined time, it is desired to exhibit a good pattern shape and to be excellent in heat resistance, solvent resistance, light transmittance, dry etching resistance, and the like. However, the radiation sensitive resin composition which satisfy | fills all those requirements is not known conventionally.
본 발명은 이상과 같은 사정에 기초하여 이루어진 것으로, 그 목적은, 도포성이 우수하고, 방사선 감도 및, 양호한 패턴 형상이 얻어짐과 함께, 내열성, 내용제성, 광선 투과율, 내드라이 에칭성이 우수한 층간 절연막을 형성하는 것이 가능한 포지티브형 감방사선성 수지 조성물, 그 조성물로부터 얻어진 층간 절연막, 및 그 층간 절연막의 형성 방법을 제공하는 것이다. This invention is made | formed based on the above circumstances, The objective is excellent in applicability | paintability, the radiation sensitivity and a favorable pattern shape are obtained, and it is excellent in heat resistance, solvent resistance, light transmittance, and dry etching resistance. The positive radiation sensitive resin composition which can form an interlayer insulation film, the interlayer insulation film obtained from this composition, and the formation method of this interlayer insulation film are provided.
상기 과제를 해결하기 위해 이루어진 발명은,The invention made to solve the above problems,
[A] 알칼리 가용성 수지,[A] alkali-soluble resin,
[B] 1,2-퀴논디아자이드 화합물 및,[B] 1,2-quinonediazide compound, and
[C] 하기 일반식 (1)로 나타나는 화합물을 포함하는 감방사선성 수지 조성물이다. (C) It is a radiation sensitive resin composition containing the compound represented by following General formula (1).
(식 (1) 중, X는, 탄소수 6∼20의 2가의 직쇄상 지방족 탄화 수소기이고, Y1 및 Y2는, 각각 독립적으로, 단결합, 에스테르 결합, 아미드 결합 또는 우레탄 결합이고, R1 및 R2는, 각각 독립적으로, 수소 원자, 탄소수 1∼6의 알킬기, 술포기, 술포페닐기, 또는 하기식 (2)의 (i)∼(vi)의 어느 것으로 나타나는 기이고; 단, Y1 및 Y2가 동시에 단결합일 때, R1 및 R2가 수소원자 또는 탄소수 1∼6의 알킬기인 경우는 없음)(Wherein (1), X is a divalent straight-chain aliphatic hydrocarbon group having a carbon number of 6~20, Y 1 and Y 2 are, each independently, a single bond, an ester bond, an amide bond or a urethane bond, R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a sulfo group, a sulfophenyl group, or a group represented by any of (i) to (vi) of the following formula (2); When 1 and Y 2 are a single bond at the same time, R 1 and R 2 are not a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)
(2) (2)
(식 (i)∼(vi) 중, R3은, 수소 원자 또는 탄소수 1∼6의 알킬기이고, R4는, 수소 원자 또는 메틸기이고, m은, 0∼6의 정수이고, 단, 상기식 (1)의 Y1 또는 Y2가 단결합일 때, 이 Y1 또는 Y2와 연결하는 R3 또는 R4에 있어서의 m은 0임).(In formula (i)-(vi), R <3> is a hydrogen atom or a C1-C6 alkyl group, R <4> is a hydrogen atom or a methyl group, m is an integer of 0-6, and is a said formula When Y 1 or Y 2 in (1) is a single bond, m in R 3 or R 4 connecting with Y 1 or Y 2 is 0).
당해 포지티브형 감방사선성 수지 조성물은, [A] 알칼리 가용성 수지, [B] 1,2-퀴논디아자이드 화합물과 [C] 하기 일반식 (1)로 나타나는 화합물을 함유하기 때문에, 도포성이 우수하고, 방사선 감도 및, 패턴 형상이 우수하고, 또한, 내열성, 내용제성, 광선 투과율, 내드라이 에칭성이 우수한 층간 절연막을 형성하는 것이 가능하다. Since the said positive radiation sensitive resin composition contains [A] alkali-soluble resin, [B] 1,2-quinonediazide compound, and the compound represented by [C] following General formula (1), it is excellent in applicability | paintability. In addition, it is possible to form an interlayer insulating film excellent in radiation sensitivity and pattern shape and excellent in heat resistance, solvent resistance, light transmittance, and dry etching resistance.
또한, 본 발명의 층간 절연막의 형성 방법은,In addition, the method of forming the interlayer insulating film of the present invention,
(1) 본 발명의 포지티브형 감방사선성 수지 조성물의 도막을 기판 상에 형성하는 공정, (1) Process of forming the coating film of positive type radiation sensitive resin composition of this invention on board | substrate,
(2) 공정 (1)에서 형성한 도막의 적어도 일부에 방사선을 조사하는 공정, (2) irradiating at least a part of the coating film formed in step (1) with radiation;
(3) 공정 (2)에서 방사선이 조사된 도막을 현상하는 공정 및, (3) developing the coating film irradiated with radiation in step (2), and
(4) 공정 (3)에서 현상된 도막을 가열하는 공정(4) Step of heating the coating film developed in Step (3)
을 포함하고 있다. It includes.
당해 방법에 있어서는, 우수한 도포성과 높은 방사선 감도를 갖는 상기 감방사선성 수지 조성물을 이용하여, 감방사선성을 이용한 노광·현상·가열에 의해 패턴을 형성함으로써, 미세하고 그리고 정교한 패턴을 갖는 층간 절연막을 용이하게 형성할 수 있다. 이렇게 하여 형성된 층간 절연막은, 내열성, 내용제성, 광선 투과율, 내드라이 에칭성에 있어서 우수하다. 또한, 이러한 층간 절연막은, TFT형 액정 표시 소자를 비롯하여, 자기 헤드 소자, 집적 회로 소자, 고체 촬상 소자 등의 전자 부품에 폭넓게 이용할 수 있다. In this method, by using the radiation-sensitive resin composition having excellent coating properties and high radiation sensitivity, a pattern is formed by exposure, development, and heating using radiation sensitivity, thereby forming an interlayer insulating film having a fine and sophisticated pattern. It can be formed easily. The interlayer insulating film thus formed is excellent in heat resistance, solvent resistance, light transmittance, and dry etching resistance. Moreover, such an interlayer insulation film can be widely used for electronic components, such as a magnetic head element, an integrated circuit element, and a solid-state image sensor, as well as a TFT type liquid crystal display element.
본 발명의 포지티브형 감방사선성 수지 조성물은, 우수한 도포성, 높은 감방사선 감도를 가져, 양호한 패턴 형상을 형성할 수 있다. 또한, 당해 포지티브형 감방사선성 수지 조성물로부터는, 내열성, 내용제성, 광선 투과율, 내드라이 에칭성에 있어서 우수한 전자 부품의 층간 절연막을 형성하는 것이 가능하다.The positive radiation sensitive resin composition of this invention has the outstanding applicability | paintability and high radiation sensitivity, and can form a favorable pattern shape. Moreover, it is possible to form the interlayer insulation film of the electronic component excellent in heat resistance, solvent resistance, light transmittance, and dry etching resistance from the said positive radiation sensitive resin composition.
(발명을 실시하기 위한 형태)(Form to carry out invention)
이하, 본 발명의 감방사선성 수지 조성물에 포함되는 각 성분 및 그 외의 임의 성분에 대해서 상세하게 설명한다. Hereinafter, each component and other arbitrary components contained in the radiation sensitive resin composition of this invention are demonstrated in detail.
[A] 알칼리 가용성 수지에 대해서, 이하에 설명한다. [A] Alkali-soluble resin is demonstrated below.
본 발명에 있어서의 [A] 알칼리 가용성 수지(이하, [A] 성분이라고 말하는 경우도 있음)로서는, 당해 성분을 포함하는 감방사선성 수지 조성물의 현상 처리 공정에 있어서 이용되는 알칼리 현상액에 대하여 용해성을 갖는 것이 필요하다. As [A] alkali-soluble resin (Hereinafter, it may be said to [A] component) in this invention, it has solubility with respect to the alkaline developing solution used in the image development process of the radiation sensitive resin composition containing the said component. It is necessary to have.
이러한 알칼리 가용성 수지로서는, (a1) 불포화 카본산 및/또는 불포화 카본산 무수물(이하, 화합물(a1)이라고도 함) 및, 이것과 공중합 가능한 다른 불포화 화합물의 공중합체가 바람직하고, (a1) 불포화 카본산 및/또는 불포화 카본산 무수물, 및 (a2) 에폭시기 함유 불포화 화합물을 포함하는 불포화 화합물(이하, 화합물(a2)이라고도 함)의 공중합체가 더욱 바람직하다. [A] 성분은, 용매 중에서 중합 개시제의 존재하, 화합물(a1) 및 화합물(a2)을 포함하는 불포화 화합물을 라디칼 중합함으로써 제조할 수 있다. 또한, [A] 성분의 제조에 있어서는, 화합물(a1) 및 화합물(a2)과 함께, 화합물(a3)로서 상기 화합물(a1) 및 화합물(a2) 이외의 불포화 화합물을 라디칼 중합해도 좋다. [A] 성분은, 화합물(a1)로부터 유도되는 구성 단위를, 화합물(a1) 및 화합물(a2)(및 임의로 화합물(a3))로부터 유도되는 반복 단위의 합계에 기초하여, 바람직하게는 5∼40질량%, 특히 바람직하게는 5∼25질량% 함유하고 있다. [A] 성분에 있어서의 화합물(a1)로부터 유도되는 구성 단위가 5∼40질량%일 때, 감방사선 감도, 현상성 및 감방사선성 수지 조성물의 보존 안정성 등의 제(諸)특성이 보다 높은 레벨에서 균형잡힌 감방사선성 수지 조성물이 얻어진다. As such alkali-soluble resin, the copolymer of (a1) unsaturated carboxylic acid and / or unsaturated carboxylic anhydride (henceforth a compound (a1)), and the other unsaturated compound copolymerizable with this is preferable, (a1) unsaturated carbon More preferred is a copolymer of an unsaturated compound (hereinafter also referred to as compound (a2)) containing an acid and / or an unsaturated carboxylic acid anhydride and (a2) an epoxy group-containing unsaturated compound. [A] component can be manufactured by radically polymerizing the unsaturated compound containing a compound (a1) and a compound (a2) in presence of a polymerization initiator in a solvent. In addition, in manufacture of component [A], you may radically polymerize unsaturated compounds other than the said compound (a1) and a compound (a2) as a compound (a3) with a compound (a1) and a compound (a2). The component (A) is preferably 5 to 5 based on the sum of the repeating units derived from the compound (a1) and the compound (a2) (and optionally the compound (a3)) of the structural unit derived from the compound (a1). 40 mass%, Especially preferably, it contains 5-25 mass%. When the structural unit derived from the compound (a1) in component (A) is 5-40 mass%, the agent characteristics, such as radiation sensitivity, developability, and storage stability of a radiation sensitive resin composition, are higher. A radiation sensitive resin composition balanced at a level is obtained.
화합물(a1)은, 라디칼 중합성을 갖는 불포화 카본산 및/또는 불포화 카본산 무수물이다. 화합물(a1)의 구체예로서는, 모노카본산, 디카본산, 디카본산의 무수물, 다가 카본산의 모노[(메타)아크릴로일옥시알킬]에스테르, 양(兩) 말단에 카복실기와 수산기를 갖는 폴리머의 모노(메타)아크릴레이트, 카복실기를 갖는 다환식 화합물 및 무수물 등을 들 수 있다. Compound (a1) is unsaturated carboxylic acid and / or unsaturated carboxylic acid anhydride which has radical polymerizability. Specific examples of the compound (a1) include monocarboxylic acid, dicarboxylic acid, anhydride of dicarboxylic acid, mono [(meth) acryloyloxyalkyl] ester of polycarboxylic acid, polymers having carboxyl groups and hydroxyl groups at both ends. The mono (meth) acrylate, the polycyclic compound which has a carboxyl group, an anhydride, etc. are mentioned.
이들 구체예는, 모노카본산으로서, 아크릴산, 메타크릴산, 크로톤산 등; 디카본산으로서, 말레산, 푸말산, 시트라콘산, 메사콘산, 이타콘산 등; 디카본산의 무수물로서, 상기 디카본산으로서 예시한 화합물의 무수물 등; 다가 카본산의 모노[(메타)아크릴로일옥시알킬]에스테르로서, 숙신산 모노[2-(메타)아크릴로일옥시에틸], 프탈산 모노[2-(메타)아크릴로일옥시에틸] 등; 양 말단에 카복실기와 수산기를 갖는 폴리머의 모노(메타)아크릴레이트로서, ω-카복시폴리카프로락톤모노(메타)아크릴레이트 등; 카복실기를 갖는 다환식 화합물 및 그 무수물로서, 5-카복시바이사이클로[2.2.1]헵토-2-엔, 5,6-디카복시바이사이클로[2.2.1]헵토-2-엔 등을 각각 들 수 있다. These specific examples are, as monocarboxylic acid, acrylic acid, methacrylic acid, crotonic acid and the like; As dicarboxylic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, etc .; As anhydride of dicarboxylic acid, Anhydride etc. of the compound illustrated as said dicarboxylic acid; As mono [(meth) acryloyloxyalkyl] ester of polyhydric carboxylic acid, Succinic acid mono [2- (meth) acryloyloxyethyl], Phthalic acid mono [2- (meth) acryloyloxyethyl], etc .; As a mono (meth) acrylate of the polymer which has a carboxyl group and a hydroxyl group at both ends, it is omega-carboxy polycaprolactone mono (meth) acrylate, etc .; Examples of the polycyclic compound having a carboxyl group and anhydrides thereof include 5-carboxybicyclo [2.2.1] hepto-2-ene, 5,6-dicarboxybicyclo [2.2.1] hepto-2-ene, and the like. have.
이들 화합물(a1) 중에서도, 모노카본산, 디카본산의 무수물이 바람직하게 사용된다. 특히, 아크릴산, 메타크릴산, 무수말레산이, 공중합 반응성, 알칼리 수용액에 대한 용해성 및 입수의 용이성때문에 바람직하게 사용된다. 이들 화합물 (a1)은, 단독으로 또는 2종류 이상을 조합하여 이용된다. Among these compounds (a1), anhydrides of monocarboxylic acid and dicarboxylic acid are preferably used. In particular, acrylic acid, methacrylic acid and maleic anhydride are preferably used because of copolymerization reactivity, solubility in aqueous alkali solution and ease of obtaining. These compounds (a1) are used individually or in combination of 2 or more types.
[A] 성분은, 화합물(a2)로부터 유도되는 구성 단위를, 화합물(a1) 및 화합물(a2)(및 임의로 화합물(a3))로부터 유도되는 반복 단위의 합계에 기초하여, 바람직하게는 10∼80질량%, 특히 바람직하게는 30∼80질량% 함유하고 있다. [A] 성분에 있어서의 화합물(a2)로부터 유도되는 구성 단위가 10∼80질량%일 때, 얻어지는 층간 절연막이나 마이크로 렌즈의 내열성, 표면 경도 및 박리액 내성이 양호하다. The component (A) is preferably 10 to 10 based on the sum of the structural units derived from the compound (a2) based on the sum of the repeating units derived from the compound (a1) and the compound (a2) (and optionally the compound (a3)). 80 mass%, Especially preferably, it contains 30-80 mass%. When the structural unit guide | induced from the compound (a2) in component (A) is 10-80 mass%, the heat resistance, surface hardness, and peeling liquid tolerance of the interlayer insulation film and microlens obtained are favorable.
화합물(a2)은 라디칼 중합성을 갖는 에폭시기 함유 불포화 화합물(옥세타닐기 함유 불포화 화합물을 포함함)이다. 에폭시기 함유 불포화 화합물의 구체예로서는, 아크릴산 글리시딜, 메타크릴산 글리시딜, α-에틸아크릴산 글리시딜, α-n-프로필아크릴산 글리시딜, α-n-부틸아크릴산 글리시딜, 아크릴산-3,4-에폭시부틸, 메타크릴산-3,4-에폭시부틸, 아크릴산-6,7-에폭시헵틸, 메타크릴산-6,7-에폭시헵틸, α-에틸아크릴산-6,7-에폭시헵틸, 비닐벤질 2,3-에폭시프로필에테르 등을 들 수 있다. Compound (a2) is an epoxy group-containing unsaturated compound (including oxetanyl group-containing unsaturated compound) having radical polymerizability. Specific examples of the epoxy group-containing unsaturated compound include glycidyl acrylate, glycidyl methacrylate, glycidyl α-ethyl acrylate, glycidyl α-n-propyl acrylate, glycidyl α-n-butyl acrylate and acrylic acid- 3,4-epoxybutyl, methacrylic acid-3,4-epoxybutyl, acrylic acid-6,7-epoxyheptyl, methacrylic acid-6,7-epoxyheptyl, α-ethylacrylic acid-6,7-epoxyheptyl, Vinyl benzyl 2,3-epoxypropyl ether and the like.
이들 에폭시기 함유 불포화 화합물 중에서도, 메타크릴산 글리시딜, 메타크릴산-6,7-에폭시헵틸, 비닐벤질 2,3-에폭시프로필에테르, 3,4-에폭시사이클로헥실메타크릴레이트 등이, 공중합 반응성 및, 얻어지는 층간 절연막 또는 마이크로 렌즈의 내열성과 표면 경도를 높이는 점에서 바람직하게 이용된다. Among these epoxy group-containing unsaturated compounds, methacrylic acid glycidyl, methacrylic acid-6,7-epoxyheptyl, vinylbenzyl 2,3-epoxypropyl ether, 3,4-epoxycyclohexyl methacrylate, and the like are copolymerizable and reactive. And the point which raises heat resistance and surface hardness of the obtained interlayer insulation film or microlens.
옥세타닐기 함유 불포화 화합물의 구체예로서는, 3-(아크릴로일옥시메틸)옥세탄, 3-(아크릴로일옥시메틸)-2-메틸옥세탄, 3-(아크릴로일옥시메틸)-3-에틸옥세탄, 3-(아크릴로일옥시메틸)-2-트리플루오로메틸옥세탄, 3-(아크릴로일옥시메틸)-2-펜타플루오로에틸옥세탄, 3-(아크릴로일옥시메틸)-2-페닐옥세탄, 3-(2-아크릴로일옥시에틸)옥세탄, 3-(2-아크릴로일옥시에틸)-2-에틸옥세탄, 3-(2-아크릴로일옥시에틸)-3-에틸옥세탄, 3-(2-아크릴로일옥시에틸)-2-페닐옥세탄, 3-(2-아크릴로일옥시에틸)-2,2-디플루오로옥세탄 등의 아크릴산 에스테르; Specific examples of the oxetanyl group-containing unsaturated compound include 3- (acryloyloxymethyl) oxetane, 3- (acryloyloxymethyl) -2-methyloxetane, and 3- (acryloyloxymethyl) -3- Ethyl oxetane, 3- (acryloyloxymethyl) -2-trifluoromethyloxetane, 3- (acryloyloxymethyl) -2-pentafluoroethyl oxetane, 3- (acryloyloxymethyl ) -2-phenyloxetane, 3- (2-acryloyloxyethyl) oxetane, 3- (2-acryloyloxyethyl) -2-ethyloxetane, 3- (2-acryloyloxyethyl Acrylic acid, such as) -3-ethyl oxetane, 3- (2-acryloyloxyethyl) -2-phenyloxetane, and 3- (2-acryloyloxyethyl) -2,2-difluorooxetane ester;
3-(메타크릴로일옥시메틸)옥세탄, 3-(메타크릴로일옥시메틸)-2-메틸옥세탄, 3-(메타크릴로일옥시메틸)-3-에틸옥세탄, 3-(메타크릴로일옥시메틸)-2-페닐옥세탄, 3-(2-메타크릴로일옥시에틸)옥세탄, 3-(2-메타크릴로일옥시에틸)-2-에틸옥세탄, 3-(2-메타크릴로일옥시에틸)-3-에틸옥세탄, 3-(2-메타크릴로일옥시에틸)-2-페닐옥세탄 등의 메타크릴산 에스테르 등을 들 수 있다. 이들 화합물(a2)은, 단독으로 또는 2종류 이상을 조합하여 이용된다. 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) -2-methyloxetane, 3- (methacryloyloxymethyl) -3-ethyloxetane, 3- ( Methacryloyloxymethyl) -2-phenyloxetane, 3- (2-methacryloyloxyethyl) oxetane, 3- (2-methacryloyloxyethyl) -2-ethyloxetane, 3- Methacrylic acid ester, such as (2-methacryloyloxyethyl) -3-ethyl oxetane and 3- (2-methacryloyloxyethyl) -2-phenyloxetane, etc. are mentioned. These compounds (a2) are used individually or in combination of 2 or more types.
화합물(a3)은, 상기의 화합물(a1) 및 화합물(a2) 이외로서, 라디칼 중합성을 갖는 불포화 화합물이라면 특별히 제한되는 것은 아니다. 화합물(a3)의 예로서는, 메타크릴산 쇄상 알킬에스테르, 메타크릴산 환상 알킬에스테르, 수산기를 갖는 메타크릴산 에스테르, 아크릴산 환상 알킬에스테르, 메타크릴산 아릴에스테르, 아크릴산 아릴에스테르, 불포화 디카본산 디에스테르, 바이사이클로 불포화 화합물, 말레이미드 화합물, 불포화 방향족 화합물, 공액 디엔, 테트라하이드로푸란 골격, 푸란 골격, 테트라하이드로피란 골격, 피란 골격, 하기식 (3)으로 나타나는 골격을 갖는 불포화 화합물, 하기식 (4)로 나타나는 페놀성 수산기 함유 불포화 화합물 및, 그 외의 불포화 화합물을 들 수 있다. The compound (a3) is not particularly limited as long as it is an unsaturated compound having radical polymerizability other than the compound (a1) and the compound (a2). Examples of the compound (a3) include methacrylic acid chain alkyl esters, methacrylic acid cyclic alkyl esters, methacrylic acid esters having hydroxyl groups, acrylic acid cyclic alkyl esters, methacrylic acid aryl esters, acrylic acid aryl esters, unsaturated dicarboxylic acid diesters, Bicyclo unsaturated compound, maleimide compound, unsaturated aromatic compound, conjugated diene, tetrahydrofuran skeleton, furan skeleton, tetrahydropyran skeleton, pyran skeleton, unsaturated compound having a skeleton represented by the following formula (3), the following formula (4) The phenolic hydroxyl group containing unsaturated compound represented by these, and other unsaturated compounds are mentioned.
