JP2020113557A - Compound having azacarbazole structure and organic electroluminescent device - Google Patents
Compound having azacarbazole structure and organic electroluminescent device Download PDFInfo
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- JP2020113557A JP2020113557A JP2017062155A JP2017062155A JP2020113557A JP 2020113557 A JP2020113557 A JP 2020113557A JP 2017062155 A JP2017062155 A JP 2017062155A JP 2017062155 A JP2017062155 A JP 2017062155A JP 2020113557 A JP2020113557 A JP 2020113557A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 135
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 61
- 239000000470 constituent Substances 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 133
- 125000004432 carbon atom Chemical group C* 0.000 claims description 97
- -1 di-substituted amino group Chemical group 0.000 claims description 85
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 57
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000004431 deuterium atom Chemical group 0.000 claims description 14
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000005401 electroluminescence Methods 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 239000010409 thin film Substances 0.000 abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- 238000007740 vapor deposition Methods 0.000 description 36
- 239000010408 film Substances 0.000 description 34
- 238000000034 method Methods 0.000 description 28
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000002356 single layer Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 229940125898 compound 5 Drugs 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 7
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 6
- RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
- 238000001296 phosphorescence spectrum Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 5
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 5
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
- 125000001041 indolyl group Chemical group 0.000 description 5
- 125000005956 isoquinolyl group Chemical group 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000001725 pyrenyl group Chemical group 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 125000005493 quinolyl group Chemical group 0.000 description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 125000004306 triazinyl group Chemical group 0.000 description 5
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- YRTQWABQLUPBDW-UHFFFAOYSA-N 5-(4-bromophenyl)pyrido[4,3-b]indole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=NC=C2C2=CC=CC=C21 YRTQWABQLUPBDW-UHFFFAOYSA-N 0.000 description 4
- CZZLHOWUECFBMS-UHFFFAOYSA-N 8-bromo-5-phenylpyrido[4,3-b]indole Chemical compound C12=CC=NC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 CZZLHOWUECFBMS-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- FHJJVSJWFYYPAC-UHFFFAOYSA-N 3-carbazol-9-yl-9h-carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C2NC3=CC=CC=C3C2=C1 FHJJVSJWFYYPAC-UHFFFAOYSA-N 0.000 description 3
- NTEHSMCNSXIYEW-UHFFFAOYSA-N 5-phenylpyrido[4,3-b]indole Chemical compound C1=CC=CC=C1N1C2=CC=NC=C2C2=CC=CC=C21 NTEHSMCNSXIYEW-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000004322 quinolinols Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
- LKGNNDAICZOLMY-UHFFFAOYSA-N 5-[4-(3-carbazol-9-ylcarbazol-9-yl)phenyl]pyrido[4,3-b]indole Chemical compound C1=CC=C2C(=C1)N(C1=CC=NC=C21)C1=CC=C(N2C3=C(C4=C2C=CC=C4)C=C(N2C4=C(C5=C2C=CC=C5)C=CC=C4)C=C3)C=C1 LKGNNDAICZOLMY-UHFFFAOYSA-N 0.000 description 2
- WUIJXGYSOLXBBG-UHFFFAOYSA-N 8-(3-carbazol-9-ylcarbazol-9-yl)-5-phenylpyrido[4,3-b]indole Chemical compound C1=C2C3=CC(N4C5=C(C6=CC=CC=C46)C=CC=C5)=CC=C3N(C2=CC=C1)C1=CC=C2N(C3=CC=NC=C3C2=C1)C1=CC=CC=C1 WUIJXGYSOLXBBG-UHFFFAOYSA-N 0.000 description 2
- HWTHOPMRUCFPBX-UHFFFAOYSA-N 9,9-diphenyl-10h-acridine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 HWTHOPMRUCFPBX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003609 aryl vinyl group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
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- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
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- 229910052761 rare earth metal Inorganic materials 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 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
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 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 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
本発明は、各種の表示装置に好適な自己発光素子である有機エレクトロルミネッセンス素子に適した化合物と該素子に関するものであり、詳しくはアザカルバゾール構造を有する化合物と、該化合物を用いた有機エレクトロルミネッセンス素子(以下、有機EL素子と略称する)に関するものである。 The present invention relates to a compound suitable for an organic electroluminescence device which is a self-luminous device suitable for various display devices and the device, and more specifically to a compound having an azacarbazole structure and an organic electroluminescence device using the compound. The present invention relates to an element (hereinafter abbreviated as an organic EL element).
有機EL素子は自己発光性素子であるので、液晶素子に比べて明るく視認性に優れ、鮮明な表示が可能であるため、活発な研究がなされてきた。 Since the organic EL element is a self-luminous element, it is brighter and more excellent in visibility than a liquid crystal element, and a clear display is possible. Therefore, active research has been conducted.
近年、素子の発光効率を上げる試みとして、燐光発光体を用いて燐光を発生させる、すなわち三重項励起状態からの発光を利用する素子が開発されている。励起状態の理論によれば、燐光発光を用いた場合には、従来の蛍光発光の約4倍の発光効率が可能になるという、顕著な発光効率の向上が期待される。
1993年にプリンストン大学のM.A.Baldoらは、イリジウム錯体を用いた燐光発光素子によって8%の外部量子効率を実現させた。
また、熱活性化遅延蛍光(TADF)による発光を利用する素子も開発されている。2011年に九州大学の安達らは、熱活性化遅延蛍光材料を用いた素子によって5.3%の外部量子効率を実現させた(例えば、非特許文献1参照)。
In recent years, as an attempt to increase the luminous efficiency of a device, a device has been developed in which phosphorescence is generated using a phosphorescent material, that is, light emission from a triplet excited state is used. According to the theory of excited states, when phosphorescent emission is used, it is expected that the luminous efficiency will be about four times that of conventional fluorescent emission, which is a remarkable improvement in luminous efficiency.
In 1993, Princeton University M. A. Baldo et al. achieved an external quantum efficiency of 8% with a phosphorescent device using an iridium complex.
Further, a device utilizing light emission by thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Adachi et al. of Kyushu University realized an external quantum efficiency of 5.3% by a device using a heat-activated delayed fluorescent material (see Non-Patent Document 1, for example).
発光体は濃度消光を起こすため、一般的にホスト化合物と称される、電荷輸送性の化合物にドープさせることによって担持される。担持される発光体はゲスト化合物と称される。このホスト化合物としては、下記式で表される4,4’−ジ(N−カルバゾリル)ビフェニル(以後、CBPと略称する)が一般に用いられてきた(例えば、非特許文献2参照)。 Since the luminescent material causes concentration quenching, it is supported by being doped with a charge transporting compound generally called a host compound. The supported luminescent material is called a guest compound. As this host compound, 4,4'-di(N-carbazolyl)biphenyl represented by the following formula (hereinafter abbreviated as CBP) has been generally used (for example, see Non-Patent Document 2).
燐光、およびTADF発光素子の研究が進むとともに、発光体とホスト化合物の間のエネルギー移動過程の解明が進み、発光効率を高めるためにはホスト化合物の励起三重項レベルが発光体の励起三重項レベルよりも高くなくてはならないことが明らかとなった。 With the progress of researches on phosphorescence and TADF light-emitting devices, the elucidation of the energy transfer process between the light emitter and the host compound has progressed, and in order to improve the emission efficiency, the excited triplet level of the host compound is the excited triplet level of the light emitter. It became clear that it must be higher than.
下記式で表される青色燐光発光材であるFIrpicを前記CBPにドープして発光層のホスト化合物とした場合、燐光発光素子の外部量子効率は6%程度に留まっている。これはFIrpicの励起三重項レベルが2.67eVであるのに対し、CBPの励起三重項レベルが2.57eVと低いことから、FIrpicによる三重項励起子の閉じ込めが不十分であるからと考えられた。このことは、FIrpicをCBPにドープした薄膜のフォトルミネッセンス強度が温度依存性を示すことによって実証されている(非特許文献3参照)。 When FIrpic, which is a blue phosphorescent light emitting material represented by the following formula, is doped into the CBP to form a host compound for the light emitting layer, the external quantum efficiency of the phosphorescent light emitting element is only about 6%. This is probably because the excited triplet level of FIrpic is 2.67 eV, whereas the excited triplet level of CBP is as low as 2.57 eV, and therefore the confinement of triplet excitons by FIrpic is insufficient. It was This is demonstrated by the temperature dependence of the photoluminescence intensity of the thin film in which FIrpic is doped in CBP (see Non-Patent Document 3).
CBPよりも励起三重項レベルの高いホスト化合物としては、下記で示される3,3’−ジ(9H−カルバゾール−9−イル)−1,1’−ビフェニル(以後、mCBPと略称する)が知られているが、電子輸送性が乏しい。そのため、素子駆動電圧が高まり、満足できる素子特性が得られていなかった。 As a host compound having an excited triplet level higher than that of CBP, 3,3′-di(9H-carbazol-9-yl)-1,1′-biphenyl (hereinafter abbreviated as mCBP) shown below is known. However, the electron transport property is poor. Therefore, the element driving voltage is increased and satisfactory element characteristics have not been obtained.
電子輸送性を高めた材料としてアザカルバゾール骨格を用いた材料も報告されている(例えば特許文献1および特許文献2参照)。しかしながら、さらに発光効率の向上や安定な薄膜を形成する材料が求められている。 A material using an azacarbazole skeleton has also been reported as a material having an enhanced electron transport property (see, for example, Patent Document 1 and Patent Document 2). However, there is a demand for a material that further improves luminous efficiency and forms a stable thin film.
本発明の目的は、高効率の有機EL素子用の材料として、高い励起三重項レベルを有し、燐光およびTADF発光体の三重項励起子を完全に閉じ込めることができ、かつ薄膜安定性の高い、すなわちガラス転移点Tg)の高い、発光層のホスト化合物を提供し、さらにこの化合物を用いて、高効率、高輝度の有機EL素子を提供することにある。 An object of the present invention is as a material for a highly efficient organic EL device, having a high excited triplet level, capable of completely confining triplet excitons of phosphorescence and TADF light emitters, and having high thin film stability. That is, it is to provide a host compound for a light emitting layer having a high glass transition point Tg), and further to provide an organic EL device having high efficiency and high brightness by using this compound.
