WO2019077913A1 - 着色組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 - Google Patents
着色組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 Download PDFInfo
- Publication number
- WO2019077913A1 WO2019077913A1 PCT/JP2018/033764 JP2018033764W WO2019077913A1 WO 2019077913 A1 WO2019077913 A1 WO 2019077913A1 JP 2018033764 W JP2018033764 W JP 2018033764W WO 2019077913 A1 WO2019077913 A1 WO 2019077913A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compound
- coloring composition
- mass
- pigment
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 230
- -1 color filter Substances 0.000 title claims abstract description 177
- 238000003384 imaging method Methods 0.000 title claims abstract description 22
- 239000007787 solid Substances 0.000 title abstract description 22
- 239000000049 pigment Substances 0.000 claims abstract description 217
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 44
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 150000001450 anions Chemical class 0.000 claims abstract description 29
- 238000004040 coloring Methods 0.000 claims description 163
- 229910052751 metal Inorganic materials 0.000 claims description 159
- 239000002184 metal Substances 0.000 claims description 159
- 239000003999 initiator Substances 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 239000003112 inhibitor Substances 0.000 claims description 15
- 230000007547 defect Effects 0.000 abstract description 36
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 132
- 229920005989 resin Polymers 0.000 description 85
- 239000011347 resin Substances 0.000 description 85
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 73
- 239000010408 film Substances 0.000 description 73
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 239000002253 acid Substances 0.000 description 49
- 125000004432 carbon atom Chemical group C* 0.000 description 48
- 239000003086 colorant Substances 0.000 description 47
- 238000000034 method Methods 0.000 description 47
- 125000005647 linker group Chemical group 0.000 description 45
- 239000000178 monomer Substances 0.000 description 45
- 229920000642 polymer Polymers 0.000 description 45
- 239000000243 solution Substances 0.000 description 45
- 125000001424 substituent group Chemical group 0.000 description 45
- 239000000975 dye Substances 0.000 description 42
- 125000002947 alkylene group Chemical group 0.000 description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 34
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 32
- 239000004094 surface-active agent Substances 0.000 description 29
- 239000002270 dispersing agent Substances 0.000 description 28
- 125000003118 aryl group Chemical group 0.000 description 27
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 27
- 229910052731 fluorine Inorganic materials 0.000 description 23
- 235000011118 potassium hydroxide Nutrition 0.000 description 23
- 239000011701 zinc Substances 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000010949 copper Substances 0.000 description 18
- 239000006185 dispersion Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 16
- 230000002378 acidificating effect Effects 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 239000006069 physical mixture Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000011161 development Methods 0.000 description 13
- 230000018109 developmental process Effects 0.000 description 13
- 125000000732 arylene group Chemical group 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- LCGWXMONLSJYQR-UHFFFAOYSA-N 5-[(2,4,6-trioxo-1,3-diazinan-5-yl)diazenyl]-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1N=NC1C(=O)NC(=O)NC1=O LCGWXMONLSJYQR-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 125000005529 alkyleneoxy group Chemical group 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 101100535673 Drosophila melanogaster Syn gene Proteins 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000004721 Polyphenylene oxide Substances 0.000 description 10
- 239000006087 Silane Coupling Agent Substances 0.000 description 10
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 10
- 150000004292 cyclic ethers Chemical group 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 101100043731 Caenorhabditis elegans syx-3 gene Proteins 0.000 description 9
- 101100368134 Mus musculus Syn1 gene Proteins 0.000 description 9
- 238000004220 aggregation Methods 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 125000005702 oxyalkylene group Chemical group 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000001312 dry etching Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 description 5
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 5
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 150000003751 zinc Chemical class 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- OAZDCJVJMWHYPJ-UHFFFAOYSA-N 5-diazonio-2,4-dioxo-1h-pyrimidin-6-olate Chemical compound [O-]C=1NC(=O)NC(=O)C=1[N+]#N OAZDCJVJMWHYPJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000005012 alkyl thioether group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000004832 aryl thioethers Chemical group 0.000 description 4
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 229910001453 nickel ion Inorganic materials 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920005672 polyolefin resin Polymers 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 125000005543 phthalimide group Chemical group 0.000 description 3
- 125000005544 phthalimido group Chemical group 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical compound C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 description 2
- LVYXPOCADCXMLP-UHFFFAOYSA-N 3-butoxy-n,n-dimethylpropanamide Chemical compound CCCCOCCC(=O)N(C)C LVYXPOCADCXMLP-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- 239000004115 Sodium Silicate Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 206010047571 Visual impairment Diseases 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001056 green pigment Substances 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000001007 phthalocyanine dye Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical group C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 2
- 239000001062 red colorant Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000003746 surface roughness Effects 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 229940124543 ultraviolet light absorber Drugs 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- VAAVXQPHWGURFL-UHFFFAOYSA-N (1,2-diethoxy-1,2,2-triphenylethyl)benzene Chemical compound C=1C=CC=CC=1C(C(OCC)(C=1C=CC=CC=1)C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 VAAVXQPHWGURFL-UHFFFAOYSA-N 0.000 description 1
- WSYHCVAGLRXMPP-UHFFFAOYSA-N (1,2-dimethoxy-1,2,2-triphenylethyl)benzene Chemical compound C=1C=CC=CC=1C(C(OC)(C=1C=CC=CC=1)C=1C=CC=CC=1)(OC)C1=CC=CC=C1 WSYHCVAGLRXMPP-UHFFFAOYSA-N 0.000 description 1
- ARJBLMGEDUINDZ-UHFFFAOYSA-N (1,2-diphenoxy-1,2,2-triphenylethyl)benzene Chemical compound C=1C=CC=CC=1C(C(OC=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)OC1=CC=CC=C1 ARJBLMGEDUINDZ-UHFFFAOYSA-N 0.000 description 1
- BUNYBPVXEKRSGY-ONEGZZNKSA-N (1e)-buta-1,3-dien-1-amine Chemical class N\C=C\C=C BUNYBPVXEKRSGY-ONEGZZNKSA-N 0.000 description 1
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- MRUDPRFGMHTPFJ-UHFFFAOYSA-N (3-oxobutan-2-ylideneamino) acetate Chemical compound CC(=O)ON=C(C)C(C)=O MRUDPRFGMHTPFJ-UHFFFAOYSA-N 0.000 description 1
- SKCKRZWCOYHBEC-UHFFFAOYSA-N (3-oxobutan-2-ylideneamino) benzoate Chemical compound CC(=O)C(C)=NOC(=O)C1=CC=CC=C1 SKCKRZWCOYHBEC-UHFFFAOYSA-N 0.000 description 1
- JFFCVOSCPLKMLG-UHFFFAOYSA-N (3-oxobutan-2-ylideneamino) propanoate Chemical compound CCC(=O)ON=C(C)C(C)=O JFFCVOSCPLKMLG-UHFFFAOYSA-N 0.000 description 1
- HQLZSJJJXHJANW-UHFFFAOYSA-N (3-oxopentan-2-ylideneamino) acetate Chemical compound CCC(=O)C(C)=NOC(C)=O HQLZSJJJXHJANW-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- TWDFSQNRBYNLAA-UHFFFAOYSA-N 1,1,2,2-tetraphenyl-2-triethylsilyloxyethanol Chemical compound OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](CC)(CC)CC)(C1=CC=CC=C1)C1=CC=CC=C1 TWDFSQNRBYNLAA-UHFFFAOYSA-N 0.000 description 1
- FZFFWZJDHRTEMQ-UHFFFAOYSA-N 1,1,2,2-tetraphenyl-2-trimethylsilyloxyethanol Chemical compound OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 FZFFWZJDHRTEMQ-UHFFFAOYSA-N 0.000 description 1
- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- XTNYHSVRWXRDFR-UHFFFAOYSA-N 1-[1,2-dimethoxy-1,2,2-tris(4-methylphenyl)ethyl]-4-methylbenzene Chemical compound COC(C(C1=CC=C(C=C1)C)(C1=CC=C(C=C1)C)OC)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C XTNYHSVRWXRDFR-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
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- PMOIEAKTNCGZAJ-UHFFFAOYSA-N 1-methoxy-4-[1,2,2-tris(4-methoxyphenyl)-1,2-diphenoxyethyl]benzene Chemical compound O(C1=CC=CC=C1)C(C(C1=CC=C(C=C1)OC)(C1=CC=C(C=C1)OC)OC1=CC=CC=C1)(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC PMOIEAKTNCGZAJ-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- KCCIQVUYNPMYSL-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxy-1,1,2,2-tetraphenylethanol Chemical compound OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 KCCIQVUYNPMYSL-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical class C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- DQYSALLXMHVJAV-UHFFFAOYSA-M 3-heptyl-2-[(3-heptyl-4-methyl-1,3-thiazol-3-ium-2-yl)methylidene]-4-methyl-1,3-thiazole;iodide Chemical compound [I-].CCCCCCCN1C(C)=CS\C1=C\C1=[N+](CCCCCCC)C(C)=CS1 DQYSALLXMHVJAV-UHFFFAOYSA-M 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- ACQVEWFMUBXEMR-UHFFFAOYSA-N 4-bromo-2-fluoro-6-nitrophenol Chemical compound OC1=C(F)C=C(Br)C=C1[N+]([O-])=O ACQVEWFMUBXEMR-UHFFFAOYSA-N 0.000 description 1
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- SYSPOOPLPCVGLD-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)OC(C(C=N)=O)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)OC(C(C=N)=O)C)C SYSPOOPLPCVGLD-UHFFFAOYSA-N 0.000 description 1
- 101100043727 Caenorhabditis elegans syx-2 gene Proteins 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- 102100029921 Dipeptidyl peptidase 1 Human genes 0.000 description 1
- 102100020751 Dipeptidyl peptidase 2 Human genes 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229910003317 GdCl3 Inorganic materials 0.000 description 1
- 101000793922 Homo sapiens Dipeptidyl peptidase 1 Proteins 0.000 description 1
- 101000931864 Homo sapiens Dipeptidyl peptidase 2 Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920002035 Pluronic® L 10 Polymers 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229920002359 Tetronic® Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- DPQRMIPRAHPPNE-UHFFFAOYSA-N [(1-oxo-1-phenylpropan-2-ylidene)amino] acetate Chemical compound CC(=O)ON=C(C)C(=O)C1=CC=CC=C1 DPQRMIPRAHPPNE-UHFFFAOYSA-N 0.000 description 1
- ZNZDJSGUWLGTLA-UHFFFAOYSA-N [(1-oxo-1-phenylpropan-2-ylidene)amino] benzoate Chemical compound C=1C=CC=CC=1C(=O)C(C)=NOC(=O)C1=CC=CC=C1 ZNZDJSGUWLGTLA-UHFFFAOYSA-N 0.000 description 1
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 1
- HIVQCJOGAHNXBO-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] propanoate Chemical compound CCC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C HIVQCJOGAHNXBO-UHFFFAOYSA-N 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- JGFLAAWSLCPCDY-UHFFFAOYSA-N benzene;cyclopenta-1,3-diene;iron Chemical class [Fe].C1C=CC=C1.C1=CC=CC=C1 JGFLAAWSLCPCDY-UHFFFAOYSA-N 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- RKTGAWJWCNLSFX-UHFFFAOYSA-M bis(2-hydroxyethyl)-dimethylazanium;hydroxide Chemical compound [OH-].OCC[N+](C)(C)CCO RKTGAWJWCNLSFX-UHFFFAOYSA-M 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- IWPATTDMSUYMJV-UHFFFAOYSA-N butyl 2-methoxyacetate Chemical compound CCCCOC(=O)COC IWPATTDMSUYMJV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 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 1
- 229960002887 deanol Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- WNIHNYUROPJCLW-UHFFFAOYSA-N ethyl 2-ethoxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OCC WNIHNYUROPJCLW-UHFFFAOYSA-N 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 description 1
- WHRLOJCOIKOQGL-UHFFFAOYSA-N ethyl 2-methoxypropanoate Chemical compound CCOC(=O)C(C)OC WHRLOJCOIKOQGL-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
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229910001009 interstitial alloy Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 150000002576 ketones Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 0.000 description 1
- XPIWVCAMONZQCP-UHFFFAOYSA-N methyl 2-oxobutanoate Chemical compound CCC(=O)C(=O)OC XPIWVCAMONZQCP-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- ZBOYHAZRFJBUEL-UHFFFAOYSA-N n-[2-(4-benzhydryloxypiperidin-1-yl)ethyl]-3-hydroxy-5-(pyridin-3-ylmethoxy)naphthalene-2-carboxamide Chemical compound C1=CC=C2C=C(C(=O)NCCN3CCC(CC3)OC(C=3C=CC=CC=3)C=3C=CC=CC=3)C(O)=CC2=C1OCC1=CC=CN=C1 ZBOYHAZRFJBUEL-UHFFFAOYSA-N 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 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
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UBVJBJKQDWCTRF-UHFFFAOYSA-N tert-butyl(dimethyl)azanium hydroxide Chemical compound [OH-].CC(C)([NH+](C)C)C UBVJBJKQDWCTRF-UHFFFAOYSA-N 0.000 description 1
- WRWQRNWWCINRPO-UHFFFAOYSA-N tert-butyl-[2-[tert-butyl(dimethyl)silyl]oxy-1,1,2,2-tetraphenylethoxy]-dimethylsilane Chemical compound C(C)(C)(C)[Si](OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)(C)C WRWQRNWWCINRPO-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- MPQVYFJXQMBTHQ-UHFFFAOYSA-N triethyl-(1,1,2,2-tetraphenyl-2-triethylsilyloxyethoxy)silane Chemical compound C(C)[Si](OC(C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](CC)(CC)CC)(C1=CC=CC=C1)C1=CC=CC=C1)(CC)CC MPQVYFJXQMBTHQ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WTKVMIIQXATOJO-UHFFFAOYSA-N trimethyl-(1,1,2,2-tetraphenyl-2-trimethylsilyloxyethoxy)silane Chemical compound C=1C=CC=CC=1C(C(O[Si](C)(C)C)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O[Si](C)(C)C)C1=CC=CC=C1 WTKVMIIQXATOJO-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/02—Azomethine-azo dyes
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B25/00—Quinophthalones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/108—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system characterised by a cyclammonium six-membered specific ring not mentioned hereafter, e.g. pyrimidinium, perimidinium, pyridazonium, oxazinium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/18—Monoazo compounds containing copper
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/22—Monoazo compounds containing other metals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- H01L27/146—
Definitions
- the present invention relates to a coloring composition. More particularly, it relates to colored compositions comprising metal azo pigments.
- the present invention also relates to a film using a coloring composition, a color filter, a solid-state imaging device, and an image display device.
- Color filters are used as key devices for displays and optical elements.
- the color filter usually has pixels (colored patterns) of three primary colors of red, green and blue, and plays a role of separating transmitted light into the three primary colors.
- Patent Documents 1 to 4 disclose inventions on metal azo pigments containing azobarbituric acid, two or more types of metal ions, and a melamine compound.
- the metal azo pigments described in Patent Documents 1 to 4 are considered to have improved coloring performance relative to metal azo pigments based on conventional metal complexes of nickel and azobarbituric acid. There is.
- the coloring composition may be used after being stored for a long time. Also, the coloring composition may be stored in a low temperature environment of 0 ° C. or less.
- the inventors of the present invention have intensively studied metal azo pigments containing azobarbituric acid, two or more types of metal ions, and a melamine compound. As a result, the colored composition containing the metal azo pigment is subjected to a low temperature environment. It was found that when stored for storage, the film was prone to defects.
- an object of the present invention is to provide a coloring composition capable of producing a film in which the occurrence of defects is suppressed even when the coloring composition is stored for a long time under a low temperature environment.
- Another object of the present invention is to provide a film, a color filter, a solid-state imaging device and an image display device using the coloring composition.
- R 1 and R 2 are each independently OH or NR 5 R 6
- R 5 to R 7 are each independently a hydrogen atom or an alkyl group.
- a ⁇ 2> metal azo pigment contains the said anion, the metal ion which contains Zn2 + and Cu2 + at least, and the said melamine compound.
- the coloring composition as described in any one of ⁇ 1>- ⁇ 4> whose melamine compound in ⁇ 5> metal azo pigment is a compound represented by following formula (II);
- R 11 to R 13 each independently represent a hydrogen atom or an alkyl group.
- the coloring composition as described in ⁇ 6> whose ⁇ 7> photoinitiator is an oxime compound.
- ⁇ 8> The coloring composition according to any one of ⁇ 1> to ⁇ 7>, containing 10 parts by mass or more of a compound having an ethylenically unsaturated bond group with respect to 100 parts by mass of the metal azo pigment.
- ⁇ 9> The colored composition according to any one of ⁇ 1> to ⁇ 8>, further comprising a polymerization inhibitor.
- ⁇ 10> The colored composition according to any one of ⁇ 1> to ⁇ 9>, further comprising a pigment derivative.
- ⁇ 12> The colored composition according to any one of ⁇ 1> to ⁇ 11>, which is for a solid-state imaging device.
- ⁇ 13> A film obtained from the coloring composition according to any one of ⁇ 1> to ⁇ 12>.
- ⁇ 14> A color filter having the film described in ⁇ 13>.
- the solid-state image sensor which has a film
- the image display apparatus which has a film
- the present invention it is possible to provide a coloring composition capable of producing a film in which the occurrence of defects is suppressed even when the coloring composition is stored for a long time under a low temperature environment. Moreover, the film
- a bright line spectrum of a mercury lamp far ultraviolet rays represented by an excimer laser, extreme ultraviolet rays (EUV light), actinic rays such as X-rays, electron beams and the like can be mentioned.
- EUV light extreme ultraviolet rays
- a numerical range represented using “to” means a range including the numerical values described before and after “to” as the lower limit value and the upper limit value.
- total solids refers to the total amount of all components of the composition excluding the solvent.
- (meth) acrylate represents both or either of acrylate and methacrylate
- (meth) acryl represents both or either of acrylic and methacryl
- Allyl represents both or any of allyl and methallyl
- (meth) acryloyl represents both or any of acryloyl and methacryloyl.
- step does not only mean an independent step, but if the intended function of that step is achieved even if it can not be clearly distinguished from other steps, this term include.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene conversion values measured by gel permeation chromatography (GPC).
- the coloring composition of the present invention is A metal azo pigment comprising at least one anion selected from an azo compound represented by the formula (I) and an azo compound having a tautomeric structure thereof, two or more types of metal ions, and a melamine compound; A compound having an ethylenically unsaturated bond group, And a solvent.
- the low temperature environment for example, -0 ° C or less, preferably -5 ° C or less, more preferably -10 ° C or less, still more preferably -15 ° C or less, still more preferably -20 ° C or less
- a film in which the occurrence of defects is suppressed can be produced.
- the mechanism by which such an effect is obtained is presumed to be by the following.
- the above-mentioned metal azo pigments tend to have low hardness, and it is presumed that, for example, when preparing a dispersion, some of the metal azo pigments are excessively refined, and as a result, the coloring composition is stored in excess.
- the finely divided metal azo pigment reaggregates.
- the content of the nickel ion (Ni 2+ ) in the metal azo pigment is small or when the metal azo pigment does not contain the nickel ion, it is estimated that the state is energetically unstable, and the metal azo pigment is It tends to reaggregate more easily.
- this metal azo pigment tends to promote reaggregation when the temperature at the time of storage of the coloring composition is low. In particular, in a low temperature environment of 0 ° C. or less, reaggregation of the metal azo pigment tends to be promoted.
- the reason for this is that the mobility of components contributing to pigment dispersion (for example, dispersants, surface treatment agents, etc.) is lowered at low temperature and the steric repulsion between pigments becomes smaller, and as a result, the pigment tends to reaggregate. It is guessed that When such an aggregate is formed in the coloring composition, the aggregate serves as a nucleus during storage of the coloring composition to promote aggregation of components contained in the coloring composition such as a metal azo pigment. It is assumed that the size of the aggregates grow and coarsen. When a film is produced using a coloring composition containing such coarse aggregates and the like, since the solvent is removed and disappears at the time of drying, these aggregates promote the crystallization of metal azo pigments and the like to cause defects.
- pigment dispersion for example, dispersants, surface treatment agents, etc.
- the coloring composition of the present invention further contains a compound having an ethylenically unsaturated bond group in addition to the metal azo pigment, so the compound having an ethylenically unsaturated bond group is a pigment active surface (especially azo portion) of the metal azo pigment.
- the compound having an ethylenically unsaturated bonding group can be adsorbed onto the surface of the metal azo pigment to stabilize the metal azo pigment in the coloring composition.
- re-aggregation and the like of the metal azo pigment can be suppressed even when the colored composition is stored for a long time under a low temperature environment.
- it is presumed that according to the coloring composition of the present invention it is possible to produce a film in which the occurrence of defects is suppressed even when stored for a long time under a low temperature environment.
- the coloring composition of this invention contains an oxime compound as a photoinitiator, generation
- the reason why such an effect can be obtained is presumed to be as follows.
- the metal azo pigment contained in the coloring composition of the present invention contains two or more types of metal ions, but depending on the type of metal ion, the arrangement of the metal azo compound (metal complex) composed of the anion and the metal ion described above The seat is different.
- Cu 2+ forms a metal complex in a planar conformation
- Zn 2+ forms a metal complex in octahedral conformation.
- the metal azo pigment described above is difficult to associate and present in an unstable state in the coloring composition containing a solvent and the like, and the metal azo pigment tends to easily aggregate when the coloring composition is stored. It is guessed that there is.
- the oxime compound coordinates to the metal azo pigment and acts as a chelating agent by blending the oxime compound, and as a result, the metal azo pigment can be stabilized, aggregation of the metal azo pigment, etc. It is speculated that it can be more effectively suppressed.
- the metal azo pigment can be stabilized, and it is presumed that the formation of minute aggregates that may cause the generation of foreign matter can also be suppressed. For this reason, even when the film obtained using the coloring composition is exposed to a high temperature and high humidity environment, it is presumed that the generation of foreign matter defects can be effectively suppressed.
- the coloring composition of this invention contains a pigment derivative. According to this aspect, it is possible to form a film in which the fluctuation of the spectrum with respect to the temperature change is suppressed.
- the coloring composition of the present invention comprises at least one anion selected from an azo compound represented by the following formula (I) and an azo compound having a tautomeric structure thereof, two or more types of metal ions, and a melamine compound. Containing metal azo pigments.
- R 1 and R 2 are each independently OH or NR 5 R 6
- R 5 to R 7 are each Independently, it is a hydrogen atom or an alkyl group.
- the carbon number of the alkyl group represented by R 5 to R 7 is preferably 1 to 10, more preferably 1 to 6, and still more preferably 1 to 4.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
- the alkyl group may have a substituent.
- substituent T the below-mentioned substituent T is mentioned, A halogen atom, a hydroxyl group, an alkoxy group, a cyano group, and an amino group are preferable.
- the melamine compound in the metal azo pigment is preferably a compound represented by the following formula (II).
- R 11 to R 13 each independently represent a hydrogen atom or an alkyl group.
- the carbon number of the alkyl group is preferably 1 to 10, more preferably 1 to 6, and still more preferably 1 to 4.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
- the alkyl group may have a substituent.
- the below-mentioned substituent T is mentioned and a hydroxyl group is preferable.
- at least one of R 11 ⁇ R 13 is a hydrogen atom, more preferably all of R 11 ⁇ R 13 is a hydrogen atom.
- the metal azo pigment used in the present invention is preferably a melamine compound (preferably a compound of the formula (II), per mole of at least one anion selected from the azo compound represented by the formula (I) and the azo compound of the tautomeric structure. It is preferable to contain 0.05 to 4 mol of a compound represented by), more preferably 0.5 to 2.5 mol, and still more preferably 1.0 to 2.0 mol.
- the specific surface area of the metal azo pigment used in the present invention is preferably 20 to 200 m 2 / g.
- the lower limit is preferably 60 m 2 / g or more, and more preferably 90 m 2 / g or more.
- the upper limit is preferably 160 m 2 / g or less, more preferably 150 m 2 / g or less.
- the value of the specific surface area of the metal azo pigment is determined according to the BET (Brunauer, Emmett and Teller) method in accordance with the method of DIN 66131: determination of the specific surface area of solids by gas adsorption It is the value measured according to).
- An alkyl group preferably an alkyl group having 1 to 30 carbon atoms
- an alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
- an alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably An aryl group having 6 to 30 carbon atoms, an amino group (preferably an amino group having 0 to 30 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 30 carbon atoms), an aryloxy group (preferably 6 to carbon atoms 30) aryloxy group), heteroaryloxy group
- acyl group preferably having 1 to 30 carbon atoms
- alkoxycarbonyl group preferably having 2 to 30 carbon atoms
- aryloxycarbonyl group preferably having 2 to 30 carbon atoms
- a metal complex is formed by the metal ion and at least one anion selected from the azo compound represented by the formula (I) and the azo compound of the tautomeric structure thereof.
- a metal complex having a structure represented by the following formula (Ia) can be formed by the above anion and the metal ion.
- the metal ion Me may also be bonded via the nitrogen atom in the tautomeric notation of formula (Ia).
- Preferred embodiments of the metal azo pigment used in the present invention include the metal azo pigments of the following aspects (1) to (4), and the effects of the present invention are more easily obtained, and further, the hardness is
- the metal azo pigment of the embodiment (1) is preferable because it is low and the fineness in the dispersion process is possible, and the color unevenness performance required for fine color filters can be improved, for example.
- Zn 2+ and Cu 2+ are preferably contained in a total amount of 95 to 100 mol%, more preferably 98 to 100 mol%, based on 1 mol of the total metal ions of the metal azo pigment. It is more preferable to contain 99.9 to 100 mol%, and it is particularly preferable to be 100 mol%.
- the metal azo pigment may further contain a divalent or trivalent metal ion other than Zn 2+ and Cu 2+ (hereinafter also referred to as a metal ion Me1).
- metal ion Me1 is, Ni 2+, Al 3+, Fe 2+, Fe 3+, Co 2+, Co 3+, La 3+, Ce 3+, Pr 3+, Nd 2+, Nd 3+, Sm 2+, Sm 3+, Eu 2+, Eu 3+ , Gd3 + , Tb3 + , Dy3 + , Ho3 + , Yb2 + , Yb3 + , Er3 + , Tm3 + , Mg2 + , Ca2 + , Sr2 + , Mn2 + , Y3 + , Sc3 + , Ti2 + , Ti3 + , Nb 3+, Mo 2+, Mo 3+, V 2+, V 3+, Zr 2+, Zr 3+, Cd 2+, Cr 3+, Pb 2+, Ba 2+ are mentioned, Al 3+, Fe 2+, Fe 3+, Co 2+, Co 3+, la 3+, Ce 3+, Pr 3+ , Nd 3+,
- the content of the metal ion Me1 is preferably 5 mol% or less, more preferably 2 mol% or less, and more preferably 0.1 mol% or less based on 1 mol of all metal ions of the metal azo pigment. It is further preferred that
- the metal ion comprises at least one anion selected from the azo compound represented by the formula (I) and the azo compound of the tautomeric structure described above, a metal ion, and a melamine compound, and the metal ion is Ni 2+ , Zn 2+ and at least one further metal ion Me 2, wherein the metal ion Me 2 is La 3+ , Ce 3+ , Pr 3+ , Nd 2+ , Nd 3+ , Sm 2+ , Sm 3+ , Eu 2+ , Eu 3+ , Gd 3+ , Tb3 + , Dy3 + , Ho3 + , Er3 + , Tm3 + , Yb2 + , Yb3 + , Mg2 + , Ca2 + , Sr2 + , Ba2 + , Sc3 + , Y3 + , Ti2 + , Ti3 + , Zr2 + , Zr3 + , V 2+, V 3+, Nb 3+
- the metal ion Me2 is La3 + , Ce3 + , Pr3 + , Nd3 + , Sm3 + , Eu3 + , Gd3 + , Tb3 + , Dy3 + , Ho3 + , Er3 + , Tm3 + , Yb3 + , Mg2 + , Ca2 + , Ca2 + , Ca2 + , Ca2 + , It is preferably at least one selected from Sr 2+ , Y 3+ , and Mn 2+ , and at least one selected from La 3+ , Ce 3+ , Pr 3+ , Nd 3+ , Sm 3+ , Tb 3+ , Ho 3+ , and Sr 2+ More preferably, it is a species.
- the metal azo pigment contains 75 to 99.5 mole% in total of Zn 2+ and Ni 2+ and 0.5 to 25 mole% of metal ion Me 2 preferably it contains, contains 78 to 95 mol% of Zn 2+ and Ni 2+ in total, and more preferably containing metal ions Me2 5 - 22 mol%, 82 to the Zn 2+ and Ni 2+ in total It is more preferable to contain 90 mol% and to contain 10 to 18 mol% of metal ion Me2.
- the metal ion contains at least one anion selected from the azo compound represented by the formula (I) and the azo compound of the tautomeric structure described above, a metal ion, and a melamine compound, and the metal ion is Ni 2+ , Cu 2+ and at least one further metal ion Me 3 , wherein the metal ion Me 3 is La 3+ , Ce 3+ , Pr 3+ , Nd 2+ , Nd 3+ , Sm 2+ , Sm 3+ , Eu 2+ , Eu 3+ , Gd 3+ , Tb 3 3+ , Dy3 + , Ho3 + , Yb2 + , Yb3 + , Er3 + , Tm3 + , Mg2 + , Ca2 + , Ca2 + , Sr2 + , Mn2 + , Y3 + , Sc3 + , Ti2 + , Ti3 + , Nb3 + , Mo2 + , Mo 3+, V
- the metal ion Me3 is La3 + , Ce3 + , Pr3 + , Nd3 + , Sm3 + , Eu3 + , Gd3 + , Tb3 + , Dy3 + , Ho3 + , Yb3 + , Er3 + , Tm3 + , Mg2 + , Ca2 + , Ca2 + , Ca2 + , It is preferably at least one selected from Sr 2+ , Mn 2+ , and Y 3+ , and at least one selected from La 3+ , Ce 3+ , Pr 3+ , Nd 3+ , Sm 3+ , Tb 3+ , Ho 3+ , and Sr 2+. More preferably, it is a species.
- the total content of Cu 2+ and Ni 2+ is 70 to 99.5 mol%, and 0.5 to 30 mol% of metal ion Me3. preferably contains contains 75-95 mol% of Cu 2+ and Ni 2+ in total, and more preferably containing metal ions Me3 5 - 25 mol%, 80 to the Cu 2+ and Ni 2+ in total It is more preferable to contain 90 mol% and to contain 10 to 20 mol% of metal ion Me3.
- the metal ion contains at least one anion selected from the azo compound represented by the formula (I) and the azo compound of the tautomeric structure described above, a metal ion, and a melamine compound, and the metal ion is Ni 2+ and comprises a metal ion Me4a, metal ions Me4a is La 3+, Ce 3+, Pr 3+ , Nd 2+, Nd 3+, Sm 2+, Sm 3+, Eu 2+, Eu 3+, Gd 3+, Tb 3+, Dy 3+, Ho 3+,
- the metal azo pigment of the aspect which is an at least 1 sort (s) chosen from Er ⁇ 3 +> , Tm ⁇ 3 + > , Yb ⁇ 2+> and Yb ⁇ 3+ >.
- Metal ions Me4a is, La 3+, Ce 3+, Pr 3+, Nd 3+, Sm 3+, Eu 3+, Gd 3+, Tb 3+, Dy 3+, Ho 3+, Er 3+, at least one selected from the Tm 3+ and Yb 3+ It is preferably at least one selected from La 3+ , Ce 3+ , Pr 3+ , Nd 3+ , Sm 3+ , Tb 3+ and Ho 3+ .
- the total content of Ni 2+ and metal ion Me 4 a is preferably 95 to 100 mol%, more preferably 98 to 100 mol%, based on 1 mol of the total metal ions of the metal azo pigment.
- the metal azo pigment may further contain metal ions other than Ni 2+ and metal ion Me4a (hereinafter also referred to as metal ion Me4b).
- the metal ions Me4b is, Mg 2+, Ca 2+, Sr 2+, Ba 2+, Sc 3+, Y 3+, Ti 2+, Ti 3+, Zr 2+, Zr 3+, V 2+, V 3+, Nb 3+, Cr 3+, Mo 2+ , Mo 3+ , Mn 2+ , Fe 2+ , Fe 3+ , Co 2+ , Co 3+ , Cu 2+ , Zn 2+ , Cd 2+ , Al 3+ and Pb 2+ , and Mg 2+ , Ca 2+ , Sr 2+ , Y 3+ , Mn It is preferably at least one selected from 2+ , Fe 2+ , Fe 3+ , Co 2+ , Co 3+ , Cu 2+ , Zn 2+ and Al 3+ , and Sr 2+ , Fe 2+ , Fe 3+ , Co 2+ , Co 3+ , Cu More preferably, it is at least one selected from 2+ , Zn 2
- the content of the metal ion Me4b is preferably 5 mol% or less, more preferably 2 mol% or less, based on 1 mol of the total metal ions of the metal azo pigment, more preferably 0.1 mol% It is more preferable that it is the following.
- the metal azo pigment used in the present invention is a metal azo compound composed of at least one anion selected from the azo compound represented by the above-mentioned formula (I) and the azo compound of the tautomeric structure thereof and a metal ion. It is preferable that an adduct is formed of a melamine compound (preferably, a compound represented by the above formula (II)). An adduct is understood to mean a molecular assembly. The bond between these molecules may be, for example, an intermolecular interaction, a Lewis acid-base interaction, or a coordinate bond or a chain bond.
- the adduct may also have a structure such as a clathrate in which a guest molecule is incorporated in a lattice constituting a host molecule.
- the adduct may also have a structure such as a complex intercalated crystal (including an interstitial compound).
- Composite intercalated crystals are chemically non-stoichiometric crystalline compounds consisting of at least two components.
- the adduct may be a mixed substituted crystal in which two substances form a co-crystal and the atom of the second component is located at the regular lattice position of the first component.
- the metal azo pigment used in the present invention may be a physical mixture or a chemically complex compound. Preferably, it is a physical mixture.
- Preferred examples of the physical mixture in the case of the metal azo pigment of the above aspect (1) include the following (1-1) and (1-2).
- the metal azo pigment of the aspect of (1) is a chemical complex compound, it is preferable that Zn 2+ , Cu 2+ and optional additional metal ion Me1 be incorporated in a common crystal lattice.
- (1-1) An adduct of the metal azo compound composed of the anion and Zn 2+ , an adduct 1a of a melamine compound, a metal azo compound composed of the anion and Cu 2+ , and the melamine compound Physical mixture of 1b.
- (1-2) A physical mixture containing, in the physical mixture of (1-1), an adduct 1c of a metal azo compound composed of the above anion and a metal ion Me1, and a melamine compound.
- Preferred examples of the physical mixture in the case of the metal azo pigment of the above aspect (2) include the following (2-1).
- the metal azo pigment of the embodiment (2) is a chemically complex compound, it is preferable that Ni 2+ , Zn 2+ and metal ion Me2 be incorporated in a common crystal lattice.
- a physical mixture comprising an adduct 2c of a metal azo compound composed of 2b, the above anion and a metal ion Me2, and a melamine compound.
- Preferred examples of the physical mixture in the case of the metal azo pigment of the above aspect (3) include the following (3-1).
- the metal azo pigment of the embodiment (3) is a chemically complex compound, it is preferable that Ni 2+ , Cu 2+ and metal ion Me 3 be incorporated in a common crystal lattice.
- (3-1) An adduct of a metal azo compound composed of the anion and Ni 2+ , an adduct 3a of a melamine compound, a metal azo compound composed of the anion and Cu 2+ , and a melamine compound
- a physical mixture comprising an adduct 3c of a metal azo compound composed of 3b, the above anion and a metal ion Me3, and a melamine compound.
- Preferred examples of the physical mixture in the case of the metal azo pigment of the above aspect (4) include the following (4-1) and (4-2). Also, when the metal azo pigment of the aspect of (4) is a chemically complex compound, it is preferable that Ni 2+ , metal ion Me4a and optional additional metal ion Me4b be incorporated in a common crystal lattice.
- (4-1) Addition of a metal azo compound composed of the above anion and Ni 2+ , an adduct 4a of a melamine compound, a metal azo compound composed of the above anion and a metal ion Me 4 a, and a melamine compound Physical mixture of body 4b.
- (4-2) A physical mixture containing, in the physical mixture of (4-1), an adduct 4c of a metal azo compound composed of the anion and the metal ion Me4b, and a melamine compound.
- the metal azo pigment of the above aspect (1) comprises a compound of the formula (III) or a tautomer thereof, a zinc salt and a zinc salt in the presence of a melamine compound (preferably a compound represented by the formula (II)) It can be produced by reacting with a copper salt, and optionally also with the above mentioned salts of the metal ion Me1.
- X 1 and X 2 each independently represent a hydrogen atom or an alkali metal ion, and at least one of X 1 and X 2 is an alkali metal ion.
- R 1 and R 2 are each independently OH or NR 5 R 6 .
- R 5 to R 7 are each independently a hydrogen atom or an alkyl group.
- R 1 ⁇ R 7 has the same meaning as R 1 ⁇ R 7 of formula (I), preferred ranges are also the same. Examples of the alkali metal ions which X 1 and X 2 represent, Na + and K + are preferred.
- the amount of the zinc salt used is preferably 0.05 to 0.995 mol, more preferably 0.05 to 0.5 mol, per 1 mol of the compound of the formula (III) or a tautomer thereof. More preferably, it is 0.1 to 0.3 mol.
- the amount of the copper salt used is preferably 0.005 to 0.95 mol, preferably 0.49 to 0.95 mol, per 1 mol of the compound of the formula (III) or a tautomer thereof. Is more preferably 0.7 to 0.9 mole.
- the amount of the metal ion Me1 salt used is preferably 0.05 moles or less, and preferably 0.01 moles or less, per mole of the compound of the formula (III) or a tautomer thereof. Is more preferred.
- the total amount of a zinc salt, a copper salt, and the metal ion Me1 salt is 1 mol with respect to 1 mol of compounds of Formula (III).
- the amount of the melamine compound used is preferably 0.05 to 4 moles, and more preferably 0.5 to 2.5 moles relative to 1 mole of the compound of the formula (III) or a tautomer thereof. Is more preferably 1.0 to 2.0 mol.
- the metal azo pigment of the aspect of said (1) can also be manufactured by mixing the adduct 1a mentioned above, the adduct 1b, and the adduct 1c.
- the metal azo pigment of the embodiment (2), the metal azo pigment of the embodiment (3), and the metal azo pigment of the embodiment (4) can also be produced by the same method as described above.
- paragraphs 0011 to 0062 and 0139 to 0190 of the gazettes and paragraphs 0010 to 0065 and 0142 to 2222 of JP-A-2017-171915 can be referred to, and the contents thereof are incorporated herein.
- the content of the metal azo pigment is preferably 1 to 80% by mass with respect to the total solid content of the coloring composition.
- the lower limit is preferably 3% by mass or more, and more preferably 5% by mass or more.
- the upper limit is preferably 77% by mass or less and more preferably 75% by mass or less.
- the coloring composition of the present invention can contain a colorant (hereinafter also referred to as another colorant) other than the metal azo pigment described above.
- Other coloring agents include chromatic coloring agents, black coloring agents and the like.
- the chromatic coloring agent As the chromatic coloring agent, red coloring agent, green coloring agent, blue coloring agent, yellow coloring agent, purple coloring agent, orange coloring agent and the like can be mentioned.
- the chromatic coloring agent may be a pigment or a dye.
- the chromatic colorant preferably contains a pigment. The foreign matter growth in the high temperature and high humidity environment of the metal azo pigment can be suppressed by further including the different type pigment in addition to the metal azo pigment mentioned above in the coloring composition of the present invention.
- Pigments include organic pigments and inorganic pigments, with organic pigments being preferred.
- organic pigments include the following. Color Index (CI) Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 35, 53, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170
- the dye is not particularly limited, and known dyes can be used.
- pyrazole azo type anilino azo type, triarylmethane type, anthraquinone type, anthrapyridone type, benzylidene type, oxonol type, pyrazolotriazole azo type, pyridone azo type, cyanine type, phenothiazine type, pyrrolopyrazole azomethine type, xanthene type, Dyes of phthalocyanine type, benzopyran type, indigo type, and pyromethene type can be used.
- multimers of these dyes may be used.
- dyes described in JP-A-2015-028144 and JP-A-2015-34966 can also be used.
- a halogenated zinc phthalocyanine pigment having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms and an average of 2 to 5 chlorine atoms is used. It can also be done. Specific examples include the compounds described in International Publication WO 2015/118720.
- the aluminum phthalocyanine compound which has a phosphorus atom can also be used as a blue pigment.
- Specific examples thereof include the compounds described in paragraphs 0022 to 0030 of JP-A-2012-247591 and paragraph 0047 of JP-A-2011-157478.
- red pigment a compound having a structure in which an aromatic ring group in which a group in which an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is introduced is bonded to a diketopyrrolopyrrole skeleton is also used. It can.
- a compound represented by the formula (DPP1) is preferable, and a compound represented by the formula (DPP2) is more preferable.
- R 11 and R 13 each independently represent a substituent
- R 12 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group
- n 11 and n 13 are each independently
- X 12 and X 14 each independently represent an oxygen atom, a sulfur atom or a nitrogen atom
- m 12 represents 1 and X is an integer of 0 to 4
- X 14 is a nitrogen atom
- m14 represents 2
- Examples of the substituent represented by R 11 and R 13 include the groups listed above as the substituent T, and an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryloxycarbon
- the dye is not particularly limited, and known dyes can be used.
- the chemical structure includes pyrazole azo, anilinoazo, triarylmethane, anthraquinone, anthrapyridone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine, Dyes such as xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyromethene dyes can be used.
- a thiazole compound described in JP-A-2012-158649, an azo compound described in JP-A-2011-184493, and an azo compound described in JP-A-2011-145540 can also be preferably used.
- a yellow dye a quinophthalone compound described in paragraph 0011 to 0034 of JP-A-2013-54339, a quinophthalone compound described in paragraph 0013 to 0058 of JP-A 2014-26228, or the like can be used.
- dye multimer can also be used as another coloring agent.
- the dye multimer is preferably a dye used by being dissolved in a solvent, but the dye multimer may form particles, and when the dye multimer is particles, it is usually dispersed in a solvent. Used.
- the dye multimer in a particulate state can be obtained, for example, by emulsion polymerization, and the compounds and production methods described in JP-A-2015-214682 can be mentioned as specific examples.
- the dye multimer has two or more dye structures in one molecule, and preferably three or more dye structures. The upper limit is not particularly limited, but may be 100 or less. Plural dye structures in one molecule may be the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
- the lower limit is more preferably 3000 or more, and still more preferably 6000 or more.
- the upper limit is more preferably 30000 or less, further preferably 20000 or less.
- compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742 and the like can also be used.
- Black coloring agent As the black colorant, inorganic black colorants such as carbon black, metal oxynitrides (titanium black etc.), metal nitrides (titanium nitride etc.), bisbenzofuranone compounds, azomethine compounds, perylene compounds, azo compounds etc. Organic black colorants.
- organic black colorant bisbenzofuranone compounds and perylene compounds are preferable.
- the bisbenzofuranone compounds include the compounds described in JP-A-2010-534726, JP-A-2012-515233, JP-A-2012-515234, etc.
- Irgaphor Black manufactured by BASF Corp. It is available.
- perylene compounds C.I. I.
- the bisbenzofuranone compound is preferably a compound represented by the following formula and a mixture thereof.
- R 1 and R 2 each independently represent a hydrogen atom or a substituent
- R 3 and R 4 each independently represent a substituent
- a and b each independently represent an integer of 0 to 4
- a is 2 or more
- plural R 3 s may be the same or different
- plural R 3 s may combine to form a ring
- b is 2 or more
- the plurality of R 4 may be identical or different, and the plurality of R 4 may be combined to form a ring.
- a black color may be formed by the combination of the metal azo pigment described above and the other colorant.
- the total content of the metal azo pigment and other colorants described above is preferably 10 to 80% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 15% by mass or more, and more preferably 20% by mass or more.
- the upper limit is preferably 77% by mass or less and more preferably 75% by mass or less.
- the content of the yellow coloring agent as the other coloring agent is 5 to 95 parts by mass with respect to 100 parts by mass of the metal azo pigment described above.
- the lower limit is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more.
- the upper limit is preferably 92 parts by mass or less, and more preferably 90 parts by mass or less. According to this aspect, it can be preferably used as a coloring composition for yellow pixels. Furthermore, the foreign matter growth in the high temperature and high humidity environment of the metal azo pigment can also be suppressed by further containing the different pigment.
- yellow colorants include C.I. I. Pigment Yellow 62, 83, 74, 100, 129, 138, 139, 150, 168, 169, 183, 185, 213 and the like are preferably used.
- content of the green coloring agent as another coloring agent is 5-95 mass parts with respect to 100 mass parts of the metal azo pigment mentioned above Is preferred.
- the lower limit is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more.
- the upper limit is preferably 92 parts by mass or less, and more preferably 90 parts by mass or less. According to this aspect, it can be preferably used as a coloring composition for green pixels. Furthermore, the foreign matter growth in the high temperature and high humidity environment of the metal azo pigment can also be suppressed by further containing the different pigment.
- a green coloring agent for example, C.I. I. Pigment Green 7, 36, 58, 59, etc. are preferably used.
- the content of the red colorant as the other colorant is 5 to 95 parts by mass with respect to 100 parts by mass of the metal azo pigment described above Is preferred.
- the lower limit is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more.
- the upper limit is preferably 92 parts by mass or less, and more preferably 90 parts by mass or less. According to this aspect, it can be preferably used as a coloring composition for red pixels. Furthermore, the foreign matter growth in the high temperature and high humidity environment of the metal azo pigment can also be suppressed by further containing the different pigment.
- a red coloring agent for example, C.I. I. Pigment Red 122, 177, 202, 209, 254, 264, 269, etc. are preferably used.
- content of the orange coloring agent as another coloring agent is 5-95 mass parts with respect to 100 mass parts of the metal azo pigments mentioned above Is preferred.
- the lower limit is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more.
- the upper limit is preferably 92 parts by mass or less, and more preferably 90 parts by mass or less. According to this aspect, it can be preferably used as a coloring composition for red pixels. Furthermore, the foreign matter growth in the high temperature and high humidity environment of the metal azo pigment can also be suppressed by further containing the different pigment.
- an orange coloring agent for example, C.I. I. Pigment Orange 38, 71, etc. are preferably used.
- the coloring composition of the present invention contains a compound having an ethylenically unsaturated bonding group.
- a compound having an ethylenically unsaturated bond group a vinyl group, a (meth) allyl group, a (meth) acryloyl group etc. are mentioned.
- the compound having an ethylenically unsaturated bond group may be a monomer or a resin such as a polymer.
- a monomer having an ethylenically unsaturated bond group is also referred to as a polymerizable monomer.
- a polymer having an ethylenically unsaturated bond group is also referred to as a polymerizable polymer.
- the molecular weight of the polymerizable monomer is preferably less than 3000.
- the upper limit is more preferably 2000 or less, still more preferably 1500 or less.
- the lower limit is preferably 100 or more, more preferably 150 or more, and still more preferably 250 or more.
- the polymerizable monomer is preferably a compound containing 3 or more ethylenic unsaturated bonding groups, more preferably a compound containing 3 to 15 ethylenic unsaturated bonding groups, and an ethylenic unsaturated bonding group. More preferably, it is a compound containing 3 to 6.
- the polymerizable monomer is preferably a 3 to 15 functional (meth) acrylate compound, and more preferably a 3 to 6 functional (meth) acrylate compound.
- Specific examples of the polymerizable monomer are described in paragraph Nos. 0095 to 0108 of JP2009-288705A, paragraph 0227 of JP2013-29760A, and paragraph 0254-0257 of JP2008-292970A. Compounds are included, the contents of which are incorporated herein.
- the lower limit is preferably 60 or more, and more preferably 70 or more.
- the upper limit is preferably 700 or less, more preferably 500 or less, still more preferably 200 or less, still more preferably 150 or less, and particularly preferably 140 or less.
- dipentaerythritol triacrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available as KAYARAD D-320; Nippon Kayaku Co., Ltd.)
- Dipentaerythritol penta (meth) acrylate (Commercial product: KAYARAD D-310; Nippon Kayaku Co., Ltd.), Dipentaerythritol hexa (meth) acrylate
- KAYARAD DPHA Nippon Kayaku ( Ltd.
- NK ester A-DPH-12E Shin-Nakamura Chemical Co., Ltd. product
- the compound of the structure where these (meth) acryloyl groups are linked via ethylene glycol and / or propylene glycol residue (For example, commercially available from Sartmar And has, SR454, SR499), NK ester A-TMMT (manufactured by Shin-Nakamura Chemical Industry Co.), manufactured KAYARAD RP-1040, DPCA-20 (Nippon Kayaku Co.) and the like.
- trimethylolpropane tri (meth) acrylate trimethylolpropane propyleneoxy modified tri (meth) acrylate, trimethylolpropane ethyleneoxy modified tri (meth) acrylate, isocyanuric acid ethyleneoxy modified tri (meth) acrylate
- a trifunctional (meth) acrylate compound such as pentaerythritol tri (meth) acrylate.
- Commercially available products of trifunctional (meth) acrylate compounds include Alonics M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
- M-303, M-452, M-450 (manufactured by Toagosei Co., Ltd.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) Etc.
- a polymerizable monomer having an acid group As the polymerizable monomer, the colored composition layer in the unexposed area is easily removed during development, and the generation of development residues can be effectively suppressed.
- an acid group a carboxyl group, a sulfo group, a phosphoric acid group etc. are mentioned, A carboxyl group is preferable.
- Commercially available products of the polymerizable monomer having an acid group include ALONIX M-510, M-520, ALONIX TO-2349 (manufactured by Toagosei Co., Ltd.), and the like.
- the acid value of the polymerizable monomer having an acid group is preferably 0.1 to 40 mg KOH / g, and more preferably 5 to 30 mg KOH / g.
- the acid value of the polymerizable monomer is 0.1 mg KOH / g or more, the solubility in a developer is good, and more excellent developability can be obtained.
- the acid value of the polymerizable monomer is 40 mg KOH / g or less, it is advantageous in terms of production and handling.
- n 0-14 and m is 1-8.
- a plurality of R and T in one molecule may be identical to or different from each other.
- Specific examples of the compounds represented by the above formulas (MO-1) to (MO-6) include the compounds described in paragraphs 0248 to 0251 of JP-A-2007-269779.
- the compound having a caprolactone structure is not particularly limited as long as it has a caprolactone structure in the molecule, and examples thereof include trimethylol ethane, ditrimethylol ethane, trimethylol propane, ditrimethylol propane, pentaerythritol, dipentaerythritol, and tripentaerythritol.
- ⁇ -caprolactone modified polyfunctional (meth) acrylates obtained by esterifying polyhydric alcohols such as glycerin, diglycerol and trimethylolmelamine with (meth) acrylic acid and ⁇ -caprolactone.
- the compound having a caprolactone structure is preferably a compound represented by the following formula (Z-1).
- R 1 represents a hydrogen atom or a methyl group
- m represents a number of 1 or 2
- “*” represents a bond.
- R 1 represents a hydrogen atom or a methyl group
- “*” represents a bond
- a compound represented by Formula (Z-4) or (Z-5) can also be used.
- each E is independently-((CH 2 ) y CH 2 O)-or-((CH 2 ) y CH (CH 3 ) O)- And y each independently represents an integer of 0 to 10, and each X independently represents a (meth) acryloyl group, a hydrogen atom or a carboxyl group.
- the total of (meth) acryloyl groups is three or four, m each independently represents an integer of 0 to 10, and the sum of each m is an integer of 0 to 40.
- the total of (meth) acryloyl groups is five or six, n independently represents an integer of 0 to 10, and the sum of each n is an integer of 0 to 60.
- n is preferably an integer of 0 to 6, and more preferably an integer of 0 to 4.
- the total of each n is preferably an integer of 3 to 60, more preferably an integer of 3 to 24, and particularly preferably an integer of 6 to 12.
- a compound having an alkyleneoxy group can also be used as the polymerizable monomer.
- the polymerizable monomer having an alkyleneoxy group is preferably a compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a compound having an ethyleneoxy group, and having 4 to 20 ethyleneoxy groups. More preferably, it is a 3- to 6-functional (meth) acrylate compound.
- SR-494 which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartomer, a trifunctional (meth) having three isobutylene oxy groups
- examples thereof include KAYARAD TPA-330 which is an acrylate.
- urethane acrylates as described in JP-B-48-41708, JP-A-51-37193, JP-B-2-32293 and JP-B-2-16765, and The urethane compounds having an ethylene oxide skeleton described in JP-B-58-49860, JP-B-56-17654, JP-B-62-39417, and JP-B-62-39418 are also suitable. Further, it is also preferable to use a compound having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-1-105238.
- UA-7200 Shin-Nakamura Chemical Co., Ltd. product
- DPHA-40H Nippon Kayaku Co., Ltd. product
- UA-306H, UA-306T, UA-306I, AH-600, T- 600, AI-600 manufactured by Kyoeisha Chemical Co., Ltd.
- the polymerizable monomer it is also preferable to use 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), light acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), and the like.
- compounds described in JP-A-2017-48367, JP-A-6057891, and JP-A-6031807 can also be used.
- the weight average molecular weight of the polymerizable polymer is preferably 3,000 or more, more preferably 5,000 or more, still more preferably 7,000 or more, and particularly preferably 10,000 or more.
- the weight average molecular weight of the polymerizable polymer is preferably 50,000 or less, more preferably 40,000 or less, and still more preferably 30,000 or less.
- the lower limit is preferably 150 or more, and more preferably 200 or more.
- the upper limit is preferably 4500 or less, more preferably 4000 or less.
- the polymerizable polymer preferably contains a repeating unit having an ethylenically unsaturated bonding group in a side chain, and more preferably contains a repeating unit represented by the following formula (A-1-1).
- the polymerizable polymer preferably contains 10 mol% or more, more preferably 10 to 80 mol%, of repeating units having an ethylenically unsaturated bond group in all repeating units of the polymerizable polymer, and more preferably 20 to 70. It is more preferable to contain mol%.
- X 1 represents a main chain of a repeating unit
- L 1 represents a single bond or a divalent linking group
- Y 1 represents an ethylenically unsaturated bonding group.
- an alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- an alkyleneoxy group preferably an alkylene having 1 to 12 carbon atoms
- Oxy group oxyalkylene carbonyl group
- arylene group preferably arylene group having 6 to 20 carbon atoms
- examples of the ethylenically unsaturated bonding group represented by Y 1 include a vinyl group, a (meth) allyl group, a (meth) acryloyl group and the like, and a (meth) acryloyl group is preferable.
- An acryloyl group is more preferred.
- the polymerizable polymer preferably further contains a repeating unit having a graft chain.
- the polymerizable polymer preferably contains a repeating unit having a graft chain in an amount of 1.0 to 60% by mole, and more preferably 1.5 to 50% by mole, based on all repeating units of the polymerizable polymer.
- a polymerizable polymer containing a repeating unit having a graft chain is preferably used as a dispersant.
- a graft chain means a polymer chain which branches and extends from the main chain of a repeating unit.
- the length of the graft chain is not particularly limited, but as the graft chain becomes longer, the steric repulsion effect becomes higher, and the dispersibility of the metal azo pigment etc. can be enhanced.
- the graft chain preferably has 40 to 10,000 atoms excluding hydrogen atoms, more preferably 50 to 2,000 atoms excluding hydrogen atoms, and 60 to 60 atoms excluding hydrogen atoms. More preferably, it is 500.
- the graft chains possessed by the polymerizable polymer preferably include at least one structure selected from polyester structure, polyether structure, poly (meth) acrylic structure, polyurethane structure, polyurea structure and polyamide structure, and polyester structure, polyether It is more preferable to include at least one structure selected from a structure and a poly (meth) acrylic structure, and it is further preferable to include a polyester structure.
- the polyester structure include structures represented by the following Formula (G-1), Formula (G-4) or Formula (G-5).
- the polyether structure a structure represented by the following formula (G-2) can be mentioned.
- examples of the poly (meth) acrylic structure include a structure represented by the following formula (G-3).
- R G1 and R G2 each represent an alkylene group.
- the alkylene group represented by R G1 and R G2 is not particularly limited, but a linear or branched alkylene group having 1 to 20 carbon atoms is preferable, and a linear or branched alkylene having 2 to 16 carbon atoms is preferable. A group is more preferable, and a linear or branched alkylene group having 3 to 12 carbon atoms is further preferable.
- R G3 represents a hydrogen atom or a methyl group.
- Q G1 represents -O- or -NH-
- L G1 represents a single bond or a divalent linking group.
- Examples of the divalent linking group include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), and an oxyalkylene carbonyl group (preferably having 1 carbon atom).
- an alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- an alkyleneoxy group preferably an alkyleneoxy group having 1 to 12 carbon atoms
- an oxyalkylene carbonyl group preferably having 1 carbon atom.
- arylene group preferably arylene group having 6 to 20 carbon atoms
- R G4 represents a hydrogen atom or a substituent.
- substituents examples include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- the graft chain may contain only one type of polyester structure may include R G1 is different polyester structure of two or more.
- R G1 is different polyester structure of two or more.
- the graft chain may contain only one type of polyether structure, and R G2 may contain two or more different polyether structures.
- the graft chain contains a poly (meth) acrylic structure, it may contain only one poly (meth) acrylic structure, and at least one selected from R G3 , Q G1 , L G1 and R G4 is Two or more kinds of different poly (meth) acrylic structures may be included.
- the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
- substituents include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group having 5 to 24 carbon atoms or an alkoxy group is preferable, from the viewpoint of improving the dispersibility of the coloring material and the like.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, and linear or branched is preferable.
- a structure represented by the following formula (G-1a), formula (G-2a), formula (G-3a), formula (G-4a) or formula (G-5a) Is preferred.
- R G1 and R G2 each represent an alkylene group
- R G3 represents a hydrogen atom or a methyl group
- Q G1 represents -O- or -NH-
- L G1 represents a single bond
- R G4 represents a hydrogen atom or a substituent
- W 100 represents a hydrogen atom or a substituent.
- n1 to n5 each independently represent an integer of 2 or more.
- Q G1 , L G1 , Formula (G1) ⁇ (G-5 ) has the same meaning as R G1 ⁇ R G4, Q G1 , L G1 described in, the preferred range is also the same is there.
- W 100 is preferably a substituent.
- the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group having 5 to 24 carbon atoms or an alkoxy group is preferable, from the viewpoint of improving the dispersibility of the coloring material and the like.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, and linear or branched is preferable.
- n1 to n5 each independently represent an integer of 2 or more, more preferably 3 or more, and still more preferably 5 or more.
- the upper limit is preferably 100 or less, more preferably 80 or less, and still more preferably 60 or less.
- R G1 's in the respective repeating units may be the same or different.
- the arrangement of each repeating unit is not particularly limited, and may be random, alternating, or block. The same applies to formulas (G-2a) to (G-5a).
- repeating unit having a graft chain examples include repeating units represented by the following formula (A-1-2).
- X 2 represents a main chain of a repeating unit
- L 2 represents a single bond or a divalent linking group
- W 1 represents a graft chain.
- Examples of the main chain of the repeating unit represented by X 2 in Formula (A-1-2) include the structures described in X 1 of Formula (A-1-1), and preferred ranges are also the same.
- the divalent linking group represented by L 2 in Formula (A-1-2) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an arylene group (preferably an arylene group having 6 to 20 carbon atoms) And -NH-, -SO-, -SO 2- , -CO-, -O-, -COO-, OCO-, -S- and a group formed by combining two or more of these.
- Examples of the graft chain represented by W 1 in formula (A-1-2) include the graft chains described above.
- the weight average molecular weight (Mw) of the repeating unit having a graft chain is preferably 1000 or more, more preferably 1000 to 10000, and 1000 to 7500. It is further preferred that In the present invention, the weight average molecular weight of the repeating unit having a graft chain is a value calculated from the weight average molecular weight of the raw material monomer used for the polymerization of the same repeating unit.
- a repeating unit having a graft chain can be formed by polymerizing a macromonomer.
- the macromonomer means a polymer compound in which a polymerizable group is introduced at the polymer end.
- the polymerizable polymer further contains a repeating unit having an acid group.
- the dispersibility of a metal azo pigment or the like can be further improved.
- developability can also be improved.
- the acid group include a carboxyl group, a sulfo group and a phosphate group.
- repeating unit having an acid group examples include repeating units represented by the following formula (A-1-3).
- X 3 represents a main chain of a repeating unit
- L 3 represents a single bond or a divalent linking group
- a 1 represents an acid group.
- the divalent linking group represented by L 3 in Formula (A-1-3) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an alkenylene group (preferably an alkenylene group having 2 to 12 carbon atoms) , An alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), an oxyalkylene carbonyl group (preferably an oxyalkylene carbonyl group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms) And —NH—, —SO—, —SO 2 —, —CO—, —O—, —COO—, OCO—, —S— and groups in which two or more of these are combined.
- the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylene carbonyl group may be linear, branched or cyclic, and is preferably linear or branched. Further, the alkylene group, the alkylene group in the alkyleneoxy group, and the alkylene group in the oxyalkylene carbonyl group may have a substituent or may be unsubstituted. As a substituent, a hydroxy group etc. are mentioned.
- Examples of the acid group represented by A 1 in formula (A-1-3) include a carboxyl group, a sulfo group and a phosphoric acid group.
- polymerizable polymer may also be referred to as a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) as another repeating unit (hereinafter, these compounds are referred to as “ether dimer” And B.) can be included.
- ED1 a compound represented by the following formula
- ED2 a compound represented by the following formula
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to.
- ether dimer for example, paragraph “0317” of JP-A-2013-29760 can be referred to, and the contents thereof are incorporated in the present specification.
- the ether dimer may be only one type, or two or more types.
- the content of the compound having an ethylenically unsaturated bonding group is preferably 5 to 50% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the content of the compound having an ethylenically unsaturated bond group is preferably 10 parts by mass or more, more preferably 12 parts by mass or more, with respect to 100 parts by mass of the metal azo pigment described above. More preferably, it is at least 20 parts by mass, and particularly preferably at least 20 parts by mass.
- the upper limit is preferably 500 parts by mass or less, more preferably 400 parts by mass or less, still more preferably 200 parts by mass or less, and particularly preferably 100 parts by mass or less. If the ratio of the metal azo pigment and the compound having an ethylenically unsaturated bond group is in the above-mentioned range, the effect of the present invention is more remarkably obtained.
- the compound having an ethylenically unsaturated bond group contained in the coloring composition of the present invention preferably contains at least the polymerizable monomer described above from the viewpoint of patternability by photolithography, and the polymerizability described above More preferably, it contains a monomer and a polymerizable polymer.
- the content of the polymerizable polymer is preferably 5 to 500 parts by mass with respect to 100 parts by mass of the polymerizable monomer.
- the lower limit is preferably 8 parts by mass or more, and more preferably 10 parts by mass or more.
- the upper limit is preferably 450 parts by mass or less, and more preferably 400 parts by mass or less.
- the coloring composition of the present invention can contain a compound having a cyclic ether group.
- a compound having two or more cyclic ether groups in one molecule is preferably used.
- the number of cyclic ether groups contained in the compound having a cyclic ether group is preferably 100 or less, more preferably 10 or less, and still more preferably 5 or less.
- the cyclic ether group may, for example, be an epoxy group or an oxetanyl group, and is preferably an epoxy group. That is, the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter, also referred to as an epoxy compound).
- the epoxy compound may be a low molecular weight compound (for example, a molecular weight of less than 1000) or a macromolecular compound (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more).
- the molecular weight (weight average molecular weight in the case of a polymer) of the epoxy compound is preferably 200 to 100,000, and more preferably 500 to 50,000. 3000 or less is preferable, as for the upper limit of molecular weight (in the case of a polymer, weight average molecular weight), 2000 or less is more preferable, and 1500 or less is still more preferable.
- the epoxy compounds are compounds described in paragraphs 0034 to 0036 in JP 2013-011869A, paragraphs 0147 to 0156 in JP 2014-043556 A, and paragraphs 0085 to 0092 in JP 2014-089408 A. Can also be used. The contents of these are incorporated herein.
- the epoxy compound for example, as bisphenol A type epoxy resin, jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, jER1010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON 860, EPICLON 1050, EPICLON 1051, EPICLON 1055 (all manufactured by DIC Corporation) and the like, and as a bisphenol F-type epoxy resin, jER806, jER807, jER4004, jER4005, jER4007, jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON 830, EPICLON 835 (above, DIC Corporation), LCE-21, RE-602S (above, Japan Drugs, etc., and as phenol novolac type epoxy resins, jER152, jER154, jER157S70, jER157S65 (abo
- EPICLON N-695 (all, DIC Corporation), EOCN-1020 (Nippon Kayaku Co., Ltd.), etc.
- ADEKA RESIN EP-4080S As aliphatic epoxy resins, ADEKA RESIN EP-4080S, EP 4085S, EP-4088S (above, made by ADEKA Co., Ltd.), Celoxide 2021 P, Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE 3150, EPOLEAD PB 3600, same PB 4700 (above, made by Daicel), Denacol EX- 212L, EX-214L, EX-216L, EX-321L, EX-850L (all manufactured by Nagase ChemteX Co., Ltd.) and the like.
- ADEKA RESIN EP-4000S, EP-4003S, EP-4010S, EP-4011S (above, made by ADEKA), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, EPPN-502 (above, manufactured by ADEKA Co., Ltd.), jER1031S (manufactured by Mitsubishi Chemical Corporation), merproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G And -1005SA, G-1010S, G-2050M, G-01100, G-01758 (manufactured by NOF Corporation, epoxy group-containing polymer) and the like.
- the content of the compound having a cyclic ether group is preferably 0.5 to 30% by mass in the total solid content of the coloring composition.
- the lower limit is preferably 0.8% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 25% by mass or less, and more preferably 20% by mass or less.
- the coloring composition of the present invention can further contain a resin not containing an ethylenically unsaturated bond group (hereinafter also referred to as another resin).
- another resin a resin not containing an ethylenically unsaturated bond group
- Other resins are blended, for example, in applications in which particles such as pigments are dispersed in a composition and applications in binders.
- grains, such as a pigment is also called a dispersing agent.
- such application of the resin is an example, and the resin can also be used for purposes other than such application.
- the weight average molecular weight (Mw) of the other resin is preferably 2,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, and more preferably 500000 or less. 3000 or more are preferable and, as for a lower limit, 5000 or more are more preferable.
- (meth) acrylic resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyether sulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamide Imide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, etc. may be mentioned.
- One of these resins may be used alone, or two or more thereof may be mixed and used.
- resins may have an acid group.
- an acid group a carboxyl group, a phosphoric acid group, a sulfo group, a phenolic hydroxyl group etc. are mentioned, for example, A carboxyl group is preferable.
- These acid groups may be of only one type, or of two or more types.
- the resin having an acid group can also be used as an alkali-soluble resin.
- a polymer having a carboxyl group in a side chain is preferable.
- alkali-soluble polymers such as methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, maleic acid copolymer, partially esterified maleic acid copolymer, novolac resin, etc.
- a phenolic resin, an acidic cellulose derivative having a carboxyl group in a side chain, and a resin obtained by adding an acid anhydride to a polymer having a hydroxy group are mentioned.
- copolymers of (meth) acrylic acid and other monomers copolymerizable therewith are suitable as the alkali-soluble resin.
- Other monomers copolymerizable with (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, vinyl compounds and the like.
- alkyl (meth) acrylate and aryl (meth) acrylate methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate, Hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, glycidyl (meth) acrylate, etc.
- vinyl compound examples include styrene, ⁇ -methylstyrene, vinyl toluene, acrylonitrile, vinyl acetate, N-vinyl pyrrolidone, polystyrene macromonomer, polymethyl methacrylate macromonomer and the like.
- maleimide monomers such as N-phenyl maleimide and N-cyclohexyl maleimide can also be used.
- These other monomers copolymerizable with (meth) acrylic acid may be only one type, or two or more types.
- Resin having an acid group is benzyl (meth) acrylate / (meth) acrylic acid copolymer, benzyl (meth) acrylate / (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate copolymer, benzyl (meth)
- a multicomponent copolymer consisting of acrylate / (meth) acrylic acid / other monomers can be preferably used. Further, those obtained by copolymerizing 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer described in JP-A No.
- the resin having an acid group is a polymer containing a repeating unit derived from a monomer component including the above-mentioned ether dimer.
- the resin having an acid group may contain a repeating unit derived from a compound represented by the following formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents an alkylene group having 2 to 10 carbon atoms
- R 3 has a hydrogen atom or 1 to 20 carbon atoms which may contain a benzene ring.
- Represents an alkyl group of n represents an integer of 1 to 15.
- the resin having an acid group is described in JP-A-2012-208494, paragraphs 0558 to 0571 (corresponding US patent application publication No. 2012/0235099, paragraphs 0685 to 0700), JP-A-2012-198408. No. 0076-0099 can be referred to, and the contents thereof are incorporated herein. Moreover, the resin which has an acidic radical can also use a commercial item.
- the acid value of the resin having an acid group is preferably 30 to 200 mg KOH / g.
- the lower limit is preferably 50 mg KOH / g or more, and more preferably 70 mg KOH / g or more.
- 150 mgKOH / g or less is preferable and 120 mgKOH / g or less of an upper limit is more preferable.
- resin which has an acidic radical resin of the following structure etc. are mentioned, for example.
- the coloring composition of the present invention can also contain a resin as a dispersant.
- the dispersant includes an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%. Resins consisting only of groups are more preferred.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group.
- the acid value of the acidic dispersant is preferably 40 to 105 mg KOH / g, more preferably 50 to 105 mg KOH / g, and still more preferably 60 to 105 mg KOH / g.
- a basic dispersing agent represents resin whose quantity of a basic group is larger than the quantity of an acidic radical.
- the basic dispersant is preferably a resin in which the amount of basic groups exceeds 50% by mole, where the total amount of the amount of acid groups and the amount of basic groups is 100% by mole.
- the basic group possessed by the basic dispersant is preferably an amino group.
- the resin used as the dispersant preferably contains a repeating unit having an acid group.
- the resin used as the dispersing agent contains a repeating unit having an acid group, it is possible to further reduce the residue generated on the base of the pixel when forming a pattern by photolithography.
- the resin used as the dispersant is preferably a resin containing a repeating unit having a graft chain in its side chain (hereinafter, also referred to as a graft resin).
- a graft chain means a polymer chain which branches and extends from the main chain of the repeating unit.
- the length of the graft chain is not particularly limited, but as the graft chain becomes longer, the steric repulsion effect becomes higher, and the dispersibility of the pigment etc. can be enhanced.
- the number of atoms excluding hydrogen atoms is preferably 40 to 10,000, and the number of atoms excluding hydrogen atoms is more preferably 50 to 2,000, and the number of atoms excluding hydrogen atoms is 60 to 60 More preferably, it is 500.
- the graft chain preferably includes at least one structure selected from polyester chains, polyether chains, poly (meth) acrylic chains, polyurethane chains, polyurea chains and polyamide chains, and polyester chains, polyether chains and poly (meta It is more preferable to include at least one structure selected from acryl chains, and it is further preferable to include a polyester chain.
- the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
- substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group having 5 to 24 carbon atoms or an alkoxy group is preferable.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, and linear or branched is preferable.
- graft resin resin of the following structure etc. are mentioned, for example. Further, the details of the graft resin can be referred to the description of Paragraph Nos. 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein.
- the resin used as the dispersant is also preferably an oligoimine resin containing a nitrogen atom in at least one of the main chain and the side chain.
- the oligoimine resin has a structural unit having a partial structure X having a functional group having a pKa of 14 or less and a side chain containing a side chain Y having 40 to 10,000 atoms, and at least a main chain and a side chain Resins having a basic nitrogen atom on one side are preferred.
- the basic nitrogen atom is not particularly limited as long as it exhibits basicity.
- the oligoimine resin the description in paragraphs [0102] to [0166] of JP-A-2012-255128 can be referred to, and the above contents are incorporated herein.
- Examples of the oligoimine resin include the following.
- the resins described in paragraph Nos. 0168 to 0174 of JP 2012-255128 A can be used.
- Dispersants are also available as commercial products, and specific examples thereof include the Disperbyk series (eg, Disperbyk-111 etc.) manufactured by BYK Chemie, the Solsperse series manufactured by Nippon Lubrizol Corporation (eg, And so forth).
- pigment dispersants described in paragraphs 0041 to 0130 of JP-A-2014-130338 can also be used, the contents of which are incorporated herein.
- resin which has an acidic radical mentioned above, a polymeric polymer, etc. can also be used as a dispersing agent.
- the resin demonstrated as the said dispersing agent can also be used for uses other than a dispersing agent. For example, it can also be used as a binder.
- the content of the other resin is preferably 1 to 50% by mass in the total solid content of the coloring composition of the present invention.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- the lower limit is preferably 3% by mass or more, and more preferably 5% by mass or more.
- the coloring composition of the present invention can be substantially free of other resins.
- the content of the other resins in the total solid content of the coloring composition of the present invention is preferably 0.1% by mass or less It is more preferable that it is 0.05 mass% or less, and it is especially preferable not to contain.
- the total content of the above-described compound having an ethylenically unsaturated bond group and another resin is preferably 5 to 50% by mass in the total solid content of the coloring composition of the present invention.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the upper limit is preferably 45% by mass or less, and more preferably 40% by mass or less.
- organic solvent examples include, for example, the following organic solvents.
- esters for example, ethyl acetate, n-butyl acetate, isobutyl acetate, cyclohexyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkyl alkyl oxyacetate alkylate (Eg, methyl alkyl oxyacetate, ethyl alkyl oxyacetate, butyl alkyl oxyacetate (eg, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate etc.), alkyl 3-alkyloxypropionate Esters (eg, methyl 3-alkyloxypropionate,
- 2-alkyloxypropionic acid alkyl esters eg methyl 2-alkyloxypropionate, ethyl 2-alkyloxypropionate, propyl 2-alkyloxypropionate etc.
- ethers for example, diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol Monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate and the like can be mentioned.
- a solvent having a low metal content as the solvent.
- the metal content in the solvent is preferably, for example, 10 parts by weight (pps) or less.
- a solvent having a metal content of mass ppt (parts per trillion) level may be used, and such a high purity solvent is provided by, for example, Toyo Gosei Co., Ltd. (Chemical Industry Journal, November 13, 2015) Day).
- As a method of removing impurities such as metal from the solvent for example, distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter can be mentioned.
- a filter hole diameter of a filter used for filtration 10 micrometers or less are preferred, 5 micrometers or less are more preferred, and 3 micrometers or less are still more preferred.
- the material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
- the solvent may contain isomers (compounds having the same number of atoms but different structures). Moreover, only one type of isomer may be contained, or two or more types may be contained.
- the content rate of a peroxide is 0.8 mmol / L or less, and it is more preferable that the organic solvent used by this invention does not contain a peroxide substantially.
- the content of the solvent is preferably such that the total solid content of the coloring composition is 5 to 40% by mass.
- the upper limit is preferably 35% by mass or less, and more preferably 30% by mass or less.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the coloring composition of the present invention preferably contains toluene and a solvent other than toluene, and the content of toluene is preferably 0.1 to 10 mass ppm.
- the upper limit of the content of toluene is preferably 9 mass ppm or less, more preferably 8 mass ppm or less, and still more preferably 7 mass ppm or less.
- the lower limit is preferably 0.2 mass ppm or more, more preferably 0.3 mass ppm or more, and still more preferably 0.4 mass ppm or more.
- solvents other than toluene methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclopentanone , Ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, propylene glycol methyl ether acetate, 3-methoxy-N, N-dimethylpropanamide and 3-butoxy-N, N-dimethylpropanamide It is preferably a species.
- the coloring composition of the present invention contains toluene as a solvent and a solvent other than toluene, and the content of toluene in the coloring composition is 0.1 to 10 mass ppm, a coloring composition is obtained. Even when the film obtained by using it is exposed to a high temperature and high humidity environment, the occurrence of foreign matter defects can be effectively suppressed. The reason why such an effect can be obtained is presumed to be as follows.
- the above-mentioned metal azo pigment used in the coloring composition of the present invention tends to aggregate in the coloring composition.
- the metal azo pigment when the content of nickel ion (Ni 2+ ) in the metal azo pigment is small or when the metal azo pigment does not contain nickel ion, it is presumed to be in an energetically unstable state, and the metal azo pigment is It tends to reaggregate more easily.
- a compound having an ethylenically unsaturated bonding group By blending a compound having an ethylenically unsaturated bonding group, reaggregation of the metal azo pigment can be suppressed during storage to suppress generation of relatively large aggregates, but very fine aggregates etc. are formed. There is something to do.
- Such a very small aggregate does not cause foreign matter defects immediately after film formation, but a film is formed by using a coloring composition in which such a very small aggregate is formed.
- the aforementioned aggregates contained in the film may become nuclei to cause foreign matter defects.
- toluene has a high affinity to this energetically unstable metal azo pigment, and when a predetermined amount of toluene is present in the coloring composition, the aggregation of the metal azo pigment is moderately relaxed (dissolution) (Aggregation), which is considered to suppress the formation of aggregates which may cause the generation of foreign matter in the film.
- content of toluene is 0.1 mass ppm or more, the above-mentioned effect of deaggregation is fully acquired.
- the metal azo pigment when the metal azo pigment is too deaggregated, many unstable fine particles will be present in the coloring composition, and it is presumed that such fine particles are agglomerated due to film formation and the like to generate a lot of agglomerates.
- the content of toluene is 10 mass ppm or less, it is presumed that the above deaggregation effect is appropriately developed, and the aggregation of the metal azo pigment can be moderately loosened.
- the coloring composition of the present invention preferably further contains a photopolymerization initiator.
- a photopolymerization initiator There is no restriction
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- a halogenated hydrocarbon derivative for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- an acylphosphine compound for example, a hexaarylbiimidazole, an oxime compound, an organic peroxide, Thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxy ketone compounds, ⁇ -amino ketone compounds and the like
- an organic peroxide for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- an acylphosphine compound for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- an acylphosphine compound for example, a compound having a triazine skeleton, a compound having an oxadiazole skeleton, etc.
- the photopolymerization initiator is a trihalomethyl triazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxy ketone compound, an ⁇ -amino ketone compound, an acyl phosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a triaryl imidazole from the viewpoint of exposure sensitivity.
- Dimers, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyl oxadiazole compounds and 3-aryl substituted coumarin compounds are preferred, and oxime compounds, ⁇ -hydroxy ketone compounds, ⁇ -hydroxy ketone compounds More preferred are compounds selected from amino ketone compounds and acyl phosphine compounds, and more preferred are oxime compounds.
- an oxime compound as the photopolymerization initiator, excellent curability can be obtained.
- a film in which defects are more suppressed can be manufactured.
- Examples of commercially available ⁇ -hydroxy ketone compounds include IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, IRGACURE-127 (manufactured by BASF Corporation) and the like.
- Examples of commercially available ⁇ -amino ketone compounds include IRGACURE-907, IRGACURE-369, IRGACURE-379, and IRGACURE-379EG (manufactured by BASF Corporation).
- Examples of commercially available products of acyl phosphine compounds include IRGACURE-819, DAROCUR-TPO (all manufactured by BASF Corp.) and the like.
- Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-80068, the compounds described in JP-A-2006-342166, and the like.
- C. S. Perkin II (1979, pp. 1653-1660) a compound described in J. Am. C. S. A compound described in Perkin II (1979, pp. 156-162), a compound described in Journal of Photopolymer Science and Technology (1995, pp.
- IRGACURE-OXE01, IRGACURE-OXE02, IRGACURE-OXE03 and IRGACURE-OXE04 are also suitably used.
- TRONLY TR-PBG-304, TRONLY TR-PBG-309, TRONLY TR-PBG-305 (made by CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO., LTD.), Adeka ARKules NCI-930 And Adeka Optomer N-1919 (photopolymerization initiator 2 of JP 2012-14052 A) (all manufactured by ADEKA Co., Ltd.).
- oxime compounds other than those described above compounds described in JP-T-2009-519904, in which an oxime is linked to the N-position of a carbazole ring, and compounds described in US Pat. No. 7,626,957, in which a hetero substituent is introduced in the benzophenone moiety
- compounds described in JP-A-2010-15025 and U.S. Patent Publication 2009-292039 in which a nitro group is introduced at a dye site, a ketoxime compound described in WO2009 / 131189, the same triazine skeleton and oxime skeleton.
- the compound described in US Pat. No. 7,556,910 contained in the molecule the compound described in JP 2009-221114 A having maximum absorption at 405 nm and good sensitivity to a g-line light source are used. Good.
- an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring can also be used as a photopolymerization initiator.
- an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring
- the compound described in International Publication WO 2013/083505 can be mentioned.
- an oxime compound having a fluorine atom can also be used as a photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom include the compounds described in JP-A-2010-262028, the compounds 24 and 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. And the like (C-3) and the like. This content is incorporated herein.
- an oxime compound having a nitro group can be used as a photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- specific examples of the oxime compound having a nitro group compounds described in paragraphs 0031 to 0047 of JP 2013-114249 A, paragraphs 0008 to 0012 and 0070 to 0079 of JP 2014-137466 A, and patents
- the compounds described in Paragraph Nos. 0007 to 0025 of JP-A-4223071 and Adeka ARKLS NCI-831 may, for example, be mentioned.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited thereto.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the range of 360 to 480 nm. Moreover, the oxime compound is preferably a compound having a high absorbance at 365 nm and 405 nm.
- the molar absorption coefficient of the oxime compound at 365 nm or 405 nm is preferably 1,000 to 300,000, more preferably 2,000 to 300,000, and 5,000 to 200, Particularly preferred is 000.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using an ethyl acetate solvent with a UV-visible spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher functional photopolymerization initiator may be used as the photopolymerization initiator.
- a photopolymerization initiator paragraph Nos. 0417 to 0412 of JP-A-2010-527339, JP-A-2011-524436, International Publication WO2015 / 004565, JP-A-2016-532675.
- the content of the oxime compound is preferably 1 to 200 parts by mass with respect to 100 parts by mass of the metal azo pigment described above.
- the lower limit is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more.
- the upper limit is preferably 100 parts by mass or more, and more preferably 80 parts by mass or less. According to this aspect, the effects of the present invention described above tend to be obtained more significantly.
- the coloring composition of this invention may contain only 1 type of photoinitiator, and may contain 2 or more types. When 2 or more types of photoinitiators are included, it is preferable that the total amount of them becomes said range.
- the coloring composition of the present invention preferably further contains a pigment derivative.
- a pigment derivative includes compounds having a structure in which a part of the pigment is substituted with an acid group, a basic group or a phthalimide group.
- an acidic pigment derivative, a basic pigment derivative, a neutral pigment derivative and the like can be mentioned, and a basic pigment derivative is preferable.
- the pigment derivative is preferably a compound represented by the following formula (syn1).
- P represents a dye structure
- L represents a single bond or a linking group
- X represents an acid group, a basic group or a phthalimide group
- m represents an integer of 1 or more
- n is 1 or more
- the plurality of L and X may be different from each other, and when n is 2 or more, the plurality of X may be different from each other.
- L represents a single bond or a linking group, and preferably represents a linking group.
- the divalent linking group include an alkylene group, an arylene group, a nitrogen-containing heterocyclic group, -O-, -S-, -NR'-, -CO-, -COO-, -OCO-, -SO 2 -or The group which consists of these combination is mentioned, It is preferable that it is group containing an alkylene group or an alkylene group.
- R ′ represents a hydrogen atom, an alkyl group or an aryl group.
- L is a trivalent or higher linking group
- groups in which one or more hydrogen atoms have been removed from the above-described divalent linking group may be mentioned.
- the carbon number of the alkylene group is preferably 1 to 30, more preferably 1 to 15, and still more preferably 1 to 10.
- the alkylene group may have a substituent.
- the alkylene group may be linear, branched or cyclic.
- the cyclic alkylene group may be either monocyclic or polycyclic.
- the carbon number of the arylene group is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10.
- the nitrogen-containing heterocyclic group is preferably a 5- or 6-membered ring.
- the nitrogen-containing heterocyclic group is preferably a single ring or a fused ring, more preferably a single ring or a fused ring having 2 to 8 rings, and still more preferably a single ring or a fused ring having 2 to 4 rings.
- the number of nitrogen atoms contained in the nitrogen-containing heterocyclic group is preferably 1 to 3, and more preferably 1 to 2.
- the nitrogen-containing heterocyclic group may contain hetero atoms other than nitrogen atoms. As a hetero atom other than a nitrogen atom, an oxygen atom and a sulfur atom are illustrated, for example.
- the number of hetero atoms other than nitrogen atom is preferably 0 to 3, and more preferably 0 to 1.
- the nitrogen-containing heterocyclic group includes piperazine ring, pyrrolidine ring, pyrrole ring, piperidine ring, pyridine ring, imidazole ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, pyrazine ring and morpholine ring Group, thiazine ring group, indole ring group, isoindole ring group, benzimidazole ring group, purine ring group, quinoline ring group, isoquinoline ring group, quinoxaline ring group, cinnoline ring group, carbazole ring group and the following formula (L-1 And groups represented by (L-7) to (L-7). * In the formula represents a connecting hand.
- R represents a hydrogen atom or a substituent. Examples of the substituent include the above-mentioned substituent T.
- R 100 to R 106 each independently represent a hydrogen atom, an alkyl group, an alkenyl group or an aryl group, and R 100 and R 101 And may be linked to each other to form a ring.
- the alkyl group represented by R 100 to R 106 may be linear, branched or cyclic.
- the carbon number of the linear alkyl group is preferably 1 to 20, more preferably 1 to 12, and still more preferably 1 to 8.
- the carbon number of the branched alkyl group is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 8.
- the cyclic alkyl group may be monocyclic or polycyclic.
- the carbon number of the cyclic alkyl group is preferably 3 to 20, more preferably 4 to 10, and still more preferably 6 to 10.
- the carbon number of the alkenyl group represented by R 100 to R 106 is preferably 2 to 10, more preferably 2 to 8, and still more preferably 2 to 4.
- the number of carbon atoms of the aryl group R 100 ⁇ R 106 represents preferably has 6 to 18, more preferably 6 to 14, more preferably 6 to 10.
- R 100 and R 101 may be linked to each other to form a ring.
- the ring may be alicyclic or aromatic.
- the ring may be a single ring or may be a fused ring.
- As a linking group when R 100 and R 101 combine to form a ring a divalent group selected from the group consisting of -CO-, -O-, -NH-, a divalent aliphatic group and a combination thereof And a linking group of It is preferred that R 100 and R 101 do not form a ring.
- Each of R 100 and R 101 preferably independently represents an alkyl group or an aryl group, and more preferably an alkyl group.
- the alkyl group is preferably a linear or branched alkyl group, more preferably a linear alkyl group.
- m is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 2.
- n is preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
- the pigment derivative is preferably a compound represented by the formula (syn2).
- Rp 1 represents an alkyl group or an aryl group
- Rp 2 represents a group consisting of a single bond, -NR-, -CO-, -CO 2- , -SO 2- , -O-, -S- or a combination thereof
- R represents a hydrogen atom or an alkyl group Or an aryl group
- B 1 represents a single bond or a (t + 1) -valent linking group
- C 1 represents a group consisting of a single bond, -NR-, -CO-, -CO 2- , -SO 2- , -O-, -S- or a combination thereof
- R represents a hydrogen atom or an alkyl group Or an aryl group
- D 1 represents a single bond, an alkylene group or an arylene group
- E 1 represents an acid group, a basic group or a phthalimido group.
- t represents an integer
- Rp 1 is preferably a methyl group or a phenyl group, and most preferably a methyl group.
- Rp 2 represents a group consisting of a single bond, -NR-, -CO-, -CO 2- , -SO 2- , -O-, -S- or a combination thereof, and R represents a hydrogen atom or an alkyl group Or an aryl group.
- the alkyl group represented by R may be linear, branched or cyclic, and is preferably linear or branched.
- the carbon number of the alkyl group is preferably 1 to 10, and more preferably 1 to 5.
- the carbon number of the aryl group represented by R is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 12.
- R is preferably a hydrogen atom.
- Rp 2 is, -NRCO -, - CONR -, - SO 2 NR- , or -NRSO 2 - are preferred, -NRCO- or
- Examples of the (t + 1) -valent linking group represented by B 1 include the linking groups described for L in formula (syn1), and preferred are linking groups represented by the following formulas (PA-4) to (PA-9) . * Represents a junction with Rp 2 and C 1 .
- C 1 is, -NR -, - NRCO -, - CONR -, - SO 2 NR-, or, -NRSO 2 - are preferred, -NR -, - NRCO- or -CONR- is preferred.
- R represents a hydrogen atom, an alkyl group or an aryl group. Preferred ranges of the alkyl group and aryl group represented by R are the same as the ranges described above. R is preferably a hydrogen atom.
- D 1 represents a single bond, an alkylene group or an arylene group, and is preferably an alkylene group.
- the carbon number of the alkylene group is preferably 1 to 30, more preferably 1 to 15, and still more preferably 1 to 10.
- the alkylene group may have a substituent.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
- E 1 represents an acid group, a basic group or a phthalimido group.
- the acid group and the basic group those described for X in formula (syn1) can be mentioned.
- E 1 is preferably a basic group, more preferably a group represented by formula (X-3).
- T is preferably 1 or 2, and more preferably 2.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the pigment contained in the coloring composition.
- the pigment derivative may use only 1 type and may use 2 or more types together.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the metal azo pigment.
- the pigment derivative may use only 1 type and may use 2 or more types together.
- the coloring composition of the present invention may contain a curing accelerator for the purpose of improving the hardness of the pattern or for the purpose of lowering the curing temperature.
- the curing accelerator include thiol compounds.
- the polyfunctional thiol compound As a thiol compound, the polyfunctional thiol compound etc. which have a 2 or more mercapto group in a molecule
- the polyfunctional thiol compound may be added for the purpose of improving the stability, the odor, the resolution, the developability, the adhesion and the like.
- the polyfunctional thiol compound is preferably a secondary alkanethiol, and more preferably a compound having a structure represented by the following formula (T1).
- T1 In formula (T1), n represents an integer of 2 to 4, and L represents a divalent to tetravalent linking group.
- L is preferably an aliphatic group having 2 to 12 carbon atoms.
- n is 2 and L is an alkylene group having 2 to 12 carbon atoms.
- Specific examples of the polyfunctional thiol compound include compounds represented by the following structural formulas (T2) to (T4), and a compound represented by formula (T2) is preferable.
- One type of thiol compound may be used, or two or more types may be used in combination.
- methylol compounds for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example, compounds exemplified as a crosslinking agent in paragraph 0246 of JP-A-2015-34963
- amines for example,
- the content of the curing accelerator is preferably 0.3 to 8.9% by mass in the total solid content of the coloring composition, and is 0.8 to 6.4. % By mass is more preferred.
- the coloring composition of the present invention preferably contains a surfactant.
- a surfactant various surfactants such as fluorinated surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, silicone surfactants can be used to further improve the coating property. Fluorinated surfactants are preferred because they can be used.
- liquid properties when prepared as a coating liquid can be improved, and uniformity of coating thickness can be further improved. That is, in the case of film formation using a coating solution to which a coloring composition containing a fluorine-based surfactant is applied, the interfacial tension on the surface of the coating film is reduced, and the uniformity of drying is improved. For this reason, film formation with few coating nonuniformity can be performed more suitably.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- the fluorine-based surfactant having a fluorine content in the above range is effective in terms of the uniformity of the thickness of the coating film and the liquid saving property, and the solubility in the coloring composition is also good.
- fluorine-based surfactants for example, Megafac F171, F172, F173, F176, F177, F141, F142, F143, R304, F437, F475, F479, F482, F554, F780 (all, DIC Corporation) , Florard FC430, FC431, FC171 (above, Sumitomo 3M Co., Ltd.), Surfron S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC -383, S-393, KH-40 (all, manufactured by Asahi Glass Co., Ltd.), PF636, PF656, PF6320, PF6520, PF7002 (all, manufactured by OMNOVA) and the like.
- fluorine-based surfactant compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327, and compounds described in paragraphs 0117 to 0132 of JP-A-2011-132503 can also be used.
- the fluorine-based surfactant is a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cleaved when heat is applied and the fluorine atom is volatilized can also be suitably used.
- a fluorochemical surfactant Megafuck DS series (Chemical Chemical Daily, February 22, 2016) manufactured by DIC Corporation (Nikkei Sangyo Shimbun, February 23, 2016), for example, Megafuck DS -21 can be mentioned.
- fluorinated surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorinated surfactant.
- fluorine-based surfactants can be referred to the description of JP-A-2016-216602, the contents of which are incorporated herein.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy and propyleneoxy) (meth)
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the following compounds are also exemplified as the fluorinated surfactant used in the present invention. In the following formulas,% indicating the proportion of repeating units is mol%.
- the weight average molecular weight of the above-mentioned compounds is preferably 3,000 to 50,000, for example, 14,000.
- a fluorine-containing polymer having an ethylenically unsaturated group in the side chain can also be used as the fluorine-based surfactant.
- Specific examples thereof include compounds described in paragraph Nos. 0050 to 0090 and paragraphs 0289 to 0295 of JP-A-2010-164965.
- Examples of commercially available products include Megafac RS-101, RS-102, RS-718-K, RS-72-K and the like manufactured by DIC Corporation.
- nonionic surfactants glycerol, trimethylolpropane, trimethylolethane and ethoxylates and propoxylates thereof (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF Company), Tetronics 304, 701, 704, 901, 904, 150R1 (BA).
- BA nonionic surfactants
- KP-341 manufactured by Shin-Etsu Chemical Co., Ltd.
- Polyflow No. 1 75, no. 90, no. 95
- W001 manufactured by Yusho Co., Ltd.
- anionic surfactant examples include W004, W005, W017 (manufactured by Yusho Co., Ltd.), Sandet BL (manufactured by Sanyo Kasei Co., Ltd.), and the like.
- silicone type surfactant for example, Toray silicone DC3PA, Toray silicone SH7PA, Toray silicone DC11PA, Toray silicone SH21PA, Toray silicone SH28PA, Toray silicone SH29PA, Toray silicone SH30PA, Toray silicone SH8400 (more than Toray Dow Corning ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, Momentive Performance Materials Co., Ltd.), KP-341, KF6001, KF6002 (above, Shin-Etsu Silicone Co., Ltd.) Made, BYK 307, BYK 323, BYK 330 (above, made by Big Chemie Co., Ltd.), etc. are mentioned.
- the content of the surfactant is preferably 0.001 to 5% by mass in the total solid content of the coloring composition. 3 mass% or less is preferable, and, as for the upper limit, 1 mass% or less is more preferable. 0.05 mass% or more is preferable, and, as for a lower limit, 0.01 mass% or more is more preferable. Only one surfactant may be used, or two or more surfactants may be combined. When two or more kinds are contained, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber conjugated diene compounds, aminobutadiene compounds, methyldibenzoyl compounds, coumarin compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyl triazine compounds and the like can be used. The details of these can be referred to the descriptions of paragraphs 0052 to 0072 of JP 2012-208374 A and paragraphs 0317 to 0334 of JP 2013-68814 A, the contents of which are incorporated herein.
- Specific examples of the ultraviolet absorber include compounds having the following structure.
- UV-503 manufactured by Daito Kagaku Co., Ltd.
- MYUA series Chemical Industry Daily, February 1, 2016 made by Miyoshi Yushi may be used.
- the content of the UV absorber is preferably 0.1 to 10% by mass, and more preferably 0.1 to 5% by mass in the total solid content of the coloring composition. More preferably, 0.1 to 3% by mass is particularly preferable.
- an ultraviolet absorber may use only 1 type and may use 2 or more types. When 2 or more types of ultraviolet absorbers are contained, it is preferable that the total amount of them becomes the said range.
- the coloring composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group is a substituent which is directly bonded to a silicon atom and can form a siloxane bond by hydrolysis reaction and / or condensation reaction.
- a hydrolysable group a halogen atom, an alkoxy group, an acyloxy group etc. are mentioned, for example.
- the silane coupling agent includes at least one group selected from a vinyl group, an epoxy group, a styrene group, a methacryl group, an amino group, an isocyanurate group, an ureido group, a mercapto group, a sulfide group, and an isocyanate group, and an alkoxy group.
- the silane compound which has and is preferable.
- silane coupling agent examples include, for example, N- ⁇ -aminoethyl- ⁇ -aminopropylmethyl dimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-602), N- ⁇ -aminoethyl- ⁇ -aminopropyl tri- trile Methoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., KBE-602), ⁇ -aminopropyltrimethoxysilane (Shin-Etsu Chemical) Manufactured by Kogyo Co., Ltd., KBM-903), ⁇ -aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., KBE-903), 3-methacryloxypropyltrime
- the content of the silane coupling agent is preferably 0.001 to 20% by mass, and 0.01 to 10% by mass in the total solid content of the coloring composition. % Is more preferable, and 0.1 to 5% by mass is particularly preferable.
- the coloring composition of the present invention may contain only one type of silane coupling agent, or may contain two or more types. When 2 or more types of silane coupling agents are contained, it is preferable that the total amount of them becomes the said range.
- the coloring composition of the present invention preferably contains a polymerization inhibitor.
- a film in which defects are more suppressed can be produced even when the coloring composition is stored for a long time under a low temperature environment.
- the coloring composition of the present invention contains a polymerization inhibitor, the content of the polymerization inhibitor is preferably 0.0001 to 1% by mass in the coloring composition.
- the coloring composition of the present invention may contain only one type of polymerization inhibitor, or may contain two or more types. When two or more types of polymerization inhibitors are contained, the total amount thereof is preferably in the above range.
- additives such as a filler, an adhesion promoter, an antioxidant, a latent antioxidant, a thermal polymerization initiator and the like can be blended, if necessary.
- these additives include the additives described in paragraphs [0155] to [0156] of JP-A-2004-295116, the contents of which are incorporated herein.
- the antioxidant for example, a phenol compound, a phosphorus compound (for example, a compound described in paragraph 0042 of JP-A-2011-90147), a thioether compound or the like can be used.
- a latent antioxidant is a compound in which the site that functions as an antioxidant is protected with a protecting group, and is heated at 100 to 250 ° C., or heated at 80 to 200 ° C. in the presence of an acid / base catalyst. In some cases, compounds in which the protective group is eliminated to function as an antioxidant can be mentioned. Examples of the latent antioxidant include compounds described in International Publication WO 2014/021023, International Publication WO 2017/030005, and Japanese Unexamined Patent Publication No.
- Examples of commercially available products include Adeka ARKRUZ GPA-5001 (manufactured by ADEKA Co., Ltd.) and the like.
- a thermal polymerization initiator a pinacol compound, an organic peroxide, an azo compound etc. are mentioned, A pinacol compound is preferable.
- pinacol compounds benzopinacol, 1,2-dimethoxy-1,1,2,2-tetraphenylethane, 1,2-diethoxy-1,1,2,2-tetraphenylethane, 1,2-diphenoxy- 1,1,2,2-tetraphenylethane, 1,2-dimethoxy-1,1,2,2-tetra (4-methylphenyl) ethane, 1,2-diphenoxy-1,1,2,2-tetra (4-Methoxyphenyl) ethane, 1,2-bis (trimethylsiloxy) -1,1,2,2-tetraphenylethane, 1,2-bis (triethylsiloxy) -1,1,2,2-tetraphenyl Ethane, 1,2-bis (t-butyldimethylsiloxy) -1,1,2,2-tetraphenylethane, 1-hydroxy-2-trimethylsiloxy-1,1,2,2-tetraphenyl Ethane, 1-hydroxy-2-triethylsiloxy-1,1,2,2-tetraphenylethan
- JP-A-2014-521772, JP-A-2014-523939, and JP-A-2014-521772 can be referred to, and the contents thereof are incorporated in the present specification.
- the water content of the coloring composition of the present invention is preferably 3% by mass or less, more preferably 0.01 to 1.5% by mass, and 0.1 to 1.0% by mass More preferable.
- the moisture content of the coloring composition can be measured by the Karl Fischer method.
- the solid content concentration of the coloring composition of the present invention is preferably 5 to 40% by mass.
- the upper limit is preferably 35% by mass or less, and more preferably 30% by mass or less.
- the lower limit is preferably 8% by mass or more, and more preferably 10% by mass or more.
- the coloring composition of the present invention can be used with its viscosity adjusted for the purpose of adjusting the film surface state (flatness and the like), adjusting the film thickness, and the like.
- the value of viscosity can be appropriately selected as necessary, and for example, 0.3 to 50 mPa ⁇ s at 25 ° C. is preferable, and 0.5 to 20 mPa ⁇ s is more preferable.
- As a method of measuring the viscosity for example, using a Toki Sangyo viscometer RE85L (rotor: 1 ° 34 ′ ⁇ R24, measurement range 0.6 to 1200 mPa ⁇ s) and performing temperature control at 25 ° C. It can be measured.
- a storage container of the coloring composition of this invention A well-known storage container can be used.
- a container for the purpose of suppressing the mixing of impurities into the raw materials and the composition, a multilayer bottle in which the inner wall of the container is composed of six types and six layers of resin or a bottle in which six types of resin are seven layers It is also preferred to use.
- a container for example, the container described in JP-A-2015-123351 can be mentioned.
- the coloring composition of the present invention can be preferably used as a coloring composition for a solid-state imaging device. More specifically, it can be preferably used as a coloring composition for forming a pixel of a color filter used for a solid-state imaging device.
- the coloring composition of the present invention can be prepared by mixing the above-mentioned components.
- all the components may be simultaneously dissolved and / or dispersed in a solvent to prepare a coloring composition, and if necessary, each component may be used as two or more solutions or dispersions as appropriate. Alternatively, they may be mixed at the time of use (at the time of application) to prepare a coloring composition.
- mechanical force used to disperse the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and the dispersing machine for dispersing the pigment are the dispersion technology and industrial application centering on “Dispersion Technology Complete, Information Technology Co., Ltd. issued July 15, 2005” and “suspension (solid / liquid dispersion system)” The process and the dispersing machine described in Paragraph No.
- the particles may be subjected to a refinement treatment in a salt milling step.
- the materials, equipment, processing conditions and the like used in the salt milling step can be referred to, for example, the descriptions of JP-A-2015-194521 and JP-A-2012-04629.
- a filter for the purpose of the removal of a foreign material, reduction of a defect, etc.
- a filter if it is a filter conventionally used for filtration applications etc., it can be used, without being limited in particular.
- a fluorine resin such as polytetrafluoroethylene (PTFE), a polyamide resin such as nylon (for example, nylon-6, nylon-6, 6), a polyolefin resin such as polyethylene or polypropylene (PP) (high density and / or super
- PP polypropylene
- a filter using a material such as a high molecular weight polyolefin resin can be mentioned.
- polypropylene including high density polypropylene
- nylon are preferable.
- the pore diameter of the filter is suitably about 0.01 to 7.0 ⁇ m, preferably about 0.01 to 3.0 ⁇ m, and more preferably about 0.05 to 0.5 ⁇ m.
- the filter using a fiber-like filter medium as a filter.
- the fibrous filter medium include polypropylene fiber, nylon fiber, glass fiber and the like.
- Specific examples of the filter using a fiber-like filter medium include filter cartridges of SBP type series (SBP 008, etc.), TPR type series (TPR 002, TPR 005, etc.), and SHPX type series (SHPX 003, etc.) manufactured by Loki Techno. .
- filters When using filters, different filters may be combined. In that case, filtration with each filter may be performed only once or may be performed twice or more. For example, filters of different pore sizes may be combined within the range described above.
- the pore size here can refer to the nominal value of the filter manufacturer.
- filters for example, it is possible to select from various filters provided by Nippon Pall Co., Ltd. (DFA 4201 NIEY, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. can do.
- filtration with a 1st filter may be performed only with a dispersion liquid, and you may filter with a 2nd filter, after mixing other components.
- the second filter one formed of the same material as the first filter can be used.
- the film of the present invention can be produced through the step of applying the above-mentioned colored composition of the present invention onto a support. It is preferable that the method for producing a film of the present invention further includes the step of forming a pattern. Examples of the method of forming a pattern include photolithography and dry etching.
- the pattern formation by photolithography includes the steps of forming a colored composition layer on a support using a colored composition, exposing the colored composition layer in a pattern, and unexposed areas of the colored composition layer. And the step of removing by development to form a pattern. If necessary, a step of baking the colored composition layer (pre-baking step) and a step of baking the developed pattern (post-baking step) may be provided.
- a colored composition layer is formed on a support using a colored composition, and the colored composition layer is cured to form a cured product layer;
- the method includes the steps of forming a resist layer, patterning the resist layer to obtain a resist pattern, and dry etching the cured product layer using the resist pattern as an etching mask to form a pattern. Each step will be described below.
- the colored composition is used to form a colored composition layer on a support.
- a support body There is no limitation in particular as a support body, According to a use, it can select suitably.
- a glass substrate, a silicon substrate, etc. are mentioned, It is preferable that it is a silicon substrate.
- a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CMOS complementary metal oxide semiconductor
- a black matrix may be formed on the silicon substrate to separate each pixel.
- a subbing layer may be provided on the silicon substrate for the purpose of improving the adhesion with the upper layer, preventing the diffusion of substances or flattening the surface of the substrate.
- a publicly known method can be used as a method of applying the coloring composition.
- dropping method drop casting
- slit coating method spraying method
- roll coating method spin coating method
- cast coating method slit and spin method
- pre-wet method for example, JP 2009-145395A
- Ink jet for example, on-demand method, piezo method, thermal method
- discharge system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, etc.
- the application method in the inkjet is not particularly limited, and for example, the method (in particular, page 115-) disclosed in "Spread and usable inkjet-unlimited possibilities in patents-published in February 2005, resident Betechno Research" Methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, etc. It can be mentioned. Moreover, regarding the application method of the coloring composition, the descriptions of International Publication WO 2017/030174 and International Publication WO 2017/018419 can be referred to, and the contents thereof are incorporated in the present specification.
- the colored composition layer formed on the support may be dried (prebaked).
- the prebaking may not be performed.
- the prebaking temperature is preferably 150 ° C. or less, more preferably 120 ° C. or less, and still more preferably 110 ° C. or less.
- the lower limit may be, for example, 50 ° C. or more, and may be 80 ° C. or more.
- the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and still more preferably 80 to 220 seconds. Prebaking can be performed with a hot plate, an oven, or the like.
- ⁇ exposure step the colored composition layer is exposed in a pattern (exposure step).
- pattern exposure can be performed by exposing the coloring composition layer through a mask having a predetermined mask pattern using a stepper exposure device, a scanner exposure device, or the like. Thereby, the exposed portion can be cured.
- radiation (light) that can be used for exposure include g-rays and i-rays. Further, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
- Examples of light having a wavelength of 300 nm or less include KrF rays (wavelength 248 nm), ArF rays (wavelength 193 nm), and the like, and KrF rays (wavelength 248 nm) are preferable.
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to being performed under the atmosphere, for example, under a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially It may be exposed with no oxygen, and may be exposed under a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
- the exposure intensity is can be set appropriately, usually 1000W / m 2 ⁇ 100000W / m 2 ( e.g., 5000W / m 2, 15000W / m 2, or, 35000W / m 2) selected from the range of Can.
- Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed area of the colored composition layer is removed by development to form a pattern.
- the development removal of the unexposed part of a coloring composition layer can be performed using a developing solution.
- the colored composition layer in the unexposed area in the exposure step is eluted into the developer, and only the photocured area remains.
- As the developing solution an organic alkaline developing solution which does not cause damage to underlying elements or circuits is desirable.
- the temperature of the developing solution is preferably, for example, 20 to 30.degree.
- the development time is preferably 20 to 180 seconds.
- the process of shaking off the developer every 60 seconds and supplying the developer anew may be repeated several times.
- an alkaline aqueous solution obtained by diluting an alkaline agent with pure water is preferably used.
- the alkaline agent include aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide and tetrabutylammonium hydroxide.
- Organic alkaline compounds such as benzyl, trimethyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -7-undecene, or water Inorganic materials such as sodium oxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, sodium metasilicate Potassium compounds may be mentioned.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, and more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the surfactant mentioned above is mentioned and nonionic surfactant is preferable.
- the developer may be prepared once as a concentrate and diluted to a concentration required for use, from the viewpoint of transportation and storage convenience.
- the dilution ratio is not particularly limited, but can be set, for example, in the range of 1.5 to 100 times.
- clean (rinse) when using the developing solution which consists of such alkaline aqueous solution, it is preferable to wash
- Post-baking is a heat treatment after development to complete curing, and the heating temperature is preferably 100 to 240 ° C., and more preferably 200 to 240 ° C., for example.
- Post-baking can be carried out continuously or batchwise using a heating means such as a hot plate, convection oven (hot air circulating dryer), high frequency heater or the like so that the film after development is under the above conditions.
- the post-baking film preferably has a Young's modulus of 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- the film have high flatness.
- the surface roughness Ra is preferably 100 nm or less, more preferably 40 nm or less, and still more preferably 15 nm or less.
- the lower limit is not defined, but is preferably, for example, 0.1 nm or more.
- the surface roughness can be measured, for example, using an AFM (atomic force microscope) Dimension 3100 manufactured by Veeco.
- the contact angle of water of the membrane can be appropriately set to a preferable value, but typically, it is in the range of 50 to 110 °.
- the contact angle can be measured, for example, using a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.).
- the volume resistivity of each pattern (pixel) be high.
- the volume resistivity of the pixel is preferably 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more.
- the upper limit is not specified, but is preferably 10 14 ⁇ ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured, for example, using an ultra-high resistance meter 5410 (manufactured by Advantest Corporation).
- Patterning by dry etching is performed by applying a coloring composition onto a support to cure the formed coloring composition layer to form a cured product layer, and then a resist layer patterned on the cured product layer. And then dry etching the cured product layer using the patterned resist layer as a mask.
- the resist layer is preferably formed by applying a positive or negative photosensitive composition on the cured product layer and drying it. As a composition used for formation of a resist layer, a positive photosensitive composition is preferable.
- photosensitive compositions sensitive to radiation such as ultraviolet (g-ray, h-ray, i-ray), far-ultraviolet radiation including KrF radiation, ArF radiation and the like, electron beam, ion beam and X-ray are preferred.
- the above-mentioned positive photosensitive composition is preferably a photosensitive composition sensitive to KrF ray, ArF ray, i ray, X ray), and from the viewpoint of fine processability, the photosensitive composition sensitive to KrF ray is more preferable preferable.
- positive photosensitive composition positive resist compositions described in JP-A-2009-237173 and JP-A-2010-134283 are suitably used.
- the color filter of the present invention comprises the film of the present invention described above.
- the color filter in the present invention can be used for a solid-state imaging device such as a CCD (charge coupled device) or a CMOS (complementary metal oxide semiconductor) or an image display device.
- CCD charge coupled device
- CMOS complementary metal oxide semiconductor
- the solid-state imaging device of the present invention has a film using the above-mentioned coloring composition of the present invention.
- the configuration of the solid-state imaging device is not particularly limited as long as it functions as a solid-state imaging device, and examples thereof include the following configurations.
- the substrate there are a plurality of photodiodes forming the light receiving area of a solid-state imaging device (CCD (charge coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and transfer electrodes made of polysilicon etc.
- CCD charge coupled device
- CMOS complementary metal oxide semiconductor
- Device protective film formed of silicon nitride or the like formed on the light shielding film so as to cover the entire surface of the light shielding film and the photodiode light receiving portion. And has a color filter on the device protection film.
- the device has a light collecting means (for example, a micro lens etc., hereinafter the same) on the device protective film and under the color filter (closer to the substrate) or a structure having the light collecting means on the color filter It may be.
- the color filter may have a structure in which a cured film forming each colored pixel is embedded in a space partitioned into, for example, a grid shape by partition walls.
- the partition walls in this case preferably have a low refractive index for each colored pixel.
- an imaging device having such a structure devices described in JP 2012-227478 A and JP 2014-179577 A can be mentioned.
- An imaging apparatus provided with this solid-state imaging device can be used as an on-vehicle camera or a surveillance camera as well as a digital camera and an electronic device (such as a mobile phone) having an imaging function.
- the image display apparatus of the present invention has a film using the above-mentioned coloring composition of the present invention.
- the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the image display device and details of each image display device for example, “Electronic display device (authored by Akio Sasaki, Inc., Industrial Research Association, published in 1990)”, “Display device (authored by Ibuki, industrial book ( Co., Ltd., published in Heisei 1973).
- the liquid crystal display device is described, for example, in "Next-generation liquid crystal display technology (edited by Tatsuo Uchida, Industrial Research Association, Inc., 1994)".
- the aqueous solution of potassium hydroxide was added to the solution after the heat treatment to adjust the pH to about 5.
- the pigment was then isolated from the solution on a suction filter, washed, dried in a vacuum drying cabinet at 80 ° C. and then ground in a standard laboratory mill for about 2 minutes to produce metal azo pigment 1.
- the aqueous solution of potassium hydroxide was added to the solution after the heat treatment to adjust the pH to about 5.
- the pigment was then isolated from the solution on a suction filter, washed, dried in a vacuum drying cabinet at 80 ° C. and then ground in a standard laboratory mill for about 2 minutes to produce metal azo pigment 3.
- the solution to which these were added was maintained at 82 ° C. for 3 hours, and then KOH was added to adjust the pH to about 5.5. Then, the temperature of the solution was raised to 90 ° C., and while maintaining the temperature of 90 ° C., 1000 g of distilled water was added for dilution. Subsequently, 113 g of 30% hydrochloric acid was added dropwise to this solution, and then heat treated at a temperature of 90 ° C. for 12 hours. Subsequently, the aqueous solution of potassium hydroxide was added to the solution after the heat treatment to adjust the pH to about 5. The pigment was then isolated from the solution on a suction filter, washed, dried in a vacuum drying cabinet at 80 ° C. and then ground in a standard laboratory mill for about 2 minutes to produce metal azo pigment 4.
- Dispersion treatment was performed at a flow rate of 500 g / min under a pressure of 2000 kg / cm 3 . This dispersion process was repeated 10 times to obtain a dispersion.
- the raw materials used for the dispersion are as follows.
- Metal azo pigments 1-4 the above-mentioned metal azo pigments 1-4 PG 36: C.I. I. Pigment Green 36 PG 58: C.I. I. Pigment Green 58 PR254: C.I. I. Pigment Red 254 PR 264: C.I. I. Pigment Red 264 PR 177: C.I. I. Pigment Red 177 PO71: C.I. I. Pigment Orange 71
- Pigment derivative A compound of the following structure (basic pigment derivative)
- Pigment derivative B Compound of the following structure (acid pigment derivative)
- Example 1 The coloring material of Example 1 was manufactured by mixing the following raw materials and toluene.
- the toluene concentration of the coloring composition of Example 1 was 5 ppm.
- the toluene concentration of the coloring composition was measured by performing gas chromatography measurement of the coloring composition after preparing a calibration curve from 0 ppm to 20 ppm by gas chromatography according to a known method.
- Dispersion Y-1 ... 75.0 parts by mass Resin P-1 ... 10.0 parts by mass Polymerizable monomer M-1 ... 2.0 parts by mass Photopolymerization initiator In-1 ... 1 .0 mass part surfactant (following compound, Mw 14000) ... 0.01 mass part
- Polymerization inhibitor p-methoxyphenol
- PMEA propylene glycol monomethyl ether acetate
- Examples 2 to 32, Comparative Examples 1 to 4 In Examples 2 to 32 and Comparative Examples 1 to 4 in the same manner as Example 1, except that the types and amounts of the dispersion, polymerizable monomer, resin, photopolymerization initiator and solvent are changed as described in the following table, respectively. A colored composition was produced. In addition, the toluene concentration described in the following table is the toluene concentration of the coloring composition.
- Example 33 A colored composition of Example 33 was produced in the same manner as Example 1, except that the polymerization inhibitor was changed to 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO).
- TEMPO 2,2,6,6-tetramethylpiperidine 1-oxyl
- Example 34 A colored composition of Example 34 was produced in the same manner as in Example 1 except that the polymerization inhibitor was not blended.
- the raw materials used for the production of the coloring composition are as follows.
- IRGACURE-OXE01 manufactured by BASF, oxime compound
- IRGACURE-OXE02 manufactured by BASF, oxime compound
- In-3 Compound of the following structure (oxime compound)
- IRGACURE-184 manufactured by BASF, ⁇ -hydroxy ketone compound
- ⁇ Evaluation 2> Apply each colored composition within 1 hour after production on a glass substrate with undercoat layer using a spin coater so that the film thickness after prebaking becomes 1.0 ⁇ m, and use a hot plate at 100 ° C for 120 seconds Pre-baking was performed to form a film.
- the film was stored for 300 hours under the conditions of a temperature of 135 ° C. and a humidity of 85% to conduct a high temperature and high humidity test.
- a 1 cm square portion was observed with an optical microscope, and the number of crystalline defects of a size of 0.5 ⁇ m or more was counted and evaluated.
- ⁇ Evaluation 3> Apply each colored composition within 1 hour after production on a glass substrate with undercoat layer using a spin coater so that the film thickness after prebaking becomes 1.0 ⁇ m, and use a hot plate at 100 ° C for 120 seconds Pre-baking was performed to form a film. After holding the obtained film at 150 ° C. for 1 hour, a cycle of holding at ⁇ 15 ° C. for 1 hour was repeated 500 cycles to conduct a temperature cycle test. The transmittance of each of the membranes before and after the temperature cycle test was measured to determine the amount of change in transmittance ( ⁇ T%) before and after the temperature cycle test, and evaluation was made according to the following criteria.
- the amount of change in transmittance ( ⁇ T%) compared is the amount of change in the wavelength with the largest amount of change in transmittance in the wavelength range of 400 to 700 nm (
- the coloring composition of the example was able to produce a film in which the occurrence of defects was suppressed even when the coloring composition was stored for a long time in a low temperature environment (Evaluation 1) ). Further, in the colored compositions of Examples 6 to 17 in which the metal azo pigment in the present invention and the other pigment are used in combination, the high temperature and high humidity environment of the metal azo pigment is higher than the case where no other pigment is used in combination.
- the high temperature and high humidity environment of the metal azo pigment is higher than the case where no other pigment is used in combination.
- Example 6 The coloring composition of Example 6 is coated on a 6 inch (15.24 cm) undercoating silicon substrate using a spin coater so that the film thickness after prebaking becomes 0.5 ⁇ m, and a hot plate at 100 ° C. Pre-baked for 120 seconds to form a colored composition layer.
- An i-line stepper exposure apparatus FPA-3000i5 + (Canon Co., Ltd.) is used for this colored composition layer, and light of a wavelength of 365 nm is irradiated through a 1.2 ⁇ m square Bayer pattern mask, and the exposure dose is obtained. Exposure was performed at 500 mJ / cm 2 .
- the silicon substrate on which the colored composition layer after exposure is formed is placed on the horizontal rotary table of a spin shower developing machine (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developer (CD)
- DW-30 type manufactured by Chemitronics Co., Ltd.
- CD developer
- puddling development was performed at 23 ° C. for 60 seconds using Fuji Film Electronics Materials Co., Ltd., 2000
- rinsing was performed using water to form a pattern, whereby a color filter was manufactured.
- the obtained color filter was incorporated into a solid-state imaging device according to a known method. It was confirmed that this solid-state imaging device has high resolution and excellent color separation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Dispersion Chemistry (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
<1> 下記式(I)で表されるアゾ化合物およびその互変異性構造のアゾ化合物から選ばれる少なくとも1種のアニオンと、2種類以上の金属イオンと、メラミン化合物とを含む金属アゾ顔料と、
エチレン性不飽和結合基を有する化合物と、
溶剤と、を含む着色組成物;
式中、R1およびR2はそれぞれ独立して、OHまたはNR5R6であり、
R3およびR4はそれぞれ独立して、=Oまたは=NR7であり、
R5~R7はそれぞれ独立して、水素原子またはアルキル基である。
<2> 金属アゾ顔料は、上記アニオンと、Zn2+およびCu2+を少なくとも含む金属イオンと、上記メラミン化合物とを含む、<1>に記載の着色組成物。
<3> 金属アゾ顔料中の全金属イオンの1モルを基準として、Zn2+およびCu2+を合計で95~100モル%含有する、<2>に記載の着色組成物。
<4> 金属アゾ顔料中のZn2+とCu2+とのモル比が、Zn2+:Cu2+=199:1~1:15である、<2>または<3>に記載の着色組成物。
<5> 金属アゾ顔料におけるメラミン化合物が、下記式(II)で表される化合物である、<1>~<4>のいずれか1つに記載の着色組成物;
式中R11~R13は、それぞれ独立して水素原子またはアルキル基である。
<6> 更に光重合開始剤を含む、<1>~<5>のいずれか1つに記載の着色組成物。
<7> 光重合開始剤がオキシム化合物である、<6>に記載の着色組成物。
<8> 金属アゾ顔料の100質量部に対して、エチレン性不飽和結合基を有する化合物を10質量部以上含有する、<1>~<7>のいずれかに記載の着色組成物。
<9> 更に、重合禁止剤を含む、<1>~<8>のいずれか1つに記載の着色組成物。
<10> 更に、顔料誘導体を含む、<1>~<9>のいずれか1つに記載の着色組成物。
<11> 顔料誘導体が、塩基性顔料誘導体である、<10>に記載の着色組成物。
<12> 固体撮像素子用である、<1>~<11>のいずれか1つに記載の着色組成物。
<13> <1>~<12>のいずれか1つに記載の着色組成物から得られる膜。
<14> <13>に記載の膜を有するカラーフィルタ。
<15> <13>に記載の膜を有する固体撮像素子。
<16> <13>に記載の膜を有する画像表示装置。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基と共に置換基を有する基を包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光を意味するのみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含まれる。また、露光に用いられる光としては、一般的に、水銀灯の輝線スペクトル、エキシマレーザーに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において「~」を用いて表される数値範囲は、「~」の前後に記載される数値を下限値および上限値として含む範囲を意味する。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の合計量をいう。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アリル」は、アリルおよびメタリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において「工程」との語は、独立した工程を意味するだけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本明細書において、重量平均分子量(Mw)および数平均分子量(Mn)は、ゲルパーミエーションクロマトグラフィ(GPC)により測定したポリスチレン換算値として定義される。
本発明の着色組成物は、
式(I)で表されるアゾ化合物およびその互変異性構造のアゾ化合物から選ばれる少なくとも1種のアニオンと、2種類以上の金属イオンと、メラミン化合物とを含む金属アゾ顔料と、
エチレン性不飽和結合基を有する化合物と、
溶剤と、を含むことを特徴とする。
上記の金属アゾ顔料は、硬度が低い傾向にあり、例えば分散液を調製する際において、金属アゾ顔料の一部が過剰に微細化されると推測され、その結果、着色組成物の保管時に過剰に微細化された金属アゾ顔料が再凝集すると推測される。また、金属アゾ顔料におけるニッケルイオン(Ni2+)の含有量が少ないか、あるいは金属アゾ顔料がニッケルイオンを含まない場合においては、エネルギー的に不安定な状態であると推測され、金属アゾ顔料がより再凝集し易い傾向にある。また、この金属アゾ顔料は、着色組成物の保管時の温度が低い場合において、再凝集が促進されやすい傾向にある。特に、0℃以下の低温環境下においては金属アゾ顔料の再凝集が促進されやすい傾向にある。この理由としては、顔料分散に寄与する成分(例えば分散剤や、表面処理剤等)の運動度が低温により低下して顔料同士の立体反発機能が小さくなり、その結果顔料が再凝集し易くなっていると推測される。着色組成物中にこのような凝集物が生成されると、着色組成物の保管時において、この凝集物が核となって金属アゾ顔料などの着色組成物に含まれる成分の凝集を促進して凝集物のサイズが成長して粗大化すると推測される。このような粗大化した凝集物などを含む着色組成物を用いて膜を製造すると、乾燥時に溶剤が除去されて無くなるため、これらの凝集物が金属アゾ顔料などの結晶化を促進して欠陥が膜に生じると考えられる。本発明の着色組成物は、金属アゾ顔料の他に更にエチレン性不飽和結合基を有する化合物を含むので、エチレン性不飽和結合基を有する化合物が金属アゾ顔料の顔料活性面(特にアゾ部位)と相互作用して、エチレン性不飽和結合基を有する化合物が金属アゾ顔料の表面に吸着され、着色組成物中にて金属アゾ顔料を安定化させることができる。その結果、着色組成物を低温環境下で長期間保管しても、金属アゾ顔料の再凝集などを抑制できると推測される。このため、本発明の着色組成物によれば、低温環境下で長期間保管した場合であっても、欠陥の発生が抑制された膜を製造することが可能となったと推定される。
本発明の着色組成物に含まれる金属アゾ顔料は、2種類以上の金属イオンを含むが、金属イオンの種類により、上述したアニオンと金属イオンとで構成される金属アゾ化合物(金属錯体)の配座が異なる。例えば、Cu2+の場合は平面配座の金属錯体を形成し、Zn2+の場合は正八面体配座の金属錯体を形成する。このため、溶剤などを含む着色組成物中において上述した金属アゾ顔料は、会合し難く不安定な状態で存在していると推測され、着色組成物の保管時に金属アゾ顔料が凝集し易い傾向にあると推測される。しかしながら、オキシム化合物を配合することでオキシム化合物が金属アゾ顔料に対して配位してキレート剤として作用すると推測され、その結果、金属アゾ顔料を安定化させることができ、金属アゾ顔料の凝集などをより効果的に抑制できると推測される。そのため、低温環境下で着色組成物を長期間保管した場合であっても、欠陥がより抑制された膜を製造することができると推測される。
また、本発明の着色組成物にエチレン性不飽和結合基を有する化合物を含有させることで、上述のように保管時に金属アゾ顔料の再凝集などを抑制して、比較的粗大な凝集物の発生を抑制できるものの、ごく微小な凝集物などが生成することがある。このようなごく微小な凝集物は、製膜直後は異物欠陥を生じさせるものではないが、このようなごく微小な凝集物が生成された着色組成物を用いて膜を形成し、得られた膜を高温高湿環境下に曝した場合、膜中に含まれる前述の凝集物が核となって異物欠陥を生じることがある。しかしながら、オキシム化合物をさらに配合することで、上述したように金属アゾ顔料を安定化させることができ、異物発生の原因となりうる微小な凝集物の生成も抑制することができると推測される。このため、着色組成物を用いて得られた膜を高温高湿環境下に曝した場合であっても、異物欠陥の発生を効果的に抑制することができると推測される。
本発明の着色組成物は、下記式(I)で表されるアゾ化合物およびその互変異性構造のアゾ化合物から選ばれる少なくとも1種のアニオンと、2種類以上の金属イオンと、メラミン化合物とを含む金属アゾ顔料を含む。
式中、R1およびR2はそれぞれ独立して、OHまたはNR5R6であり、R3およびR4はそれぞれ独立して、=Oまたは=NR7であり、R5~R7はそれぞれ独立して、水素原子またはアルキル基である。R5~R7が表すアルキル基の炭素数は1~10が好ましく、1~6がより好ましく、1~4が更に好ましい。アルキル基は、直鎖、分岐および環状のいずれであってもよく、直鎖または分岐が好ましく、直鎖がより好ましい。アルキル基は置換基を有していてもよい。置換基としては、後述の置換基Tが挙げられ、ハロゲン原子、ヒドロキシ基、アルコキシ基、シアノ基およびアミノ基が好ましい。
式中R11~R13は、それぞれ独立して水素原子またはアルキル基である。アルキル基の炭素数は1~10が好ましく、1~6がより好ましく、1~4が更に好ましい。アルキル基は、直鎖、分岐および環状のいずれであってもよく、直鎖または分岐が好ましく、直鎖がより好ましい。アルキル基は置換基を有していてもよい。置換基としては、後述の置換基Tが挙げられ、ヒドロキシ基が好ましい。R11~R13の少なくとも一つは水素原子であることが好ましく、R11~R13の全てが水素原子であることがより好ましい。
上述の置換基Tとして、次の基が挙げられる。アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、アミノ基(好ましくは炭素数0~30のアミノ基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロアリールオキシ基、アシル基(好ましくは炭素数1~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、ヘテロアリールオキシカルボニル基、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロアリールチオ基(好ましくは炭素数1~30)、アルキルスルホニル基(好ましくは炭素数1~30)、アリールスルホニル基(好ましくは炭素数6~30)、ヘテロアリールスルホニル基(好ましくは炭素数1~30)、アルキルスルフィニル基(好ましくは炭素数1~30)、アリールスルフィニル基(好ましくは炭素数6~30)、ヘテロアリールスルフィニル基(好ましくは炭素数1~30)、ウレイド基(好ましくは炭素数1~30)、ヒドロキシ基、カルボキシル基、スルホ基、リン酸基、カルボン酸アミド基、スルホン酸アミド基、イミド酸基、メルカプト基、ハロゲン原子、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、ヒドラジノ基、イミノ基、ヘテロアリール基(好ましくは炭素数1~30)。これらの基は、さらに置換可能な基である場合、さらに置換基を有してもよい。さらなる置換基としては、上述した置換基Tで説明した基が挙げられる。
(1-1)上記アニオンとZn2+とで構成される金属アゾ化合物と、メラミン化合物との付加体1aと、上記アニオンとCu2+とで構成される金属アゾ化合物と、メラミン化合物との付加体1bの物理的混合物。
(1-2) (1-1)の物理的混合物において、更に、上記アニオンと、金属イオンMe1とで構成される金属アゾ化合物と、メラミン化合物との付加体1cを含む物理的混合物。
(2-1)上記アニオンとNi2+とで構成される金属アゾ化合物と、メラミン化合物との付加体2aと、上記アニオンとZn2+とで構成される金属アゾ化合物と、メラミン化合物との付加体2bと、上記アニオンと金属イオンMe2とで構成される金属アゾ化合物と、メラミン化合物との付加体2cを含む物理的混合物。
(3-1)上記アニオンとNi2+とで構成される金属アゾ化合物と、メラミン化合物との付加体3aと、上記アニオンとCu2+とで構成される金属アゾ化合物と、メラミン化合物との付加体3bと、上記アニオンと金属イオンMe3とで構成される金属アゾ化合物と、メラミン化合物との付加体3cを含む物理的混合物。
(4-1)上記アニオンとNi2+とで構成される金属アゾ化合物と、メラミン化合物との付加体4aと、上記アニオンと金属イオンMe4aとで構成される金属アゾ化合物と、メラミン化合物との付加体4bの物理的混合物。
(4-2) (4-1)の物理的混合物において、更に、上記アニオンと、金属イオンMe4bとで構成される金属アゾ化合物と、メラミン化合物との付加体4cを含む物理的混合物。
式中、X1およびX2はそれぞれ独立して水素原子またはアルカリ金属イオンであり、X1およびX2の少なくとも一方がアルカリ金属イオンである。R1およびR2はそれぞれ独立して、OHまたはNR5R6である。R3およびR4はそれぞれ独立して、=Oまたは=NR7であり、R5~R7はそれぞれ独立して、水素原子またはアルキル基である。R1~R7については、式(I)のR1~R7と同義であり、好ましい範囲も同様である。X1およびX2が表すアルカリ金属イオンとしては、Na+およびK+が好ましい。
本発明の着色組成物は、上述した金属アゾ顔料以外の着色剤(以下、他の着色剤ともいう)を含有することができる。他の着色剤としては、有彩色着色剤、黒色着色剤などが挙げられる。
有彩色着色剤としては、赤色着色剤、緑色着色剤、青色着色剤、黄色着色剤、紫色着色剤、オレンジ色着色剤などが挙げられる。有彩色着色剤は、顔料であってもよく、染料であってもよい。有彩色着色剤は顔料を含むものであることが好ましい。本発明の着色組成物が上述した金属アゾ顔料の他に、更に異種顔料を含むことで、金属アゾ顔料の高温高湿環境下での異物成長を抑制することができる。
カラーインデックス(C.I.)Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214等(以上、黄色顔料)、
C.I.Pigment Orange 2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73等(以上、オレンジ色顔料)、
C.I.Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,270,272,279等(以上、赤色顔料)、
C.I.Pigment Green 7,10,36,37,58,59等(以上、緑色顔料)、
C.I.Pigment Violet 1,19,23,27,32,37,42等(以上、紫色顔料)、
C.I.Pigment Blue 1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,60,64,66,79,80等(以上、青色顔料)、
これら有機顔料は、単独で若しくは種々組合せて用いることができる。
黒色着色剤としては、カーボンブラック、金属酸窒化物(チタンブラック等)、金属窒化物(チタンナイトライド等)などの無機黒色着色剤や、ビスベンゾフラノン化合物、アゾメチン化合物、ペリレン化合物、アゾ化合物などの有機黒色着色剤が挙げられる。有機黒色着色剤としては、ビスベンゾフラノン化合物、ペリレン化合物が好ましい。ビスベンゾフラノン化合物としては、特表2010-534726号公報、特表2012-515233号公報、特表2012-515234号公報などに記載の化合物が挙げられ、例えば、BASF社製の「Irgaphor Black」として入手可能である。ペリレン化合物としては、C.I.Pigment Black 31、32などが挙げられる。アゾメチン化合物としては、特開平1-170601号公報、特開平2-34664号公報などに記載のものが挙げられ、例えば、大日精化社製の「クロモファインブラックA1103」として入手できる。ビスベンゾフラノン化合物は、下記式で表される化合物およびこれらの混合物であることが好ましい。
式中、R1およびR2はそれぞれ独立して水素原子又は置換基を表し、R3およびR4はそれぞれ独立して置換基を表し、aおよびbはそれぞれ独立して0~4の整数を表し、aが2以上の場合、複数のR3は、同一であってもよく、異なってもよく、複数のR3は結合して環を形成していてもよく、bが2以上の場合、複数のR4は、同一であってもよく、異なってもよく、複数のR4は結合して環を形成していてもよい。
本発明の着色組成物は、エチレン性不飽和結合基を有する化合物を含有する。エチレン性不飽和結合基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。エチレン性不飽和結合基を有する化合物は、モノマーであってもよく、ポリマーなどの樹脂であってもよい。以下、エチレン性不飽和結合基を有するモノマーを重合性モノマーともいう。また、エチレン性不飽和結合基を有するポリマーを重合性ポリマーともいう。
上記式(MO-1)~(MO-6)で表される化合物の各々において、複数のRの内の少なくとも1つは、-OC(=O)CH=CH2、-OC(=O)C(CH3)=CH2、-NHC(=O)CH=CH2または-NHC(=O)C(CH3)=CH2を表す。上記式(MO-1)~(MO-6)で表される化合物の具体例としては、特開2007-269779号公報の段落0248~0251に記載されている化合物が挙げられる。
式(Z-5)中、nは、0~6の整数が好ましく、0~4の整数がより好ましい。また、各nの合計は、3~60の整数が好ましく、3~24の整数がより好ましく、6~12の整数が特に好ましい。
また、式(Z-4)又は式(Z-5)中の-((CH2)yCH2O)-又は-((CH2)yCH(CH3)O)-は、酸素原子側の末端がXに結合する形態が好ましい。
また、重合性モノマーとしては、8UH-1006、8UH-1012(以上、大成ファインケミカル(株)製)、ライトアクリレートPOB-A0(共栄社化学(株)製)などを用いることも好ましい。
また、重合性モノマーとしては、特開2017-48367号公報、特許第6057891号公報、特許第6031807号公報に記載されている化合物を用いることもできる。
式(A-1-1)において、X1は繰り返し単位の主鎖を表し、L1は単結合または2価の連結基を表し、Y1はエチレン性不飽和結合基を表す。
上記式において、RG1およびRG2は、それぞれアルキレン基を表す。RG1およびRG2で表されるアルキレン基としては特に制限されないが、炭素数1~20の直鎖状又は分岐状のアルキレン基が好ましく、炭素数2~16の直鎖状又は分岐状のアルキレン基がより好ましく、炭素数3~12の直鎖状又は分岐状のアルキレン基が更に好ましい。
上記式において、RG3は、水素原子またはメチル基を表す。
上記式において、QG1は、-O-または-NH-を表し、LG1は、単結合または2価の連結基を表す。2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アルキレンオキシ基(好ましくは炭素数1~12のアルキレンオキシ基)、オキシアルキレンカルボニル基(好ましくは炭素数1~12のオキシアルキレンカルボニル基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、OCO-、-S-およびこれらの2以上を組み合わせてなる基が挙げられる。
RG4は、水素原子または置換基を表す。置換基としては、アルキル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルキルチオエーテル基、アリールチオエーテル基、ヘテロアリールチオエーテル基等が挙げられる。
式(A-1-2)において、X2は繰り返し単位の主鎖を表し、L2は単結合または2価の連結基を表し、W1はグラフト鎖を表す。
式(A-1-3)において、X3は繰り返し単位の主鎖を表し、L3は単結合または2価の連結基を表し、A1は酸基を表す。
式(A-1-3)におけるL3が表す2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アルケニレン基(好ましくは炭素数2~12のアルケニレン基)、アルキレンオキシ基(好ましくは炭素数1~12のアルキレンオキシ基)、オキシアルキレンカルボニル基(好ましくは炭素数1~12のオキシアルキレンカルボニル基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、OCO-、-S-およびこれらの2以上を組み合わせてなる基が挙げられる。アルキレン基、アルキレンオキシ基におけるアルキレン基、オキシアルキレンカルボニル基におけるアルキレン基は、直鎖状、分岐状、及び、環状のいずれでもよく、直鎖状または分岐状が好ましい。また、アルキレン基、アルキレンオキシ基におけるアルキレン基、オキシアルキレンカルボニル基におけるアルキレン基は、置換基を有していてもよく、無置換であってもよい。置換基としては、ヒドロキシ基などが挙げられる。
式(A-1-3)におけるA1が表す酸基としては、カルボキシル基、スルホ基、リン酸基が挙げられる。
式(ED2)中、Rは、水素原子または炭素数1~30の有機基を表す。式(ED2)の具体例としては、特開2010-168539号公報の記載を参酌できる。
本発明の着色組成物は、環状エーテル基を有する化合物を含有することができる。環状エーテル基を有する化合物としては、1分子内に環状エーテル基を2個以上有する化合物が好ましく用いられる。環状エーテル基を有する化合物に含まれる環状エーテル基は、100個以下であることが好ましく、10個以下であることがより好ましく、5個以下であることが更に好ましい。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられ、エポキシ基であることが好ましい。すなわち、環状エーテル基を有する化合物は、エポキシ基を有する化合物(以下、エポキシ化合物ともいう)であることが好ましい。
本発明の着色組成物は、エチレン性不飽和結合基を含まない樹脂(以下、他の樹脂ともいう)をさらに含有することができる。他の樹脂は、例えば、顔料などの粒子を組成物中で分散させる用途やバインダーの用途で配合される。なお、主に顔料などの粒子を分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外の目的で樹脂を使用することもできる。
式(X)において、R1は、水素原子またはメチル基を表し、R2は炭素数2~10のアルキレン基を表し、R3は、水素原子またはベンゼン環を含んでもよい炭素数1~20のアルキル基を表す。nは1~15の整数を表す。
また、本発明の着色組成物は、他の樹脂を実質的に含まないこともできる。本発明の着色組成物が他の樹脂を実質的に含まない場合とは、本発明の着色組成物の全固形分中における他の樹脂の含有量が0.1質量%以下であることが好ましく、0.05質量%以下であることがより好ましく、含有しないことが特に好ましい。
また、上述したエチレン性不飽和結合基を有する化合物と他の樹脂との合計の含有量は、本発明の着色組成物の全固形分中5~50質量%であることが好ましい。下限は8質量%以上であることが好ましく、10質量%以上であることがより好ましい。上限は、45質量%以下であることが好ましく、40質量%以下であることがより好ましい。
本発明の着色組成物は、溶剤を含有する。溶剤は有機溶剤が好ましい。溶剤は、各成分の溶解性や着色組成物の塗布性を満足すれば特に制限はない。
本発明の着色組成物は、更に光重合開始剤を含むことが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は光ラジカル重合開始剤であることが好ましい。
また、光重合開始剤の含有量は、上述した金属アゾ顔料の100質量部に対して1~200質量部であることが好ましい。下限は、3質量部以上であることが好ましく、5質量部以上であることが更に好ましい。上限は、100質量部以上であることが好ましく、80質量部以下であることがより好ましい。
また、光重合開始剤としてオキシム化合物を用いた場合、オキシム化合物の含有量は、上述した金属アゾ顔料の100質量部に対して1~200質量部であることが好ましい。下限は、3質量部以上であることが好ましく、5質量部以上であることが更に好ましい。上限は、100質量部以上であることが好ましく、80質量部以下であることがより好ましい。この態様によれば、上述した本発明の効果がより顕著に得られる傾向にある。
本発明の着色組成物は、光重合開始剤を1種のみ含んでいてもよいし、2種以上含んでいてもよい。光重合開始剤を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物は、更に顔料誘導体を含有することが好ましい。この態様によれば、温度変化に対する分光の変動が抑制された膜を形成できる。顔料誘導体としては、顔料の一部が、酸基、塩基性基又はフタルイミド基などで置換された構造を有する化合物が挙げられる。例えば、顔料誘導体としては、酸性顔料誘導体、塩基性顔料誘導体および中性顔料誘導体などが挙げられ、塩基性顔料誘導体が好ましい。
式(syn1)中、Pは色素構造を表し、Lは単結合または連結基を表し、Xは酸基、塩基性基またはフタルイミド基を表し、mは1以上の整数を表し、nは1以上の整数を表し、mが2以上の場合は複数のLおよびXは互いに異なっていてもよく、nが2以上の場合は複数のXは互いに異なってもよい。
アルキレン基の炭素数は、1~30が好ましく、1~15がより好ましく、1~10がさらに好ましい。アルキレン基は、置換基を有していてもよい。アルキレン基は、直鎖、分岐、環状のいずれであってもよい。また、環状のアルキレン基は、単環、多環のいずれであってもよい。
アリーレン基の炭素数は、6~18が好ましく、6~14がより好ましく、6~10がさらに好ましい。
含窒素複素環基は、5員環または6員環が好ましい。また、含窒素複素環基は、単環または縮合環が好ましく、単環または縮合数が2~8の縮合環がより好ましく、単環または縮合数が2~4の縮合環がさらに好ましい。含窒素複素環基に含まれる窒素原子の数は、1~3が好ましく、1~2がより好ましい。含窒素複素環基は、窒素原子以外のヘテロ原子を含んでいてもよい。窒素原子以外のヘテロ原子としては、例えば、酸素原子、硫黄原子が例示される。窒素原子以外のヘテロ原子の数は0~3が好ましく、0~1がより好ましい。含窒素複素環基としては、ピペラジン環基、ピロリジン環基、ピロール環基、ピペリジン環基、ピリジン環基、イミダゾール環基、ピラゾール環基、オキサゾール環基、チアゾール環基、ピラジン環基、モルホリン環基、チアジン環基、インドール環基、イソインドール環基、ベンズイミダゾール環基、プリン環基、キノリン環基、イソキノリン環基、キノキサリン環基、シンノリン環基、カルバゾール環基および下記式(L-1)~(L-7)で表される基が挙げられる。
式中の*は連結手を表す。Rは水素原子または置換基を表す。置換基としては、上述した置換基Tが挙げられる。
式(X-3)~(X-9)中、*は連結手を表し、R100~R106は、各々独立に水素原子、アルキル基、アルケニル基またはアリール基を表し、R100とR101は互いに連結して環を形成していてもよい。
R100~R106が表すアルケニル基の炭素数は、2~10が好ましく、2~8がより好ましく、2~4がさらに好ましい。
R100~R106が表すアリール基の炭素数は、6~18が好ましく、6~14がより好ましく、6~10がさらに好ましい。
R100とR101は互いに連結して環を形成していてもよい。環は、脂環であってもよく、芳香族環であってもよい。環は単環であってもよく、縮合環であってもよい。R100とR101が結合して環を形成する場合の連結基としては、-CO-、-O-、-NH-、2価の脂肪族基およびそれらの組み合わせからなる群より選ばれる2価の連結基が挙げられる。R100とR101は環を形成していないことが好ましい。
R100およびR101は、それぞれ独立して、アルキル基またはアリール基を表すことが好ましく、アルキル基がより好ましい。アルキル基は、直鎖または分岐のアルキル基が好ましく、直鎖のアルキル基がより好ましい。
式(syn1)において、nは1~4が好ましく、1~3がより好ましく、1~2がさらに好ましい。
式中、Rp1は、アルキル基またはアリール基を表し、
Rp2は、単結合、-NR-、-CO-、-CO2-、-SO2-、-O-、-S-またはこれらの組み合わせからなる基を表し、Rは、水素原子、アルキル基またはアリール基を表し、
B1は単結合、または、(t+1)価の連結基を表し、
C1は、単結合、-NR-、-CO-、-CO2-、-SO2-、-O-、-S-またはこれらの組み合わせからなる基を表し、Rは、水素原子、アルキル基またはアリール基を表し、
D1は、単結合、アルキレン基、または、アリーレン基を表し、
E1は、酸基、塩基性基またはフタルイミド基を表す。
tは1~5の整数を表す;
Rp2は、単結合、-NR-、-CO-、-CO2-、-SO2-、-O-、-S-またはこれらの組み合わせからなる基を表し、Rは、水素原子、アルキル基またはアリール基を表す。Rが表すアルキル基は、直鎖、分岐、環状が挙げられ、直鎖または分岐が好ましい。アルキル基の炭素数は1~10が好ましく、1~5がより好ましい。Rが表すアリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。Rは水素原子が好ましい。Rp2は、-NRCO-、-CONR-、-SO2NR-または-NRSO2-が好ましく、-NRCO-または-CONR-がより好ましい。
また、顔料誘導体の含有量は、金属アゾ顔料100質量部に対し、1~30質量部が好ましく、3~20質量部がさらに好ましい。顔料誘導体は、1種のみを用いてもよいし、2種以上を併用してもよい。
本発明の着色組成物は、パターンの硬度を向上させる目的や、硬化温度を下げる目的で、硬化促進剤を含んでもよい。硬化促進剤としては、チオール化合物などが挙げられる。
式(T1)
式(T1)中、nは2~4の整数を表し、Lは2~4価の連結基を表す。
本発明の着色組成物は、界面活性剤を含有することが好ましい。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用でき、塗布性をより向上できるという理由からフッ素系界面活性剤が好ましい。
上記の化合物の重量平均分子量は、好ましくは3,000~50,000であり、例えば、14,000である。
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノブタジエン化合物、メチルジベンゾイル化合物、クマリン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物などを用いることができる。これらの詳細については、特開2012-208374号公報の段落番号0052~0072、特開2013-68814号公報の段落番号0317~0334の記載を参酌でき、これらの内容は本明細書に組み込まれる。紫外線吸収剤の具体例としては、下記構造の化合物などが挙げられる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)などが挙げられる。また、ベンゾトリアゾール化合物としてはミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)を用いてもよい。
本発明の着色組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応および/または縮合反応によってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられる。シランカップリング剤は、ビニル基、エポキシ基、スチレン基、メタクリル基、アミノ基、イソシアヌレート基、ウレイド基、メルカプト基、スルフィド基、および、イソシアネート基から選ばれる少なくとも1種の基と、アルコキシ基とを有するシラン化合物が好ましい。シランカップリング剤の具体例としては、例えば、N-β-アミノエチル-γ-アミノプロピルメチルジメトキシシラン(信越化学工業社製、KBM-602)、N-β-アミノエチル-γ-アミノプロピルトリメトキシシラン(信越化学工業社製、KBM-603)、N-β-アミノエチル-γ-アミノプロピルトリエトキシシラン(信越化学工業社製、KBE-602)、γ-アミノプロピルトリメトキシシラン(信越化学工業社製、KBM-903)、γ-アミノプロピルトリエトキシシラン(信越化学工業社製、KBE-903)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業社製、KBM-503)、3-グリシドキシプロピルトリメトキシシラン(信越化学工業社製、KBM-403)等が挙げられる。シランカップリング剤の詳細については、特開2013-254047号公報の段落番号0155~0158の記載を参酌でき、この内容は本明細書に組み込まれる。
本発明の着色組成物は、重合禁止剤を含有することが好ましい。本発明の着色組成物が重合禁止剤を含有することにより、低温環境下で着色組成物を長期間保管した場合であっても、欠陥がより抑制された膜を製造することができる。
本発明の着色組成物が重合禁止剤を含有する場合、重合禁止剤の含有量は、着色組成物中、0.0001~1質量%が好ましい。下限は、0.0005質量%以上が好ましく、0.001質量%以上がより好ましい。上限は、0.5質量%以下が好ましく、0.1質量%以下がより好ましい。本発明の着色組成物は重合禁止剤を1種類のみを含んでいてもよいし、2種類以上含んでいてもよい。重合禁止剤を2種類以上含む場合はそれらの合計量が上記範囲となることが好ましい。
本発明の着色組成物には、必要に応じて、各種添加剤、例えば、充填剤、密着促進剤、酸化防止剤、潜在酸化防止剤、熱重合開始剤等を配合することができる。これらの添加剤としては、特開2004-295116号公報の段落番号0155~0156に記載の添加剤を挙げることができ、この内容は本明細書に組み込まれる。また、酸化防止剤としては、例えばフェノール化合物、リン系化合物(例えば特開2011-90147号公報の段落番号0042に記載の化合物)、チオエーテル化合物などを用いることができる。市販品としては、例えば(株)ADEKA製のアデカスタブシリーズ(AO-20、AO-30、AO-40、AO-50、AO-50F、AO-60、AO-60G、AO-80、AO-330など)が挙げられる。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開WO2014/021023号公報、国際公開WO2017/030005号公報、特開2017-008219号公報に記載された化合物が挙げられる。市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。熱重合開始剤としては、ピナコール化合物、有機過酸化物、アゾ化合物などが挙げられ、ピナコール化合物が好ましい。ピナコール化合物としては、ベンゾピナコール、1,2-ジメトキシ-1,1,2,2-テトラフェニルエタン、1,2-ジエトキシ-1,1,2,2-テトラフェニルエタン、1,2-ジフェノキシ-1,1,2,2-テトラフェニルエタン、1,2-ジメトキシ-1,1,2,2-テトラ(4-メチルフェニル)エタン、1,2-ジフェノキシ-1,1,2,2-テトラ(4-メトキシフェニル)エタン、1,2-ビス(トリメチルシロキシ)-1,1,2,2-テトラフェニルエタン、1,2-ビス(トリエチルシロキシ)-1,1,2,2-テトラフェニルエタン、1,2-ビス(t-ブチルジメチルシロキシ)-1,1,2,2-テトラフェニルエタン、1-ヒドロキシ-2-トリメチルシロキシ-1,1,2,2-テトラフェニルエタン、1-ヒドロキシ-2-トリエチルシロキシ-1,1,2,2-テトラフェニルエタン、1-ヒドロキシ-2-t-ブチルジメチルシロキシ-1,1,2,2-テトラフェニルエタンなどが挙げられる。また、ピナコール化合物については、特表2014-521772号公報、特表2014-523939号公報、および、特表2014-521772号公報の記載を参酌でき、これらの内容は本明細書に組み込まれる。
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。
例えば、上述した範囲内で異なる孔径のフィルタを組み合わせてもよい。ここでの孔径は、フィルタメーカーの公称値を参照することができる。市販のフィルタとしては、例えば、日本ポール株式会社(DFA4201NIEYなど)、アドバンテック東洋株式会社、日本インテグリス株式会社(旧日本マイクロリス株式会社)または株式会社キッツマイクロフィルタ等が提供する各種フィルタの中から選択することができる。
また、第1のフィルタでのろ過は、分散液のみで行い、他の成分を混合した後で、第2のフィルタでろ過を行ってもよい。第2のフィルタとしては、第1のフィルタと同様の材料等で形成されたものを使用することができる。
本発明の膜は、上述した本発明の着色組成物から得られる膜である。膜の厚さは、目的に応じて適宜調整できる。例えば、膜厚は、20μm以下が好ましく、10μm以下がより好ましく、5μm以下がさらに好ましい。膜厚の下限は、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.3μm以上がさらに好ましい。
着色組成物層を形成する工程では、着色組成物を用いて、支持体上に着色組成物層を形成する。支持体としては、特に限定は無く、用途に応じて適宜選択できる。例えば、ガラス基板、シリコン基板などが挙げられ、シリコン基板であることが好ましい。また、シリコン基板には、電荷結合素子(CCD)、相補型金属酸化膜半導体(CMOS)、透明導電膜などが形成されていてもよい。また、シリコン基板には、各画素を隔離するブラックマトリクスが形成されている場合もある。また、シリコン基板には、上部の層との密着性改良、物質の拡散防止或いは基板表面の平坦化のために下塗り層が設けられていてもよい。
<<露光工程>>
次に、着色組成物層をパターン状に露光する(露光工程)。例えば、着色組成物層に対し、ステッパー露光機やスキャナ露光機などを用いて、所定のマスクパターンを有するマスクを介して露光することで、パターン露光することができる。これにより、露光部分を硬化することができる。
露光に際して用いることができる放射線(光)としては、g線、i線等が挙げられる。また、波長300nm以下の光(好ましくは波長180~300nmの光)を用いることもできる。波長300nm以下の光としては、KrF線(波長248nm)、ArF線(波長193nm)などが挙げられ、KrF線(波長248nm)が好ましい。
照射量(露光量)は、例えば、0.03~2.5J/cm2が好ましく、0.05~1.0J/cm2がより好ましい。露光時における酸素濃度については適宜選択することができ、大気下で行う他に、例えば酸素濃度が19体積%以下の低酸素雰囲気下(例えば、15体積%、5体積%、または、実質的に無酸素)で露光してもよく、酸素濃度が21体積%を超える高酸素雰囲気下(例えば、22体積%、30体積%、または、50体積%)で露光してもよい。また、露光照度は適宜設定することが可能であり、通常1000W/m2~100000W/m2(例えば、5000W/m2、15000W/m2、または、35000W/m2)の範囲から選択することができる。酸素濃度と露光照度は適宜条件を組み合わせてよく、例えば、酸素濃度10体積%で照度10000W/m2、酸素濃度35体積%で照度20000W/m2などとすることができる。
次に、着色組成物層の未露光部を現像除去してパターンを形成する。着色組成物層の未露光部の現像除去は、現像液を用いて行うことができる。これにより、露光工程における未露光部の着色組成物層が現像液に溶出し、光硬化した部分だけが残る。現像液としては、下地の素子や回路などにダメージを起さない、有機アルカリ現像液が望ましい。現像液の温度は、例えば、20~30℃が好ましい。現像時間は、20~180秒が好ましい。また、残渣除去性を向上するため、現像液を60秒ごとに振り切り、さらに新たに現像液を供給する工程を数回繰り返してもよい。
また、膜の水の接触角は適宜好ましい値に設定することができるが、典型的には、50~110°の範囲である。接触角は、例えば接触角計CV-DT・A型(協和界面科学(株)製)を用いて測定できる。
ドライエッチング法でのパターン形成は、着色組成物を支持体上に塗布して形成した着色組成物層を硬化して硬化物層を形成し、次いで、この硬化物層上にパターニングされたレジスト層を形成し、次いで、パターニングされたレジスト層をマスクとして硬化物層に対してエッチングガスを用いてドライエッチングするなどの方法で行うことができる。レジスト層は、硬化物層上にポジ型またはネガ型の感光性組成物を塗布し、これを乾燥させて形成することが好ましい。レジスト層の形成に用いる組成物としては、ポジ型の感光性組成物が好ましい。ポジ型の感光性組成物としては、紫外線(g線、h線、i線)、KrF線、ArF線等を含む遠紫外線、電子線、イオンビームおよびX線等の放射線に感応する感光性組成物が好ましい。上述のポジ型の感光性組成物は、KrF線、ArF線、i線、X線)に感応する感光性組成物が好ましく、微細加工性の観点からKrF線に感応する感光性組成物がより好ましい。ポジ型の感光性組成物としては、特開2009-237173号公報や特開2010-134283号公報に記載のポジ型レジスト組成物が好適に用いられる。
本発明のカラーフィルタは、上述した本発明の膜を有する。本発明におけるカラーフィルタは、CCD(電荷結合素子)やCMOS(相補型金属酸化膜半導体)などの固体撮像素子や画像表示装置などに用いることができる。
本発明の固体撮像素子は、上述した本発明の着色組成物を用いた膜を有する。固体撮像素子の構成としては、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。
本発明の画像表示装置は、上述した本発明の着色組成物を用いた膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。
樹脂の重量平均分子量は、以下の条件に従って、ゲルパーミエーションクロマトグラフィ(GPC)によって測定した。
カラムの種類:TOSOH TSKgel Super HZM-Hと、TOSOH TSKgel Super HZ4000と、TOSOH TSKgel Super HZ2000とを連結したカラム
展開溶媒:テトラヒドロフラン
カラム温度:40℃
流量(サンプル注入量):1.0μL(サンプル濃度0.1質量%)
装置名:東ソー(株)製 HLC-8220GPC
検出器:RI(屈折率)検出器
検量線ベース樹脂:ポリスチレン樹脂
(金属アゾ顔料1の製造)
46.2gのジアゾバルビツール酸および38.4gのバルビツール酸を、85℃の蒸留水の1100g中に添加した。次いで、この溶液に水酸化カリウム水溶液を添加してpHを約5とした後、90分間攪拌してアゾバルビツール酸前駆体を製造した。
次いで、上記の方法に従って製造されたアゾバルビツール酸前駆体に、82℃の蒸留水の1500gを添加した。次いで、10gの30%塩酸を滴下により添加した。次いで、79.4gのメラミンを添加した。次いで、0.282モルの約25%塩化亜鉛溶液と、0.0015モルの約30%塩化銅(II)溶液との混合物を滴下により添加した。次いで、これらを添加した溶液を82℃の温度で3時間保持した後、KOHを添加してpHを約5.5とした。次いで、この溶液の温度を90℃に昇温し、90℃の温度を維持しつつ、100gの蒸留水を添加して希釈した。次いで、この溶液に21gの30%塩酸を滴下により添加した後、90℃の温度で12時間加熱処理した。次いで、加熱処理後の溶液に水酸化カリウム水溶液を添加してpHを約5とした。次いで、この溶液から顔料を吸引フィルタ上で単離し、洗浄し、80℃での真空乾燥キャビネット中で乾燥させた後、標準実験室ミルで約2分間すり潰して金属アゾ顔料1を製造した。
154.1gのジアゾバルビツール酸および128.1gのバルビツール酸を、85℃の蒸留水の3600g中に添加した。次いで、この溶液に水酸化カリウム水溶液を添加してpHを約5とした後、90分間攪拌してアゾバルビツール酸前駆体を製造した。
