JP2002088136A - 光重合性不飽和樹脂および該樹脂を含有する感光性樹脂組成物 - Google Patents
光重合性不飽和樹脂および該樹脂を含有する感光性樹脂組成物Info
- Publication number
- JP2002088136A JP2002088136A JP2000277236A JP2000277236A JP2002088136A JP 2002088136 A JP2002088136 A JP 2002088136A JP 2000277236 A JP2000277236 A JP 2000277236A JP 2000277236 A JP2000277236 A JP 2000277236A JP 2002088136 A JP2002088136 A JP 2002088136A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- general formula
- resin composition
- photopolymerizable unsaturated
- represented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 239000011347 resin Substances 0.000 title claims abstract description 72
- 239000011342 resin composition Substances 0.000 title claims abstract description 50
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 epoxy acrylate compound Chemical class 0.000 claims description 36
- 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 claims description 27
- 239000000758 substrate Substances 0.000 claims description 27
- 239000000049 pigment Substances 0.000 claims description 20
- 150000008065 acid anhydrides Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 10
- 238000001723 curing Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 238000011161 development Methods 0.000 claims description 7
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 5
- 238000000016 photochemical curing Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 57
- 239000002904 solvent Substances 0.000 abstract description 20
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 12
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- 239000007864 aqueous solution Substances 0.000 description 10
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- JRPBSTGRRSTANR-UHFFFAOYSA-N 2,6-bis(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC(CC(C)C)=C1O JRPBSTGRRSTANR-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
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- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- 239000004115 Sodium Silicate Substances 0.000 description 2
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
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- 238000005336 cracking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
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- 238000004544 sputter deposition Methods 0.000 description 2
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- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
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- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- UYFJYGWNYQCHOB-UHFFFAOYSA-N 1-(4-tert-butylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)(C)C)C=C1 UYFJYGWNYQCHOB-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CAQYAZNFWDDMIT-UHFFFAOYSA-N 1-ethoxy-2-methoxyethane Chemical compound CCOCCOC CAQYAZNFWDDMIT-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
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| JP2002145999A (ja) * | 2000-11-15 | 2002-05-22 | Nagase Kasei Kogyo Kk | 光重合性不飽和樹脂および該樹脂を含有する感光性樹脂組成物 |
| JP2004069754A (ja) * | 2002-08-01 | 2004-03-04 | Tokyo Ohka Kogyo Co Ltd | 光重合性黒色組成物及び黒色パターンの形成方法 |
| JP2004137262A (ja) * | 2002-09-27 | 2004-05-13 | Osaka Gas Co Ltd | フルオレン誘導体及び光活性化合物 |
| JP2005037516A (ja) * | 2003-07-17 | 2005-02-10 | Sumitomo Chemical Co Ltd | 感放射線性樹脂組成物 |
| JP2006195410A (ja) * | 2005-01-12 | 2006-07-27 | Qimei Industry Co Ltd | カラーフィルター用感光性樹脂組成物 |
| WO2006121062A1 (ja) * | 2005-05-11 | 2006-11-16 | Toppan Printing Co., Ltd. | アルカリ現像型感光性樹脂組成物、それを用いて形成した液晶分割配向制御突起付き基板及びカラーフィルタ、並びに液晶表示装置 |
| JP2007045925A (ja) * | 2005-08-10 | 2007-02-22 | Tokyo Ohka Kogyo Co Ltd | 不飽和基含有化合物の製造方法および不飽和基化合物を含む樹脂溶液 |
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| JP2009242783A (ja) * | 2008-03-10 | 2009-10-22 | Nagase Chemtex Corp | 撥液性樹脂組成物 |
| EP2120094A2 (en) | 2008-05-12 | 2009-11-18 | Fujifilm Corporation | Black photosensitive resin composition, and color filter and method of producing the same |
