CN116529244A - Novel organic compound and organic light-emitting element comprising same - Google Patents
Novel organic compound and organic light-emitting element comprising same Download PDFInfo
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- CN116529244A CN116529244A CN202180078170.XA CN202180078170A CN116529244A CN 116529244 A CN116529244 A CN 116529244A CN 202180078170 A CN202180078170 A CN 202180078170A CN 116529244 A CN116529244 A CN 116529244A
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- 150000002894 organic compounds Chemical class 0.000 title claims description 15
- 239000000126 substance Substances 0.000 claims abstract description 177
- 125000004432 carbon atom Chemical group C* 0.000 claims description 357
- 239000010410 layer Substances 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 49
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 40
- 229910052805 deuterium Inorganic materials 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 239000002019 doping agent Substances 0.000 claims description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 17
- 125000005104 aryl silyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
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- 125000003367 polycyclic group Chemical group 0.000 claims description 13
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- 238000000034 method Methods 0.000 claims description 12
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- 238000006467 substitution reaction Methods 0.000 claims description 11
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- 229910052760 oxygen Inorganic materials 0.000 claims description 9
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- 125000004429 atom Chemical group 0.000 claims description 8
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- 125000004986 diarylamino group Chemical group 0.000 claims description 8
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
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- 150000001721 carbon Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 238000005137 deposition process Methods 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 description 92
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- 239000000463 material Substances 0.000 description 33
- 238000006757 chemical reactions by type Methods 0.000 description 28
- -1 and Chemical group 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 10
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 125000003277 amino group Chemical group 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000005581 pyrene group Chemical group 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- XSORPSLNKUANCM-UHFFFAOYSA-N OC1=CC=CC2=C1C(C=CC=C1Br)=C1O2 Chemical compound OC1=CC=CC2=C1C(C=CC=C1Br)=C1O2 XSORPSLNKUANCM-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- YOZHUJDVYMRYDM-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-naphthalen-1-yl-n-phenylaniline Chemical compound C=1C=C(C=2C(=CC(NC=3C=CC=CC=3)=CC=2)C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=C1 YOZHUJDVYMRYDM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001337 aliphatic alkines Chemical class 0.000 description 2
- 125000006193 alkinyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003220 pyrenes Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
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- XOVMDVZAWWQSDC-UHFFFAOYSA-N (2-fluoro-6-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(F)=C1B(O)O XOVMDVZAWWQSDC-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 1
- HXTPPPWXNHSMLZ-UHFFFAOYSA-N 1,7-dibromodibenzofuran Chemical compound C1=CC(Br)=C2C3=CC=C(Br)C=C3OC2=C1 HXTPPPWXNHSMLZ-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
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- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- LUNBVFSLWVMETO-UHFFFAOYSA-N 2-N-(2-naphthalen-2-ylphenyl)-1-N,1-N,2-N-triphenylbenzene-1,2-diamine Chemical compound C1=C(C=CC2=CC=CC=C12)C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 LUNBVFSLWVMETO-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- YACSIMLPPDISOJ-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-(3-methylphenyl)-n-phenylaniline Chemical compound CC1=CC=CC(C=2C(=CC=C(NC=3C=CC=CC=3)C=2)C=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 YACSIMLPPDISOJ-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- XHHROUIPPVCTAR-UHFFFAOYSA-N 6-bromodibenzofuran-2-ol Chemical compound Oc1ccc2oc3c(Br)cccc3c2c1 XHHROUIPPVCTAR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000005075 adamantyloxy group Chemical group C12(CC3CC(CC(C1)C3)C2)O* 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 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 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229930184652 p-Terphenyl Chemical group 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to a novel heterocyclic compound which can be used for an organic light-emitting device, and an organic light-emitting device comprising the same, wherein the [ chemical formula A ] and the [ chemical formula B ] are the same as those described in the detailed description of the present invention.
Description
Technical Field
The present invention relates to a novel organic compound which can be used for an organic light-emitting element, and more particularly, to a novel heterocyclic compound which can be used as a host material for a light-emitting layer in an organic light-emitting element and can realize element characteristics of high light-emitting efficiency, low-voltage driving, and long life by the compound, and an organic light-emitting element including the heterocyclic compound.
Background
An organic light emitting element (OLED: organic light emitting diode) is a display utilizing a self-luminescence phenomenon, and is expected to be applied as a full-color display or illumination because it has a wide viewing angle, can be made thinner and smaller than a liquid crystal display, and has advantages such as a fast response speed.
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer therebetween. Here, in most cases, in order to improve efficiency and stability of the organic light-emitting element, the organic layer is constituted of a multilayer structure composed of substances different from each other, and for example, may be constituted of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In the structure of such an organic light emitting element, if a voltage is applied between two electrodes, holes are injected from an anode to an organic layer, electrons are injected from a cathode to the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons re-transition to a ground state. Such an organic light emitting element is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, high-speed responsiveness, and the like.
Materials used as an organic layer in an organic light-emitting element can be classified into a light-emitting material and a charge-transporting material (e.g., a hole-injecting material, a hole-transporting material, an electron-injecting material, etc.) according to functions. The light emitting materials may be classified into a polymer type and a low polymer type according to molecular weight, and may be classified into a fluorescent material from a singlet excited state of electrons and a phosphorescent material from a triplet excited state of electrons according to a light emitting mechanism.
In addition, in the case where only one kind of substance is used as a light emitting material, since the maximum emission wavelength is shifted to a long wavelength due to intermolecular interaction and the color purity is lowered or the element efficiency is lowered due to the effect of light emission reduction, a host-dopant system may be used as a light emitting material in order to increase the color purity and increase the light emitting efficiency by energy transfer.
The principle is that if a small amount of dopant smaller than the band gap of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated from the light emitting layer are transferred to the dopant to emit light with high efficiency. In this case, the wavelength of the host shifts to the wavelength band of the dopant, and thus light having a desired wavelength can be obtained according to the type of dopant used.
Recently, studies on heterocyclic compounds as a host compound in such a light-emitting layer have been conducted, and as related art, a compound having a dibenzofuran ring structure incorporated in an anthracene ring and an organic light-emitting element including the compound are described in korean patent publication No. 10-2016-0089693 (2016.07.28), and a compound having an aryl substituent or a heteroaryl substituent incorporated in a condensed fluorene ring including a heteroatom such as oxygen, nitrogen, sulfur, and the like and an organic light-emitting element including the compound are disclosed in korean patent publication No. 10-2017-0055743 (2017.05.22).
However, although various forms of compounds including the prior art are manufactured for the light emitting layer of the organic light emitting element, there has been a continued demand for development of a novel compound which can be applied to the organic light emitting element and has element characteristics of high efficiency, low voltage driving and long life, and an organic light emitting element including the compound.
Disclosure of Invention
Technical problem
Accordingly, a first technical problem to be solved by the present invention is to provide a novel organic compound which can be used as a host material for a light-emitting layer in an organic light-emitting element.
Further, a second technical problem to be solved by the present invention is to apply the organic compound to a host substance in an organic light emitting element, thereby providing an organic light emitting element (OLED: organic light emitting diode) with high efficiency, low voltage driving and long life.
Technical proposal
In order to achieve the above object, the present invention provides an organic compound represented by the following [ chemical formula a ] or [ chemical formula B ].
In the [ chemical formula A ] and the [ chemical formula B ],
the R is 1 To R 14 And are each the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group;
The linker L 1 L and L 2 Are each the same or different from each other and are each independently one selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms;
the n1 and n2 are each the same or different and are each independently an integer from 0 to 2, each linker L in the case where n1 and n2 are each 2 1 L and L 2 Are the same as or different from each other,
the R and R' are the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group;
Wherein n3 and n4 are the same or different, and each is an integer of 1 to 9, and each R and R' is the same or different when n3 and n4 are 2 or more,
in the [ chemical formula a ] and the [ chemical formula B ], the "substitution" in the "substituted or unsubstituted" means substitution with one or more substituents selected from the group consisting of: deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, haloalkyl having 1 to 24 carbon atoms, alkenyl having 1 to 24 carbon atoms, alkynyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, heteroalkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, aralkyl having 7 to 24 carbon atoms, alkylaryl having 7 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, heteroaralkyl having 2 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, alkylamino having 1 to 24 carbon atoms, diarylamino having 12 to 24 carbon atoms, diheteroarylamino having 2 to 24 carbon atoms, aryl (heteroaryl) amino having 7 to 24 carbon atoms, alkylsilyl having 1 to 24 carbon atoms, arylsilyl having 6 to 24 carbon atoms, aryloxy having 6 to 24 carbon atoms, and arylene having 6 to 24 carbon atoms.
