JP2018063433A - 感光性着色樹脂組成物 - Google Patents
感光性着色樹脂組成物 Download PDFInfo
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- JP2018063433A JP2018063433A JP2017217277A JP2017217277A JP2018063433A JP 2018063433 A JP2018063433 A JP 2018063433A JP 2017217277 A JP2017217277 A JP 2017217277A JP 2017217277 A JP2017217277 A JP 2017217277A JP 2018063433 A JP2018063433 A JP 2018063433A
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- Prior art keywords
- compound
- photosensitive
- colored resin
- film
- resin composition
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 146
- 238000004040 coloring Methods 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 302
- 229920005989 resin Polymers 0.000 claims abstract description 166
- 239000011347 resin Substances 0.000 claims abstract description 166
- 238000010521 absorption reaction Methods 0.000 claims abstract description 71
- 239000010408 film Substances 0.000 claims description 246
- -1 4-naphthoquinonediazide sulfonyl ester compound Chemical class 0.000 claims description 194
- 238000000034 method Methods 0.000 claims description 53
- 239000000975 dye Substances 0.000 claims description 51
- 239000000178 monomer Substances 0.000 claims description 50
- 239000000758 substrate Substances 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 229920001721 polyimide Polymers 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 29
- 239000011248 coating agent Substances 0.000 claims description 28
- 239000004642 Polyimide Substances 0.000 claims description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000002243 precursor Substances 0.000 claims description 23
- 125000000962 organic group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 18
- 229920002577 polybenzoxazole Polymers 0.000 claims description 16
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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- 125000000542 sulfonic acid group Chemical group 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 8
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- 230000008569 process Effects 0.000 claims description 4
- 239000001045 blue dye Substances 0.000 claims description 2
- 239000001046 green dye Substances 0.000 claims description 2
- 239000001048 orange dye Substances 0.000 claims description 2
- 239000001047 purple dye Substances 0.000 claims description 2
- 239000001044 red dye Substances 0.000 claims description 2
- 239000001043 yellow dye Substances 0.000 claims description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000036211 photosensitivity Effects 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 121
- 238000005192 partition Methods 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000002834 transmittance Methods 0.000 description 109
- 239000002966 varnish Substances 0.000 description 104
- 230000015572 biosynthetic process Effects 0.000 description 69
- 238000003786 synthesis reaction Methods 0.000 description 65
