JP6360871B2 - 感光性樹脂組成物、保護膜、および液晶表示素子 - Google Patents
感光性樹脂組成物、保護膜、および液晶表示素子 Download PDFInfo
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- JP6360871B2 JP6360871B2 JP2016240227A JP2016240227A JP6360871B2 JP 6360871 B2 JP6360871 B2 JP 6360871B2 JP 2016240227 A JP2016240227 A JP 2016240227A JP 2016240227 A JP2016240227 A JP 2016240227A JP 6360871 B2 JP6360871 B2 JP 6360871B2
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- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
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- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- XOWPJAUIFINUMO-UHFFFAOYSA-N triethoxy-[3-[2-(oxetan-2-yl)butoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC(CC)C1CCO1 XOWPJAUIFINUMO-UHFFFAOYSA-N 0.000 description 1
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- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 1
- HBMURCLMVGIIAQ-UHFFFAOYSA-N trimethoxy-[3-[2-(oxetan-2-yl)butoxy]propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC(CC)C1CCO1 HBMURCLMVGIIAQ-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- XYRAEZLPSATLHH-UHFFFAOYSA-N trisodium methoxy(trioxido)silane Chemical compound [Na+].[Na+].[Na+].CO[Si]([O-])([O-])[O-] XYRAEZLPSATLHH-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
-
- 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
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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Description
条件(I):主鎖は、さらに、カルボン酸またはカルボン酸無水物を含む不飽和モノマー(a1−1)から誘導された繰り返し単位を含み、カルボン酸またはカルボン酸無水物を含む不飽和モノマー(a1−1)は、カルボン酸基構造および不飽和結合を含むか、カルボン酸無水物基構造および不飽和結合を含む。
条件(II):シロキサン系モノマー(a2)は、下記の式(A−4)で表されるモノマー(a2−1)を含む。
Si(R7)w(OR8)4-w …式(A−4)
Si(R13)x(OR14)4-x …式(A−8)
<感光性樹脂組成物>
複合樹脂(A)
条件(I):主鎖は、さらに、カルボン酸またはカルボン酸無水物を含む不飽和モノマー(a1−1)から誘導された繰り返し単位を含み、カルボン酸またはカルボン酸無水物を含む不飽和モノマー(a1−1)は、カルボン酸基構造および不飽和結合を含むか、カルボン酸無水物基構造および不飽和結合を含む。
条件(II):シロキサン系モノマー(a2)は、下記の式(A−4)で表されるモノマー(a2−1)を含む。
カルボン酸またはカルボン酸無水物を含む不飽和モノマー(a1−1)
シロキサン(メタ)アクリレート系モノマー(a1−2)
他の不飽和モノマー(a1−3)
シロキサン系モノマー(a2)
Si(R7)w(OR8)4-w …式(A−4)
Si(R13)x(OR14)4-x …式(A−8)
複合樹脂(A)の作製方法
o−ナフトキノンジアジドスルホネート(B)
溶剤(C)
熱発生剤(D)
熱酸発生剤
熱塩基発生剤
添加剤(E)
<保護膜の製造方法>
スピンコーティング、キャストコーティング、またロールコーティングによって、上述した溶液状態の感光性樹脂組成物を保護したい素子(以下、基板と称す)の上に塗布し、塗膜を形成する。
特定のパターンを有するマスクを用いて、プリベーク塗膜に対して露光を行う。露光処理に使用される光は、例えば、g線、h線、i線等の紫外線(UV)光が好ましく、紫外線光を提供するために使用される装置は、(超)高圧水銀ランプまたはメタルハライドランプがであってもよい。
23±2℃の温度の現像液中で露光後のプリベーク塗膜を浸漬して、約15秒〜5分間現像することにより、露光後のプリベーク塗膜の不必要な部分を除去し、基板上に所望のパターンを有する保護膜の半完成品を形成する。現像液は、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素カリウム、ケイ酸ナトリウム、メチルケイ酸ナトリウム(sodium methylsilicate)、アンモニア水、エチルアミン、ジエチルアミン、ジメチルエタノールアミン、水酸化テトラメチルアンモニウム(THAM)、水酸化テトラエチルアンモニウム、コリン、ピロール、ピペリジン、または1,8−ジアザ−ビシクロ−(5,4,0)−7−ウンデカン等のアルカリ化合物であってもよい。
