JP5544725B2

JP5544725B2 - カラーフィルター用着色樹脂組成物、カラーフィルター、有機ｅｌディスプレイおよび液晶表示装置

カラーフィルター用着色樹脂組成物、カラーフィルター、有機ｅｌディスプレイおよび液晶表示装置 Download PDF

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Publication number: JP5544725B2
Authority: JP; Japan
Prior art keywords: group; general formula; carbon atoms; resin composition; color filter
Prior art date: 2008-02-27
Legal status : Active

Application number

JP2009046090A

Other languages

English (en)

Japanese (ja)

Other versions

JP2010204132A (ja

JP2010204132A5 (enrdf_load_stackoverflow

Inventor

迫　　直樹

誠治秋山

孝行庄田

早恵槇野

靖志賀

敏明横尾

美織石田

Current Assignee

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Corp

Priority date

2008-02-27

Filing date

2009-02-27

Publication date

2014-07-09

2009-02-27 Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp

2009-02-27 Priority to JP2009046090A priority Critical patent/JP5544725B2/ja

2010-09-16 Publication of JP2010204132A publication Critical patent/JP2010204132A/ja

2011-10-13 Publication of JP2010204132A5 publication Critical patent/JP2010204132A5/ja

2014-07-09 Application granted granted Critical

2014-07-09 Publication of JP5544725B2 publication Critical patent/JP5544725B2/ja

Status Active legal-status Critical Current

2029-02-27 Anticipated expiration legal-status Critical

Links

239000011342 resin composition Substances 0.000 title claims description 151
239000004973 liquid crystal related substance Substances 0.000 title claims description 50
150000001875 compounds Chemical class 0.000 claims description 230
125000004432 carbon atom Chemical group C* 0.000 claims description 160
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 157
229920005989 resin Polymers 0.000 claims description 125
239000011347 resin Substances 0.000 claims description 125
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
239000000178 monomer Substances 0.000 claims description 111
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 100
125000001424 substituent group Chemical group 0.000 claims description 99
239000002904 solvent Substances 0.000 claims description 73
125000000217 alkyl group Chemical group 0.000 claims description 70
125000003700 epoxy group Chemical group 0.000 claims description 57
239000002253 acid Substances 0.000 claims description 56
239000000463 material Substances 0.000 claims description 56
239000000049 pigment Substances 0.000 claims description 54
125000000547 substituted alkyl group Chemical group 0.000 claims description 47
125000005843 halogen group Chemical group 0.000 claims description 41
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
239000011230 binding agent Substances 0.000 claims description 38
229910052799 carbon Inorganic materials 0.000 claims description 36
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group 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 claims description 33
239000007787 solid Substances 0.000 claims description 32
229920001577 copolymer Polymers 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 27
150000001721 carbon Chemical group 0.000 claims description 25
230000000977 initiatory effect Effects 0.000 claims description 24
238000004040 coloring Methods 0.000 claims description 23
RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
229910052731 fluorine Inorganic materials 0.000 claims description 22
125000001153 fluoro group Chemical group F* 0.000 claims description 22
150000001450 anions Chemical class 0.000 claims description 19
150000001768 cations Chemical group 0.000 claims description 19
150000008065 acid anhydrides Chemical class 0.000 claims description 18
239000003086 colorant Substances 0.000 claims description 18
125000001624 naphthyl group Chemical group 0.000 claims description 17
150000007519 polyprotic acids Polymers 0.000 claims description 17
238000012719 thermal polymerization Methods 0.000 claims description 16
239000004925 Acrylic resin Substances 0.000 claims description 14
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 13
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
238000007259 addition reaction Methods 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 10
229910052759 nickel Inorganic materials 0.000 claims description 10
229910052719 titanium Inorganic materials 0.000 claims description 10
229910052782 aluminium Inorganic materials 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 8
229910052802 copper Inorganic materials 0.000 claims description 8
229910052742 iron Inorganic materials 0.000 claims description 8
229910052749 magnesium Inorganic materials 0.000 claims description 8
KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 8
229910052710 silicon Inorganic materials 0.000 claims description 8
229910052720 vanadium Inorganic materials 0.000 claims description 8
229910052725 zinc Inorganic materials 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
229920000178 Acrylic resin Polymers 0.000 claims description 6
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 5
101100294113 Caenorhabditis elegans nhr-48 gene Proteins 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
239000000975 dye Substances 0.000 description 140
-1 acryl Chemical group 0.000 description 109
239000000203 mixture Substances 0.000 description 91
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
238000000034 method Methods 0.000 description 71
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239000010408 film Substances 0.000 description 56
239000010410 layer Substances 0.000 description 52
239000000758 substrate Substances 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
239000000126 substance Substances 0.000 description 43
230000015572 biosynthetic process Effects 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 42
239000000047 product Substances 0.000 description 40
238000003786 synthesis reaction Methods 0.000 description 37
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 36
239000003822 epoxy resin Substances 0.000 description 34
229920000647 polyepoxide Polymers 0.000 description 34
239000000243 solution Substances 0.000 description 34
238000000576 coating method Methods 0.000 description 31
150000003254 radicals Chemical class 0.000 description 30
230000002829 reductive effect Effects 0.000 description 30
239000011248 coating agent Substances 0.000 description 29
229910052757 nitrogen Inorganic materials 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
230000005284 excitation Effects 0.000 description 27
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 22
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 22
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
230000005281 excited state Effects 0.000 description 20
230000000052 comparative effect Effects 0.000 description 19
150000002148 esters Chemical class 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
238000010898 silica gel chromatography Methods 0.000 description 18
125000002091 cationic group Chemical group 0.000 description 17
238000011161 development Methods 0.000 description 17
230000018109 developmental process Effects 0.000 description 17
238000001035 drying Methods 0.000 description 17
238000006116 polymerization reaction Methods 0.000 description 17
239000006185 dispersion Substances 0.000 description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
239000001301 oxygen Substances 0.000 description 15
229910052760 oxygen Inorganic materials 0.000 description 15
238000003756 stirring Methods 0.000 description 15
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
238000004506 ultrasonic cleaning Methods 0.000 description 14
238000009835 boiling Methods 0.000 description 13
238000001914 filtration Methods 0.000 description 13
238000004519 manufacturing process Methods 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000011159 matrix material Substances 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000010949 copper Substances 0.000 description 11
230000008569 process Effects 0.000 description 11
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 10
238000007334 copolymerization reaction Methods 0.000 description 10
PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 10
238000000151 deposition Methods 0.000 description 10
239000002994 raw material Substances 0.000 description 10
239000010409 thin film Substances 0.000 description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
125000001931 aliphatic group Chemical group 0.000 description 9
125000000129 anionic group Chemical group 0.000 description 9
210000002858 crystal cell Anatomy 0.000 description 9
230000003595 spectral effect Effects 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000002723 alicyclic group Chemical group 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
125000004093 cyano group Chemical group *C#N 0.000 description 8
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 8
230000008021 deposition Effects 0.000 description 8
239000002270 dispersing agent Substances 0.000 description 8
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 8
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
230000001235 sensitizing effect Effects 0.000 description 8
239000010936 titanium Substances 0.000 description 8
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
238000004057 DFT-B3LYP calculation Methods 0.000 description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
239000004593 Epoxy Substances 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 7
229940125904 compound 1 Drugs 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000005227 gel permeation chromatography Methods 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
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150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 7
125000006850 spacer group Chemical group 0.000 description 7
229920001187 thermosetting polymer Polymers 0.000 description 7
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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 6
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
239000004793 Polystyrene Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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 6
125000003118 aryl group Chemical group 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 6
238000001723 curing Methods 0.000 description 6
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
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150000002430 hydrocarbons Chemical class 0.000 description 6
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
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239000004094 surface-active agent Substances 0.000 description 6
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
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238000007740 vapor deposition Methods 0.000 description 6
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 5
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
150000004056 anthraquinones Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
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 5
230000007423 decrease Effects 0.000 description 5
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230000005283 ground state Effects 0.000 description 5
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FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
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238000000206 photolithography Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
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