- 238000012545 processing Methods 0.000 description 50
- 239000003999 initiator Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- 230000000052 comparative effect Effects 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- 239000002253 acid Substances 0.000 description 34
- 239000000126 substance Substances 0.000 description 32
- WLTSXAIICPDFKI-FNORWQNLSA-N (E)-3-dodecene Chemical compound CCCCCCCC\C=C\CC WLTSXAIICPDFKI-FNORWQNLSA-N 0.000 description 29
- 239000010410 layer Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000049 pigment Substances 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 19
- 238000011161 development Methods 0.000 description 19
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 238000001723 curing Methods 0.000 description 17
- 230000006866 deterioration Effects 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 16
- 239000012860 organic pigment Substances 0.000 description 16
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 239000003513 alkali Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 150000001282 organosilanes Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000003431 cross linking reagent Substances 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000004849 alkoxymethyl group Chemical group 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 229940116333 ethyl lactate Drugs 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- 230000007257 malfunction Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 239000012954 diazonium Substances 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 150000002923 oximes Chemical class 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 150000004714 phosphonium salts Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- 238000001914 filtration Methods 0.000 description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
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- 239000011159 matrix material Substances 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 229920005575 poly(amic acid) Polymers 0.000 description 6
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- 238000004528 spin coating Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 5
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 4
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- 238000004090 dissolution Methods 0.000 description 4
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 4
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- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
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Abstract
有機発光装置や表示素子に用いられる平坦化膜、絶縁層、隔壁形成に適した高感度かつ、可視光短波長領域を吸収する機能、また外光反射を抑制する機能を有する感光性着色樹脂組成物およびその耐熱性着色樹脂膜を提供することを課題とする。
【解決手段】
アルカリ可溶性樹脂(a)、感光性化合物(b)、波長400nm以上490nm未満の範囲に吸収極大を持つ化合物(c)とを含有し、前記感光性化合物(b)が感光性化合物(b1)を含み、前記感光性化合物(b1)が、波長350nm以上450nm以下の範囲における最大吸収波長を波長350nm以上390nm以下の範囲に有する感光性着色樹脂組成物。
【選択図】なし
Description
