JP6357485B2 - 活性エネルギー線硬化型樹脂組成物、及びそれを用いた表示素子用スペーサー及び/またはカラーフィルター保護膜 - Google Patents
活性エネルギー線硬化型樹脂組成物、及びそれを用いた表示素子用スペーサー及び/またはカラーフィルター保護膜 Download PDFInfo
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- JP6357485B2 JP6357485B2 JP2015550957A JP2015550957A JP6357485B2 JP 6357485 B2 JP6357485 B2 JP 6357485B2 JP 2015550957 A JP2015550957 A JP 2015550957A JP 2015550957 A JP2015550957 A JP 2015550957A JP 6357485 B2 JP6357485 B2 JP 6357485B2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- DNWBGZGLCKETOT-UHFFFAOYSA-N cyclohexane;1,3-dioxane Chemical compound C1CCCCC1.C1COCOC1 DNWBGZGLCKETOT-UHFFFAOYSA-N 0.000 description 1
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
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- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- IZRVEUZYBVGCFC-UHFFFAOYSA-N ethyl 2-hydroxyisovalerate Chemical compound CCOC(=O)C(O)C(C)C IZRVEUZYBVGCFC-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- LJUJMKJGPIXNAK-UHFFFAOYSA-N ethyl 4-[2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-bis(4-ethoxycarbonylphenyl)imidazol-2-yl]-5-(4-ethoxycarbonylphenyl)imidazol-4-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=NC(N2C(=C(N=C2C=2C(=CC=CC=2)Cl)C=2C=CC(=CC=2)C(=O)OCC)C=2C=CC(=CC=2)C(=O)OCC)(C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(C(=O)OCC)C=C1 LJUJMKJGPIXNAK-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
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- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
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- XZUHEZIGAZNGJR-UHFFFAOYSA-N phenol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC1=CC=CC=C1.OC1=CC=CC=C1 XZUHEZIGAZNGJR-UHFFFAOYSA-N 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- NJFUXFRJVIXVSG-UHFFFAOYSA-M tetramethylphosphanium;chloride Chemical compound [Cl-].C[P+](C)(C)C NJFUXFRJVIXVSG-UHFFFAOYSA-M 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1466—Acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D131/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Coating compositions based on derivatives of such polymers