| JP2009276633A (ja) * | 2008-05-15 | 2009-11-26 | Toppan Printing Co Ltd | 着色アルカリ現像型感光性樹脂組成物、それを用いたカラーフィルタ並びに液晶分割配向制御用突起付き基板及び該基板を備えた液晶表示装置 |
| JP2010229173A (ja) * | 2009-03-25 | 2010-10-14 | Nippon Steel Chem Co Ltd | アルカリ可溶性樹脂及びその製造方法、並びにアルカリ可溶性樹脂を用いた感光性樹脂組成物 |
| CN101450992B (zh) * | 2007-12-07 | 2010-12-22 | 比亚迪股份有限公司 | 一种聚合物及其制备方法和含有该聚合物的导电胶 |
| JP2012206968A (ja) * | 2011-03-29 | 2012-10-25 | Osaka Gas Chem Kk | フルオレン骨格を有する（メタ）アクリレート |
| JP2013130843A (ja) * | 2011-12-22 | 2013-07-04 | Tokyo Ohka Kogyo Co Ltd | ブラックカラムスペーサ用感光性樹脂組成物、ブラックカラムスペーサ、表示装置、及びブラックカラムスペーサの形成方法 |
| JP2016110065A (ja) * | 2014-08-12 | 2016-06-20 | 株式会社Ｄｎｐファインケミカル | カラーフィルタ用着色樹脂組成物、カラーフィルタ、及び表示装置 |
| JP2016194021A (ja) * | 2015-04-01 | 2016-11-17 | 大阪ガスケミカル株式会社 | フルオレン骨格を有するエポキシ樹脂及びその製造方法 |
| KR20180111888A (ko) | 2016-02-03 | 2018-10-11 | 타오카 케미컬 컴퍼니 리미티드 | 플루오렌 골격을 갖는 비스페놀류 및 그 제조 방법, 그리고 그 비스페놀류로부터 유도되는 폴리아릴레이트 수지, (메트)아크릴레이트 화합물 및 에폭시 수지 |
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| JP2002145999A (ja) * | 2000-11-15 | 2002-05-22 | Nagase Kasei Kogyo Kk | 光重合性不飽和樹脂および該樹脂を含有する感光性樹脂組成物 |
| JP2004069754A (ja) * | 2002-08-01 | 2004-03-04 | Tokyo Ohka Kogyo Co Ltd | 光重合性黒色組成物及び黒色パターンの形成方法 |
| JP2004137262A (ja) * | 2002-09-27 | 2004-05-13 | Osaka Gas Co Ltd | フルオレン誘導体及び光活性化合物 |
| JP2005037516A (ja) * | 2003-07-17 | 2005-02-10 | Sumitomo Chemical Co Ltd | 感放射線性樹脂組成物 |
| JP2006195410A (ja) * | 2005-01-12 | 2006-07-27 | Qimei Industry Co Ltd | カラーフィルター用感光性樹脂組成物 |
| WO2006121062A1 (ja) * | 2005-05-11 | 2006-11-16 | Toppan Printing Co., Ltd. | アルカリ現像型感光性樹脂組成物、それを用いて形成した液晶分割配向制御突起付き基板及びカラーフィルタ、並びに液晶表示装置 |
| JP2007045925A (ja) * | 2005-08-10 | 2007-02-22 | Tokyo Ohka Kogyo Co Ltd | 不飽和基含有化合物の製造方法および不飽和基化合物を含む樹脂溶液 |
| JP2007119720A (ja) * | 2005-09-29 | 2007-05-17 | Dainippon Printing Co Ltd | 硬化性樹脂組成物 |
| JP2007246802A (ja) * | 2006-03-17 | 2007-09-27 | Toyo Ink Mfg Co Ltd | ポリエステル樹脂およびその製造方法 |
| CN101450992B (zh) * | 2007-12-07 | 2010-12-22 | 比亚迪股份有限公司 | 一种聚合物及其制备方法和含有该聚合物的导电胶 |
| JP2009242783A (ja) * | 2008-03-10 | 2009-10-22 | Nagase Chemtex Corp | 撥液性樹脂組成物 |
| EP2120094A2 (en) | 2008-05-12 | 2009-11-18 | Fujifilm Corporation | Black photosensitive resin composition, and color filter and method of producing the same |
| US8211598B2 (en) | 2008-05-12 | 2012-07-03 | Fujifilm Corporation | Black photosensitive resin composition, and color filter and method of producing the same |
| JP2009276633A (ja) * | 2008-05-15 | 2009-11-26 | Toppan Printing Co Ltd | 着色アルカリ現像型感光性樹脂組成物、それを用いたカラーフィルタ並びに液晶分割配向制御用突起付き基板及び該基板を備えた液晶表示装置 |
| JP2010229173A (ja) * | 2009-03-25 | 2010-10-14 | Nippon Steel Chem Co Ltd | アルカリ可溶性樹脂及びその製造方法、並びにアルカリ可溶性樹脂を用いた感光性樹脂組成物 |
| TWI449724B (zh) * | 2009-03-25 | 2014-08-21 | Nippon Steel & Sumikin Chem Co | Alkali-soluble resin and method for producing the same, and a photosensitive resin composition using an alkali-soluble resin |
| JP2012206968A (ja) * | 2011-03-29 | 2012-10-25 | Osaka Gas Chem Kk | フルオレン骨格を有する（メタ）アクリレート |
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| JP2016110065A (ja) * | 2014-08-12 | 2016-06-20 | 株式会社Ｄｎｐファインケミカル | カラーフィルタ用着色樹脂組成物、カラーフィルタ、及び表示装置 |
| JP2016194021A (ja) * | 2015-04-01 | 2016-11-17 | 大阪ガスケミカル株式会社 | フルオレン骨格を有するエポキシ樹脂及びその製造方法 |
| KR20180111888A (ko) | 2016-02-03 | 2018-10-11 | 타오카 케미컬 컴퍼니 리미티드 | 플루오렌 골격을 갖는 비스페놀류 및 그 제조 방법, 그리고 그 비스페놀류로부터 유도되는 폴리아릴레이트 수지, (메트)아크릴레이트 화합물 및 에폭시 수지 |
| US10689318B2 (en) | 2016-02-03 | 2020-06-23 | Taoka Chemical Co., Ltd. | Bisphenol having fluorene skeleton, method for producing same, polyarylate resin, (meth)acrylate compound and epoxy resin which are derived from the bisphenol |
| CN116041235A (zh) * | 2023-01-10 | 2023-05-02 | 阜阳欣奕华材料科技有限公司 | 巯基改性芴树脂低聚物及其制备方法、感光性树脂组合物、彩色滤光片和图形显示装置 |
| CN116041235B (zh) * | 2023-01-10 | 2024-05-14 | 阜阳欣奕华材料科技有限公司 | 巯基改性芴树脂低聚物及其制备方法、感光性树脂组合物、彩色滤光片和图形显示装置 |
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