(식 (3) 중, R5는 수소 원자 또는 메틸기이고, p는 2∼10의 정수임) (In formula (3), R <5> is a hydrogen atom or a methyl group, p is an integer of 2-10.)
(식 (4) 중, R6은 수소 원자 또는 메틸기이고, R7∼R11은 동일 또는 상이하고, 수소 원자, 하이드록실기 또는 탄소수 1∼4의 알킬기이고, B는 단결합, -COO-* 또는 -CONH-*이고, q는 0∼3의 정수이고, 단, R7∼R11의 적어도 1개는 하이드록실기이고, -COO-* 또는 -CONH-*에 있어서의 각각의 *의 결합손은 (CH2)q의 탄소와 결합하고, B가 단결합인 경우, q는 0임).(In formula (4), R <6> is a hydrogen atom or a methyl group, R <7> -R <11> is the same or different, is a hydrogen atom, a hydroxyl group, or a C1-C4 alkyl group, B is a single bond, -COO- * Or -CONH- * , q is an integer of 0-3, provided that at least 1 of R <7> -R <11> is a hydroxyl group, and each of * in -COO- * or -CONH- * The bond is bonded to the carbon of (CH 2 ) q and q is 0 when B is a single bond).
화합물(a3)의 구체예로서는, 메타크릴산 쇄상 알킬에스테르로서, 메틸메타크릴레이트, 에틸메타크릴레이트, n-부틸메타크릴레이트, sec-부틸메타크릴레이트, t-부틸메타크릴레이트, 2-에틸헥실메타크릴레이트, 이소데실메타크릴레이트, n-라우릴메타크릴레이트, 트리데실메타크릴레이트, n-스테아릴메타크릴레이트 등; 메타크릴산 환상 알킬에스테르로서, 사이클로헥실메타크릴레이트, 2-메틸사이클로헥실메타크릴레이트, 트리사이클로[5.2.1.02,6]데칸-8-일메타크릴레이트, 트리사이클로[5.2.1.02,6]데칸-8-일옥시에틸메타크릴레이트, 이소보르닐메타크릴레이트 등; 수산기를 갖는 메타크릴산 에스테르로서, 2-하이드록시에틸메타크릴레이트, 3-하이드록시프로필메타크릴레이트, 4-하이드록시부틸메타크릴레이트, 디에틸렌글리콜모노메타크릴레이트, 2,3-디하이드록시프로필메타크릴레이트, 2-메타크릴옥시에틸글리코사이드, 4-하이드록시페닐메타크릴레이트 등; 아크릴산 환상 알킬에스테르로서, 사이클로헥실아크릴레이트, 2-메틸사이클로헥실아크릴레이트, 트리사이클로[5.2.1.02,6]데칸-8-일아크릴레이트, 트리사이클로[5.2.1.02,6]데칸-8-일옥시에틸아크릴레이트, 이소보르닐아크릴레이트 등; 메타크릴산 아릴에스테르로서, 페닐메타크릴레이트, 벤질메타크릴레이트 등; As a specific example of a compound (a3), it is methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, t-butyl methacrylate, 2-ethyl as methacrylic acid linear alkylester. Hexyl methacrylate, isodecyl methacrylate, n-lauryl methacrylate, tridecyl methacrylate, n-stearyl methacrylate and the like; As methacrylic acid cyclic alkylesters, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, tricyclo [5.2.1.0 2,6 ] decane-8-yl methacrylate, tricyclo [5.2.1.0 2, 6 ] decane-8-yloxyethyl methacrylate, isobornyl methacrylate and the like; As methacrylic acid ester which has a hydroxyl group, 2-hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, diethylene glycol monomethacrylate, 2, 3- dihydride Oxypropyl methacrylate, 2-methacryloxyethyl glycoside, 4-hydroxyphenyl methacrylate, and the like; As acrylic acid cyclic alkylesters, cyclohexyl acrylate, 2-methylcyclohexyl acrylate, tricyclo [5.2.1.0 2,6 ] decane-8-ylacrylate, tricyclo [5.2.1.0 2,6 ] decane-8 -Yloxyethyl acrylate, isobornyl acrylate and the like; As methacrylic acid aryl ester, Phenyl methacrylate, benzyl methacrylate, etc .;
아크릴산 아릴에스테르로서, 페닐아크릴레이트, 벤질아크릴레이트 등; 불포화 디카본산 디에스테르로서, 말레산 디에틸, 푸마르산 디에틸, 이타콘산 디에틸 등; 바이사이클로 불포화 화합물로서, 바이사이클로[2.2.1]헵토-2-엔, 5-메틸바이사이클로[2.2.1]헵토-2-엔, 5-에틸바이사이클로[2.2.1]헵토-2-엔, 5-메톡시바이사이클로[2.2.1]헵토-2-엔, 5-에톡시바이사이클로[2.2.1]헵토-2-엔 등; As acrylic acid aryl ester, Phenyl acrylate, Benzyl acrylate, etc .; As unsaturated dicarboxylic acid diester, diethyl maleate, diethyl fumarate, diethyl itaconic acid, etc .; As bicyclo unsaturated compounds, bicyclo [2.2.1] hepto-2-ene, 5-methylbicyclo [2.2.1] hepto-2-ene, 5-ethylbicyclo [2.2.1] hepto-2-ene 5-methoxybicyclo [2.2.1] hepto-2-ene, 5-ethoxybicyclo [2.2.1] hepto-2-ene and the like;
말레이미드 화합물로서, N-페닐말레이미드, N-사이클로헥실말레이미드, N-벤질말레이미드, N-(4-하이드록시페닐)말레이미드, N-(4-하이드록시벤질)말레이미드 등; 불포화 방향족 화합물로서, 스티렌, α-메틸스티렌, p-메톡시스티렌 등; 공액 디엔으로서, 1,3-부타디엔, 이소프렌 등; 테트라하이드로푸란 골격을 함유하는 불포화 화합물로서, 테트라하이드로푸르푸릴(메타)아크릴레이트, 2-메타크릴로일옥시-프로피온산 테트라하이드로푸르푸릴에스테르, 3-(메타)아크릴로일옥시테트라하이드로푸란-2-온 등; 푸란 골격을 함유하는 불포화 화합물로서, 2-메틸-5-(3-푸릴)-1-펜텐-3-온, 푸르푸릴(메타)아크릴레이트, 1-푸란-2-부틸-3-엔-2-온 등; As a maleimide compound, N-phenylmaleimide, N-cyclohexyl maleimide, N-benzyl maleimide, N- (4-hydroxyphenyl) maleimide, N- (4-hydroxybenzyl) maleimide, etc .; As an unsaturated aromatic compound, Styrene, (alpha) -methylstyrene, p-methoxy styrene etc .; As a conjugated diene, 1, 3- butadiene, isoprene, etc .; As an unsaturated compound containing a tetrahydrofuran skeleton, tetrahydrofurfuryl (meth) acrylate, 2-methacryloyloxy-propionic acid tetrahydrofurfuryl ester, 3- (meth) acryloyloxy tetrahydrofuran-2 -On and the like; As an unsaturated compound containing a furan skeleton, 2-methyl-5- (3-furyl) -1-penten-3-one, furfuryl (meth) acrylate, 1-furan-2-butyl-3-ene-2 -On and the like;
테트라하이드로피란 골격을 함유하는 불포화 화합물로서, (테트라하이드로피란-2-일)메틸메타크릴레이트, 2,6-디메틸-8-(테트라하이드로피란-2-일옥시)-옥토-1-엔-3-온, 2-메타크릴산 테트라하이드로피란-2-일에스테르, 1-(테트라하이드로피란-2-옥시)-부틸-3-엔-2-온 등; 피란 골격을 함유하는 불포화 화합물로서, 4-(1,4-디옥사-5-옥소-6-헵테닐)-6-메틸-2-피란 등; 상기식 (3)으로 나타나는 골격을 함유하는 불포화 화합물로서, 폴리에틸렌글리콜(n=2∼10)모노(메타)아크릴레이트, 폴리프로필렌글리콜(n=2∼10)모노(메타)아크릴레이트 등을 들 수 있다. As an unsaturated compound containing tetrahydropyran skeleton, (tetrahydropyran-2-yl) methylmethacrylate, 2,6-dimethyl-8- (tetrahydropyran-2-yloxy) -octo-1-ene- 3-one, 2-methacrylic acid tetrahydropyran-2-yl ester, 1- (tetrahydropyran-2-oxy) -butyl-3-en-2-one, and the like; As an unsaturated compound containing a pyran skeleton, 4- (1, 4- dioxa-5-oxo-6-heptenyl) -6-methyl- 2-pyran etc .; Examples of the unsaturated compound containing a skeleton represented by the formula (3) include polyethylene glycol (n = 2 to 10) mono (meth) acrylate, polypropylene glycol (n = 2 to 10) mono (meth) acrylate, and the like. Can be.
또한, 페놀 골격을 함유하는 불포화 화합물로서, 상기식 (4)로 나타나는 화합물로부터, B와 q의 정의에 의해 하기식 (5)∼(9)로 나타나는 화합물 등을 들 수 있다. Moreover, as an unsaturated compound containing a phenol skeleton, the compound etc. which are represented by following formula (5)-(9) by definition of B and q are mentioned from the compound represented by said Formula (4).
(식 (5) 중, q는 1∼3의 정수이고, R6∼R11의 정의는 상기식 (4)에 있어서의 정의와 동일함) (In formula (5), q is an integer of 1-3, and the definition of R <6> -R <11> is the same as the definition in said Formula (4).)
(식 (6) 중, R6∼R11의 정의는 상기식 (4)에 있어서의 정의와 동일함)
(In formula (6), the definition of R <6> -R <11> is the same as the definition in said Formula (4).)
(식 (7) 중, q는 1∼3의 정수이고, R6∼R11의 정의는 상기식 (4)에 있어서의 정의와 동일함) (In formula (7), q is an integer of 1-3, and the definition of R <6> -R <11> is the same as the definition in said Formula (4).)
(식 (8) 중, R6∼R11의 정의는 상기식 (4)에 있어서의 정의와 동일함)
(In formula (8), the definition of R <6> -R <11> is the same as the definition in said Formula (4).)
(식 (9) 중, R6∼R11의 정의는 상기식 (4)에 있어서의 정의와 동일함).(In formula (9), the definition of R <6> -R <11> is the same as the definition in said Formula (4).).
그 외의 불포화 화합물의 예로서는, 스티렌, p-메톡시스티렌, 1,3-부타디엔, 아크릴로니트릴, 메타크릴로니트릴, 염화 비닐, 염화 비닐리덴, 아크릴아미드, 메타크릴아미드, 아세트산 비닐을 각각 들 수 있다. Examples of other unsaturated compounds include styrene, p-methoxystyrene, 1,3-butadiene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, and vinyl acetate, respectively. have.
이들 화합물(a3)의 예 중에서도, 메타크릴산 쇄상 알킬에스테르, 메타크릴산 환상 알킬에스테르, 말레이미드 화합물, 테트라하이드로푸란 골격, 푸란 골격, 테트라하이드로피란 골격, 피란 골격, 상기식 (3)으로 나타나는 골격을 갖는 불포화 화합물, 상기식 (4)로 나타나는 페놀성 수산기 함유 불포화 화합물이 바람직하게 이용된다. 이들 중에서도 특히, 스티렌, t-부틸메타크릴레이트, 트리사이클로[5.2.1.02,6]데칸-8-일메타크릴레이트, p-메톡시스티렌, 2-메틸사이클로헥실아크릴레이트, N-페닐말레이미드, N-사이클로헥실말레이미드, 테트라하이드로푸르푸릴(메타)아크릴레이트, 폴리에틸렌글리콜(n=2∼10)모노(메타)아크릴레이트, 3-(메타)아크릴로일옥시테트라하이드로푸란-2-온, 4-하이드록시벤질(메타)아크릴레이트, 4-하이드록시페닐(메타)아크릴레이트, o-하이드록시스티렌, p-하이드록시스티렌, α-메틸-p-하이드록시스티렌이, 공중합 반응성 및 알칼리 수용액에 대한 용해성의 점에서 바람직하다. 이들 화합물(a3)은, 단독으로 또는 2종류 이상을 조합하여 이용된다. Among the examples of these compounds (a3), methacrylic acid chain alkyl esters, methacrylic acid cyclic alkyl esters, maleimide compounds, tetrahydrofuran skeletons, furan skeletons, tetrahydropyran skeletons, pyran skeletons, represented by the formula (3) The unsaturated compound which has a skeleton, and the phenolic hydroxyl group containing unsaturated compound represented by said formula (4) are used preferably. Among them, styrene, t-butyl methacrylate, tricyclo [5.2.1.0 2,6 ] decane-8-yl methacrylate, p-methoxy styrene, 2-methylcyclohexyl acrylate and N-phenylmaleic Meade, N-cyclohexyl maleimide, tetrahydrofurfuryl (meth) acrylate, polyethylene glycol (n = 2-10) mono (meth) acrylate, 3- (meth) acryloyloxy tetrahydrofuran-2- On, 4-hydroxybenzyl (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, o-hydroxystyrene, p-hydroxystyrene, α-methyl-p-hydroxystyrene, copolymerization reactivity and It is preferable at the point of solubility to aqueous alkali solution. These compounds (a3) are used individually or in combination of 2 or more types.
본 발명에서 이용되는 [A] 성분은, 화합물(a3)로부터 유도되는 구성 단위를, 화합물(a1) 및 화합물(a2)(및 임의로 화합물(a3))로부터 유도되는 반복 단위의 합계에 기초하여, 바람직하게는 0∼60질량%, 특히 바람직하게는 5∼50질량% 함유해도 좋다. 이 구성 단위의 양이 60질량% 이하의 경우는, 공중합체의 분자량의 제어가 용이해져, 현상성, 감방사선 감도 등이 보다 높은 레벨에서 균형잡힌 감방사선성 수지 조성물이 얻어진다. [A] component used by this invention is a structural unit derived from compound (a3) based on the sum total of the repeating unit derived from compound (a1) and compound (a2) (and optionally compound (a3)), Preferably it is 0-60 mass%, Especially preferably, you may contain 5-50 mass%. When the quantity of this structural unit is 60 mass% or less, control of the molecular weight of a copolymer becomes easy, and the radiation sensitive resin composition balanced at the level where developability, radiation sensitivity, etc. are higher is obtained.
[A] 성분의 GPC(겔 투과 크로마토그래피)에 의한 폴리스티렌 환산 중량 평균 분자량(이하, 「Mw」라고 함)은, 바람직하게는 2×103∼1×105, 보다 바람직하게는 5×103∼5×104이다. [A] 성분의 Mw를 2×103 이상으로 함으로써, 포지티브형 감방사선성 수지 조성물의 현상 마진을 높여, 얻어지는 층간 절연막의 내열성의 저하를 억제할 수 있다. 한편, [A] 성분의 Mw를 1×105 이하로 함으로써, 우수한 방사선 감도 및 현상성을 얻을 수 있다. 또한, [A] 성분의 분자량 분포(이하, 「Mw/Mn」이라고 함)는, 바람직하게는 5.0 이하, 보다 바람직하게는 3.0 이하이다. [A] 성분의 Mw/Mn을 5.0 이하로 함으로써, 얻어지는 층간 절연막의 고도의 현상성을 확보할 수 있다. The polystyrene reduced weight average molecular weight (hereinafter referred to as "Mw") by GPC (gel permeation chromatography) of component [A], Preferably it is 2 * 10 <3> -1 * 10 <5> , More preferably, it is 5 * 10. 3 to 5 x 10 4 . By making Mw of a component (A) into 2 * 10 <3> or more, the image development margin of a positive radiation sensitive resin composition can be raised and the fall of the heat resistance of the interlayer insulation film obtained can be suppressed. On the other hand, by setting Mw of the component [A] to 1 × 10 5 or less, excellent radiation sensitivity and developability can be obtained. Moreover, the molecular weight distribution (henceforth "Mw / Mn") of a component [A] becomes like this. Preferably it is 5.0 or less, More preferably, it is 3.0 or less. By setting Mw / Mn of component [A] to 5.0 or less, the high developability of the interlayer insulation film obtained can be ensured.
[A] 성분을 제조하기 위한 중합 반응에 이용되는 용매로서는, 예를 들면, 디에틸렌글리콜디알킬에테르, 디프로필렌글리콜디알킬에테르, 프로필렌글리콜모노알킬에테르, 프로필렌글리콜모노알킬에테르아세테이트, 프로필렌글리콜모노알킬에테르프로피오네이트, 케톤류, 기타 에스테르류 등을 들 수 있다. As a solvent used for the polymerization reaction for manufacturing [A] component, For example, diethylene glycol dialkyl ether, dipropylene glycol dialkyl ether, propylene glycol monoalkyl ether, propylene glycol monoalkyl ether acetate, and propylene glycol mono Alkyl ether propionate, ketones, other ester, etc. are mentioned.
이들 용매로서는,As these solvents,
디에틸렌글리콜디알킬에테르로서, 예를 들면 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜에틸메틸에테르 등; As diethylene glycol dialkyl ether, For example, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, etc .;
디프로필렌글리콜디알킬에테르로서, 예를 들면 디프로필렌글리콜디메틸에테르, 디프로필렌글리콜디에틸에테르, 디프로필렌글리콜에틸메틸에테르 등; As dipropylene glycol dialkyl ether, For example, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol ethyl methyl ether, etc .;
프로필렌글리콜모노알킬에테르로서, 예를 들면 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 프로필렌글리콜모노프로필에테르, 프로필렌글리콜모노부틸에테르 등; As propylene glycol monoalkyl ether, For example, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, etc .;
프로필렌글리콜모노알킬에테르아세테이트로서, 예를 들면 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 프로필렌글리콜모노프로필에테르아세테이트 등; As propylene glycol monoalkyl ether acetate, For example, propylene glycol monomethyl ether acetate, a propylene glycol monoethyl ether acetate, a propylene glycol monopropyl ether acetate, etc .;
프로필렌글리콜모노알킬에테르프로피오네이트로서, 예를 들면 프로필렌글리콜모노메틸에테르프로피오네이트, 프로필렌글리콜모노에틸에테르프로피오네이트, 프로필렌글리콜모노프로필에테르프로피오네이트, 프로필렌글리콜모노부틸에테르프로피오네이트 등; Examples of the propylene glycol monoalkyl ether propionate include propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether propionate, propylene glycol monopropyl ether propionate, propylene glycol monobutyl ether propionate and the like;
케톤류로서, 예를 들면 메틸에틸케톤, 사이클로헥사논, 4-하이드록시-4-메틸-2-펜타논 등; As ketones, For example, methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl- 2-pentanone, etc .;
기타 에스테르류로서, 예를 들면 아세트산 메틸, 아세트산 에틸, 아세트산 프로필, 아세트산 부틸, 2-하이드록시프로피온산 에틸, 2-하이드록시-2-메틸프로피온산 메틸, 2-하이드록시-2-메틸프로피온산 에틸, 하이드록시아세트산 메틸, 하이드록시아세트산 에틸, 하이드록시아세트산 부틸, 락트산 메틸, 락트산 에틸, 락트산 프로필, 락트산 부틸, 3-하이드록시프로피온산 메틸, 3-하이드록시프로피온산 에틸, 3-하이드록시프로피온산 프로필, 3-하이드록시프로피온산 부틸, 2-하이드록시-3-메틸부탄산 메틸, 메톡시아세트산 메틸, 메톡시아세트산 에틸, 메톡시아세트산 프로필, 메톡시아세트산 부틸, 에톡시아세트산 메틸, 에톡시아세트산 에틸, 에톡시아세트산 프로필, 에톡시아세트산 부틸, 프로폭시아세트산 메틸, 프로폭시아세트산 에틸, 프로폭시아세트산 프로필, 프로폭시아세트산 부틸, 부톡시아세트산 메틸, 부톡시아세트산 에틸, 부톡시아세트산 프로필, 부톡시아세트산 부틸, 2-메톡시프로피온산 메틸, 2-메톡시프로피온산 에틸, 2-메톡시프로피온산 프로필, 2-메톡시프로피온산 부틸, 2-에톡시프로피온산 메틸, 2-에톡시프로피온산 에틸, 2-에톡시프로피온산 프로필, 2-에톡시프로피온산 부틸, 2-부톡시프로피온산 메틸, 2-부톡시프로피온산 에틸, 2-부톡시프로피온산 프로필, 2-부톡시프로피온산 부틸, 3-메톡시프로피온산 메틸, 3-메톡시프로피온산 에틸, 3-메톡시프로피온산 프로필, 3-메톡시프로피온산 부틸, 3-에톡시프로피온산 메틸, 3-에톡시프로피온산 에틸, 3-에톡시프로피온산 프로필, 3-에톡시프로피온산 부틸, 3-프로폭시프로피온산 메틸, 3-프로폭시프로피온산 에틸, 3-프로폭시프로피온산 프로필, 3-프로폭시프로피온산 부틸, 3-부톡시프로피온산 메틸, 3-부톡시프로피온산 에틸, 3-부톡시프로피온산 프로필, 3-부톡시프로피온산 부틸 등을 각각 들 수 있다. As other esters, for example, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, hydroxy Methyl hydroxyacetate, ethyl hydroxyacetate, hydroxyacetic acid butyl, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, 3-hydroxypropionate methyl, 3-hydroxypropionate ethyl, 3-hydroxypropionic acid propyl, 3-hydroxy Butyl oxypropionate, methyl 2-hydroxy-3-methylbutanoic acid, methyl methoxyacetic acid, ethyl methoxyacetic acid, methoxyacetic acid propyl, methoxyacetic acid butyl, ethoxyacetic acid methyl, ethoxyacetic acid ethyl, ethoxyacetic acid propyl Butyl ethoxyacetate, methyl propoxyacetate, ethyl propoxyacetate, propoxyacetic Propyl, Butyl Propoxy Acetate, Butoxy Acetic Acid, Ethyl Butoxy Acetate, Butoxy Acetic Acid, Butyl Butoxy Acetate, 2-Methoxypropionate, Ethyl 2-methoxypropionate, 2-methoxy Propionic Acid, 2- Butyl methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, propyl 2-ethoxypropionate, butyl 2-ethoxypropionate, methyl 2-butoxypropionate, ethyl 2-butoxypropionate, 2-part Propyl propyl propionate, butyl 2-butoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionic acid, butyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, 3-ethoxypropionic acid propyl, 3-ethoxypropionate butyl, 3-propoxypropionate methyl, 3-propoxypropionate ethyl, 3-propoxypropionic acid propyl Butyl 3-propoxypropionate, methyl 3-butoxypropionate, ethyl 3-butoxypropionate, propyl 3-butoxypropionate, butyl 3-butoxypropionate, and the like.