Technical effects
In the case where the novel organic compound represented by the [ chemical formula a ] or the [ chemical formula B ] according to the present invention is used as a host substance in an organic light emitting element, an organic light emitting element exhibiting higher efficiency, low voltage driving, and long life as compared with an organic light emitting element according to the related art can be provided.
Drawings
Fig. 1 is a schematic view of an organic light emitting element according to an embodiment of the present invention.
Detailed Description
Hereinafter, the present invention will be described in more detail. In the drawings of the present invention, the size or dimension of the structure is shown enlarged or reduced from that of the actual structure for clarity of the present invention, and well-known structures are omitted for highlighting the characteristic structures, and therefore the present invention is not limited to the drawings.
The size and thickness of each of the components shown in the drawings are arbitrarily shown for convenience of explanation, and the present invention is not limited to the content shown in the drawings, but the thicknesses are shown enlarged for clearly showing a plurality of layers and regions in the drawings. In the drawings, the thicknesses of partial layers and regions are exaggerated for convenience of description. When a layer, film, region, plate, or the like is referred to as being "on" another portion, it includes not only the case of being "immediately above" the other portion but also the case of having another portion in the middle.
In the present specification, when a certain component is referred to as "including" a certain component, unless otherwise stated, other components are not excluded, but other components may be included. In the present specification, "on …" means above or below the target portion, and does not necessarily mean above the gravitational direction.
The present invention provides an organic compound represented by the following [ chemical formula A ] or [ chemical formula B ].
In the [ chemical formula A ] and the [ chemical formula B ],
the R is 1 To R 14 Are each the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl groupAny one of a substituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group;
The linker L 1 L and L 2 Are each the same or different from each other and are each independently one selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms;
the n1 and n2 are each the same or different and are each independently an integer from 0 to 2, each linker L in the case where n1 and n2 are each 2 1 L and L 2 Are the same as or different from each other,
the R and R' are the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group;
Wherein n3 and n4 are the same or different, and each is an integer of 1 to 9, and each R and R' is the same or different when n3 and n4 are 2 or more,
in the [ chemical formula a ] and the [ chemical formula B ], the "substitution" in the "substituted or unsubstituted" means substitution with one or more substituents selected from the group consisting of: deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, haloalkyl having 1 to 24 carbon atoms, alkenyl having 1 to 24 carbon atoms, alkynyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, heteroalkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, aralkyl having 7 to 24 carbon atoms, alkylaryl having 7 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, heteroaralkyl having 2 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, alkylamino having 1 to 24 carbon atoms, diarylamino having 12 to 24 carbon atoms, diheteroarylamino having 2 to 24 carbon atoms, aryl (heteroaryl) amino having 7 to 24 carbon atoms, alkylsilyl having 1 to 24 carbon atoms, arylsilyl having 6 to 24 carbon atoms, aryloxy having 6 to 24 carbon atoms, and arylene having 6 to 24 carbon atoms.
In the present invention, when considered in terms of the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms", etc., the range of the carbon atoms of the alkyl group having 1 to 30 carbon atoms and the carbon atoms of the aryl group having 5 to 50 carbon atoms respectively represents the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when considered as unsubstituted irrespective of the substituted moiety. For example, a phenyl group substituted with a butyl group at the para-position is considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.
The aryl group as a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and when a substituent is present in the aryl group, substituents adjacent to each other can be condensed (fused) with each other to additionally form a ring.
Specific examples of the aryl group include phenyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, perylenyl, and, Aromatic groups such as a radical, a tetracenyl radical and a fluoranthenyl radical, and one or more hydrogen atoms in the aryl radical may be replaced by a heavy hydrogen atomSon, halogen atom, hydroxy, nitro, cyano, silyl, amino (-NH) 2 -NH (R), -N (R ') (R "), R' and R" are, independently of each other, alkyl groups of 1 to 10 carbon atoms, referred to as "alkylamino", amidino, hydrazino, hydrazone, carboxyl, sulfonic acid, phosphoric acid, alkyl groups of 1 to 24 carbon atoms, haloalkyl groups of 1 to 24 carbon atoms, alkenyl groups of 2 to 24 carbon atoms, alkynyl groups of 2 to 24 carbon atoms, heteroalkyl groups of 1 to 24 carbon atoms, aryl groups of 6 to 24 carbon atoms, aralkyl groups of 6 to 24 carbon atoms, heteroaryl groups of 2 to 24 carbon atoms or heteroaralkyl groups of 2 to 24 carbon atoms.
Heteroaryl as used in the compounds of the present invention as substituents means a cyclic aromatic system of 2 to 24 carbon atoms including one, two or three heteroatoms selected from N, O, P, si, S, ge, se, te and the other ring atoms being carbon, said rings being fused to form a ring. In addition, more than one hydrogen atom in the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.
In the present invention, the aromatic heterocyclic ring means that one or more of the aromatic carbons in the aromatic hydrocarbon ring is substituted with a heteroatom, and preferably 1 to 3 aromatic carbons in the aromatic hydrocarbon in the aromatic heterocyclic ring may be substituted with one or more heteroatoms selected from N, O, P, si, S, ge, se, te.
The alkyl group as a substituent used in the present invention is a substituent from which one hydrogen atom in an alkane (alkine) is removed, and includes a straight-chain or branched structure, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl and the like, and one or more hydrogen atoms in the alkyl group may be substituted with the same substituent as in the case of the aryl group.
The "ring" in the cycloalkyl group as a substituent used in the compound of the present invention means a substituent capable of forming a monocyclic or polycyclic structure of an alkyl group-internal saturated hydrocarbon, and specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadiene, decalinyl, norbornyl, bornyl, isobornyl and the like, and one or more hydrogen atoms in the cycloalkyl group may be substituted with the same substituent as in the case of the aryl group.
The alkoxy group as a substituent used in the compound of the present invention is a substituent having an oxygen atom bonded to the end of an alkyl group or a cycloalkyl group, and specific examples thereof include methoxy group, ethoxy group, propoxy group, isobutoxy group, sec-butoxy group, pentyloxy group, isopentyloxy group, hexyloxy group, cyclobutoxy group, cyclopentyloxy group, adamantyloxy group, dicyclopentadienyloxy group, bornyloxy group, isobornyloxy group and the like, and one or more hydrogen atoms in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.
Specific examples of the aralkyl group as a substituent used in the compound of the present invention include benzyl (benzyl), phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and the like, and one or more hydrogen atoms in the aralkyl group may be substituted with the same substituent as in the case of the aryl group.
Specific examples of the silyl group as a substituent used in the compound of the present invention include a trimethylsilyl group, a triethylsilyl group, a triphenylsilyl group, a trimethoxysilyl group, a dimethoxyphenylsilyl group, a diphenylmethylsilyl group, a distyrylsilyl group, a methylcyclobutylsilyl group, a dimethylfuranylsilyl group, and the like, and one or more hydrogen atoms in the silyl group may be substituted with the same substituent as in the case of the aryl group.
In the present invention, an alkene (alkinyl) group represents an alkyl substituent comprising one carbon-carbon double bond composed of two carbon atoms, and an alkyne (alkinyl) group represents an alkynyl substituent comprising one carbon-carbon triple bond composed of two carbon atoms.