ポリイミド、ポリイミド前駆体、またはポリベンゾオキサゾール前駆体の中から選ばれるアルカリ可溶性樹脂またはそれらの共重合体は、一般式(1)または(2)で表される構造単位を5〜100,000有することが好ましい。また、一般式(1)または(2)で表される構造単位に加えて、他の構造単位を有してもよい。この場合、一般式(1)または(2)で表される構造単位を、主たる構成単位とすることが好ましい。ここで主たる構成単位とは全構造単位数のうち50モル%以上有することをいい、70モル%以上有することがより好ましい。
前記一般式(3)で表されるオルガノシランの具体例としては、テトラメトキシシラン、テトラエトキシシラン、テトラアセトキシシラン、テトラフェノキシシラン等の4官能性シラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリイソプロポキシシラン、メチルトリn−ブトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリイソプロポキシシラン、エチルトリn−ブトキシシラン、n−プロピルトリメトキシシラン、n−プロピルトリエトキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、n−ヘキシルトリメトキシシラン、n−ヘキシルトリエトキシシラン、デシルトリメトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、3−アクリロキシプロピルトリメトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、p−ヒドロキシフェニルトリメトキシシラン、1−(p−ヒドロキシフェニル)エチルトリメトキシシラン、2−(p−ヒドロキシフェニル)エチルトリメトキシシラン、4−ヒドロキシ−5−(p−ヒドロキシフェニルカルボニルオキシ)ペンチルトリメトキシシラン、トリフルオロメチルトリメトキシシラン、トリフルオロメチルトリエトキシシラン、3,3,3−トリフルオロプロピルトリメトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、〔(3−エチル−3−オキセタニル)メトキシ〕プロピルトリメトキシシラン、〔(3−エチル−3−オキセタニル)メトキシ〕プロピルトリエトキシシラン、3−メルカプトプロピルトリメトキシシラン、3−トリメトキシシリルプロピルコハク酸、1−ナフチルトリメトキシシラン、1−ナフチルトリエトキシシラン、1−ナフチルトリ−n−プロポキシシラン、2−ナフチルトリメトキシシラン、1−アントラセニルトリメトキシシラン、9−アントラセニルトリメトキシシラン、9−フェナントレニルトリメトキシシラン、9−フルオレニルトリメトキシシラン、2−フルオレニルトリメトキシシラン、1−ピレニルトリメトキシシラン、2−インデニルトリメトキシシラン、5−アセナフテニルトリメトキシシラン等の3官能性シラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジアセトキシシラン、ジn−ブチルジメトキシシラン、ジフェニルジメトキシシラン、(3−グリシドキシプロピル)メチルジメトキシシラン、(3−グリシドキシプロピル)メチルジエトキシシラン、ジ(1−ナフチル)ジメトキシシラン、ジ(1−ナフチル)ジエトキシシラン等の2官能性シラン、トリメチルメトキシシラン、トリn−ブチルエトキシシラン、(3−グリシドキシプロピル)ジメチルメトキシシラン、(3−グリシドキシプロピル)ジメチルエトキシシラン等の1官能性シランが挙げられる。これらのオルガノシランを2種以上用いてもよい。
前記一般式(4)で表されるオルガノシランの具体例としては、扶桑化学工業株式会社製メチルシリケート51(R17〜R20:メチル基、n:平均4)、多摩化学工業株式会社製Mシリケート51(R17〜R20:メチル基、n:平均3〜5)、シリケート40(R17〜R20:エチル基、n:平均4〜6)、シリケート45(R17〜R20:エチル基、n:平均6〜8)、コルコート株式会社製メチルシリケート51(R17〜R20:メチル基、n:平均4)、メチルシリケート53A(R17〜R20:メチル基、n:平均7)、エチルシリケート40(R17〜R20:エチル基、n:平均5)等が挙げられ、各社から入手できる。これらを2種以上用いてもよい。
チタノセン系光重合開始剤としては、例えば、ビス(η5−2,4−シクロペンタジエン−1−イル)−ビス[2,6−ジフルオロ)−3−(1H−ピロール−1−イル)フェニル]チタン(IV)又はビス(η5−3−メチル−2,4−シクロペンタジエン−1−イル)−ビス(2,6−ジフルオロフェニル)チタン(IV)が挙げられる。
前述の感光性着色樹脂組成物を、基板に塗布し、塗布膜を形成する塗布工程、
前記塗布膜を乾燥し感光性着色樹脂膜を形成する乾燥工程、
乾燥した感光性着色樹脂膜を露光する露光工程、
露光した感光性着色樹脂膜を現像する現像工程、および
現像した感光性着色樹脂膜を加熱処理する加熱処理工程、
を含む耐熱性着色樹脂膜の製造方法である。
実施例および比較例で調製した感光性着色樹脂組成物(以下、ワニスと記す場合もある。)を8インチシリコンウエハ上に現像後の膜厚が3.5μmとなるようにスピンコートし、次いで、ホットプレート(東京エレクトロン(株)製、塗布現像装置Act−8)を用いて、120℃で80秒間加熱乾燥(プリベーク)し、プリベーク膜を作製した。得られたプリベーク膜をghi線マスクアライナー(ユニオン光学(株)製、PEM−6M)を用いてそれぞれ0〜1000mJ/cm2の露光量にて20mJ/cm2ステップで露光した。露光に用いたライン&スペース(L&S)パターンは1、2、3、4、5、6、7、8、9、10、15、20、30、50、100μmである。露光後、2.38質量%のテトラメチルアンモニウム(TMAH)水溶液(多摩化学工業製)で所望の膜厚を得るべく30〜100秒間現像し、次いで純水でリンスし、レリーフパターンを得た。なお、プリベーク後および現像後の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM−602を使用し、屈折率を1.629として測定した。
5センチ角のガラス基板上にワニスを加熱処理(キュア)後の膜厚が1.5μmとなるようにスピンコートで塗布し、120℃で80秒間プリベークした。その後、光洋サーモシステム(株)製高温クリーンオーブンCLH−21CD(V)−Sを用いて、窒素雰囲気下250℃で60分間キュアし、耐熱性着色樹脂膜を作製した。なお、耐熱性着色樹脂膜の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM−602を使用し、ポリイミドを基準として屈折率1.629として測定した。このようにして得られた耐熱性着色樹脂膜について、紫外可視分光光度計MultiSpec−1500(島津製作所(株)製)を用いて、波長300nm〜800nmの透過スペクトルを測定した。400〜450nmの光透過率が60%より高いものは不十分として1、400〜450nmの光透過率が60%以下のものは良好として2、さらに400〜650nmの光透過率が60%以下のものは極めて良好として3、と評価した。また、キュア膜の膜厚が1.5μmでなかった場合には、膜厚を1.5μmとした場合の光透過率に換算した。
