CN113735780A - Benzo five-membered heterocyclic derivative and organic electroluminescent device thereof - Google Patents
Benzo five-membered heterocyclic derivative and organic electroluminescent device thereof Download PDFInfo
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- CN113735780A CN113735780A CN202111131169.7A CN202111131169A CN113735780A CN 113735780 A CN113735780 A CN 113735780A CN 202111131169 A CN202111131169 A CN 202111131169A CN 113735780 A CN113735780 A CN 113735780A
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 40
- 125000005605 benzo group Chemical group 0.000 title claims abstract description 38
- 230000000903 blocking effect Effects 0.000 claims abstract description 25
- 239000010410 layer Substances 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 12
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 64
- 239000000758 substrate Substances 0.000 abstract description 22
- 239000011521 glass Substances 0.000 abstract description 11
- 238000000605 extraction Methods 0.000 abstract description 9
- 230000005540 biological transmission Effects 0.000 abstract description 8
- 230000006798 recombination Effects 0.000 abstract description 5
- 238000005215 recombination Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 description 109
- 238000003786 synthesis reaction Methods 0.000 description 109
- 150000001875 compounds Chemical class 0.000 description 74
- 238000004128 high performance liquid chromatography Methods 0.000 description 40
- 238000001819 mass spectrum Methods 0.000 description 40
- -1 3-dimethylbutyl Chemical group 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 30
- 238000001704 evaporation Methods 0.000 description 28
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004140 cleaning Methods 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 239000002346 layers by function Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004506 ultrasonic cleaning Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229940125758 compound 15 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 4
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 3
- 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 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 3
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 229940125846 compound 25 Drugs 0.000 description 3
- 229940125851 compound 27 Drugs 0.000 description 3
- 229940125878 compound 36 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 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 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
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
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Abstract
The invention provides a benzo five-membered heterocyclic derivative and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The benzo five-membered heterocyclic derivative provided by the invention has good electron mobility, can effectively promote the transmission balance of holes and electrons, has good hole blocking capability, can effectively block the holes in a luminescent layer, increases the recombination probability of the holes and the electrons, is applied to a hole blocking layer or an electron transmission layer of an organic electroluminescent device, and can effectively improve the luminous efficiency and the service life of the device; in addition, the benzo five-membered heterocyclic derivative is applied to an organic electroluminescent device as a light extraction material, can effectively solve the problem of total emission generated at the interface of an electrode film and a glass substrate and the interface of the glass substrate and air, and improves the light extraction efficiency, thereby improving the luminous efficiency and the service life of the organic electroluminescent device.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a benzo five-membered heterocyclic derivative and an organic electroluminescent device thereof.
Background
The development of Display technology mainly goes through three stages of Cathode Ray Tube (CRT), Liquid Crystal Display (LCD) and Organic Light Emitting Display (OLED). Among them, the CRT, which is the earliest used in television and computer display, adopts a display of a green display tube and a single display tube, but gradually quits the historical stage due to its high power consumption, large volume, radiation, inability to realize large screen, insufficient high definition of pixels, and other disadvantages. Later, the LCD replaces the CRT technology to become the mainstream technology in the display field, and the sales share exceeds the CRT, but the LCD display technology needs to rely on the backlight source to emit light, and cannot simultaneously meet the requirements of fast response speed, wide color gamut, low power consumption, large screen, and even flexible display. Based on the series of requirements, the third generation flat panel display technology organic light emitting technology OLED is coming.
The OLED technology refers to a technology in which an organic material emits light under the action of an electric field, and a typical structure is a structure in which an organic functional layer is inserted between a cathode and an anode to form a sandwich-like structure, wherein the organic functional layer may be divided into a single-layer structure, a double-layer structure, a three-layer structure, and a multi-layer structure according to the design requirements of devices. The initial device is the simplest structure comprising a single organic functional layer, and the single organic functional layer simultaneously takes charge of electron transmission and hole transmission, so that the bipolar requirement on the material is high; on the other hand, the light-emitting layer directly contacts the cathode and the anode, so that the recombination probability of excitons is reduced to a great extent, and the luminous efficiency of the device is low. In order to increase the exciton recombination probability and realize high-efficiency light emission, the number of layers of organic functional layers is gradually increased, and the functions exerted by each functional layer tend to be single, and the current organic functional layers can be divided into a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a light extraction layer and the like.
