JP5277578B2 - カルバゾリル基を有する化合物およびその用途 - Google Patents
カルバゾリル基を有する化合物およびその用途 Download PDFInfo
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- JP5277578B2 JP5277578B2 JP2007192729A JP2007192729A JP5277578B2 JP 5277578 B2 JP5277578 B2 JP 5277578B2 JP 2007192729 A JP2007192729 A JP 2007192729A JP 2007192729 A JP2007192729 A JP 2007192729A JP 5277578 B2 JP5277578 B2 JP 5277578B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 116
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 117
- 239000010410 layer Substances 0.000 claims description 130
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004986 diarylamino group Chemical group 0.000 claims description 8
- 238000005401 electroluminescence Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 claims 1
- 150000001716 carbazoles Chemical class 0.000 abstract description 7
- 230000002194 synthesizing effect Effects 0.000 abstract description 7
- 150000002220 fluorenes Chemical class 0.000 abstract description 5
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 4
- 238000001704 evaporation Methods 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000003550 marker Substances 0.000 abstract description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 2
- 230000008020 evaporation Effects 0.000 abstract 2
- 238000002347 injection Methods 0.000 description 64
- 239000007924 injection Substances 0.000 description 64
- 238000000034 method Methods 0.000 description 50
- -1 2-fluorenyl group Chemical group 0.000 description 48
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 230000000694 effects Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 16
- 239000010408 film Substances 0.000 description 16
- 229910052733 gallium Inorganic materials 0.000 description 16
- 229910052782 aluminium Inorganic materials 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- 238000007740 vapor deposition Methods 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 10
- 230000006870 function Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000000859 sublimation Methods 0.000 description 9
- 230000008022 sublimation Effects 0.000 description 9
- 238000001308 synthesis method Methods 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 230000032258 transport Effects 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003967 siloles Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical class C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 2
- WRCUUNRCGDNUQJ-UHFFFAOYSA-N 4-hydroxynaphthalene-1-carbonitrile Chemical compound C1=CC=C2C(O)=CC=C(C#N)C2=C1 WRCUUNRCGDNUQJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VKZIZIKRZSYNOK-UHFFFAOYSA-N C1=CC=C2C=CC(C)(C(O)=O)NC2=C1O Chemical compound C1=CC=C2C=CC(C)(C(O)=O)NC2=C1O VKZIZIKRZSYNOK-UHFFFAOYSA-N 0.000 description 2
- 229910000733 Li alloy Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009500 colour coating Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 150000008376 fluorenones Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 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 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 230000001699 photocatalysis Effects 0.000 description 2