이들 용매 중, 디에틸렌글리콜디알킬에테르, 디프로필렌글리콜디알킬에테르, 프로필렌글리콜모노알킬에테르, 프로필렌글리콜모노알킬에테르아세테이트, 기타 에스테르류가 바람직하고, 디에틸렌글리콜디메틸에테르, 디프로필렌글리콜디메틸에테르, 디에틸렌글리콜에틸메틸에테르, 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노메틸에테르아세테이트, 3-메톡시프로피온산 메틸을 이용하는 것이 특히 바람직하다. Among these solvents, diethylene glycol dialkyl ether, dipropylene glycol dialkyl ether, propylene glycol monoalkyl ether, propylene glycol monoalkyl ether acetate and other esters are preferable, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, It is especially preferable to use diethylene glycol ethyl methyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and 3-methoxy propionate.
[A] 성분의 제조에 이용되는 중합 개시제로서는, 일반적으로 라디칼 중합 개시제로서 알려져 있는 것을 사용할 수 있다. 중합 개시제의 구체예로서는, 2,2'-아조비스이소부티로니트릴, 2,2'-아조비스-(2,4-디메틸발레로니트릴), 2,2'-아조비스-(4-메톡시-2,4-디메틸발레로니트릴) 등의 아조 화합물을 들 수 있다. As a polymerization initiator used for manufacture of [A] component, what is generally known as a radical polymerization initiator can be used. As a specific example of a polymerization initiator, 2,2'- azobisisobutyronitrile, 2,2'- azobis- (2, 4- dimethylvaleronitrile), 2,2'- azobis- (4-methoxy Azo compounds, such as -2, 4- dimethylvaleronitrile), are mentioned.
[A] 성분의 제조에 있어서는, 분자량을 조정하기 위해 분자량 조정제를 사용할 수 있다. 분자량 조정제의 구체예로서는, n-헥실머캅탄, n-옥틸머캅탄, n-도데실머캅탄, t-도데실머캅탄, 티오글리콜산, 펜타에리트리톨테트라키스(3-머캅토프로피오네이트) 등의 머캅탄; 디메틸잔토겐술피드, 디이소프로필잔토겐디술피드 등의 잔토겐류; 테르피놀렌, α-메틸스티렌다이머 등을 들 수 있다. In manufacture of component [A], in order to adjust molecular weight, a molecular weight modifier can be used. Specific examples of the molecular weight modifier include n-hexyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan, t-dodecyl mercaptan, thioglycolic acid, pentaerythritol tetrakis (3-mercaptopropionate), and the like. Mercaptans; Xanthogens, such as dimethyl xanthogen sulfide and diisopropyl xanthogen disulfide; Terpinolene, (alpha) -methylstyrene dimer, etc. are mentioned.
[B] 1,2-퀴논디아자이드 화합물(이하, [B] 성분이라고도 함)에 대해서, 이하에 설명한다. [B] 1,2-quinonediazide compound (hereinafter also referred to as component [B]) will be described below.
본 발명에서 이용되는 [B] 성분은, 방사선의 조사에 의해 카본산을 발생하는 1,2-퀴논디아자이드 화합물이다. 1,2-퀴논디아자이드 화합물로서, 페놀성 화합물 또는 알코올성 화합물(이하, 「모핵」이라고 함)과, 1,2-나프토퀴논디아자이드술폰산 할라이드와의 축합물을 이용할 수 있다. [B] component used by this invention is a 1, 2- quinonediazide compound which produces | generates a carboxylic acid by irradiation of a radiation. As a 1, 2- quinonediazide compound, the condensate of a phenolic compound or an alcoholic compound (henceforth "mother nucleus"), and 1, 2- naphthoquinone diazide sulfonic-acid halide can be used.
[B] 성분의 모핵의 예로서는, 트리하이드록시벤조페논, 테트라하이드록시벤조페논, 펜타하이드록시벤조페논, 헥사하이드록시벤조페논, (폴리하이드록시페닐)알칸, 그 외의 모핵을 들 수 있다. Examples of the mother nucleus of the component [B] include trihydroxybenzophenone, tetrahydroxybenzophenone, pentahydroxybenzophenone, hexahydroxybenzophenone, (polyhydroxyphenyl) alkane, and other mother nuclei.
이들 모핵의 구체예로서는, 트리하이드록시벤조페논으로서 2,3,4-트리하이드록시벤조페논, 2,4,6-트리하이드록시벤조페논 등; 테트라하이드록시벤조페논으로서, 2,2',4,4'-테트라하이드록시벤조페논, 2,3,4,3'-테트라하이드록시벤조페논, 2,3,4,4'-테트라하이드록시벤조페논, 2,3,4,2'-테트라하이드록시-4'-메틸벤조페논, 2,3,4,4'-테트라하이드록시-3'-메톡시벤조페논 등; 펜타하이드록시벤조페논으로서, 2,3,4,2',6'-펜타하이드록시벤조페논 등; 헥사하이드록시벤조페논으로서, 2,4,6,3',4',5'-헥사하이드록시벤조페논, 3,4,5,3',4',5'-헥사하이드록시벤조페논 등; (폴리하이드록시페닐)알칸으로서, 비스(2,4-디하이드록시페닐)메탄, 비스(p-하이드록시페닐)메탄, 트리(p-하이드록시페닐)메탄, 1,1,1-트리(p-하이드록시페닐)에탄, 비스(2,3,4-트리하이드록시페닐)메탄, 2,2-비스(2,3,4-트리하이드록시페닐)프로판, 1,1,3-트리스(2,5-디메틸-4-하이드록시페닐)-3-페닐프로판, 4,4'-[1-[4-[1-[4-하이드록시페닐]-1-메틸에틸]페닐]에틸리덴]비스페놀, 비스(2,5-디메틸-4-하이드록시페닐)-2-하이드록시페닐메탄 등;Specific examples of these mother cores include 2,3,4-trihydroxybenzophenone, 2,4,6-trihydroxybenzophenone, and the like as trihydroxybenzophenone; As tetrahydroxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2,3,4,3'-tetrahydroxybenzophenone, 2,3,4,4'-tetrahydroxy Benzophenone, 2,3,4,2'-tetrahydroxy-4'-methylbenzophenone, 2,3,4,4'-tetrahydroxy-3'-methoxybenzophenone and the like; As pentahydroxy benzophenone, 2,3,4,2 ', 6'- pentahydroxy benzophenone etc .; Examples of the hexahydroxybenzophenone include 2,4,6,3 ', 4', 5'-hexahydroxybenzophenone, 3,4,5,3 ', 4', 5'-hexahydroxybenzophenone and the like; As (polyhydroxyphenyl) alkanes, bis (2,4-dihydroxyphenyl) methane, bis (p-hydroxyphenyl) methane, tri (p-hydroxyphenyl) methane, 1,1,1-tri ( p-hydroxyphenyl) ethane, bis (2,3,4-trihydroxyphenyl) methane, 2,2-bis (2,3,4-trihydroxyphenyl) propane, 1,1,3-tris ( 2,5-dimethyl-4-hydroxyphenyl) -3-phenylpropane, 4,4 '-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] Bisphenol, bis (2,5-dimethyl-4-hydroxyphenyl) -2-hydroxyphenylmethane and the like;
또한, 위에서 예시한 모핵의 에스테르 결합을 아미드 결합으로 변경한 1,2-나프토퀴논디아자이드술폰산 아미드, 예를 들면 2,3,4-트리하이드록시벤조페논-1,2-나프토퀴논디아자이드-4-술폰산 아미드 등도 매우 적합하게 사용된다. In addition, 1,2-naphthoquinone diazide sulfonic acid amide in which the ester bond of the parent nucleus exemplified above is changed to an amide bond, for example, 2,3,4-trihydroxybenzophenone-1,2-naphthoquinonedia Zide-4-sulfonic acid amide etc. are also used suitably.
이들 모핵 중에서도 특히, 2,3,4,4'-테트라하이드록시벤조페논, 4,4'-[1-[4-[1-[4-하이드록시페닐]-1-메틸에틸]페닐]에틸리덴]비스페놀, 1,1,1-트리(p-하이드록시페닐)에탄이 바람직하다. Among these mother cores, especially 2,3,4,4'-tetrahydroxybenzophenone and 4,4 '-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethyl Preference is given to lidene] bisphenol and 1,1,1-tri (p-hydroxyphenyl) ethane.
한편, 1,2-나프토퀴논디아자이드술폰산 할라이드로서는, 1,2-나프토퀴논디아자이드술폰산 클로라이드가 바람직하다. 1,2-나프토퀴논디아자이드술폰산 클로라이드의 구체예로서는, 1,2-나프토퀴논디아자이드-4-술폰산 클로라이드 및 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드를 들 수 있다. 이 중에서도, 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드를 사용하는 것이 바람직하다. On the other hand, as 1,2-naphthoquinone diazide sulfonic-acid halide, 1, 2- naphthoquinone diazide sulfonic-acid chloride is preferable. Specific examples of 1,2-naphthoquinone diazide sulfonic acid chloride include 1,2-naphthoquinone diazide-4-sulfonic acid chloride and 1,2-naphthoquinone diazide-5-sulfonic acid chloride. Among these, it is preferable to use 1,2-naphthoquinone diazide-5-sulfonic acid chloride.
모핵과 1,2-나프토퀴논디아자이드술폰산 할라이드와의 축합 반응에 있어서는, 페놀성 화합물 또는 알코올성 화합물 중의 OH기 수에 대하여, 바람직하게는 30∼85몰%, 보다 바람직하게는 50∼70몰%에 상당하는 1,2-나프토퀴논디아자이드술폰산 할라이드를 이용할 수 있다. 축합 반응은 공지의 방법에 의해 실시할 수 있다. 이러한 축합 반응에 의해 얻어진 화합물로서, 4,4'-[1-[4-[1-[4-하이드록시페닐]-1-메틸에틸]페닐]에틸리덴]비스페놀(1.0몰)과 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드(2.0몰)와의 축합물, 1,1,1-트리(p-하이드록시페닐)에탄(1.0몰)과 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드(2.0몰)와의 축합물을 들 수 있다. In the condensation reaction between the mother nucleus and 1,2-naphthoquinonediazidesulfonic acid halide, the amount of OH groups in the phenolic compound or the alcoholic compound is preferably 30 to 85 mol%, more preferably 50 to 70 mol. 1,2-naphthoquinone diazide sulfonic acid halide corresponding to% can be used. Condensation reaction can be performed by a well-known method. As a compound obtained by such a condensation reaction, 4,4 '-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] bisphenol (1.0 mol) and 1,2 Condensates with naphthoquinonediazide-5-sulfonic acid chloride (2.0 mol), 1,1,1-tri (p-hydroxyphenyl) ethane (1.0 mol) and 1,2-naphthoquinonediazide-5 -Condensates with sulfonic acid chloride (2.0 mol).
[B] 성분의 1,2-퀴논디아자이드 화합물은, 단독으로 또는 2종 이상을 조합하여 이용할 수 있다. [B] 성분의 사용 비율은, [A] 성분의 알칼리 가용성 수지 100질량부에 대하여, 바람직하게는 5∼100질량부, 보다 바람직하게는 10∼50질량부이다. [B] 성분의 사용 비율이, [A] 성분의 알칼리 가용성 수지 100질량부에 대하여 5∼100질량부일 때, 현상액이 되는 알칼리 수용액에 대한 방사선의 조사 부분과 미(未)조사 부분과의 용해도의 차이가 커져, 양호한 패터닝이 가능해진다. 또한 얻어지는 층간 절연막의 내열성 및 내용제성이 양호해진다. The 1,2-quinonediazide compound of [B] component can be used individually or in combination of 2 or more types. The use ratio of the component (B) is preferably 5 to 100 parts by mass, and more preferably 10 to 50 parts by mass with respect to 100 parts by mass of the alkali-soluble resin of the component [A]. When the use ratio of the component [B] is 5 to 100 parts by mass with respect to 100 parts by mass of the alkali-soluble resin of the component [A], the solubility of the irradiated portion and the unirradiated portion of the radiation to the aqueous alkali solution to be a developing solution. The difference of becomes large, and favorable patterning is attained. Moreover, heat resistance and solvent resistance of the obtained interlayer insulation film become favorable.
일반식 (1)로 나타나는 화합물 [C](이하, [C] 성분이라고도 함)에 대해서, 이하에 설명한다. The compound [C] (henceforth also called a [C] component) represented by General formula (1) is demonstrated below.
(식 (1) 중, X는, 탄소수 6∼20의 2가의 직쇄상 지방족 탄화 수소기이고, Y1 및 Y2는, 각각 독립적으로, 단결합, 에스테르 결합, 아미드 결합 또는 우레탄 결합이고, R1 및 R2는, 각각 독립적으로, 수소 원자, 탄소수 1∼6의 알킬기, 술포기, 술포페닐기, 또는 하기식 (2)의 (i)∼(vi)의 어느 것으로 나타나는 기이고; 단, Y1 및 Y2가 동시에 단결합일 때, R1 및 R2가 수소원자 또는 탄소수 1∼6의 알킬기인 경우는 없음)(Wherein (1), X is a divalent straight-chain aliphatic hydrocarbon group having a carbon number of 6~20, Y 1 and Y 2 are, each independently, a single bond, an ester bond, an amide bond or a urethane bond, R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a sulfo group, a sulfophenyl group, or a group represented by any of (i) to (vi) of the following formula (2); When 1 and Y 2 are a single bond at the same time, R 1 and R 2 are not a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)
(2) (2)
(식 (i)∼(vi) 중, R3은, 수소 원자 또는 탄소수 1∼6의 알킬기이고, R4는, 수소 원자 또는 메틸기이고, m은, 0∼6의 정수이고, 단, 상기식 (1)의 Y1 또는 Y2가 단결합일 때, 이 Y1 또는 Y2와 연결하는 R3 또는 R4에 있어서의 m은 0임).(In formula (i)-(vi), R <3> is a hydrogen atom or a C1-C6 alkyl group, R <4> is a hydrogen atom or a methyl group, m is an integer of 0-6, and is a said formula When Y 1 or Y 2 in (1) is a single bond, m in R 3 or R 4 connecting with Y 1 or Y 2 is 0).
[C] 성분은, 1분자 중에 소수성을 나타내는 탄소수 6∼20의 알킬렌기와 그 양 말단 또는 한쪽 말단에 친수성기를 갖는 화합물이다. 이러한 화합물을 감방사선성 수지 조성물에 적용함으로써, 도막의 현상성 제어가 용이해져, 일정 현상 시간에 있어서의 과도한 현상이나 현상 부족에 인한 패턴의 결함을 개선할 수 있다. 또한, 에폭시기나 (메타)아크릴로일기 등의 반응성을 갖는 기를 포함하는 [C] 성분은, [A] 성분의 일부와 가열에 의해 반응하기 때문에, 막의 밀도를 향상시키는 것이 가능해진다. 막의 밀도에 의해, 각종 내성, 예를 들면, 산, 알칼리 수용액, 유기 용매나 에칭 가스 등에 의한 내성이 향상된다. 특히, 드라이 에칭시의 에칭 가스에 대한 패턴 결손의 억제에 현저한 효과를 발휘할 수 있다. [C] component is a compound which has a C6-C20 alkylene group which shows hydrophobicity in 1 molecule, and a hydrophilic group in the both terminal or one terminal. By applying such a compound to a radiation sensitive resin composition, developability control of a coating film becomes easy, and the defect of the pattern resulting from excessive image development or lack of image development in fixed developing time can be improved. Moreover, since the [C] component containing groups which have reactivity, such as an epoxy group and a (meth) acryloyl group, reacts with a part of [A] component by heating, it becomes possible to improve the density of a film | membrane. By the density of the film, various resistances, for example, resistance by an acid, an aqueous alkali solution, an organic solvent, an etching gas, or the like is improved. In particular, a remarkable effect can be exerted on suppression of the pattern defect with respect to the etching gas at the time of dry etching.
1분자 중에 소수성을 나타내는 탄소수 5 이하의 경우, 양 말단 또는 한쪽 말단의 친수성 성능이 강하게 발현되기 때문에, 현상성을 과잉으로 촉진하는 경향에 있고, 반대로 탄소수가 21 이상의 경우, 현상성을 저하시키는 경향에 있어, 현상 잔사 발생 등의 원인이 된다. In the case of carbon number 5 or less showing hydrophobicity in one molecule, since hydrophilic performance of both ends or one end is strongly expressed, there is a tendency to excessively develop the developability, and on the contrary, when carbon number is 21 or more, the tendency to decrease developability. In this case, development residues are caused.
[C] 성분의 사용량은, 단독으로 혹은 2종 이상을 조합하여 사용할 수 있다. 당해 감방사선성 수지 조성물에 있어서 [C] 성분을 사용하는 경우의 양은, [A] 성분 100질량부에 대하여, 바람직하게는 0.01∼20질량부, 더욱 바람직하게는 0.05∼15질량부이다. [C] 성분의 배합량을 0.01∼20질량부로 함으로써, 현상성, 기체(基體)와의 밀착성, 드라이 에칭시의 에칭 가스에 대한 패턴 결손의 억제 등에 효과가 있다. The usage-amount of [C] component can be used individually or in combination of 2 or more types. The quantity in the case of using [C] component in the said radiation sensitive resin composition becomes like this. Preferably it is 0.01-20 mass parts, More preferably, it is 0.05-15 mass parts with respect to 100 mass parts of [A] components. By setting the blending amount of the component (C) to 0.01 to 20 parts by mass, it is effective in developing, adhesiveness with a substrate, suppression of pattern defects with respect to etching gas during dry etching, and the like.
이러한 [C] 성분의 구체예로서는, 이하에 나타내는 화합물을 들 수 있지만, 이하의 예에 한정되는 것은 아니다. 예를 들면, 불포화 결합을 포함해도 좋은 탄소수 6∼20의 알킬렌기를 갖는 지방산으로서는, 카프릴산(caprylic acid), 펠라르곤산(pelargonic acid), 카프르산(capric acid), 라우르산, 미리스트산, 펜타데실산, 팔미트산, 팔미톨레산, 마르가르산(margaric acid), 스테아르산, 올레산, 바크센산(vaccenic acid), 리놀레산(linoleic acid), 리놀렌산(linolenic acid), 엘레오스테아르산(eleostearic acid), 투베르쿨로스테아르산(tuberculostearic acid), 아라키드산(arachidic acid), 아라키돈산(arachidonic acid), 데칸 2산, 헥사데칸 2산, 헵타데칸 2산, 노나데칸 2산, 옥타데칸 2산, 펜타데칸 2산, 트리데칸 2산, 테트라데칸 2산, 스테아르산 글리시딜, 팔미트산 글리시딜, cis-9-헥사데센산, 엘라이드산(elaidic acid) 등을 들 수 있다. Although the compound shown below is mentioned as a specific example of such [C] component, It is not limited to the following example. For example, examples of the fatty acid having an alkylene group having 6 to 20 carbon atoms that may contain an unsaturated bond include caprylic acid, pelargonic acid, capric acid, lauric acid, Myristic acid, pentadecyl acid, palmitic acid, palmitoleic acid, margaric acid, stearic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, eleostere Eleostearic acid, tuberculostearic acid, arachidic acid, arachidonic acid, decane diacid, hexadecane diacid, heptadecane diacid, nonadecan 2 Acids, octadecane diacids, pentadecane diacids, tridecane diacids, tetradecane diacids, stearic acid glycidyl, palmitic acid glycidyl, cis-9-hexadecenoic acid, elaidic acid Etc. can be mentioned.
알코올로서는, n-헥실알코올, n-헵틸알코올, n-옥틸알코올, n-노닐알코올, n-데실알코올, n-운데실알코올, n-도데실알코올, n-헵타데칸올, n-옥타데칸올, 1,8-옥틸디알코올, 1,9-노닐디알코올, 1,10-데실디알코올, 1,11-운데실디알코올, 1,12-도데실디알코올, trans-9-옥타데센올, 올레일알코올, trans-2-도데센올 등을 들 수 있다. Examples of the alcohol include n-hexyl alcohol, n-heptyl alcohol, n-octyl alcohol, n-nonyl alcohol, n-decyl alcohol, n-undecyl alcohol, n-dodecyl alcohol, n-heptadecanol, n-octadecane Ol, 1,8-octyldialcohol, 1,9-nonyldialcohol, 1,10-decyldialcohol, 1,11-undecyldialcohol, 1,12-dodecyldialcohol, trans-9-octadecenol, Oleyl alcohol, trans-2-dodecenol, and the like.
에스테르류로서는, 카프릴산 메틸, 카프릴산 에틸, 펠라르곤산 메틸, 펠라르곤산 에틸, 카프르산 메틸, 카프르산 에틸, 라우르산 메틸, 라우르산 에틸, 미리스트산 메틸, 펜타데실산 메틸, 팔미트산 메틸, 팔미톨레산 메틸, 마르가르산 메틸, 스테아르산 메틸, 올레산 메틸, 바크센산 메틸, 리놀산 메틸, 리놀렌산 메틸, 엘레오스테아르산 메틸, 투베르쿨로스테아르산 메틸, 아라키드산 메틸, 아라키돈산 메틸 등을 들 수 있다. Examples of the esters include methyl caprylate, ethyl caprylate, methyl pelargonate, ethyl pelargonate, methyl capric acid, ethyl caprate, methyl laurate, ethyl laurate, methyl myristic acid and penta. Methyl decylate, methyl palmitic acid, methyl palmitoleic acid, methyl margarate, methyl stearate, methyl oleate, methyl vaxate, methyl linoleate, linolenic acid, methyl eleostearate, methyl tuberculostearate, Methyl arachidate, methyl arachidonic acid, etc. are mentioned.