8インチシリコンウエハ上にワニスをキュア後10.0μmとなるようにスピンコートし、次いで、ホットプレート(東京エレクトロン(株)製、塗布現像装置Act−8)を用いて、120℃で80秒間プリベークし、プリベーク膜を作製した。その後、得られたプリベーク膜を光洋サーモシステム(株)製高温クリーンオーブンCLH−21CD(V)−Sを用いて、窒素雰囲気下250℃で60分間キュアし、耐熱性着色樹脂膜を作製した。なお、耐熱性着色樹脂膜の膜厚は、大日本スクリーン製造(株)製光干渉式膜厚測定装置ラムダエースSTM−602を使用し、屈折率1.629として測定した。このようにして得られた耐熱性着色樹脂膜について、フッ酸を用いてシリコンウエハから剥離し、剥離した耐熱性着色樹脂膜から10mg取り出して、熱重量測定装置TGA−50(島津製作所(株)製)を用いて70℃、20分での処理前後の質量減少量から吸水率の算出を行った。
以下の手順にて本実施例または比較例からなる平坦化膜を具備する酸化物TFT基板の作製を得た。
5センチ角のAgスパッタされたガラス基板上にワニスをキュア後の膜厚が1.5μmとなるようにスピンコートで塗布し、120℃で80秒間プリベークした。その後、光洋サーモシステム(株)製高温クリーンオーブンCLH−21CD(V)−Sを用いて、窒素雰囲気下250℃で60分間キュアし、耐熱性着色樹脂膜を作製した。このようにして得られたガラス基板について、分光測色計CM−2600d(コニカミノルタ(株)製)で反射率を測定した。
2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(セントラル硝子(株)製、以下、BAHFと記す場合もある。)18.3g(0.05モル)をアセトン100mL、プロピレンオキシド(東京化成(株)製)17.4g(0.3モル)に溶解させ、−15℃に冷却した。ここに3−ニトロベンゾイルクロリド(東京化成(株)製)20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、−15℃で4時間撹拌し、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、合成例1で得られたヒドロキシル基含有ジアミン15.1g(0.025モル)、2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(BAHF)3.66g(0.01モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン(以下、SiDAと記す場合もある。)0.62g(0.0025モル)をN−メチルピロリドン(以下、NMPと記す場合もある。)200gに溶解した。ここに2,2−ビス(3,4−ジカルボキシフェニル)ヘキサフルオロプロパン二無水物(以下、6FDAと記す場合もある。)22.2g(0.05モル)を加え、40℃で1時間撹拌した。その後、3−アミノフェノール(東京化成(株)製、以下、MAPと記す場合もある。)2.73g(0.025モル)を加え、40℃で1時間撹拌した。さらにジメチルホルアミドジメチルアセタール(三菱レーヨン(株)製、以下、DFAと記す場合もある。)11.9g(0.1モル)をNMP5gで希釈した溶液を10分かけて滴下した。滴下後、40℃で2時間撹拌を続けた。撹拌終了後、溶液を水2Lに投入して、ポリマー固体の沈殿を濾過で集めた。さらに水2Lで3回洗浄を行い、集めたポリマー固体を50℃の真空乾燥機で72時間乾燥し、ポリアミド酸エステル(A−1)を得た。
乾燥窒素気流下、2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(BAHF)29.30g(0.08モル)、SiDA1.24g(0.005モル)、末端封止剤として、3−アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここにビス(3,4−ジカルボキシフェニル)エーテル二無水物(マナック(株)製、以下、ODPAと記す場合もある。)31.2g(0.1モル)をNMP20gとともに加えて、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥しアルカリ可溶性ポリイミド樹脂(A−2)の粉末を得た。
乾燥窒素気流下、m−クレゾール70.2g(0.65モル)、p−クレゾール37.8g(0.35モル)、37質量%、ホルムアルデヒド水溶液75.5g(ホルムアルデヒド0.93モル)、シュウ酸二水和物0.63g(0.005モル)、メチルイソブチルケトン264gをフラスコに仕込んだ後、油浴中に浸し、反応液を還流させながら、4時間重縮合反応を行った。その後、油浴の温度を3時間かけて昇温し、その後に、フラスコ内の圧力を40〜67hPaまで減圧して揮発分を除去し、室温まで冷却してフェノール樹脂(A−3)のポリマー固体を得た。
乾燥窒素気流下、テトラヒドロフラン500ml、開始剤としてsec−ブチルリチウム0.01モルを加えた混合溶液に、p−t−ブトキシスチレンとスチレンをモル比3:1の割合で合計20gを添加し、3時間撹拌しながら重合させた。重合停止反応は反応溶液にメタノール0.1モルを添加して行った。次にポリマーを精製するために反応混合物をメタノール中に注ぎ、沈降した重合体を乾燥させて白色重合体を得た。更に、白色重合体をアセトン400mlに溶解し、60℃で少量の濃塩酸を加えて7時間撹拌後、水に注ぎ、ポリマーを沈澱させ、p−t−ブトキシスチレンを脱保護してヒドロキシスチレンに変換し、洗浄乾燥することで、精製されたp−ヒドロキシスチレンとスチレンの共重合体(A−4)を得た。
乾燥窒素気流下、500mlの三口フラスコにメチルトリメトキシシランを54.48g(0.40モル)、フェニルトリメトキシシランを99.15g(0.50モル)、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランを12.32g(0.05モル)、Mシリケート51(多摩化学工業株式会社製)を5.88g(Si原子モル数0.05モル相当)、プロピレングリコールモノメチルエーテルアセテート(以下PGMEAと記す場合もある。)を155.04g仕込み、室温で撹拌しながら水54.45gにリン酸0.515g(仕込みモノマーに対して0.30質量部)を溶かしたリン酸水溶液を10分間かけて添加した。その後、フラスコを40℃のオイルバスに浸けて60分間撹拌した後、オイルバスを30分間かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱撹拌し(内温は100℃)、シロキサンポリマー溶液(A−5)を得た。