- 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 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000001931 thermography Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- PRVCYYAUAOAWCU-UHFFFAOYSA-N 1-N-naphthalen-1-yl-4-[4-(naphthalen-1-ylamino)-4-phenylcyclohexa-2,5-dien-1-ylidene]-1-N',1-N'-diphenylcyclohexa-2,5-diene-1,1-diamine Chemical compound C1(=CC=CC=C1)N(C1(C=CC(=C2C=CC(NC3=CC=CC4=CC=CC=C34)(C=C2)C2=CC=CC=C2)C=C1)NC1=CC=CC2=CC=CC=C12)C1=CC=CC=C1 PRVCYYAUAOAWCU-UHFFFAOYSA-N 0.000 description 1
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- NLXDFCLCNCWKND-UHFFFAOYSA-N 10-n-(4-butylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1NC1=C(N)C2=CC=CC=C2C2=CC=CC=C12 NLXDFCLCNCWKND-UHFFFAOYSA-N 0.000 description 1
- XFYQEBBUVNLYBR-UHFFFAOYSA-N 12-phthaloperinone Chemical compound C1=CC(N2C(=O)C=3C(=CC=CC=3)C2=N2)=C3C2=CC=CC3=C1 XFYQEBBUVNLYBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical class C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- MUNFOTHAFHGRIM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-oxadiazole Chemical compound C1=CC=C2C(C3=NN=C(O3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MUNFOTHAFHGRIM-UHFFFAOYSA-N 0.000 description 1
- PQYIVUDIIIJJDM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-thiadiazole Chemical compound C1=CC=C2C(C3=NN=C(S3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 PQYIVUDIIIJJDM-UHFFFAOYSA-N 0.000 description 1
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical class BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- BHPFDLWDNJSMOS-UHFFFAOYSA-N 2-(9,10-diphenylanthracen-2-yl)-9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=C(C=C11)C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC=C1 BHPFDLWDNJSMOS-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MWKLOMOIKCPLOY-UHFFFAOYSA-N 3,5-dinaphthalen-1-yl-1h-1,2,4-triazole Chemical compound C1=CC=C2C(C3=NN=C(N3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MWKLOMOIKCPLOY-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
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Images
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Description
すなわち本発明は、下記一般式[1]で表されるカルバゾリル基を有する化合物に関する。
また、本発明は、R3〜R8が水素原子である上記カルバゾリル基を有する化合物に関する。
ジアリールアミノ基としては、N,N−ジフェニルアミノ基、N,N−ビス(m−トリル)アミノ基、N,N−ビス(p−トリル)アミノ基、N,N−ビス(p−ビフェニリル)アミノ基、ビス[4−(4−メチル)ビフェニリル]アミノ基、N−α−ナフチル−N−フェニルアミノ基、N−β−ナフチル−N−フェニルアミノ基等の炭素数2〜26のジアリールアミノ基があげられる。
注入機能;電界印加時に陽極または正孔注入層より正孔を注入することができ、陰極または電子注入層より電子を注入することができる機能
輸送機能;注入した電荷(電子と正孔)を電界の力で移動させる機能
発光機能;電子と正孔の再結合の場を提供し、これを発光につなげる機能
ただし、正孔の注入されやすさと電子の注入されやすさには、違いがあってもよく、また正孔と電子の移動度で表される輸送能に大小があってもよい。
有機EL積層構造体の各層のエネルギー準位を規定し、トンネル注入を利用して発光させるもの(欧州特許第0390551号公報)。
同じくトンネル注入を利用する素子で実施例として白色発光素子が記載されているもの(特開平3−230584号公報)。
二層構造の発光層が記載されているもの(特開平2−220390号公報および特開平2−216790号公報)。
発光層を複数に分割してそれぞれ発光波長の異なる材料で構成されたもの(特開平4−51491号公報)。
青色発光体(蛍光ピーク380〜480nm)と緑色発光体(480〜580nm)とを積層させ、さらに赤色蛍光体を含有させた構成のもの(特開平6−207170号公報)。
青色発光層が青色蛍光色素を含有し、緑色発光層が赤色蛍光色素を含有した領域を有し、さらに緑色蛍光体を含有する構成のもの(特開平7−142169号公報)。
これらの中では、上記の構成のものが特に好ましい。
化合物(1)の合成方法
合成スキームを反応1に示す。(n-C6H13は、n-ヘキシル基を表す。)
合成方法は、以下に示す反応2〜反応7を組み合わせて、表1中の化合物を合成した。
以下、本発明の化合物を有機EL素子用材料として用いた有機EL素子の作成例を下記実施例により説明するが、本発明は下記実施例に限定されるものではない。実施例においては、特に断りのない限り、混合比は全て重量比を示す。蒸着(真空蒸着)は10-6Torrの真空中で、基板加熱、冷却等の温度制御なしの条件下で行った。また、素子の発光特性評価においては、電極面積2mm×2mmの有機EL素子の特性を測定した。