그 외에, 1-도데칸술폰산, 1-운데칸술폰산, 1-노난술폰산, 도데실벤젠술폰산, 1-에폭시테트라데칸, 1-에폭시헥사데칸, 1-에폭시데칸, 1,2-에폭시테트라데칸, 1,2-에폭시헥사데칸, 1,2-에폭시데칸, 1,2-에폭시헵타데칸, 1,2-에폭시노나데칸, 1,2-에폭시옥타데칸, 1,2-에폭시펜타데칸, 1,2-옥세타닐테트라데칸, 1,2-옥세타닐헥사데칸, 1,2-옥세타닐데칸, 1,2-옥세타닐헵타데칸, 1-(3,4-에폭시사이클로헥실)-테트라데칸, 1,2-디(3,4-에폭시사이클로헥실)-테트라데칸, 1,2-디(3,4-에폭시사이클로헥실)-헥사데칸 등을 들 수 있다. In addition, 1-dodecanesulfonic acid, 1-undecanesulfonic acid, 1-nonanesulfonic acid, dodecylbenzenesulfonic acid, 1-epoxytetedecane, 1-epoxyhexadecane, 1-epoxydecane, 1,2-epoxytedecane, 1,2-epoxyhexadecane, 1,2-epoxydecane, 1,2-epoxyheptadecane, 1,2-epoxynonadecane, 1,2-epoxyoctadecane, 1,2-epoxypentadedecane, 1,2 Oxetanyl tetradecane, 1,2-oxetanylhexadecane, 1,2-oxetanyldecane, 1,2-oxetanylheptadecane, 1- (3,4-epoxycyclohexyl) -tetradecane And 1,2-di (3,4-epoxycyclohexyl) -tedecane, 1,2-di (3,4-epoxycyclohexyl) -hexadecane and the like.
또한, 이소시아네이트기를 갖는 화합물과 수산기를 갖는 화합물과의 반응에서 얻어지는 우레탄기를 갖는 화합물, 아미노기를 갖는 화합물과 카복실기를 갖는 화합물과의 반응에서 얻어지는 아미드기를 갖는 화합물, 카복실기를 갖는 화합물과 수산기를 갖는 화합물과의 반응에서 얻어지는 에스테르기를 갖는 화합물 등을 들 수 있고, 구체적으로는 하기식 (10)∼(13)에 나타내는 화합물 등을 들 수 있다. Moreover, the compound which has a urethane group obtained by reaction of the compound which has an isocyanate group, and the compound which has a hydroxyl group, the compound which has an amide group obtained by reaction of the compound which has an amino group, and the compound which has a carboxyl group, the compound which has a carboxyl group, and the compound which has a hydroxyl group, The compound etc. which have an ester group obtained by reaction of these are mentioned, Specifically, the compound etc. shown by following formula (10)-(13) are mentioned.
상기 [C] 성분 중, 특히 패턴 형상, 내드라이 에칭성의 관점에서, 팔미트산, 스테아르산, 테트라데칸 2산, 1-도데칸올, 1,12-도데칸디올, 1,2-에폭시테트라데칸, 1,2-에폭시헥사데칸, 스테아르산 글리시딜, 1,3-에폭시-2-에틸-2-도데칸, 1-도데칸술폰산 등이 바람직하다. Among the above-mentioned [C] components, especially from the viewpoint of pattern shape and dry etching resistance, palmitic acid, stearic acid, tetradecane diacid, 1-dodecanol, 1,12-dodecanediol, 1,2-epoxytetedecane , 1,2-epoxyhexadecane, glycidyl stearate, 1,3-epoxy-2-ethyl-2-dodecane, 1-dodecanesulfonic acid and the like are preferable.
상기 [C] 성분의 화합물은, 탄소수 8∼18의 지방산 및 탄소수 8∼18의 알킬기를 갖는 에폭시 화합물의 적어도 한쪽을 포함한다.The compound of the said [C] component contains at least one of the C8-C18 fatty acid and the epoxy compound which has a C8-C18 alkyl group.
그 외의 임의 성분Any other ingredients
당해 포지티브형 감방사선성 수지 조성물은, 상기의 [A] 및 [B] 및 [C]성분에 더하여, 소기의 효과를 손상시키지 않는 범위에서 필요에 따라서, [D] 감열성 산 생성 화합물 또는 감열성 염기 생성 화합물, [E] 적어도 1개의 에틸렌성 불포화 2중 결합을 갖는 중합성 화합물, [F] 계면 활성제, [G] 밀착 조제 및 [H] 라디칼 포착제를 함유할 수 있다. In addition to the above-mentioned [A], [B], and [C] component, the said positive radiation sensitive resin composition is a [D] thermosensitive acid production compound or a sensitivity as needed in the range which does not impair a desired effect. A thermal base generating compound, [E] a polymerizable compound having at least one ethylenically unsaturated double bond, a [F] surfactant, an [G] adhesion aid and a [H] radical scavenger.
[D] 성분의 감열성 산 생성 화합물 또는 감열성 염기 생성 화합물은, 열을 가함으로써 산성 활성 물질 또는 염기성 활성 물질을 방출할 수 있는 화합물이라고 정의된다. 이러한 감열성 산 생성 화합물 또는 감열성 염기 생성 화합물은, 얻어지는 층간 절연막의 내열성이나 내용제성을 향상시키기 위해, 당해 포지티브형 감방사선성 수지 조성물에 가할 수 있다. The thermosensitive acid generating compound or thermosensitive base generating compound of the component [D] is defined as a compound capable of releasing an acidic active substance or a basic active substance by applying heat. Such a thermosensitive acid generating compound or a thermosensitive base generating compound can be added to the positive radiation-sensitive resin composition in order to improve heat resistance and solvent resistance of the resulting interlayer insulating film.
[D] 성분의 감열성 산 생성 화합물로서는, 디페닐요오도늄염, 트리페닐술포늄염 및, 술포늄염, 벤조티아조늄염, 암모늄염, 포스포늄염, 테트라하이드로티오페늄염 등의 오늄염을 들 수 있다. Examples of the thermosensitive acid-producing compound of the component [D] include onium salts such as diphenyl iodonium salt, triphenylsulfonium salt, sulfonium salt, benzothiazonium salt, ammonium salt, phosphonium salt and tetrahydrothiophenium salt. have.
디페닐요오도늄염의 예로서는, 디페닐요오도늄테트라플루오로보레이트, 디페닐요오도늄헥사플루오로포스포네이트, 디페닐요오도늄헥사플루오로아르세네이트, 디페닐요오도늄트리플루오로메탄술포네이트, 디페닐요오도늄트리플루오로아세테이트, 디페닐요오도늄-p-톨루엔술포네이트, 디페닐요오도늄부틸트리스(2,6-디플루오로페닐)보레이트, 4-메톡시페닐페닐요오도늄테트라플루오로보레이트, 비스(4-t-부틸페닐)요오도늄테트라플루오로보레이트, 비스(4-t-부틸페닐)요오도늄헥사플루오로아르세네이트, 비스(4-t-부틸페닐)요오도늄트리플루오로메탄술포네이트, 비스(4-t-부틸페닐)요오도늄트리플루오로아세테이트, 비스(4-t-부틸페닐)요오도늄-p-톨루엔술포네이트, 비스(4-t-부틸페닐)요오도늄캠퍼술폰산 등을 들 수 있다. Examples of the diphenyl iodonium salt include diphenyl iodonium tetrafluoroborate, diphenyl iodonium hexafluorophosphonate, diphenyl iodonium hexafluoroarsenate, and diphenyl iodonium trifluoro. Methanesulfonate, diphenyliodonium trifluoroacetate, diphenyliodonium-p-toluenesulfonate, diphenyliodonium butyltris (2,6-difluorophenyl) borate, 4-methoxyphenyl Phenyl iodonium tetrafluoroborate, bis (4-t-butylphenyl) iodonium tetrafluoroborate, bis (4-t-butylphenyl) iodonium hexafluoroarsenate, bis (4-t -Butylphenyl) iodonium trifluoromethanesulfonate, bis (4-t-butylphenyl) iodonium trifluoroacetate, bis (4-t-butylphenyl) iodonium-p-toluenesulfonate, Bis (4-t- butylphenyl) iodonium camphor sulfonic acid etc. are mentioned.
트리페닐술포늄염의 예로서는, 트리페닐술포늄트리플루오로메탄술포네이트, 트리페닐술포늄캠퍼술폰산, 트리페닐술포늄테트라플루오로보레이트, 트리페닐술포늄트리플루오로아세테이트, 트리페닐술포늄-p-톨루엔술포네이트, 트리페닐술포늄부틸트리스(2,6-디플루오로페닐)보레이트 등을 들 수 있다. Examples of the triphenylsulfonium salt include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium camphorsulfonic acid, triphenylsulfonium tetrafluoroborate, triphenylsulfonium trifluoroacetate, and triphenylsulfonium-p- Toluenesulfonate, triphenylsulfonium butyl tris (2,6-difluorophenyl) borate, and the like.
술포늄염의 예로서는, 알킬술포늄염, 벤질술포늄염, 디벤질술포늄염, 치환 벤질술포늄염 등을 들 수 있다. Examples of the sulfonium salt include alkyl sulfonium salts, benzyl sulfonium salts, dibenzyl sulfonium salts, substituted benzyl sulfonium salts, and the like.
이들 술포늄염으로서는,As these sulfonium salts,
알킬술포늄염으로서, 예를 들면 4-아세톡시페닐디메틸술포늄헥사플루오로안티모네이트, 4-아세톡시페닐디메틸술포늄헥사플루오로아르세네이트, 디메틸-4-(벤질옥시카보닐옥시)페닐술포늄헥사플루오로안티모네이트, 디메틸-4-(벤조일옥시)페닐술포늄헥사플루오로안티모네이트, 디메틸-4-(벤조일옥시)페닐술포늄헥사플루오로아르세네이트, 디메틸-3-클로로-4-아세톡시페닐술포늄헥사플루오로안티모네이트 등; As the alkylsulfonium salt, for example, 4-acetoxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate, dimethyl-4- (benzyloxycarbonyloxy) phenyl Sulfonium hexafluoroantimonate, dimethyl-4- (benzoyloxy) phenylsulfonium hexafluoroantimonate, dimethyl-4- (benzoyloxy) phenylsulfonium hexafluoroarsenate, dimethyl-3-chloro 4-acetoxyphenylsulfonium hexafluoroantimonate, etc .;
벤질술포늄염으로서, 예를 들면 벤질-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, 벤질-4-하이드록시페닐메틸술포늄헥사플루오로포스페이트, 4-아세톡시페닐벤질메틸술포늄헥사플루오로안티모네이트, 벤질-4-메톡시페닐메틸술포늄헥사플루오로안티모네이트, 벤질-2-메틸-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, 벤질-3-클로로-4-하이드록시페닐메틸술포늄헥사플루오로아르세네이트, 4-메톡시벤질-4-하이드록시페닐메틸술포늄헥사플루오로포스페이트 등; As the benzylsulfonium salt, for example, benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, benzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate, 4-acetoxyphenylbenzylmethylsulfonium hexa Fluoroantimonate, benzyl-4-methoxyphenylmethylsulfonium hexafluoroantimonate, benzyl-2-methyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, benzyl-3-chloro- 4-hydroxyphenylmethylsulfonium hexafluoroarsenate, 4-methoxybenzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate, etc .;
디벤질술포늄염으로서, 예를 들면 디벤질-4-하이드록시페닐술포늄헥사플루오로안티모네이트, 디벤질-4-하이드록시페닐술포늄헥사플루오로포스페이트, 4-아세톡시페닐디벤질술포늄헥사플루오로안티모네이트, 디벤질-4-메톡시페닐술포늄헥사플루오로안티모네이트, 디벤질-3-클로로-4-하이드록시페닐술포늄헥사플루오로아르세네이트, 디벤질-3-메틸-4-하이드록시-5-t-부틸페닐술포늄헥사플루오로안티모네이트, 벤질-4-메톡시벤질-4-하이드록시페닐술포늄헥사플루오로포스페이트 등; As the dibenzylsulfonium salt, for example, dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate, dibenzyl-4-hydroxyphenylsulfonium hexafluorophosphate, 4-acetoxyphenyl dibenzylsulfonium Hexafluoroantimonate, dibenzyl-4-methoxyphenylsulfonium hexafluoroantimonate, dibenzyl-3-chloro-4-hydroxyphenylsulfonium hexafluoroarsenate, dibenzyl-3- Methyl-4-hydroxy-5-t-butylphenylsulfonium hexafluoroantimonate, benzyl-4-methoxybenzyl-4-hydroxyphenylsulfonium hexafluorophosphate and the like;
치환 벤질술포늄염으로서, 예를 들면, p-클로로벤질-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, p-니트로벤질-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, p-클로로벤질-4-하이드록시페닐메틸술포늄헥사플루오로포스페이트, p-니트로벤질-3-메틸-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, 3,5-디클로로벤질-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, o-클로로벤질-3-클로로-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트 등을 각각 들 수 있다. As the substituted benzylsulfonium salt, for example, p-chlorobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, p-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, p-chlorobenzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate, p-nitrobenzyl-3-methyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, 3,5-dichlorobenzyl-4 -Hydroxyphenylmethylsulfonium hexafluoroantimonate, o-chlorobenzyl-3-chloro-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, etc. are mentioned, respectively.
벤조티아조늄염의 예로서는, 3-벤질벤조티아조늄헥사플루오로안티모네이트, 3-벤질벤조티아조늄헥사플루오로포스페이트, 3-벤질벤조티아조늄테트라플루오로보레이트, 3-(p-메톡시벤질)벤조티아조늄헥사플루오로안티모네이트, 3-벤질-2-메틸티오벤조티아조늄헥사플루오로안티모네이트, 3-벤질-5-클로로벤조티아조늄헥사플루오로안티모네이트 등을 들 수 있다. Examples of the benzothiazonium salts include 3-benzylbenzothiazonium hexafluoroantimonate, 3-benzylbenzothiazonium hexafluorophosphate, 3-benzylbenzothiazonium tetrafluoroborate, 3- (p-methoxybenzyl) Benzothiazonium hexafluoroantimonate, 3-benzyl-2-methylthiobenzothiazonium hexafluoroantimonate, 3-benzyl-5-chlorobenzothiazonium hexafluoroantimonate, etc. are mentioned.
테트라하이드로티오페늄염의 예로서는, 1-(4-n-부톡시나프탈렌-1-일)테트라하이드로티오페늄트리플루오로메탄술포네이트, 1-(4-n-부톡시나프탈렌-1-일)테트라하이드로티오페늄노나플루오로-n-부탄술포네이트, 1-(4-n-부톡시나프탈렌-1-일)테트라하이드로티오페늄-1,1,2,2-테트라플루오로-2-(노르보르난-2-일)에탄술포네이트, 1-(4-n-부톡시나프탈렌-1-일)테트라하이드로티오페늄-2-(5-t-부톡시카보닐옥시바이사이클로[2.2.1]헵탄-2-일)-1,1,2,2-테트라플루오로에탄술포네이트, 1-(4-n-부톡시나프탈렌-1-일)테트라하이드로티오페늄-2-(6-t-부톡시카보닐옥시바이사이클로[2.2.1]헵탄-2-일)-1,1,2,2-테트라플루오로에탄술포네이트, 1-(4,7-디부톡시-1-나프탈레닐)테트라하이드로티오페늄트리플루오로메탄술포네이트 등을 들 수 있다. Examples of tetrahydrothiophenium salts include 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiopheniumtrifluoromethanesulfonate and 1- (4-n-butoxynaphthalen-1-yl) Tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium-1,1,2,2-tetrafluoro-2- (Norbornan-2-yl) ethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium-2- (5-t-butoxycarbonyloxybicyclo [2.2 .1] heptan-2-yl) -1,1,2,2-tetrafluoroethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium-2- (6 -t-butoxycarbonyloxybicyclo [2.2.1] heptan-2-yl) -1,1,2,2-tetrafluoroethanesulfonate, 1- (4,7-dibutoxy-1-naph Thalenyl) tetrahydrothiophenium trifluoromethanesulfonate, etc. are mentioned.
이들 감열성 산 생성 화합물의 시판품으로서는, 산에이드(SANAID) SI-L85, 동(同) SI-L110, 동 SI-L145, 동 SI-L150, 동 SI-L160(산신카가쿠코교 가부시키가이샤 제조) 등을 들 수 있다. Commercially available products of these thermosensitive acid-producing compounds include SANID SI-L85, SI-L110, SI-L145, SI-L150, and SI-L160 (manufactured by Sanshin Kagaku Kogyo Co., Ltd.). ), And the like.
이들 감열성 산 생성 화합물 중에서도, 얻어지는 층간 절연막의 내열성 향상의 관점에서, 트리페닐술포늄염, 술포늄염, 벤조티아조늄염 및, 테트라하이드로티오페늄염이 바람직하게 이용된다. 이 중에서도 특히, 트리페닐술포늄트리플루오로메탄술포네이트, 트리페닐술포늄캠퍼술폰산, 4-아세톡시페닐디메틸술포늄헥사플루오로아르세네이트, 벤질-4-하이드록시페닐메틸술포늄헥사플루오로안티모네이트, 4-아세톡시페닐벤질메틸술포늄헥사플루오로안티모네이트, 디벤질-4-하이드록시페닐술포늄헥사플루오로안티모네이트, 3-벤질벤조티아조늄헥사플루오로안티모네이트, 벤질-4-하이드록시페닐메틸술포늄헥사플루오로포스페이트, 1-(4,7-디부톡시-1-나프탈레닐)테트라하이드로티오페늄트리플루오로메탄술포네이트가 바람직하게 이용된다. Among these thermosensitive acid generating compounds, triphenylsulfonium salt, sulfonium salt, benzothiazonium salt and tetrahydrothiophenium salt are preferably used from the viewpoint of improving the heat resistance of the resulting interlayer insulating film. Among them, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium camphorsulfonic acid, 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate and benzyl-4-hydroxyphenylmethylsulfonium hexafluoro Antimonate, 4-acetoxyphenylbenzylmethylsulfonium hexafluoroantimonate, dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate, 3-benzylbenzothiazonium hexafluoroantimonate, Benzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate and 1- (4,7-dibutoxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate are used preferably.
[D] 성분의 감열성 염기 생성 화합물의 예로서는, 2-니트로벤질사이클로헥실카바메이트, [[(2,6-디니트로벤질)옥시]카보닐]사이클로헥실아민, N-(2-니트로벤질옥시카보닐)피롤리딘, 비스[[(2-니트로벤질)옥시]카보닐]헥산-1,6-디아민, 트리페닐메탄올, O-카바모일하이드록시아미드, O-카바모일옥심, 4-(메틸티오벤조일)-1-메틸-1-모르폴리노에탄, (4-모르폴리노벤조일)-1-벤질-1-디메틸아미노프로판, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-부타논, 헥사아민코발트(III)트리스(트리페닐메틸보레이트) 등을 들 수 있다. 이들 [D] 성분의 감열성 염기 생성 화합물 중에서도, 얻어지는 층간 절연막의 내열성의 향상의 관점에서, 2-니트로벤질사이클로헥실카바메이트 및 O-카바모일하이드록시아미드가 특히 바람직하다. Examples of the thermosensitive base-forming compound of the component [D] include 2-nitrobenzylcyclohexylcarbamate, [[(2,6-dinitrobenzyl) oxy] carbonyl] cyclohexylamine, N- (2-nitrobenzyloxy Carbonyl) pyrrolidine, bis [[(2-nitrobenzyl) oxy] carbonyl] hexane-1,6-diamine, triphenylmethanol, O-carbamoylhydroxyamide, O-carbamoyloxime, 4- ( Methylthiobenzoyl) -1-methyl-1-morpholinoethane, (4-morpholinobenzoyl) -1-benzyl-1-dimethylaminopropane, 2-benzyl-2-dimethylamino-1- (4-morph Polynophenyl) -butanone, hexaamine cobalt (III) tris (triphenylmethyl borate), etc. are mentioned. Among the thermosensitive base-forming compounds of the component [D], 2-nitrobenzylcyclohexyl carbamate and O-carbamoylhydroxyamide are particularly preferable from the viewpoint of improving the heat resistance of the resulting interlayer insulating film.
[D] 성분의 감열성 산 생성 화합물 또는 감열성 염기 생성 화합물은, 1종을 단독으로 사용해도 좋고, 2종 이상을 혼합하여 사용해도 좋다. 당해 포지티브형 감방사선성 수지 조성물에 있어서 [C] 성분을 사용하는 경우의 양은, [A] 성분 100질량부에 대하여, 바람직하게는 0.1∼10질량부, 보다 바람직하게는 0.5∼5질량부이다. [D] 성분의 사용 비율을 0.1∼10질량부로 함으로써, 양호한 내열성 및 내용제성을 갖는 층간 절연막을 형성할 수 있다. The thermosensitive acid generating compound or the thermosensitive base generating compound of the component [D] may be used alone or in combination of two or more thereof. The quantity at the time of using [C] component in the said positive radiation sensitive resin composition is 0.1-10 mass parts with respect to 100 mass parts of [A] components, Preferably it is 0.5-5 mass parts. . By setting the use ratio of component [D] to 0.1-10 mass parts, the interlayer insulation film which has favorable heat resistance and solvent resistance can be formed.
[E] 성분의 적어도 1개의 에틸렌성 불포화 2중 결합을 갖는 중합성 화합물로서, 예를 들면 단관능 (메타)아크릴레이트, 2관능 (메타)아크릴레이트, 3관능 이상의 (메타)아크릴레이트 등을 매우 적합하게 이용할 수 있다. As the polymerizable compound having at least one ethylenically unsaturated double bond of the component [E], for example, monofunctional (meth) acrylate, difunctional (meth) acrylate, trifunctional or higher (meth) acrylate, or the like It can be used very suitably.