乾燥窒素気流下、プロトン性極性基を有する環状オレフィン単量体として8−ヒドロキシカルボニルテトラシクロ[4.4.0.12,5.17,10]ドデカ−3−エン120g(0.62モル)、プロトン性極性基を有さない環状オレフィン単量体としてN−フェニル−(5−ノルボルネン−2,3−ジカルボキシイミド)80g(0.45モル)、極性基を有さない環状オレフィン単量体として1,5−ヘキサジエン5.6g(0.07モル)、(1,3−ジメシチルイミダゾリジン−2−イリデン)(トリシクロヘキシルホスフィン)ベンジリデンルテニウムジクロリド0.1g及びPGMEA800gを、窒素置換した耐圧ガラス反応器に仕込み、撹拌下に80℃で2時間重合反応を行って開環メタセシス重合体を含有する重合反応溶液を得た。
乾燥窒素気流下、還流冷却器付き四つ口フラスコ中にビスフェノールフルオレン型エポキシ樹脂とアクリル酸との等当量反応物(新日鐵化学社製、製品名「ASF−400」溶液)の50%PGMEA溶液198.53gと、ベンゾフェノンテトラカルボン酸二無水物39.54g(0.12モル)、コハク酸無水物8.13g(0.08モル)、PGMEA48.12g及びトリフェニルホスフィン0.45gを仕込み、120〜125℃に加熱下に1時間撹拌し、更に75〜80℃で6時間の加熱撹拌を行い、その後、グリシジルメタクリレート8.6gを投入し、更に80℃で8時間攪拌し、カルド樹脂(A−7)を得た。
乾燥窒素気流下、4,4’−[1−[4−[1−(4−ヒドロキシフェニル−1)−1−メチルエチル]フェニル]エチリデン]ビスフェノール(本州化学工業(株)製、以下TrisP−PAと記す場合もある。)、42.4g(0.1モル)と4−ナフトキノンジアジドスルホン酸クロリド(東洋合成(株)製、NAC−4)72.3g(0.27モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン100gと混合したトリエチルアミン25.0gを、系内が35℃以上にならないように滴下した。滴下後、40℃で2時間撹拌した。トリエチルアミン塩を濾過し、濾液を水に投入した。その後、析出した沈殿を濾過で集め、さらに1%塩酸水1Lで洗浄した。その後、さらに水2Lで2回洗浄した。この沈殿を真空乾燥機で乾燥し、下記式で表されるキノンジアジド化合物(B−1)(波長350nm以上450nm以下の範囲における最大吸収波長:380nm)を得た。
乾燥窒素気流下、4,4’−[1−[4−[1−(4−ヒドロキシフェニル−1)−1−メチルエチル]フェニル]エチリデン]ビスフェノール(本州化学工業(株)製、以下TrisP−PAとする)、42.4g(0.1モル)と5−ナフトキノンジアジドスルホン酸クロリド(東洋合成(株)製、NAC−5)72.3g(0.27モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン100gと混合したトリエチルアミン25.0gを、系内が35℃以上にならないように滴下した。滴下後、40℃で2時間撹拌した。トリエチルアミン塩を濾過し、濾液を水に投入した。その後、析出した沈殿を濾過で集め、さらに1%塩酸水1Lで洗浄した。その後、さらに水2Lで2回洗浄した。この沈殿を真空乾燥機で乾燥し、下記式で表されるキノンジアジド化合物(B−2)(波長350nm以上450nm以下の範囲における最大吸収波長:400nm)を得た。
(B−3)“アデカアークルズ”(登録商標)NCI−831(オキシムエステル系光重合開始剤、波長350nm以上450nm以下の範囲における最大吸収波長:373nm)
(F−1)“KAYARAD”(登録商標) DPHA(日本化薬(株)製;ジペンタエリスリトールヘキサアクリレート)。
アルカリ可溶性樹脂(a)として合成例2で得られたポリイミド前駆体(A−1)10g、感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)3g、化合物(c)としてPlast Yellow 8070(一般名C.I.Disperse Yellow 201、有本化学工業(株)製、以下PY8070と略記することもある。)(吸収極大波長445nm)0.1g、を計り、γ−ブチロラクトン(以下、GBLと記す場合もある。)50gに溶解させて感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度105mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は1.20%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)2.7g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)0.3gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度100mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は1.00%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)2.4g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)0.6gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度95mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.95%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)1.8g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)1.2gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度95mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.90%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)1.2g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)1.8gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