Further, as the alkylene (alkylene) group used in the present invention, as an organic radical derived by removing two hydrogens in a molecule of an alkane (alkine) of a saturated hydrocarbon in a straight-chain or branched-chain form, there may be mentioned, for example, methylene, ethylene, propylene, isopropylene, isobutylene, sec-butylene, tert-butylene, pentylene, isopentylene, hexylene and the like, and one or more hydrogen atoms in the alkylene group may be substituted with the same substituent as in the case of the aryl group.
In the present invention, the diarylamino group represents an amine group in which the two identical or different aryl groups are bonded to a nitrogen atom, and in the present invention, the diheteroarylamino group represents an amine group in which the two identical or different heteroaryl groups are bonded to a nitrogen atom, and the aromatic (heteroaromatic) amino group represents an amine group in which the aryl group and the heteroaryl group are bonded to a nitrogen atom, respectively.
In addition, "substitution" in the "substituted or unsubstituted" in the [ chemical formula a ] and the [ chemical formula B ] may be substituted with one or more substituents selected from the group consisting of: a heavy hydrogen, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an haloalkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroaralkyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 12 to 18 carbon atoms, a diheteroarylamino group having 2 to 18 carbon atoms, an aryl (hetero) amino group having 7 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylene group having 6 to 18 carbon atoms, and a sulfinyl group having 6 to 18 carbon atoms.
In the present invention, the compound represented by the formula [ formula A ]]The organic compound is characterized in that a linker L is bonded to a specific position (see the following structural formula C) in a substituted or unsubstituted pyrene ring 1 At the linker L 1 Position 1 to which a substituted or unsubstituted dibenzofuranyl group is bonded, and is represented by the [ formula B ]]The organic compound is characterized in that,the linker L is bonded to a specific position (see the following structural formula C) in the substituted or unsubstituted pyrene ring 2 At the linker L 2 Position 2 to which a substituted or unsubstituted dibenzofuranyl group is bonded.
[ Structure C ]
With a linker L 1 Or LL2 2 Binding bond sites of binding
In the [ chemical formula a ] and the [ chemical formula B ] according to the present invention, the compound represented by the [ chemical formula a ] may include at least one or more deuterium, and the compound represented by the [ chemical formula B ] may include at least one or more deuterium.
In more detail, the [ formula A ]]R in (a) 1 To R 7 At least one of which may be a substituent comprising deuterium, said [ formula B ]]R in (a) 8 To R 14 At least one of which may be a substituent comprising deuterium.
Also, in the present invention, in the case where the compound represented by the [ chemical formula a ] may include at least one or more deuterium and the compound represented by the [ chemical formula B ] may include at least one or more deuterium, at least one R in the [ chemical formula a ] may be a substituent including deuterium, and at least one R' in the [ chemical formula B ] may be a substituent including deuterium.
And, as an embodiment according to the present invention, the R 1 To R 14 R, R' may be the same or different, respectively, and are each, independently of each other, a substituent selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and a halogen group.
And, as an embodiment according to the present invention,said [ formula A ]]R in (a) 1 To R 7 At least one of which may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, said [ formula B ]]R in (a) 8 To R 14 May be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
And, as an embodiment according to the present invention, the [ formula a ]]Said [ formula B ]]The linker L in (2) 1 L and L 2 May be a single bond, or may be a member selected from the group consisting of the following structural formula 1]To [ Structure 5]]Any one of the following.
The carbon position of the aromatic ring in the [ structural formula 1] to [ structural formula 5] may be bonded with hydrogen or deuterium.
And, as an embodiment according to the present invention, the linking group L 1 L and L 2 May be single bonds, respectively.
Also, as an embodiment of the present invention, n3 and n4 in the [ chemical formula a ] and the [ chemical formula B ] may be 1, respectively.
Also, as an embodiment according to the present invention, at least one R in the [ chemical formula a ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, at least one R 'in the [ chemical formula B ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in this case, preferably, the n3 and the n4 in the [ chemical formula a ] and the [ chemical formula B ] may be 1, respectively, R in the [ chemical formula a ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and R' in the [ chemical formula B ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
Also, as an embodiment according to the present invention, the organic compound represented by the [ chemical formula a ] or the [ chemical formula B ] may be a compound represented by any one of the following [ chemical formula a-1] or the [ chemical formula B-1 ].
At this time, in the [ chemical formula A-1] ]Said [ formula B-1 ]]In the above formula, the substituent R 1 To R 14 Linker L 1 L and L 2 N1 and n2 and are as defined in formula A]Or [ formula B ]]The content defined in (a) is the same,
the substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.
And, as an embodiment according to the present invention, the [ formula a ]]Said [ formula B ]]The n3 and n4 in (a) may be 1, respectively, the [ formula A ]]R in (a) 1 To R 7 At least one of R may be an aryl group having 6 to 18 carbon atoms substituted with deuterium, said [ formula B ]]R in (a) 8 To R 14 At least one of R' may be an aryl group having 6 to 18 carbon atoms substituted with deuterium.
Also, as an embodiment according to the present invention, the n3 and the n4 in the [ chemical formula a ] and the [ chemical formula B ] may be 1, respectively, R in the [ chemical formula a ] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, and R' in the [ chemical formula B ] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
Also, the compound represented by the [ chemical formula a ] or [ chemical formula B ] according to the present invention may be any one compound selected from the [ chemical formula 1] to [ chemical formula 240 ].
Also, the present invention provides an organic light emitting element including: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes one or more compounds represented by the [ chemical formula a ] or the [ chemical formula B ] according to the present invention.
In addition, in the present invention, "(organic layer) containing one or more organic compounds" can be interpreted as "(organic layer) may contain one organic compound belonging to the scope of the present invention or two or more compounds different from each other belonging to the scope of the organic compounds.
At this time, the organic layer in the organic light emitting element of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.
As a further preferable embodiment of the present invention, in the present invention, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer may be formed using a host and a dopant, and at least one of the compounds represented by the [ chemical formula a ] or the [ chemical formula B ] in the present invention may be included as a host substance in the light emitting layer.
Also, in the present invention, as the dopant compound for the light emitting layer, at least one compound represented by any one of the following [ chemical formula D1] to [ chemical formula D10] may be included.
[ chemical formula D1]
[ chemical formula D2]
In said [ chemical formula D1]]Said [ formula D2]]In (A) 31 、A 32 、E 1 F (F) 1 Are each the same or different and are each, independently of one another, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
the A is 31 Two carbon atoms adjacent to each other in the aromatic ring of (A) and the A 32 Two carbon atoms adjacent to each other in the aromatic ring of (a) and attached to the substituent R 51 R is R 52 Forming five-membered rings from carbon atoms of (2) to form condensed rings, respectively;
the linker L 21 To L 32 And are each the same or different and are each independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
The W and W' are each the same or different from each other and are each independently selected from N-R 53 、CR 54 R 55 、SiR 56 R 57 、GeR 58 R 59 Either one of O, S, se;
the substituent R 51 To R 59 、Ar 21 To Ar 28 And are each the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
The R is 51 R is R 52 Can be linked to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, wherein the carbon atoms of the alicyclic, aromatic monocyclic or polycyclic ring can be replaced by one or more hetero atoms selected from N, O, P, si, S, ge, se, te;
the p11 to p14, r11 to r14 and s11 to s14 are integers of 1 to 3 respectively, and are 2 or more respectivelyIn the case of individual linkers L 21 To L 32 Respectively, are the same as or different from each other,
wherein x1 is 1, y1, z1 and z2 are each the same or different and are each independently an integer of 0 to 1,
the Ar is as follows 21 Ar and Ar 22 、Ar 23 Ar and Ar 24 、Ar 25 Ar and Ar 26 Ar, ar 27 Ar and Ar 28 May be respectively connected to each other to form a ring;
in said [ chemical formula D1 ]]In (A) 32 Two carbon atoms adjacent to each other within the ring and the structural formula Q 11 To form a condensed ring,
in said [ chemical formula D2 ]]In said A 31 Two carbon atoms adjacent to each other in the ring may be of the formula Q 12 To form a condensed ring, said A 32 Two carbon atoms adjacent to each other in the ring may be adjacent to the structural formula Q 11 And are combined to form a condensed ring.