The functional layers of organic electroluminescent devices are advantageous on the basis of the good properties of the materials, so that the choice of materials is very critical in the production of the devices. From the structural point of view of the device, organic electroluminescent materials can be roughly classified into three types: electrode material, electrode modifying material, carrier transmission material and luminescent material. Although the performance of light-emitting materials and electrode materials is very important for organic electroluminescent devices, the performance of the devices needs to be improved comprehensively, and many auxiliary materials with excellent properties, such as transport materials and the like, are also needed, such as hole injection materials, hole transport materials, electron blocking materials, hole blocking materials, electron transport materials, electron injection materials, light extraction materials and the like. The improvement of the performance of the materials is beneficial to the improvement of the performance of the organic electroluminescent device, so that the research and development of new auxiliary materials are of great significance.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a benzo five-membered heterocyclic derivative and an organic electroluminescent device thereof.
The invention provides a benzo five-membered heterocyclic derivative which has a structure shown as a formula (I),
n is selected from 3,4 or 5; ar (Ar)1Independently selectFrom the structure shown in the following,
said X1Selected from O, S, NR1Any one of the above;
the R is1Any one selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl and substituted or unsubstituted C6-C30 aryl;
the R is2Any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; m is selected from 0, 1,2,3 or 4, when m is greater than 1, a plurality of R2Two R's which are the same or different from each other, or adjacent to each other2Can be connected into a ring;
said Y is1～Y4Independently selected from N or C;
said L1～L3Independently selected from any one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted C3-C30 heteroarylene;
ar is2Is a structure shown in a formula (III),
said X2Selected from O, S, N (R)3)、C(R3R4) One of (1), R3、R4Independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio,Any one of substituted or unsubstituted arylamine groups of C6-C20, or R3、R4Can be connected into a ring;
the R is5、R6Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or two adjacent R5Or R6Can be connected into a ring;
p and q are independently selected from 0, 1,2,3 or 4;
the above-mentioned "substituted or unsubstituted alkyl group", "substituted or unsubstituted cycloalkyl group", "substituted or unsubstituted alkenyl group", "substituted or unsubstituted cycloalkenyl group", "substituted or unsubstituted aryl group", "substituted or unsubstituted heteroaryl group", "substituted or unsubstituted aryloxy group", "substituted or unsubstituted arylthio group", "substituted or unsubstituted arylamine group", "substituted or unsubstituted arylene group", "substituted or unsubstituted heteroarylene group" are each substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, and substituted or unsubstituted C3 to C30 heteroaryl group, when substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other; or when the substituent is plural, adjacent substituents may be linked to form a ring.
The invention also provides an organic electroluminescent device which comprises an anode, an organic layer and a cathode, wherein the organic layer comprises the benzo five-membered heterocyclic derivative.
Has the advantages that: the benzo five-membered heterocyclic derivative provided by the invention has good electron mobility, provides assistance in the electron transmission process, can effectively promote the transmission balance of holes and electrons, has a deep HOMO energy level, has good hole blocking capability, can effectively block the holes in a light-emitting layer, increases the recombination probability of the holes and the electrons, is applied to a hole blocking layer or an electron transmission layer of an organic electroluminescent device, and can effectively improve the light-emitting efficiency of the device and prolong the service life; in addition, the benzo five-membered heterocyclic derivative is applied to an organic electroluminescent device as a light extraction material, can effectively solve the problem of total emission of an interface between an electrode film and a glass substrate and an interface between the glass substrate and air, reduces total reflection loss and waveguide loss of light in the device, and improves the light extraction efficiency, thereby improving the luminous efficiency of the organic electroluminescent device.
Detailed Description
The present invention is further illustrated by the following examples, which are intended to be purely exemplary and are not intended to limit the scope of the invention, as various equivalent modifications of the invention will fall within the scope of the claims of this application after reading the present invention.
The alkyl group in the present invention refers to a group obtained by removing one hydrogen atom from an alkane molecule, and includes a straight-chain alkyl group and a branched-chain alkyl group. The number of carbon atoms of the alkyl group is not particularly limited, and is preferably C1 to C60, more preferably C1 to C30, still more preferably C1 to C15, and most preferably C1 to C10. Examples of alkyl groups include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, 2-ethylbutyl, 3-dimethylbutyl, 4-methyl-2-pentyl, 1-methylheptyl, and the like, but are not limited thereto.