本発明が提供しようとする有機化合物が具備すべき物理的な特性としては、(1)励起三重項レベルが高いこと、(2)バイポーラ輸送性を有すること、(3)薄膜状態が安定であることをあげることができる。また、本発明が提供しようとする有機エレクトロルミネッセンス素子が具備すべき物理的な特性としては、(1)発光効率が高いこと、(2)発光輝度が高いこと、(3)実用駆動電圧が低いことをあげることができる。 The physical properties that the organic compound to be provided by the present invention should have are (1) high excited triplet level, (2) bipolar transport property, and (3) stable thin film state. I can give you something. The physical characteristics that the organic electroluminescence device to be provided by the present invention should have are (1) high luminous efficiency, (2) high emission luminance, and (3) low practical driving voltage. I can give you something.
そこで本発明者らは上記の目的を達成するために、アザカルバゾール構造が高い励起三重項レベルと電子輸送性能力を有していることに着目して、励起三重項レベルを指標に化合物を設計して化学合成し、実際に励起三重項レベルを測定することによって、燐光およびTADF発光素子に適した特性を有する新規なアザカルバゾール構造を有する化合物を見出した。そして、該化合物を用いて種々の有機エレクトロルミネッセンス素子を試作し、素子の特性評価を行った結果、本発明を完成するに至った。 Therefore, in order to achieve the above object, the present inventors have focused on the fact that the azacarbazole structure has a high excited triplet level and an electron transporting ability, and designed a compound with the excited triplet level as an index. Then, by chemical synthesis, and by actually measuring the excited triplet level, a compound having a novel azacarbazole structure having properties suitable for phosphorescence and TADF light-emitting devices was found. Then, various organic electroluminescence devices were experimentally produced using the compound, and the device characteristics were evaluated. As a result, the present invention was completed.
すなわち本発明によれば、以下の有機EL素子が提供される。 That is, according to the present invention, the following organic EL device is provided.
1)一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機EL素子において、該有機層が発光層であって、下記一般式(1)で表されるアザカルバゾール構造を有する化合物を、該発光層の構成材料として用いていることを特徴とする有機EL素子。 1) In an organic EL device having a pair of electrodes and at least one organic layer sandwiched between the electrodes, the organic layer is a light emitting layer, and a compound having an azacarbazole structure represented by the following general formula (1) is used. And an organic EL device characterized by being used as a constituent material of the light emitting layer.
(式中、A、B、C、D、E、F、G、Hは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Y、Zは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C, D, E, F, G and H is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X, Y and Z are the same or different from each other. Also, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or Represents a di-substituted amino group substituted by a group selected from condensed polycyclic aromatic groups, L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted It represents a substituted fused polycyclic aromatic divalent group.If L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and may be a hydrogen atom or a heavy atom. A hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent Optionally substituted cycloalkyl group having 5 to 10 carbon atoms, optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms, optionally substituted Good straight-chain or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group , A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group (A di-substituted amino group substituted with a group selected from the group groups, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
2)また、本発明は下記一般式(1−1)で表される、アザカルバゾール骨格を有する化合物である。 2) Further, the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-1).
(式中、A、B、C、D、E、F、G、Hは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Y、Zは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C, D, E, F, G and H is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X, Y and Z are the same or different from each other. Also, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or Represents a di-substituted amino group substituted by a group selected from condensed polycyclic aromatic groups, L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted It represents a substituted fused polycyclic aromatic divalent group.If L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and may be a hydrogen atom or a heavy atom. A hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent Optionally substituted cycloalkyl group having 5 to 10 carbon atoms, optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms, optionally substituted Good straight-chain or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group , A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group (A di-substituted amino group substituted with a group selected from the group groups, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
3)また、本発明は下記一般式(1−2)で表される、アザカルバゾール骨格を有する化合物である。 3) Further, the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-2).
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Y、Zは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X, Y and Z may be the same or different from each other, and may be substituted or unsubstituted. Aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by a group, L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic group. Represents a divalent group.If L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom. , A cyano group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a carbon atom which may have a substituent A cycloalkyl group having 5 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and an alkyl group having 1 to 6 carbon atoms which may have a substituent. Linear or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic Substituted with a group selected from a heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group. A substituted disubstituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
4)また、本発明は下記一般式(1−3)で表される、アザカルバゾール骨格を有する化合物である。 4) Further, the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-3).
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
5)また、本発明は下記一般式(1−4)で表される、アザカルバゾール骨格を有する化合物である。 5) Further, the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-4).
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
6)また、本発明は下記一般式(1−5)で表される、アザカルバゾール骨格を有する化合物である。 6) Further, the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-5).
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R7は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 7 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
7)また、本発明は下記一般式(1−6)で表される、アザカルバゾール骨格を有する化合物である。 7) Further, the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-6).
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R7は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) (In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 7 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
一般式(1)中のX,Y,Zで表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」、または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」、または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピリミジニル基、トリアジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、およびカルボリニル基などをあげることができる。 "Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" represented by X, Y, and Z in the general formula (1), or "substituted or unsubstituted fused" The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the "polycyclic aromatic group" is specifically a phenyl group, a biphenylyl group, a terphenylyl group or a naphthyl group. , Anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group , Benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, Examples thereof include an acridinyl group and a carborinyl group.
一般式(1)中のX,Y,Zで表される「置換芳香族炭化水素基」、「置換芳香族複素環基」、または「置換縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基;フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子;メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、n−ヘキシル基、イソへキシル基、ネオへキシル基、n−ヘプチル基、イソへプチル基、ネオへプチル基、n−オクチル基、イソオクチル基、ネオオクチル基などの炭素原子数1ないし8の直鎖状もしくは分岐状のアルキル基;メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数1ないし8の直鎖状もしくは分岐状のアルキルオキシ基;ビニル基、アリル基などのアルケニル基;フェニルオキシ基、トリルオキシ基などのアリールオキシ基;ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基;フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基;ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基;スチリル基、ナフチルビニル基などのアリールビニル基;アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基は、さらに前記例示した置換基が置換していてもよい。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 As a "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group", or "substituted condensed polycyclic aromatic group" represented by X, Y, Z in the general formula (1) Are specifically deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group , Isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl group, neohexyl group, n-heptyl group, isoheptyl group, neoheptyl group, Linear or branched alkyl group having 1 to 8 carbon atoms such as n-octyl group, isooctyl group and neooctyl group; straight chain having 1 to 8 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group Or branched alkyloxy group; alkenyl group such as vinyl group and allyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group , Terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl group, Pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl Groups, aromatic heterocyclic groups such as dibenzofuranyl group, dibenzothienyl group and carborinyl group; arylvinyl groups such as styryl group and naphthylvinyl group; groups such as acyl group such as acetyl group and benzoyl group. However, these substituents may be further substituted with the substituents exemplified above. Further, these substituents may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
一般式(1)中のLで表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」、または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」、または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピリミジニル基、トリアジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、およびカルボリニル基などをあげることができる。 "Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" represented by L in the general formula (1), or "substituted or unsubstituted fused polycyclic aromatic group" The "aromatic hydrocarbon group" in the "group", "aromatic heterocyclic group", or "fused polycyclic aromatic group", specifically, a phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, Phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, Benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, and Examples thereof include a carborinyl group.
一般式(1)中Lで表される「置換芳香族炭化水素基」、「置換芳香族複素環基」、または「置換縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基;フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子;メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、n−ヘキシル基、イソへキシル基、ネオへキシル基、n−ヘプチル基、イソへプチル基、ネオへプチル基、n−オクチル基、イソオクチル基、ネオオクチル基などの炭素原子数1ないし8の直鎖状もしくは分岐状のアルキル基;メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数1ないし8の直鎖状もしくは分岐状のアルキルオキシ基;ビニル基、アリル基などのアルケニル基;フェニルオキシ基、トリルオキシ基などのアリールオキシ基;ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基;フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基;ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基;スチリル基、ナフチルビニル基などのアリールビニル基;アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基は、さらに前記例示した置換基が置換していてもよい。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 Specific examples of the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group”, or “substituted condensed polycyclic aromatic group” represented by L in the general formula (1) include , Deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert. -Butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl group, neohexyl group, n-heptyl group, isoheptyl group, neoheptyl group, n-octyl group, A linear or branched alkyl group having 1 to 8 carbon atoms such as isooctyl group and neooctyl group; a linear or branched alkyl group having 1 to 8 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group Alkyloxy group; alkenyl group such as vinyl group and allyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl Group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, aromatic hydrocarbon group such as triphenylenyl group or condensed polycyclic aromatic group; pyridyl group, pyrimidinyl group, triazinyl group , Thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group Group, aromatic heterocyclic group such as dibenzothienyl group and carborinyl group; arylvinyl group such as styryl group and naphthylvinyl group; group such as acyl group such as acetyl group and benzoyl group; The group may be further substituted with the above-exemplified substituents. Further, these substituents may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
一般式(1)中のR1〜R10で表される「置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基」、または「置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、n−ヘキシル基、シクロペンチル基、シクロヘキシル基、1−アダマンチル基、2−アダマンチル基、ビニル基、アリル基、イソプロペニル基、2−ブテニル基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 “A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R 1 to R 10 in the general formula (1), “having a substituent” Examples of the "optionally substituted cycloalkyl group having 5 to 10 carbon atoms" or "the optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms" include , Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group, 2-butenyl group and the like, these groups are a single bond, a substituted or unsubstituted methylene group, an oxygen atom or They may be bonded to each other via a sulfur atom to form a ring.
一般式(1)中のR1〜R10で表される「置換基を有する炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数5ないし10のシクロアルキル基」、または「置換基を有する炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基;フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子;メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基;ビニル基、アリル基などのアルケニル基;フェニルオキシ基、トリルオキシ基などのアリールオキシ基;ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基;フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基;ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 "A straight-chain or branched alkyl group having 1 to 6 carbon atoms having a substituent" represented by R 1 to R 10 in the general formula (1), "5 to 10 carbon atoms having a substituent""Cycloalkylgroup" or "substituent" in the "C2-C6 linear or branched alkenyl group having a substituent" is, specifically, a deuterium atom, a cyano group, a nitro group. A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group or a propyloxy group; a vinyl group; Alkenyl groups such as allyl groups; aryloxy groups such as phenyloxy groups and tolyloxy groups; arylalkyloxy groups such as benzyloxy groups and phenethyloxy groups; phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups , An aromatic hydrocarbon group such as a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group or a condensed polycyclic aromatic group; a pyridyl group, a pyrimidinyl group, a triazinyl group, a thienyl group, a furyl group, Pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl Examples thereof include groups such as aromatic heterocyclic groups such as groups, and these substituents may be further substituted with the substituents exemplified above. Further, these substituents may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
一般式(1)中のR1〜R10で表される「置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基」における「炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数5ないし10のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、n−プロピルオキシ基、イソプロピルオキシ基、n−ブチルオキシ基、tert−ブチルオキシ基、n−ペンチルオキシ基、n−ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、1−アダマンチルオキシ基、2−アダマンチルオキシ基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent” represented by R 1 to R 10 in the general formula (1) or “having a substituent” "A straight-chain or branched alkyloxy group having 1 to 6 carbon atoms" or "cycloalkyloxy group having 5 to 10 carbon atoms" in the "optionally cycloalkyloxy group having 5 to 10 carbon atoms" Is specifically a methyloxy group, an ethyloxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, a cyclopentyloxy group. , A cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a 1-adamantyloxy group, a 2-adamantyloxy group and the like, and these groups are a single bond, a substituted or unsubstituted methylene group, oxygen They may be bonded to each other via an atom or a sulfur atom to form a ring.