[ chemical formula D3]
In the above-mentioned [ chemical formula D3],
the X is 1 Is any one selected from B, P, P =o,
the T1 to T3 are each the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
The Y is 1 Is selected from N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Any one of them;
the Y is 2 Is selected from N-R 66 、CR 66 R 68 、O、S、SiR 69 R 70 Any one of them;
the R is 61 To R 70 Are each identical or different from each other and are each independently selected from hydrogenA heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a halogen group, and R 61 To R 70 Can be combined with one or more rings selected from the group consisting of T1 to T3, respectively, to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.
In the [ chemical formula D4] and the [ chemical formula D5],
the X is 2 Is any one selected from B, P, P =o,
t4 to T6 are the same as T1 to T3 in [ formula D3],
the Y is 4 Is selected from N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Any one of them;
the Y is 5 Is selected from N-R 66 、CR 66 R 68 、O、S、SiR 69 R 70 Any one of them;
the Y is 6 Is selected from N-R 71 、CR 72 R 73 、O、S、SiR 74 R 75 Any one of them;
the R is 61 To R 75 And [ chemical formula D3]]Said R in (a) 61 To R 70 The same applies.
The X is 3 Is any one selected from B, P, P =o,
t7 to T9 are the same as T1 to T3 in [ formula D3],
the Y is 6 Is selected from N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Any one of them;
the substituent R 61 To R 65 、R 71 To R 72 Respectively with [ chemical formula D3]]Said R in (a) 61 To R 70 The same is true of the fact that,
the R is 71 And R is 72 May be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or may be combined with the T7 ring or T9 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, respectively.
[ chemical formula D10]
In the [ chemical formula D8] to the [ chemical formula D10],
wherein X is any one selected from B, P, P =O,
the Q is 1 To Q 3 Respectively with [ chemical formula D3]]In (2) are the same as T1 to T3,
the linker Y is selected from N-R 3 、CR 4 R 5 Either one of the two or more of O, S, se,
the substituent R 3 To R 5 Respectively with [ chemical formula D3 ]]Said R in (a) 61 To R 70 The same is true of the fact that,
the R is 3 To R 5 Can be separately with the Q 2 Ring or Q 3 The rings combine to additionally form a single or multiple ring that is alicyclic or aromatic,
the R is 4 And R is 5 May be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
for the ring formed by the Cy1, if the nitrogen (N) atom is removed, Q bonded to the nitrogen (N) atom 1 An aromatic carbon atom in the ring and Q to be bonded to said Cy1 1 The aromatic carbon atom in the ring is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
in the chemical formula D9 of the present invention,
the Cy2 is attached to the Cy1 to form a saturated hydrocarbon ring, and the ring formed by the Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms if the carbon atom included in the Cy1 is removed,
in the chemical formula D10 described above, the chemical formula,
for the ring formed by the Cy3, if Q to be bound to the Cy3 is removed 3 An aromatic carbon atom in the ring, an aromatic carbon atom in Q3 to be bonded to a nitrogen (N) atom, a carbon atom in Cy1 to which the nitrogen (N) atom is bonded, is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
Wherein "substitution" in the "substituted or unsubstituted" in the [ chemical formula D1] to [ chemical formula D10] means substitution with one or more substituents selected from the group consisting of: deuterium, cyano, halo, hydroxy, nitro, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, alkynyl of 2 to 24 carbon atoms, cycloalkyl of 3 to 24 carbon atoms, heteroalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, alkylaryl of 7 to 24 carbon atoms, heteroaryl of 2 to 24 carbon atoms, heteroaralkyl of 2 to 24 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkylamino of 1 to 24 carbon atoms, diarylamino of 12 to 24 carbon atoms, diheteroarylamino of 2 to 24 carbon atoms, aryl (heteroaryl) amino of 7 to 24 carbon atoms, alkylsilyl of 1 to 24 carbon atoms, arylsilyl of 6 to 24 carbon atoms, aryloxy of 6 to 24 carbon atoms, sulfinyl of 6 to 24 carbon atoms, and more preferably one of the following groups may be substituted as a preferred substituent: deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkynyl having 2 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, heteroalkyl having 1 to 12 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 20 carbon atoms, alkylaryl having 7 to 20 carbon atoms, heteroaryl having 2 to 18 carbon atoms, heteroaralkyl having 2 to 18 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkylamino having 1 to 12 carbon atoms, diarylamino having 12 to 18 carbon atoms, diheteroarylamino having 2 to 18 carbon atoms, aryl (heteroaryl) amino having 7 to 18 carbon atoms, alkylsilyl having 1 to 12 carbon atoms, arylsilyl having 6 to 18 carbon atoms, aryloxy having 6 to 18 carbon atoms, and arylsulfinyl having 6 to 18 carbon atoms.
And, for the dopant compound according to the present invention represented by the [ formula D3 ]]To [ chemical formula D10 ]]As the boron compound represented by any one of the above, T1 to T9 or Q may be substituted 1 To Q 3 The substituent of the aromatic hydrocarbon ring or the aromatic heterocyclic ring of (C) may be substituted with a heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, wherein the alkyl group or the aryl group of each of the alkylamino group having 1 to 24 carbon atoms and the arylamino group having 6 to 24 carbon atoms may be linked to each other, and as a more preferable substituent, may be substituted with an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylamino group having 1 to 12 carbon atomsAn arylamino group having 6 to 18 carbon atoms, and the respective alkyl groups or aryl groups in the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms may be linked to each other.
In addition, as a specific example of the compound represented by any one of the [ chemical formula D1] to [ chemical formula D2], among the dopant compounds used for the light-emitting layer of the organic light-emitting element according to the present invention, a compound represented by any one of the following D1 to D239 may be mentioned.
In the present invention, the compound represented by [ chemical formula D3] in the dopant compound in the light-emitting layer may be a compound represented by any one of < D101> to < D130> described below.
In the present invention, the compound represented by any one of the above-mentioned [ chemical formula D4], [ chemical formula D5], [ chemical formula D8] to [ chemical formula D10] among the dopant compounds in the light-emitting layer may be a compound represented by any one of the following < D201 > to < D476 >.
In the present invention, the compound represented by any one of [ chemical formula D6] and [ chemical formula D7] among the dopant compounds in the light-emitting layer may be a compound represented by any one of < D501 > to < D587 > described below.
At this time, the content of the dopant in the light emitting layer may be generally selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
Also, the light emitting layer may additionally include a variety of hosts and a variety of dopant substances in addition to the dopants and hosts.
Hereinafter, an organic light emitting element according to an embodiment of the present invention is described with reference to the accompanying drawings.
Fig. 1 is a diagram showing a structure of an organic light emitting element according to an embodiment of the present invention.
As shown in fig. 1 described above, the organic light emitting element according to the embodiment of the present invention is an organic light emitting element including, in order, an anode 20, a hole transporting layer 40, a light emitting layer 50 including a host and a dopant, an electron transporting layer 60, and a cathode 80, and is an organic light emitting element having the anode as a first electrode, the cathode as a second electrode, and a hole transporting layer between the anode and the light emitting layer, and an electron transporting layer between the light emitting layer and the cathode.
Also, the organic light emitting element according to an embodiment of the present invention may include a hole injection layer 30 between the anode 20 and the hole transport layer 40, and may include an electron injection layer 70 between the electron transport layer 60 and the cathode 80.
The organic light emitting device and the method of manufacturing the same according to the present invention will be described below with reference to fig. 1.
First, an anode (positive electrode) electrode material is coated on the upper portion of the substrate 10, thereby forming an anode 20. Among them, the substrate 10 is usually used as a substrate used for an organic Electroluminescence (EL) element, and is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and water repellency. As the anode electrode material, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) which is transparent and has excellent conductivity are used 2 ) Zinc oxide (ZnO), and the like.
The hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on top of the electrode of the anode 20. Then, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating of a hole transport layer substance on the upper portion of the hole injection layer 30.
