CN106256837B - Curable composition, method for producing cured product, and hard coating material - Google Patents
Curable composition, method for producing cured product, and hard coating material Download PDFInfo
- Publication number
- CN106256837B CN106256837B CN201610420826.2A CN201610420826A CN106256837B CN 106256837 B CN106256837 B CN 106256837B CN 201610420826 A CN201610420826 A CN 201610420826A CN 106256837 B CN106256837 B CN 106256837B
- Authority
- CN
- China
- Prior art keywords
- group
- curable composition
- ring
- carbon atoms
- substituent
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 239000000463 material Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000011248 coating agent Substances 0.000 title abstract description 8
- 238000000576 coating method Methods 0.000 title abstract description 8
- -1 acrylate compound Chemical class 0.000 claims abstract description 140
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 58
- 125000001424 substituent group Chemical group 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 125000000962 organic group Chemical group 0.000 claims abstract description 26
- 239000003999 initiator Substances 0.000 claims abstract description 23
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000011247 coating layer Substances 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 36
- 239000010408 film Substances 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 23
- 239000010410 layer Substances 0.000 description 20
- 125000001624 naphthyl group Chemical group 0.000 description 17
- 125000001931 aliphatic group Chemical group 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000001326 naphthylalkyl group Chemical group 0.000 description 8
- 125000003884 phenylalkyl group Chemical group 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 7
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 125000002993 cycloalkylene group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 5
- 229920002284 Cellulose triacetate Polymers 0.000 description 5
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- TXWRERCHRDBNLG-UHFFFAOYSA-N cubane Chemical compound C12C3C4C1C1C4C3C12 TXWRERCHRDBNLG-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 1
- OWSKJORLRSWYGK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) propanoate Chemical compound CCC(=O)OCCC(C)(C)OC OWSKJORLRSWYGK-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-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
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- FMVOPJLFZGSYOS-UHFFFAOYSA-N 2-[2-(2-ethoxypropoxy)propoxy]propan-1-ol Chemical compound CCOC(C)COC(C)COC(C)CO FMVOPJLFZGSYOS-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical group C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- NTKBNCABAMQDIG-UHFFFAOYSA-N 3-butoxypropan-1-ol Chemical compound CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NYNIWVWUMFHVTG-UHFFFAOYSA-N 4,6,8-trimethylundeca-1,4-diene Chemical group CC(CC=C)=CC(CC(CCC)C)C NYNIWVWUMFHVTG-UHFFFAOYSA-N 0.000 description 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- AETAGZXGBIQVKJ-UHFFFAOYSA-N P1C=CC2=C1C=CC=C2.C2(=CC=CC=C2)C=2PC=CC2 Chemical group P1C=CC2=C1C=CC=C2.C2(=CC=CC=C2)C=2PC=CC2 AETAGZXGBIQVKJ-UHFFFAOYSA-N 0.000 description 1
- YGYYWMRSBNXMOC-UHFFFAOYSA-N P1C=CC=C1.P1C=CC=C1 Chemical group P1C=CC=C1.P1C=CC=C1 YGYYWMRSBNXMOC-UHFFFAOYSA-N 0.000 description 1
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical group C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QKWLQWFMFQOKET-UHFFFAOYSA-N basketane Chemical compound C1CC2C3C4C1C1C4C3C21 QKWLQWFMFQOKET-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical group C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000004113 cyclononanyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- PIJZNCJOLUODIA-UHFFFAOYSA-N deca-1,4-diene Chemical group CCCCCC=CCC=C PIJZNCJOLUODIA-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- FJAKCEHATXBFJT-UHFFFAOYSA-N ethyl 2-oxobutanoate Chemical compound CCOC(=O)C(=O)CC FJAKCEHATXBFJT-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
- 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-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
- 239000011241 protective layer Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
- C08F299/024—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
- C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Laminated Bodies (AREA)
Abstract
The present invention relates to a curable composition, a method for producing a cured product, and a hard coating material. The invention provides a curable composition capable of forming a hard coating layer with excellent flexibility, toughness, surface hardness and transparency, and a method for producing a cured product using the curable composition and a hard coating material. The curable composition according to the present invention contains (a) a photopolymerization initiator and (B) a polyfunctional acrylate compound containing at least 1 selected from a siloxane bond, an aromatic ring and a crosslinked saturated ring, wherein the (a) photopolymerization initiator contains a compound represented by the following formula (a-1). In the formula, R1Is a specific organic group containing an aromatic ring, R2Is an organic radical of valency 1, R3Is a hydrogen atom, an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent, and m is 0 or 1.
Description
Technical Field
The present invention relates to a curable composition, and a method for producing a cured product and a hard coat material using the curable composition.
Background
Optical films are used for various image display devices such as liquid crystal displays, plasma displays, CRT displays, EL displays, and field emission displays, for example, to protect the surface, prevent reflection, and prevent glare. From the viewpoint of scratch resistance, it is known to use, as such an optical film, a hard coat material in which a hard coat layer is formed on the surface of a base material formed of triacetyl cellulose (TAC) or the like (for example, see patent document 1).
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2013-195550
Disclosure of Invention
Problems to be solved by the invention
In general, a hard coat layer used for a hard coat material is required to have excellent properties such as bendability, toughness, surface hardness, and transparency. However, the conventional hard coat layer does not sufficiently satisfy the above requirements.
The present invention has been made in view of the above problems, and an object of the present invention is to provide a curable composition capable of forming a hard coat layer excellent in bendability, toughness, surface hardness, and transparency, and a method for producing a cured product using the curable composition, and a hard coat material.
Means for solving the problems
The present inventors have found that the above problems can be solved by a curable composition containing a specific photopolymerization initiator and a specific multifunctional acrylate compound, and have completed the present invention. Specifically, the present invention provides the following.
The first embodiment of the present invention is a curable composition containing (A) a photopolymerization initiator and (B) a polyfunctional acrylate compound containing at least 1 selected from the group consisting of a siloxane bond, an aromatic ring and a crosslinked saturated ring,
the photopolymerization initiator (A) includes a compound represented by the following formula (a-1).
[ chemical formula 1]
(R1Is a group represented by the following formula (a-2), a group represented by the following formula (a-3), or a group represented by the following formula (a-4), R2Is an organic radical of valency 1, R3Is a hydrogen atom, an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent, and m is 0 or 1. )
[ chemical formula 2]
(R4Is a hydrogen atom, a nitro group, or an organic group having a valence of 1, R5And R6Independently is a chain alkyl, cyclic hydrocarbyl, or heteroaryl group, R5And R6May be bonded to each other to form a spiro ring. )
[ chemical formula 3]
(R7Independently is a 1-valent organic group, an amino group, a halogen atom, a nitro group or a cyano group, A is S or O, and n is an integer of 0-4. )
[ chemical formula 4]
(R8Is an organic radical of valency 1, R9Is a hydrogen atom, a nitro group, or a 1-valent organic group. )
A second aspect of the present invention is a method for producing a cured product, including the steps of:
a step of forming a curable composition film using the curable composition; and
and exposing the curable composition film to light.
A third aspect of the present invention is a hard coat material comprising a substrate and a hard coat layer formed on the substrate by using the curable composition.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention can provide a curable composition capable of forming a hard coat layer excellent in bendability, toughness, surface hardness, and transparency, and a method for producing a cured product using the curable composition, and a hard coat material.