단관능 (메타)아크릴레이트로서는, 예를 들면 2-하이드록시에틸(메타)아크릴레이트, 카르비톨(메타)아크릴레이트, 이소보르닐(메타)아크릴레이트, 3-메톡시부틸(메타)아크릴레이트, 2-(메타)아크릴로일옥시에틸-2-하이드록시프로필프탈레이트 등을 들 수 있다. 이들 단관능 (메타)아크릴레이트의 시판품으로서는, 예를 들면 아로닉스(ARONIX) M-101, 동 M-111, 동 M-114(이상, 토아고세이 가부시키가이샤 제조), KAYARAD TC-110S, 동 TC-120S(이상, 닛폰카야쿠 가부시키가이샤 제조), 비스코트(VISCOAT) 158, 동 2311(이상, 오사카유키카가쿠코교 가부시키가이샤 제조) 등을 들 수 있다. As monofunctional (meth) acrylate, 2-hydroxyethyl (meth) acrylate, carbitol (meth) acrylate, isobornyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, for example And 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate. As a commercial item of these monofunctional (meth) acrylates, for example, ARONIX M-101, copper M-111, copper M-114 (above, Toagosei Co., Ltd.), KAYARAD TC-110S, copper TC-120S (above, manufactured by Nippon Kayaku Co., Ltd.), VISCOAT 158, East 2311 (above, manufactured by Osaka Yukikagaku Kogyo Co., Ltd.), and the like.
2관능 (메타)아크릴레이트로서는, 예를 들면 에틸렌글리콜디(메타)아크릴레이트, 1,6-헥산디올디(메타)아크릴레이트, 1,9-노난디올디(메타)아크릴레이트, 폴리프로필렌글리콜디(메타)아크릴레이트, 테트라에틸렌글리콜디(메타)아크릴레이트, 비스페녹시에탄올플루오렌디(메타)아크릴레이트, 비스페녹시에탄올플루오렌디(메타)아크릴레이트 등을 들 수 있다. 이들 2관능 (메타)아크릴레이트의 시판품으로서는, 예를 들면 아로닉스 M-210, 동 M-240, 동 M-6200(이상, 토아고세이 가부시키가이샤 제조), KAYARAD HDDA, 동 HX-220, 동 R-604(이상, 닛폰카야쿠 가부시키가이샤 제조), 비스코트 260, 동 312, 동 335HP(이상, 오사카유키카가쿠코교 가부시키가이샤 제조) 등을 들 수 있다. As a bifunctional (meth) acrylate, for example, ethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, polypropylene glycol Di (meth) acrylate, tetraethylene glycol di (meth) acrylate, bisphenoxyethanol fluorene di (meth) acrylate, bisphenoxy ethanol fluorene di (meth) acrylate, and the like. As a commercial item of these bifunctional (meth) acrylates, for example, Aronix M-210, copper M-240, copper M-6200 (above, Toagosei Co., Ltd.), KAYARAD HDDA, copper HX-220, copper R-604 (above, manufactured by Nippon Kayaku Co., Ltd.), biscot 260, copper 312, copper 335HP (above, manufactured by Osaka Yukikagaku Kogyo Co., Ltd.), and the like.
3관능 이상의 (메타)아크릴레이트로서는, 예를 들면 트리메틸올프로판트리(메타)아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트, 트리((메타)아크릴로일옥시에틸)포스페이트, 펜타에리트리톨테트라(메타)아크릴레이트, 디펜타에리트리톨펜타(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트 등을 들 수 있다. 이들 3관능 이상의 (메타)아크릴레이트의 시판품으로서는, 예를 들면 아로닉스 M-309, 동 M-400, 동 M-405, 동 M-450, 동 M-7100, 동 M-8030, 동 M-8060(이상, 토아고세이 가부시키가이샤 제조), KAYARAD TMPTA, 동 DPHA, 동 DPCA-20, 동 DPCA-30, 동 DPCA-60, 동 DPCA-120(이상, 닛폰카야쿠 가부시키가이샤 제조), 비스코트 295, 동 300, 동 360, 동 GPT, 동 3PA, 동 400(이상, 오사카유키카가쿠코교 가부시키가이샤 제조) 등을 들 수 있다. As (meth) acrylate more than trifunctional, for example, trimethylol propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri ((meth) acryloyloxyethyl) phosphate, pentaerythritol tetra (Meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc. are mentioned. As a commercial item of these trifunctional or more (meth) acrylates, for example, Aronix M-309, Copper M-400, Copper M-405, Copper M-450, Copper M-7100, Copper M-8030, Copper M- 8060 (above, Toagosei Co., Ltd.), KAYARAD TMPTA, East DPHA, East DPCA-20, East DPCA-30, East DPCA-60, East DPCA-120 (above, Nippon Kayaku Co., Ltd.), Vis Coat 295, copper 300, copper 360, copper GPT, copper 3PA, copper 400 (above, manufactured by Osaka Yuki Chemical Co., Ltd.).
이들 메타(아크릴레이트)류 중, 3관능 이상의 (메타)아크릴레이트가 바람직하게 이용된다. 그 중에서도, 트리메틸올프로판트리(메타)아크릴레이트, 펜타에리트리톨테트라(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트가 특히 바람직하다. Of these meta (acrylates), trifunctional or higher (meth) acrylates are preferably used. Especially, trimethylol propane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, and dipentaerythritol hexa (meth) acrylate are especially preferable.
이들 단관능, 2관능 또는 3관능 이상의 (메타)아크릴레이트는, 단독으로 혹은 조합하여 이용된다. 당해 포지티브형 감방사선성 수지 조성물에 있어서 [E] 성분을 사용하는 경우의 양은, [A] 성분 100질량부에 대하여, 바람직하게는 1∼50질량부이고, 더욱 바람직하게는 3∼30질량부이다. [E] 성분의 사용 비율을 1∼50질량부로 함으로써, 얻어지는 층간 절연막의 내열성 및 내용제성을 보다 향상시킬 수 있다. These monofunctional, bifunctional or trifunctional or more (meth) acrylates are used individually or in combination. The quantity at the time of using [E] component in the said positive radiation sensitive resin composition becomes like this. Preferably it is 1-50 mass parts with respect to 100 mass parts of [A] components, More preferably, it is 3-30 mass parts. to be. By setting the use ratio of the component (E) to 1 to 50 parts by mass, the heat resistance and the solvent resistance of the resulting interlayer insulating film can be further improved.
당해 포지티브형 감방사선성 수지 조성물에는, 도막 형성시의 도포성을 더욱 향상시키기 위해, [F] 성분으로서 계면 활성제를 사용할 수 있다. 매우 적합하게 이용할 수 있는 계면 활성제로서는, 불소계 계면 활성제, 실리콘계 계면 활성제 및 비이온계 계면 활성제를 들 수 있다. In order to further improve the applicability | paintability at the time of coating film formation, surfactant can be used for the said positive radiation sensitive resin composition as a [F] component. Examples of the surfactant that can be suitably used include fluorine-based surfactants, silicone-based surfactants, and nonionic surfactants.
불소계 계면 활성제의 예로서는, 1,1,2,2-테트라플루오로옥틸(1,1,2,2-테트라플루오로프로필)에테르, 1,1,2,2-테트라플루오로옥틸헥실에테르, 옥타에틸렌글리콜디(1,1,2,2-테트라플루오로부틸)에테르, 헥사에틸렌글리콜(1,1,2,2,3,3-헥사플루오로펜틸)에테르, 옥타프로필렌글리콜디(1,1,2,2-테트라플루오로부틸)에테르, 헥사프로필렌글리콜디(1,1,2,2,3,3-헥사플루오로펜틸)에테르 등의 플루오로에테르류; 퍼플루오로도데실술폰산 나트륨; 1,1,2,2,8,8,9,9,10,10-데카플루오로도데칸, 1,1,2,2,3,3-헥사플루오로데칸 등의 플루오로알칸류; 플루오로알킬벤젠술폰산 나트륨류; 플루오로알킬옥시에틸렌에테르류; 플루오로알킬암모늄요오다이드류; 플루오로알킬폴리옥시에틸렌에테르류; 퍼플루오로알킬폴리옥시에탄올류; 퍼플루오로알킬알콕시레이트류; 불소계 알킬에스테르류 등을 들 수 있다. Examples of the fluorine-based surfactants include 1,1,2,2-tetrafluorooctyl (1,1,2,2-tetrafluoropropyl) ether, 1,1,2,2-tetrafluorooctylhexyl ether and octa Ethylene glycol di (1,1,2,2-tetrafluorobutyl) ether, hexaethylene glycol (1,1,2,2,3,3-hexafluoropentyl) ether, octapropylene glycol di (1,1 Fluoroethers such as 2,2-tetrafluorobutyl) ether and hexapropylene glycol di (1,1,2,2,3,3-hexafluoropentyl) ether; Sodium perfluorododecylsulfonate; Fluoroalkanes such as 1,1,2,2,8,8,9,9,10,10-decafluorododecane and 1,1,2,2,3,3-hexafluorodecane; Sodium fluoroalkylbenzenesulfonic acid; Fluoroalkyloxyethylene ethers; Fluoroalkylammonium iodides; Fluoroalkyl polyoxyethylene ethers; Perfluoroalkyl polyoxyethanols; Perfluoroalkylalkoxylates; Fluorine-based alkyl esters and the like.
이들 불소계 계면 활성제의 시판품으로서는, BM-1000, BM-1100(이상, BM Chemie사 제조), 메가팩(MEGAFACE) F142D, 동 F172, 동 F173, 동 F183, 동 F178, 동 F191, 동 F471(이상, 다이닛폰잉키카가쿠코교 가부시키가이샤 제조), 플루오라드(FLUORAD) FC-170C, FC-171, FC-430, FC-431(이상, 스미토모쓰리엠 가부시키가이샤 제조), 서프론(SURFLON) S-112, 동 S-113, 동 S-131, 동 S-141, 동 S-145, 동 S-382, 동 SC-101, 동 SC-102, 동 SC-103, 동 SC-104, 동 SC-105, 동 SC-106(아사히가라스 가부시키가이샤 제조), 에프톱 EF301, 동 303, 동 352(신아키타카세이 가부시키가이샤 제조) 등을 들 수 있다. Commercially available products of these fluorine-based surfactants include BM-1000, BM-1100 (above, manufactured by BM Chemie Co., Ltd.), Mega Pack F142D, Copper F172, Copper F173, Copper F183, Copper F178, Copper F191, Copper F471 (or higher). Dai Nippon Inkika Chemical Industries, Ltd., Fluorad FC-170C, FC-171, FC-430, FC-431 (above, Sumitomo 3M Co., Ltd.), SURFLON S -112, S-113, S-131, S-141, S-145, S-382, SC-101, SC-102, SC-103, SC-104, SC -105, East SC-106 (made by Asahi Glass Co., Ltd.), F-top EF301, East 303, East 352 (made by Shin-Akita Kasei Co., Ltd.), etc. are mentioned.
실리콘계 계면 활성제의 구체예로서는, 시판되고 있는 상품명으로, DC3PA, DC7PA, FS-1265, SF-8428, SH11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH-190, SH-193, SZ-6032(이상, 토레·다우코닝·실리콘 가부시키가이샤 제조), TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452(이상, GE 토시바실리콘 가부시키가이샤 제조) 등을 들 수 있다. As a specific example of a silicone type surfactant, it is a brand name marketed, and it is DC3PA, DC7PA, FS-1265, SF-8428, SH11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH-190, SH-193, SZ-6032 (above, Torre Dow Corning Silicone Co., Ltd., TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452 (above, GE Toshiba Silicone Co., Ltd.), etc. are mentioned. .
비이온계 계면 활성제로서는, 예를 들면 폴리옥시에틸렌라우릴에테르, 폴리옥시에틸렌스테아릴에테르, 폴리옥시에틸렌올레일에테르 등의 폴리옥시에틸렌알킬에테르류; 폴리옥시에틸렌옥틸페닐에테르, 폴리옥시에틸렌노닐페닐에테르 등의 폴리옥시에틸렌아릴에테르류; 폴리옥시에틸렌디라우레이트, 폴리옥시에틸렌디스테아레이트 등의 폴리옥시에틸렌디알킬에스테르류; (메타)아크릴산계 공중합체류 등을 들 수 있다. 비이온계 계면 활성제의 대표적인 시판품으로서는, 폴리플로우(POLYFLOW) No. 57, 95(쿄에이샤카가쿠 가부시키가이샤 제조)를 들 수 있다. As a nonionic surfactant, For example, polyoxyethylene alkyl ether, such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether; Polyoxyethylene aryl ethers such as polyoxyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether; Polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; (Meth) acrylic acid type copolymers etc. are mentioned. As a typical commercial item of a nonionic surfactant, POLYFLOW No. 57, 95 (made by Kyo-Eisha Chemical Co., Ltd.) is mentioned.
[F] 성분의 계면 활성제는, 단독으로 혹은 2종 이상을 조합하여 사용할 수 있다. 당해 포지티브형 감방사선성 수지 조성물에 있어서 [F] 성분을 사용하는 경우의 양은, [A] 성분 100질량부에 대하여, 바람직하게는 0.01∼3질량부, 더욱 바람직하게는 0.05∼2질량부이다. [F] 성분의 사용 비율을 0.01∼3질량부로 함으로써, 기판 상에 도막을 형성할 때의 도포 불균일의 발생을 억제할 수 있다. The surfactant of the [F] component can be used individually or in combination of 2 or more types. The quantity at the time of using [F] component in the said positive radiation sensitive resin composition becomes like this. Preferably it is 0.01-3 mass parts, More preferably, it is 0.05-2 mass parts with respect to 100 mass parts of [A] components. . By setting the use ratio of the component [F] to 0.01 to 3 parts by mass, the occurrence of coating irregularity in forming a coating film on the substrate can be suppressed.
당해 포지티브형 감방사선성 수지 조성물에 있어서는, 얻어지는 층간 절연막과 기판과의 밀착성을 향상시키기 위해 [G] 성분인 밀착 조제를 사용할 수 있다. 이러한 밀착 조제로서는, 관능성 실란 커플링제가 바람직하게 사용된다. 관능성 실란 커플링제의 예로서는, 카복실기, 메타크릴로일기, 이소시아네이트기, 에폭시 기 등의 반응성 치환기를 갖는 실란 커플링제 등을 들 수 있다. 관능성 실란 커플링제의 구체예로서는, 트리메톡시실릴벤조산, γ-메타크릴옥시프로필트리메톡시실란, 비닐트리아세톡시실란, 비닐트리메톡시실란, γ-이소시아네이트프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, β-(3,4-에폭시사이클로헥실)에틸트리메톡시실란 등을 들 수 있다. In the said positive radiation sensitive resin composition, the adhesion | attachment adjuvant which is a [G] component can be used in order to improve the adhesiveness of the interlayer insulation film obtained and a board | substrate. As this adhesion | attachment adjuvant, a functional silane coupling agent is used preferably. As an example of a functional silane coupling agent, the silane coupling agent etc. which have reactive substituents, such as a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, etc. are mentioned. Specific examples of the functional silane coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, and γ-glycol. Cidoxy propyl trimethoxysilane, (beta)-(3, 4- epoxycyclohexyl) ethyl trimethoxysilane, etc. are mentioned.
[G] 성분의 밀착 조제는, 단독으로 혹은 2종 이상을 조합하여 사용할 수 있다. 당해 포지티브형 감방사선성 수지 조성물에 있어서 [G] 성분을 사용하는 경우의 양은, [A] 성분 100질량부에 대하여, 바람직하게는 0.01∼20질량부, 더욱 바람직하게는 0.05∼15질량부이다. [G] 성분의 밀착 조제의 배합량을 0.01∼20질량부로 함으로써, 얻어지는 층간 절연막과 기체와의 밀착성이 가장 양호해진다. The adhesion aid of the [G] component can be used individually or in combination of 2 or more types. The quantity at the time of using [G] component in the said positive radiation sensitive resin composition becomes like this. Preferably it is 0.01-20 mass parts, More preferably, it is 0.05-15 mass parts with respect to 100 mass parts of [A] components. . By making the compounding quantity of the adhesion | attachment adjuvant of [G] component into 0.01-20 mass parts, the adhesiveness of the interlayer insulation film obtained and a base | substrate becomes the best.
당해 포지티브형 감방사선성 수지 조성물에는, 추가로 [H] 라디칼 포착제를 가할 수 있다. [H] 라디칼 포착제로서는, 힌더드페놀 화합물, 힌더드아민 화합물, 알킬포스페이트 화합물 및 황 원자를 포함하는 화합물로 이루어지는 군으로부터 선택되는 적어도 1종을 이용할 수 있다. [H] radical scavenger can be added to the said positive radiation sensitive resin composition further. [H] As the radical scavenger, at least one selected from the group consisting of a hindered phenol compound, a hindered amine compound, an alkyl phosphate compound and a sulfur atom can be used.
상기 힌더드페놀 화합물로서는, 예를 들면 펜타에리트리톨테트라키스[3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트], 티오디에틸렌비스[3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트], 옥타데실-3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트, 1,3,5-트리메틸-2,4,6-트리스(3,5-디-tert-부틸-4-하이드록시벤질)벤젠, N,N'-헥산-1,6-디일비스[3-(3,5-디-tert-부틸-4-하이드록시페닐프로피온아미드)], 3,3',3",5',5"-헥사-tert-부틸-α,α',α"-(메시틸렌-2,4,6-트리일)트리-p-크레졸, 4,6-비스(옥틸티오메틸)-o-크레졸, 4,6-비스(도데실티오메틸)-o-크레졸, 에틸렌비스(옥시에틸렌)비스[3-(5-tert-부틸-4-하이드록시-m-톨릴)프로피오네이트], 헥사메틸렌비스[3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트], 1,3,5-트리스(3,5-디-tert-부틸-4-하이드록시벤질)-1,3,5-트리아진-2,4,6(1H,3H,5H)-트리온, 1,3,5-트리스[(4-tert-부틸-3-하이드록시-2,6-자일린)메틸]-1,3,5-트리아진-2,4,6(1H,3H,5H)-트리온, 2,6-디-tert-부틸-4-(4,6-비스(옥틸티오)-1,3,5-트리아진-2-일아민)페놀, 1,3,5-트리스(3',5'-디-tert-부틸-4'-하이드록시벤질)이소시아누르산 등을 들 수 있다. Examples of the hindered phenol compound include pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], thiodiethylenebis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 1,3,5 -Trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, N, N'-hexane-1,6-diylbis [3- (3,5- Di-tert-butyl-4-hydroxyphenylpropionamide)], 3,3 ', 3 ", 5', 5" -hexa-tert-butyl-α, α ', α "-(mesitylene-2, 4,6-triyl) tri-p-cresol, 4,6-bis (octylthiomethyl) -o-cresol, 4,6-bis (dodecylthiomethyl) -o-cresol, ethylenebis (oxyethylene) Bis [3- (5-tert-butyl-4-hydroxy-m-tolyl) propionate], hexamethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propio Nate], 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4, 6 (1H, 3H, 5H) -trione, 1,3,5-tris [(4-tert-butyl-3-hydroxy-2,6-xylyl) methyl] -1,3,5-triazine -2,4,6 (1H, 3H, 5H) -trione, 2,6-di-tert-butyl-4- (4,6-bis (octylthio) -1,3,5-triazine-2 -Ylamine) phenol, 1,3,5-tris (3 ', 5'-di-tert-butyl-4'-hydroxybenzyl) isocyanuric acid, etc. are mentioned.
이들 시판품으로서, 예를 들면 As these commercial items, for example
아데카스타브(ADK STAB) AO-20, 아데카스타브 AO-30, 아데카스타브 AO-40, 아데카스타브 AO-50, 아데카스타브 AO-60, 아데카스타브 AO-70, 아데카스타브 AO-80, 아데카스타브 AO-330(이상, 가부시키가이샤 ADEKA 제조); ADADE STAB AO-20, ADADESTAB AO-30, ADADESTAB AO-40, ADADESTAB AO-50, ADADESTAB AO-60, ADADESTAB AO-70, ADADESTAB AO -80, Adecastab AO-330 (above, manufactured by ADEKA);
sumilizerGM, sumilizerGS, sumilizerMDP-S, sumilizerBBM-S, sumilizerWX-R, sumilizerGA-80(이상, 스미토모카가쿠 가부시키가이샤 제조); sumilizerGM, sumilizerGS, sumilizerMDP-S, sumilizerBBM-S, sumilizerWX-R, sumilizerGA-80 (above, manufactured by Sumitomo Kagaku Co., Ltd.);
IRGANOX L101, IRGANOX L115, IRGANOX 1010, IRGANOX 1035, IRGANOX 1076, IRGANOX 1098, IRGANOX 1135, IRGANOX 1330, IRGANOX 1726, IRGANOX 1425WL, IRGANOX 1520L, IRGANOX 245, IRGANOX 259, IRGANOX 3114, IRGANOX 565, IRGAMOD295(이상, 치바·스페셜티·케미칼스 가부시키가이샤 제조); IRGANOX L101, IRGANOX L115, IRGANOX 1010, IRGANOX 1035, IRGANOX 1076, IRGANOX 1098, IRGANOX 1135, IRGANOX 1330, IRGANOX 1726, IRGANOX 1425WL, IRGANOX 1520L, IRGANOX 245, IRGANOX 2114, IRGANOX 2114565 Specialty Chemicals Co., Ltd.);
요시녹스 BHT, 요시녹스 BB, 요시녹스 2246G, 요시녹스 425, 요시녹스 250, 요시녹스 930, 요시녹스 SS, 요시녹스 TT, 요시녹스 917, 요시녹스 314(이상, 가부시키가이샤 에이피아이 코포레이션 제조) 등을 들 수 있다. Yoshinox BHT, Yoshinox BB, Yoshinox 2246G, Yoshinox 425, Yoshinox 250, Yoshinox 930, Yoshinox SS, Yoshinox TT, Yoshinox 917, Yoshinox 314 (above, manufactured by APC Co., Ltd.) Etc. can be mentioned.