The hole injection layer material may be any material commonly used in the art, and for example, 4',4″ -tris [ 2-naphthylphenyl-phenylamino ] triphenylamine (2-TNATA: 4,4',4″ -tris (2-workbench-phenyl) -triphenylamide), N '-bis (1-naphthyl) -N, N' -diphenylbenzidine (NPD: N, N '-di (1-workbench) -N, N' -diphenylbenzidine), N '-bis (3-methylphenyl) -1,1' -biphenyl-4,4'-diamine (TPD: N, N' -diphenyl-N, N '-bis (3-methylphenyl) -1,1' -biphen-4, 4 '-diamine), N' -diphenyl-N, N '-diphenyl-4-diamine, N' -diphenyl-4- [ phenyl-N, N '-biphenyl-4' -biphenyl ] -4, N '-biphenyl-4' -diamine, etc. may be used. However, the present invention is not limited thereto.
The material of the hole transport layer is not particularly limited as long as it is a material commonly used in the art, and for example, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD), N ' -bis (naphthalen-1-yl) -N, N ' -diphenyl benzidine (a-NPD), or the like can be used. However, the present invention is not necessarily limited thereto.
In addition, the present invention may additionally form an electron blocking layer on top of the hole transport layer. The electron blocking layer is a layer that improves the lifetime and efficiency of the element by preventing electrons injected from the electron injection layer from entering the hole transport layer through the light emitting layer, and may be formed at a suitable portion between the light emitting layer and the hole injection layer, preferably, may be formed between the light emitting layer and the hole transport layer.
Next, the light emitting layer 50 may be stacked on top of the hole transport layer 40 or the electron blocking layer by a vacuum deposition method or a spin coating method.
Wherein the light emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.
And, according to a specific example of the present invention, the thickness of the light emitting layer is preferablyTo->
In addition, an electron transport layer 60 is deposited on the light emitting layer by a vacuum deposition method or a spin coating method.
In the present invention, as a material of the electron transport layer, a known electron that has a function of stably transporting electrons injected from an electron injection electrode (Cathode) can be usedThe substance is transported. As examples of the known electron-transporting substances, quinoline derivatives, particularly, those such as tris (8-hydroxyquinoline) aluminum (Alq 3 ) Liq, TAZ, BAlq bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (berylium bis (benzoquinone-10-olate: bebq 2), compound 201, compound 202, BCP, PBD, BMD, BND as an oxadiazole derivative, and the like, but is not limited thereto.
In the organic light-emitting element of the present invention, after the electron transport layer is formed, an electron injection layer EIL, which is a substance having a function of facilitating electron injection from the cathode, may be stacked on top of the electron transport layer, and the material thereof is not particularly limited.
The electron injection layer may be formed of a material such as CsF, naF, liF, li 2 O, baO, etc., are known as a material for forming an electron injection layer. Although the deposition conditions of the electron injection layer are different depending on the compound used, it is generally possible to select from almost the same condition range as that for forming the hole injection layer.
The electron injection layer may have a thickness of aboutTo about->About->To about->The thickness of the electron injection layer is as followsIn the case of the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.
In the present invention, the cathode may use a substance having a small work function to easily inject electrons. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or the like may be used, or a transmissive cathode using ITO, IZO may be used.
Also, the organic light emitting element in the present invention may additionally include a light emitting layer of a blue light emitting material, a green light emitting material, or a red light emitting material that emits light in a wavelength range of 380nm to 800 nm. That is, the light emitting layer in the present invention is a plurality of light emitting layers, and the blue light emitting material, the green light emitting material, or the red light emitting material in the above-described additionally formed light emitting layer may be a fluorescent material or a phosphorescent material.
Also, in the present invention, one or more layers selected from the respective layers may be formed by a single molecule deposition process or a solution process.
Wherein the deposition process means a method of forming a thin film by evaporating a substance used as a material for forming the respective layers by heating or the like in a vacuum or low pressure state, and the solution process means a method of forming a thin film by mixing a substance used as a material for forming the respective layers with a solvent and subjecting it to a method such as ink-jet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, or the like.
The organic light-emitting element according to the present invention can be used for any one device selected from flat panel display devices, flexible display devices, single-color or white flat panel lighting devices, and single-color or white flexible lighting devices.
Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are merely for more specifically explaining the present invention, and the scope of the present invention is not limited thereto, as will be apparent to those having basic knowledge in the art.
Example (example)
Synthesis example 1 Synthesis of chemical formula 19
Synthesis example 1-1.<Synthesis of 1-a >
[ reaction type 1]
A3000 ml round bottom flask was purged with nitrogen and charged with 100g (0.278 mol) of 1, 6-dibromopyrene, 33.9g (0.278 mol) of phenylboronic acid, 6.4g (0.006 mol) of tetrakis (triphenylphosphine) palladium (Pd [ PPh) 3 ] 4 ) 88.3g (0.833 mol) of sodium carbonate, 1400ml of toluene and 420ml of water, and refluxed for 9 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then the resultant solid was filtered and discarded, and after the filtrate was extracted with ethyl acetate and water, the organic layer was subjected to anhydrous treatment. After anhydrous treatment, the mixture was concentrated under reduced pressure and separated by column chromatography to give 45.4g of<1-a > (yield 45.7%).
Synthesis examples 1 to 2.<Synthesis of 1-b
[ reaction type 2]
A500 ml round bottom flask was purged with nitrogen and charged with 20g (0.076 mol) of 6-bromo-1-dibenzofuranol, 11.6g (0.091 mol) of phenylboronic acid (D5), 1.8g (0.002 mol) of tetrakis (triphenylphosphine) palladium (Pd [ PPh) 3 ] 4 ) 17.9g (0.129 mol) of potassium carbonate, 140ml of toluene, 35ml of ethanol and 65ml of water, and refluxed for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted with ethyl acetate and water, and the organic layer was subjected to anhydrous treatment. The organic layer was concentrated under reduced pressure, and then recrystallized from ethyl acetate and heptane to give 15.2g of<1-b > (yield 75.4%).
Synthesis examples 1 to 3.<1-c>Is synthesized by (a)
[ reaction type 3]
A500 ml round bottom flask was purged with nitrogen, 15.2g (0.058 mol) <1-b >, 6g (0.076 mol) pyridine and 150ml dichloromethane were added and cooled to below 0deg.C. After cooling, 18.1g (0.064 mol) of trifluoromethanesulfonic anhydride are slowly added dropwise. After the dropwise addition, the reaction mixture was warmed to room temperature and stirred until the reaction was completed. After the completion of the reaction, the organic layer was subjected to anhydrous treatment with methylene chloride and water, then distilled under reduced pressure, and separated by column chromatography to give 20g <1-c > (yield 87.3%).
Synthesis examples 1 to 4.<Synthesis of 1-d >
[ reaction type 4]
A300 ml round bottom flask was purged with nitrogen, charged with 20g (0.050 mol) <1-c >, 16.6g (0.065 mol) bis (pinacolato) diboron, 0.8g (0.001 mol) bis (diphenylphosphino) ferrocene palladium dichloride, 9.9g (0.101 mol) calcium acetate and 200ml 1, 4-dioxane, and refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, then, the reaction mixture was filtered through celite, and the filtrate was concentrated and separated by column chromatography to give 14.8g (1-d) (yield 78.4%).
Synthesis examples 1 to 5 [ chemical formula 19]]Is synthesized by (a)
[ reaction type 5]
A300 ml round bottom flask was purged with nitrogen and 10.7g (0.030 mol) <1-a >, 13.7g (0.036 mol) <1-d >, 0.7g (0.001 mol) tetrakis (triphenylphosphine) palladium, 7.4g (0.053 mol) potassium carbonate, 80ml toluene, 20ml ethanol and 26ml water were added and refluxed for 4 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and extracted with ethyl acetate and water. The organic layer was subjected to anhydrous treatment, concentrated, and separated by column chromatography to obtain 8.4g [ chemical formula 19] (yield 53.4%).
MS(MALDI-TOF)：m/z 525.21[M] +
Synthesis example 2 Synthesis of formula 34
Synthesis example 2-1.<2-a>Is synthesized by (a)
[ reaction type 6]
Synthesis was performed in the same manner as described above except that phenylboronic acid (D5) was used in place of phenylboronic acid used in Synthesis example 1-1, to obtain <2-a > (yield 79.3%).