- C09D131/06—Homopolymers or copolymers of esters of polycarboxylic acids
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
- G02F1/133519—Overcoatings
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
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Description
特許文献4では、不飽和基含有ポリカルボン酸を含有する樹脂組成物がソルダーレジストに適していることが開示されているが、表示素子用スペーサーやカラーフィルター保護膜については全く記載がされていない。
(1)反応性ポリカルボン酸化合物(A)、反応性ポリカルボン酸化合物(A)以外の反応性化合物(B)、光重合開始剤(C)及び有機溶剤(D)を含有する表示素子用スペーサーまたはカラーフィルター保護膜用活性エネルギー線硬化型樹脂組成物であって、反応性ポリカルボン酸化合物(A)が、一般式(1)で示されるエポキシ樹脂(a)と一分子中に1個以上の重合可能なエチレン性不飽和基と1個以上のカルボキシル基を有する化合物(b)、及び必要に応じて一分子中に少なくとも2個以上の水酸基と一個以上のカルボキシル基を有する化合物(c)との反応物(E)に、更に多塩基酸無水物(d)を反応させて得られる反応性ポリカルボン酸化合物(A)である、該活性エネルギー線硬化型樹脂組成物に関する。
(2)さらに本発明は、反応性ポリカルボン酸化合物(A)が、一般式(1)で示されるエポキシ樹脂(a)と一分子中に1個以上の重合可能なエチレン性不飽和基と1個以上のカルボキシル基を有する化合物(b)、及び一分子中に少なくとも2個以上の水酸基と一個以上のカルボキシル基を有する化合物(c)との反応物(E)に、更に多塩基酸無水物(d)を反応させて得られる反応性ポリカルボン酸化合物(A)である、前記(1)に記載の表示素子用スペーサーまたはカラーフィルター保護膜用活性エネルギー線硬化型樹脂組成物に関する。
(3)さらに本発明は、前記(1)又は(2)に記載の活性エネルギー線硬化型樹脂組成物から形成される表示素子用スペーサーに関する。
(4)さらに本発明は、前記(1)又は(2)に記載の活性エネルギー線硬化型樹脂組成物から形成されるカラーフィルター保護膜に関する。
本発明における反応性ポリカルボン酸化合物(A)は、一般式(1)で示されるエポキシ樹脂(a)と一分子中に1個以上の重合可能なエチレン性不飽和基と1個以上のカルボキシル基を有する化合物(b)、及び必要に応じて一分子中に少なくとも2個以上の水酸基と一個以上のカルボキシル基を有する化合物(c)との反応物(E)に、更に多塩基酸無水物(d)を反応させて得られる。
本発明においては、エポキシカルボキシレート化反応により、分子鎖中にエチレン性不飽和基と水酸基を導入することで、本発明の特徴が発揮されるものである。
また、本発明において用いられるエポキシ樹脂(a)は常温で固体のものがより好ましい。本発明においては通常、軟化点が50〜100℃、もしくは融点が50〜190℃であるエポキシ樹脂(a)が使用されるが、軟化点が60〜100℃、もしくは融点が60〜190℃のものが好ましい。また、エポキシ当量が130〜500g/eq.のものが本発明においては通常用いられ得るが、好ましくは150〜400g/eq.、さらに好ましくは170〜300g/eq.である。エポキシ当量が小さすぎると硬く、もろくなりやすい傾向が強く、エポキシ当量が大きすぎる場合、硬度が出にくい、ガラス転移点が低くなることがある。
1.エポキシ当量が好ましくは195〜245g/eq.、より好ましくは200〜240g/eq.である。
2.ゲルパーミエーションクロマトグラフィーにおいて、フェノール化合物(PA1)同士がエピハロヒドリンによって2つ繋がったものが30面積%以下、3つ繋がったものが20面積%以下、より好ましくは2つ繋がったものが25面積%以下、3つ繋がったものが15面積%以下である。残余としてはエポキシ樹脂(a)の単量体が該当する。
一分子中に一個のカルボキシル基を有するモノカルボン酸化合物としては、例えば(メタ)アクリル酸類やクロトン酸、α−シアノ桂皮酸、桂皮酸、或いは飽和または不飽和二塩基酸と不飽和基含有モノグリシジル化合物との反応物が挙げられる。上記において(メタ)アクリル酸類としては、例えば(メタ)アクリル酸、β−スチリルアクリル酸、β−フルフリルアクリル酸、(メタ)アクリル酸二量体、飽和または不飽和二塩基酸無水物と1分子中に1個の水酸基を有する(メタ)アクリレート誘導体と当モル反応物である半エステル類、飽和または不飽和二塩基酸とモノグリシジル(メタ)アクリレート誘導体類との当モル反応物である半エステル類等が挙げられる。