一般式(1)中のR1〜R10で表される「置換基を有する炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数5ないし10のシクロアルキルオキシ基」における「置換基」としては、上記一般式(1)中のR1〜R10で表される「置換基を有する炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数5ないし10のシクロアルキル基」、または「置換基を有する炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “A straight-chain or branched alkyloxy group having 1 to 6 carbon atoms having a substituent” represented by R 1 to R 10 in the general formula (1) or “5 to 5 carbon atoms having a substituent” The "substituent" in the "10 cycloalkyloxy group" is "straight or branched chain having 1 to 6 carbon atoms having a substituent" represented by R 1 to R 10 in the general formula (1). "Alkyl group", "cycloalkyl group having 5 to 10 carbon atoms having a substituent", or "substituent" in "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent" The thing similar to what was shown about it can be mentioned, and the aspect which can be taken can also mention the same thing.
一般式(1)中のX,Y,Zとしては、ジフェニルアミノ基、ジメチルアクリジニル基が好ましく、カルバゾリル基、ジフェニルアクリジニル基がより好ましく、3,9’−ビカルバゾリル基が特に好ましい。 As X, Y and Z in the general formula (1), a diphenylamino group and a dimethylacridinyl group are preferable, a carbazolyl group and a diphenylacridinyl group are more preferable, and a 3,9'-bicarbazolyl group is particularly preferable.
一般式(1)中のLとしては、フェニル基が好ましく、単結合がより好ましい。 As L in the general formula (1), a phenyl group is preferable, and a single bond is more preferable.
一般式(1)中のR1〜R10としては、水素原子、重水素原子が好ましく、合成上の観点から、水素原子がより好ましい。 As R 1 to R 10 in the general formula (1), a hydrogen atom and a deuterium atom are preferable, and a hydrogen atom is more preferable from the viewpoint of synthesis.
本発明に好ましく用いられる一般式(1)で表される、アザカルバゾール構造を有する化合物は、従来の材料より励起三重項レベルが高く、優れた三重項励起子を閉じ込める能力を有し、かつ薄膜状態が安定である。 The compound having an azacarbazole structure, which is preferably used in the present invention and has the azacarbazole structure, has a higher excited triplet level than conventional materials, has an excellent ability to trap triplet excitons, and is a thin film. The condition is stable.
本発明に好ましく用いられる一般式(1)で表される、アザカルバゾール構造を有する化合物は、有機EL素子の発光層の構成材料として使用することができる。従来の材料に比べてバイポーラ輸送性に優れている一般式(1)で表される化合物を用いることにより、発光効率が向上し、実用駆動電圧が低下するという作用を有する。 The compound having an azacarbazole structure, which is represented by the general formula (1) and is preferably used in the present invention, can be used as a constituent material of a light emitting layer of an organic EL device. By using the compound represented by the general formula (1), which is more excellent in bipolar transportability than conventional materials, the luminous efficiency is improved and the practical driving voltage is lowered.
本発明に好ましく用いられる一般式(1)で表される、アザカルバゾール構造を有する化合物は、有機EL素子の発光層のホスト化合物として有用であり、該化合物を用いて有機EL素子を作製することにより、本発明の高効率な有機EL素子を得ることができる。 The compound having an azacarbazole structure represented by the general formula (1), which is preferably used in the present invention, is useful as a host compound for a light emitting layer of an organic EL element, and an organic EL element is produced using the compound. Thus, the highly efficient organic EL device of the present invention can be obtained.
本発明のアザカルバゾール構造を有する化合物は、例えば、以下のように合成できる。
まず、1−(ピリジンー4−イル)−1H−ベンゾ[d][1,2,3]トリアゾールからグレーベ−ウルマン反応によってγ−カルボリン(5H−ピリド[4,3−b]インドール)を合成することができる。このγ−カルボリンに対し、1,4−ジブロモベンゼンを反応させることによって、5−(4−ブロモフェニル)−5H−ピリド[4,3−b]インドールを合成することができる。このブロモ基を有するカルボリン誘導体に対し、バックバルド・ハートウィッグ反応もしくはウルマン反応などの縮合反応を行うことによって、本発明のアザカルバゾール構造を有する化合物を合成することができる。
The compound having the azacarbazole structure of the present invention can be synthesized, for example, as follows.
First, γ-carboline (5H-pyrido[4,3-b]indole) is synthesized from 1-(pyridin-4-yl)-1H-benzo[d][1,2,3]triazole by Greve-Ullman reaction. be able to. By reacting this γ-carboline with 1,4-dibromobenzene, 5-(4-bromophenyl)-5H-pyrido[4,3-b]indole can be synthesized. The compound having an azacarbazole structure of the present invention can be synthesized by subjecting this carboline derivative having a bromo group to a condensation reaction such as the Backward-Hartwig reaction or the Ullmann reaction.
また、γ−カルボリンとヨードベンゼンを反応させることによって、5−フェニル−5H−ピリド[4,3−b]インドールを合成した後に、N−ブロモコハク酸イミドなどによるブロモ化を行うことによって、8−ブロモ−5−フェニル−5H−ピリド[4,3−b]インドールを合成することができる。このブロモ基を有するカルボリン誘導体に対し、バックバルド・ハートウィッグ反応もしくはウルマン反応などの縮合反応を行うことによって、本発明のカルボリン構造を有する化合物を合成することができる。 Moreover, after synthesizing 5-phenyl-5H-pyrido[4,3-b]indole by reacting γ-carboline with iodobenzene, bromination with N-bromosuccinimide or the like is performed to obtain 8- Bromo-5-phenyl-5H-pyrido[4,3-b]indole can be synthesized. The compound having a carboline structure of the present invention can be synthesized by subjecting the carboline derivative having a bromo group to a condensation reaction such as the Backward-Hartwig reaction or the Ullmann reaction.
尚、置換位置の異なるジブロモベンゼン、ブロモ化の試薬、条件を変更することによって、置換位置の異なるブロモ置換体を得ることができる。 In addition, a bromo-substituted product having a different substitution position can be obtained by changing dibromobenzene having a different substitution position, a bromination reagent, and conditions.
一般式(1)で表されるカルボリン構造を有する化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the compounds having the carboline structure represented by the general formula (1), specific examples of preferable compounds are shown below, but the present invention is not limited to these compounds.
これらの化合物の精製はカラムクロマトグラフによる精製、シリカゲル、活性炭、活性白土などによる吸着精製、溶媒による再結晶や晶析法、昇華精製法などによって行った。化合物の同定は、NMR分析によって行った。物性値として、ガラス転移点(Tg)と仕事関数の測定を行った。ガラス転移点(Tg)は薄膜状態の安定性の指標となるものであり、仕事関数は発光ホスト材料としてのエネルギー準位の指標となるものである。 Purification of these compounds was carried out by column chromatography, adsorption purification with silica gel, activated carbon, activated clay, etc., recrystallization with solvent, crystallization method, sublimation purification method and the like. The compound was identified by NMR analysis. As the physical property values, the glass transition point (Tg) and the work function were measured. The glass transition point (Tg) is an index of stability of a thin film state, and the work function is an index of energy level as a light emitting host material.
ガラス転移点(Tg)は、粉体を用いて高感度示差走査熱量計(セイコー・インスツルメント製、DSC6200)によって測定した。 The glass transition point (Tg) was measured with a high-sensitivity differential scanning calorimeter (DSC6200, manufactured by Seiko Instruments) using powder.
仕事関数は、ITO基板の上に100nmの薄膜を作製して、大気中光電子分光装置(理研計器製、AC−3型)を用いて測定した。 The work function was measured by forming a 100 nm thin film on an ITO substrate and using an atmospheric photoelectron spectrometer (AC-3 type, manufactured by Riken Keiki Co., Ltd.).
本発明の化合物の励起三重項レベルは、測定した燐光スペクトルより算出できる。燐光スペクトルは市販の分光光度計を用いて測定できる。一般的な燐光スペクトルの測定方法としては溶媒に溶解し、低温下励起光を照射して測定する方法(例えば、非特許文献4参照)、あるいは、シリコン基板上に蒸着して薄膜とし、低温下励起光を照射して燐光スペクトルを測定する方法などがある。励起三重項レベルは、燐光スペクトルの短波長側の第1ピークの波長あるいは短波長側の立ち上がり位置の波長を読み取り、下記の式に従って光のエネルギー値に換算することによって算出できる。励起三重項レベルは燐光発光体の三重項励起子の閉じ込めの指標となる。 The excited triplet level of the compound of the present invention can be calculated from the measured phosphorescence spectrum. The phosphorescence spectrum can be measured using a commercially available spectrophotometer. As a general phosphorescence spectrum measurement method, a method of dissolving in a solvent and irradiating with excitation light at low temperature for measurement (see, for example, Non-Patent Document 4) or a thin film deposited on a silicon substrate at low temperature There is a method of irradiating excitation light to measure a phosphorescence spectrum. The excited triplet level can be calculated by reading the wavelength of the first peak on the short wavelength side or the wavelength of the rising position on the short wavelength side of the phosphorescence spectrum and converting it to the light energy value according to the following formula. The excited triplet level is a measure of confinement of triplet excitons in the phosphorescent emitter.
ここで、Eは光エネルギーの値を、hはプランク定数(6.63×10−34Js)を、cは光速(3.00×108m/s)を、λは燐光スペクトルの短波長側の立ち上がりの波長(nm)を表す。そして、1eVは1.60×10−19Jとなる。 Here, E is the value of light energy, h is Planck's constant (6.63×10 −34 Js), c is the speed of light (3.00×10 8 m/s), and λ is the short wavelength of the phosphorescence spectrum. Represents the rising wavelength (nm) on the side. Then, 1 eV becomes 1.60×10 −19 J.
本発明の有機EL素子の構造としては、基板上に順次、陽極、正孔注入層、正孔輸送層、電子阻止層、発光層、正孔阻止層、電子輸送層、陰極からなるもの、また、電子輸送層と陰極の間にさらに電子注入層を有するものが挙げられる。これらの多層構造においては有機層を何層か省略することが可能であり、例えば基板上に順次、陽極、正孔輸送層、発光層、電子輸送層、電子注入層、陰極とすることや、陽極、正孔輸送層、発光層、電子輸送層、陰極とすることもできる。 The structure of the organic EL element of the present invention comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and a cathode in this order on the substrate, In addition, an electron injection layer is further provided between the electron transport layer and the cathode. In these multi-layered structures, it is possible to omit some organic layers, for example, sequentially forming an anode, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode on the substrate, It can also be used as an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.
前記発光層、前記正孔輸送層、前記電子輸送層においては、それぞれが2層以上積層された構造であってもよい。 The light emitting layer, the hole transporting layer, and the electron transporting layer may each have a structure in which two or more layers are stacked.
本発明の有機EL素子の陽極としては、ITOや金のような仕事関数の大きな電極材料が用いられる。 For the anode of the organic EL device of the present invention, an electrode material having a large work function such as ITO or gold is used.
本発明の有機EL素子の正孔注入層として、銅フタロシアニンに代表されるポルフィリン化合物の他、ナフタレンジアミン誘導体、スターバースト型のトリフェニルアミン誘導体、分子中にトリフェニルアミン構造を3個以上、単結合またはヘテロ原子を含まない2価基で連結した構造を有するアリールアミン化合物などのトリフェニルアミン3量体および4量体、ヘキサシアノアザトリフェニレンのようなアクセプター性の複素環化合物や塗布型の高分子材料を用いることができる。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the hole injection layer of the organic EL device of the present invention, in addition to a porphyrin compound represented by copper phthalocyanine, a naphthalenediamine derivative, a starburst type triphenylamine derivative, three or more triphenylamine structures in a molecule, Triphenylamine trimers and tetramers such as arylamine compounds having a structure linked by a divalent group containing no bond or hetero atom, acceptor type heterocyclic compounds such as hexacyanoazatriphenylene, and coating type polymers Materials can be used. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an inkjet method.
本発明の有機EL素子の正孔輸送層として、m−カルバゾリルフェニル基を含有する化合物の他、N,N’−ジフェニル−N,N’−ジ(m−トリル)−ベンジジン(以後、TPDと略称する)やN,N’−ジフェニル−N,N’−ジ(α−ナフチル)−ベンジジン(以後、NPDと略称する)、N,N,N’,N’−テトラビフェニリルベンジジンなどのベンジジン誘導体、1,1−ビス[(ジ−4−トリルアミノ)フェニル]シクロヘキサン(以後、TAPCと略称する)、種々のトリフェニルアミン3量体および4量体やカルバゾール誘導体などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。また、正孔の注入・輸送層として、ポリ(3,4−エチレンジオキシチオフェン)(以後、PEDOTと略称する)/ポリ(スチレンスルフォネート)(以後、PSSと略称する)などの塗布型の高分子材料を用いることができる。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the hole transport layer of the organic EL device of the present invention, in addition to a compound containing an m-carbazolylphenyl group, N,N′-diphenyl-N,N′-di(m-tolyl)-benzidine (hereinafter, TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (hereinafter abbreviated as NPD), N,N,N',N'-tetrabiphenylylbenzidine, etc. 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine trimers and tetramers, carbazole derivatives and the like can be used. .. These may be formed as a single film, but may be used as a single layer formed by mixing with other materials, and may be formed as a single layer, as a single layer, or as a mixed layer. A laminated structure of a layer formed by mixing with a layer formed alone may be used. Further, as a hole injecting/transporting layer, a coating type such as poly(3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT)/poly(styrene sulfonate) (hereinafter abbreviated as PSS) Polymer materials of In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an inkjet method.
また、正孔注入層あるいは正孔輸送層において、該層に通常使用される材料に対し、さらにトリスブロモフェニルアミンヘキサクロルアンチモンをPドーピングしたものや、TPDの構造をその部分構造に有する高分子化合物などを用いることができる。 Further, in a hole injection layer or a hole transport layer, trisbromophenylamine hexachloroantimony is further P-doped with respect to a material usually used for the layer, or a polymer having a TPD structure in its partial structure. A compound or the like can be used.
本発明の有機EL素子の電子阻止層として、4,4’,4’’−トリ(N−カルバゾリル)トリフェニルアミン(以後、TCTAと略称する)、9,9−ビス[4−(カルバゾール−9−イル)フェニル]フルオレン、1,3−ビス(カルバゾール−9−イル)ベンゼン(以後、mCPと略称する)、2,2−ビス(4−カルバゾール−9−イルフェニル)アダマンタン(以後、Ad−Czと略称する)などのカルバゾール誘導体、9−[4−(カルバゾール−9−イル)フェニル]−9−[4−(トリフェニルシリル)フェニル]−9H−フルオレンに代表されるトリフェニルシリル基とトリアリールアミン構造を有する化合物などの電子阻止作用を有する化合物を用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the electron blocking layer of the organic EL device of the present invention, 4,4′,4″-tri(N-carbazolyl)triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis[4-(carbazole- 9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter Ad A carbazole derivative such as -Cz), a triphenylsilyl group represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene. And a compound having an electron blocking action such as a compound having a triarylamine structure can be used. These may be formed as a single film, but may be used as a single layer formed by mixing with other materials, and may be formed as a single layer, as a single layer, or as a mixed layer. It may have a laminated structure of a layer formed by mixing with a layer formed alone. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an inkjet method.
本発明の有機EL素子の発光層として、トリス(8−ヒドロキシキノリン)アルミニウム(以後、Alq3と略称する)をはじめとするキノリノール誘導体の金属錯体などの各種金属錯体、アントラセン誘導体、ビススチリルベンゼン誘導体、ピレン誘導体、オキサゾール誘導体、ポリパラフェニレンビニレン誘導体などを用いることができる。また、発光層をホスト材料とドーパント材料とで構成してもよく、この場合、ホスト材料として本発明の一般式(1)で表されるトリフェニルシリルピリジル基とカルバゾール環構造を有する化合物、mCP、チアゾール誘導体、ベンズイミダゾール誘導体、ポリジアルキルフルオレン誘導体などを用いることができる。またドーパント材料としては、キナクリドン、クマリン、ルブレン、アントラセン、ペリレンおよびそれらの誘導体、ベンゾピラン誘導体、ローダミン誘導体、アミノスチリル誘導体などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。 As the light emitting layer of the organic EL device of the present invention, various metal complexes such as tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq 3 ) and other metal complexes of quinolinol derivatives, anthracene derivatives, and bisstyrylbenzene derivatives. , A pyrene derivative, an oxazole derivative, a polyparaphenylene vinylene derivative, and the like can be used. In addition, the light emitting layer may be composed of a host material and a dopant material. In this case, a compound having a triphenylsilylpyridyl group represented by the general formula (1) of the present invention and a carbazole ring structure as a host material, mCP , A thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative and the like can be used. As the dopant material, quinacridone, coumarin, rubrene, anthracene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives and the like can be used. These may be formed as a single film, but may be used as a single layer formed by mixing with other materials, and may be formed as a single layer, as a single layer, or as a mixed layer. It may have a laminated structure of a layer formed by mixing with a layer formed alone.
また、発光材料として燐光性の発光材料を使用することも可能である。燐光性の発光体としては、イリジウムや白金などの金属錯体の燐光発光体を使用することができる。Ir(ppy)3などの緑色の燐光発光体、FIrpic、FIr6などの青色の燐光発光体、Btp2Ir(acac)、Ir(piq)3などの赤色の燐光発光体などが用いられ、このときのホスト材料としては本発明の一般式(1)で表されるトリフェニルシリルピリジル基とカルバゾール環構造を有する化合物の他、正孔注入・輸送性のホスト材料として、CBPやTCTA、mCPなどのカルバゾール誘導体などを用いることができる。電子輸送性のホスト材料として、p−ビス(トリフェニルシリル)ベンゼン(以後、UGH2と略称する)や2,2’,2’’−(1,3,5−フェニレン)−トリス(1−フェニル−1H−ベンズイミダゾール)(以後、TPBIと略称する)などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。 It is also possible to use a phosphorescent light emitting material as the light emitting material. As the phosphorescent luminescent material, a phosphorescent luminescent material of a metal complex such as iridium or platinum can be used. A green phosphorescent material such as Ir(ppy) 3 or a blue phosphorescent material such as FIrpic or FIr6 or a red phosphorescent material such as Btp 2 Ir(acac) or Ir(piq) 3 is used. Examples of the host material include a compound having a triphenylsilylpyridyl group represented by the general formula (1) and a carbazole ring structure of the present invention, and a hole injection/transporting host material such as CBP, TCTA, or mCP. A carbazole derivative or the like can be used. As an electron-transporting host material, p-bis(triphenylsilyl)benzene (hereinafter abbreviated as UGH2) or 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) and the like can be used. These may be formed as a single film, but may be used as a single layer formed by mixing with other materials, and may be formed as a single layer, as a single layer, or as a mixed layer. It may have a laminated structure of a layer formed by mixing with a layer formed alone.
燐光性の発光材料のホスト材料へのドープは濃度消光を避けるため、発光層全体に対して1〜30重量パーセントの範囲で、共蒸着によってドープすることが好ましい。 In order to avoid concentration quenching, it is preferable to dope the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an inkjet method.
また、本発明の化合物を用いて作製した発光層に、仕事関数の異なる化合物をホスト材料として用いて作製した発光層を隣接させて積層した構造の素子を作製することができる(例えば、非特許文献5参照)。 In addition, an element having a structure in which a light-emitting layer manufactured using the compound of the present invention is adjacent to a light-emitting layer manufactured using a compound having a different work function as a host material can be manufactured (for example, a non-patent document). Reference 5).
本発明の有機EL素子の正孔阻止層として、バソクプロイン(以後、BCPと略称する)などのフェナントロリン誘導体や、アルミニウム(III)ビス(2−メチル−8−キノリナート)−4−フェニルフェノレート(以後、BAlqと略称する)などのキノリノール誘導体の金属錯体の他、各種の希土類錯体、オキサゾール誘導体、トリアゾール誘導体、トリアジン誘導体など、正孔阻止作用を有する化合物を用いることができる。これらの材料は電子輸送層の材料を兼ねてもよい。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the hole blocking layer of the organic EL device of the present invention, a phenanthroline derivative such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis(2-methyl-8-quinolinato)-4-phenylphenolate (hereinafter , BAlq) and other metal complexes of quinolinol derivatives, as well as various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and other compounds having a hole blocking action can be used. These materials may also serve as the material of the electron transport layer. These may be formed as a single film, but may be used as a single layer formed by mixing with other materials, and may be formed as a single layer, as a single layer, or as a mixed layer. It may have a laminated structure of a layer formed by mixing with a layer formed alone. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an inkjet method.