Detailed Description
Curable composition
The curable composition according to the present invention contains (a) a photopolymerization initiator and (B) a polyfunctional acrylate compound containing at least 1 selected from a siloxane bond, an aromatic ring and a crosslinked saturated ring, wherein the (a) photopolymerization initiator contains a compound represented by the formula (a-1). The hard coat layer obtained from the curable composition of the present invention is excellent in flexibility, toughness, surface hardness and transparency, and can be suitably used as a hard coat material.
[ photopolymerization initiator (A) ]
The photopolymerization initiator (A) is not particularly limited as long as it contains the compound represented by the above formula (a-1). The curable composition of the present invention contains (a) a photopolymerization initiator, and therefore has high sensitivity and can be sufficiently cured with a small amount of energy rays. (A) The photopolymerization initiator may be used alone or in combination of 2 or more.
In the above formula (a-1), R1Is a group represented by the formula (a-2), a group represented by the formula (a-3) or a group represented by the formula (a-4).
As R2Examples of preferred organic groups of (A) and (B) are the same as those of R described later4Similarly, there may be mentioned alkyl, alkoxy, cycloalkyl, cycloalkoxy, saturated aliphatic acyl, alkoxycarbonyl, saturated aliphatic acyloxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzoyl, optionally substituted phenoxycarbonyl, optionally substituted benzoyloxy, optionally substituted phenylalkyl, optionally substituted naphthyl, optionally substituted naphthyloxy, optionally substituted naphthoyl, optionally substituted naphthyloxycarbonyl, optionally substituted naphthoyloxy, optionally substituted naphthylalkyl, optionally substituted heterocyclo (heterocylyl), optionally substituted heterocyclylcarbonyl, amino substituted by 1 or 2 organic groups, morpholin-1-yl, and the like, And piperazin-1-yl and the like.
R2In the case of an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 6. In addition, R2When the alkyl group is used, it may be a straight chain or a branched chain. As R2Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, n-decyl, and isodecyl groups. In addition, R2When it is an alkyl group, an alkaneThe groups may contain ether linkages (-O-) in the carbon chain. Examples of the alkyl group having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.
R2In the case of an alkoxy group, the number of carbon atoms of the alkoxy group is preferably 1 to 20, more preferably 1 to 6. In addition, R2When the alkoxy group is used, it may be a straight chain or a branched chain. As R2Specific examples of the alkoxy group include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, sec-pentyloxy, tert-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, isooctyloxy, sec-octyloxy, tert-octyloxy, n-nonyloxy, isononyloxy, n-decyloxy, and isodecyloxy. In addition, R2In the case of an alkoxy group, the alkoxy group may contain an ether bond (-O-) in the carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include methoxyethoxy, ethoxyethoxy, methoxyethoxyethoxy, ethoxyethoxyethoxy, propyloxyethoxyethoxyethoxy, and methoxypropyloxy.
R2When the alkyl group is a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms of the cycloalkyl group or the cycloalkoxy group is preferably 3 to 10, more preferably 3 to 6. As R2Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. As R2Specific examples of the cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.
R2In the case of a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, the number of carbon atoms in the saturated aliphatic acyl group or the saturated aliphatic acyloxy group is preferably 2 to 21, more preferably 2 to 7. As R2Specific examples of the saturated aliphatic acyl group include acetyl, propionyl, n-butyryl, 2-methylpropionyl, n-valeryl, 2-dimethylpropionyl, n-hexanoyl, n-heptanoyl, n-octanoyl, n-nonanoyl, n-decanoyl, n-undecanoyl, n-dodecanoyl, n-tridecanoyl, n-tetradecanoyl, n-pentadecanoyl, n-hexadecanoyl, etc. As R2Specific examples of the saturated aliphatic acyloxy group include an acetyloxy group, a propionyloxy group, a n-butyryloxy group, a 2-methylpropionyloxy group, a n-pentanoyloxy group, a 2, 2-dimethylpropionyloxy group, a n-hexanoyloxy group, a n-heptanoyloxy group, a n-octanoyloxy group, a n-nonanoyloxy group, a n-decanoyloxy group, a n-undecanoyloxy group, a n-dodecanoyloxy group, a n-tridecanoyloxy group, a n-tetradecanoyloxy group, a n-pentadecanoyloxy group, and a n-hexadecanoyloxy group.
R2In the case of an alkoxycarbonyl group, the number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 20, more preferably 2 to 7. As R2Specific examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, a sec-butyloxycarbonyl group, a tert-butyloxycarbonyl group, an n-pentyloxycarbonyl group, an isopentyloxycarbonyl group, a sec-pentyloxycarbonyl group, a tert-pentyloxycarbonyl group, an n-hexyloxycarbonyl group, an n-heptyloxycarbonyl group, an n-octyloxycarbonyl group, an isooctyloxycarbonyl group, a sec-octyloxycarbonyl group, a tert-octyloxycarbonyl group, an n-nonyloxycarbonyl group, an isononyloxycarbonyl group, an n-decyloxycarbonyl group, and an isodecyloxycarbonyl group.
R2In the case of phenylalkyl, the number of carbon atoms in phenylalkyl is preferably 7 to 20, more preferably 7 to 10. In addition, R2In the case of a naphthylalkyl group, the number of carbon atoms in the naphthylalkyl group is preferably 11 to 20, more preferably 11 to 14. As R2Specific examples of phenylalkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl and 4-phenylbutyl. As R2Specific examples of naphthylalkyl groups include α -naphthylmethyl, β -naphthylmethyl, 2- (α -naphthyl) ethyl and 2- (β -naphthyl) ethyl2When it is phenylalkyl or naphthylalkyl, R2Can be in phenyl or naphthylFurther having a substituent.
R2When it is a heterocyclic group, the heterocyclic group is a 5-or 6-membered monocyclic ring containing 1 or more N, S, O atoms, or a heterocyclic group in which the monocyclic rings are fused with each other or the monocyclic ring is fused with a benzene ring. When the heterocyclic group is a condensed ring, the number of rings is 3 or less. The heterocyclic group may be an aromatic group (heteroaryl group) or a non-aromatic group. Examples of the heterocyclic ring constituting the heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline (cinnoline), quinoxaline and the like. R2When it is a heterocyclic group, the heterocyclic group may further have a substituent.
R2When it is a heterocyclylcarbonyl group, the heterocyclyl group and R contained in the heterocyclylcarbonyl group2The same applies to heterocyclic groups.
R2In the case of an amino group substituted with 1 or 2 organic groups, preferable examples of the organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a saturated aliphatic acyl group having 2 to 21 carbon atoms, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoyl group which may have a substituent, a naphthylalkyl group having 11 to 20 carbon atoms which may have a substituent, a heterocyclic group and the like. Specific examples of these preferred organic groups and R2The same is true. Specific examples of the amino group substituted with 1 or 2 organic groups include methylamino, ethylamino, diethylamino, n-propylamino, di-n-propylamino, isopropylamino, n-butylamino, di-n-butylamino, n-pentylamino, n-hexylamino, n-heptylamino, n-octylamino, n-nonylamino, n-decylamino, phenylamino, naphthylamino, acetylamino, propionylamino, n-butyrylamino, n-valerylaminoAnd (c) a phenyl group, a hexanoylamino group, a heptanoylamino group, a octanoylamino group, a decanoylamino group, a benzoylamino group, α -naphthoylamino group, β -naphthoylamino group and the like.
