WO2006123696A1 - 有機エレクトロルミネッセンス用高分子組成物 - Google Patents
有機エレクトロルミネッセンス用高分子組成物 Download PDFInfo
- Publication number
- WO2006123696A1 WO2006123696A1 PCT/JP2006/309823 JP2006309823W WO2006123696A1 WO 2006123696 A1 WO2006123696 A1 WO 2006123696A1 JP 2006309823 W JP2006309823 W JP 2006309823W WO 2006123696 A1 WO2006123696 A1 WO 2006123696A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- polymer
- polymer composition
- acrylate
- organic
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 151
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 238000005401 electroluminescence Methods 0.000 title claims abstract 3
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 40
- 239000000463 material Substances 0.000 claims abstract description 38
- 239000002861 polymer material Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 63
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 25
- 238000004132 cross linking Methods 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 13
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 9
- 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 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 239000004973 liquid crystal related substance Substances 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000547 conjugated polymer Polymers 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical group C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 claims description 2
- 125000005641 methacryl group Chemical group 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000005372 silanol group Chemical group 0.000 claims description 2
- 150000003553 thiiranes Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 152
- 239000010410 layer Substances 0.000 description 76
- 239000000243 solution Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- -1 butyr groups Chemical group 0.000 description 42
- 238000000034 method Methods 0.000 description 35
- 239000010408 film Substances 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- 125000003710 aryl alkyl group Chemical group 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 239000003999 initiator Substances 0.000 description 25
- 239000000126 substance Substances 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000654 additive Substances 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 14
- 125000004104 aryloxy group Chemical group 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 230000000977 initiatory effect Effects 0.000 description 9
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 9
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 125000003368 amide group Chemical group 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000005462 imide group Chemical group 0.000 description 6
- 150000002466 imines Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 229910052786 argon Inorganic materials 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 229920000412 polyarylene Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 125000005368 heteroarylthio group Chemical group 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 150000003613 toluenes Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 229910001512 metal fluoride Inorganic materials 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- DUITVQPHBCWUAY-UHFFFAOYSA-N 1-ethoxyanthracene Chemical compound C1=CC=C2C=C3C(OCC)=CC=CC3=CC2=C1 DUITVQPHBCWUAY-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910000846 In alloy Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 1
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 description 1
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- FTJGECIARDVRJC-UHFFFAOYSA-N 1-(4-methylsulfanylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(SC)C=C1 FTJGECIARDVRJC-UHFFFAOYSA-N 0.000 description 1
- OYNPGVKMHISHLS-UHFFFAOYSA-N 1-benzylphenanthrene-9,10-dione Chemical compound C1=CC=C2C3=CC=CC=C3C(=O)C(=O)C2=C1CC1=CC=CC=C1 OYNPGVKMHISHLS-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- ASUQXIDYMVXFKU-UHFFFAOYSA-N 2,6-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=C(Br)C=C3C2=C1 ASUQXIDYMVXFKU-UHFFFAOYSA-N 0.000 description 1
- BFQFFNWLTHFJOZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=C3OCOC3=CC=2)=N1 BFQFFNWLTHFJOZ-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- MCNPOZMLKGDJGP-QPJJXVBHSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MCNPOZMLKGDJGP-QPJJXVBHSA-N 0.000 description 1
- YSBDKIDOAVDCRB-UHFFFAOYSA-N 2-[2-(furan-2-yl)ethyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(CCC=2OC=CC=2)=N1 YSBDKIDOAVDCRB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- SURWYRGVICLUBJ-UHFFFAOYSA-N 2-ethyl-9,10-dimethoxyanthracene Chemical compound C1=CC=CC2=C(OC)C3=CC(CC)=CC=C3C(OC)=C21 SURWYRGVICLUBJ-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- XMLSSXNKAAVXDY-UHFFFAOYSA-N 3-(diethylamino)-n-(4-hydroxy-9,10-dioxoanthracen-1-yl)propanamide;hydrochloride Chemical compound Cl.O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2NC(=O)CCN(CC)CC XMLSSXNKAAVXDY-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- JWJMBKSFTTXMLL-UHFFFAOYSA-N 9,10-dimethoxyanthracene Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=C(OC)C2=C1 JWJMBKSFTTXMLL-UHFFFAOYSA-N 0.000 description 1
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 1
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 101000823051 Homo sapiens Amyloid-beta precursor protein Proteins 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 229920000292 Polyquinoline Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 101150049278 US20 gene Proteins 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 description 1
- OMFKRKWGCMBJFW-UHFFFAOYSA-N [2-[ethyl(methyl)amino]phenyl]-phenylmethanone Chemical compound CCN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 OMFKRKWGCMBJFW-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KTLFENNEPHBKJD-UHFFFAOYSA-K benzyl(trimethyl)azanium;tribromide Chemical compound [Br-].[Br-].[Br-].C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 KTLFENNEPHBKJD-UHFFFAOYSA-K 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- BRCRFYDCLUTJRQ-UHFFFAOYSA-N chloroboronic acid Chemical compound OB(O)Cl BRCRFYDCLUTJRQ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009500 colour coating Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- WDCVTFGZJOVDFM-UHFFFAOYSA-N decylcarbamodithioic acid Chemical compound CCCCCCCCCCNC(S)=S WDCVTFGZJOVDFM-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DKKXSNXGIOPYGQ-UHFFFAOYSA-N diphenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C1=CC=CC=C1 DKKXSNXGIOPYGQ-UHFFFAOYSA-N 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- ZEOQPNRYUCROGZ-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH+](CCCC)CCCC ZEOQPNRYUCROGZ-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1491—Heterocyclic containing other combinations of heteroatoms
Definitions
- the present invention relates to a polymer composition for organic electoluminescence.
- organic EL device is a general term for devices using organic compounds as a light emitting material or a charge transport material for a light emitting layer.
- the wet coating method of a polymer material solution is superior in productivity to the method of depositing low molecules.
- a low molecular weight compound having a light emitting property and a charge transporting property is mixed with a polymer compound having a crosslinking group, or a high molecular compound having a light emitting property and a charge transporting property.
- a high molecular compound having a crosslinking group or a low molecular compound having a crosslinking group typified by aromatic bisazide is mixed as a crosslinking agent.
- the crosslinking agent having a crosslinking group has an aromatic ring, the light emitting property and charge transporting property inherent to the light emitting material and charge transporting material may adversely affect.
- Patent Document 6 is an organic EL device including a first organic layer and a second organic layer, in which the first organic layer has a polymer having a carrier transporting property or a light emitting property and a functional group.
- An organic EL device comprising: a low molecular cross-linking agent, and the low molecular cross-linking agent cross-linked in the first organic layer is disclosed.
- low-molecular crosslinking agents having 2 to 4 functional groups are used, and there are problems in the curability of the organic layer and the ease of creating a layer structure.
- Patent Document 1 US6107452
- Patent Document 2 US2002 / 106529 (JP 2002-170667)
- Patent Document 3 WO96 / 20253 (Tokuheihei 10-511718)
- Patent Document 4 ⁇ ⁇ 02002/10129 (Special Table 2004-505169)
- Patent Document 5 WO2004 / 100282
- Patent Document 6 US2005 / 0186106A1
- An object of the present invention is to provide a polymer composition for organic EL, which can easily form a layer structure and can provide an organic EL element excellent in element performance such as efficiency. Means for solving the problem
- the present invention relates to a polymer composition for organic electoluminescence, comprising a polymer material as a charge transport material or a light emitter and a crosslinking agent, wherein the crosslinking agent does not contain an aromatic ring.