本発明の有機EL素子の電子輸送層として、Alq3、BAlqをはじめとするキノリノール誘導体の金属錯体の他、各種金属錯体、トリアゾール誘導体、トリアジン誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、カルボジイミド誘導体、キノキサリン誘導体、フェナントロリン誘導体、シロール誘導体、TPBIなどのベンズイミダゾール誘導体などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the electron transport layer of the organic EL device of the present invention, in addition to metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline. A derivative, a phenanthroline derivative, a silole derivative, a benzimidazole derivative such as TPBI, or the like can be used. These may be formed as a single film, but may be used as a single layer formed by mixing with other materials, and may be formed as a single layer, as a single layer, or as a mixed layer. It may have a laminated structure of a layer formed by mixing with a layer formed alone. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an inkjet method.
本発明の有機EL素子の電子注入層として、フッ化リチウム、フッ化セシウムなどのアルカリ金属塩、フッ化マグネシウムなどのアルカリ土類金属塩、酸化アルミニウムなどの金属酸化物などを用いることができるが、電子輸送層と陰極の好ましい選択においては、これを省略することができる。 As the electron injection layer of the organic EL device of the present invention, an alkali metal salt such as lithium fluoride or cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, a metal oxide such as aluminum oxide, or the like can be used. In a preferred choice of electron transport layer and cathode, this can be omitted.
さらに、電子注入層あるいは電子輸送層において、該層に通常使用される材料に対し、さらにセシウムなどの金属をNドーピングしたものを用いることができる。 Furthermore, in the electron injecting layer or the electron transporting layer, a material usually used for the layer may be N-doped with a metal such as cesium.
本発明の有機EL素子の陰極として、アルミニウムのような仕事関数の低い電極材料や、マグネシウム銀合金、マグネシウムインジウム合金、アルミニウムマグネシウム合金のような、より仕事関数の低い合金が電極材料として用いられる。 As the cathode of the organic EL device of the present invention, an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as an electrode material.
以下、本発明の実施の形態について、実施例により具体的に説明するが、本発明は、以下の実施例に限定されるものではない。 Hereinafter, the embodiments of the present invention will be specifically described with reference to Examples, but the present invention is not limited to the following Examples.
<9,9−ジフェニル−10−(5−フェニル−5H−ピリド[4,3−b]インドール−8−イル)−9,10−ジヒドロアクリジン(化合物1)の合成>
窒素置換した反応容器中、5H−ピリド[4,3−b]インドール(100g)、ヨードベンゼン(79.5ml)、銅粉(18.9g)、炭酸カリウム(164g)、ジメチルスルホキシド(4.2ml)をトルエン(200ml)に懸濁させた。トルエンを除去しながら170℃まで加熱し、そのまま3時間撹拌した。120℃まで放冷後、トルエン(1L)を注加し、90℃で30分撹拌した。80℃まで放冷後、濾過した。濾液にNHシリカゲルを加えて30分撹拌してから濾過した。溶媒を留去し、5−フェニル−5H−ピリド[4,3−b]インドール(収率77%)の薄褐色油を得た。
窒素置換した反応容器中、5−フェニル−5H−ピリド[4,3−b]インドール(111g)をクロロホルム(770ml)に溶解させた。反応液に臭素(218g)を滴下し、60℃で1時間撹拌した。反応容器を水浴させながら、飽和チオ硫酸ナトリウム水溶液(600ml)を注加した。その後、炭酸カリウム水溶液で中和してからクロロホルムで抽出した。有機層にNHシリカゲルを加えて30分撹拌してから濾過し、濾液の溶媒を留去した。得られた濃縮物にトルエン(1L)を加えて溶解後、シリカゲルを加え目的物を吸着させた。濾過後、シリカゲルに溶離液(1L、クロロホルム/メタノール=9/1)を加えて撹拌し、濾過した。溶媒を留去し、8−ブロモ−5−フェニル−5H−ピリド[4,3−b]インドール(収率81%)の白色固体を得た。
窒素置換した反応容器中、9,9−ジフェニル−9,10−ジヒドロアクリジン(1.24g)、8−ブロモ−5−フェニル−5H−ピリド[4,3−b]インドール(1.00g)、トリ−t−ブチルホスホニウムテトラフルオロボラート(0.13g)、ナトリウムt−ブトキシド(0.34g)をトルエン(100ml)に懸濁させた。反応系中を3回アルゴン置換した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)クロロホルム付加体(0.10g)を加え、22時間加熱還流した。室温まで放冷後、飽和食塩水を加え反応を停止させた。セライト濾過を行った後、酢酸エチルで抽出し、溶媒を留去した。得られた濃縮物をカラムクロマトグラフィーで精製し、9,9−ジフェニル−10−(5−フェニル−5H−ピリド[4,3−b]インドール−8−イル)−9,10−ジヒドロアクリジン(収率37%)の白色粉末を得た。
<Synthesis of 9,9-diphenyl-10-(5-phenyl-5H-pyrido[4,3-b]indol-8-yl)-9,10-dihydroacridine (Compound 1)>
In a reaction vessel purged with nitrogen, 5H-pyrido[4,3-b]indole (100 g), iodobenzene (79.5 ml), copper powder (18.9 g), potassium carbonate (164 g), dimethyl sulfoxide (4.2 ml). ) Was suspended in toluene (200 ml). While removing toluene, the mixture was heated to 170° C. and stirred for 3 hours as it was. After allowing to cool to 120° C., toluene (1 L) was added, and the mixture was stirred at 90° C. for 30 minutes. After cooling to 80° C., the mixture was filtered. NH silica gel was added to the filtrate, and the mixture was stirred for 30 minutes and then filtered. The solvent was distilled off to obtain a light brown oil of 5-phenyl-5H-pyrido[4,3-b]indole (yield 77%).
5-Phenyl-5H-pyrido[4,3-b]indole (111 g) was dissolved in chloroform (770 ml) in a reaction vessel purged with nitrogen. Bromine (218 g) was added dropwise to the reaction solution, and the mixture was stirred at 60° C. for 1 hour. A saturated aqueous sodium thiosulfate solution (600 ml) was added while the reaction vessel was kept in a water bath. Then, it was neutralized with an aqueous potassium carbonate solution and extracted with chloroform. NH silica gel was added to the organic layer, the mixture was stirred for 30 minutes and then filtered, and the solvent of the filtrate was evaporated. Toluene (1 L) was added to the obtained concentrate to dissolve it, and silica gel was added to adsorb the desired product. After filtration, the eluent (1 L, chloroform/methanol=9/1) was added to silica gel, and the mixture was stirred and filtered. The solvent was evaporated, and a white solid of 8-bromo-5-phenyl-5H-pyrido[4,3-b]indole (yield 81%) was obtained.
In a reaction vessel purged with nitrogen, 9,9-diphenyl-9,10-dihydroacridine (1.24 g), 8-bromo-5-phenyl-5H-pyrido[4,3-b]indole (1.00 g), Tri-t-butylphosphonium tetrafluoroborate (0.13 g) and sodium t-butoxide (0.34 g) were suspended in toluene (100 ml). After purging the reaction system with argon three times, tris(dibenzylideneacetone)dipalladium(0)chloroform adduct (0.10 g) was added, and the mixture was heated under reflux for 22 hr. After allowing to cool to room temperature, saturated saline was added to stop the reaction. After filtration through Celite, the mixture was extracted with ethyl acetate and the solvent was evaporated. The obtained concentrate was purified by column chromatography to obtain 9,9-diphenyl-10-(5-phenyl-5H-pyrido[4,3-b]indol-8-yl)-9,10-dihydroacridine( A white powder with a yield of 37% was obtained.
得られた白色固体についてNMRを使用して構造を同定した。1H−NMR測定結果を図1に示した。
1H−NMR(CDCl3)で以下の29水素のシグナルを検出した。
δ(ppm)=6.48(2H)、6.87−6.90(2H)、6.93(2H)、7.01−7.06(6H)、7.17(1H)、7.25−7.32(7H)、7.54−7.57(2H)、7.60(2H)、7.65−7.7.68(2H)、7.87(1H)、8.55(1H)、9.26(1H)
The structure of the obtained white solid was identified using NMR. The 1 H-NMR measurement result is shown in FIG. 1.
The following 29 hydrogen signals were detected by 1 H-NMR (CDCl 3 ).
δ (ppm)=6.48 (2H), 6.87-6.90 (2H), 6.93 (2H), 7.01-7.06 (6H), 7.17 (1H), 7. 25-7.32 (7H), 7.54-7.57 (2H), 7.60 (2H), 7.65-7.7.68 (2H), 7.87 (1H), 8.55. (1H), 9.26 (1H)
<10−(4−(5H−ピリド[4,3−b]インドール−5−イル)フェニル−9,9−ジフェニル−9,10−ジヒドロアクリジン(化合物2)の合成>
窒素置換した反応容器中、1,4−ジブロモベンゼン(28.07g)、銅粉、(0.96g)、炭酸カリウム(8.24g)、ジメチルスルホキシド(0.7ml)をODB(40ml)に懸濁させた。170℃で1時間撹拌した後、5H−ピリド[4,3−b]インドール(5.00g)を加え、そのままの温度で8時間撹拌した。50℃まで放冷後、クロロホルム(100ml)を加えて30分撹拌した。セライト濾過を行った後、溶媒を留去した。得られた濃縮物をカラムクロマトグラフィーで精製し、5−(4−ブロモフェニル)−5H−ピリド[4,3−b]インドール(収率67%)の淡黄色粉末を得た。
窒素置換した反応容器中、9,9−ジフェニル−9,10−ジヒドロアクリジン(3.00g)、5−(4−ブロモフェニル)−5H−ピリド[4,3−b]インドール(3.50g)、N−フェニル−2−(ジ−t−ブチルホスフィノ)インドール(0.36g)、ナトリウムt−ブトキシド(0.91g)をトルエン(100ml)に懸濁させた。反応系中を3回アルゴン置換した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)クロロホルム付加体(0.28g)を加え、9時間加熱還流した。室温まで放冷後、飽和食塩水を加え反応を停止させた。セライト濾過を行った後、酢酸エチルで抽出し、溶媒を留去した。得られた濃縮物をカラムクロマトグラフィーで精製し、10−(4−(5H−ピリド[4,3−b]インドール−5−イル)フェニル−9,9−ジフェニル−9,10−ジヒドロアクリジン(収率36%)の淡黄色粉末を得た。
<Synthesis of 10-(4-(5H-pyrido[4,3-b]indol-5-yl)phenyl-9,9-diphenyl-9,10-dihydroacridine (Compound 2)>
In a reaction vessel purged with nitrogen, 1,4-dibromobenzene (28.07 g), copper powder, (0.96 g), potassium carbonate (8.24 g) and dimethyl sulfoxide (0.7 ml) were suspended in ODB (40 ml). Made cloudy. After stirring at 170° C. for 1 hour, 5H-pyrido[4,3-b]indole (5.00 g) was added, and the mixture was stirred at that temperature for 8 hours. After cooling to 50° C., chloroform (100 ml) was added and the mixture was stirred for 30 minutes. After filtration through Celite, the solvent was distilled off. The obtained concentrate was purified by column chromatography to obtain 5-(4-bromophenyl)-5H-pyrido[4,3-b]indole (yield 67%) as a pale yellow powder.