基板(基板上に所定のパターンを有する保護膜の半完成品)を水で洗浄して、露光後のプリベーク塗膜の不必要な部分を除去する。そして、圧縮空気または圧縮窒素を用いて所定のパターンを有する保護膜の半完成品を乾燥させる。最後に、加熱板またはオーブン等の加熱装置により所定のパターンを有する保護膜の半完成品をポストベークする。加熱温度は、100℃〜250℃の温度に設定される。加熱板を使用する場合の加熱時間は、1分〜60分間であり、オーブンを使用する場合の加熱時間は、5分〜90分間である。それにより、所定のパターンを有する保護膜の半完成品が硬化されて、保護膜が形成される。
<液晶表示素子の製造方法>
<実施例>
複合樹脂(A)の合成例
感光性樹脂組成物の例
実施例1
実施例2〜実施例14
比較例1〜比較例5
(a)透明性
◎:95%≦透過率
○:90%≦透過率<95%
△:85%≦透過率<90%
×:透過率≦85%
(b)耐化学性
膜厚の変化率=〔(浸漬前の膜厚−浸漬後の膜厚)/浸漬前の膜厚〕×100%
◎:膜厚の変化率≦3%
○:3%<膜厚の変化率≦5%
△:5%<膜厚の変化率≦6%
×:6%<膜厚の変化率
<評価結果>
Claims (9)
- 複合樹脂(A)と、
o−ナフトキノンジアジドスルホネート(B)と、
溶剤(C)と、
を含み、前記複合樹脂(A)が、主鎖および側鎖を含み、前記主鎖が、シロキサン(メタ)アクリレート系モノマー(a1−2)から誘導された繰り返し単位を含み、前記側鎖が、シロキサン系モノマー(a2)から誘導された繰り返し単位を含み、且つ前記シロキサン(メタ)アクリレート系モノマー(a1−2)から誘導された繰り返し単位に結合され、前記複合樹脂(A)が、下記の条件(II)を満たし、
条件(II):前記シロキサン系モノマー(a2)は、下記の式(A−4)で表されるモノマー(a2−1)を含む、
Si(R7)w(OR8)4-w …式(A−4)
式(A−4)において、R7が、下記の式(A−5)、式(A−6)、または式(A−7)で表される構造、あるいは炭素数1〜10の炭化水素基、非置換のフェニル基、または一部の水素原子がハロゲンまたは炭素数1〜10の炭化水素基で置換されたフェニル基を示し、少なくとも1つのR7が、前記下記の式(A−5)で表される構造を示し、R8が、水素原子、炭素数1〜6の炭化水素基、炭素数1〜6のアシル基、または炭素数6〜15のアリール基を示し、式(A−4)において2個以上のR7またはR8がある時、各R7またはR8が、同じであっても、異なっていてもよく、wが、1〜3の整数を示し、
式(A−5)において、R9が、炭素数1〜10の炭化水素基を示し、mが、0または1であり、*が、結合部位を示し、
式(A−6)において、R10が、単結合、炭素数1〜10のアルキル基、または炭素数1〜10のアルコキシ基を示し、R11が、水素原子または炭素数1〜10の炭化水素基を示し、nが、0または1であり、*が、結合部位を示し、
式(A−7)において、R12が、単結合または炭素数1〜6のアルキレン基を示し、*が、結合部位を示す感光性樹脂組成物。 - 前記主鎖が、さらに、他の不飽和モノマー(a1−3)から誘導された繰り返し単位を含む請求項1に記載の感光性樹脂組成物。
- 前記シロキサン(メタ)アクリレート系モノマー(a1−2)が、下記の式(A−1)の構造を含有し、
式(A−1)において、R1が、水素原子またはメチル基を示し、aが、1〜6の整数を示し、R2が、それぞれ独立して、炭素数1〜12のアルキル基、フェニル基、炭素数1〜6のアルコキシ基、または下記の式(A−2)で表される基を示し、bが、1〜150の整数を示し、R3が、炭素数1〜6のアルキル基または下記の式(A−3)で表される基を示し、前記主鎖において、前記式(A−1)から誘導された複数の繰り返し単位がある時、前記式(A−1)から誘導された各繰り返し単位が、同じであっても、異なっていてもよく、
…式(A−2)
式(A−2)において、R4およびR5が、それぞれ独立して、炭素数1〜12のアルキル基またはフェニル基を示し、cが、2〜13の整数を示し、
式(A−3)において、R6が、それぞれ独立して、炭素数1〜12のアルキル基またはフェニル基を示す請求項1に記載の感光性樹脂組成物。 - 前記シロキサン系モノマー(a2)が、さらに、下記の式(A−8)で表されるモノマー(a2−2)を含み、
Si(R13)x(OR14)4-x …式(A−8)
式(A−8)において、R13が、炭素数1〜10の炭化水素基、非置換のフェニル基、または一部の水素原子がハロゲンまたは炭素数1〜10の炭化水素基で置換されたフェニル基を示し、R14が、水素原子、炭素数1〜6の炭化水素基、炭素数1〜6のアシル基、または炭素数6〜15のアリール基を示し、前記式(A−8)において2個以上のR13またはR14がある時、各R13またはR14が、同じであっても、異なっていてもよく、xが、0〜3の整数を示す請求項1に記載の感光性樹脂組成物。 - 前記複合樹脂(A)100重量部に対し、前記o−ナフトキノンジアジドスルホネート(B)の使用量が、1重量部〜30重量部であり、前記溶剤(C)の使用量が、100重量部〜1600重量部である請求項1に記載の感光性樹脂組成物。
- 熱酸発生剤または熱塩基発生剤(D)をさらに含む請求項1に記載の感光性樹脂組成物。
- 前記複合樹脂(A)100重量部に対し、前記熱酸発生剤または熱塩基発生剤(D)の使用量が、0.5重量部〜6重量部である請求項6に記載の感光性樹脂組成物。
- 請求項1〜7のいずれか一項に記載の前記感光性樹脂組成物により形成された保護膜。
- 請求項8に記載の前記保護膜を含む液晶表示素子。
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JP5115205B2 (ja) * | 2008-01-15 | 2013-01-09 | Jnc株式会社 | ポジ型感光性重合体組成物 |
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CN102443265B (zh) * | 2010-10-09 | 2013-06-05 | 奇美实业股份有限公司 | 光硬化性聚硅氧烷组成物及其所形成的基材保护膜 |
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