The cycloalkyl group in the present invention is a group obtained by removing one hydrogen atom from a cycloalkane molecule, and the number of carbon atoms of the cycloalkyl group is not particularly limited, but is preferably C3 to C60, more preferably C3 to C30, still more preferably C3 to C15, and most preferably C3 to C10. Examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctane, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, adamantyl, bornyl, norbornyl, cubic alkyl and the like, but are not limited thereto.
The alkenyl group in the present invention is a group obtained by removing one hydrogen atom from an olefin molecule, and includes a linear alkenyl group and a branched alkenyl group, and the number of carbon atoms of the alkenyl group is not particularly limited, and is preferably C2 to C60, more preferably C2 to C30, even more preferably C2 to C15, and most preferably C2 to C10. Examples of alkenyl groups include: vinyl, vinyl chloride, styrene, propenyl, and the like, but is not limited thereto.
The cycloalkenyl group in the present invention is a group obtained by removing one hydrogen atom from a cycloolefin molecule, and the number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably C3 to C60, more preferably C3 to C20, even more preferably C3 to C15, and most preferably C3 to C10. Examples of cycloalkenyl groups include: cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclobutadiene, cyclopentadiene, cycloheptene, 1, 3-cyclohexadiene, 1, 4-cyclohexadiene, and the like, but are not limited thereto.
The aryl group in the present invention is a group obtained by removing one hydrogen atom from the aromatic nucleus of an aromatic hydrocarbon molecule, and includes monocyclic aryl groups, polycyclic aryl groups and condensed ring aryl groups, and the number of carbon atoms in the aryl group is not particularly limited, and is preferably C6 to C60, more preferably C6 to C30, further preferably C6 to C18, most preferably C6 to C12. Examples of aryl groups include: phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, benzopyrenyl, perylenyl, fluoranthenyl, indenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, dibenzospirobifluorenyl, and the like, but is not limited thereto.
The heteroaryl group of the present invention refers to a group obtained by removing one hydrogen from the aromatic nucleus of a heterocyclic aromatic hydrocarbon molecule, and the heteroatoms in the heteroaryl group include, but are not limited to: o, S, N, Si, B, P, Se. The heteroaryl group includes monocyclic heteroaryl groups, polycyclic heteroaryl groups and fused ring heteroaryl groups, and the number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably C3 to C60, more preferably C3 to C30, still more preferably C3 to C15, most preferably C3 to C8. Examples of heteroaryl groups include: pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, oxadiazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, thiazolyl, benzothiazolyl, naphthothiazolyl, phenanthrothiazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, furanyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, acridinyl, and the like, but is not limited thereto.
The arylene group in the present invention is a group obtained by removing two hydrogen atoms from an aromatic nucleus in an aromatic hydrocarbon molecule, and includes monocyclic arylene group, polycyclic arylene group, condensed ring arylene group, or a combination thereof, and the number of carbon atoms of the arylene group is not particularly limited, and is preferably C6 to C60, more preferably C6 to C30, even more preferably C6 to C18, and most preferably C6 to C12. Examples of the arylene group include: phenylene, biphenylene, terphenylene, quaterphenylene, naphthylene, phenanthrylene, anthracenylene, triphenylene, pyrenylene, fluorenylene, benzofluorenylene, spirobifluorenylene, benzospirobifluorenylene, and the like, but are not limited thereto.
Heteroarylene as used herein refers to a group obtained by removing two hydrogen atoms from the aromatic nucleus of a heteroaromatic molecule, where the heteroatoms include, but are not limited to: o, S, N, Si, B, P, Se. Heteroarylene includes monocyclic heteroarylene, polycyclic heteroarylene and fused ring heteroarylene, and the polycyclic heteroarylene may have only one benzene ring substituted with a heteroatom or may have a plurality of benzene rings substituted with a heteroatom. The number of carbon atoms of the heteroarylene group is not particularly limited, and is preferably C6 to C60, more preferably C6 to C30, still more preferably C3 to C15, and most preferably C3 to C8. Examples of heteroarylenes include: pyridyl, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, furanylene, thiophenylene, quinolinylene, isoquinolinylene, quinoxalylene, quinazolinylene, phenanthroline-ylene, benzofuranylene, dibenzofuranylene, benzothiophenylene, dibenzothiophenylene, carbazolyl, benzocarbazolyl, and the like, but are not limited thereto.