As R2The substituent in the case where the phenyl group, naphthyl group and heterocyclic group contained in the above-mentioned group further have a substituent, examples thereof include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a saturated aliphatic acyl group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl, piperazin-1-yl, halogen, nitro, and cyano. R2The number of the substituents in the case where the phenyl group, naphthyl group and heterocyclic group contained in (1) further have a substituent is not particularly limited as long as the object of the present invention is not impaired, and is preferably 1 to 4. R2When the phenyl group, naphthyl group and heterocyclic group included in (1) have a plurality of substituents, the substituents may be the same or different.
In addition, as R2Also preferred are cycloalkylalkyl groups, phenoxyalkyl groups which may have a substituent on the aromatic ring, and phenylthioalkyl groups which may have a substituent on the aromatic ring. Phenoxyalkyl group, and phenylthioalkyl group-optionally-substituted group and R2The phenyl group contained in (1) may have the same substituent.
In the organic radical, as R2Preferred examples thereof include an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, a cycloalkylalkyl group, and a phenylthioalkyl group which may have a substituent on the aromatic ring. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, particularly preferably an alkyl group having 1 to 4 carbon atoms, and most preferably a methyl group. Among the phenyl groups which may have a substituent, a methylphenyl group is preferable, and a 2-methylphenyl group is more preferable. The number of carbon atoms of the cycloalkyl group contained in the cycloalkylalkyl group is preferably 5 to 10, more preferably 5 to 8, and particularly preferably 5 or 6. The number of carbon atoms of the alkylene group contained in the cycloalkylalkyl group is preferably 1 to 8, more preferably 1 to 4, and particularly preferably 2. Among cycloalkylalkyl groups, preferred isSelecting cyclopentylethyl. The number of carbon atoms of the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring is preferably 1 to 8, more preferably 1 to 4, and particularly preferably 2. Among the phenylsulfanylalkyl groups which may have a substituent on the aromatic ring, 2- (4-chlorophenylthio) ethyl is preferred.
Hereinbefore, to R2Has been described as R2Preferred is a group represented by the following formula (R2-1) or (R2-2).
[ chemical formula 5]
(in the formulae (R2-1) and (R2-2), R10And R11Each is an organic group, p is an integer of 0 to 4, R10And R11When present in adjacent positions on the phenyl ring, R10And R11Can be bonded to each other to form a ring, q is an integer of 1 to 8, R is an integer of 1 to 5, s is an integer of 0 to (R +3), R12Is an alkyl group. )
With respect to R in the formula (R2-1)10And R11Examples of organic radicals of (1), with R2The same is true. As R10Preferably alkyl or phenyl. R10When the alkyl group is used, the number of carbon atoms is preferably 1 to 10, more preferably 1 to 5, particularly preferably 1 to 3, and most preferably 1. Namely, R10Most preferred is methyl. R10And R11When a ring is bonded to form a bond, the ring may be an aromatic ring or an aliphatic ring. As R10And R11Preferred examples of the group represented by the formula (R2-1) having a ring formed thereon include naphthalen-1-yl, 1, 2, 3, 4-tetrahydronaphthalen-5-yl and the like. In the formula (R2-1), p is an integer of 0 to 4, preferably 0 or 1, more preferably 0.
In the above formula (R2-2), R12Is an alkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and particularly preferably 1 to 3. As R12Among these, methyl is more preferable.
In the formula (R2-2), R is an integer of 1 to 5, preferably an integer of 1 to 3, and more preferably 1 or 2. In the formula (R2-2), s is an integer of 0 to (R +3), preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0. In the formula (R2-2), q is an integer of 1 to 8, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and particularly preferably 1 or 2.
In the formula (a-1), R3Is a hydrogen atom, an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent. As R3The substituent which may be contained in the alkyl group is preferably phenyl, naphthyl, or the like. In addition, as R3The substituent which may be contained in the aryl group is preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a halogen atom or the like.
In the formula (a-1), as R3Examples thereof include preferably a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, phenyl group, benzyl group, methylphenyl group and naphthyl group, and among these, more preferably methyl group or phenyl group.
In the formula (a-2), R4Is hydrogen atom, nitro or 1-valent organic group. R4To the fluorene ring in formula (a-2) and to- (CO) in formula (a-1)mThe group represented by (A) is on a 6-membered aromatic ring different from the 6-membered aromatic ring. If this condition is satisfied, then R in the formula (a-2)4The bonding position with respect to the fluorene ring is not particularly limited. From easy synthesis of R1A compound represented by the formula (a-1) which is a group represented by the formula (a-2), R4The bonding position to the fluorene ring is preferably the 2-position in the fluorene ring.
R4When it is an organic group, R4The organic group is not particularly limited as long as the object of the present invention is not impaired, and may be appropriately selected from various organic groups. As R4Preferred examples of organic radicals are, with R2Similarly, there may be mentioned alkyl, alkoxy, cycloalkyl, cycloalkoxy, saturated aliphatic acyl, alkoxycarbonyl, saturated aliphatic acyloxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzoyl, optionally substituted phenoxycarbonyl, optionally substituted benzoylAn oxy group, a phenylalkyl group which may have a substituent, a naphthyl group which may have a substituent, a naphthyloxy group which may have a substituent, a naphthoyl group which may have a substituent, a naphthyloxycarbonyl group which may have a substituent, a naphthoyloxy group which may have a substituent, a naphthylalkyl group which may have a substituent, a heterocyclic carbonyl group which may have a substituent, an amino group substituted with 1 or 2 organic groups, a morpholin-1-yl group, a piperazin-1-yl group and the like. Specific examples of these groups and for R2The specific examples described are the same.
In the above-specified groups, as R4Is nitro or R13The group represented by-CO-is preferable because the sensitivity tends to be improved. R13The organic group is not particularly limited as long as the object of the present invention is not impaired, and may be selected from various organic groups. With respect to preference as R13Examples of the group (b) include an alkyl group having 1 to 20 carbon atoms, an optionally substituted phenyl group, an optionally substituted naphthyl group, and an optionally substituted heterocyclic group. As R13Among these groups, 2-methylphenyl, thiophen-2-yl and α -naphthyl are particularly preferable.
In addition, R4In the case of a hydrogen atom, the transparency tends to be good, and it is preferable. In addition, R is4Is a hydrogen atom and R2In the case of (R2-2), the transparency tends to be more excellent.
In the formula (a-2), R5And R6Each is a chain alkyl group, a cyclic hydrocarbon group, or a heteroaryl group. Of these groups, as R5And R6Preferably, a chain alkyl group.
R5And R6In the case of a chain alkyl group, the chain alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group. R5And R6In the case of a chain alkyl group, the number of carbon atoms in the chain alkyl group is preferably 1 to 20, more preferably 1 to 6. As R5And R6Specific examples of the chain alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, and sec-butylPentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, n-decyl, isodecyl and the like. In addition, R5And R6In the case of a chain alkyl group, the chain alkyl group may contain an ether bond (-O-) in the carbon chain. Examples of the chain alkyl group having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.
R5And R6In the case of a cyclic hydrocarbon group, the cyclic hydrocarbon group may be an aliphatic cyclic hydrocarbon group or an aromatic cyclic hydrocarbon group.