In a reaction vessel purged with nitrogen, 9,9-diphenyl-9,10-dihydroacridine (3.00 g), 5-(4-bromophenyl)-5H-pyrido[4,3-b]indole (3.50 g) , N-phenyl-2-(di-t-butylphosphino)indole (0.36 g) and sodium t-butoxide (0.91 g) were suspended in toluene (100 ml). After purging the reaction system with argon 3 times, tris(dibenzylideneacetone)dipalladium(0)chloroform adduct (0.28 g) was added, and the mixture was heated under reflux for 9 hr. After allowing to cool to room temperature, saturated saline was added to stop the reaction. After filtration through Celite, the mixture was extracted with ethyl acetate and the solvent was evaporated. The obtained concentrate was purified by column chromatography to obtain 10-(4-(5H-pyrido[4,3-b]indol-5-yl)phenyl-9,9-diphenyl-9,10-dihydroacridine( A pale yellow powder with a yield of 36% was obtained.
得られた淡黄色固体についてNMRを使用して構造を同定した。1H−NMR測定結果を図2に示した。
1H−NMR(CDCl3)で以下の29水素のシグナルを検出した。
δ(ppm)=6.58(2H)、6.95(4H)、7.02(4H)、7.13−7.17(2H)、7.27−7.30(6H)、7.33(2H)、7.40−7.43(2H)、7.51−7.54(2H)、7.72(2H)、8.24(1H)、8.57(1H)、9.41(1H)
The structure of the obtained pale yellow solid was identified using NMR. The 1H-NMR measurement result is shown in FIG.
The following 29 hydrogen signals were detected by 1 H-NMR (CDCl 3 ).
δ (ppm)=6.58 (2H), 6.95 (4H), 7.02 (4H), 7.13-7.17 (2H), 7.27-7.30 (6H), 7. 33(2H), 7.40-7.43(2H), 7.51-7.54(2H), 7.72(2H), 8.24(1H), 8.57(1H), 9. 41 (1H)
<9−(5−フェニル−5H−ピリド[4,3−b]インドール−8−イル)−9H−3,9’−ビカルバゾール(化合物4)の合成>
窒素置換した反応容器中、9H−3,9’−ビカルバゾール(1.14g)、8−ブロモ−5−フェニル−5H−ピリド[4,3−b]インドール(1.00g)、リン酸カリウム(1.33g)を1,4−ジオキサン(30ml)に懸濁させ、trance−1,2−ジアミノシクロヘキサン(0.11g)、次いでヨウ化銅(0.18g)を加え、21時間加熱還流した。室温まで放冷後、飽和食塩水を加え反応を停止させた。セライト濾過を行った後、トルエンで抽出し、溶媒を留去した。得られた濃縮物をカラムクロマトグラフィーで精製し、9−(5−フェニル−5H−ピリド[4,3−b]インドール−8−イル)−9H−3,9’−ビカルバゾール(収率63%)の白色粉末を得た。
<Synthesis of 9-(5-phenyl-5H-pyrido[4,3-b]indol-8-yl)-9H-3,9′-bicarbazole (Compound 4)>
In a reaction vessel purged with nitrogen, 9H-3,9′-bicarbazole (1.14 g), 8-bromo-5-phenyl-5H-pyrido[4,3-b]indole (1.00 g), potassium phosphate. (1.33 g) was suspended in 1,4-dioxane (30 ml), and trans-1,2-diaminocyclohexane (0.11 g) and then copper iodide (0.18 g) were added, and the mixture was heated under reflux for 21 hours. .. After allowing to cool to room temperature, saturated saline was added to stop the reaction. After filtration through Celite, the mixture was extracted with toluene and the solvent was distilled off. The obtained concentrate was purified by column chromatography to give 9-(5-phenyl-5H-pyrido[4,3-b]indol-8-yl)-9H-3,9'-bicarbazole (yield 63 %) white powder was obtained.
得られた白色粉末についてNMRを使用して構造を同定した。1H−NMR測定結果を図3に示した。
1H−NMR(DMSO−d6)で以下の26水素のシグナルを検出した。
δ(ppm)=7.29−7.36(3H)、7.38(2H)、7.44−7.48(4H)、7.52(1H)、7.61−7.67(3H)、7.73−7.83(5H)、7.85(1H)、8.29(2H)、8.39(1H)、8.56(1H)、8.58(1H)、8.83(1H)、9.61(1H)
The structure of the obtained white powder was identified using NMR. The 1H-NMR measurement result is shown in FIG.
The following 26 hydrogen signals were detected by 1H-NMR (DMSO-d6).
δ (ppm)=7.29-7.36 (3H), 7.38 (2H), 7.44-7.48 (4H), 7.52 (1H), 7.61-7.67 (3H) ), 7.73-7.83(5H), 7.85(1H), 8.29(2H), 8.39(1H), 8.56(1H), 8.58(1H), 8. 83 (1H), 9.61 (1H)
<9−(4−(5H−ピリド[4,3−b]インドール−5−イル)フェニル)−9H−3,9’−ビカルバゾール(化合物5)の合成>
窒素置換した反応容器中、9H−3,9’−ビカルバゾール(1.00g)、5−(4−ブロモフェニル)−5H−ピリド[4,3−b]インドール(1.13g)、リン酸カリウム(1.34g)を1,4−ジオキサン(30ml)に懸濁させ、trance−1,2−ジアミノシクロヘキサン(0.11g)、次いでヨウ化銅(0.20g)を加え、32時間加熱還流した。室温まで放冷後、飽和食塩水を加え反応を停止させた。セライト濾過を行った後、トルエンで抽出し、溶媒を留去した。得られた濃縮物をカラムクロマトグラフィーで精製し、9−(4−(5H−ピリド[4,3−b]インドール−5−イル)フェニル)−9H−3,9’−ビカルバゾール(収率79%)の白色粉末を得た。
<Synthesis of 9-(4-(5H-pyrido[4,3-b]indol-5-yl)phenyl)-9H-3,9′-bicarbazole (Compound 5)>
In a reaction vessel purged with nitrogen, 9H-3,9'-bicarbazole (1.00 g), 5-(4-bromophenyl)-5H-pyrido[4,3-b]indole (1.13 g), phosphoric acid Potassium (1.34 g) was suspended in 1,4-dioxane (30 ml), and trans-1,2-diaminocyclohexane (0.11 g) and then copper iodide (0.20 g) were added, and the mixture was heated under reflux for 32 hours. did. After allowing to cool to room temperature, saturated saline was added to stop the reaction. After filtration through Celite, the mixture was extracted with toluene and the solvent was distilled off. The obtained concentrate was purified by column chromatography to give 9-(4-(5H-pyrido[4,3-b]indol-5-yl)phenyl)-9H-3,9'-bicarbazole (yield 79%) of white powder was obtained.
得られた白色粉末についてNMRを使用して構造を同定した。1H−NMR測定結果を図4に示した。
1H−NMR(DMSO−d6)で以下の26水素のシグナルを検出した。
δ(ppm)=7.31(2H)、7.36−7.41(3H)、7.44−7.47(3H)、7.69(3H)、7.67−7.70(3H)、7.86(1H)、8.02(2H)、8.07(2H)、8.30(2H)、8.40(1H)、8.43(1H)、8.57(1H)、8.60(1H)、9.54(1H)
The structure of the obtained white powder was identified using NMR. The 1 H-NMR measurement result is shown in FIG.
The following 26 hydrogen signals were detected by 1H-NMR (DMSO-d6).
δ (ppm)=7.31 (2H), 7.36-7.41 (3H), 7.44-7.47 (3H), 7.69 (3H), 7.67-7.70 (3H) ), 7.86 (1H), 8.02 (2H), 8.07 (2H), 8.30 (2H), 8.40 (1H), 8.43 (1H), 8.57 (1H) , 8.60 (1H), 9.54 (1H)
本発明の化合物について、高感度示差走査熱量計(セイコー・インスツルメント製、DSC200)によってガラス転移点を求めた。
ガラス転移点
本発明実施例1の化合物 N/A
本発明実施例2の化合物 141℃
本発明実施例3の化合物 152℃
本発明実施例4の化合物 150℃
The glass transition point of the compound of the present invention was determined by a high-sensitivity differential scanning calorimeter (DSC200, manufactured by Seiko Instruments).
Glass transition point Compound N/A of Example 1 of the present invention
Compound of Example 2 of the present invention 141° C.
Compound of Example 3 of the invention 152° C.
Compound of Example 4 of the present invention 150° C.
本発明の化合物を用いて、ITO基板の上に膜厚100nmの蒸着膜を作製し、大気中光電子分光装置(理研計器製、AC−3型)で仕事関数を測定した。
仕事関数
本発明実施例1の化合物 5.92eV
本発明実施例2の化合物 5.85eV
本発明実施例3の化合物 5.80eV
本発明実施例4の化合物 5.98eV
mCBP 6.20eV
Using the compound of the present invention, a vapor-deposited film having a thickness of 100 nm was formed on an ITO substrate, and the work function was measured by an atmospheric photoelectron spectrometer (AC-3 type, manufactured by Riken Keiki Co., Ltd.).
Work Function Compound of Example 1 of the Present Invention 5.92 eV
Compound of Example 2 of the present invention 5.85 eV
Compound of Example 3 of the present invention 5.80 eV
Compound of Example 4 of the present invention 5.98 eV
mCBP 6.20 eV
このように本発明の化合物は、発光ホストとして一般的に用いられるmCBPと同程度の、発光層の材料として好適なエネルギー準位を有している。 Thus, the compound of the present invention has an energy level similar to that of mCBP generally used as a light emitting host and suitable as a material for a light emitting layer.