- a polymer composition for organic electoluminescence comprising a polymer material as a charge transport material or a light emitter and a crosslinking agent, wherein the crosslinking agent does not contain an aromatic ring.
- this invention relates to the organic electoluminescence device produced using the said polymer composition.
- the polymer composition of the present invention can easily form a layer structure and can provide an organic EL device having excellent device performance.
- organic EL devices made using them are preferable for devices such as liquid crystal display knock lights or curved or flat light sources for illumination, segment type display devices, dot matrix flat panel displays, etc. In use wear.
- the polymer composition of the present invention includes a polymer material as a charge transport material or a light emitter (hereinafter also referred to as a polymer charge transport material or a polymer light emitter, respectively), and further has no aromatic ring. ! Includes a cross-linking agent.
- the crosslinking agent refers to a monomer compound having a substituent capable of being polymerized by the action of heat, light, and a thermal polymerization initiator or a photopolymerization initiator.
- a polymerizable substituent refers to a substituent capable of forming a compound by forming a bond between two or more molecules by causing a polymerization reaction. Since the crosslinking agent used in the present invention does not have an aromatic ring, the crosslinking group does not have an aromatic ring.
- cross-linking groups examples include vinyl groups, acetylene groups, butyr groups, acrylic groups, acrylate groups, acrylamide groups, methacryl groups, methacrylate groups, methacrylamide groups, butyl ether groups, vinylamino groups, silanol groups, small groups.
- a group having a member ring for example, a cyclopropyl group, a cyclobutyl group, an epoxy group, an oxetane group, a diketene group, an episulfide group, etc.
- a rataton group for example, a cyclopropyl group, a cyclobutyl group, an epoxy group, an oxetane group, a diketene group, an episulfide group, etc.
- a rataton group for example, a cyclopropyl group, a cyclobutyl group, an epoxy group, an oxetane group, a
- combinations of groups capable of forming an ester bond or an amide bond can also be used.
- an ester group and an amino group or an ester group and a hydroxyl group.
- cross-linking agent among them, a polyfunctional monomer having two or more functions (having two or more cross-linking groups), preferably five or more functions (having five or more cross-linking groups) has excellent curability and is preferably used. It is done.
- a monomer having a (meth) acrylate group as a crosslinking group that is, (meth) acrylate.
- (Meth) acrylate is a general term for acrylate and meta acrylate). More preferably, it is a (meth) acrylate of an aliphatic alcohol.
- Specific examples of the monofunctional monomer having a (meth) acrylate group include 2-ethylhexyl carbitol acrylate and 2-hydroxyethyl acrylate.
- 1,6-hexanediol examples include rudi (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, 3-methylpentanediol di (meth) acrylate.
- polyfunctional monomers having a (meth) acrylate group include trifunctional (meth) acrylates such as trimethylolpropane tri (meth) acrylate and pentaerythritol tri (meth) acrylate; Tetrafunctional (meth) acrylate, such as tall tetra (meth) acrylate, pentafunctional (meth) acrylate, such as dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, Examples thereof include (meth) atalylate having 6 or more functionalities such as trispentaerythritol otata (meth) atalylate.
- trifunctional (meth) acrylates such as trimethylolpropane tri (meth) acrylate and pentaerythritol tri (meth) acrylate
- Tetrafunctional (meth) acrylate such as tall tetra (meth)
- a bifunctional or higher functional group preferably a pentafunctional or higher functional (meth) acrylate, more preferably dipentaerythritol penta or hexa acrylate, or tripentaerythritol octatalate, more preferably dipentaerythritol.
- Xatalylate or tripentaerythritol octatalate is excellent in curability and is preferably used.
- the crosslinking agent is described, for example, on pages 17 to 56 of Photopolymer Handbook (Industry Research Committee, 1989).
- the crosslinking agent is usually usually 1 to 99 parts by weight, preferably 1 to 60 parts by weight, more preferably 5 to 50 parts by weight with respect to 100 parts by weight of the total amount of the polymer charge transport material or polymer light emitter. It is contained in the range of. When the content of the crosslinking agent is in the range of 1 to 60 parts by mass based on the above criteria, the smoothness of the coating film tends to be favorable, which is preferable.
- crosslinking agents can be used alone or in combination of two or more.
- the polymer composition of the present invention may contain a photopolymerization initiator.
- the photopolymerization initiator include an active radical generator that generates an active radical when irradiated with light, and an acid generator that generates an acid.
- active radical generators include acetophenone photopolymerization initiators, benzoin photopolymerization initiators, benzophenone photopolymerization initiators, thixanthone photopolymerization initiators, and triazine photopolymerization initiators.
- the polymer charge transport material or the polymer light emitter itself generates radicals by light and functions as a photopolymerization initiator. In such a case, without adding a photoinitiator May be.
- acetophenone-based photopolymerization initiator examples include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane 1-one, benzyldimethyl ketal, 2-hydroxy-1-2-methyl 1- [4- (2 Hydroxyethoxy) phenol] propane 1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl 2-morpholino 1 1- (4-methylthiophenyl) propane 1-on, 2 benzil 2 dimethylamino- 1- ( 4-morpholinophenol) butane monoone, 2-hydroxy-2-methyl 1- [4 mono (1-methylvinyl) phenol] propanone oligomers.
- benzoin-based photopolymerization initiator examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.
- benzophenone-based photopolymerization initiators include benzophenone, o benzoyl methyl benzoate, 4-phenol penzophenone, 4-benzoyl 4'-methyldiphenylsulfide, 3, 3 ', 4, 4'-tetra (tert-butyl peroxycarbo- E) Benzophenone, 2, 4, 6 Trimethylbenzophenone and the like.
- Examples of the thixanthone photopolymerization initiator include 2 isopropyl thixanthone, 4 isopropyl thixanthone, 2,4 jetyl thioxanthone, 2,4 dichloro thixanthone, 1 chloro-4 propoxy thixanthone, and the like.
- Triazine photopolymerization initiators include, for example, 2, 4 bis (trichloromethyl) 6- (4-methoxyphenyl) 1, 3, 5 triazine, 2, 4 bis (trichloromethyl) 6- (4 —Metoxynaphthyl) 1, 3, 5 Triazine, 2, 4 Bis (trichloromethyl) 6 Pipeol —1, 3, 5 Triazine, 2, 4 Bis (trichloromethyl) —6— (4-Methoxystyryl) — 1, 3, 5 Triazine, 2, 4 Bis (trichloromethyl) 6— [2— (5-Methylfuran-2-yl) etul] 1, 1, 3, 5 Triazine, 2, 4 Bis (trichloromethyl) 6— [2— (Furan-2-yl) ethyl] 1, 3, 5 Triazine, 2, 4 Bis (trichloromethyl) 6— [2— (4 Jetylamino 2-methylphenyl) tulle] — 1 , 3, 5
- an active radical generator for example, 2, 4, 6 trimethylbenzoyl diphenylphosphine Inoxide, 2, 2, 1 bis (o black mouth phenol) 4, 4 ,, 5, 5, -tetraphenyl 1, 2, -biimidazole, 10-butyl-2-chloroataridon, 2-ethylanthraquinone, benzyl 9, 10 Phenanthrene quinone, camphor quinone, methyl methyl glyoxylate, titanocene compound and the like can also be used.