R5And R6In the case of an aromatic cyclic hydrocarbon group, the aromatic cyclic hydrocarbon group is preferably a phenyl group, a group in which a plurality of benzene rings are bonded via a carbon-carbon bond, or a group in which a plurality of benzene rings are condensed. When the aromatic cyclic hydrocarbon group is a phenyl group or a group in which a plurality of benzene rings are bonded or condensed, the number of rings of the benzene ring contained in the aromatic cyclic hydrocarbon group is not particularly limited, but is preferably 3 or less, more preferably 2 or less, and particularly preferably 1. Preferable specific examples of the aromatic cyclic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, and the like.
R5And R6In the case of the alicyclic hydrocarbon group, the alicyclic hydrocarbon group may be monocyclic or polycyclic. The number of carbon atoms of the aliphatic cyclic hydrocarbon group is not particularly limited, but is preferably 3 to 20, and more preferably 3 to 10. Examples of the monocyclic cyclic hydrocarbon group include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, norbornyl group, isobornyl group, tricyclononyl group, tricyclodecyl group, tetracyclododecyl group, and adamantyl group.
R5And R6In the case of a heteroaryl group, the heteroaryl group is a 5-or 6-membered monocyclic ring containing 1 or more N, S, O atoms, or a heteroaryl group in which the monocyclic rings are fused with each other or the monocyclic ring is fused with a benzene ring. When the heteroaryl group is a condensed ring, the number of rings is 3 or less. As constituting the heteroaryl groupExamples of the heterocyclic ring of (a) include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline and the like.
R5And R6May be bonded to each other to form a spiro ring. Comprising R5And R6The group forming the spiro ring is preferably a cycloalkylene group. R5And R6When bonded to form a cycloalkylene group, the spiro ring constituting the cycloalkylene group is preferably a 5-to 6-membered ring, and more preferably a 5-membered ring.
R5And R6When the group to which the bond is formed is a cycloalkylene group, the cycloalkylene group may be fused with 1 or more other rings. Examples of the ring which may be fused with a cycloalkylene group include a benzene ring, a naphthalene ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, and the like.
R7In the case of an organic group, it may be selected from various organic groups within a range not to impair the object of the present invention. As R7Preferable examples of the organic group include alkyl groups having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; a C2-7 saturated aliphatic acyl group; an alkoxycarbonyl group having 2 to 7 carbon atoms; a saturated aliphatic acyloxy group having 2 to 7 carbon atoms; a phenyl group; a naphthyl group; a benzoyl group; a naphthoyl group; benzoyl substituted with a group selected from alkyl having 1 to 6 carbon atoms, morpholin-1-yl, piperazin-1-yl, and phenyl; a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms; a dialkylamino group having an alkyl group having 1 to 6 carbon atoms; morpholin-1-yl; piperazin-1-yl; halogen; a nitro group; a cyano group.
R7Among them, benzoyl is preferred; a naphthoyl group; benzoyl substituted with a group selected from alkyl having 1 to 6 carbon atoms, morpholin-1-yl, piperazin-1-yl, and phenyl; nitro, more preferably benzoyl; a naphthoyl group;2-methylphenylcarbonyl; 4- (piperazin-1-yl) phenylcarbonyl; 4- (phenyl) phenylcarbonyl.
In addition, n is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1. When n is 1, R7The position of the bond is preferably relative to R7The bonding site of the bonded phenyl group to the atom A is para.
A is preferably S.
R8May be selected from various organic groups within a range not hindering the object of the present invention. As R8Preferable examples of the (B) include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a saturated aliphatic acyl group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoyl group which may have a substituent, a naphthyloxycarbonyl group which may have a substituent, a naphthylalkyl group having 11 to 20 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, and a heterocyclic carbonyl group which may have a substituent.
R8Among them, preferred is an alkyl group having 1 to 20 carbon atoms, more preferred is an alkyl group having 1 to 6 carbon atoms, and particularly preferred is an ethyl group.
As R7Or R8The substituents when the phenyl group, naphthyl group and heterocyclic group contained in (1) further have a substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a saturated aliphatic acyl group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, a cyano group and the like. R7Or R8The number of the substituents in the case where the phenyl group, naphthyl group and heterocyclic group contained in (1) further have a substituent is not particularly limited as long as the object of the present invention is not impaired, and is preferably 1 to 4. R7Or R8Wherein the heterocyclic group has a plurality of substitutionsThe plural substituents in the group may be the same or different.
R9And R4The same applies.
The compound represented by the formula (a-1) can be synthesized, for example, according to the following scheme (scheme)1 when m is 0. In scheme 1, a compound represented by the following formula (1-1) is used as a starting material. For example, R1In the case of the group represented by the formula (a-2), a fluorene derivative represented by the following formula (1-1-1) is used as a raw material in the scheme 1. R4In the case of a nitro group or a 1-valent organic group, the fluorene derivative represented by formula (1-1-1) can be synthesized using R by a known method5And R6Introduction of substituent R into fluorene derivative obtained by substitution of 9-position4And obtaining the compound. For with R5And R6With respect to the fluorene derivative obtained by substituting the 9-position, for example, when R is5And R6When alkyl, it can be obtained by: as described in Japanese patent application laid-open No. H06-234668, fluorene is reacted with an alkylating agent in an aprotic polar organic solvent in the presence of an alkali metal hydroxide. Furthermore, 9-alkyl-substituted fluorenes can be obtained by adding an alkylating agent such as an alkyl halide, an aqueous solution of an alkali metal hydroxide, and a phase transfer catalyst such as tetrabutylammonium iodide and potassium tert-butoxide to an organic solvent solution of the fluorene to carry out an alkylation reaction.
By using a halogenated carbonyl compound represented by the formula (1-2) and carrying out Friedel-Crafts reaction, the compound represented by the formula (1-1) is acylated to obtain a ketone compound represented by the formula (1-3). In the formula (1-2), Hal is a halogen atom. R1The position on the aromatic ring contained in (1) to be acylated by the compound represented by the formula (1-2) can be selected by the following method: the conditions of Friedel-crafts reaction are appropriately changed, or protection and deprotection are performed on the aromatic ring at a position other than the position acylated by the compound represented by the formula (1-2).
Then, the ketone compound represented by the formula (1-3) thus obtained is oximated with hydroxylamine to obtain an oxime compound represented by the following formula (1-4). An oxime compound of the formula (1-4) is reacted with a compound represented by the following formula (1-5)Acid anhydride ((R)3CO)2O) or an acid halide (R) represented by the following formula (1-6)3COHal, Hal is a halogen atom. ) The reaction gave a compound represented by the following formula (1-7).
In the formulae (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) and (1-1-1), R is1、R2、R3、R4、R5And R6The same as in the case of the formula (a-1).
< flow scheme 1>
[ chemical formula 6]
The compound represented by the formula (a-1), wherein m is 1, can be synthesized, for example, according to the following scheme 2. In scheme 2, a compound represented by the following formula (2-1) is used as a starting material. The compound represented by the formula (2-1) can be obtained by acylating the compound represented by the formula (1-1) by a Friedel-crafts reaction in the same manner as in the scheme 1. Reacting a nitrite (RONO, R is an alkyl group having 1 to 6 carbon atoms) represented by the following formula (2-2) with a compound represented by the formula (2-1) in the presence of hydrochloric acid to obtain a ketoxime compound represented by the following formula (2-3). Next, a ketoxime compound represented by the following formula (2-3) and an acid anhydride ((R) represented by the following formula (2-4) are reacted3CO)2O) or an acid halide (R) represented by the following formula (2-5)3COHal, Hal is a halogen atom. ) The reaction gave a compound represented by the following formula (2-6). In the following formulae (2-1), (2-3), (2-4), (2-5) and (2-6), R1、R2And R3The same as in the case of the formula (a-1).