本発明実施例1の化合物(化合物1)について、10−5mol/Lのトルエン溶液を調製した。このトルエン溶液について、窒素を通気しながら300Kで紫外光を照射したところ、ピーク波長が392nmの蛍光を観測した。 With respect to the compound of Example 1 of the present invention (Compound 1), a 10 −5 mol/L toluene solution was prepared. When this toluene solution was irradiated with ultraviolet light at 300 K while passing nitrogen through it, fluorescence having a peak wavelength of 392 nm was observed.
実施例7において、本発明実施例1の化合物(化合物1)に代えて本発明実施例2の化合物(化合物2)の10−5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が373nmの蛍光を観測した。 In Example 7, a 10 −5 mol/L toluene solution of the compound of Example 2 of the present invention (Compound 2) was prepared in place of the compound of Example 1 of the present invention (Compound 1), and the characteristics were evaluated by the same operation. I went. As a result, fluorescence with a peak wavelength of 373 nm was observed.
実施例7において、本発明実施例1の化合物(化合物1)に代えて本発明実施例3の化合物(化合物4)の10−5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が371nmの蛍光を観測した。 In Example 7, a 10 −5 mol/L toluene solution of the compound of Example 3 of the present invention (Compound 4) was prepared in place of the compound of Example 1 of the present invention (Compound 1), and the characteristics were evaluated by the same operation. I went. As a result, fluorescence with a peak wavelength of 371 nm was observed.
実施例7において、本発明実施例1の化合物(化合物1)に代えて本発明実施例4の化合物(化合物5)の10−5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が369nmの蛍光を観測した。 In Example 7, a 10 −5 mol/L toluene solution of the compound of Example 4 of the present invention (Compound 5) was prepared in place of the compound of Example 1 of the present invention (Compound 1), and the characteristics were evaluated by the same operation. I went. As a result, fluorescence with a peak wavelength of 369 nm was observed.
有機EL素子は、図5に示すように、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔注入層3、正孔輸送層4、正孔輸送層5、発光層6、正孔阻止層7、電子輸送層8、電子注入層9、陰極(アルミニウム電極)10の順に蒸着して作製した。
具体的には、膜厚100nmのITOを成膜したガラス基板1を有機溶媒で洗浄した後に、UVオゾン処理にて表面を洗浄した。その後、このITO電極付きガラス基板を真空蒸着機内に取り付け0.001Pa以下まで減圧した。
続いて、透明陽極2を覆うように正孔注入層3として、NPDを蒸着速度2.0Å/secで膜厚30nmとなるように形成した。この正孔注入層3の上に、正孔輸送層4として、TCTAを蒸着速度2.0Å/secで膜厚20nmとなるように形成した。この正孔輸送層4の上に、正孔輸送層5として、本発明実施例2の化合物(化合物2)を蒸着速度2.0Å/secで膜厚15nmとなるように形成した。この正孔輸送層5の上に、発光層6として、本発明実施例2の化合物(化合物2)と下記に示す発光材料2−[4−[3−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]フェニル]−4,6−ジフェニル−1,3,5−トリアジン(化合物112)を、蒸着速度比が本発明実施例2の化合物(化合物2):発光材料(化合物112)=85:15となる蒸着速度で二元蒸着を行い、膜厚20nmとなるように形成した。この発光層6の上に、正孔阻止層7としてDPEPOとTPBiを、DPEPO:TPBi=1:1となる蒸着速度で二元蒸着を行い、膜厚10nmとなるように形成した。この正孔阻止層7の上に、電子輸送層8として、TPBiを蒸着速度2.0Å/secで膜厚30nmとなるように形成した。この電子輸送層8の上に、電子注入層9としてフッ化リチウムを蒸着速度0.1Å/secで膜厚0.7nmとなるように形成した。最後に、アルミニウムを膜厚100nmとなるように蒸着して陰極10を形成した。作製した有機EL素子について、大気中、常温で特性測定を行った。
As shown in FIG. 5, the organic EL device has a hole injecting layer 3, a hole transporting layer 4, a hole transporting layer 5, and a light emitting layer on which an ITO electrode is formed in advance as a transparent anode 2 on a glass substrate 1. The layer 6, the hole blocking layer 7, the electron transport layer 8, the electron injection layer 9, and the cathode (aluminum electrode) 10 were vapor-deposited in this order.
Specifically, after the glass substrate 1 on which ITO having a film thickness of 100 nm was formed was washed with an organic solvent, the surface was washed with UV ozone treatment. Then, the glass substrate with the ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
Subsequently, NPD was formed as a hole injection layer 3 so as to cover the transparent anode 2 at a vapor deposition rate of 2.0 Å/sec so as to have a film thickness of 30 nm. On this hole injection layer 3, TCTA was formed as the hole transport layer 4 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 20 nm. On this hole transport layer 4, the compound (Compound 2) of Example 2 of the present invention was formed as the hole transport layer 5 at a vapor deposition rate of 2.0 Å/sec so that the film thickness was 15 nm. On this hole transporting layer 5, as a light emitting layer 6, the compound of Example 2 of the present invention (Compound 2) and the following light emitting material 2-[4-[3-(N-phenyl-9H-carbazole-3. -Yl)-9H-carbazol-9-yl]phenyl]-4,6-diphenyl-1,3,5-triazine (compound 112) with a deposition rate ratio of the compound of Example 2 of the present invention (compound 2): Binary vapor deposition was performed at a vapor deposition rate such that the light emitting material (compound 112)=85:15 to form a film having a thickness of 20 nm. On this light emitting layer 6, DPEPO and TPBi were formed as the hole blocking layer 7 by binary vapor deposition at a vapor deposition rate of DPEPO:TPBi=1:1 to form a film thickness of 10 nm. On this hole blocking layer 7, TPBi was formed as an electron transport layer 8 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 30 nm. Lithium fluoride was formed as an electron injection layer 9 on the electron transport layer 8 at a vapor deposition rate of 0.1 L/sec to a film thickness of 0.7 nm. Finally, aluminum was vapor-deposited to a film thickness of 100 nm to form the cathode 10. The characteristics of the produced organic EL device were measured at room temperature in the air.
有機EL素子は、図5に示すように、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔注入層3、正孔輸送層4、正孔輸送層5、発光層6、正孔阻止層7、電子輸送層8、電子注入層9、陰極(アルミニウム電極)10の順に蒸着して作製した。
具体的には、膜厚100nmのITOを成膜したガラス基板1を有機溶媒で洗浄した後に、UVオゾン処理にて表面を洗浄した。その後、このITO電極付きガラス基板を真空蒸着機内に取り付け0.001Pa以下まで減圧した。
続いて、透明陽極2を覆うように正孔注入層3として、NPDを蒸着速度2.0Å/secで膜厚30nmとなるように形成した。この正孔注入層3の上に、正孔輸送層4として、TCTAを蒸着速度2.0Å/secで膜厚20nmとなるように形成した。この正孔輸送層4の上に、正孔輸送層5として、本発明実施例3の化合物(化合物4)を蒸着速度2.0Å/secで膜厚15nmとなるように形成した。この正孔輸送層5の上に、発光層6として、本発明実施例3の化合物(化合物4)と発光材料(化合物112)を、蒸着速度比が本発明実施例3の化合物(化合物4):発光材料(化合物112)=85:15となる蒸着速度で二元蒸着を行い、膜厚20nmとなるように形成した。この発光層6の上に、正孔阻止層7としてDPEPOとTPBiを、DPEPO:TPBi=1:1となる蒸着速度で二元蒸着を行い、膜厚10nmとなるように形成した。この正孔阻止層7の上に、電子輸送層8として、TPBiを蒸着速度2.0Å/secで膜厚30nmとなるように形成した。この電子輸送層8の上に、電子注入層9としてフッ化リチウムを蒸着速度0.1Å/secで膜厚0.7nmとなるように形成した。最後に、アルミニウムを膜厚100nmとなるように蒸着して陰極10を形成した。作製した有機EL素子について、大気中、常温で特性測定を行った。
As shown in FIG. 5, the organic EL device has a hole injecting layer 3, a hole transporting layer 4, a hole transporting layer 5, and a light emitting layer on which an ITO electrode is formed in advance as a transparent anode 2 on a glass substrate 1. The layer 6, the hole blocking layer 7, the electron transport layer 8, the electron injection layer 9, and the cathode (aluminum electrode) 10 were vapor-deposited in this order.
Specifically, after the glass substrate 1 on which ITO having a film thickness of 100 nm was formed was washed with an organic solvent, the surface was washed with UV ozone treatment. Then, the glass substrate with the ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
Subsequently, NPD was formed as a hole injection layer 3 so as to cover the transparent anode 2 at a vapor deposition rate of 2.0 Å/sec so as to have a film thickness of 30 nm. On this hole injection layer 3, TCTA was formed as the hole transport layer 4 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 20 nm. On this hole transporting layer 4, the compound (Compound 4) of Example 3 of the present invention was formed as the hole transporting layer 5 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 15 nm. On this hole transport layer 5, the compound (Compound 4) of Example 3 of the present invention and the light emitting material (Compound 112) were formed as the light emitting layer 6, and the compound (Compound 4) of Example 3 of the present invention was deposited at a deposition rate ratio. : Light-emitting material (compound 112)=85:15 Two-dimensional vapor deposition was performed at a vapor deposition rate to form a film having a thickness of 20 nm. On this light emitting layer 6, DPEPO and TPBi were formed as the hole blocking layer 7 by binary vapor deposition at a vapor deposition rate of DPEPO:TPBi=1:1 to form a film thickness of 10 nm. On this hole blocking layer 7, TPBi was formed as an electron transport layer 8 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 30 nm. Lithium fluoride was formed as an electron injection layer 9 on the electron transport layer 8 at a vapor deposition rate of 0.1 L/sec to a film thickness of 0.7 nm. Finally, aluminum was vapor-deposited to a film thickness of 100 nm to form the cathode 10. The characteristics of the produced organic EL device were measured at room temperature in the air.