次いで、上記の方法に従って製造されたアゾバルビツール酸前駆体に、82℃の蒸留水の5000gを添加した。次いで、252.2gのメラミンを添加した。次いで、0.68モルの約30%塩化ニッケル(II)溶液、0.02モルの約30%塩化銅(II)溶液、および0.200モルの約20%塩化ランタン(III)溶液の混合物を滴下により添加した。次いで、これらを添加した溶液を82℃で3時間保持した後、KOHを添加してpHを約5.5とした。次いで、この溶液の温度を90℃に昇温し、90℃の温度を維持しつつ、1000gの蒸留水を添加して希釈した。次いで、この溶液に113gの30%塩酸を滴下により添加した後、90℃の温度で12時間加熱処理した。次いで、加熱処理後の溶液に水酸化カリウム水溶液を添加してpHを約5とした。次いで、この溶液から顔料を吸引フィルタ上で単離し、洗浄し、80℃での真空乾燥キャビネット中で乾燥させた後、標準実験室ミルで約2分間すり潰して金属アゾ顔料2を製造した。
154.1gのジアゾバルビツール酸および128.1gのバルビツール酸を、85℃の蒸留水の3600g中に添加した。次いで、この溶液に水酸化カリウム水溶液を添加してpHを約5とした後、90分間攪拌してアゾバルビツール酸前駆体を製造した。
次いで、上記の方法に従って製造されたアゾバルビツール酸前駆体に、82℃の蒸留水の5000gを添加した。次いで、252.2gのメラミンを添加した。次いで、0.70モルの約30%塩化ニッケル(II)溶液、0.05モルの約30%塩化亜鉛(II)溶液、および0.167モルの約20%塩化ランタン(III)溶液の混合物を滴下により添加した。次いで、これらを添加した溶液を82℃で3時間保持した後、KOHを添加してpHを約5.5とした。次いで、この溶液の温度を90℃に昇温し、90℃の温度を維持しつつ、1000gの蒸留水を添加して希釈した。次いで、この溶液に113gの30%塩酸を滴下により添加した後、90℃の温度で12時間加熱処理した。次いで、加熱処理後の溶液に水酸化カリウム水溶液を添加してpHを約5とした。次いで、この溶液から顔料を吸引フィルタ上で単離し、洗浄し、80℃での真空乾燥キャビネット中で乾燥させた後、標準実験室ミルで約2分間すり潰して金属アゾ顔料3を製造した。
46.2gのジアゾバルビツール酸および38.4gのバルビツール酸を、85℃の蒸留水の1100g中に添加した。次いで、この溶液に水酸化カリウム水溶液を添加してpHを約5とした後、90分間攪拌してアゾバルビツール酸前駆体を製造した。
次いで、上記の方法に従って製造されたアゾバルビツール酸前駆体に、82℃の蒸留水の5000gを添加した。次いで、252.2gのメラミンを添加した。次いで、0.285モルの約25%塩化ニッケル溶液と0.010モルの約10%塩化ガドリニウム(III)溶液との混合物を滴下により添加した。次いで、これらを添加した溶液を82℃で3時間保持した後、KOHを添加してpHを約5.5とした。次いで、この溶液の温度を90℃に昇温し、90℃の温度を維持しつつ、1000gの蒸留水を添加して希釈した。次いで、この溶液に113gの30%塩酸を滴下により添加した後、90℃の温度で12時間加熱処理した。次いで、加熱処理後の溶液に水酸化カリウム水溶液を添加してpHを約5とした。次いで、この溶液から顔料を吸引フィルタ上で単離し、洗浄し、80℃での真空乾燥キャビネット中で乾燥させた後、標準実験室ミルで約2分間すり潰して金属アゾ顔料4を製造した。
以下の原料を混合したのち、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散した後、さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、分散液を得た。
(分散液の処方)
下記表に記載の顔料・・・13.3質量部
下記表に記載の顔料誘導体・・・1.5質量部
下記表に記載の分散剤・・・5.2質量部
プロピレングリコールモノメチルエーテルアセテート(PGMEA)・・・80質量部
金属アゾ顔料1~4:上述した金属アゾ顔料1~4
PG36:C.I.Pigment Green 36
PG58:C.I.Pigment Green 58
PR254:C.I.Pigment Red 254
PR264:C.I.Pigment Red 264
PR177:C.I.Pigment Red 177
PO71:C.I.Pigment Orange 71
分散剤1:下記構造の樹脂(Mw=24,000、主鎖に付記した数値はモル数であり、側鎖に付記した数値は繰り返し単位の数である。)
分散剤2:下記構造の樹脂(Mw=23,000、主鎖に付記した数値はモル数であり、側鎖に付記した数値は繰り返し単位の数である。)
分散剤3:下記構造の樹脂(エチレン性不飽和結合基を有する化合物、Mw=16,000、x=66モル、y=14モル、z=20モル、側鎖に付記した数値は繰り返し単位の数である。C=C当量=2500)
(実施例1)
以下の原料とトルエンとを混合して実施例1の着色組成物を製造した。実施例1の着色組成物のトルエン濃度は5ppmであった。なお、着色組成物のトルエン濃度は、公知の方法に従い、ガスクロマトグラフィーにて0ppmから20ppmまでの検量線を作成のうえ、着色組成物のガスクロマトグラフィー測定を行って測定した。
分散液Y-1・・・75.0質量部
樹脂P-1・・・10.0質量部
重合性モノマーM-1・・・2.0質量部
光重合開始剤In-1・・・1.0質量部
界面活性剤(下記化合物、Mw=14000)・・・0.01質量部
重合禁止剤(p-メトキシフェノール)・・・0.002質量部
溶剤(プロピレングリコールモノメチルエーテルアセテート(PGMEA)・・・12.0質量部
分散液、重合性モノマー、樹脂、光重合開始剤および溶剤の種類および量をそれぞれ下記表に記載に変更した以外は実施例1と同様の方法で実施例2~32、比較例1~4の着色組成物を製造した。なお、下記表に記載のトルエン濃度は、着色組成物のトルエン濃度である。
重合禁止剤を2,2,6,6-テトラメチルピペリジン1-オキシル(TEMPO)に変更した以外は、実施例1と同様の方法で実施例33の着色組成物を製造した。
上述した分散液
M-1:KAYARAD DPHA(日本化薬(株)製、ジペンタエリスリトールヘキサアクリレート、C=C当量=96)
M-2:NKエステルA-TMMT(新中村化学工業(株)製、ペンタエリスリトールテトラアクリレート、C=C当量=88)
M-3:NKエステル A-DPH-12E(新中村化学工業(株)製、C=C当量=182)
M-4:KAYARAD DPCA-20(日本化薬(株)製、C=C当量=134)
M-5:アロニックスM-350(東亞合成(株)製、C=C当量=143)
P-1:下記構造の樹脂(エチレン性不飽和結合基を有する化合物、Mw=11,000、主鎖に付記した数値はモル数である。固形分40質量%のPGMEA溶液。C=C当量=705)
P-2:下記構造の樹脂(Mw=14,000、主鎖に付記した数値はモル数である。固形分40質量%のPGMEA溶液。C=C当量=0)
In-1:IRGACURE-OXE01(BASF社製、オキシム化合物)
In-2:IRGACURE-OXE02(BASF社製、オキシム化合物)
In-3:下記構造の化合物(オキシム化合物)
In-4:IRGACURE-369(BASF社製、α-アミノケトン化合物)
In-5:IRGACURE-184(BASF社製、α-ヒドロキシケトン化合物)
S-1:プロピレングリコールモノメチルエーテルアセテート
S-2:3-メトキシ-N,N-ジメチルプロパンアミド
各着色組成物を-20℃で180日保管した。保管後の着色組成物を下塗り層付ガラス基板上にプリベーク後の膜厚が1.0μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間プリベークを行って膜を形成した。
得られた膜について、1cm四方の部分を光学顕微鏡で観察し、0.5μm以上のサイズの結晶状の欠陥の数をカウントして評価した。
5:欠陥の数が0個
4:欠陥の数が1~3個
3:欠陥の数が4~6個
2:欠陥の数が7~9個
1:欠陥の数が10個以上
製造後1時間以内の各着色組成物を、下塗り層付ガラス基板上にプリベーク後の膜厚が1.0μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間プリベークを行って膜を形成した。この膜を、温度135℃、湿度85%の条件下で300時間保管して高温高湿試験を行った。高温高湿試験後の膜について、1cm四方の部分を光学顕微鏡で観察し、0.5μm以上のサイズの結晶状の欠陥の数をカウントして評価した。
5:欠陥の数が0個
4:欠陥の数が1~4個
3:欠陥の数が5~9個
2:欠陥の数が10~15個
1:欠陥の数が16個以上
製造後1時間以内の各着色組成物を、下塗り層付ガラス基板上にプリベーク後の膜厚が1.0μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間プリベークを行って膜を形成した。
得られた膜を、150℃で1時間保持した後、-15℃で1時間保持するサイクルを500サイクル繰り返して温度サイクル試験を行った。
温度サイクル試験前後の膜のそれぞれについて透過率を測定して温度サイクル試験前後の透過率の変化量(ΔT%)を求め、以下の基準で評価した。
なお、比較した透過率の変化量(ΔT%)は、波長が400~700nmの範囲において、最も透過率の変化量が大きい波長についての変化量(|温度サイクル試験前の透過率(%)-温度サイクル試験後の透過率(%)|)である。
5: ΔT%≦1
4: 1<ΔT%≦2
3: 2<ΔT%≦3
2: 3<ΔT%≦4
1: 4<ΔT%
また、本発明における金属アゾ顔料と、他の顔料とを併用した実施例6~17の着色組成物においては、他の顔料を併用しなかった場合よりも、金属アゾ顔料の高温高湿環境下での異物成長をより抑制することができた。
実施例6の着色組成物を、6インチ(15.24cm)の下塗り層付シリコン基板上にプリベーク後の膜厚が0.5μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間プリベークを行って着色組成物層を形成した。この着色組成物層に対して、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を使用し、1.2μm四方のベイヤーパターンマスクを介して365nmの波長の光を照射し、露光量500mJ/cm2にて露光を行った。次いで、露光後の着色組成物層が形成されているシリコン基板を、スピン・シャワー現像機(DW-30型、(株)ケミトロニクス製)の水平回転テーブル上に載置し、現像液(CD-2000、富士フイルムエレクトロニクスマテリアルズ(株)製)を用いて23℃で60秒間パドル現像を行なったのち、水を用いてリンスを行い、パターンを形成してカラーフィルタを製造した。
得られたカラーフィルタを公知の方法に従い固体撮像素子に組み込んだ。この固体撮像素子は高解像度で色分離性に優れることが確認された。
Claims (16)
- 前記金属アゾ顔料は、前記アニオンと、Zn2+およびCu2+を少なくとも含む金属イオンと、前記メラミン化合物とを含む、請求項1に記載の着色組成物。
- 前記金属アゾ顔料中の全金属イオンの1モルを基準として、Zn2+およびCu2+を合計で95~100モル%含有する、請求項2に記載の着色組成物。
- 前記金属アゾ顔料中のZn2+とCu2+とのモル比が、Zn2+:Cu2+=199:1~1:15である、請求項2または3に記載の着色組成物。
- 更に光重合開始剤を含む、請求項1~5のいずれか1項に記載の着色組成物。
- 前記光重合開始剤がオキシム化合物である、請求項6に記載の着色組成物。
- 前記金属アゾ顔料の100質量部に対して、前記エチレン性不飽和結合基を有する化合物を10質量部以上含有する、請求項1~7のいずれか1項に記載の着色組成物。
- 更に、重合禁止剤を含む、請求項1~8のいずれか1項に記載の着色組成物。
- 更に、顔料誘導体を含む、請求項1~9のいずれか1項に記載の着色組成物。
- 前記顔料誘導体が、塩基性顔料誘導体である、請求項10に記載の着色組成物。
- 固体撮像素子用である、請求項1~11のいずれか1項に着色組成物。
- 請求項1~12のいずれか1項に記載の着色組成物から得られる膜。
- 請求項13に記載の膜を有するカラーフィルタ。
- 請求項13に記載の膜を有する固体撮像素子。
- 請求項13に記載の膜を有する画像表示装置。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019549152A JP7233373B2 (ja) | 2017-10-20 | 2018-09-12 | 着色組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 |
KR1020207007435A KR102339147B1 (ko) | 2017-10-20 | 2018-09-12 | 착색 조성물, 막, 컬러 필터, 고체 촬상 소자 및 화상 표시 장치 |
CN201880064367.6A CN111183189B (zh) | 2017-10-20 | 2018-09-12 | 着色组合物、膜、滤色器、固体摄像元件及图像显示装置 |
US16/812,611 US11746239B2 (en) | 2017-10-20 | 2020-03-09 | Coloring composition, film, color filter, solid-state imaging element, and image display device |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017203734 | 2017-10-20 | ||
JP2017-203734 | 2017-10-20 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/812,611 Continuation US11746239B2 (en) | 2017-10-20 | 2020-03-09 | Coloring composition, film, color filter, solid-state imaging element, and image display device |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2019077913A1 true WO2019077913A1 (ja) | 2019-04-25 |
Family
ID=66173339
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2018/033764 WO2019077913A1 (ja) | 2017-10-20 | 2018-09-12 | 着色組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11746239B2 (ja) |
JP (1) | JP7233373B2 (ja) |
KR (1) | KR102339147B1 (ja) |
CN (1) | CN111183189B (ja) |
TW (1) | TWI800531B (ja) |
WO (1) | WO2019077913A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023210428A1 (ja) * | 2022-04-27 | 2023-11-02 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子及び画像表示装置 |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006016506A (ja) * | 2004-07-02 | 2006-01-19 | Toyo Ink Mfg Co Ltd | アゾバルビツール酸金属錯体顔料およびその製造方法 |
JP2007224176A (ja) * | 2006-02-24 | 2007-09-06 | Toyo Ink Mfg Co Ltd | 金属錯体顔料、およびそれを用いた着色組成物 |
JP2008144004A (ja) * | 2006-12-08 | 2008-06-26 | Fujifilm Corp | インクジェット記録用インク、インクジェット記録方法、および近赤外線読み取り方法。 |
JP2009029952A (ja) * | 2007-07-27 | 2009-02-12 | Fujifilm Corp | 顔料分散組成物、硬化性組成物、並びにカラーフィルタ及びその製造方法 |
JP5213373B2 (ja) * | 2006-07-13 | 2013-06-19 | ランクセス・ドイチュランド・ゲーエムベーハー | 顔料を調製するための方法 |
JP2013205833A (ja) * | 2012-03-29 | 2013-10-07 | Fujifilm Corp | 着色硬化性組成物、カラーフィルタ及びその製造方法、並びに画像表示装置 |
JP2016180100A (ja) * | 2015-03-23 | 2016-10-13 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
JP2016196614A (ja) * | 2015-04-06 | 2016-11-24 | 富士フイルム株式会社 | 着色硬化性樹脂組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 |
JP2017058612A (ja) * | 2015-09-18 | 2017-03-23 | 大日精化工業株式会社 | カラーフィルター用着色剤組成物及び顔料分散剤の製造方法 |
US20170275465A1 (en) * | 2016-03-23 | 2017-09-28 | Lanxess Deutschland Gmbh | Metal azo pigments |
JP2017171912A (ja) * | 2016-03-23 | 2017-09-28 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
JP2017171914A (ja) * | 2016-03-23 | 2017-09-28 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
JP2017171913A (ja) * | 2016-03-23 | 2017-09-28 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5213373U (ja) | 1975-07-17 | 1977-01-29 | ||
JPH08295810A (ja) * | 1995-04-26 | 1996-11-12 | Toyo Ink Mfg Co Ltd | カラーフィルタ用顔料および着色組成物 |
DE19945245A1 (de) * | 1999-09-21 | 2001-03-22 | Bayer Ag | Mono- und Dikaliumsalze von Azoverbindungen |
JP5523919B2 (ja) * | 2009-08-31 | 2014-06-18 | 富士フイルム株式会社 | 着色組成物、着色感光性組成物、カラーフィルタ、固体撮像素子、及び液晶表示素子 |
JP6503156B2 (ja) * | 2014-03-10 | 2019-04-17 | 東洋インキScホールディングス株式会社 | 固体撮像素子用着色組成物及びカラーフィルタ |
JP2016094571A (ja) * | 2014-11-17 | 2016-05-26 | 東亞合成株式会社 | 硬化型組成物 |
KR102109634B1 (ko) | 2015-01-27 | 2020-05-29 | 삼성전기주식회사 | 파워 인덕터 및 그 제조 방법 |
JP6578252B2 (ja) * | 2015-07-01 | 2019-09-18 | 株式会社Dnpファインケミカル | カラーフィルタ用色材分散液、カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、及び表示装置 |
TWI769146B (zh) | 2016-01-08 | 2022-07-01 | 日商富士軟片股份有限公司 | 著色組成物、著色組成物的製造方法、彩色濾光片、圖案形成方法、固體攝像元件及圖像顯示裝置 |
EP3222672A1 (de) | 2016-03-23 | 2017-09-27 | LANXESS Deutschland GmbH | Metallazopigmente |
JP6826828B2 (ja) * | 2016-07-14 | 2021-02-10 | 株式会社Dnpファインケミカル | カラーフィルタ用色材分散液、カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、及び表示装置 |
-
2018
- 2018-09-12 KR KR1020207007435A patent/KR102339147B1/ko active IP Right Grant
- 2018-09-12 CN CN201880064367.6A patent/CN111183189B/zh active Active
- 2018-09-12 JP JP2019549152A patent/JP7233373B2/ja active Active
- 2018-09-12 WO PCT/JP2018/033764 patent/WO2019077913A1/ja active Application Filing
- 2018-09-19 TW TW107133025A patent/TWI800531B/zh active
-
2020
- 2020-03-09 US US16/812,611 patent/US11746239B2/en active Active
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006016506A (ja) * | 2004-07-02 | 2006-01-19 | Toyo Ink Mfg Co Ltd | アゾバルビツール酸金属錯体顔料およびその製造方法 |
JP2007224176A (ja) * | 2006-02-24 | 2007-09-06 | Toyo Ink Mfg Co Ltd | 金属錯体顔料、およびそれを用いた着色組成物 |
JP5213373B2 (ja) * | 2006-07-13 | 2013-06-19 | ランクセス・ドイチュランド・ゲーエムベーハー | 顔料を調製するための方法 |
JP2008144004A (ja) * | 2006-12-08 | 2008-06-26 | Fujifilm Corp | インクジェット記録用インク、インクジェット記録方法、および近赤外線読み取り方法。 |
JP2009029952A (ja) * | 2007-07-27 | 2009-02-12 | Fujifilm Corp | 顔料分散組成物、硬化性組成物、並びにカラーフィルタ及びその製造方法 |
JP2013205833A (ja) * | 2012-03-29 | 2013-10-07 | Fujifilm Corp | 着色硬化性組成物、カラーフィルタ及びその製造方法、並びに画像表示装置 |
JP2016180100A (ja) * | 2015-03-23 | 2016-10-13 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
JP2016196614A (ja) * | 2015-04-06 | 2016-11-24 | 富士フイルム株式会社 | 着色硬化性樹脂組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 |
JP2017058612A (ja) * | 2015-09-18 | 2017-03-23 | 大日精化工業株式会社 | カラーフィルター用着色剤組成物及び顔料分散剤の製造方法 |
US20170275465A1 (en) * | 2016-03-23 | 2017-09-28 | Lanxess Deutschland Gmbh | Metal azo pigments |
JP2017171912A (ja) * | 2016-03-23 | 2017-09-28 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
JP2017171914A (ja) * | 2016-03-23 | 2017-09-28 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
JP2017171913A (ja) * | 2016-03-23 | 2017-09-28 | ランクセス・ドイチュランド・ゲーエムベーハー | 金属アゾ顔料 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023210428A1 (ja) * | 2022-04-27 | 2023-11-02 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子及び画像表示装置 |
Also Published As
Publication number | Publication date |
---|---|
JP7233373B2 (ja) | 2023-03-06 |
TWI800531B (zh) | 2023-05-01 |
KR20200042497A (ko) | 2020-04-23 |
CN111183189B (zh) | 2021-11-09 |
US11746239B2 (en) | 2023-09-05 |
KR102339147B1 (ko) | 2021-12-15 |
JPWO2019077913A1 (ja) | 2020-11-26 |
US20200207990A1 (en) | 2020-07-02 |
TW201917176A (zh) | 2019-05-01 |
CN111183189A (zh) | 2020-05-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6731475B2 (ja) | 感光性組成物、カラーフィルタ、パターン形成方法、固体撮像素子および画像表示装置 | |
WO2017130825A1 (ja) | 組成物、膜、近赤外線カットフィルタ、積層体、パターン形成方法、固体撮像素子、画像表示装置、赤外線センサおよびカラーフィルタ | |
JP6617201B2 (ja) | 着色組成物、カラーフィルタ、パターン形成方法、固体撮像素子、および、画像表示装置 | |
JP6764479B2 (ja) | 着色組成物、カラーフィルタ、パターン形成方法、固体撮像素子、および、画像表示装置 | |
JP7109624B2 (ja) | 組成物、硬化膜、カラーフィルタ、遮光膜、固体撮像装置及び画像表示装置 | |
WO2019044505A1 (ja) | 樹脂組成物、膜、近赤外線カットフィルタ、赤外線透過フィルタ、固体撮像素子、画像表示装置、赤外線センサおよびカメラモジュール | |
JP6892927B2 (ja) | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子及び画像表示装置 | |
JPWO2018173570A1 (ja) | 感光性着色組成物、硬化膜、カラーフィルタ、固体撮像素子および画像表示装置 | |
JP6931717B2 (ja) | 組成物、膜、赤外線透過フィルタ、固体撮像素子および光センサ | |
WO2019058859A1 (ja) | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子及び画像表示装置 | |
JPWO2018173524A1 (ja) | 着色組成物、顔料分散液、顔料分散液の製造方法、硬化膜、カラーフィルタ、固体撮像素子および画像表示装置 | |
WO2017170339A1 (ja) | 組成物、膜、光学フィルタ、積層体、固体撮像素子、画像表示装置および赤外線センサ | |
JP6604928B2 (ja) | 着色組成物、膜および膜の製造方法 | |
JP2017125953A (ja) | 感放射線性組成物、膜、カラーフィルタ、遮光膜および固体撮像素子 | |
WO2019049635A1 (ja) | 近赤外線吸収有機顔料、樹脂組成物、近赤外線吸収有機顔料の製造方法、近赤外線吸収有機顔料の分光調整方法、膜、積層体、近赤外線カットフィルタ、近赤外線透過フィルタ、固体撮像素子、画像表示装置および赤外線センサ | |
JP7016879B2 (ja) | 着色組成物、膜の製造方法、カラーフィルタの製造方法、固体撮像素子の製造方法および画像表示装置の製造方法 | |
US11746239B2 (en) | Coloring composition, film, color filter, solid-state imaging element, and image display device | |
JPWO2019039136A1 (ja) | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 18867649 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 20207007435 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2019549152 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 18867649 Country of ref document: EP Kind code of ref document: A1 |