Synthesis example 2-2.<Synthesis of 2-b
[ reaction type 7]
Synthesis was carried out in the same manner except for using 1, 7-dibromodibenzofuran instead of 6-bromo-1-dibenzofuranol used in Synthesis example 1-2, to obtain <2-b > (yield 54%).
Synthesis examples 2 to 3.<Synthesis of 2-c >
[ reaction type 8]
The synthesis was performed in the same manner except that <2-b > was used instead of <1-c > used in synthesis examples 1 to 4, to obtain <2-c > (yield 72.8%).
Synthesis examples 2 to 4 [ chemical formula 34]]Is synthesized by (a)
[ reaction type 9]
Synthesis was performed in the same manner as described above except that <2-a > was used in place of <1-a > used in Synthesis examples 1 to 5 and <2-c > was used in place of <1-d >, to obtain [ chemical formula 34] (yield 63.7%).
MS(MALDI-TOF)：m/z 530.25[M] +
Synthesis example 3 Synthesis of chemical formula 52
Synthesis example 3-1.<Synthesis of 3-a >
[ reaction type 10]
The synthesis was performed in the same manner except that 6-bromo-2-dibenzofuranol was used instead of 6-bromo-1-dibenzofuranol used in synthesis examples 1-2 and phenylboronic acid (D5) was used instead of phenylboronic acid, to obtain <3-a > (yield 72.0%).
Synthesis example 3-2.<Synthesis of 3-b
[ reaction type 11]
Synthesis was performed in the same manner except that <3-a > was used in place of <1-b > used in Synthesis example 1-3, to obtain <3-b > (yield 85.2%).
Synthesis examples 3 to 3.<3-c>Is synthesized by (a)
[ reaction type 12]
Synthesis was performed in the same manner except that <3-b > was used in place of <1-c > used in Synthesis examples 1 to 4, to obtain <3-c > (yield 76.8%).
Synthesis examples 3 to 4 [ chemical formula 52]]Is synthesized by (a)
[ reaction type 13]
In Synthesis examples 2 to 4, the synthesis was performed in the same manner except that <3-c > was used instead of <2-c > to obtain [ chemical formula 52] (yield 58.0%).
MS(MALDI-TOF)：m/z 525.21[M] +
Synthesis example 4 Synthesis of chemical formula 131
Synthesis example 4-1 [ chemical formula 131]]Is synthesized by (a)
[ reaction type 14]
In Synthesis examples 2 to 4, the synthesis was performed in the same manner as in <2-c > except that 1-dibenzofuran boronic acid was used instead of <2-c >, to obtain [ chemical formula 131] (yield 61.4%).
MS(MALDI-TOF)：m/z 449.18[M] +
Synthesis example 5 Synthesis of chemical formula 136
Synthesis example 5-1.<5-a>Is synthesized by (a)
[ reaction type 15]
A1000 ml round bottom flask was purged with nitrogen and 50ml (0.477 mole) hydrogen peroxide solution (30 wt%), 45g (0.454 mole) phenol (D5), 57.6g (0.227 mole) iodine and 450ml water were added and stirred at 50℃for 24 hours. When the reaction was completed, a sodium thiosulfate solution was added thereto and stirred, and the reaction mixture was extracted with ethyl acetate and water, followed by anhydrous treatment and concentration under reduced pressure. After concentration, separation was performed by column chromatography, whereby 45g <5-a > (yield 44.3%) was obtained.
Synthesis example 5-2.<Synthesis of 5-b >
[ reaction type 16]
A1000 ml round bottom flask was purged with nitrogen and 45g (0.201 mol) <5-a >, 41g (0.241 mol) 2-fluoro-6-methoxyphenylboronic acid, 7g (0.006 mol) tetrakis (triphenylphosphine) palladium, 47.2g (0.341 mol) potassium carbonate, 315ml toluene, 80ml ethanol and 170ml water were added and refluxed for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with ethyl acetate and water, and then the organic layer was subjected to anhydrous treatment. The organic layer was concentrated under reduced pressure and then separated by column chromatography to give 28.6g <5-b > (yield 64.1%).
Synthesis examples 5 to 3.<Synthesis of 5-c >
[ reaction type 17]
In a 500ml round-bottomed flask, 28.6g (0.129 mol) <5-b >, 44.5g (0.322 mol) potassium carbonate, 143ml 1-methyl-2-pyrrolidine were added and refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, 200ml of a 2N hydrochloric acid solution was slowly added thereto, and after stirring sufficiently, extraction was performed with ethyl acetate and water. The organic layer was concentrated and separated by column chromatography to give 21g <5-c > (yield 80.7%).
Synthesis examples 5 to 4.<Synthesis of 5-d >
[ reaction type 18]
21g (0.104 mol) <5-c >, 120ml of methylene chloride were added to a 500ml round bottom flask, and the reaction mixture was cooled to a temperature of 0℃or lower. 52g (0.208 mol) of boron tribromide are slowly added dropwise while taking care of the temperature. After the dropwise addition, the temperature of the reaction solution was raised to room temperature, followed by stirring until the reaction was completed. When the reaction was completed, 100ml of water was slowly added dropwise to the reaction solution, followed by stirring thoroughly. The reaction mixture was extracted with methylene chloride and water, then subjected to anhydrous treatment and concentration under reduced pressure, and separated by column chromatography to give 15g <5-d > (yield 76.8%).
Synthesis examples 5 to 5.<Synthesis of 5-e >
[ reaction type 19]
A500 ml round bottom flask was purged with nitrogen, 15.0g (0.080 mol) <5-d >, 8g (0.104 mol) pyridine, 150ml dichloromethane were added and the reaction solution temperature was cooled to below 0 ℃. After cooling, 24.7g (0.088 mol) of trifluoromethanesulfonic anhydride were slowly added dropwise. After the dropwise addition, the temperature of the reaction solution was raised to room temperature, and stirred until the reaction was completed. After the completion of the reaction, the organic layer was extracted with methylene chloride and water, then subjected to anhydrous treatment and concentration under reduced pressure, and separated by column chromatography to give 20g <5-e > (yield 78.4%).
Synthesis examples 5 to 6.<5-f>Is synthesized by (a)
[ reaction type 20]
A500 ml round bottom flask was purged with nitrogen and charged with 20g (0.062 mol) <5-e >, 23.8g (0.094 mol) bis (pinacolato) diboron, 2.5g (0.003 mol) bis (diphenylphosphino) ferrocene palladium dichloride, 9.5g (0.125 mol) calcium acetate and 200ml 1, 4-dioxane and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered through celite, and the filtrate was concentrated and separated by column chromatography to give 15g <5-f > (yield 80.6%).
Synthesis examples 5 to 7 [ chemical formula 136]]Is synthesized by (a)
[ reaction type 21]
In Synthesis examples 2 to 4, the reaction was conducted in the same manner except that <5-f > was used in place of <2-c > to obtain [ chemical formula 136] (yield 60.3%).
MS(MALDI-TOF)：m/z 453.21[M] +
Synthesis example 6 Synthesis of formula 1
Synthesis example 6-1.<Synthesis of 6-a >
[ reaction type 22]
The synthesis was performed in the same manner as described above except that phenylboronic acid (D5) used in Synthesis example 1-2 was replaced with phenylboronic acid, whereby <6-a > (yield 57%) was obtained.
Synthesis example 6-2.<6-b>Is synthesized by (a)
[ reaction type 23]
Synthesis was performed in the same manner except that <6-a > was used in place of <1-b > used in Synthesis examples 1 to 3, to obtain <6-b > (yield 86.8%).
Synthesis example 6-3.<Synthesis of 6-c >
[ reaction type 24]
Synthesis was performed in the same manner except that <6-b > was used in place of <1-c > used in Synthesis examples 1 to 4, to obtain <6-c > (yield 79.2%).