度93mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.86%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)0.6g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)2.4gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度100mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.81%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)0.3g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)2.7gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度105mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.77%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)0.15g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)2.85gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度110mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.72%であった。
感光性化合物(b)として、感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)0.12g、感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)2.88gを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度125mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.68%であった。
感光性化合物(b1)に該当する合成例9で得られたキノンジアジド化合物(B−1)の代わりに感光性化合物(b1)に該当するトリフルオロメタンスルホン酸−1,8−ナフタルイミド(波長350nm以上450nm以下の範囲における最大吸収波長:350nm)0.6gを用いた以外は実施例6と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度110mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は1.10%であった。
Plast Yellow 8070を使用しない以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度90mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%より大きい値であった。吸水率は1.35%であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例1と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度130mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は0.60%であった。
化合物(c)のPlast Yellow 8070の代わりに、化合物(d)に該当するOil Scarlet5206(一般名C.I.Solvent Red 18、有本化学工業(株)製、以下OS5206と略記することもある。)(吸収極大波長515nm)0.3gのみを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度105mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%より大きい値であった。吸水率は0.95%であった。
化合物(c)のPlast Yellow 8070の代わりに、化合物(e)に該当するPlast Blue8540(一般名C.I.Solvent Blue 63、有本化学工業(株)製、以下PB8540と略記することもある。)(吸収極大波長645nm)0.6gのみを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度110mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%より大きい値であった。吸水率は0.95%であった。
化合物(c)のPlast Yellow 8070の代わりに、化合物(c)〜(e)のいずれにも該当しない5−ニトロアセナフテン(東京化成(株)製、吸収極大波長371nm)0.3gのみを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度400mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。吸水率は1.05%であった。
アルカリ可溶性樹脂(a)として合成例3で得られたポリイミド樹脂(A−2)10gを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度140mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例4で得られたフェノール樹脂(A−3)10gを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度95mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例5で得られたポリヒドロキシスチレン樹脂(A−4)10gを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度115mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例6で得られたシロキサンポリマー(A−5)10g、溶媒としてPGMEAを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度145mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例7で得られた環状オレフィン重合体(A−6)10g