When m is 1, the following tendency is present: the generation of impurities in a cured product formed using a curable composition containing a compound represented by the formula (a-1) can be further reduced.
< flow chart 2>
[ chemical formula 7]
Preferred specific examples of the compound represented by the formula (a-1) include the following compounds.
[ chemical formula 8]
[ chemical formula 9]
[ chemical formula 10]
[ chemical formula 11]
[ chemical formula 12]
[ chemical formula 13]
[ chemical formula 14]
The content of the photopolymerization initiator (a) is preferably 0.1 to 90 parts by mass, and more preferably 1 to 80 parts by mass, based on 100 parts by mass of the total solid components of the curable composition. (A) When the content of the photopolymerization initiator is within the above range, the curable composition according to the present invention is likely to be a curable composition having more excellent sensitivity.
< B multifunctional acrylate Compound >
The multifunctional acrylate compound (B) is not particularly limited as long as it contains at least 1 selected from the group consisting of a siloxane bond, an aromatic ring and a crosslinked saturated ring. (B) The polyfunctional acrylate compound contributes to improvement in bendability, toughness and surface hardness of the hard coat layer obtained from the curable composition of the present invention. (B) The polyfunctional acrylate compound may be used singly or in combination of 2 or more. (B) The multifunctional acrylate compound may be a low molecular compound, an oligomer and/or a polymer having a specific repeating unit, or a combination thereof.
Examples of the (B) polyfunctional acrylate compound include (B) polyfunctional acrylate compounds containing a polyfunctional acrylate compound having a siloxane bond; the (B) polyfunctional acrylate compound containing a polyfunctional acrylate compound containing at least 1 selected from an aromatic ring and a crosslinked saturated ring preferably contains, from the viewpoint of easily improving the characteristics of the obtained hard coat layer: a multifunctional acrylate compound having a siloxane bond, and a multifunctional acrylate compound having at least 1 selected from an aromatic ring and a crosslinked saturated ring.
[ polyfunctional acrylate Compound having siloxane bond ]
The multifunctional acrylate compound having a siloxane bond does not contribute much to the effect of improving the bendability and suppressing the curing shrinkage (reducing the curling property) of the obtained hard coat layer, but contributes greatly to the improvement of the surface hardness of the hard coat layer. Examples of the multifunctional acrylate compound having a siloxane bond include polysilsesquioxane (polysilsequioxane) compounds having 2 or more (meth) acryloyl groups. In particular, from the viewpoint of more easily improving the surface hardness of the obtained hard coat layer, the polysilsesquioxane compound is preferably a cage-type polysilsesquioxane compound containing 2 or more (meth) acryloyl groups.
Examples of the polysilsesquioxane compound include a cage-type polysilsesquioxane represented by the following formula.
[RSiO3/2]n
(wherein R is independently a (meth) acryloyl group-or carboxyl group-containing group, n is 8, 10, 12, or 14, wherein 2 or more R's are a (meth) acryloyl group.)
Examples of the carboxyl group-containing group include a 1-valent group represented by-X-B-Y-COOH.
X represents a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group, or-R5-NH-R6- (wherein R5 and R6 represent alkylene groups having 1 to 3 carbon atoms; R5 and R6 may be the same or different), Y represents a group having a valence of 2 generated by removing 1 hydrogen atom from each of 2 ring carbon atoms from an aromatic ring group or an alicyclic group, or an alkylene group having a valence of 1 to 4 carbon atoms which may have a branch and/or a double bond, and B represents-NHCO-or-CONH-. Wherein, X and/or Y may have at least 1 kind of group selected from (meth) acryl group, vinyl group and epoxy group as a substituent.
Specific examples of the alkylene group having 1 to 6 carbon atoms in X include methylene, ethylene, propylene, butylene, and the like. The arylene group in X preferably has 6 to 10 carbon atoms. Examples of such arylene groups include phenylene (ortho-, meta-, or equivalent), naphthylene (1, 4-, 1, 5-, 2, 6-, etc.), and the like. Specific examples of-R5-NH-R6-in the above X include-CH2-NH-CH2-、-(CH2)2-NH-(CH2)2-、-(CH2)3-NH-(CH2)3-、-CH2-NH-(CH2)2-、-(CH2)2-NH-CH2-、-(CH2)2-NH-(CH2)3-、-(CH2)3-NH-(CH2)2-、-CH2-NH-(CH2)3-、-(CH2)3-NH-CH2-and the like.
Examples of the aromatic ring in Y include aromatic rings having 6 to 10 carbon atoms (e.g., benzene ring, naphthalene ring, tolyl group, xylyl group, etc.) which may have a substituent having 1 to 2 carbon atoms. Examples of the alicyclic group in Y include alicyclic groups having 5 to 10 carbon atoms (for example, monocyclic cycloalkyl groups, monocyclic cycloalkenyl groups, 2-cyclic alkyl groups, cagelike alkyl groups, and the like are included, and specific examples thereof include cyclopentane rings, cyclohexane rings, cycloheptane rings, cyclooctane rings, cyclononane rings, cyclodecane rings, dicyclopentadiene rings, norbornane rings, norbornene rings, cubane (cubane) rings, and basketball (basketane) rings). Specific examples of the alkylene group having 1 to 4 carbon atoms which may have a branch and/or a double bond in Y include an alkylene group such as a methylene group, an ethylene group, a propylene group, a vinylene group, a (2-octenyl) ethylene group, a (2, 4, 6-trimethyl-2-nonenyl) ethylene group, an alkylene group having a double bond, and an alkylene group having a branch having 1 to 9 carbon atoms.
[ polyfunctional acrylate Compound containing at least 1 selected from aromatic Ring and crosslinked saturated Ring ]
The polyfunctional acrylate compound containing at least 1 selected from an aromatic ring and a crosslinked saturated ring contributes moderately to the effect of improving the surface hardness of the obtained hard coat layer, but greatly contributes to improvement of the bendability of the hard coat layer and suppression of curing shrinkage (reduction of curling properties) by the synergistic effect of a rigid portion skeleton such as an aromatic ring and/or a crosslinked saturated ring and a soft portion skeleton such as an alkylene group (e.g., methylene group, ethylene group, etc.), an ether bond, and/or a urethane bond.
Examples of the aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a furan ring, a pyrrole ring, an imidazole ring, a thiophene ring, a phosphole (phosphole) ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a tetrazine ring, a benzofuran ring, an isobenzofuran ring, an indole ring, an isoindole ring, a benzothiophene ring, a phenylphosphole (benzophosphole) ring, a benzimidazole ring, a purine ring, an indazole ring, a benzoxazole ring, a benzisoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, an isocyanurate ring and the like, and from the viewpoint of bendability, curl resistance and the like of the obtained hard coat layer, an isocyanurate ring, a fluorene ring and a triazine ring are preferable.