- Commercially available products can be used as the active radical generator.
- Examples of commercially available photopolymerization initiators include the trade name “Irgacure 907” (acetophenone photopolymerization initiator, manufactured by CIBA—GEIGY).
- Examples of the acid generator include 4-hydroxyphenol dimethylsulfo p-toluenesulfonate, 4-hydroxyphenyldimethylsulfohexafluoroantimonate, 4-acetoxyphenyl dimethylsulfo- N-toluenesulfonate, 4-acetoxiphenol 'methyl' benzylsulfo-hexafluoroantimonate, triphene ninores nolefomu p tonorenosenorefonate, trifénolesnorenohexa hexanoleo
- Examples include onium salts such as antimonate, diphenyldodium p-toluenesulfonate and diphenylhexoxafluroantimonate, nitrobenzyl disilates, and benzoin tosylate.
- active radical generators there are compounds that generate an acid simultaneously with active radicals.
- a triazine photopolymerization initiator is also used as an acid generator. .
- photopolymerization initiators may be used alone or in combination of two or more.
- the polymer composition of the present invention may contain a photopolymerization initiation assistant.
- the photopolymerization initiator is a compound used in combination with the photopolymerization initiator to promote the polymerization of the crosslinking agent initiated by the photopolymerization initiator.
- Examples of photopolymerization initiation assistants include amine photopolymerization initiation assistants and alkoxyanthracene photopolymerization initiation assistants.
- Examples of the amine photopolymerization initiation assistant include triethanolamine, methyl jetanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-Dimethylaminoethyl benzoate, 4-dimethylaminobenzoylhexylhexyl, N, N-dimethylbalato Ruidin, 4,4,1bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4, bis (jetylamino) benzophenone, 4,4,1bis (ethylmethylamino) benzophenone and the like.
- alkoxyanthracene photopolymerization initiation assistant examples include 9,10 dimethoxyanthracene, 2 ethyl-9,10 dimethoxyanthracene, 9,10 ethoxyanthracene, 2 ethyl 9,10 ethoxyanthracene, and the like.
- Commercially available photopolymerization initiation assistants can also be used.
- Examples of commercially available photopolymerization initiation assistants include the trade name “EAB-F” (manufactured by Hodogaya Chemical Co., Ltd.). It is done.
- a strong photopolymerization initiator When a strong photopolymerization initiator is used, its content is usually 10 mol or less, preferably 0.01 mol or more and 5 mol or less per mol of the photopolymerization initiator.
- the total amount of the photopolymerization initiator and the photopolymerization initiation assistant is usually 3 parts by mass or more and 30 parts by mass or less, preferably 5 parts by mass or more and 25 parts by mass or less with respect to 100 parts by mass of the total amount of the crosslinking agent.
- the polymer composition of the present invention may further contain a chain transfer agent.
- chain transfer agents include 2,4-diphenyl 4-methyl 1-pentene, n-dodecyl mercaptan, t-dodecyl mercaptan, n-octyl mercaptan, and limonene.
- the content of the strong chain transfer agent is usually 0.5% or more and 5% or less in terms of weight fraction with respect to the total solid content of the composition of the present invention.
- the polymer composition of the present invention may contain a thermal polymerization initiator.
- a thermal polymerization initiator those generally known as radical polymerization initiators can be used.
- radical polymerization initiators can be used.
- benzoylperoxide lauroylperoxide, t-butylperoxypivalate 1, 1, 1, 1 bis (t butylperoxy) cyclohexane and other organic peroxides
- hydrogen peroxide When using a peroxide as a radical polymerization initiator, use a peroxide as a redox initiator with a reducing agent.
- the polymer light-emitting material used in the present invention has a polystyrene-equivalent number average molecular weight of usually 10 3 to 10 8 .
- conjugated polymer compounds are preferred.
- the role polymer compound means a polymer compound in which a delocalized ⁇ electron pair exists along the main chain skeleton of the polymer compound. As this delocalized electron, an unpaired electron or a lone electron pair may participate in resonance instead of a double bond.
- the polymer light emitter used in the present invention may be a homopolymer or a copolymer.
- polyfluorene for example, Japanese Journal of Applied Physics (Jpn. J Appl. Phys.), 30th page, L1941 (1991)
- polyparaphenylene see, for example, Advanced 'Materials (Adv. Mater.) Vol.
- polypyrrole Polyarylene polymers such as polypyridine, polyarine and polythiophene; polyarylene vinylene polymers such as polyparaphenylene-bilene and polychelene-ylene (see, for example, the published specification of W098Z27136); polyphenylene sulfide ; Polypower rubazole and the like can be mentioned [For example, “Advanced Materials Vol.12 1737 -1750 (2000)” and “Organic EL Display Technology Monthly Display December issue P68 ⁇ 73 ”].
- polyarylene polymer light emitters are preferred.
- Examples of the repeating unit contained in the polyarylene polymer light emitter include an arylene group and a divalent heterocyclic group, and those containing 20 to LOO mol% of these repeating units are preferred, and 50 to 99 mol 0 / Those containing 0 are more preferred.
- the number of carbon atoms constituting the ring of the divalent heterocyclic group is usually about 3 to 60, and specific examples thereof include pyridine monozyl group, diazaphenylene group, quinoline diyl group, quinoxaline diyl group, and atalidine diyl.
- Group, bibilidyl group, phenantyl ring group, the following formula (1), A —0—, —S—, —Se—, —NR,, one, —C (R,) (R,) one, or — Si (R,) (R ′) —.
- the polyarylene polymer light-emitting material includes a repeating unit represented by the following formula (1).
- R la , R lb , R le , R 2a , R 2b and R 2c are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkyl group, Arylalkyloxy group, arylalkylthio group, alkyl group, alkyl group, arylalkyl group, arylalkyl group, acyl group, acyloxy group, amide group, acid imide group, imine residue, Substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, cyano group,
- A represents an atom or a group of atoms together with four carbon atoms on the two benzene rings in the formula (1) to complete a 5-membered ring or a 6-membered ring. As shown below, it is not limited to these.
- each RR ⁇ R is independently a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylalkyl group, an aryl alkyl group, an arylalkyloxy group, an arylalkylthio group, an alkenyl group.
- alkyl group, aryl alkenyl group, aryl alkyl group, acyloxy group, substituted amino group Represents a mono group, a substituted silyloxy group, a substituted silylthio group, a substituted silylamino group, a cyano group or a monovalent heterocyclic group.
- R ′ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an aryloxy group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an alkyl group, Group, alkyl group, arylalkyl group, arylalkyl group, acyl group, acyloxy group, amide group, acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted Represents a silylthio group, a substituted silylamino group, a cyano group, a nitro group or a monovalent heterocyclic group.
- R ′ ′ each independently represents a hydrogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an aryloxy group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an alkyl group, An alkynyl group, an arylalkyl group, an arylalkyl group, an acyl group, a substituted silyl group, a substituted silyloxy group, a substituted silylthio group, a substituted silylamino group, or a monovalent heterocyclic group is represented.
- R, R ⁇ R "halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, aryl group, aryl group, alkyl group, aryl group, alkyl group, alkyl group, alkyl group Group, arylalkyl group, arylalkyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, substituted amino group, amide group, acid imide group, acyl group, acyloxy group, and monovalent heterocyclic group Definitions and specific examples are the same as those described above for R lb , R le , R 2a , R 2b and R.
- 1 O, 1 S, 1 Se, 1 NR,, 1, 1 CR'R, 1 or 1 SiR, R, 1 is preferred O, 1 S-, 1 CR'R, 1 More preferred.
- Amide group acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, cyano group, nitro group, monovalent heterocyclic group,
- the lower aryloxy group, heteroarylthio group, alkyloxycarbonyl group, aryloxycarbonyl group, arylalkyloxycarbonyl group, and heteroaryloxycarbonyl group are the same as described above.
- Examples of the repeating unit represented by the above formula (1) include the following structures.
- a hydrogen atom on the benzene ring is a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an aryl alkyl group.
- the polymer light-emitting material used in the present invention may contain, in addition to the arylene group and divalent heterocyclic group, for example, a repeating unit derived from an aromatic amine. In this case, hole injection property and transport property can be imparted to the polymer light emitter.
- the molar ratio of the repeating unit derived from the arylene group, the repeating unit having a divalent heterocyclic group power and the aromatic amine is usually in the range of 99: 1 to 20:80.
- the repeating unit derived from the aromatic amine force is preferably a repeating unit represented by the following formula (2).
- Ar 4 , Ar 5 , Ar 6 and Ar 7 each independently represent an arylene group or a divalent heterocyclic group.
- Ar 9 and Ar 1Q each independently represent an aryl group or a monovalent heterocyclic group.
- o and p each independently represent 0 or 1, and 0 ⁇ o + p ⁇ 2.
- arylene group and divalent heterocyclic group are the same as those described above.
- aryl groups and monovalent heterocyclic groups are the same as those described for R la , R lb , R lc , R 2a , R 2b and R 1 above.
- Specific examples of the repeating unit represented by the formula (2) include the following structures.
- a hydrogen atom on the aromatic ring is a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group.
- repeating unit represented by the above formula (2) the repeating unit represented by the following formula (3) is particularly preferable.
- each of R 7 , R ° and R 9 independently represents a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an aryloxy group, an arylalkyl group, an arylalkyl group.
- X and y each independently represent an integer from 0 to 4.
- z represents an integer of 0-2.
- w represents an integer of 0 to 5.
- the polymer light emitter used in the present invention may be a random, block or graft copolymer, or a polymer having an intermediate structure thereof, for example, a random copolymer having a block property. It may be a unity. Is it a viewpoint of obtaining a polymer light emitter with high quantum yield of light emission? Et al. Are preferably block copolymers or block copolymers or graft copolymers, rather than complete random copolymers. If the main chain is branched and there are 3 or more terminal ends, dendrimers are also included.
- the terminal group of the polymer light-emitting material used in the present invention is stable since the polymerization active group remains as it is! Protected by the base!
- a structure having a conjugated bond continuous with the conjugated structure of the main chain is preferred, for example, a structure in which it is bonded to an aryl group or a heterocyclic group via a carbon-carbon bond.
- substituents described in Chemical formula 10 of JP-A-9-45478 are exemplified.
- the polymer light emitter used in the present invention preferably has a number average molecular weight of about 10 3 to 10 8 in terms of polystyrene, and a number average molecular weight of about 10 4 to 10 6 in terms of polystyrene. Is more preferable.
- a polymer light-emitting material that emits light in a solid state is preferably used.
- Examples of the method for synthesizing the polymer light emitter used in the present invention include, for example, a method of polymerizing a corresponding monomer by a Suzuki coupling reaction, a method of polymerizing by a Grignard reaction, a method of polymerizing by a Ni (0) catalyst, Polymerization with an oxidizing agent such as FeCl, electrochemically acid
- a method of chemical polymerization or a method of decomposing an intermediate polymer having an appropriate leaving group is exemplified.
- the method of polymerizing by Suzuki coupling reaction, the method of polymerizing by Grindard reaction, and the method of polymerizing by Ni (O) catalyst are preferable because the reaction control is easy.
- the monomer before polymerization must be purified after being purified by methods such as distillation, sublimation purification, and recrystallization. It is also preferable to carry out purification treatment after synthesis, such as reprecipitation purification and fractionation by chromatography.
- Examples of the solvent include black mouth form, methylene chloride, dichloroethane, tetrahydrofuran, toluene, xylene, mesitylene, tetralin, decalin, n-butylbenzene and the like. Depending on the structure and molecular weight of the polymer light emitter, these solvents are usually used in the polymer light emitter. 0.1% by weight or more can be dissolved.
- the amount of the solvent is usually about 1000 to 100,000 parts by weight with respect to 100 parts by weight of the polymer light emitter.
- the polymer composition of the present invention may contain a low molecular weight or oligomer, a dendrimer luminescent dye, a charge transport material, and the like, if necessary, in addition to the polymer light emitter.
- Examples of the polymer charge transport material used in the present invention include a polymer hole transport material and a polymer electron transport material.
- polymer hole transport materials include polyvinyl carbazole or derivatives thereof, polysilane or derivatives thereof, polysiloxane derivatives having aromatic amines in the side chain or main chain, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamines.
- Derivatives polyarine or derivatives thereof, polythiophene or derivatives thereof, polypyrrole or derivatives thereof, poly (p-phenolene-lene) or derivatives thereof, or poly (2,5-cha-lenbiylene) or derivatives thereof, etc. Is exemplified
- JP-A-63-70257, JP-A-63-17586, JP-A-2-135359, JP-A-2-135361, JP-A-2- Examples include those described in No. 209988, No. 3-37992 and No. 3-152184.
- Polybour strength rubazole or a derivative thereof can be obtained, for example, by cation polymerization or radical polymerization of bulur monomer strength.
- polysilane or derivatives thereof include compounds described in Chemical 'Review (Chem. Rev.) No. 89, page 1359 (1989), GB 2300196 published specification, and the like.
- the methods described in these can be used, but the Kipping method is particularly preferably used.
- the polysiloxane or derivative thereof has almost a hole transporting property in the siloxane skeleton structure
- those having the structure of the low molecular hole transporting material in the side chain or main chain are preferably used.
- those having a hole transporting aromatic amine in the side chain or main chain Indicated.
- a polymer compound composed of a repeating unit derived from an aromatic amine is particularly preferred.
- the repeating unit from which the aromatic amine is also derived those represented by the above formula (3) are more preferred, and those represented by the above formula (2) are more preferred.
- polymer charge transport materials known polymer electron transport materials can be used, and examples thereof include polyquinoline or a derivative thereof, polyquinoxaline or a derivative thereof, polyfluorene or a derivative thereof.
- the purity of the polymer material affects the device performance such as luminescence properties. Therefore, the monomer before polymerization is distilled, sublimated and purified, recrystallized, column chromatography. It is preferable to polymerize after purification by the method. In addition, after polymerization, acid washing, alkali washing, neutralization, water washing, organic solvent washing, reprecipitation, centrifugation, extraction, column chromatography, dialysis and other conventional separation operations, purification operations, drying operations, and other operations I prefer to handle it.
- the polymer composition of the present invention contains a polymer charge transport material or polymer light emitter and a crosslinking agent.
- the composition of the present invention may further contain a solvent.
- additives such as a charge transport material, a light emitting material, a surfactant, and a stabilizer may be included.
- the ratio of the polymer charge transport material or polymer light emitter in the composition is 20 wt% to 100 wt%, preferably 40 wt% to 100 wt%, based on the total weight of the composition excluding the solvent.
- the proportion of the solvent in the composition is usually lwt% to 99.9wt%, preferably 60wt% to 99.5wt%, more preferably 80wt% to 99.Owt, based on the total weight of the composition.
- Film formation methods for the polymer composition of the present invention include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, and dip coating.
- Application methods such as spray coating, screen printing, flexographic printing, offset printing, and inkjet printing can be used.
- Printing methods such as screen printing, flexographic printing, offset printing, and inkjet printing are preferred because pattern formation and multi-color coating are easy.
- the viscosity of the polymer composition of the present invention varies depending on the printing method. When the ink composition is passed through a discharge device as an ink thread, such as an ink jet printing method, clogging and flight bending at the time of discharge may occur. In order to prevent this, it is preferable that the range is 1 to 20 mPa's at 25 ° C.
- the solvent used in the polymer composition of the present invention is not particularly limited, but a solvent capable of dissolving or uniformly dispersing materials other than the solvent in the composition is preferable.
- the solvent is a chlorine-based solvent such as chloroform, methyl chloride or dichloroethane, an ether-based solvent such as tetrahydrofuran, or toluene.
- Xylene Tetraline
- Carsol n-Hexylbenzene, Cyclohexylbenzene, Monoclonal Benzene, o-Dichloroguchi benzene and other aromatic hydrocarbon solvents, Decalin, Bicyclohexyl and other aliphatic hydrocarbons
- ketone solvents such as acetone, methyl ethyl ketone, and 2-heptanone
- ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate.
- the layer formed using the polymer composition of the present invention can suppress dissolution when the upper layer is wet-coated, for example, by hardening it by the action of heat or light. .
- the upper layer is wet-coated on the upper layer to be wet-coated, it is preferable to cure the polymer composition of the present invention using the upper layer as well.
- the wet coating is not performed on the upper layer to be wet coated, there is no fear of dissolution.
- the upper layer may be a composition containing no cross-linking agent.
- the optimum value of the film thickness of the charge transport layer or the light emitting layer varies depending on the material used, and the drive voltage and the light emission efficiency are appropriate values.
- it is 1 nm to 1 ⁇ m, preferably 2 nm to 5 OOnm, and more preferably 5 ⁇ ! ⁇ 200nm.
- the organic EL device produced using the polymer composition of the present invention has a charge transport layer or a light-emitting layer between electrodes composed of an anode and a cathode, and the charge transport layer or the light-emitting layer has It is formed using the composition of the present invention.
- an electron transport layer usually between the cathode and the light-emitting layer
- hole transport Layer usually between the anode and the light emitting layer
- the charge transport layer is a hole transport layer and there is only one charge transport layer between the anode and the light emitting layer, the layer is transported as a hole injection layer, a hole transport layer, or a hole injection 'transport. You can express it with any name! /.
- the layer in contact with the anode is referred to as a hole injection layer.
- the polymer composition of the present invention is characterized by excellent performance when used as a hole injection layer.
- the hole transport layer has a structure in contact with the positive electrode (when the hole transport layer is a hole injection layer). It is preferable because the device shows excellent performance!
- the substrate on which the organic EL element of the present invention is formed is not particularly limited as long as it forms an electrode and does not change when an organic layer is formed, such as glass, plastic, polymer film, and silicon substrate. Illustrated. In the case of an opaque substrate, the opposite electrode is preferably transparent or semi-transparent.
- the organic EL device produced using the polymer composition of the present invention usually, at least one of the anode and the electrode having a cathode force is transparent or translucent, and the anode side is transparent or translucent.
- the anode material a conductive metal oxide film, a translucent metal thin film, or the like is used. Specifically, indium oxide, zinc oxide, tin oxide, and their composite materials such as indium-tin-oxide (ITO), indium-zinc-oxide, etc. are used. Films such as NESA, gold, platinum, silver, and copper are used, and ITO, indium “zinc” oxide, and tin oxide are preferable.
- Examples of the production method include a vacuum deposition method, a sputtering method, an ion plating method, and a plating method.
- an organic transparent conductive film such as polyaline or a derivative thereof, polythiophene or a derivative thereof may be used as the anode.
- the film thickness of the anode can be appropriately selected in consideration of light transmittance and electrical conductivity.
- 1S for example, 10 nm to 10 ⁇ m, preferably 20 nm to l ⁇ m, Preferably, it is 50 nm to 500 nm.
- a phthalocyanine derivative In order to facilitate charge injection on the anode, a phthalocyanine derivative, a conductive polymer, a layer such as carbon, a metal oxide, a metal fluoride, an organic insulating material, or the like A layer having an average film thickness of 2 nm or less may be provided.
- a material having a low work function is preferable.
- metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, Or an alloy of two or more of them, or an alloy of one or more of them with one or more of gold, silver, platinum, copper, manganese, titanium, conoret, nickel, tungsten, tin, or Graphite or a graphite intercalation compound is used.
- the cathode may have a laminated structure of two or more layers.
- the film thickness of the cathode can be appropriately selected in consideration of electric conductivity and durability, but is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to l ⁇ m, and more preferably. Is between 50 nm and 500 nm.
- a method for producing the cathode As a method for producing the cathode, a vacuum deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression-bonded, or the like is used.
- a cathode made of a conductive polymer, or a layer having an average film thickness of 2 nm or less such as a metal oxide, metal fluoride, or organic insulating material may be provided between the cathode and the organic material layer.
- a protective layer for protecting the organic EL element may be attached. In order to use the organic EL element stably for a long period of time, it is preferable to attach a protective layer and / or protective cover in order to protect the element from the outside.
- a polymer compound, metal oxide, metal fluoride, metal boride and the like can be used.
- a glass plate, a plastic plate having a low water permeability treatment on the surface, or the like can be used, and the cover is bonded to the element substrate with a thermal effect resin or a photocured resin and sealed.
- a thermal effect resin or a photocured resin and sealed are preferably used. If the space is maintained using a spacer, it is easy to prevent the element from being damaged. If an inert gas such as nitrogen or argon is sealed in the space, it is possible to prevent the oxidation of the cathode.
- a desiccant such as barium oxide in the space, it becomes easy to suppress the moisture adsorbed in the manufacturing process from damaging the device. Of these, it is preferable to take one or more measures.
- the organic EL element produced using the polymer composition of the present invention can be used as a planar light source, a segment display device, a dot matrix display device, a backlight of a liquid crystal display device, and the like.
- the planar anode and cathode may be arranged so as to overlap each other.
- a method in which a mask having a pattern-like window is provided on the surface of the planar light-emitting element, an organic material layer of a non-light-emitting portion is formed extremely thick and substantially non-light-emitting There are a method of emitting light and a method of forming either or both of the anode and the cathode in a pattern.
- both the anode and the cathode may be formed in a stripe shape and arranged so as to be orthogonal to each other. Partial color display and multicolor display are possible by separately applying a plurality of types of polymer light emitters having different emission colors or by using a color filter or a light emission conversion filter.
- the dot matrix element can be driven in a nosic manner, or may be driven in combination with a TFT or the like.
- the number average molecular weight in terms of polystyrene was determined by SEC.
- polymer compound 1 The organic layer was divided into two parts, each was added dropwise to 600 mL of methanol, stirred for 1 hour, the deposited precipitate was filtered and dried under reduced pressure for 2 hours.
- the yield of the obtained polymer (hereinafter referred to as polymer compound 1) was 3.26 g.
- n-octylmagnesium bromide (l.OmolZlTHF solution) was added dropwise over 30 minutes. After completion of the dropwise addition, the temperature was raised to 0 ° C., stirred for 1 hour, then warmed to room temperature and stirred for 45 minutes. The reaction was completed by adding 20 ml of 1N hydrochloric acid in an ice bath, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate.
- N-octyl bromide was added dropwise, and after completion of the addition, the mixture was reacted at 50 ° C for 9 hours. After completion of the reaction, the organic layer was extracted with toluene, washed twice with water, and dried over sodium sulfate. Purification by a silica gel column using hexane as a developing solvent gave 5.13 g (yield 74%) of Compound D as a yellow oil.
- this reaction solution was cooled, and then a mixed solution of 25% aqueous ammonia 200 mlZ methanol 900 mlZ ion-exchanged water 900 ml was poured into the solution and stirred for about 1 hour. Next, the produced precipitate was filtered and collected. This precipitate was dried under reduced pressure and then dissolved in toluene. The toluene solution was filtered to remove insoluble matters, and the toluene solution was purified by passing through a column filled with alumina. Next, this toluene solution was washed with a 1N aqueous hydrochloric acid solution, allowed to stand and separated, and then the toluene solution was recovered.
- this toluene solution was washed with about 3% ammonia water, allowed to stand and liquid-separated, and then a toluene solution was recovered.
- this toluene solution was washed with ion exchange water, allowed to stand and separated, and then the toluene solution was recovered.
- this toluene solution was poured into methanol and re-precipitated.
- the produced precipitate was collected and washed with methanol, and then this precipitate was dried under reduced pressure to obtain a polymer 6. Og.
- This polymer is referred to as polymer compound 2.
- the resulting polystyrene reduced weight-average molecular weight of the polymer compound 2, 8. a 2Xl0 5, the number-average molecular weight was 1. 0x1 0 5.
- bromobenzene (0.28 g, 1.78 mmol) was dissolved in 1 mL of toluene, added to the reaction solution, and stirred at 110 ° C. for 2 hours.
- chloro-boronic acid (0.22 g, 1.49 mmol) was added to the reaction solution and stirred at 110 ° C. for 2 hours.
- the organic layer was added dropwise to 200 mL of a methanol Z water (1Z1) mixture and stirred for 1 hour. Filter the precipitate and use methanol and ion-exchanged water Washed and dried under reduced pressure.
- N, N, —bis (4-bromophenol) — N, N, —bis (4-n-butylphenol) 1, 4-phenyldiamine (1,911 g), N, N, bibis (4-bromophenol) phenolamine (0.848 g) and 2,2, bibilidyl (1.687 g) were added together and dissolved in 109 mL of dehydrated tetrahydrofuran that was bubbled with argon. After the temperature of this solution was raised to 60 ° C, bis (1,5-cyclooctagen) nickel (0) ⁇ Ni (COD) ⁇ (2.971 g) was added and stirred.
- reaction solution was cooled to room temperature, dropped into 25% aqueous ammonia 14 mLZ methanol 109 mLZ ion-exchanged water 109 mL mixed solution and stirred for 1 hour, and then the deposited precipitate was filtered, dried under reduced pressure, and dissolved in 120 mL of toluene. It was. After dissolution, 0.48 g of radiolite was added and stirred for 30 minutes, and the insoluble material was filtered off. The obtained filtrate was purified through an alumina power ram. Next, 236 mL of 4% aqueous ammonia was added and stirred for 2 hours, and then the aqueous layer was removed.
- polymer compound 4 The yield of the obtained polymer (hereinafter referred to as polymer compound 4) was 1.54 g.
- Aliquat 336 1.72g, Compound F 6.2171g, Compound G 0.55085g, Compound H 6.2225g, Compound I 0.5487g in a 500ml 4-neck flask did. Add 100 ml of toluene, and then add 7.6 mg of dichlorobis (triphenylphosphine) palladium (II) and 24 ml of aqueous sodium carbonate solution. After stirring for 3 hours under reflux, add 0.40 g of phenylboric acid. Stir overnight. Sodium / N-jetyldithiocarbamate aqueous solution was added, and the mixture was further stirred for 3 hours under reflux.
- Example 1 9 and Comparative Example 1 4 As shown in Table 1, the polymer compound was mixed with lwt% in toluene, and the additives were mixed and dissolved in the types and addition amounts shown in Table 1. Thereafter, the solution was filtered through a 0.2 micron Teflon (registered trademark) filter to prepare a coating solution.
- Teflon registered trademark
- the obtained solution was formed on a glass substrate by spin coating.
- the one without photoinitiator was beta-treated at 300 ° C / 20min beta condition under nitrogen atmosphere.
- UV exposure using a high-pressure mercury lamp with an illuminance of 50 W / cm 2 measured with i-line (365 nm) was performed for 1 minute in a nitrogen atmosphere, and then a beta of 150 ° C / 20 min in a nitrogen atmosphere Beta on condition.
- these substrates were rinsed with toluene, and the film thickness before and after the toluene rinse was measured with a stylus type film thickness meter (Alphastep manufactured by KLA Tencor).
- Trenchrins was carried out by the method of placing toluene on the substrate with the surface tension raised with a spin coater, rotating at 4000 rpm, and shaking off the toluene on the substrate. The results are shown in Table 1.
- Cross-linking agent type of polymer compound photo-initiator type and toluene rinse Toluene rinse Composition Amount added Amount before film thickness After film thickness
- Example 3 Polymerized ⁇ -product 1 Thigh A (25 parts) 1369 (0.5 part) 50 nm 50 nm
- Example 5 Polymer Compound 1 DPHA (25 parts) TAZPP (0.5 part) 50 nm 50 nm
- Example 7 polymer compound 4 awakening A (25 parts) additive-free 40 nm 20 nm
- DPHA Dipentaerythritol hexaatalylate (KAYARAD DPHA manufactured by Nippon Kayaku)
- TPE—A Trispentaerythritol otata acrylate (Guangei Chemical)
- Butanediol ditalylate 1, 4 Butanediol ditalylate (Alfa Aesar)
- HMM Hexamethoxymethylmelamine crosslinker represented by the following formula
- TAZPP Triazine PP; Photoinitiator made by Nippon Siebel Hegner
- Examples 1 to 9 and Comparative Example 4 were formed by spin coating, and as shown in Table 1, those containing no photoinitiator and beta beta condition 300 ° CZ20min in a nitrogen atmosphere, those containing photoinitiators, i ray for 1 minute UV exposure light illuminance was measured by the high-pressure mercury lamp 50WZcm 2 at (365 nm) under a nitrogen atmosphere Thereafter, beta was performed under a nitrogen condition of 150 ° CZ20min in a nitrogen atmosphere (Examples 10-19 and Comparative Example 7).
- a glass substrate with an ITO film with a thickness of 150 nm formed by sputtering is spin-coated using a solution of PEDOT: poly (ethylene dioxythiophene) Z polystyrene sulfonic acid (Starkvitech, Baytron). Then, the film was dried on a hot plate at 200 ° C. for 10 minutes to form a PEDOT layer as a hole injection layer with a thickness of 50 nm (Comparative Examples 5 and 6). Slight haze was observed in the film of the hole injection layer formed from the solution containing a large amount of the crosslinking agent in Example 1. In other hole injection layers, smooth films without haze were obtained.
- PEDOT poly (ethylene dioxythiophene) Z polystyrene sulfonic acid
- the polymer compound was dissolved in 0.5 wt% of toluene, and the additives were mixed and dissolved in the types and addition amounts shown in Table 2. Then 0.2 micron diameter Teflon (registered trademark)
- a film having a thickness of about 70 nm was formed by spin coating using the prepared polymer light emitting coating solution. Further, this was dried at 90 ° C. under reduced pressure for 1 hour, and then a cathode buffer layer was deposited by depositing lithium fluoride at 4 nm, cathode as calcium, 5 nm, and then aluminum by lOOnm to produce an organic EL device. .
- the degree of vacuum in vapor deposition were all 1 ⁇ 9 X 10- 5 Torr.
- the film coated with the polymer solution composition of the example was cured by the action of heat or light, the dissolution of the film after toluene rinsing was suppressed, and the layer was formed by wet coating. A structure can be formed.
- the hole injection layer made from the polymer solution composition of the example was used as compared with the polymer light emitting device using the hole injection layer of the PEDOT layer of the comparative example. The polymer light emitting device showed a marked improvement in efficiency.
- the layer using the cross-linking agent having an aromatic ring in the molecule of Comparative Example 4 was less effective as shown in Table 2, although dissolution of the film after toluene rinsing was suppressed.
- the polymer compound is lwt% in toluene, and the additives are shown in Table 3. Mixed and dissolved in the kind and amount added. Thereafter, the solution was filtered through a 0.2 micron Teflon (registered trademark) filter to prepare a coating solution.
- Teflon registered trademark
- the obtained solution was formed on a glass substrate by spin coating. This was beta-betad under a nitrogen atmosphere at 300 ° C / 20min. Thereafter, these substrates were rinsed with toluene, and the film thickness before and after the toluene rinse was measured with a stylus type film thickness meter (DEKTAK manufactured by Beco). Toluene rinsing was carried out by a method such as using a spin coater to place toluene on a substrate in a raised state with surface tension, rotating at 4000 rpm, and shaking off the toluene on the substrate. The results are shown in Table 3.
- OXT121 Toagosei's cross-linking agent represented by the following formula
- Example 20 A solution of Example 20, Comparative Examples 8 and 9 was formed by spin coating on a glass substrate with a 150 nm thick ITO film formed by sputtering, and 300 ° C / 20 min in a nitrogen atmosphere. Beta of the beta conditions.
- Polymer compound 5 was dissolved in toluene in an amount of lwt%. Thereafter, the solution was filtered through a 0.2 micron Teflon (registered trademark) filter to prepare a coating solution.
- Teflon registered trademark
- a film having a thickness of about 70 nm was formed by spin coating using the prepared polymer light emitting coating solution. Further, this was dried at 90 ° C. under reduced pressure for 1 hour, and then a cathode buffer layer was deposited by depositing lithium fluoride at 4 nm, cathode as calcium, 5 nm, and then aluminum by lOOnm to produce an organic EL device. .
- the degree of vacuum in vapor deposition were all 1 ⁇ 9 X 10- 5 Torr.
- the film coated with the polymer solution composition of the example was cured by the action of heat or light, the dissolution of the film after toluene rinsing was suppressed, and the layer was formed by wet coating. A structure can be formed.
- the polymer solution composition of the example compared to the polymer light emitting device using the hole injection layer of the comparative example, used a hole injection layer made from the polymer injection composition. The molecular light emitting device showed a marked improvement in efficiency.
- the layer using the crosslinking agent having an aromatic ring in the molecule of Comparative Example 9 was less effective as shown in Table 4, although dissolution of the film after toluene rinsing was suppressed. .
- the polymer composition of the present invention can easily form a layer structure, and has an excellent element performance.
- An element can be provided.
- organic EL devices made using them are preferable for devices such as liquid crystal display knock lights or curved or flat light sources for illumination, segment type display devices, dot matrix flat panel displays, etc. Can be used.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/912,681 US8268193B2 (en) | 2005-05-17 | 2006-05-17 | Polymer composition for organic electroluminescence |
EP06746526A EP1885009A4 (en) | 2005-05-17 | 2006-05-17 | POLYMER COMPOSITION FOR ORGANIC ELECTROLUMINESCENCE |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005-143820 | 2005-05-17 | ||
JP2005143820 | 2005-05-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006123696A1 true WO2006123696A1 (ja) | 2006-11-23 |
Family
ID=37431269
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2006/309823 WO2006123696A1 (ja) | 2005-05-17 | 2006-05-17 | 有機エレクトロルミネッセンス用高分子組成物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8268193B2 (ja) |
EP (1) | EP1885009A4 (ja) |
KR (1) | KR20080007611A (ja) |
CN (1) | CN100559629C (ja) |
TW (1) | TW200700483A (ja) |
WO (1) | WO2006123696A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008149829A1 (ja) * | 2007-05-30 | 2008-12-11 | Sumitomo Chemical Company, Limited | 有機エレクトロルミネッセンス素子および該素子を用いた表示装置 |
WO2009069820A1 (ja) * | 2007-11-29 | 2009-06-04 | Sumitomo Chemical Company, Limited | 有機エレクトロルミネッセンス素子及びその製造方法 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100165604A1 (en) * | 2005-11-30 | 2010-07-01 | Sumitomo Chemical Company, Limited | White organic electroluminescent device |
EP2112702B2 (en) * | 2007-02-15 | 2017-12-13 | Mitsubishi Chemical Corporation | Method for manufacturing an organic electroluminescence device |
JP5293120B2 (ja) | 2008-11-28 | 2013-09-18 | 住友化学株式会社 | 有機エレクトロルミネッセンス素子およびその製造方法 |
JP2013543655A (ja) * | 2010-09-30 | 2013-12-05 | ▲海▼洋王照明科技股▲ふん▼有限公司 | 有機電界発光素子及びその製造方法 |
TWI480309B (zh) * | 2011-12-06 | 2015-04-11 | Nat Univ Tsing Hua | 具有電洞阻擋功能的高分子與接枝有電子注入/傳遞功能的金屬離子鑲嵌入冠醚側鏈之共軛高分子之複合材料及其於oled及有機太陽能電池的用途 |
CN105742517B (zh) * | 2013-01-16 | 2017-07-14 | 张哲夫 | 一种有机电致发光器件 |
JP6913079B2 (ja) * | 2016-03-29 | 2021-08-04 | 住友化学株式会社 | 発光素子 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997007167A1 (fr) * | 1995-08-11 | 1997-02-27 | Nitto Chemical Industry Co., Ltd. | Composition conductrice reticulable, conducteur et procede de fabrication |
JP2003073666A (ja) * | 2001-06-21 | 2003-03-12 | Showa Denko Kk | 有機発光素子および発光材料 |
JP2005243300A (ja) * | 2004-02-24 | 2005-09-08 | Sanyo Electric Co Ltd | 有機エレクトロルミネッセント素子及びその製造方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0300376B1 (en) | 1987-07-20 | 1993-02-03 | E.I. Du Pont De Nemours And Company | Element having improved antistatic layer |
CA2107808C (en) * | 1992-10-07 | 2002-07-23 | Toshiya Sugimoto | Electrically conductive composition |
EP1801181B1 (en) | 1994-12-28 | 2011-12-28 | Cambridge Display Technology Limited | Polymers for use in optical devices |
US5962148A (en) * | 1995-01-11 | 1999-10-05 | Sekisui Chemical Co., Ltd. | Electrically conductive paint composition |
US6024895A (en) | 1995-08-11 | 2000-02-15 | Mitsubishi Rayon Co., Ltd. | Cross-linkable, electrically conductive composition, electric conductor and process for forming the same |
EP0989443A3 (en) * | 1998-09-22 | 2004-03-31 | Fuji Photo Film Co., Ltd. | Anti-reflection film and process for the preparation of the same |
US6107452A (en) | 1998-10-09 | 2000-08-22 | International Business Machines Corporation | Thermally and/or photochemically crosslinked electroactive polymers in the manufacture of opto-electronic devices |
US6372154B1 (en) | 1999-12-30 | 2002-04-16 | Canon Kabushiki Kaisha | Luminescent ink for printing of organic luminescent devices |
DE10037391A1 (de) | 2000-08-01 | 2002-02-14 | Covion Organic Semiconductors | Strukturierbare Materialien, Verfahren zu deren Herstellung und deren Verwendung |
DE10044840A1 (de) * | 2000-09-11 | 2002-04-04 | Siemens Ag | Photostrukturierbare neue organische Halbleitermaterialien |
JP2002170667A (ja) | 2000-11-30 | 2002-06-14 | Hitachi Ltd | 有機エレクトロルミネッセンス素子、その製造方法及び画像表示装置 |
US6597012B2 (en) * | 2001-05-02 | 2003-07-22 | Junji Kido | Organic electroluminescent device |
US8530269B2 (en) | 2003-05-12 | 2013-09-10 | Cambridge Enterprise Ltd | Manufacture of a polymer device |
GB0321781D0 (en) * | 2003-09-17 | 2003-10-15 | Toppan Printing Company Ltd | Electroluminescent device |
US7439537B2 (en) * | 2004-07-30 | 2008-10-21 | Agfa Graphics, N.V. | Divinylfluorenes |
TW200619300A (en) * | 2004-08-31 | 2006-06-16 | Sumitomo Chemical Co | Luminescent-polymer composition and luminescent -polymer device |
-
2006
- 2006-05-17 TW TW095117432A patent/TW200700483A/zh unknown
- 2006-05-17 WO PCT/JP2006/309823 patent/WO2006123696A1/ja active Application Filing
- 2006-05-17 EP EP06746526A patent/EP1885009A4/en not_active Withdrawn
- 2006-05-17 CN CNB2006800166570A patent/CN100559629C/zh not_active Expired - Fee Related
- 2006-05-17 KR KR1020077026677A patent/KR20080007611A/ko not_active Application Discontinuation
- 2006-05-17 US US11/912,681 patent/US8268193B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997007167A1 (fr) * | 1995-08-11 | 1997-02-27 | Nitto Chemical Industry Co., Ltd. | Composition conductrice reticulable, conducteur et procede de fabrication |
JP2003073666A (ja) * | 2001-06-21 | 2003-03-12 | Showa Denko Kk | 有機発光素子および発光材料 |
JP2005243300A (ja) * | 2004-02-24 | 2005-09-08 | Sanyo Electric Co Ltd | 有機エレクトロルミネッセント素子及びその製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1885009A4 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008149829A1 (ja) * | 2007-05-30 | 2008-12-11 | Sumitomo Chemical Company, Limited | 有機エレクトロルミネッセンス素子および該素子を用いた表示装置 |
JP2009010343A (ja) * | 2007-05-30 | 2009-01-15 | Sumitomo Chemical Co Ltd | 有機エレクトロルミネッセンス素子および該素子を用いた表示装置 |
WO2009069820A1 (ja) * | 2007-11-29 | 2009-06-04 | Sumitomo Chemical Company, Limited | 有機エレクトロルミネッセンス素子及びその製造方法 |
JP2009152564A (ja) * | 2007-11-29 | 2009-07-09 | Sumitomo Chemical Co Ltd | 有機エレクトロルミネッセンス素子及びその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20090302278A1 (en) | 2009-12-10 |
CN100559629C (zh) | 2009-11-11 |
KR20080007611A (ko) | 2008-01-22 |
US8268193B2 (en) | 2012-09-18 |
CN101176219A (zh) | 2008-05-07 |
EP1885009A4 (en) | 2009-12-30 |
TW200700483A (en) | 2007-01-01 |
EP1885009A1 (en) | 2008-02-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2006123696A1 (ja) | 有機エレクトロルミネッセンス用高分子組成物 | |
Jin et al. | Synthesis and electroluminescence properties of poly (9, 9-di-n-octylfluorenyl-2, 7-vinylene) derivatives for light-emitting display | |
US8632892B2 (en) | Organic electronic material, organic electronic device, and organic electroluminescent device | |
JP2008525578A (ja) | 有機エレクトロルミネセンスデバイス用の正孔輸送層 | |
WO2008032843A1 (fr) | Dispositif électroluminescent organique | |
JP5555977B2 (ja) | 有機エレクトロニクス用材料、並びにこれを用いた有機エレクトロニクス素子及び有機エレクトロルミネセンス素子 | |
JP2007180020A (ja) | 白色有機エレクトロルミネッセンス素子 | |
WO2006132355A1 (ja) | 芳香族グラフト重合体 | |
JP5134210B2 (ja) | 有機エレクトロルミネッセンス用高分子組成物 | |
JP3939533B2 (ja) | フルオレンが導入された電界発光高分子及びそれを用いた電界発光素子 | |
TW511394B (en) | Polymeric fluorescent substance and polymer light emitting device | |
US20100165604A1 (en) | White organic electroluminescent device | |
WO2007063897A1 (ja) | 白色有機エレクトロルミネッセンス素子 | |
JP5352968B2 (ja) | 高分子化合物および高分子発光素子 | |
WO2007142252A1 (ja) | 高分子化合物および高分子発光素子 | |
Peng et al. | An Efficient Blue‐Emitting Conjugated Copolymer Based on Fluorene and Carbazole with a Peripheral Dendritic Carbazole Pendant at the 9‐Position | |
WO2006129860A1 (ja) | 高分子組成物および高分子発光素子 | |
JP2009001777A (ja) | 高分子化合物及びその製造方法、並びに、その高分子化合物を用いた発光材料、液状組成物、薄膜、高分子発光素子、面状光源、表示装置、有機トランジスタ及び太陽電池 | |
JP4333786B2 (ja) | 有機エレクトロルミネッセンス素子 | |
JP2007224282A (ja) | 高分子化合物およびそれを用いた高分子発光素子 | |
WO2007043439A1 (ja) | 高分子化合物とそれを用いた高分子発光素子 | |
Zhang et al. | Synthesis, characterization, and electro‐optical properties of a soluble conjugated polymer containing an oxadiazole unit in the main chain | |
JP4162025B2 (ja) | 有機エレクトロルミネッセンス素子 | |
JP2008244462A (ja) | 有機エレクトロニクス用材料、並びにこれを用いた有機エレクトロニクス素子及び有機エレクトロルミネセンス素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200680016657.0 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 11912681 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020077026677 Country of ref document: KR |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006746526 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: RU |
|
WWP | Wipo information: published in national office |
Ref document number: 2006746526 Country of ref document: EP |