상기 힌더드아민 화합물로서는, 예를 들면 As the hindered amine compound, for example
테트라키스(2,2,6,6-펜타메틸-4-피페리딜)-1,2,3,4-부탄테트라카복시레이트, 비스(1-옥틸옥시-2,2,6,6-테트라메틸-4-피페리딜)세바케이트, 비스(1,2,2,6,6-펜타메틸-4-피페리딜)[[3,5-비스(1,1-디메틸에틸)-4-하이드록시페닐]메틸]부틸말로네이트 등을 들 수 있고, 이들 시판품으로서, 예를 들면 아데카스타브 LA-52, 아데카스타브 LA57, 아데카스타브 LA-62, 아데카스타브 LA-67, 아데카스타브 LA-63P, 아데카스타브 LA-68LD, 아데카스타브 LA-77, 아데카스타브 LA-82, 아데카스타브 LA-87(이상, 가부시키가이샤 ADEKA 제조); Tetrakis (2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, bis (1-octyloxy-2,2,6,6-tetra Methyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis (1,1-dimethylethyl) -4- Hydroxyphenyl] methyl] butyl malonate, and the like. Examples of such commercially available products include adecastab LA-52, adecastab LA57, adecastab LA-62, adecastab LA-67, and adecas. Tab LA-63P, Adecastab LA-68LD, Adecastab LA-77, Adecastab LA-82, Adecastab LA-87 (above, manufactured by ADEKA);
sumilizer9A(스미토모카가쿠 가부시키가이샤 제조); sumilizer 9A (manufactured by Sumitomo Chemical Co., Ltd.);
CHIMASSORB 119FL, CHIMASSORB 2020FDL, CHIMASSORB 944FDL, TINUVIN 622LD, TINUVIN 123, TINUVIN 144, TINUVIN 765, TINUVIN 770DF(이상, 치바·스페셜티·케미칼스 가부시키가이샤 제조) 등을 들 수 있다. CHIMASSORB 119FL, CHIMASSORB 2020FDL, CHIMASSORB 944FDL, TINUVIN 622LD, TINUVIN 123, TINUVIN 144, TINUVIN 765, and TINUVIN 770DF (above, manufactured by Chiba Specialty Chemicals Co., Ltd.).
상기 알킬포스페이트 화합물로서는, 예를 들면 As said alkyl phosphate compound, for example
부틸리덴비스{2-tert-부틸-5-메틸-p-페닐렌}-P, P, P, P-테트라트리데실비스 (포스핀), 디스테아릴펜타에리트리톨디포스파이트, 2,2'-메틸렌비스(4,6-디-tert-부틸-1-페닐옥시)(2-에틸헥실옥시)포스포러스, 트리스(2,4-디-tert-부틸페닐)포스파이트, 3,9-비스(2,6-디-tert-부틸-4-메틸페녹시)-2,4,8,10-테트라옥사-3,9-디포스파스피로[5.5]운데칸 등을 들 수 있다. Butylidenebis {2-tert-butyl-5-methyl-p-phenylene} -P, P, P, P-tetratridecylbis (phosphine), distearylpentaerythritol diphosphite, 2, 2'-methylenebis (4,6-di-tert-butyl-1-phenyloxy) (2-ethylhexyloxy) phosphorus, tris (2,4-di-tert-butylphenyl) phosphite, 3, 9-bis (2,6-di-tert-butyl-4-methylphenoxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane and the like.
이들 시판품으로서, 예를 들면 As these commercial items, for example
아데카스타브 PEP-4C, 아데카스타브 PEP-8, 아데카스타브 PEP-8W, 아데카스타브 PEP-24G, 아데카스타브 PEP-36, 아데카스타브 HP-10, 아데카스타브 2112, 아데카스타브 260, 아데카스타브 522A, 아데카스타브 1178, 아데카스타브 1500, 아데카스타브 C, 아데카스타브 135A, 아데카스타브 3010, 아데카스타브 TPP(이상, 가부시키가이샤 ADEKA 제조); Adecastab PEP-4C, Adecastab PEP-8, Adecastab PEP-8W, Adecastab PEP-24G, Adecastab PEP-36, Adecastab HP-10, Adecastab 2112, Adecastab 260, Adecastab 522A, Adecastab 1178, Adecastab 1500, Adecastab C, Adecastab 135A, Adecastab 3010, Adecastab TPP (above, manufactured by ADEKA);
IRGAFOS 168(치바·스페셜티·케미칼스 가부시키가이샤 제조) 등을 들 수 있다. IRGAFOS 168 (made by Chiba Specialty Chemicals Co., Ltd.), etc. are mentioned.
상기 황 원자를 포함하는 화합물로서는, 예를 들면 As a compound containing the said sulfur atom, for example
펜타에리트리톨테트라키스(3-라우릴티오프로피오네이트), 디(프로피온산-n-트리데카닐)술피드, 티오디에틸렌비스[3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트] 등을 들 수 있는 것 외에, 티오에테르의 시판품으로서, 예를 들면 아데카스타브 AO-412S, 아데카스타브 AO-503(이상, 가부시키가이샤 ADEKA 제조); Pentaerythritol tetrakis (3-laurylthiopropionate), di (propionic acid-n-tridecanyl) sulfide, thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydride Oxyphenyl) propionate] and the like, and commercially available products of thioethers include, for example, adecastabu AO-412S and adecastabu AO-503 (above, manufactured by ADEKA);
sumilizerTPL-R, sumilizerTPM, sumilizerTPS, sumilizerTP-D, sumilizerMB(이상, 스미토모카가쿠 가부시키가이샤 제조); sumilizerTPL-R, sumilizerTPM, sumilizerTPS, sumilizerTP-D, sumilizerMB (above, Sumitomo Kagaku Co., Ltd.);
IRGANOX PS800FD, IRGANOX PS802FD, IRGANOX 1035(이상, 치바·스페셜티·케미칼스 가부시키가이샤 제조); IRGANOX PS800FD, IRGANOX PS802FD, and IRGANOX 1035 (above, Chiba Specialty Chemicals Co., Ltd. product);
DLTP, DSTP, DMTP, DTTP(이상, 가부시키가이샤 에이피아이 코포레이션 제조) 등을 들 수 있다. DLTP, DSTP, DMTP, DTTP (above, Apia Corporation make), etc. are mentioned.
[H] 성분의 라디칼 포착제는, 단독으로 혹은 2종 이상을 조합하여 사용할 수 있다. 당해 포지티브형 감방사선성 수지 조성물에 있어서 [H] 성분을 사용하는 경우의 양은, [A] 성분 100질량부에 대하여, 바람직하게는 0.1∼30질량부이고, 보다 바람직하게는 1∼30질량부이다. 이 사용량이 0.1∼30질량부일 때, 형성되는 층간 절연막의 패턴 치수의 불안정화 및 투명성의 저하 그리고 층간 절연막 형성시의 해상도의 저하를 억제하고, 그리고 감방사선성 수지 조성물의 보존 안정성의 저하를 방지할 수 있다. The radical trapping agent of the [H] component can be used individually or in combination of 2 or more types. The quantity at the time of using [H] component in the said positive radiation sensitive resin composition becomes like this. Preferably it is 0.1-30 mass parts with respect to 100 mass parts of [A] components, More preferably, it is 1-30 mass parts to be. When the amount is 0.1 to 30 parts by mass, the destabilization of the pattern dimension of the interlayer insulating film to be formed and the decrease in transparency and the reduction in the resolution at the time of forming the interlayer insulating film can be suppressed, and the deterioration in the storage stability of the radiation-sensitive resin composition can be prevented. Can be.
포지티브형 감방사선성 수지 조성물Positive radiation sensitive resin composition
본 발명의 포지티브형 감방사선성 수지 조성물은, 상기의 [A] 및 [B] 및 [C] 성분, 그리고 임의 성분([D]∼[H] 성분)을 균일하게 혼합함으로써 조제된다. 통상, 포지티브형 감방사선성 수지 조성물은, 바람직하게는 적당한 용매에 용해되어 용액 상태로 보존되어, 사용된다. 예를 들면, 용매 중에서, [A] 및 [B] 성분 및 [C] 그리고 임의 성분을 소정의 비율로 혼합함으로써, 용액 상태의 포지티브형 감방사선성 수지 조성물을 조제할 수 있다.The positive radiation-sensitive resin composition of the present invention is prepared by uniformly mixing the above-mentioned [A] and [B] and [C] components, and arbitrary components ([D]-[H] components). Usually, the positive radiation-sensitive resin composition is preferably dissolved in a suitable solvent and stored in a solution state and used. For example, the positive radiation sensitive resin composition of a solution state can be prepared by mixing [A], [B] component, [C], and arbitrary components in a predetermined ratio in a solvent.
이러한 용매 중, 각 성분의 용해성, 각 성분과의 비(非)반응성, 도막 형성의 용이성 등의 점에서, 알코올류, 글리콜에테르, 에틸렌글리콜모노알킬에테르아세테이트, 에스테르류, 디에틸렌글리콜모노알킬에테르아세테이트, 디에틸렌글리콜디알킬에테르, 디프로필렌글리콜디알킬에테르, 프로필렌글리콜모노알킬에테르, 프로필렌글리콜모노알킬에테르아세테이트가 바람직하게 이용된다. 이들 용매 중, 벤질알코올, 2-페닐에틸알코올, 3-페닐-1-프로판올, 에틸렌글리콜모노부틸에테르아세테이트, 디에틸렌글리콜모노에틸에테르아세테이트, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜에틸메틸에테르, 디에틸렌글리콜디메틸에테르, 디프로필렌글리콜디메틸에테르, 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노메틸에테르아세테이트, 2-또는 3-메톡시프로피온산 메틸, 2-또는 3-에톡시프로피온산 에틸을 특히 바람직하게 사용할 수 있다. Among these solvents, alcohols, glycol ethers, ethylene glycol monoalkyl ether acetates, esters, diethylene glycol monoalkyl ethers in terms of solubility of each component, non-reactivity with each component, ease of coating film formation, and the like. Acetate, diethylene glycol dialkyl ether, dipropylene glycol dialkyl ether, propylene glycol monoalkyl ether, and propylene glycol monoalkyl ether acetate are preferably used. Among these solvents, benzyl alcohol, 2-phenylethyl alcohol, 3-phenyl-1-propanol, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, Diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl 2- or 3-methoxypropionate, ethyl 2- or 3-ethoxypropionate can be particularly preferably used. have.
또한, 형성되는 도막의 면내 균일성을 높이기 위해, 상기 용매와 함께 고(高)비점 용매를 병용할 수도 있다. 병용할 수 있는 고비점 용매로서는, 예를 들면 N-메틸포름아미드, N,N-디메틸포름아미드, N-메틸포름아닐리드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭사이드, 벤질에틸에테르, 디헥실에테르, 아세토닐아세톤, 이소포론, 카프로산(caproic acid), 카프릴산(caprylic acid), 1-옥탄올, 1-노난올, 아세트산 벤질, 벤조산 에틸, 옥살산 디에틸, 말레산 디에틸, γ-부티로락톤, 탄산 에틸렌, 탄산 프로필렌, 페닐셀로솔브아세테이트 등을 들 수 있다. 이들 고비점 용매 중, N-메틸피롤리돈, γ-부티로락톤, N,N-디메틸아세트아미드가 바람직하다. Moreover, in order to improve the in-plane uniformity of the coating film formed, you may use a high boiling point solvent together with the said solvent. As a high boiling point solvent which can be used together, it is N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide, N-methylpi, for example. Ralidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetonyl acetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl acetate, Ethyl benzoate, diethyl oxalate, diethyl maleate, gamma -butyrolactone, ethylene carbonate, propylene carbonate, phenylcellosolve acetate, and the like. Among these high boiling point solvents, N-methylpyrrolidone, γ-butyrolactone, and N, N-dimethylacetamide are preferable.
당해 포지티브형 감방사선성 수지 조성물의 용매로서, 고비점 용매를 병용하는 경우, 그 사용량은, 용매 전체량에 대하여 50질량% 이하, 바람직하게는 40질량% 이하, 더욱 바람직하게는 30질량% 이하로 할 수 있다. 고비점 용매의 사용 비율을 50질량% 이하로 함으로써, 도막의 막두께 균일성을 높임과 동시에, 방사선 감도 저하를 억제할 수 있다. When using a high boiling point solvent together as a solvent of the said positive radiation sensitive resin composition, the usage-amount is 50 mass% or less with respect to a solvent whole quantity, Preferably it is 40 mass% or less, More preferably, it is 30 mass% or less You can do By making the use ratio of a high boiling point solvent into 50 mass% or less, while improving the film thickness uniformity of a coating film, the fall of a radiation sensitivity can be suppressed.
당해 포지티브형 감방사선성 수지 조성물을 용액 상태로 하여 조제하는 경우, 용액 중에 차지하는 용매 이외의 성분(즉, 상기의 [A] 및 [B] 및 [C] 성분, 그리고 그 외의 임의 성분의 합계량)의 비율은, 사용 목적이나 소망하는 막두께 등에 따라서 임의로 설정할 수 있지만, 바람직하게는 5∼50질량%, 보다 바람직하게는 10∼40질량%, 더욱 바람직하게는 15∼35질량%이다. 이와 같이 하여 조제된 포지티브형 감방사선성 수지 조성물의 용액은, 공경 0.2㎛ 정도의 밀리포어필터 등을 이용하여 여과한 후, 사용에 제공할 수도 있다. When preparing the positive radiation-sensitive resin composition in a solution state, components other than the solvent in the solution (that is, the total amount of the above-mentioned [A] and [B] and [C] components and other optional components) Although the ratio of can be arbitrarily set according to a use purpose, desired film thickness, etc., Preferably it is 5-50 mass%, More preferably, it is 10-40 mass%, More preferably, it is 15-35 mass%. The solution of the positive radiation-sensitive resin composition thus prepared can be used for use after being filtered using a Millipore filter having a pore size of about 0.2 μm or the like.
층간 절연막의 형성Formation of Interlayer Insulator
다음으로, 당해 포지티브형 감방사선성 수지 조성물을 이용하여, 본 발명의 층간 절연막을 형성하는 방법에 대해서 서술한다. 당해 방법은, 이하의 공정을 이하의 기재 순으로 포함한다. Next, the method of forming the interlayer insulation film of this invention is described using this positive radiation sensitive resin composition. The method includes the following steps in the order described below.
(1) 본 발명의 포지티브형 감방사선성 수지 조성물의 도막을 기판 상에 형성하는 공정, (1) Process of forming the coating film of positive type radiation sensitive resin composition of this invention on board | substrate,
(2) 공정 (1)에서 형성한 도막의 적어도 일부에 방사선을 조사하는 공정, (2) irradiating at least a part of the coating film formed in step (1) with radiation;
(3) 공정 (2)에서 방사선이 조사된 도막을 현상하는 공정 및,(3) developing the coating film irradiated with radiation in step (2), and
(4) 공정 (3)에서 현상된 도막을 가열하는 공정. (4) A step of heating the coating film developed in the step (3).
(1) 포지티브형 (1) positive type 감방사선성Radiation 수지 조성물의 도막을 The coating film of the resin composition 기판 상에On a substrate 형성하는 공정 Forming process
상기 (1)의 공정에 있어서, 본 발명의 포지티브형 감방사선성 수지 조성물의 용액을 기판 표면에 도포하고, 바람직하게는 프리베이킹을 행함으로써 용매를 제거하여, 포지티브형 감방사선성 수지 조성물의 도막을 형성한다. 사용할 수 있는 기판의 종류로서는, 예를 들면, 유리 기판, 실리콘 웨이퍼 및 이들의 표면에 각종 금속이 형성된 기판을 들 수 있다. In the process of said (1), the solvent of a positive radiation sensitive resin composition is removed by apply | coating the solution of the positive radiation sensitive resin composition of this invention to the surface of a board | substrate, Preferably prebaking is carried out. To form. As a kind of substrate which can be used, a glass substrate, a silicon wafer, and the board | substrate with which the various metal was formed in these surfaces are mentioned, for example.
조성물 용액의 도포 방법으로서는, 특별히 한정되지 않으며, 예를 들면 스프레이법, 롤 코팅법, 회전 도포법(스핀 코팅법), 슬릿다이 도포법, 바 도포법, 잉크젯법 등의 적절한 방법을 채용할 수 있다. 이들 도포 방법 중에서도 특히, 스핀 코팅법, 슬릿다이 도포법이 바람직하다. 프리베이킹의 조건으로서는, 각 성분의 종류, 사용 비율 등에 따라서도 상이하지만, 예를 들면, 60∼110℃에서 30초간∼15분간 정도로 할 수 있다. 형성되는 도막의 막두께로서는, 프리베이킹 후의 값으로서 예를 들면 2∼5㎛가 바람직하다. It does not specifically limit as a coating method of a composition solution, For example, appropriate methods, such as a spray method, a roll coating method, the spin coating method (spin coating method), the slit die coating method, the bar coating method, the inkjet method, can be employ | adopted. have. Among these coating methods, the spin coating method and the slit die coating method are particularly preferable. As conditions for prebaking, although it changes also with the kind, usage ratio, etc. of each component, it can be made into about 30 to 15 minutes at 60-110 degreeC, for example. As a film thickness of the coating film formed, 2-5 micrometers is preferable as a value after prebaking, for example.
(2) 도막의 적어도 일부에 방사선을 조사하는 공정(2) irradiating at least a part of the coating film with radiation
상기 (2)의 공정에서는, 형성된 도막에 소정의 패턴을 갖는 마스크를 통하여, 방사선을 조사한다. 이때 이용되는 방사선으로서는, 예를 들면 자외선, 원자외선, X선, 하전 입자선 등을 들 수 있다. In the process of (2), radiation is irradiated to the formed coating film through the mask which has a predetermined pattern. Examples of the radiation used at this time include ultraviolet rays, far ultraviolet rays, X-rays, charged particle beams, and the like.
상기 자외선으로서는, 예를 들면 g선(파장 436nm), i선(파장 365nm) 등을 들 수 있다. 원자외선으로서는, 예를 들면 KrF 엑시머 레이저 등을 들 수 있다. X선으로서는, 예를 들면 싱크로트론 방사선 등을 들 수 있다. 하전 입자선으로서는, 예를 들면 전자선 등을 들 수 있다. 이들 방사선 중, 자외선이 바람직하고, 자외선 중에서도 g선 및/또는 i선을 포함하는 방사선이 특히 바람직하다. 노광량으로서는, 50∼1,500J/m2로 하는 것이 바람직하다. As said ultraviolet-ray, g line | wire (wavelength 436 nm), i line | wire (wavelength 365 nm), etc. are mentioned, for example. As far ultraviolet rays, KrF excimer laser etc. are mentioned, for example. As X-ray, a synchrotron radiation etc. are mentioned, for example. As a charged particle beam, an electron beam etc. are mentioned, for example. Among these radiations, ultraviolet rays are preferable, and radiation including g rays and / or i rays is particularly preferred among the ultraviolet rays. As an exposure amount, it is preferable to set it as 50-1,500 J / m <2> .
(3) 현상 공정(3) developing process
(3) 현상 공정에 있어서, 상기 (2)의 공정에서 방사선이 조사된 도막에 대하여 현상을 행하고, 방사선의 조사 부분을 제거하여, 소망하는 패턴을 형성할 수 있다. 현상 처리에 이용되는 현상액으로서는, 예를 들면, 수산화 나트륨, 수산화 칼륨, 탄산 나트륨, 규산 나트륨, 메타규산 나트륨, 암모니아, 에틸아민, n-프로필아민, 디에틸아민, 디에틸아미노에탄올, 디-n-프로필아민, 트리에틸아민, 메틸디에틸아민, 디메틸에탄올아민, 트리에탄올아민, 테트라메틸암모늄하이드록사이드, 테트라에틸암모늄하이드록사이드 등의 알칼리(염기성 화합물)의 수용액을 이용할 수 있다. 또한, 상기의 알칼리의 수용액에 메탄올, 에탄올 등의 수용성 유기 용매나 계면 활성제를 적당량 첨가한 수용액, 또는 감방사선성 수지 조성물을 용해하는 각종 유기 용매를 소량 포함하는 알칼리 수용액을, 현상액으로서 사용할 수 있다. 또한, 현상 방법으로서는, 예를 들면, 퍼들법, 딥핑법, 요동 침지법, 샤워법 등의 적절한 방법을 이용할 수 있다. 현상 시간은, 감방사선성 수지 조성물의 조성에 따라 상이하지만, 예를 들면 30∼120초간으로 할 수 있다. (3) In the developing step, development can be performed on the coating film irradiated with radiation in the step (2) above to remove the radiation portion and form a desired pattern. Examples of the developer used for the developing treatment include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, diethylaminoethanol and di-n. Aqueous solutions of alkali (basic compounds) such as -propylamine, triethylamine, methyldiethylamine, dimethylethanolamine, triethanolamine, tetramethylammonium hydroxide and tetraethylammonium hydroxide can be used. In addition, an aqueous alkali solution containing a small amount of an aqueous solution in which a suitable amount of a water-soluble organic solvent such as methanol and ethanol or a surfactant is added to the aqueous solution of the alkali, or various organic solvents in which the radiation-sensitive resin composition is dissolved can be used as a developer. . As the developing method, for example, a suitable method such as a puddle method, a dipping method, a rocking dipping method or a shower method can be used. Although image development time changes with a composition of a radiation sensitive resin composition, it can be set as 30 to 120 second, for example.
또한, 종래 알려져 있는 감방사선성 수지 조성물은, 현상 시간이 최적치로부터 20∼25초 정도 초과하면 형성한 패턴에 벗겨짐이 발생하기 때문에, 현상 시간을 엄밀하게 제어할 필요가 있다. 이에 대하여, 본 발명의 포지티브형 감방사선성 수지 조성물은, 현상 마진이 높기 때문에, 최적 현상 시간으로부터의 초과 시간이 30 초 이상이 되어도 양호한 패턴 형성이 가능하여, 제품 수율상의 이점이 크다. Moreover, since the peeling generate | occur | produces in the pattern formed when the developing time exceeds about 20 to 25 second from an optimal value in the conventionally known radiation sensitive resin composition, it is necessary to strictly control developing time. On the other hand, since the positive radiation sensitive resin composition of this invention has high image development margin, favorable pattern formation is possible even if the excess time from optimal image development time becomes 30 second or more, and the advantage in product yield is large.