洗浄したITO電極付きガラス板上に、表3のHTM8を真空蒸着して膜厚60nmの正孔注入層を得た。次いで、本発明の表1中の化合物(1)を真空蒸着して膜厚50nmの発光層を得た。さらに、トリス(8−ヒドロキシキノリノ)アルミニウム錯体(Alq3)を真空蒸着して膜厚20nmの電子注入型発光層を作成し、その上に、まずフッ化リチウムを1nm、次いでアルミニウム(Al)を200nm蒸着して電極を形成して、有機EL素子を得た。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表8に示す。
化合物(1)のかわりに表1に示す化合物を用いて発光層を作成した以外は実施例41と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表8に示す。
以下に示す化合物(A)、(B)、(C)、(D)を用いて発光層を作成した以外は実施例41と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表8に示す。
ITO電極付きガラス板上に、表3のHTM8を真空蒸着して膜厚60nmの正孔注入層を得た。次に、表1の化合物(1)と化合物(E)とを100:5の組成比で共蒸着して膜厚45nmの発光層を形成した。さらに化合物(F)を蒸着して膜厚20nmの電子注入層を形成した。その上に、酸化リチウム(Li2O)を1nm、さらにAlを100nm蒸着によって陰極を形成して有機EL素子を得た。この素子は、直流電圧10Vでの外部量子効率は3.5%を示した。また、発光輝度300(cd/m2)で定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表9に示す。
化合物(1)のかわりに表9中の化合物を用いた以外は、実施例81と同様に素子を作成した。これらの素子は、直流電圧10Vでの外部量子効率は3%以上を示し、また、発光輝度200(cd/m2)で定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表9に示す。
化合物(A)もしくは化合物(B)と、化合物(E)とを100:5の重量組成比で共蒸着して膜厚45nmの発光層を作成した以外は実施例81と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表9に示す。
ITO電極付きガラス板上に、表3のHTM8を真空蒸着して膜厚60nmの正孔注入層を得た。次に、化合物(G)と表1の化合物(1)とを100:3の重量組成比で共蒸着して膜厚45nmの発光層を形成した。さらに化合物(H)を蒸着して膜厚20nmの電子注入層を形成した。その上に、酸化リチウム(Li2O)を1nm、さらにAlを100nm蒸着によって陰極を形成して有機EL素子を得た。この素子は、直流電圧10Vでの外部量子効率は3.5%を示した。また、発光輝度300(cd/m2)で定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表10に示す。
化合物(1)のかわりに表10中の化合物を用いた以外は、実施例96と同様に素子を作成した。これら素子は、直流電圧10Vでの外部量子効率は3%以上を示し、また、発光輝度200(cd/m2)で定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表10に示す。
化合物(G)と化合物(A)、もしくは化合物(B)とを100:5の重量組成比で共蒸着して膜厚45nmの発光層を作成した以外は実施例96と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度と半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および100℃の環境で100時間連続駆動させた後の輝度を表10に示す。
洗浄したITO電極付きガラス板上に、表3のHTM8を真空蒸着して膜厚60nmの正孔注入層を得た。次いで、本発明の表1中の化合物(1)を真空蒸着して膜厚60nmの電子輸送層兼発光層を得た。その上に、まずフッ化リチウムを1nm、次いでAlを200nm蒸着して電極を形成して、有機EL素子を得た。この素子は、8Vにて発光輝度5000(cd/m2)の青色発光を示した。
ITO電極付きガラス板上に、銅フタロシアニンを蒸着して膜厚25nmの正孔注入層を形成した。次に、表1の化合物(6)と化合物(I)とを100:3の組成比で共蒸着して膜厚45nmの発光層を形成した。さらに(H)を蒸着して膜厚20nmの正孔ブロッキング層を形成した。その上に、さらに、Alq3を真空蒸着して膜厚30nmの電子注入型発光層を作成し、その上に、まずフッ化リチウムを1nm、次いでAlを200nm蒸着して電極を形成して、有機EL素子を得た。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度半減寿命は、1000時間以上あった。
Claims (8)
- 下記一般式[1]で表されるカルバゾリル基を有する化合物。
一般式[1]
(式中、A1およびA2は、それぞれ独立に、下記一般式[2]で表されるカルバゾリル基を表し、R1およびR2は、それぞれ独立に、水素原子、フェニル基で置換されてもよい1価の脂肪族炭化水素基、アルキル基で置換されてもよい1価の芳香族炭化水素基を表し、R3〜R8は、それぞれ独立に、水素原子、1価の脂肪族炭化水素基、ジアリールアミノ基を表す。)
一般式[2]
(式中、Ar1は1価の芳香族炭化水素基を表し、R9〜R15は、それぞれ独立に、水素原子、1価の芳香族炭化水素基、アリ−ルオキシ基、ジアルキルアミノ基、ジアリールアミノ基を表す。) - R3〜R8が水素原子である請求項1または2記載のカルバゾリル基を有する化合物。
- R9〜R15が水素原子である請求項1ないし3いずれか記載のカルバゾリル基を有する化合物。
- 請求項1〜4いずれか記載のカルバゾリル基を有する化合物を含んでなる有機エレクトロルミネッセンス素子用材料。
- 一対の電極間に発光層または発光層を含む複数層の有機層を形成してなる有機エレクトロルミネッセンス素子において、前記発光層の少なくとも一層が、請求項5記載の有機エレクトロルミネッセンス素子用材料を含んでなる有機エレクトロルミネッセンス素子。
- 一対の電極間に発光層または発光層を含む複数層の有機層を形成してなる有機エレクトロルミネッセンス素子において、前記発光層が、請求項5記載の有機エレクトロルミネッセンス素子用材料を含んでなる有機エレクトロルミネッセンス素子。
- 一対の電極間に発光層または発光層を含む複数層の有機層を形成してなる有機エレクトロルミネッセンス素子において、前記発光層が、リン光発光材料と請求項5記載の有機エレクトロルミネッセンス素子用材料を含んでなる有機エレクトロルミネッセンス素子。
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CN112010759A (zh) * | 2019-05-31 | 2020-12-01 | 北京鼎材科技有限公司 | 一种化合物及其应用、包含其的有机电致发光器件 |
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