有機EL素子は、図5に示すように、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔注入層3、正孔輸送層4、正孔輸送層5、発光層6、正孔阻止層7、電子輸送層8、電子注入層9、陰極(アルミニウム電極)10の順に蒸着して作製した。
具体的には、膜厚100nmのITOを成膜したガラス基板1を有機溶媒で洗浄した後に、UVオゾン処理にて表面を洗浄した。その後、このITO電極付きガラス基板を真空蒸着機内に取り付け0.001Pa以下まで減圧した。
続いて、透明陽極2を覆うように正孔注入層3として、NPDを蒸着速度2.0Å/secで膜厚30nmとなるように形成した。この正孔注入層3の上に、正孔輸送層4として、TCTAを蒸着速度2.0Å/secで膜厚20nmとなるように形成した。この正孔輸送層4の上に、正孔輸送層5として、本発明実施例4の化合物(化合物5)を蒸着速度2.0Å/secで膜厚15nmとなるように形成した。この正孔輸送層5の上に、発光層6として、本発明実施例4の化合物(化合物5)と発光材料(化合物112)を、蒸着速度比が本発明実施例4の化合物(化合物5):発光材料(化合物112)=85:15となる蒸着速度で二元蒸着を行い、膜厚20nmとなるように形成した。この発光層6の上に、正孔阻止層7としてDPEPOとTPBiを、DPEPO:TPBi=1:1となる蒸着速度で二元蒸着を行い、膜厚10nmとなるように形成した。この正孔阻止層7の上に、電子輸送層8として、TPBiを蒸着速度2.0Å/secで膜厚30nmとなるように形成した。この電子輸送層8の上に、電子注入層9としてフッ化リチウムを蒸着速度0.1Å/secで膜厚0.7nmとなるように形成した。最後に、アルミニウムを膜厚100nmとなるように蒸着して陰極10を形成した。作製した有機EL素子について、大気中、常温で特性測定を行った。
As shown in FIG. 5, the organic EL device has a hole injecting layer 3, a hole transporting layer 4, a hole transporting layer 5, and a light emitting layer on which an ITO electrode is formed in advance as a transparent anode 2 on a glass substrate 1. The layer 6, the hole blocking layer 7, the electron transport layer 8, the electron injection layer 9, and the cathode (aluminum electrode) 10 were vapor-deposited in this order.
Specifically, after the glass substrate 1 on which ITO having a film thickness of 100 nm was formed was washed with an organic solvent, the surface was washed with UV ozone treatment. Then, the glass substrate with the ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
Subsequently, NPD was formed as a hole injection layer 3 so as to cover the transparent anode 2 at a vapor deposition rate of 2.0 Å/sec so as to have a film thickness of 30 nm. On this hole injection layer 3, TCTA was formed as the hole transport layer 4 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 20 nm. On this hole transporting layer 4, the compound (Compound 5) of Example 4 of the present invention was formed as the hole transporting layer 5 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 15 nm. On this hole transport layer 5, the compound (Compound 5) of Example 4 of the present invention and the light emitting material (Compound 112) were used as the light emitting layer 6, and the compound (Compound 5) of Example 4 of the present invention was deposited at a deposition rate ratio. : Light-emitting material (compound 112)=85:15 Two-dimensional vapor deposition was performed at a vapor deposition rate to form a film having a thickness of 20 nm. On this light emitting layer 6, DPEPO and TPBi were formed as the hole blocking layer 7 by binary vapor deposition at a vapor deposition rate of DPEPO:TPBi=1:1 to form a film thickness of 10 nm. On this hole blocking layer 7, TPBi was formed as an electron transport layer 8 at a vapor deposition rate of 2.0 Å/sec to a film thickness of 30 nm. Lithium fluoride was formed as an electron injection layer 9 on the electron transport layer 8 at a vapor deposition rate of 0.1 L/sec to a film thickness of 0.7 nm. Finally, aluminum was vapor-deposited to a film thickness of 100 nm to form the cathode 10. The characteristics of the produced organic EL device were measured at room temperature in the air.
本発明の実施例2の化合物(化合物2)、実施例3の化合物(化合物4)、実施例4の化合物(化合物5)を使用して作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。 Light emission when a DC voltage is applied to an organic EL device produced using the compound of Example 2 (Compound 2) of the present invention, the compound of Example 3 (Compound 4), and the compound of Example 4 (Compound 5) The measurement results of the properties are summarized in Table 1.
[比較例1]
比較のために、実施例11〜13における正孔輸送層5、及び発光層6の材料を、実施例3の化合物(化合物4)からmCBPに代え、実施例11〜13と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行った。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
[Comparative Example 1]
For comparison, the materials of the hole transport layer 5 and the light emitting layer 6 in Examples 11 to 13 were changed from the compound of Example 3 (compound 4) to mCBP, and organic compounds were formed under the same conditions as those of Examples 11 to 13. An EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 shows the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL device.
表1に示すように、電流密度10mA/cm2の電流を流したときの電圧は、mCBPを用いた比較例1の7.8Vに対して、実施例11では7.8V、実施例12では6.8V、実施例13では7.0Vとほぼ同等、もしくは低下した値を示した。輝度についても、mCBPを用いた比較例1の1116cd/m2に対して、実施例11では1107cd/m2、実施例12では1550cd/m2、実施例13では1237cd/m2とほぼ同等、もしくは大きく向上した値を示した。また、発光効率についてもmCBPを用いた比較例1の11.3cd/Aに対して、実施例11では11.8cd/m2、実施例12では14.7cd/m2、実施例13では13.6cd/m2とほぼ同等、もしくは大きく向上した値を示した。さらに電力効率についてもmCBPを用いた比較例1の4.56lm/Wに対して、実施例11では4.64lm/W、実施例12では6.79lm/W、実施例13では6.12lm/Wとほぼ同等、もしくは大きく向上した値を示した。 As shown in Table 1, the voltage when a current having a current density of 10 mA/cm 2 was passed was 7.8 V in Example 11 and 7.8 V in Comparative Example 1 using mCBP. 6.8V, Example 13 showed a value almost equal to or lower than 7.0V. Regarding the brightness, in comparison with 1116 cd/m 2 of Comparative Example 1 using mCBP, in Example 11, 1107 cd/m 2 , in Example 12 1550 cd/m 2 , and in Example 13, 1237 cd/m 2 , almost the same, Or, it showed a greatly improved value. Further, with respect to 11.3cd / A of Comparative Example 1 using mCBP also emission efficiency, Example 11, 11.8cd / m 2, Example 12, 14.7cd / m 2, in Examples 13 13 The value was almost equal to or significantly improved to 0.6 cd/m 2 . Further, as for the power efficiency, 4.56 lm/W of Comparative Example 1 using mCBP was compared with 4.64 lm/W in Example 11, 6.79 lm/W in Example 12, and 6.12 lm/W in Example 13. The value was almost the same as or significantly improved.
以上のように、本発明の化合物を用いた有機EL素子は、mCBPを用いた素子と比較して、駆動電圧の大幅な低下や発光効率の大幅な向上を達成できることが分かった。 As described above, it was found that the organic EL device using the compound of the present invention can achieve a significant reduction in driving voltage and a significant improvement in luminous efficiency, as compared with a device using mCBP.
本発明のアザカルバゾールを有する化合物は、薄膜安定性が良好で、発光層の材料、特に発光層のホスト材料として優れている。また、該化合物を用いて有機EL素子を作製することにより、従来の有機EL素子の輝度と発光効率を格段に改良することができる。 The compound having azacarbazole of the present invention has good thin film stability and is excellent as a material for a light emitting layer, particularly as a host material for a light emitting layer. In addition, by manufacturing an organic EL device using the compound, the brightness and the luminous efficiency of the conventional organic EL device can be significantly improved.
Claims (7)
(式中、A、B、C、D、E、F、G、Hは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Y、Zは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) In an organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched between the electrodes, the organic layer is a light emitting layer, and a compound having an azacarbazole structure represented by the following general formula (1): An organic electroluminescence device, which is used as a constituent material of the light emitting layer.
(In the formula, at least one of A, B, C, D, E, F, G and H is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X, Y and Z are the same or different from each other. Also, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or Represents a di-substituted amino group substituted by a group selected from condensed polycyclic aromatic groups, L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted It represents a substituted fused polycyclic aromatic divalent group.If L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and may be a hydrogen atom or a heavy atom. A hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent Optionally substituted cycloalkyl group having 5 to 10 carbon atoms, optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms, optionally substituted Good straight-chain or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group , A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group (A di-substituted amino group substituted with a group selected from the group groups, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
(式中、A、B、C、D、E、F、G、Hは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Y、Zは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) A compound having an azacarbazole skeleton represented by the following general formula (1-1).
(In the formula, at least one of A, B, C, D, E, F, G and H is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X, Y and Z are the same or different from each other. Also, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or Represents a di-substituted amino group substituted by a group selected from condensed polycyclic aromatic groups, L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted It represents a substituted fused polycyclic aromatic divalent group.If L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and may be a hydrogen atom or a heavy atom. A hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent Optionally substituted cycloalkyl group having 5 to 10 carbon atoms, optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms, optionally substituted Good straight-chain or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group , A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group (A di-substituted amino group substituted with a group selected from the group groups, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Y、Zは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) A compound having an azacarbazole skeleton represented by the following general formula (1-2).
(In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X, Y and Z may be the same or different from each other, and may be substituted or unsubstituted. Aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by a group, L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic group. Represents a divalent group.If L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom. , A cyano group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a carbon atom which may have a substituent A cycloalkyl group having 5 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and an alkyl group having 1 to 6 carbon atoms which may have a substituent. Linear or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic Substituted with a group selected from a heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group. A substituted disubstituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) A compound having an azacarbazole skeleton represented by the following general formula (1-3).
(In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R10は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) A compound having an azacarbazole skeleton represented by the following general formula (1-4).
(In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 10 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R7は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) A compound having an azacarbazole skeleton represented by the following general formula (1-5).
(In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 7 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
(式中、A、B、C、Dは、少なくとも1つが窒素原子であって、炭素原子または窒素原子を表し、X、Yは相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Lは単結合、置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環、または置換もしくは無置換の縮合多環芳香族の2価基を表す。Lが単結合であるならば、添え字nは0である。R1〜R7は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) A compound having an azacarbazole skeleton represented by the following general formula (1-6).
(In the formula, at least one of A, B, C and D is a nitrogen atom and represents a carbon atom or a nitrogen atom, and X and Y may be the same or different from each other, and may be a substituted or unsubstituted aromatic group. Hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted condensed polycyclic aromatic group, or group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group Represents a di-substituted amino group substituted by L. L is a single bond, a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycyclic aromatic divalent When L is a single bond, the subscript n is 0. R 1 to R 7 may be the same or different from each other, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano. A group, a trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having 5 carbon atoms which may have a substituent 10 cycloalkyl groups, optionally substituted C 2 -C 6 linear or branched alkenyl groups, optionally substituted C 1 -C 6 linear chains Or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.)
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