Examples of the crosslinked saturated ring include norbornane ring, isobornane ring, adamantane ring, tricyclodecane ring, tetracyclododecane ring, and the like, and the tricyclodecane ring is preferable from the viewpoint of flexibility, curl resistance, and the like of the obtained hard coat layer.
The content of the (B) polyfunctional acrylate compound is preferably 10 to 99.9 parts by mass, more preferably 20 to 99 parts by mass, relative to 100 parts by mass of the total solid components of the curable composition. (B) When the content of the polyfunctional acrylate compound is in the above range, the hard coating layer obtained from the curable composition of the present invention tends to have more excellent bendability, toughness, and surface hardness.
< other ingredients >
The curable composition according to the present invention may contain various additives as necessary. Specifically, the solvent, sensitizer, curing accelerator, photocrosslinking agent, photosensitizer, dispersion aid, filler, adhesion promoter, antioxidant, ultraviolet absorber, deflocculant, thermal polymerization inhibitor, defoaming agent, surfactant and the like may be mentioned.
Examples of the solvent usable in the curable composition according to the present invention include (poly) alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-propyl ether, diethylene glycol n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc.; (poly) alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; alkyl lactate esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl glycolate, methyl 2-hydroxy-3-methylbutyrate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl 2-oxobutyrate and other esters; aromatic hydrocarbons such as toluene and xylene; amides such as N-methylpyrrolidone, N-dimethylformamide and N, N-dimethylacetamide. These solvents may be used alone, or 2 or more of them may be used in combination.
Among the above solvents, propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, and 3-methoxybutyl acetate are preferred because they exhibit excellent solubility in the above-mentioned component (a) and component (B), and propylene glycol monomethyl ether acetate and 3-methoxybutyl acetate are particularly preferably used. The amount of the solvent to be used may be appropriately determined depending on the use of the curable composition, and examples thereof include: the amount of the curable composition is about 50 to 900 parts by mass per 100 parts by mass of the total solid components of the curable composition. In the present invention, when a solvent is used, the film thickness tends to be easily controlled. This tendency is particularly remarkable in the case where a thin film is required. When the component (B) is a solid at room temperature, a solvent is preferably used in the present invention.
Examples of the thermal polymerization inhibitor that can be used in the curable composition according to the present invention include hydroquinone, hydroquinone monoethyl ether, and the like. Further, examples of the defoaming agent include silicone compounds, fluorine compounds, and the like; examples of the surfactant include anionic, cationic and nonionic compounds.
[ Process for producing curable composition ]
The curable composition according to the present invention can be prepared by mixing all the above components with a mixer. When the curable composition to be produced does not contain an insoluble component such as a filler, filtration may be performed using a filter so that the curable composition becomes uniform.
Method for producing cured product
The method for producing a cured product according to the present invention comprises the steps of:
a step of forming a curable composition film using the curable composition according to the present invention; and
and exposing the curable composition film to light.
The cured product produced by the production method may be patterned as necessary.
Examples of the method for forming a curable composition film using the curable composition according to the present invention include the following methods: the curable composition is applied to a substrate using a contact transfer type coating apparatus such as a roll coater, reverse coater, or bar coater, a non-contact type coating apparatus such as a spin coater or curtain flow coater. The substrate is not particularly limited, and examples thereof include a substrate described later.
The formed curable composition film may be dried as necessary. The drying method is not particularly limited, and for example, the following methods are exemplified: (1) drying the mixture for 60 to 120 seconds by using a heating plate, for example, at a temperature of 80 to 120 ℃, preferably 90 to 100 ℃; (2) standing at room temperature for several hours to several days; (3) a method of drying the mixture by placing the mixture in a hot air heater or an infrared heater for several tens of minutes to several hours; and so on.
Next, the curable composition film is irradiated with an active energy ray such as an ultraviolet ray or an excimer laser beam, and exposed. For exposure, e.g.The exposure can be performed position-selectively by a method of performing exposure through a negative mask, or by full-surface exposure. When the entire surface is exposed, for example, the curable composition film may be continuously irradiated with the active energy ray in an in-line process while the film substrate on which the curable composition film is formed is wound in a line (1 ine). The dose of the energy ray to be irradiated varies depending on the composition of the curable composition, and is preferably 40 to 200mJ/cm, for example2Left and right. The light source is not particularly limited, and examples thereof include a high-pressure mercury lamp and an LED, and an LED is preferable from the viewpoint of energy saving and environmental load reduction. In the exposure with the LED, as the usable wavelength, for example, the wavelength in the UV region of 365 to 405nm, more specifically 385nm, 395nm, 405nm, etc. can be given. In general, the amount of energy radiation emitted from the LED is likely to be reduced. However, since the curable composition according to the present invention contains (a) a photopolymerization initiator and is excellent in sensitivity, it can be sufficiently cured even when exposed to light using an LED as a light source, and a cured product having good characteristics can be effectively obtained. As described above, the curable composition of the present invention is excellent in sensitivity, and therefore, by using the curable composition of the present invention, a hard coat material can be efficiently produced, and as a result, productivity of a display device such as a liquid crystal display panel can be improved.
When the curable composition film is exposed to light with position selectivity, a pattern having a desired shape can be formed by developing the exposed film with a developer. The developing method is not particularly limited, and for example, a dipping method, a spraying method, or the like can be used. The developer is appropriately selected depending on the composition of the curable composition. When the curable composition contains an alkali-soluble component such as an alkali-soluble resin, an organic developer such as monoethanolamine, diethanolamine or triethanolamine, or an aqueous solution of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia or a quaternary ammonium salt can be used as the developer.
Next, post-baking (post cake) is preferably performed at about 200 to 250 ℃ for the developed pattern.
The cured product obtained by the method for producing a cured product according to the present invention can be suitably used, for example, as a hard coat layer in a hard coat material.
Hard coating Material
The hard coat material according to the present invention comprises a substrate and a hard coat layer formed on the substrate by using the curable composition according to the present invention.
The substrate is not particularly limited, and a substrate known as a substrate for a hard coat material can be used. Specific examples thereof include film substrates such as triacetyl cellulose (TAC), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), Polyamide (PA), polymethyl methacrylate (PMMA), nylon (Ny), polyether sulfone (PES), polyvinyl chloride (PVC), polypropylene (PP), and Polycarbonate (PC); glass substrates, and the like. Among them, a film substrate is preferable, and TAC film, PC film, and PET film are more preferable.
The hard coating material of the present invention can be produced by: first, a curable composition film is formed using the curable composition according to the present invention, and then the curable composition film is exposed to light. The formation and exposure of the curable composition film are the same as in the case of the method for producing a cured product according to the present invention. The film thickness of the hard coat layer is preferably 1 to 10 μm.
Image display device
The image display device according to the present invention includes the hard coat material according to the present invention. Examples of the image display device include a liquid crystal display, a plasma display, a CRT display, an EL display, an organic EL display, a field emission display, and the like, and the hard coat material according to the present invention may be bonded to the display surface or the wiring protective layer thereof.
Examples
The present invention will be described in more detail with reference to the following examples, but the scope of the present invention is not limited to these examples.
Examples 1 to 12 and comparative examples 1 to 8
As shown in table 1, (a) a photopolymerization initiator, (B1) a multifunctional acrylate compound having a siloxane bond, (B2) a multifunctional acrylate compound containing at least 1 selected from an aromatic ring and a crosslinked saturated ring, and (B3) another acrylate compound were uniformly mixed to obtain a solvent-free curable composition. The parenthesized values in Table 1 represent the amounts of the respective components (unit: parts by mass).