(4) 가열 공정(4) heating process
(4) 가열 공정에 있어서, 상기 (3)의 현상 공정 후에, 패터닝된 박막에 대하여, 바람직하게는 유수(流水) 세정에 의한 린스 처리를 행하고, 이어서, 바람직하게는 고압 수은등 등에 의한 방사선을 전체면에 조사(후노광)함으로써, 박막 중에 잔존하는 1,2-퀴논디아자이드 화합물의 분해 처리를 행한다. 이어서, 핫 플레이트, 오븐 등의 가열 장치를 이용하여, 이 박막을 가열 처리(포스트베이킹 처리)함으로써, 박막의 경화 처리를 행한다. 상기의 후노광에 있어서의 노광량은, 바람직하게는 2,000∼5,000J/m2 정도이다. 또한, 이 경화 처리에 있어서의 소성 온도는, 예를 들면 120∼250℃이다. 가열 시간은, 가열 기기의 종류에 따라 상이하지만, 예를 들면, 핫 플레이트 상에서 가열 처리를 행하는 경우에는 5∼30분간, 오븐 안에서 가열 처리를 행하는 경우에는 30∼90분간으로 할 수 있다. 이때에, 2회 이상의 가열 공정을 행하는 스텝 베이킹법 등을 이용할 수도 있다. 이와 같이 하여, 목적으로 하는 층간 절연막에 대응하는 패턴 형상 박막을 기판의 표면 상에 형성할 수 있다. (4) In the heating step, after the developing step of (3), the patterned thin film is preferably rinsed by running water washing, and then preferably the entire radiation is performed by a high pressure mercury lamp or the like. The surface is irradiated (post-exposure) to decompose the 1,2-quinonediazide compound remaining in the thin film. Subsequently, the thin film is cured by heat treatment (post-baking) the thin film using a heating device such as a hot plate or an oven. The exposure amount in said post-exposure becomes like this. Preferably it is about 2,000-5,000 J / m <2> . In addition, the baking temperature in this hardening process is 120-250 degreeC, for example. Although heating time changes with kinds of a heating apparatus, it can be set as 5 to 30 minutes, for example, when carrying out heat processing on a hotplate, and 30 to 90 minutes when heat processing in an oven. At this time, the step baking method etc. which perform two or more heating processes can also be used. In this way, a patterned thin film corresponding to the target interlayer insulating film can be formed on the surface of the substrate.
이와 같이 하여 형성된 층간 절연막은, 후술하는 실시예로부터 명백해지듯이, 내열성, 내용제성, 저유전성, 광선 투과율, 내광성 및 내드라이 에칭성에 있어서 우수하다. The interlayer insulating film thus formed is excellent in heat resistance, solvent resistance, low dielectric constant, light transmittance, light resistance and dry etching resistance, as will be apparent from the examples described later.
이러한 층간 절연막을 이용하여 액정 표시 소자 등의 전자 부품을 제작할 때에는, 필요에 따라서 드라이 에칭이 행해진다. 이러한 드라이 에칭 공정에 있어서 이용되는 에칭 가스로서는, O2, N2, CF4, SiF6 등을 들 수 있다. 에칭의 방법으로서는, 층간 절연막이 패터닝된 기판과 전극과의 사이에 전압을 인가함으로써, 이온을 기판에 대하여 충돌시키는 반응성 이온 에칭과, 라디칼을 기판에 대하여 충돌시키는 플라즈마 에칭의 2종류가 존재한다. 이들 가스종이나 에칭 방법은, 층간 절연막의 하지(base) 금속종에 따라 적절히 선택된다. 전술한 바와 같이, 본 발명의 포지티브형 감방사선성 수지 조성물로 형성된 층간 절연막은, 드라이 에칭에 대한 우수한 내성을 갖는다. When producing electronic components, such as a liquid crystal display element, using such an interlayer insulation film, dry etching is performed as needed. As etching gas used in this dry etching process, and the like O 2, N 2, CF 4 , SiF 6. As the etching method, there are two types of reactive ion etching, in which ions collide with the substrate by applying a voltage between the substrate on which the interlayer insulating film is patterned, and the electrode, and plasma etching, in which radicals collide with the substrate. These gas species and an etching method are suitably selected according to the base metal species of an interlayer insulation film. As described above, the interlayer insulating film formed from the positive radiation-sensitive resin composition of the present invention has excellent resistance to dry etching.
(실시예)(Example)
이하에, 합성예 및 실시예에 의해 본 발명을 더욱 구체적으로 설명하지만, 본 발명은 이하의 실시예에 한정되는 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Examples.
이하의 합성예에 있어서, 공중합체의 중량 평균 분자량(Mw)의 측정은 하기의 장치 및 조건하, 겔 투과 크로마토그래피(GPC)에 의했다. In the following synthesis examples, the measurement of the weight average molecular weight (Mw) of a copolymer was carried out by gel permeation chromatography (GPC) under the following apparatus and conditions.
장치 : GPC-101(쇼와덴코 가부시키가이샤 제조) Device: GPC-101 (Showa Denko KK)
칼럼 : GPC-KF-801, GPC-KF-802, GPC-KF-803 및 GPC-KF-804를 결합 Column: combine GPC-KF-801, GPC-KF-802, GPC-KF-803 and GPC-KF-804
이동상 : 테트라하이드로푸란 Mobile phase: tetrahydrofuran
검출기 : 시차 굴절계Detector: parallax refractometer
표준 물질 : 단분산 폴리스티렌 Standard material: monodisperse polystyrene
[A] 성분의 [A] component 합성예Synthetic example 및 비교 And comparison 합성예Synthetic example
합성예 1 Synthesis Example 1
공중합체 [A-1]의 합성 Synthesis of Copolymer [A-1]
냉각관 및 교반기를 구비한 플라스크에, 2,2'-아조비스-(2,4-디메틸발레로니트릴) 7질량부와 디에틸렌글리콜에틸메틸에테르 200질량부를 넣었다. 이어서, 메타크릴산 12질량부, 메타크릴산 글리시딜 50질량부, N-사이클로헥실말레이미드 4질량부, 메타크릴산 테트라하이드로푸르푸릴 15질량부, 3-(2-메타크릴로일옥시에틸)옥세탄 10질량부, 스티렌 3질량부 및 펜타에리트리톨테트라키스(3-머캅토프로피오네이트) 2질량부를 넣고 질소 치환한 후, 천천히 교반을 시작했다. 용액의 온도를 70℃로 상승시키고, 반응 용액 온도가 70℃에 도달한 시점에서 중합 개시로 했다. 그 후, 중합 개시로부터 30분 후에 N-사이클로헥실말레이미드 3질량부, 1시간 후에 N-사이클로헥실말레이미드 3질량부를 반응 용액에 적하했다. 그 후, 3시간 보존유지함으로써 공중합체 [A-1]을 포함하는 중합체 용액을 얻었다. 공중합체 [A-1]의 폴리스티렌 환산 중량 평균 분자량(Mw)은 8,000, 분자량 분포(Mw/Mn)는 1.8이었다. 또한, 여기에서 얻어진 중합체 용액의 고형분 농도는 34.5질량%였다. In a flask equipped with a cooling tube and a stirrer, 7 parts by mass of 2,2'-azobis- (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethylmethyl ether were added. Subsequently, 12 parts by mass of methacrylic acid, 50 parts by mass of glycidyl methacrylate, 4 parts by mass of N-cyclohexylmaleimide, 15 parts by mass of tetrahydrofurfuryl methacrylic acid, 3- (2-methacryloyloxy 10 mass parts of ethyl) oxetane, 3 mass parts of styrene, and 2 mass parts of pentaerythritol tetrakis (3-mercaptopropionate) were put, and nitrogen-substituted, and stirring was started slowly. The temperature of the solution was raised to 70 ° C and polymerization was initiated when the reaction solution temperature reached 70 ° C. Thereafter, 3 parts by mass of N-cyclohexyl maleimide and 3 parts by mass of N-cyclohexyl maleimide were added dropwise to the reaction solution after 30 minutes from the start of polymerization. Then, the polymer solution containing copolymer [A-1] was obtained by hold | maintaining for 3 hours. The polystyrene reduced weight average molecular weight (Mw) of copolymer [A-1] was 8,000, and molecular weight distribution (Mw / Mn) was 1.8. In addition, solid content concentration of the polymer solution obtained here was 34.5 mass%.
합성예 2 Synthesis Example 2
공중합체 [A-2]의 합성 Synthesis of Copolymer [A-2]
냉각관 및 교반기를 구비한 플라스크에, 2,2'-아조비스-(2,4-디메틸발레로니트릴) 7질량부와 디에틸렌글리콜에틸메틸에테르 200질량부를 넣었다. 이어서, 메타크릴산 12질량부, 메타크릴산 글리시딜 50질량부, N-사이클로헥실말레이미드 4질량부, 메타크릴산 테트라하이드로푸르푸릴 15질량부, 3-(2-메타크릴로일옥시에틸)옥세탄 8질량부, 메타크릴산 4-하이드록시벤질 5질량부 및 펜타에리트리톨테트라키스(3-머캅토프로피오네이트) 2질량부를 넣고 질소 치환한 후, 천천히 교반을 시작했다. 용액의 온도를 70℃로 상승시키고, 반응 용액 온도가 70℃에 도달한 시점에서 중합 개시로 했다. 그 후, 중합 개시로부터 30분 후에 N-사이클로헥실말레이미드 3질량부, 1시간 후에 N-사이클로헥실말레이미드 3질량부를 반응 용액에 적하했다. 그 후, 3시간 보지함으로써 공중합체 [A-2]를 포함하는 중합체 용액을 얻었다. 공중합체 [A-2]의 폴리스티렌 환산 중량 평균 분자량(Mw)은 9,000, 분자량 분포(Mw/Mn)는 1.9였다. 또한, 여기에서 얻어진 중합체 용액의 고형분 농도는 34.0질량%였다. In a flask equipped with a cooling tube and a stirrer, 7 parts by mass of 2,2'-azobis- (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethylmethyl ether were added. Subsequently, 12 parts by mass of methacrylic acid, 50 parts by mass of glycidyl methacrylate, 4 parts by mass of N-cyclohexylmaleimide, 15 parts by mass of tetrahydrofurfuryl methacrylic acid, 3- (2-methacryloyloxy 8 mass parts of ethyl) oxetane, 5 mass parts of 4-hydroxybenzyl methacrylic acid, and 2 mass parts of pentaerythritol tetrakis (3-mercaptopropionate) were put, and nitrogen-substituted, and stirring was started slowly. The temperature of the solution was raised to 70 ° C and polymerization was initiated when the reaction solution temperature reached 70 ° C. Thereafter, 3 parts by mass of N-cyclohexyl maleimide and 3 parts by mass of N-cyclohexyl maleimide were added dropwise to the reaction solution after 30 minutes from the start of polymerization. Then, the polymer solution containing copolymer [A-2] was obtained by holding for 3 hours. The polystyrene reduced weight average molecular weight (Mw) of copolymer [A-2] was 9,000, and molecular weight distribution (Mw / Mn) was 1.9. In addition, solid content concentration of the polymer solution obtained here was 34.0 mass%.
합성예 3 Synthesis Example 3
공중합체 [A-3]의 합성 Synthesis of Copolymer [A-3]
냉각관 및 교반기를 구비한 플라스크에, 2,2'-아조비스-(2,4-디메틸발레로니트릴) 7질량부와 디에틸렌글리콜에틸메틸에테르 200질량부를 넣었다. 이어서, 메타크릴산 12질량부, 메타크릴산 글리시딜 50질량부, N-사이클로헥실말레이미드 4질량부, 메타크릴산 테트라하이드로푸르푸릴 15질량부, 3-(2-메타크릴로일옥시에틸)옥세탄 8질량부, 아크릴로일모르폴린 5질량부 및 펜타에리트리톨테트라키스(3-머캅토프로피오네이트) 2질량부를 넣고 질소 치환한 후, 천천히 교반을 시작했다. 용액의 온도를 70℃로 상승시키고, 반응 용액 온도가 70℃에 도달한 시점에서 중합 개시로 했다. 그 후, 중합 개시로부터 30분 후에 N-사이클로헥실말레이미드 3질량부, 1시간 후에 N-사이클로헥실말레이미드 3질량부를 반응 용액에 적하했다. 그 후, 3시간 보지함으로써 공중합체 [A-3]을 포함하는 중합체 용액을 얻었다. 공중합체 [A-3]의 폴리스티렌 환산 중량 평균 분자량(Mw)은 9,000, 분자량 분포(Mw/Mn)는 2.0이었다. 또한, 여기에서 얻어진 중합체 용액의 고형분 농도는 34.8질량%였다. In a flask equipped with a cooling tube and a stirrer, 7 parts by mass of 2,2'-azobis- (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethylmethyl ether were added. Subsequently, 12 parts by mass of methacrylic acid, 50 parts by mass of glycidyl methacrylate, 4 parts by mass of N-cyclohexylmaleimide, 15 parts by mass of tetrahydrofurfuryl methacrylic acid, 3- (2-methacryloyloxy 8 mass parts of ethyl) oxetane, 5 mass parts of acryloyl morpholine, and 2 mass parts of pentaerythritol tetrakis (3-mercaptopropionate) were put, and nitrogen-substituted, and stirring was started slowly. The temperature of the solution was raised to 70 ° C and polymerization was initiated when the reaction solution temperature reached 70 ° C. Thereafter, 3 parts by mass of N-cyclohexyl maleimide and 3 parts by mass of N-cyclohexyl maleimide were added dropwise to the reaction solution after 30 minutes from the start of polymerization. Then, the polymer solution containing copolymer [A-3] was obtained by holding for 3 hours. The polystyrene reduced weight average molecular weight (Mw) of the copolymer [A-3] was 9,000, and molecular weight distribution (Mw / Mn) was 2.0. In addition, solid content concentration of the polymer solution obtained here was 34.8 mass%.
합성예 4 Synthesis Example 4
공중합체 [A-4]의 합성 Synthesis of Copolymer [A-4]
냉각관 및 교반기를 구비한 플라스크에, 2,2'-아조비스-(2,4-디메틸발레로니트릴) 8질량부와 디에틸렌글리콜에틸메틸에테르 200질량부를 넣었다. 이어서, 메타크릴산 11질량부, 테트라하이드로푸르푸릴메타크릴레이트 12질량부, 메타크릴산 글리시딜 40질량부, N-사이클로헥실말레이미드 15질량부, 라우릴메타크릴레이트 10질량부 및, α-메틸스티렌다이머 3질량부를 넣고 질소 치환한 후, 천천히 교반을 시작했다. 용액의 온도를 70℃로 상승시키고, 이 온도를 5시간 보지함으로써 공중합체 [A-4]를 포함하는 중합체 용액을 얻었다. 공중합체 [A-4]의 폴리스티렌 환산 중량 평균 분자량(Mw)은 8,000, 분자량 분포(Mw/Mn)는 2.3이었다. 또한, 여기에서 얻어진 중합체 용액의 고형분 농도는 34.9질량%였다. In a flask equipped with a cooling tube and a stirrer, 8 parts by mass of 2,2'-azobis- (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethylmethyl ether were added. Then, 11 parts by mass of methacrylic acid, 12 parts by mass of tetrahydrofurfuryl methacrylate, 40 parts by mass of glycidyl methacrylate, 15 parts by mass of N-cyclohexylmaleimide, 10 parts by mass of lauryl methacrylate, and After 3 mass parts of (alpha) -methylstyrene dimers were substituted for nitrogen, stirring was started slowly. The polymer solution containing copolymer [A-4] was obtained by raising the temperature of a solution to 70 degreeC and holding this temperature for 5 hours. The polystyrene reduced weight average molecular weight (Mw) of the copolymer [A-4] was 8,000, and molecular weight distribution (Mw / Mn) was 2.3. In addition, solid content concentration of the polymer solution obtained here was 34.9 mass%.
합성예 5 Synthesis Example 5
공중합체 [A-5]의 합성 Synthesis of Copolymer [A-5]
냉각관 및 교반기를 구비한 플라스크에, 2,2'-아조비스-(2,4-디메틸발레로니트릴) 7질량부와 디에틸렌글리콜에틸메틸에테르 200질량부를 넣었다. 이어서, 메타크릴산 12질량부, 메타크릴산 글리시딜 50질량부, N-사이클로헥실말레이미드 10질량부, 메타크릴산 테트라하이드로푸르푸릴 15질량부, 메타크릴산 4-하이드록시벤질 8질량부, 아크릴로일모르폴린 5질량부 및 α-메틸스티렌다이머 3질량부를 넣고 질소 치환한 후, 천천히 교반을 시작했다. 용액의 온도를 70℃로 상승시키고, 이 온도를 5시간 보지함으로써 공중합체 [A-5]를 포함하는 중합체 용액을 얻었다. 공중합체 [A-5]의 폴리스티렌 환산 중량 평균 분자량(Mw)은 9,000, 분자량 분포(Mw/Mn)는 2.3이었다. 또한, 여기에서 얻어진 중합체 용액의 고형분 농도는 35.3질량%였다. In a flask equipped with a cooling tube and a stirrer, 7 parts by mass of 2,2'-azobis- (2,4-dimethylvaleronitrile) and 200 parts by mass of diethylene glycol ethylmethyl ether were added. Subsequently, 12 parts by mass of methacrylic acid, 50 parts by mass of glycidyl methacrylate, 10 parts by mass of N-cyclohexylmaleimide, 15 parts by mass of tetrahydrofurfuryl methacrylate, and 8 parts by mass of 4-hydroxybenzyl methacrylic acid After adding 5 parts by mass of acryloyl morpholine and 3 parts by mass of α-methylstyrene dimer and nitrogen-substituted, stirring was started slowly. The polymer solution containing copolymer [A-5] was obtained by raising the temperature of a solution to 70 degreeC and holding this temperature for 5 hours. The polystyrene reduced weight average molecular weight (Mw) of the copolymer [A-5] was 9,000, and molecular weight distribution (Mw / Mn) was 2.3. In addition, solid content concentration of the polymer solution obtained here was 35.3 mass%.
실시예 1 Example 1
[감방사선성 수지 조성물의 조제] [Preparation of radiation sensitive resin composition]
[A] 성분으로서 상기 합성예 1에서 합성한 공중합체 [A-1]을 함유하는 용액을, 공중합체 [A-1] 100질량부(고형분)에 상당하는 양, [B] 성분으로서 4,4'-[1-[4-[1-[4-하이드록시페닐]-1-메틸에틸]페닐]에틸리덴]비스페놀(1.0몰)과 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드(2.0몰)와의 축합물 [B-1] 15질량부 및, [C] 성분으로서, 팔미트산 4질량부, [F] 성분으로서, 실리콘계 계면 활성제(가부시키가이샤 토레·다우코닝 제조의 「SH 8400 FLUID」) 0.1질량부를 혼합하여, 고형분 농도가 23질량%가 되도록 디에틸렌글리콜에틸메틸에테르에 용해시킨 후, 구경 0.2㎛의 멤브레인필터로 여과하여, 감방사선성 수지 조성물의 용액을 조제했다. The amount of the solution containing the copolymer [A-1] synthesized in Synthesis Example 1 as the component [A], corresponding to 100 parts by mass (solid content) of the copolymer [A-1], 4, as the component [B] 4 '-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] bisphenol (1.0 mole) and 1,2-naphthoquinonediazide-5-sulfonic acid chloride 15 mass parts of condensate with (2.0 mol) [B-1] and 4 mass parts of palmitic acid and [F] component as a [C] component, and a silicone type surfactant (made by Toray Dow Corning, Inc. SH 8400 FLUID ''), 0.1 parts by mass was mixed, dissolved in diethylene glycol ethyl methyl ether so that the solid content concentration was 23% by mass, and then filtered through a membrane filter having a diameter of 0.2 µm to prepare a solution of the radiation-sensitive resin composition. .
[실시예 2∼17 및 비교예 1∼6] [Examples 2 to 17 and Comparative Examples 1 to 6]
각 성분의 종류 및 양을 표 1에 기재한 바와 같이 한 것 외는, 실시예 1과 동일하게 하여 포지티브형 감방사선성 수지 조성물을 조제했다. Except having performed the kind and quantity of each component as Table 1, it carried out similarly to Example 1, and prepared the positive radiation sensitive resin composition.
표 1 중의 성분의 약칭은 다음의 화합물을 의미한다. The abbreviation of the component of Table 1 means the following compound.
[B-1] : 4,4'-[1-[4-[1-[4-하이드록시페닐]-1-메틸에틸]페닐]에틸리덴]비스페놀(1.0몰)과 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드(2.0몰)와의 축합물 [B-1]: 4,4 '-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] bisphenol (1.0 mole) and 1,2-naphtho Condensate with quinonediazide-5-sulfonic acid chloride (2.0 moles)
[B-2] : 1,1,1-트리(p-하이드록시페닐)에탄(1.0몰)과 1,2-나프토퀴논디아자이드-5-술폰산 클로라이드(2.0몰)와의 축합물 [B-2]: Condensate of 1,1,1-tri (p-hydroxyphenyl) ethane (1.0 mol) with 1,2-naphthoquinonediazide-5-sulfonic acid chloride (2.0 mol)
[C-1] : 팔미트산 [C-1]: palmitic acid
[C-2] : 스테아르산 [C-2]: stearic acid
[C-3] : 테트라데칸 2산 [C-3]: tetradecane diacid
[C-4] : 1-도데칸올 [C-4]: 1-dodecanol
[C-5] : 1,12-도데칸디올 [C-5]: 1,12-dodecanediol
[C-6] : 1,2-에폭시테트라데칸 [C-6]: 1,2-epoxytetedecane
[C-7] : 1,2-에폭시헥사데칸 [C-7]: 1,2-epoxyhexadecane
[C-8] : 스테아르산 글리시딜 [C-8]: Glycidyl Stearate
[C-9] : 1,3-에폭시-2-에틸-2-도데칸 [C-9]: 1,3-epoxy-2-ethyl-2-dodecane
[C-10] : 1-도데칸술폰산 [C-10]: 1-dodecanesulfonic acid
[F-1] : 실리콘계 계면 활성제(가부시키가이샤 토레·다우코닝 제조의 「SH 8400 FLUID」)[F-1]: Silicone surfactant ("SH 8400 FLUID" manufactured by Toray Dow Corning, Inc.)
[F-2] : 불소계 계면 활성제 FTX-218(가부시키가이샤 네오스 제조) [F-2]: Fluorine-based surfactant FTX-218 (manufactured by Neos Co., Ltd.)
