JP5705371B2 - 染料を含む高分子化合物及びこれを含む硬化性樹脂組成物 - Google Patents
染料を含む高分子化合物及びこれを含む硬化性樹脂組成物 Download PDFInfo
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- JP5705371B2 JP5705371B2 JP2014506352A JP2014506352A JP5705371B2 JP 5705371 B2 JP5705371 B2 JP 5705371B2 JP 2014506352 A JP2014506352 A JP 2014506352A JP 2014506352 A JP2014506352 A JP 2014506352A JP 5705371 B2 JP5705371 B2 JP 5705371B2
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- 239000002904 solvent Substances 0.000 claims description 15
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
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- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000012719 thermal polymerization Methods 0.000 claims description 5
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- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical class C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZLFVRXUOSPRRKQ-VHEBQXMUSA-N CI Pigment Red 3 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-VHEBQXMUSA-N 0.000 description 1
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- RYIHVCKWWPHXMZ-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-sulfanylacetyl)oxy-2-[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(CO)(COC(=O)CS)COC(=O)CS RYIHVCKWWPHXMZ-UHFFFAOYSA-N 0.000 description 1
- OCCLJFJGIDIZKK-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(3-sulfanylpropanoyloxy)-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CO)(COC(=O)CCS)COC(=O)CCS OCCLJFJGIDIZKK-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 150000003927 aminopyridines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- NJVHCUNZAMFQNA-UHFFFAOYSA-N azane;n-hydroxy-n-phenylnitrous amide Chemical compound N.O=NN(O)C1=CC=CC=C1 NJVHCUNZAMFQNA-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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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- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
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- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 239000010439 graphite Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- ALIATVYMFGMEJC-UHFFFAOYSA-N phenyl-[2,4,6-tris(methylamino)phenyl]methanone Chemical compound CNC1=CC(NC)=CC(NC)=C1C(=O)C1=CC=CC=C1 ALIATVYMFGMEJC-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical class N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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Description
<合成例1>
比較例2:低分子形態の染料(A−2)とグリーン顔料(G58)を含む硬化性樹脂組成物
実施例1:合成例1の高分子を含む硬化性樹脂組成物
実施例2:合成例2の高分子を含む硬化性樹脂組成物
実施例3:合成例1の高分子とグリーン顔料(G58)を含む硬化性樹脂組成物
実施例4:合成例2の高分子とグリーン顔料(G58)を含む硬化性樹脂組成物
<実験例1>
<実験例2>
<実験例3>
Claims (17)
- 下記化学式1で表される繰り返し単位と、
下記化学式2で表される繰り返し単位と、
を含む高分子化合物。
R1からR4は互いに同一であるか異なっており、それぞれ独立して水素または炭素数1から5のアルキル基であり、
R5は、フェニル基で置換もしくは非置換の炭素数2から6のアルキルエステル基、及び炭素数1から3のアルキル基またはハロゲン基で置換もしくは非置換のフェニルエステル基からなる群より選択されるものであり、
a及びbは、繰り返し単位のモル混合比であって、それぞれ独立して5から50である。 - 前記高分子化合物は、下記化学式3で表される繰り返し単位をさらに含むことを特徴とする請求項1に記載の高分子化合物。
R6からR7は、互いに同一であるか異なっており、それぞれ独立して水素または炭素数1から5のアルキル基であり、
R8は、直接連結されるか、ハロゲン基またはフェニル基で置換もしくは非置換の炭素数1から6のアルキレン基であり、
cは、繰り返し単位のモル混合比であって、それぞれ独立して5から50である。 - 前記高分子化合物の重量平均分子量は、1,000から100,000であることを特徴とする請求項1または請求項2に記載の高分子化合物。
- 前記高分子化合物は、下記化学式4で表される繰り返し単位を含むことを特徴とする請求項1に記載の高分子化合物。
a及びbはモル混合比であって、それぞれ独立して5から50である。 - 前記高分子化合物は、下記化学式5で表される繰り返し単位を含むことを特徴とする請求項2に記載の高分子化合物。
a、b及びcはモル混合比であって、それぞれ独立して5から50である。 - 請求項1から請求項5のいずれか一項に記載の高分子化合物と、
アルカリ可溶性高分子樹脂を含むバインダー樹脂と、
エチレン性不飽和結合を含む重合性化合物と、
光開始剤と、
溶媒と
を含む硬化性樹脂組成物。 - 前記高分子化合物の含量は、硬化性樹脂組成物の総重量を基準に0.1から10重量%であることを特徴とする請求項6に記載の硬化性樹脂組成物。
- 前記アルカリ可溶性高分子樹脂を含むバインダー樹脂は、重量平均分子量が3,000から150,000であることを特徴とする請求項6または請求項7に記載の硬化性樹脂組成物。
- 前記アルカリ可溶性高分子樹脂を含むバインダー樹脂の含量は、硬化性樹脂組成物の総重量を基準に1から20重量%であることを特徴とする請求項6から請求項8のいずれか一項に記載の硬化性樹脂組成物。
- 前記エチレン性不飽和結合を含む重合性化合物の含量は、硬化性樹脂組成物の総重量を基準に0.5から30重量%であることを特徴とする請求項6から請求項9のいずれか一項に記載の硬化性樹脂組成物。
- 前記光開始剤の含量は、硬化性樹脂組成物の総重量を基準に0.1から5重量%であることを特徴とする請求項6から請求項10のいずれか一項に記載の硬化性樹脂組成物。
- 前記溶媒の含量は、硬化性樹脂組成物の総重量を基準に40から95重量%であることを特徴とする請求項6から請求項11のいずれか一項に記載の硬化性樹脂組成物。
- 前記硬化性樹脂組成物は、硬化促進剤、熱重合抑制剤、分散剤、酸化防止剤、紫外線吸収剤、レベリング剤、光増感剤、可塑剤、接着促進剤、充填剤及び界面活性剤からなる群より選択される一つまたは二つ以上の添加剤をさらに含むことを特徴とする請求項6から請求項12のいずれか一項に記載の硬化性樹脂組成物。
- 前記添加剤の含量は、硬化性樹脂組成物の総重量を基準にそれぞれ0.01から5重量%であることを特徴とする請求項13に記載の硬化性樹脂組成物。
- 請求項6から14のいずれか一項に記載の硬化性樹脂組成物を用いて製造された感光材。
- 前記感光材は、TFT LCDカラーフィルタ製造用顔料分散型感光材、TFT LCDまたは有機発光ダイオードのブラックマトリックス形成用感光材、オーバーコート層形成用感光材、コラムスペーサー感光材及びプリント配線板用感光材からなる群より選択されることを特徴とする請求項15に記載の感光材。
- 請求項6から請求項14のいずれか一項に記載の硬化性樹脂組成物を用いて製造された電子素子。
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- 2012-05-25 US US14/006,272 patent/US8999626B2/en active Active
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KR101367572B1 (ko) | 2014-03-14 |
US20140011135A1 (en) | 2014-01-09 |
JP2014523450A (ja) | 2014-09-11 |
CN103476808B (zh) | 2017-03-22 |
CN103476808A (zh) | 2013-12-25 |
US8999626B2 (en) | 2015-04-07 |
WO2013018987A1 (ko) | 2013-02-07 |
KR20130016046A (ko) | 2013-02-14 |
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