Compound 1: a photopolymerization initiator represented by the following chemical formula on the left side of the first row
Compound 2: a photopolymerization initiator represented by the following chemical formula on the right side of the first line
Compound 3: a photopolymerization initiator represented by the following chemical formula in the second row
[ chemical formula 15]
Irg 819: a photopolymerization initiator represented by the following left chemical formula
Irg 184: a photopolymerization initiator represented by the following intermediate chemical formula
OXE 01: a photopolymerization initiator represented by the following right chemical formula
[ chemical formula 16]
Silsesquioxane 1: r19～R26Silsesquioxane represented by the following left chemical formula and containing all acryloyloxy groups
Silsesquioxane 2: r19～R2630 mol% of (B) is a group represented by the following right-hand chemical formula, R19～R2670 mol% of (a) silsesquioxane represented by the following left chemical formula
[ chemical formula 17]
Tricyclodecane series: the compound represented by the following formula on the left side of the first line
Isocyanuric acid system 1: the compounds represented by the following chemical formulae on the right side of the first line
A fluorene group: a compound represented by the following chemical formula in the second row
Isocyanuric acid system 2: x represents acryloyloxy group, and the third row of the compound represented by the formula
[ chemical formula 18]
[ method for producing film ]
The obtained curable composition was dropped onto a PET film having a thickness of 100 μm and applied by an applicator (applicator) to obtain a curable composition film. Then, the curable composition film was exposed to light using a high-pressure mercury lamp exposure machine (ORC) or an LED lamp (395 nm wavelength) to obtain a cured film having a thickness of 50 μm. The cured film was peeled from the PET film, and the following evaluation was performed. The results of these evaluations are shown in Table 1.
[ surface hardness ]
The pencil hardness of the cured film was measured in accordance with JIS K5600-5-4. The surface hardness was evaluated according to the following criteria.
◎ (very good), the pencil hardness is 7H or more.
○ (good), the pencil hardness is 4H to 6H.
X (bad): the pencil hardness is 3H or less.
[ transparency ]
The transmittance of the above-mentioned cured film at 400nm was measured using a transmittance meter MCPD (Otsuka Denshi Co., Ltd.). The transparency was evaluated according to the following criteria.
◎ (very good), the transmittance was 95% or more.
○ (good), the transmittance is more than 90% and less than 95%.
X (bad): the transmittance is less than 90%.
[ bendability and toughness ]
A stainless steel rod having a radius of n (unit: mm, n is an integer of 1 or more) is prepared. The cured film was wound around each prepared stainless steel rod. The stainless steel rod having the smallest radius among the stainless steel rods that could be wound without breaking the cured film was determined. The bending properties and toughness were evaluated according to the following criteria.
◎ (very preferred), the minimum radius is 2mm or less.
○ preferably, the minimum radius is 3 to 5 mm.
X (bad): the minimum radius is 6mm or more.
As is clear from table 1, the hard coat layer obtained from the curable composition of the present invention is excellent in flexibility, toughness, surface hardness and transparency, and can be suitably used as a hard coat material.
Claims (6)
1. A curable composition containing (A) a photopolymerization initiator and (B) a polyfunctional acrylate compound containing at least 1 selected from the group consisting of a siloxane bond, an aromatic ring and a crosslinked saturated ring,
the (A) photopolymerization initiator comprises a compound represented by the following formula (a-1):
chemical formula 1
R1Is a group represented by the following formula (a-2), a group represented by the following formula (a-3), or a group represented by the following formula (a-4), R2Is an organic radical of valency 1, R3A hydrogen atom, an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent, and m is 0 or 1;
chemical formula 2
R4To hydrogen atomsA nitrile group, or an organic group having a valence of 1, R5And R6Independently is a chain alkyl, cyclic hydrocarbyl, or heteroaryl group, R5And R6May be bonded to each other to form a spiro ring;
chemical formula 3
R7Independently is a 1-valent organic group, amino, halogen atom, nitro or cyano, A is S or O, and n is an integer of 0-4;
chemical formula 4
R8Is an organic radical of valency 1, R9Is a hydrogen atom, a nitro group, or a 1-valent organic group.
2. The curable composition according to claim 1, wherein the (B) polyfunctional acrylate compound comprises a polyfunctional acrylate compound having a siloxane bond.
3. The curable composition according to claim 2, wherein the siloxane bond-containing multifunctional acrylate compound is a polysilsesquioxane compound containing 2 or more (meth) acryloyl groups.
4. The curable composition according to claim 2, wherein the (B) multifunctional acrylate compound further comprises: a polyfunctional acrylate compound containing at least 1 selected from an aromatic ring and a crosslinked saturated ring.
5. A method for producing a cured product, comprising the steps of:
a step of forming a curable composition film using the curable composition according to claim 1; and
and exposing the curable composition film.
6. A hard coat material comprising a substrate and a hard coat layer formed on the substrate by using the curable composition according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015-121983 | 2015-06-17 | ||
| JP2015121983A JP6602062B2 (en) | 2015-06-17 | 2015-06-17 | Curable composition, method for producing cured product, and hard coat material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106256837A CN106256837A (en) | 2016-12-28 |
| CN106256837B true CN106256837B (en) | 2020-04-10 |
Family
ID=57714196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610420826.2A Active CN106256837B (en) | 2015-06-17 | 2016-06-13 | Curable composition, method for producing cured product, and hard coating material |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP6602062B2 (en) |
| KR (1) | KR102503973B1 (en) |
| CN (1) | CN106256837B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101788399B1 (en) * | 2015-09-23 | 2017-10-19 | (주)경인양행 | Oxime ester compound having improved heat stability, photopolymerization initiator and photoresist composition comprising the same |
| JP6677047B2 (en) * | 2016-03-30 | 2020-04-08 | 三菱ケミカル株式会社 | Alicyclic polyfunctional (meth) acrylate compounds |
| KR102252723B1 (en) * | 2017-07-14 | 2021-05-17 | 후지필름 가부시키가이샤 | Surface-modified inorganic nitride, composition, thermally conductive material, device with thermally conductive layer |
| WO2019013323A1 (en) * | 2017-07-14 | 2019-01-17 | 富士フイルム株式会社 | Surface-modified inorganic nitride, composition, thermally conductive material, device provided with thermally conductive layer |
| JP6876799B2 (en) | 2017-07-14 | 2021-05-26 | 富士フイルム株式会社 | Surface-modified inorganic nitrides, compositions, heat conductive materials, devices with heat conductive layers |
| CN111918769B (en) * | 2018-03-30 | 2022-06-24 | 富士胶片株式会社 | Hard coat film, article having hard coat film, image display device, and method for producing hard coat film |
| CN113853302B (en) * | 2019-05-17 | 2024-01-02 | 富士胶片株式会社 | Hard coat film, article provided with hard coat film, and image display device |