これらのうち最も好ましくは、活性エネルギー線硬化型樹脂組成物としたときの感度の点で(メタ)アクリル酸、(メタ)アクリル酸とε−カプロラクトンとの反応生成物または桂皮酸が挙げられる。化合物(b)としては、化合物中に水酸基を有さないものが好ましい。
本発明における一分子中に少なくとも2個以上の水酸基と一個以上のカルボキシル基を有する化合物(c)の具体例としては、例えば、ジメチロールプロピオン酸、ジメチロールブタン酸、ジメチロール酢酸、ジメチロール酪酸、ジメチロール吉草酸、ジメチロールカプロン酸等のポリヒドロキシ含有モノカルボン酸類等を挙げることができる。特に好ましいものとしては、例えばジメチロールプロピオン酸等が挙げられる。
この反応におけるエポキシ樹脂(a)と化合物(b)および必要に応じて用いられる化合物(c)のカルボン酸総計の仕込み割合としては、用途に応じて適宜変更されるべきものである。即ち、全てのエポキシ基をカルボキシレート化した場合は、未反応のエポキシ基が残存しないために、反応性エポキシカルボキシレート化合物としての保存安定性は高い。この場合は、導入した二重結合による反応性のみを利用することになる。
反応性ポリカルボン酸化合物(A)の当該樹脂組成物中における使用割合は、通常5〜69重量%、好ましくは8〜59重量%程度である。
(1)水酸基を有する単量体(e)に対し、エチレン性二重結合を有する酸無水物(f)、
(2)水酸基を有する単量体(e)に対し、イソシアネート基とエチレン性二重結合を有する化合物(f)、
(3)水酸基を有する単量体(e)に対し、塩化アシル基とエチレン性二重結合を有する化合物(f)、
(4)エチレン性二重結合を有する酸無水物(e)に対し、水酸基とエチレン性二重結合を有する化合物(f)、
(5)カルボキシル基を有する単量体(e)に対し、エポキシ基とエチレン性二重結合を有する化合物(f)、
(6)エポキシ基を有する単量体(e)に対し、カルボキシル基とエチレン性二重結合を有する化合物(f)。
当該組成物から形成される表示素子用スペーサーは、本発明に好適に含まれる。当該表示素子用スペーサーの形成方法は、
(1)当該組成物を、基板上に塗布して塗膜を形成する工程、
(2)上記塗膜の少なくとも一部に放射線を照射する工程、
(3)上記放射線が照射された塗膜を現像する工程、及び
(4)上記現像された塗膜を加熱する工程
当該形成方法において形成されたスペーサーは、塗布ムラがなく高度な平坦性を有し、柔軟で塑性変形の小さなスペーサーである。液晶表示素子、有機EL表示素子等の表示素子に好適に使用できる。
1)エポキシ当量:JISK7236:2001に準じた方法で測定した。
2)軟化点:JISK7234:1986に準じた方法で測定した。
3)酸価:JISK0070:1992に準じた方法で測定した
[反応性ポリカルボン酸化合物(A)の調製]
エポキシ樹脂(a)としてNC−6300H(日本化薬製;一般式(1)のn=0(64%),n=1(23%),n=2以上(13%);エポキシ当量230g/eq)を表1中記載量、化合物(b)としてアクリル酸(略称AA、Mw=72)を表1中記載量、化合物(c)としてジメチロールプロピオン酸(略称DMPA、Mw=134)を表1中記載量加えた。触媒としてトリフェニルフォスフィン3g、溶剤としてプロピレングリコールモノメチルエーテルモノアセテートを固形分が反応液の80重量%となるように加え、100℃で24時間反応させ、反応性エポキシカルボキシレート化合物(E)溶液を得た。固形分酸価(AV:mgKOH/g)5以下を反応終点とし、次反応に進んだ。酸価測定は、反応溶液にて測定し固形分としての酸価に換算した。
次いで、反応性エポキシカルボキシレート化合物(E)溶液に多塩基酸無水物(d)として、テトラヒドロ無水フタル酸(略称THPA)を表1記載量、及び溶剤として固形分100重量部に対して65重量部となるようプロピレングリコールモノメチルエーテルモノアセテートを添加、100℃に加熱した後、酸付加反応させ反応性ポリカルボン酸化合物(A)溶液を得た。固形分酸価(AV:mgKOH/g)を表1中に記載した。
[比較用反応性ポリカルボン酸化合物の調製]
クレゾールノボラック型エポキシ樹脂EOCN−103S(日本化薬製、エポキシ当量200g/eq)を表1中記載量、化合物(b)としてアクリル酸を表1中記載量、化合物(c)としてジメチロールプロピオン酸(略称DMPA、Mw=134)を表1中記載量加えた。触媒としてトリフェニルフォスフィン3g、溶剤としてプロピレングリコールモノメチルエーテルモノアセテートを固形分が反応液の80重量%となるように加え、100℃で24時間反応させ、カルボキシレート化合物溶液を得た。固形分酸価(AV:mgKOH/g)5mgKOH/g以下を反応終点とし、次反応に進んだ。
次いで、反応性エポキシカルボキシレート化合物溶液に多塩基酸無水物として、テトラヒドロ無水フタル酸(略称THPA)を表1記載量、及び溶剤として固形分100重量部に対して65重量部となるようプロピレングリコールモノメチルエーテルモノアセテートを添加、100℃に加熱した後、酸付加反応させ比較用反応性ポリカルボン酸化合物溶液を得た。固形分酸価(AV:mgKOH/g)を表1中に記載した。
[比較用反応性カプロラクトン変性ポリカルボン酸化合物の調製]
クレゾールノボラック型エポキシ樹脂EOCN−103S(日本化薬製、エポキシ当量200g/eq)を200g、アクリル酸を58g、ジメチロールプロピオン酸を40g、触媒としてトリフェニルフォスフィン3g、溶剤としてプロピレングリコールモノメチルエーテルモノアセテートを固形分が反応液の80重量%となるように加え、100℃で24時間反応させた。さらに、ε−カプロラクトンを68g添加し、8時間反応させた。次いで、多塩基酸無水物として、テトラヒドロ無水フタル酸(略称THPA)を91g、及び溶剤として固形分100重量部に対して65重量部となるようプロピレングリコールモノメチルエーテルモノアセテートを添加、100℃に加熱した後、酸付加反応させ比較用反応性カプロラクトン変性ポリカルボン酸化合物溶液を得た。固形分酸価(AV:mgKOH/g)は、70mgKOH/gであった。
また、実施例及び比較例で用いた各成分の詳細を以下に示す。
<反応性化合物(B)>
B−1:ジペンタエリスリトールヘキサアクリレートとジペンタエリスリトールペンタアクリレートとの混合物(KAYARAD DPHA、日本化薬製)
<光重合開始剤(C)>
C−1:エタノン−1−〔9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル〕−1−(O−アセチルオキシム)(イルガキュアOXE02、BASF社製)
<有機溶剤(D)>
PGMEA:プロピレングリコールモノメチルエーテルアセテート
DEGDM:ジエチレングリコールジメチルエーテル
<界面活性剤(H)>
H−1:シリコーン系界面活性剤(東レ・ダウコーニング・シリコーン社製、SH8400FLUID)
実施例2−1
反応性ポリカルボン酸化合物(A)として、実施例1−1で得られた反応物 100重量部(固形分)に相当する量を含む溶液に、反応性化合物(B)として(B−1)100重量部、光重合開始剤(C)として(C−1)10重量部、有機溶剤としてPGMEA、DEGDMを所望の固形分濃度となるように添加し、界面活性剤(H)として(H−1)0.3重量部を混合し、孔径0.2μmのメンブランフィルタで濾過することにより、当該組成物(S−1)を調製した。なお、表2中の有機溶剤の数値は、PGMEAとDEGDMの質量比である。
各成分の種類及び配合量を表2に記載の通りとした以外は、実施例2−1と同様に操作して実施例2−2〜2−3及び比較例2−1〜2−3の組成物を調製した。なお、表2中の有機溶剤の数値は、PGMEAとDEGDMの質量比である。
実施例2−1〜2−3及び比較例2−1〜2−3の組成物、及びその塗膜から形成されるスペーサーについて下記の評価をした。評価結果を表3にあわせて示す。
E型粘度計(東機産業(株)製、TV−200)を用いて、25℃における各組成物の粘度(mPa・s)を測定した。
当該組成物0.3gをアルミ皿に精坪し、ジエチレングリコールジメチルエーテル約1gを加えたのち、175℃で60分間ホットプレート上にて乾固させて、乾燥前後の重量から当該組成物中の固形分濃度(質量%)を求めた。
100×100mmのクロム成膜ガラス上に、当該組成物をスリットダイコーター((株)テクノマシーン製、理化ダイ)を用いて塗布し0.5Torrまで減圧乾燥した後、ホットプレート上で100℃にて2分間プレベークして塗膜を形成し、さらに200mJ/cm2の露光量で露光することにより、クロム成膜ガラスの上面からの膜厚が4μmの膜を形成した。ナトリウムランプ下において、肉眼によりこの塗膜の外観の観察を行った。このとき、塗膜の全体における筋ムラ(塗布方向又はそれに交差する方向にできる一本または複数本の直線のムラ)、モヤムラ(雲状のムラ)、ピン跡ムラ(基板支持ピン上にできる点状のムラ)の出現状況を調べた。これらのムラのいずれもほとんど見えない場合を「○(良好)」、いずれかが少し見える場合を「△(やや不良)」、はっきりと見える場合を「×(不良)」と判断した。
上述のようにして作製したクロム成膜ガラス上の塗膜の膜厚を、針接触式測定機(東京精密(株)製、サーフコム)を用いて測定した。膜厚均一性は、9つの測定点における膜厚を測定し、下記式から計算した。9つの測定点は基板の短軸方向をX、長軸方向をYとすると、(X[mm]、Y[mm])が、(50、10)、(50、20)、(50、30)、(50、40)、(50、50)、(50、60)、(50、70)、(50、80)、(50、90)である。膜厚均一性が2%以下の場合は、膜厚均一性は良好と判断できる。
100mm×100mmの無アルカリガラス基板上にスリットコーターを用いて塗布し塗布条件として、下地とノズルの距離150μm、露光後の膜厚が2.5μmとなるように、ノズルから塗布液を吐出し、ノズルの移動速度を120mm/sec.〜200mm/sec.の範囲で変量し、液切れによる筋状のムラが発生しない最大速度を求めた。この時、180mm/sec.以上の速度でも筋状のムラが発生しない場合は、高速塗布に対応が可能であると判断できる。
100mm×100mmのITOスパッタしたガラス基板上にスピンコート法を用いて、当該組成物を塗布したのち、90℃のホットプレート上で3分間プレベークすることにより、膜厚3.5μmの塗膜を形成した。次いで、得られた塗膜に、開口部として直径12μmの円状パターンが形成されたフォトマスクを介して、紫外線露光装置((株)オーク製作所、型式HMW−680GW)を用いて露光した。その後、0.05質量%水酸化カリウム水溶液により25℃にて60秒間現像したのち、純水で1分間洗浄し、さらに230℃のオーブン中で30分間ポストベークすることにより、パターン状被膜からなるスペーサーを形成した。このとき、ポストベーク後の残膜率(ポストベーク後の被膜の膜厚×100/露光後(ポストベーク前)膜厚)が90%以上となる最小の露光量を調べ、この値を感度とした。この値が55mJ/cm2以下であった場合、感度は良好であるといえる。
(現像残渣)
また、基板上表面を目視により観察し、残留物の有無を確認した。評価基準は以下の通り。
○…残留物なし。
△…残留物わずかにあり。
×…残留物が多い
露光量を上記放射線感度の評価で決定した感度に相当する露光量とした以外は、放射線感度の評価と同様に操作して基板上に円柱状パターンからなるスペーサーを形成した。その際、ポストベーク後のパターン底部の直径が20μmとなるように、露光時に介するフォトマスクの直径を変更した。このスペーサーにつき、微小圧縮試験機(フィッシャースコープH100C、フィッシャーインストルメンツ(株)製)を用い、50μm角状の平面圧子を使用し、50mNの荷重にて圧縮試験を行い、荷重に対する圧縮変位量の変化を測定し、50mNの荷重時の変位量と50mNの荷重を取り除いた時の変位量から回復率(%)を算出した。このとき、回復率が70%以上であり、かつ50mNの荷重時の変位が0.15μm以上であった場合、高い回復率及び柔軟性の双方を具備した圧縮性能を有するスペーサーであるといえる。
50mm×50mmの無アルカリガラス基板上にスピンコーターを用いて塗布し、0.5Torrまで減圧乾燥した後、ホットプレート上で100℃にて2分間プレベークして塗膜を形成し、さらに200mJ/cm2の露光量で露光することにより、膜厚が4μmの膜を形成した。上記硬化塗膜を有する評価基板をヘイズメーター(日本電色工業(株)製、TC−H3DPK)を使用し測定した。
上記硬化塗膜を有する評価基板を250℃×1hr熱処理し、400nm、540nmの波長光の透過率を分光光度計(日立製作所(株)製、U−3310)を使用して測定した。
なお、本出願は、2013年11月28日付で出願された日本国特許出願(特願2013−246535)に基づいており、その全体が引用により援用される。また、ここに引用されるすべての参照は全体として取り込まれる。
Claims (4)
- 反応性ポリカルボン酸化合物(A)、反応性ポリカルボン酸化合物(A)以外の反応性化合物(B)、光重合開始剤(C)及び有機溶剤(D)を含有する表示素子用スペーサーまたはカラーフィルター保護膜用活性エネルギー線硬化型樹脂組成物であって、
反応性ポリカルボン酸化合物(A)が、一般式(1)で示されるエポキシ樹脂(a)と一分子中に1個以上の重合可能なエチレン性不飽和基と1個以上のカルボキシル基を有する化合物(b)、及び必要に応じて一分子中に少なくとも2個以上の水酸基と一個以上のカルボキシル基を有する化合物(c)との反応物(E)に、更に多塩基酸無水物(d)を反応させて得られる反応性ポリカルボン酸化合物(A)である、該活性エネルギー線硬化型樹脂組成物。
- 反応性ポリカルボン酸化合物(A)が、一般式(1)で示されるエポキシ樹脂(a)と一分子中に1個以上の重合可能なエチレン性不飽和基と1個以上のカルボキシル基を有する化合物(b)、及び一分子中に少なくとも2個以上の水酸基と一個以上のカルボキシル基を有する化合物(c)との反応物(E)に、更に多塩基酸無水物(d)を反応させて得られる反応性ポリカルボン酸化合物(A)である、請求項1に記載の表示素子用スペーサーまたはカラーフィルター保護膜用活性エネルギー線硬化型樹脂組成物。
- 請求項1又は2に記載の活性エネルギー線硬化型樹脂組成物から形成される表示素子用スペーサー。
- 請求項1又は2に記載の活性エネルギー線硬化型樹脂組成物から形成されるカラーフィルター保護膜。
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