Synthesis example 6-4 [ chemical formula 1]]Is synthesized by (a)
[ reaction type 25]
The synthesis was performed in the same manner except that 1-bromopyrene was used in place of <1-a > used in Synthesis examples 1 to 5 and <6-c > was used in place of <1-d >, to obtain [ chemical formula 1] (yield 52.5%).
MS(MALDI-TOF)：m/z 444.15[M] +
Synthesis example 7 Synthesis of chemical formula 23
Synthesis example 7-1 [ chemical formula 23]]Is synthesized by (a)
[ reaction type 26]
The synthesis was performed in the same manner except that <6-c > was used instead of <1-d > used in synthesis examples 1 to 5, to obtain [ chemical formula 23] (yield 53.8%).
MS(MALDI-TOF)：m/z 520.18[M] +
Synthesis example 8 Synthesis of chemical formula 41
Synthesis example 8-1 [ chemical formula 41]]Is synthesized by (a)
[ reaction type 27]
[ chemical formula 41] (yield 54.2%) was obtained by the same method except that <2-a > was used instead of <1-a > used in Synthesis examples 1 to 5.
MS(MALDI-TOF)：m/z 530.25[M] +
Synthesis example 9 Synthesis of formula 57
Synthesis example 9-1 [ chemical formula 57]]Is synthesized by (a)
[ reaction type 28]
The synthesis was performed in the same manner except that <3-c > was used instead of <1-d > used in synthesis examples 1 to 5, to obtain [ chemical formula 57] (yield 53.5%).
MS(MALDI-TOF)：m/z 520.18[M] +
Examples 1 to 13: manufacture of organic light-emitting elementManufacturing process
The ITO glass was patterned so that the light-emitting area of the ITO glass reached a size of 2mm×2mm, and then washed. After the ITO glass was mounted in a vacuum chamber, the base pressure was set to 1X 10 -7 Torr, then on ITO according to DNTPDα-NPDIs formed in sequence. The host compound according to the present invention and the dopant (BD) (3 wt%) described below were mixed to form a film->As a light-emitting layer, [ E-1 ] is then sequentially deposited]And [ E-2 ]]At a ratio of 1:1Film formation as an electron transport layer, and [ E-2 ]]AlAn organic light-emitting element was manufactured by forming a film as an electron injection layer. The light emission characteristics of the organic light emitting element were measured at 0.4 mA. / >
Comparative examples 1 to 4
The organic light-emitting element used in the comparative example was manufactured and tested in the same manner except that the following [ BH1], [ BH2] was used instead of the compound according to the present invention used as the main body in the element structure of the above-described example, and the light-emitting characteristics of the organic light-emitting element were measured at 0.4 mA. The structure of [ BH1] and [ BH2] is as follows:
TABLE 1
TABLE 2
| Main body | LT 97 | CIEx | CIEy | |
| Example 10 | Chemical formula 41 | 210 | 0.133 | 0.101 |
| Example 11 | Chemical formula 50 | 181 | 0.134 | 0.101 |
| Example 12 | Chemical formula 35 | 194 | 0.133 | 0.101 |
| Example 13 | Chemical 136 | 270 | 0.134 | 0.102 |
| Comparative example 3 | [BH1] | 143 | 0.133 | 0.103 |
| Comparative example 4 | [BH2] | 148 | 0.133 | 0.102 |
As shown in the above table 1, in the organic light emitting element using the compound in which the pyrene group is bonded to the No. 1 or No. 2 position of the dibenzofuranyl group in the light emitting layer according to the present invention, the organic light emitting element can be driven at a low voltage and exhibits excellent characteristics of light emitting efficiency as compared with the organic light emitting element using the compound BH1 or BH2 in which the pyrene group is bonded to the No. 3 or No. 4 position of the dibenzofuranyl group in the light emitting layer, and as shown in table 2, the organic light emitting element using the compound in which the pyrene group is bonded to the No. 1 or No. 2 position of the dibenzofuranyl group in the light emitting layer according to the present invention exhibits excellent characteristics of long life as compared with the organic light emitting element in which the compound BH1 or BH2 in which the pyrene group is bonded to the No. 3 or No. 4 position of the dibenzofuranyl group is used in the light emitting layer.
Industrial applicability
The organic light-emitting element having a light-emitting layer manufactured using the compound according to the present invention has improved high efficiency, low voltage driving, and long life characteristics as compared with conventional compounds, and thus exhibits improved characteristics when applied to an organic light-emitting element, and further has high industrial applicability in the organic light-emitting element and the industrial fields related thereto.
Claims (19)
1. A compound represented by the following [ chemical formula a ] or [ chemical formula B ]:
in the [ chemical formula A ] and the [ chemical formula B ],
the R is 1 To R 14 And are each the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group;
The said connectionLinker L 1 L and L 2 Are each the same or different from each other and are each independently one selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms;
the n1 and n2 are each the same or different and are each independently an integer from 0 to 2, each linker L in the case where n1 and n2 are each 2 1 L and L 2 Are the same as or different from each other,
the R and R' are the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group;
Wherein n3 and n4 are the same or different, and each is an integer of 1 to 9, and each R and R' is the same or different when n3 and n4 are 2 or more,
in the [ chemical formula a ] and the [ chemical formula B ], the "substitution" in the "substituted or unsubstituted" means substitution with one or more substituents selected from the group consisting of: deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, haloalkyl having 1 to 24 carbon atoms, alkenyl having 1 to 24 carbon atoms, alkynyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, heteroalkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, aralkyl having 7 to 24 carbon atoms, alkylaryl having 7 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, heteroaralkyl having 2 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, alkylamino having 1 to 24 carbon atoms, diarylamino having 12 to 24 carbon atoms, diheteroarylamino having 2 to 24 carbon atoms, aryl (heteroaryl) amino having 7 to 24 carbon atoms, alkylsilyl having 1 to 24 carbon atoms, arylsilyl having 6 to 24 carbon atoms, aryloxy having 6 to 24 carbon atoms, and arylene having 6 to 24 carbon atoms.
2. A compound according to claim 1, wherein,
the compound represented by the [ formula a ] includes at least one or more deuterium,
the compound represented by the [ chemical formula B ] includes at least one or more deuterium.
3. A compound according to claim 2, wherein,
said [ formula A ]]R in (a) 1 To R 7 At least one of which is a substituent comprising deuterium,
said [ formula B ]]R in (a) 8 To R 14 At least one of which is a substituent comprising deuterium.
4. A compound according to claim 2, wherein,
at least one R in the [ chemical formula A ] is a substituent comprising deuterium,
at least one R' in the [ formula B ] is a substituent including deuterium.
5. A compound according to claim 1, wherein,
said [ formula A ]]R in (a) 1 To R 7 At least one of which is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,
said [ formula B ]]R in (a) 8 To R 14 At least one of which is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
6. A compound according to claim 1, wherein,
said [ formula A ]]Said [ formula B ]]The linker L in (2) 1 L and L 2 Is a single bond, or is selected from the following [ structural formula 1 ] ]To [ Structure 5 ]]Any one of the following:
in the linking group, the carbon of the aromatic ring can be bonded to hydrogen or deuterium.
7. A compound according to claim 6, wherein,
the linker L 1 L and L 2 Respectively single bonds.
8. A compound according to claim 1, wherein,
at least one R in the [ chemical formula A ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,
at least one R' in the [ chemical formula B ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
9. A compound according to claim 8 wherein,
the n3 and the n4 in the [ chemical formula A ] and the [ chemical formula B ] are respectively 1,
r in the [ chemical formula A ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,
r' in the [ chemical formula B ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
10. A compound according to claim 1, wherein,
the organic compound represented by the [ chemical formula A ] or the [ chemical formula B ] is a compound represented by any one of the following [ chemical formula A-1] or the [ chemical formula B-1 ]:
in the [ chemical formula A-1] and the [ chemical formula B-1],
The substituent R 1 To R 14 Linker L 1 L and L 2 N1 and n2 and [ formula A ] in claim 1]Or [ formula B ]]The content defined in (a) is the same,
the substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.
11. A compound according to claim 1, wherein,
the n3 and the n4 in the [ chemical formula A ] and the [ chemical formula B ] are respectively 1,
said [ formula A ]]R in (a) 1 To R 7 At least one of R is an aryl group having 6 to 18 carbon atoms substituted with deuterium,
said [ formula B ]]R in (a) 8 To R 14 At least one of R' is an aryl group having 6 to 18 carbon atoms substituted with deuterium.
12. A compound according to claim 1, wherein,
the n3 and the n4 in the [ chemical formula A ] and the [ chemical formula B ] are respectively 1,
r in the [ chemical formula A ] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms,
r' in the [ chemical formula B ] is a substituted or unsubstituted heteroaryl group with 2 to 18 carbon atoms.
13. A compound according to claim 1, wherein,
the compound is any one selected from the group represented by the following [ chemical formula 1] to [ chemical formula 240 ]:
14. An organic light emitting element comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer sandwiched between the first electrode and the second electrode,
wherein the organic layer comprises one or more compounds selected from any one of claims 1 to 13.
15. The organic light-emitting device according to claim 14, wherein,
the organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.
16. The organic light-emitting device according to claim 15, wherein,
the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer formed using a host and a dopant, and the compound is used as the host.
17. The organic light-emitting device according to claim 16, wherein,
any one or more selected from the following [ chemical formula D1] to [ chemical formula D10] is used as the dopant,
[ chemical formula D1]
[ chemical formula D2]
In said [ chemical formula D1] ]Said [ formula D2 ]]In (A) 31 、A 32 、E 1 F (F) 1 Are each identical or different and independently of one another are substituted or unsubstituted and have the number of carbon atomsAn aromatic hydrocarbon ring of 6 to 50 or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
the A is 31 Two carbon atoms adjacent to each other in the aromatic ring of (A) and the A 32 Two carbon atoms adjacent to each other in the aromatic ring of (a) and attached to the substituent R 51 R is R 52 Forming five-membered rings from carbon atoms of (2) to form condensed rings, respectively;
the linker L 21 To L 32 And are each the same or different and are each independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
the W and W' are each the same or different from each other and are each independently selected from N-R 53 、CR 54 R 55 、SiR 56 R 57 、GeR 58 R 59 Either one of O, S, se;
the substituent R 51 To R 59 、Ar 21 To Ar 28 Are each the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atomsAn unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, a halogen group,
The R is 51 R is R 52 Can be linked to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, wherein the carbon atoms of the alicyclic, aromatic monocyclic or polycyclic ring can be replaced by one or more hetero atoms selected from N, O, P, si, S, ge, se, te;
the p11 to p14, r11 to r14 and s11 to s14 are integers of 1 to 3, respectively, and in the case where they are 2 or more, each linker L 21 To L 32 Respectively, are the same as or different from each other,
wherein x1 is 1, y1, z1 and z2 are each the same or different and are each independently an integer of 0 to 1,
the Ar is as follows 21 Ar and Ar 22 、Ar 23 Ar and Ar 24 、Ar 25 Ar and Ar 26 Ar, ar 27 Ar and Ar 28 May be respectively connected to each other to form a ring;
in said [ chemical formula D1 ]]In (A) 32 Two carbon atoms adjacent to each other within the ring and the structural formula Q 11 Is combined to form a condensed ring,
in said [ chemical formula D2 ]]In said A 31 Two carbon atoms adjacent to each other in the ring may be of the formula Q 12 To form a condensed ring, said A 32 Two carbon atoms adjacent to each other in the ring may be adjacent to the structural formula Q 11 Is combined to form a condensed ring,
[ chemical formula D3]
In the above-mentioned [ chemical formula D3],
the X is 1 Is any one selected from B, P, P =o,
the T1 to T3 are each the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
The Y is 1 Is selected from N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Any one of them;
the Y is 2 Is selected from N-R 66 、CR 66 R 68 、O、S、SiR 69 R 70 Any one of them;
the R is 61 To R 70 Each of which is the same as or different from the other and is each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, and any one of the above groups, and R is a cyano group 61 To R 70 Can be combined with one or more rings selected from the group consisting of T1 to T3 to additionally form an alicyclic or aromatic monocyclic ring or polycyclic ring,
In the [ chemical formula D4] and the [ chemical formula D5],
the X is 2 Is any one selected from B, P, P =o,
t4 to T6 are the same as T1 to T3 in [ formula D3],
the Y is 4 Is selected from N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Any one of them;
the Y is 5 Is selected from N-R 66 、CR 66 R 68 、O、S、SiR 69 R 70 Any one of them;
the Y is 6 Is selected from N-R 71 、CR 72 R 73 、O、S、SiR 74 R 75 Any one of them;
the R is 61 To R 75 And [ chemical formula D3]]Said R in (a) 61 To R 70 The same is true of the fact that,
the X is 3 Is any one selected from B, P, P =o,
t7 to T9 are the same as T1 to T3 in [ formula D3],
the Y is 6 Is selected from N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Any one of them;
the substituent R 61 To R 65 、R 71 To R 72 Respectively with [ chemical formula D3]]Said R in (a) 61 To R 70 The same is true of the fact that,
the R is 71 And R is 72 May be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or may be combined with the T7 ring or T9 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, respectively，
[ chemical formula D10]
In the [ chemical formula D8] to the [ chemical formula D10],
wherein X is any one selected from B, P, P =O,
the Q is 1 To Q 3 Respectively with [ chemical formula D3]]In (2) are the same as T1 to T3,
the linker Y is selected from N-R 3 、CR 4 R 5 Either one of the two or more of O, S, se,
the substituent R 3 To R 5 Respectively with [ chemical formula D3] ]Said R in (a) 61 To R 70 The same is true of the fact that,
the R is 3 To R 5 Can be separately with the Q 2 Ring or Q 3 The rings combine to additionally form a single or multiple ring that is alicyclic or aromatic,
the R is 4 And R is 5 May be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,
for the ring formed by the Cy1, if the nitrogen (N) atom is removed, Q bonded to the nitrogen (N) atom 1 An aromatic carbon atom in the ring and Q to be bonded to said Cy1 1 The aromatic carbon atom in the ring is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
in the chemical formula D9 of the present invention,
the Cy2 is attached to the Cy1 to form a saturated hydrocarbon ring, and the ring formed by the Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms if the carbon atom included in the Cy1 is removed,
in the chemical formula D10 described above, the chemical formula,
for the ring formed by the Cy3, if Q to be bound to the Cy3 is removed 3 An aromatic carbon atom in the ring, an aromatic carbon atom in Q3 to be bonded to a nitrogen (N) atom, a carbon atom in Cy1 to which the nitrogen (N) atom is bonded, is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
Wherein "substitution" in the "substituted or unsubstituted" in the [ chemical formula D1] to [ chemical formula D10] means substitution with one or more substituents selected from the group consisting of: deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, haloalkyl having 1 to 24 carbon atoms, alkenyl having 2 to 24 carbon atoms, alkynyl having 2 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, heteroalkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, aralkyl having 7 to 24 carbon atoms, alkylaryl having 7 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, heteroaralkyl having 2 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, alkylamino having 1 to 24 carbon atoms, diarylamino having 12 to 24 carbon atoms, diheteroarylamino having 2 to 24 carbon atoms, aryl (heteroaryl) amino having 7 to 24 carbon atoms, alkylsilyl having 1 to 24 carbon atoms, arylsilyl having 6 to 24 carbon atoms, aryloxy having 6 to 24 carbon atoms, and arylene having 6 to 24 carbon atoms.
18. The organic light-emitting device according to claim 15, wherein,
More than one layer selected among the respective layers is formed through a deposition process or a solution process.
19. The organic light-emitting device according to claim 14, wherein,
the organic light emitting element is used for any one device selected from a flat panel display device, a flexible display device, a device for single-color or white flat panel illumination, and a device for single-color or white flexible illumination.
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| KR10-2021-0098698 | 2021-07-27 | ||
| PCT/KR2021/009864 WO2022114444A1 (en) | 2020-11-26 | 2021-07-29 | Novel organic compound, and organic light-emitting device comprising same |
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