[G-1] : γ-글리시독시프로필트리메톡시실란 [G-1]: γ-glycidoxypropyltrimethoxysilane
[H-1] : 펜타에리트리톨테트라키스[3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트](상품명 IRGANOX L115, 치바·스페셜티·케미칼스 가부시키가이샤 제조) [H-1]: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name IRGANOX L115, manufactured by Chiba Specialty Chemicals Co., Ltd.) )
[H-2] : 티오디에틸렌비스[3-(3,5-디-tert-부틸-4-하이드록시페닐)프로피오네이트](상품명 IRGANOX L101, 치바·스페셜티·케미칼스 가부시키가이샤 제조) [H-2]: thiodiethylene bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name IRGANOX L101, manufactured by Chiba Specialty Chemicals Co., Ltd.)
[비교예 5] [Comparative Example 5]
비교예 5에 있어서, 실시예 1에 있어서 팔미트산 대신에, 발레르산(화학식: CH3(CH2)3COOH)을 이용하고 다른 조성물은 동일하게 하여 포지티브형 감방사선성 수지 조성물을 조제하여 평가했다. 그 결과, 도포성, 감도, 내용제성, 내열성, 광선 투과율은 양호했지만, 콘택트 홀 형상이 불량이고, 내드라이 에칭성도 1.51㎛였다. In Comparative Example 5, instead of palmitic acid in Example 1, valeric acid (Chemical Formula: CH 3 (CH 2 ) 3 COOH) was used, and the other compositions were prepared in the same manner to prepare a positive radiation-sensitive resin composition. Evaluated. As a result, although applicability | paintability, a sensitivity, solvent resistance, heat resistance, and light transmittance were favorable, the contact hole shape was bad and dry etching resistance was 1.51 micrometers.
<층간 절연막의 물성 평가> <Evaluation of Physical Properties of Interlayer Insulating Film>
상기와 같이 조제한 감방사선성 수지 조성물을 사용하여, 이하와 같이 층간 절연막으로서의 각종 물성을 평가했다. Various physical properties as an interlayer insulation film were evaluated as follows using the radiation sensitive resin composition prepared as mentioned above.
[도포성(세로 줄무늬 얼룩, 안개 얼룩)의 평가] [Evaluation of coating properties (vertical streaks, fog stains)]
550mm×650mm의 크롬 성막 유리 상에, 조제한 조성물 용액을, 슬릿다이 코터 (TR632105-CL, 토쿄오카코교 가부시키가이샤 제조)를 이용하여 도포했다. 0.5Torr까지 감압 건조한 후, 핫 플레이트 상에서 100℃에서 2분간 프리베이킹하여 도막을 형성하고, 추가로 2,000J/m2의 노광량으로 노광함으로써, 크롬 성막 유리의 상면으로부터의 막두께가 4㎛인 막을 형성했다. The prepared composition solution was apply | coated on 550 mm x 650 mm chromium film-forming glass using the slit-die coater (TR632105-CL, the Tokyo Corporation make). After drying under reduced pressure to 0.5 Torr, the film was formed by prebaking at 100 ° C. for 2 minutes on a hot plate, and then exposed at an exposure dose of 2,000 J / m 2 to form a film having a film thickness of 4 μm from the upper surface of the chromium film-forming glass. Formed.
막 표면을 나트륨 램프로 비추어, 육안으로 도포막면을 확인했다. 세로 줄무늬 얼룩(도포 방향, 또는 그것에 교차하는 방향으로 생기는 1줄 또는 복수줄의 직선의 얼룩), 안개 얼룩(구름 형상의 얼룩)을 분명히 확인할 수 있었던 경우는 ×, 거의 확인할 수 없었던 경우는 ○라고 표기한다. 결과를 표 1, 표 2에 나타낸다. The film surface was illuminated with a sodium lamp, and the coating film surface was visually confirmed. When vertical stripe stain (stain of one line or plural lines of straight lines occurring in the direction of application or the direction crossing it), fog stain (cloud-like stain) were confirmed clearly ×, it was ○ Mark it. The results are shown in Table 1 and Table 2.
[감도의 평가] [Evaluation of sensitivity]
표 1, 표 2에 기재된 각각의 조성물의 용액을, 스피너를 이용하여 실리콘 기판 상에 도포한 후, 90℃에서 3분간 핫 플레이트 상에서 프리베이킹하여 막두께 4.5㎛의 도막을 형성했다. 캐논 가부시키가이샤 제조 PLA-501F 노광기(초고압 수은 램프)를 이용하여, 노광 시간을 변화시켜, 소정의 패턴을 갖는 패턴 마스크를 통하여 도막에 노광을 행했다. 이어서, 농도 0.5질량%의 테트라메틸암모늄하이드록사이드 수용액(현상액)을 이용하여, 퍼들법에 의해 25℃에서 현상 처리를 행했다. 현상 처리의 시간은, 70초로 했다. 현상 처리 후, 초순수에서 1분간, 도막의 유수 세정을 행하고, 건조시켜 웨이퍼 상에 패턴을 형성했다. 이러한 노광 및 현상 처리에 있어서, 6.0㎛의 라인·앤드·스페이스(1대 1)의 스페이스·패턴이 완전히 용해하기 위해 필요한 노광량을 측정했다. 각 조성물에 있어서의 이 값을 감도 [J/m2]로서 표 2에 나타냈다. 이 값이 700J/m2 이하의 경우에 감도가 양호하다고 판단된다. The solution of each composition of Table 1 and Table 2 was apply | coated on the silicon substrate using the spinner, and then prebaked at 90 degreeC for 3 minutes on the hotplate, and the coating film of 4.5 micrometers in thickness was formed. Exposure time was changed using Canon PLA-501F exposure machine (super high pressure mercury lamp), and exposure was performed to the coating film through the pattern mask which has a predetermined pattern. Next, the image development process was performed at 25 degreeC by the puddle method using the tetramethylammonium hydroxide aqueous solution (developer) of 0.5 mass% of concentration. The development processing time was set to 70 seconds. After the development treatment, the coating film was washed with ultrapure water for 1 minute, dried, and a pattern was formed on the wafer. In this exposure and image development, the exposure amount required for complete dissolution of the space pattern of 6.0 µm line and space (one to one) was measured. This value in each composition was shown in Table 2 as a sensitivity [J / m 2] . It is judged that the sensitivity is good when this value is 700 J / m 2 or less.
[콘택트 홀 형상의 평가] [Evaluation of Contact Hole Shape]
[감도의 평가]와 동일하게 하여, 스피너를 이용하여 실리콘 기판 상에 도포한 후, 프리베이킹 온도를 75℃에서 3분간, 90℃에서 3분간의 2가지 조건에 의해, 핫 플레이트 상에서 프리베이킹하여 막두께 4.5㎛의 막두께가 되도록 도막을 형성했다. 캐논 가부시키가이샤 제조 PLA-501F 노광기(초고압 수은 램프)를 이용하여, [감도의 평가]에 있어서 평가된 필요 노광량으로, 10㎛×10㎛의 콘택트 홀 패턴의 마스크를 통하여 도막의 노광을 행했다. 이어서, 농도 0.5질량%의 테트라메틸암모늄하이드록사이드 수용액(현상액)을 이용하여, 퍼들법에 의해 25℃에서 현상 처리를 행했다. 현상 처리의 시간은, 70초로 했다. 현상 처리 후, 초순수에서 1분, 도막의 유수 세정을 행하고, 건조시켜 웨이퍼 상에 콘택트 홀 패턴을 형성했다. 그 형성한 패턴을 SEM(주사 전자 현미경)으로 형상을 관찰했다. In the same manner as in [evaluation of sensitivity], after coating on a silicon substrate using a spinner, the prebaking temperature was prebaked on a hot plate under two conditions of 3 minutes at 75 ° C and 3 minutes at 90 ° C. The coating film was formed so that it might become a film thickness of 4.5 micrometers. The coating film was exposed through the mask of the contact hole pattern of 10 micrometers x 10 micrometers by the required exposure amount evaluated in [evaluation of sensitivity] using the Canon PLA-501F exposure machine (super high pressure mercury lamp). Next, the image development process was performed at 25 degreeC by the puddle method using the tetramethylammonium hydroxide aqueous solution (developer) of 0.5 mass% of concentration. The development processing time was set to 70 seconds. After the development treatment, the coated film was washed with ultrapure water for one minute, dried, and a contact hole pattern was formed on the wafer. The formed pattern was observed with a SEM (scanning electron microscope).
프리베이킹 온도를 75℃에서 3분간과 프리베이킹 온도를 90℃에서 3분간의 2가지 조건에서 제작한 콘택트 홀 패턴에 큰 차이가 없는 경우, 프리베이킹의 온도 변화에 대한 형상 안정성이 높고, 콘택트 홀 형상은 양호하다고 할 수 있다. 한편, 프리베이킹 온도의 변화에 대하여, 콘택트 홀 크기가 크게 변화하거나, 형상이 크게 변화한 경우, 프리베이킹의 온도 변화에 대한 안정성이 낮고, 콘택트 홀 형상은 불량하다고 할 수 있다. 콘택트 홀 형상이 양호라고 판단한 경우를 「○」, 불량이라고 판단한 경우를 「×」라고 했다. 결과를 표 1, 표 2에 나타낸다. When there is no significant difference between the contact hole patterns produced under two conditions of prebaking temperature at 75 ° C. for 3 minutes and prebaking temperature at 90 ° C. for 3 minutes, the shape stability to the temperature change of the prebaking is high and the contact hole is high. The shape can be said to be good. On the other hand, when the contact hole size changes significantly or the shape changes significantly with respect to the change in the prebaking temperature, it can be said that the stability against the temperature change of the prebaking is low and the contact hole shape is poor. The case where it judged as "(circle)" and the case where it judged that contact hole shape was favorable was made into "x". The results are shown in Table 1 and Table 2.
[내용제성의 평가] [Evaluation of solvent resistance]
[감도의 평가]의 경우와 동일하게 하여, 스피너를 이용하여 실리콘 기판 상에 도포한 후, 90℃에서 3분간 핫 플레이트 상에서 프리베이킹하여 막두께 4.5㎛의 도막을 형성했다. 그 후 노광하지 않고 [감도의 평가]의 경우와 동일하게 하여 현상하고, 캐논 가부시키가이샤 제조 PLA-501F 노광기(초고압 수은 램프)를 이용하여, 적분 조사량이 3,000J/m2가 되도록 도막을 노광하고, 그 후 클린 오븐 내에서 220℃에서 1시간 가열하여 경화막을 얻었다. 여기에서, 얻어진 경화막의 막두께(T1)를 측정했다. 이어서, 이 경화막이 형성된 실리콘 기판을, 70℃로 온도 제어된 디메틸술폭사이드 중에 20분간 침지시킨 후, 경화막의 막두께(t1)를 측정하고, 침지에 의한 막두께 변화율 {|t1-T1|/T1}×100〔%〕를 산출했다. 막두께 변화율의 산출 결과를 표 1, 표 2에 나타낸다. 이 값이 5% 이하일 때, 내용제성은 양호라고 판단된다. Similarly to the case of [evaluation of sensitivity], after apply | coating on a silicon substrate using a spinner, it prebaked at 90 degreeC for 3 minutes on the hotplate, and formed the coating film of 4.5 micrometers in thickness. After that, development was carried out in the same manner as in the case of [evaluation of sensitivity] without exposure, and the coating film was exposed so that the integral irradiation amount was 3,000 J / m 2 using a Canon PLA-501F exposure machine (ultra high pressure mercury lamp). Then, it heated in 220 degreeC for 1 hour in the clean oven, and obtained the cured film. Here, the film thickness (T1) of the obtained cured film was measured. Subsequently, the silicon substrate on which this cured film was formed was immersed for 20 minutes in dimethyl sulfoxide temperature-controlled at 70 degreeC, and the film thickness t1 of a cured film was measured, and the film thickness change rate by immersion {| t1-T1 | / T1} × 100 [%] was calculated. Table 1 and Table 2 show the results of the calculation of the film thickness change rate. When this value is 5% or less, it is judged that solvent resistance is favorable.
[내열성의 평가] [Evaluation of Heat Resistance]
상기의 내용제성 평가의 경우와 동일하게 하여 실리콘 기판 상에 경화막을 형성하고, 얻어진 경화막의 막두께(T2)를 측정했다. 이어서, 이 실리콘 기판을 클린 오븐 내에서 240℃에서 1시간 추가 베이킹한 후, 당해 경화막의 막두께(t2)를 측정하고, 추가 베이킹에 의한 막두께 변화율 {|t2-T2|/T2}×100〔%〕를 산출했다. 막두께 변화율의 산출 결과를 표 1, 표 2에 나타낸다. 이 값이 5% 이하일 때, 내열성이 양호라고 할 수 있다. The cured film was formed on the silicon substrate similarly to the case of said solvent resistance evaluation, and the film thickness (T2) of the obtained cured film was measured. Subsequently, after further baking this silicon substrate at 240 degreeC in clean oven for 1 hour, the film thickness t2 of the said cured film was measured, and the film thickness change rate by further baking {| t2-T2 | / T2} x100 [%] Was calculated. Table 1 and Table 2 show the results of the calculation of the film thickness change rate. When this value is 5% or less, it can be said that heat resistance is favorable.
[광선 투과율의 평가] [Evaluation of Light Transmittance]
상기의 내용제성 평가에 있어서, 실리콘 기판 대신에 유리 기판 「코닝 7059」(코닝사 제조)을 이용한 것 이외는 동일하게 하여, 유리 기판 상에 경화막을 형성했다. 분광 광도계 「150-20형 더블빔」(가부시키가이샤 히타치세이사쿠쇼 제조)을 이용하여, 이 경화막을 갖는 유리 기판의 광선 투과율〔%〕을, 400∼800nm의 범위의 파장에서 측정했다. 그때의 최저 광선 투과율의 값을 표 1, 표 2에 나타낸다. 이 최저 광선 투과율의 값이 95% 이상일 때, 투명성은 양호라고 판단된다. In the said solvent resistance evaluation, the cured film was formed on the glass substrate similarly except having used the glass substrate "Corning 7059" (made by Corning Corporation) instead of the silicon substrate. Using the spectrophotometer "150-20 type double beam" (made by Hitachi Seisakusho Co., Ltd.), the light transmittance [%] of the glass substrate which has this cured film was measured in the wavelength of 400-800 nm. Table 1 and Table 2 show the values of the minimum light transmittance at that time. When the value of this minimum light transmittance is 95% or more, it is judged that transparency is favorable.
[층간 절연막의 내드라이 에칭성의 평가] [Evaluation of dry etching resistance of interlayer insulation film]
상기의 내용제성 평가의 경우와 동일하게 하여 실리콘 기판 상에 경화막을 형성하고, 드라이 에칭 장치 CDE-80N(가부시키가이샤 시바우라 메카트로닉스 제조)을 이용하여, 에칭 가스 CF4 50ml/분, O2 10ml/분, 출력 400mW, 에칭 시간 90초의 조건에서 드라이 에칭을 행하여, 처리 전후의 막두께 측정을 행했다. 결과를 표 1, 표 2에 나타낸다. 막두께 감소가 1.00㎛ 미만일 때, 내드라이 에칭성은 양호하다고 할 수 있다. In the same manner as in the case of solvent resistance evaluation, a cured film was formed on a silicon substrate, and etching gas CF 4 50 ml / min, O 2 10 ml was used with dry etching apparatus CDE-80N (manufactured by Shibaura Mechatronics Co., Ltd.). Dry etching was performed under conditions of / min, an output of 400 mW, and an etching time of 90 seconds to measure the film thickness before and after the treatment. The results are shown in Table 1 and Table 2. When the film thickness decrease is less than 1.00 µm, the dry etching resistance can be said to be good.
Claims (6)
[B] 1,2-퀴논디아자이드 화합물 및,
[C] 하기 일반식 (1)로 나타나는 화합물을 포함하는 감방사선성 수지 조성물:
(식 (1) 중, X는, 탄소수 6∼20의 2가의 직쇄상 지방족 탄화 수소기이고, Y1 및 Y2는, 각각 독립적으로, 단결합, 에스테르 결합, 아미드 결합 또는 우레탄 결합이고, R1 및 R2는, 각각 독립적으로, 수소 원자, 탄소수 1∼6의 알킬기, 술포기, 술포페닐기, 또는 하기식 (2)의 (i)∼(vi)의 어느 것으로 나타나는 기이고; 단, Y1 및 Y2가 동시에 단결합일 때, R1 및 R2가 수소원자 또는 탄소수 1∼6의 알킬기인 경우는 없음)
(2)
(식 (i)∼(vi) 중, R3은, 수소 원자 또는 탄소수 1∼6의 알킬기이고, R4는, 수소 원자 또는 메틸기이고, m은, 0∼6의 정수이고, 단, 상기식 (1)의 Y1 또는 Y2가 단결합일 때, 이 Y1 또는 Y2와 연결하는 R3 또는 R4에 있어서의 m은 0임).[A] alkali-soluble resin,
[B] 1,2-quinonediazide compound, and
[C] A radiation sensitive resin composition comprising a compound represented by the following General Formula (1):
(Wherein (1), X is a divalent straight-chain aliphatic hydrocarbon group having a carbon number of 6~20, Y 1 and Y 2 are, each independently, a single bond, an ester bond, an amide bond or a urethane bond, R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a sulfo group, a sulfophenyl group, or a group represented by any of (i) to (vi) of the following formula (2); When 1 and Y 2 are a single bond at the same time, R 1 and R 2 are not a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)
(2)
(In formula (i)-(vi), R <3> is a hydrogen atom or a C1-C6 alkyl group, R <4> is a hydrogen atom or a methyl group, m is an integer of 0-6, and is a said formula When Y 1 or Y 2 in (1) is a single bond, m in R 3 or R 4 connecting with Y 1 or Y 2 is 0).
[A] 성분의 알칼리 가용성 수지가, (a1) 불포화 카본산 또는 불포화 카본산 무수물, 및 (a2) 에폭시기 함유 불포화 화합물을 포함하는 불포화 화합물의 공중합체인 감방사선성 수지 조성물. The method of claim 1,
The radiation sensitive resin composition whose alkali-soluble resin of the [A] component is a copolymer of the unsaturated compound containing (a1) unsaturated carboxylic acid or unsaturated carboxylic anhydride, and (a2) epoxy group containing unsaturated compound.
[C] 성분의 화합물이, 탄소수 8∼18의 지방산 및 탄소수 8∼18의 알킬기를 갖는 에폭시 화합물의 적어도 한쪽을 포함하는 것을 특징으로 하는 감방사선성 수지 조성물. The method of claim 1,
The radiation sensitive resin composition characterized by the compound of the [C] component containing at least one of the C8-C18 fatty acid and the epoxy compound which has a C8-C18 alkyl group.
층간 절연막 형성용인 감방사선성 수지 조성물. The method according to any one of claims 1, 2 or 3,
A radiation sensitive resin composition for forming an interlayer insulating film.
(2) 공정 (1)에서 형성한 도막의 적어도 일부에 방사선을 조사하는 공정,
(3) 공정 (2)에서 방사선이 조사된 도막을 현상하는 공정 및,
(4) 공정 (3)에서 현상된 도막을 가열하는 공정
을 포함하는 층간 절연막을 형성하는 방법. (1) Process of forming the coating film of radiation sensitive resin composition of Claim 4 on a board | substrate,
(2) irradiating at least a part of the coating film formed in step (1) with radiation;
(3) developing the coating film irradiated with radiation in step (2), and
(4) Step of heating the coating film developed in Step (3)
Method for forming an interlayer insulating film comprising a.
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KR20150073077A (en) * | 2013-12-20 | 2015-06-30 | 제이에스알 가부시끼가이샤 | Method for forming hole pattern, resin composition for forming hole pattern, and layered product |
KR20190130127A (en) * | 2017-03-29 | 2019-11-21 | 도레이 카부시키가이샤 | Photosensitive composition, cured film, and organic electroluminescence display |
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JP5966268B2 (en) * | 2011-07-22 | 2016-08-10 | Jsr株式会社 | Array substrate, liquid crystal display element, and method of manufacturing array substrate |
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TWI477914B (en) * | 2012-03-29 | 2015-03-21 | Chi Mei Corp | Photo-curing polysiloxane composition and protecting film and element containing said protecting film |
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JPH06258824A (en) * | 1993-03-02 | 1994-09-16 | Sumitomo Chem Co Ltd | Positive type resist composition |
JPH08286365A (en) * | 1995-04-18 | 1996-11-01 | Mitsubishi Chem Corp | Radiation sensitive coating composition |
US7001705B2 (en) * | 2002-04-18 | 2006-02-21 | Nissan Chemical Industries, Ltd. | Positively photosensitive resin composition and method of pattern formation |
JP4455499B2 (en) * | 2003-07-16 | 2010-04-21 | Azエレクトロニックマテリアルズ株式会社 | Photosensitive resin composition |
EP1778759B1 (en) * | 2004-07-07 | 2008-11-12 | Promerus, LLC | Photosensitive dielectric resin compositions and their uses |
JP4753237B2 (en) * | 2005-07-25 | 2011-08-24 | Azエレクトロニックマテリアルズ株式会社 | Photosensitive resin composition |
US7687208B2 (en) * | 2006-08-15 | 2010-03-30 | Asahi Kasei Emd Corporation | Positive photosensitive resin composition |
JP4849251B2 (en) * | 2007-01-18 | 2012-01-11 | Jsr株式会社 | Radiation-sensitive resin composition, interlayer insulating film and microlens, and production method thereof |
JP5029836B2 (en) * | 2008-03-19 | 2012-09-19 | Jsr株式会社 | Radiation-sensitive resin composition, interlayer insulating film and microlens, and production method thereof |
-
2010
- 2010-12-01 JP JP2010268203A patent/JP2011138116A/en active Pending
- 2010-12-02 CN CN201010576964.2A patent/CN102087473B/en active Active
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- 2010-12-03 TW TW099142026A patent/TWI481956B/en active
Cited By (2)
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KR20150073077A (en) * | 2013-12-20 | 2015-06-30 | 제이에스알 가부시끼가이샤 | Method for forming hole pattern, resin composition for forming hole pattern, and layered product |
KR20190130127A (en) * | 2017-03-29 | 2019-11-21 | 도레이 카부시키가이샤 | Photosensitive composition, cured film, and organic electroluminescence display |
Also Published As
Publication number | Publication date |
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CN102087473B (en) | 2014-04-16 |
TW201129862A (en) | 2011-09-01 |
CN102087473A (en) | 2011-06-08 |
JP2011138116A (en) | 2011-07-14 |
TWI481956B (en) | 2015-04-21 |
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