| WO2020235383A1 (en) * | 2019-05-17 | 2020-11-26 | 富士フイルム株式会社 | Resin composition, hard coating film and polyorganosilsesquioxane |
| WO2021060055A1 (en) * | 2019-09-27 | 2021-04-01 | 富士フイルム株式会社 | Composition for hard coat layer formation, hard coat film, method for producing hard coat film, and article including hard coat film |
| CN114075398A (en) * | 2020-08-21 | 2022-02-22 | 广东华润涂料有限公司 | Coating composition and coated article including coating layer formed by coating composition |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005215147A (en) * | 2004-01-28 | 2005-08-11 | Fuji Photo Film Co Ltd | Polymerizable composition |
| JP2006241406A (en) * | 2005-03-07 | 2006-09-14 | Fuji Photo Film Co Ltd | Ink composition, inkjet recording method, printed article, method for producing planographic printing plate and planographic printing plate |
| JP5117002B2 (en) * | 2006-07-10 | 2013-01-09 | 富士フイルム株式会社 | Photocurable composition and pattern forming method using the same |
| JP4899100B2 (en) * | 2007-05-29 | 2012-03-21 | ナガセケムテックス株式会社 | Photosensitive composition |
| CN102015633B (en) * | 2008-04-25 | 2014-08-06 | 三菱化学株式会社 | Ketoxime ester compound and use thereof |
| JP2009286976A (en) * | 2008-05-30 | 2009-12-10 | Fujifilm Corp | Polymerizable liquid crystal composition, optically anisotropic film, optical element and liquid crystal display device |
| KR101678028B1 (en) * | 2009-06-17 | 2016-11-21 | 토요잉크Sc홀딩스주식회사 | Oxime ester compound, radical polymerization initiator, polymerizable composition, negative resist and image pattern |
| TWI475006B (en) * | 2009-09-08 | 2015-03-01 | Nippon Steel & Sumikin Chem Co | Photopolymerization initiator and photosensitive composition |
| JP5515714B2 (en) * | 2009-12-16 | 2014-06-11 | Ｊｓｒ株式会社 | Coloring composition, color filter and color liquid crystal display element |
| JP2011170334A (en) * | 2010-01-20 | 2011-09-01 | Fujifilm Corp | Black curable composition for wafer-level lens, and wafer-level lens |
| JP2013522687A (en) * | 2010-03-22 | 2013-06-13 | エルジー・ケム・リミテッド | Photocurable and thermosetting resin composition, and dry film solder resist |
| JP5222922B2 (en) * | 2010-10-12 | 2013-06-26 | 富士フイルム株式会社 | Pattern forming method, pattern forming material, and photosensitive film, pattern film, low refractive index film, optical device, and solid-state imaging device using the same |
| CN102477252A (en) * | 2010-11-29 | 2012-05-30 | Jsr株式会社 | Laminated film for hard coating forming, film coil and curing composition for hard coating forming |
| HUE048405T2 (en) * | 2011-07-11 | 2020-07-28 | Tokuyama Corp | Photochromic curable composition |
| JP5890297B2 (en) * | 2011-12-22 | 2016-03-22 | 東京応化工業株式会社 | Photosensitive resin composition, color filter and display device using the same, oxime ester compound, and photopolymerization initiator |
| JP2013195550A (en) | 2012-03-16 | 2013-09-30 | Toppan Printing Co Ltd | Optical film and optical display device |
| JP6127130B2 (en) * | 2012-05-03 | 2017-05-10 | コリア リサーチ インスティテュート オブ ケミカル テクノロジー | Novel oxime ester fluorene compound, photopolymerization initiator containing the same, and photoresist composition |
| KR20140077246A (en) * | 2012-12-12 | 2014-06-24 | 동우 화인켐 주식회사 | A colored curable resin composition, color filter and display device |
| CN103293855B (en) * | 2013-05-20 | 2015-12-23 | 常州强力先端电子材料有限公司 | A kind of esters of acrylic acid Photocurable composition |
| JP5890457B2 (en) * | 2013-08-05 | 2016-03-22 | 東京応化工業株式会社 | Pigment dispersion, photosensitive resin composition containing the same, and dispersion aid |
| JP6339346B2 (en) * | 2013-11-05 | 2018-06-06 | 太陽インキ製造株式会社 | Curable composition for printed wiring board, cured coating film using the same, and printed wiring board |
| JP6400289B2 (en) * | 2013-12-24 | 2018-10-03 | 日立化成株式会社 | Base material for touch panel with cured film and method for producing the same, photosensitive element and touch panel |
-
2015
- 2015-06-17 JP JP2015121983A patent/JP6602062B2/en active Active
-
2016
- 2016-06-09 KR KR1020160071816A patent/KR102503973B1/en active IP Right Grant
- 2016-06-13 CN CN201610420826.2A patent/CN106256837B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20160149147A (en) | 2016-12-27 |
| JP6602062B2 (en) | 2019-11-06 |
| JP2017008134A (en) | 2017-01-12 |
| CN106256837A (en) | 2016-12-28 |
| KR102503973B1 (en) | 2023-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106256837B (en) | Curable composition, method for producing cured product, and hard coating material | |
| KR102190911B1 (en) | Photosensitive composition and compound | |
| KR102441729B1 (en) | Coloring agent dispersion, photosensitive resin composition, cured product, organic el element, method for forming pattern, and method for producing photosensitive resin composition | |
| KR101963931B1 (en) | Black photosensitive resin composition, black matrix and image display device comprising thereof | |
| JP6195590B2 (en) | Photosensitive composition, pattern forming method, cured film, insulating film, and display device | |
| JP2017142345A (en) | Photosensitive resin composition for black column spacers, black column spacer, display device, and method of forming black column spacer | |
| JP7313136B2 (en) | Photosensitive resin composition, method for producing patterned cured film, and patterned cured film | |
| KR102451298B1 (en) | Photosensitive composition and method for forming cured film | |
| KR20200010550A (en) | Photosensitive composition, method for producing photosensitive composition, photopolymerization initiator, and method for preparing photopolymerization initiator | |
| KR102568123B1 (en) | Photosensitive composition, and photopolymerization initiator used therefor | |
| CN104102091B (en) | Composition for forming transparent insulating film | |
| JP2014119739A (en) | Colored composition, color filter, display element, and polysiloxane | |
| CN113391519A (en) | Photosensitive composition, transparent body, and method for producing transparent body | |
| JP2017049566A (en) | Photosensitive composition, method for producing photosensitive composition, method for forming film using photosensitive composition, method for suppressing thickening of photosensitive composition at the time of storage, photopolymerization initiator, and method for producing photopolymerization initiator | |
| KR20210126512A (en) | Photosensitive composition, manufacturing method for patterned cured film, and patterned cured film | |
| JP6436838B2 (en) | Photosensitive resin composition | |
| KR102429609B1 (en) | Photosensitive resin composition | |
| TWI664500B (en) | Black photosensitive resin composition and uses thereof | |
| JP6437050B2 (en) | Photosensitive composition, pattern forming method, cured film, insulating film, and display device | |
| JP2023034976A (en) | Colored photosensitive resin composition, and method for producing patterned cured product | |
| JP2022059983A (en) | Black photosensitive resin composition, method for producing patterned cured product, patterned cured product, and black matrix | |
| JP2016186572A (en) | Photosensitive resin composition | |
| JP2022059982A (en) | Black photosensitive resin composition, method for producing patterned cured product, patterned cured product, and black matrix | |
| CN114761498A (en) | Photosensitive ink composition, cured product, display panel, and method for producing cured product | |
| CN114761497A (en) | Photosensitive ink composition, cured product, display panel, and method for producing cured product |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |