JP7491311B2 - 電荷輸送性ワニス - Google Patents
電荷輸送性ワニス Download PDFInfo
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- JP7491311B2 JP7491311B2 JP2021527666A JP2021527666A JP7491311B2 JP 7491311 B2 JP7491311 B2 JP 7491311B2 JP 2021527666 A JP2021527666 A JP 2021527666A JP 2021527666 A JP2021527666 A JP 2021527666A JP 7491311 B2 JP7491311 B2 JP 7491311B2
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- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910020881 PMo12O40 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NAJAZZSIKSSBGH-UHFFFAOYSA-N butane-1,1,1,2-tetracarboxylic acid Chemical compound CCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O NAJAZZSIKSSBGH-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000001186 cumulative effect Effects 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
- QTRRAHGRSMFAKW-UHFFFAOYSA-N iridium(3+);1-phenylpyrazole Chemical compound [Ir+3].C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1 QTRRAHGRSMFAKW-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000000611 organothio group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- GBSZYMVOJYAZPH-UHFFFAOYSA-N thieno[2,3-e][1]benzothiole Chemical class S1C=CC2=C1C=CC1=C2SC=C1 GBSZYMVOJYAZPH-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Description
1.(A)表面処理剤で表面修飾されたジルコニア粒子、(B)単分散の電荷輸送性有機化合物及び(C)有機溶媒を含む電荷輸送性ワニス。
2.前記表面処理剤で表面修飾されたジルコニア粒子の平均粒子径が、2~100nmである1の電荷輸送性ワニス。
3.前記電荷輸送性有機化合物が、アリールアミン誘導体、チオフェン誘導体及びピロール誘導体から選ばれる少なくとも1種を含む1又は2の電荷輸送性ワニス。
4.前記電荷輸送性有機化合物が、アリールアミン誘導体を含む3の電荷輸送性ワニス。
5.前記電荷輸送性有機化合物の分子量が、200~9,000である1~4のいずれかの電荷輸送性ワニス。
6.前記電荷輸送性有機化合物が、前記有機溶媒に溶解している1~5のいずれかの電荷輸送性ワニス。
7.更に、(D)ドーパントを含む1~6のいずれかの電荷輸送性ワニス。
8.(D)ドーパントが、アリールスルホン酸エステル化合物である7の電荷輸送性ワニス。
9.1~8のいずれかの電荷輸送性ワニスから得られる電荷輸送性薄膜。
10.9の電荷輸送性薄膜を備える有機EL素子。
11.前記電荷輸送性薄膜が、正孔注入層又は正孔輸送層である10の有機EL素子。
本発明の電荷輸送性ワニスは、(A)表面処理剤で表面修飾されたジルコニア粒子(以下、表面修飾ジルコニア粒子ともいう。)、(B)単分散の電荷輸送性有機化合物、及び(C)有機溶媒を含むものである。
(A)成分の表面修飾ジルコニア(ZrO2)粒子は、ジルコニアからなる核粒子を表面処理剤で表面処理して得られるものである。前記表面処理剤としては、n-プロピルトリメトキシシラン、n-プロピルトリエトキシシラン、n-オクチルトリメトキシシラン、n-オクチルトリエトキシシラン、フェニルトリメトキシシラン、2-[メトキシ(ポリエチレンオキシ)プロピル]-トリメトキシシラン、メトキシトリ(エチレンオキシ)プロピルトリメトキシシラン、3-アミノプロピルトリメトキシシラン、3-メルカプトプロピルトリメトキシシラン、3-(メタクリロイルオキシ)プロピルトリメトキシシラン、3-イソシアナトプロピルトリエトキシシラン、3-イソシアナトプロピルトリメトキシシラン、グリシドキシプロピルトリメトキシシラン等のシランカップリング剤;ヘプタノール、ヘキサノール、オクタノール、ベンジルアルコール、フェノール、エタノール、プロパノール、ブタノール、オレイルアルコール、ドデシルアルコール、オクタデカノール等のアルコール;トリエチレングリコールモノメチルエーテル等のグリコールエーテル;オクタン酸、酢酸、プロピオン酸、2-[2-(2-メトキシエトキシ)エトキシ]酢酸、オレイン酸、ステアリン酸、安息香酸等のカルボン酸等が挙げられる。
前記有機溶媒としては、前述した各成分や後述する各任意成分を溶解又は分散可能なものであれば、特に限定されないが、プロセス適合性に優れている点で低極性溶媒を用いることが好ましい。本発明において、低極性溶媒とは周波数100kHzでの比誘電率が7未満のものを、高極性溶媒とは周波数100kHzでの比誘電率が7以上のものと定義する。
本発明の電荷輸送性ワニスは、本発明の電荷輸送性ワニスから得られる薄膜の電荷輸送性を向上させる等の目的で、ドーパントを含んでもよい。ドーパントとしては、ワニスに使用する少なくとも一種の溶媒に溶解するものであれば特に限定されず、無機系のドーパント、有機系のドーパントのいずれも使用できる。更に、ドーパントは、ワニスから固体膜である電荷輸送性薄膜を得る過程で、例えば、焼成時の加熱といった外部からの刺激によって、分子内の一部が外れることによってドーパントとしての機能が初めて発現又は向上するようになる物質、例えば、スルホン酸基が脱離しやすい基で保護されたアリールスルホン酸エステル化合物であってもよい。
本発明の電荷輸送性ワニスは、得られる電荷輸送性薄膜の膜物性の調整等の目的で、更に有機シラン化合物を含んでもよい。前記有機シラン化合物としては、ジアルコキシシラン化合物、トリアルコキシシラン化合物又はテトラアルコキシシラン化合物が挙げられる。とりわけ、有機シラン化合物としては、ジアルコキシシラン化合物又はトリアルコキシシラン化合物が好ましく、トリアルコキシシラン化合物がより好ましい。有機シラン化合物は、1種単独で又は2種以上を組み合わせて用いてもよい。
本発明の電荷輸送性薄膜は、本発明の電荷輸送性ワニスを基材上に塗布し、焼成することで形成することができる。
本発明の有機EL素子は、一対の電極を有し、これら電極の間に、本発明の電荷輸送性薄膜からなる機能層を有するものである。
(a)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(b)陽極/正孔注入層/正孔輸送層/発光層/電子注入輸送層/陰極
(c)陽極/正孔注入輸送層/発光層/電子輸送層/電子注入層/陰極
(d)陽極/正孔注入輸送層/発光層/電子注入輸送層/陰極
(e)陽極/正孔注入層/正孔輸送層/発光層/陰極
(f)陽極/正孔注入輸送層/発光層/陰極
(1)MALDI-TOF-MS:ブルカー社製autoflex III smartbeam
(2)1H-NMR:日本電子(株)製JNM-ECP300 FT NMR SYSTEM
(3)基板洗浄:長州産業(株)製基板洗浄装置(減圧プラズマ方式)
(4)ワニスの塗布:ミカサ(株)製スピンコーターMS-A100
(5)膜厚測定及び表面形状測定:(株)小坂研究所製微細形状測定機サーフコーダET-4000A
(6)素子の作製:長州産業(株)製多機能蒸着装置システムC-E2L1G1-N
(7)素子の電流密度の測定:(株)イーエッチシー製多チャンネルIVL測定装置
(8)屈折率(n)の測定:ジェー・エー・ウーラム社製多入社角分光エリプソメーターVASE
(9)消衰係数(k)の測定:ジェー・エー・ウーラム社製多入社角分光エリプソメーターVASE
(10)インクジェット装置:クラスターテクノロジー(株)製専用ドライバWAVE BUILDER(型番:PIJD-1)、カメラ付き観測装置inkjetlado、自動ステージInkjet Designer及びインクジェットヘッドPIJ-25NSET
MMA:メチルメタクリレート
HEMA:2-ヒドロキシエチルメタクリレート
HPMA:4-ヒドロキシフェニルメタクリレート
HPMA-QD:4-ヒドロキシフェニルメタクリレート1molと1,2-ナフトキノン-2-ジアジド-5-スルホニルクロリド1.1molとの縮合反応によって合成した化合物
CHMI:N-シクロヘキシルマレイミド
PFHMA:2-(パーフルオロヘキシル)エチルメタクリレート
MAA:メタクリル酸
AIBN:α,α'-アゾビスイソブチロニトリル
QD1:α,α,α'-トリス(4-ヒドロキシフェニル)-1-エチル-4-イソプロピルベンゼン1molと1,2-ナフトキノン-2-ジアジド-5-スルホニルクロリド1.5molとの縮合反応によって合成した化合物
GT-401:ブタンテトラカルボン酸テトラ(3,4-エポキシシクロヘキシルメチル)修飾ε-カプロラクトン(商品名:エポリードGT-401、(株)ダイセル製)
PGME:プロピレングリコールモノメチルエーテル
PGMEA:プロピレングリコールモノメチルエーテルアセテート
CHN:シクロヘキサノン
TMAH:テトラメチルアンモニウムヒドロキシド
TBSCl:tert-ブチルジメチルクロロシラン
THF:テトラヒドロフラン
Pd(dba)2:ビス(ジベンジリデンアセトン)パラジウム(0)
[(t-Bu)3PH]BF4:トリtert-ブチルホスフニウムテトラフルオロボラート
t-BuONa:tert-ブトキシナトリウム
TBAF:テトラブチルアンモニウムフルオリド
(1)アクリル重合体の合成
[合成例1-1]
MMA(10.0g)、HEMA(12.5g)、CHMI(20.0g)、HPMA(2.50g)、MAA(5.00g)及びAIBN(3.20g)をPGME(79.8g)に溶解し、60~100℃にて20時間反応させることにより、アクリル重合体P1溶液(固形分濃度40質量%)を得た。アクリル重合体P1のMnは3,700、Mwは6,100であった。
HPMA-QD(2.50g)、PFHMA(7.84g)、MAA(0.70g)、CHMI(1.46g)及びAIBN(0.33g)をCHN(51.3g)に溶解し、110℃にて20時間撹拌して反応させることにより、アクリル重合体P2溶液(固形分濃度20質量%)を得た。アクリル重合体P2のMnは4,300、Mwは6,300であった。
・クロマトグラフ:(株)島津製作所製GPC装置LC-20AD
・カラム:Shodex KF-804L及び803L(昭和電工(株)製)並びにTSK-GEL(東ソー(株)製)を直列接続
・カラム温度:40℃
・検出器:UV検出器(254nm)及びRI検出器
・溶離液:テトラヒドロフラン
・カラム流速:1mL/分
[製造例1]
アクリル重合体P1溶液(5.04g)、アクリル重合体P2溶液(0.05g)、QD1(0.40g)、GT-401(0.09g)及びPGMEA(6.42g)を混合し、室温で3時間撹拌して均一な溶液とし、ポジ型感光性樹脂組成物を得た。
[製造例2]
(株)テクノビジョン製UV-312を用いて10分間オゾン洗浄したITO-ガラス基板上に、スピンコーターを用いて、製造例1で得られたポジ型感光性樹脂組成物を塗布した後、基板をホットプレート上でプリベーク(100℃、120秒間)し、膜厚1.2μmの薄膜を形成した。この薄膜に、長辺200μm、短辺100μmの長方形が多数描かれたパターンのマスクを介して、キヤノン(株)製紫外線照射装置PLA-600FAにより、波長365nmの紫外線を用いて175mJ/cm2で露光した。その後、薄膜を1.0質量%TMAH水溶液に120秒間浸漬して現像を行った後、超純水を用いて薄膜の流水洗浄を20秒間行った。次いで、この長方形パターンが形成された薄膜をポストベーク(230℃、30分間)して硬化させ、隔壁付基板を作製した。
1H-NMR(500MHz, CDCl3) δ [ppm]: 0.75(s, 6H), 1.04(s, 9H), 7.24(t, J=7.5Hz, 1H), 7.34(d, J=8.0Hz, 1H), 7.38(t, J=7.5Hz, 1H), 7.59(d, J=8.5Hz, 1H), 7.73(s, 1H), 7.90(d, J=8.5Hz, 1H), 8.02(d, J=7.5Hz, 1H).
1H-NMR(500MHz, DMSO-d6) δ [ppm]: 0.67(s, 12H), 0.96(s, 18H), 6.85(d, J=8.5Hz, 2H), 7.02(d, J=8.5Hz, 4H), 7.08(d, J=8.5Hz, 4H), 7.11(t, J=7.5Hz, 2H), 7.18-7.22(m, 4H), 7.53(d, J=8.0Hz, 2H), 7.76(brs, 1H), 7.87(d, J=8.5Hz, 2H), 7.90(d, J=7.5Hz, 2H), 7.96(brs, 2H).
1H-NMR(500MHz, THF-d8) δ [ppm]: 0.50(s, 12H), 0.86(s, 18H), 7.03-7.08(m, 15H), 7.11-7.21(m, 8H), 7.26-7.34(m, 10H), 7.42-7.58(m, 15H), 7.88(d, J=8.5Hz, 2H), 7.92(d, J=7.5Hz, 2H), 8.00-8.06(m, 6H).
1H-NMR(500MHz, THF-d8) δ [ppm]: 6.96-7.12(m, 17H), 7.17-7.35(m, 18H), 7.41-7.60(m, 13H), 7.89-7.94(m, 4H), 7.99-8.05(m, 6H), 10.00(brs, 2H).
MALDI-TOF-MS m/Z found: 1253.52 ([M+H]+ calcd: 1253.49)
[実施例1]
アニリン誘導体A0.117g及びアリールスルホン酸エステルC0.233gの混合物(D/H=2.0(モル比))に、トリエチレングリコールブチルメチルエーテル5.425g、マロン酸ジイソプロピル3.022g及びフタル酸ジメチル2.170gを加え、室温で撹拌して溶解させた。そこへ、ジルコニア粒子のPGME分散液(Pixelligent Technologies社製PixClear、平均粒子径7~10nm、ジルコニア濃度:50質量%)0.467gを加え、電荷輸送性ワニスAを調製した。
アニリン誘導体A0.167g及びアリールスルホン酸エステルC0.333g(D/H=2.0(モル比))の混合物に、トリエチレングリコールブチルメチルエーテル4.75g、マロン酸ジイソプロピル2.85g及びフタル酸ジメチル1.9gを加え、室温で撹拌して溶解させ、電荷輸送性ワニスBを調製した。
[実施例2]
電荷輸送性ワニスAを、スピンコーターを用いて石英基板に塗布した後、大気下、120℃で1分間乾燥し、次いで200℃で15分間焼成し、石英基板上に50nmの均一な薄膜を形成した。
電荷輸送性ワニスAのかわりに電荷輸送性ワニスBを用いた以外は、実施例2と同様の方法で石英基板上に50nmの均一な薄膜を形成した。
[実施例3]
電荷輸送性ワニスAを、スピンコーターを用いてITO基板に塗布した後、大気下、120℃で1分間乾燥し、次いで200℃で15分間焼成し、ITO基板上に50nmの均一な薄膜を形成した。ITO基板としては、パターニングされた厚さ50nmのITO膜が表面に形成された、25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除去した。次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いて、アルミニウムを0.2nm/秒にて80nm成膜することで、単層素子を作製した。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、素子は封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。酸素濃度2ppm以下、露点-76℃以下の窒素雰囲気中で、素子を封止基板の間に収め、封止基板を接着剤((株)MORESCO製モレスコモイスチャーカットWB90US(P))により貼り合わせた。この際、捕水剤(ダイニック(株)製HD-071010W-40)を素子と共に封止基板内に収めた。貼り合わせた封止基板に対し、UV光を照射(波長:365nm、照射量:6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着剤を硬化させた。
[実施例4]
電荷輸送性ワニスAを、固形分濃度が2.3質量%となるように溶媒で希釈し、製造例2で作製した隔壁付基板上の長方形の開口部(膜形成領域)に、インクジェット装置を用いて吐出した。なお、電荷輸送性ワニスを希釈する際に、ワニス中の混合溶媒の組成比率が変化しないように、トリエチレングリコールブチルメチルエーテル、マロン酸ジイソプロピル及びフタル酸ジメチルを加えた。得られた塗膜を、その後すぐに、常温で10Pa以下の減圧度(真空度)で15分間減圧乾燥し、次いで常圧で、200℃15分間乾燥して隔壁内に電荷輸送性薄膜を形成し、電荷輸送性薄膜付き基板を得た。なお、電荷輸送性薄膜の開口部中央付近の膜厚が60~80nmとなるように吐出した。
Claims (12)
- (A)表面処理剤で表面修飾されたジルコニア粒子、(B)単分散の電荷輸送性有機化合物及び(C)有機溶媒を含む電荷輸送性ワニスであって、
前記電荷輸送性有機化合物が、アリールアミン誘導体、チオフェン誘導体及びピロール誘導体から選ばれる少なくとも1種を含むものである電荷輸送性ワニス。 - 前記表面処理剤で表面修飾されたジルコニア粒子の平均粒子径が、2~100nmである請求項1記載の電荷輸送性ワニス。
- 前記電荷輸送性有機化合物が、アリールアミン誘導体を含む請求項1又は2記載の電荷輸送性ワニス。
- 前記電荷輸送性有機化合物の分子量が、200~9,000である請求項1~3のいずれか1項記載の電荷輸送性ワニス。
- 前記電荷輸送性有機化合物が、前記有機溶媒に溶解している請求項1~4のいずれか1項記載の電荷輸送性ワニス。
- 更に、(D)ドーパントを含む請求項1~5のいずれか1項記載の電荷輸送性ワニス。
- (D)ドーパントが、アリールスルホン酸エステル化合物である請求項6記載の電荷輸送性ワニス。
- 電荷輸送性ワニス中の固形分濃度が、0.1~20質量%である請求項1~7のいずれか1項記載の電荷輸送性ワニス。
- 粘度が、25℃で1~50mPa・sである請求項1~8のいずれか1項記載の電荷輸送性ワニス。
- 請求項1~9のいずれか1項記載の電荷輸送性ワニスから得られる電荷輸送性薄膜。
- 請求項10記載の電荷輸送性薄膜を備える有機エレクトロルミネッセンス素子。
- 前記電荷輸送性薄膜が、正孔注入層又は正孔輸送層である請求項11記載の有機エレクトロルミネッセンス素子。
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