、溶媒としてPGMEAを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度145mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例8で得られたカルド樹脂(A−7)10g、溶媒としてPGMEAを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度150mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例2で得られたポリアミド酸前駆体(A−1)8g、合成例4で得られたフェノール樹脂(A−3)2gを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度95mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例11と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度190mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例12と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度130mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例13と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度150mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例14と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度200mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例15と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度200mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例16と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度200mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例17と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度130mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
化合物(d)に該当するOil Scarlet5206 0.3gをさらに加えた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度100mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
化合物(e)に該当するPlast Blue8540 0.6gをさらに加えた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度110mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
化合物(c)としてPlast Yellow8070の代わりにピグメントイエロー150(商品名E4GNGT、ランクセス(株)製)(吸収極大波長425nm)0.15gを用いた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度105mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
化合物(d)に該当するOil Scarlet5206 0.3gをさらに加えた以外は実施例20と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度115mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
ピグメントレッド254(商品名イルガポアレッドBK−CF、チバ・スペシャルティケミカルズ(株)製)(吸収極大波長550nm)0.15gをさらに加えた以外は実施例20と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度125mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
化合物(d)に該当するOil Scarlet5206 0.3g、および、化合物(e)に該当するPlast Blue8540 0.6gをさらに加えた以外は実施例5と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度100mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
化合物(c)としてPlast Yellow8070の代わりにピグメントイエロー150 0.15gを用いた以外は実施例23と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度120mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
化合物(e)としてPlast Blue 8540の代わりにピグメントブルー15:6(商品名リオノールブルー7602、東洋インキ(株)製)(吸収極大波長670nm)0.15gを用いた以外は実施例24と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度190mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
感光性化合物(b)として光重合開始剤NCI−831(B−3)2.5gのみを用い、さらにラジカル重合性化合物(f)としてDPHA(F−1)12.0gを加えた以外は実施例23と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度120mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
アルカリ可溶性樹脂(a)として合成例3で得られたポリイミド樹脂(A−2)10gを用いた以外は実施例26と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度110mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
(比較例13)
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例18と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度135mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例19と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度135mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例20と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度140mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例21と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度170mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例22と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度250mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜450nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例23と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度140mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例24と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度160mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
感光性化合物(b)として感光性化合物(b1)に該当しない合成例10で得られたキノンジアジド化合物(B−2)3.0gのみを用いた以外は実施例25と同様にして感光性着色樹脂組成物のワニスを得た。このワニスを用いてプリベーク膜を作製し、感度を測定したところ、感度240mJ/cm2であった。また加熱処理後の光透過率を測定したところ、400〜650nmの光透過率が60%以下であった。
2:配線
3:絶縁膜
4:平坦化膜
5:ITO(透明電極)
6:基板
7:コンタクトホール
8:絶縁層
Claims (15)
- アルカリ可溶性樹脂(a)、感光性化合物(b)、波長400nm以上490nm未満の範囲に吸収極大を持つ化合物(c)とを含有し、前記感光性化合物(b)が感光性化合物(b1)を含み、前記感光性化合物(b1)が、波長350nm以上450nm以下の範囲における最大吸収波長を波長350nm以上390nm以下の範囲に有する感光性着色樹脂組成物。
- 前記感光性化合物(b1)の含有量が全感光性化合物(b)100質量部に対して5質量部以上である請求項1に記載の感光性着色樹脂組成物。
- 前記感光性化合物(b1)が4−ナフトキノンジアジドスルホニルエステル化合物である請求項1または2に記載の感光性着色樹脂組成物。
- 前記アルカリ可溶性樹脂(a)が、ポリイミド、ポリイミド前駆体、ポリベンゾオキサゾール、ポリベンゾオキサゾール前駆体、フェノール樹脂、アルカリ可溶性基を有するラジカル重合性モノマーを含む重合体、シロキサンポリマー、環状オレフィン重合体、およびカルド樹脂の中から選ばれる少なくとも1種のアルカリ可溶性樹脂またはそれらの共重合体である請求項1〜3のいずれかに記載の感光性着色樹脂組成物。
- 前記アルカリ可溶性樹脂(a)が、一般式(1)または一般式(2)で表される構造単位を有する、請求項1〜4のいずれかに記載の感光性着色樹脂組成物。
- 前記感光性化合物(b1)が光重合開始剤であり、さらにラジカル重合性化合物(f)を含有する請求項1、2、4および5のいずれかに記載の感光性着色樹脂組成物。
- さらに波長490nm以上580nm未満の範囲に吸収極大を持つ化合物(d)、波長580nm以上800nm未満の範囲に吸収極大を持つ化合物(e)を含有する請求項1〜6のいずれかに記載の感光性着色樹脂組成物。
- 前記波長400nm以上490nm未満の範囲に吸収極大を持つ化合物(c)、波長490nm以上580nm未満の範囲に吸収極大を持つ化合物(d)、および波長580nm以上800nm未満の範囲に吸収極大を持つ化合物(e)が、それぞれ染料である請求項1〜7のいずれかに記載の感光性着色樹脂組成物。
- 前記波長400nm以上490nm未満の範囲に吸収極大を持つ化合物(c)が黄色または橙色染料、波長490nm以上580nm未満の範囲に吸収極大を持つ化合物(d)が赤色または紫色染料、波長580nm以上800nm未満の範囲に吸収極大を持つ化合物(e)が青色または緑色染料である請求項9に記載の感光性着色樹脂組成物。
- 請求項1〜9のいずれかに記載の感光性着色樹脂組成物を、基板に塗布し、塗布膜を形成する塗布工程、前記塗布膜を乾燥し感光性着色樹脂膜を形成する乾燥工程、乾燥した感光性着色樹脂膜を露光する露光工程、露光した感光性着色樹脂膜を現像する現像工程、および現像した感光性着色樹脂膜を加熱処理する加熱処理工程を含む耐熱性着色樹脂膜の製造方法。
- 前記塗布工程がスリットノズルを用いて前記感光性着色樹脂組成物を基板に塗布し塗布膜を形成する工程を含み、前記乾燥工程が前記塗布膜を減圧乾燥し感光性着色樹脂膜を形成する工程を含む、請求項10に記載の耐熱性着色樹脂膜の製造方法。
- 前記露光工程がブロードバンドで露光する工程を含む請求項10または11に記載の耐熱性着色樹脂膜の製造方法。
- 基板上に形成された第一電極と前記第一電極の周縁を覆うように形成された絶縁層と、前記第一電極に対向して設けられた第二電極とを含む表示装置であって、前記絶縁層が請求項1〜9のいずれかに記載の感光性着色樹脂組成物を硬化した硬化膜である表示装置。
- 基板上に形成された配線を含む薄膜トランジスタ(TFT)と、前記配線を含むTFTの凹凸を覆う状態で設けられた平坦化膜、前記平坦化膜上に設けられた表示素子とを備えてなる表示装置であって、前記平坦化膜が請求項1〜9のいずれかに記載の感光性着色樹脂組成物を硬化した硬化膜である表示装置。
- 解像度が50ppi以上である請求項13または14に記載の表示装置。
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