The term "substituted or unsubstituted" as used herein means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen, amino, cyano, nitro, acyl, ester, carbonyl, haloalkyl, haloalkoxy, substituted or unsubstituted alkyl of C1-C60, substituted or unsubstituted cycloalkyl of C3-C30, substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C3-C30, substituted or unsubstituted arylamine of C6-C30, substituted or unsubstituted aryloxy of C6-C30, preferably deuterium, cyano, halogen, alkyl of C1-C10, cycloalkyl of C3-C12, aryl of C6-C20, heteroaryl of C3-C20, and specific examples may include deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclohexyl, adamantyl, phenyl, tolyl, mesityl, penta-phenyl, biphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, 9-dimethyl-fluorenyl, 9, and 9,9, 9-diphenylfluorenyl group, pyrenyl group, triphenylenyl group, and the like,
A phenyl group, a perylene group, a spirobifluorenyl group, a carbazoloindolyl group, a pyrrolyl group, a carbazolyl group, a furyl group, a benzofuryl group, a dibenzofuryl group, a thienyl group, a benzothienyl group, a benzimidazolyl group, a pyridooxazole group, a pyridothiazole group, a pyridoimidazole group, a naphthyridooxazole group, a naphthyridothiazole group, a naphthyridoimidazole group, a quinolyl group, an isoquinolyl group, a phenothiazinyl group, a phenoxazinyl group, an acridinyl group, a dibenzothienyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, an oxazolyl group, a thiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzotriazolyl group, and the like, but are not limited thereto.
The "-" on the substituent groups described herein represents the attachment site.
The halogen in the invention comprises fluorine, chlorine, bromine and iodine.
The linking to form a ring according to the present invention means that two groups are linked to each other by a chemical bond and optionally subjected to aromatization. As exemplified below:
in the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, such as a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a dibenzofuran ring, a dibenzothiophene ring, a phenanthrene ring, a pyrene ring, etc., but is not limited thereto.
In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example,
can represent
And so on.
The invention provides a benzo five-membered heterocyclic derivative which has a structure shown as a formula (I),
n is selected from 3,4 or 5; ar (Ar)1Independently selected from the structures shown below,
said X1Selected from O, S, NR1One of (1);
the R is1Any one selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl and substituted or unsubstituted C6-C30 aryl;
the R is2Selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30Any one of aryl and substituted or unsubstituted heteroaryl of C3-C30; m is selected from 0, 1,2,3 or 4, when m is greater than 1, a plurality of R2Two R's which are the same or different from each other, or adjacent to each other2Can be connected into a ring;
said Y is1～Y4Independently selected from N or C;
said L1～L3Independently selected from any one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted C3-C30 heteroarylene;
ar is2Is a structure shown in a formula (III),
said X2Selected from O, S, N (R)3)、C(R3R4) Any one of (1), R3、R4Independently selected from any one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C20 arylamine, or R3、R4Can be connected into a ring;
the R is5、R6Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or two adjacent R5Or R6Can be connected into a ring;
p and q are independently selected from 0, 1,2,3 or 4;
the above-mentioned "substituted or unsubstituted alkyl group", "substituted or unsubstituted cycloalkyl group", "substituted or unsubstituted alkenyl group", "substituted or unsubstituted cycloalkenyl group", "substituted or unsubstituted aryl group", "substituted or unsubstituted heteroaryl group", "substituted or unsubstituted aryloxy group", "substituted or unsubstituted arylthio group", "substituted or unsubstituted arylamine group", "substituted or unsubstituted arylene group", "substituted or unsubstituted heteroarylene group" are each substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, and substituted or unsubstituted C3 to C30 heteroaryl group, when substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other; or when the substituent is plural, adjacent substituents may be linked to form a ring.
Preferably, the benzo five-membered heterocyclic derivative is selected from any one of the following chemical formulas:
said X1Selected from O, S, NR1Any one of the above;
the R is1Any one selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C20 aryl;
the R is2Any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl; m is selected from 0, 1,2,3 or 4, when m is greater than 1, a plurality of R2Two R's which are the same or different from each other, or adjacent to each other2Can be connected into a ring;
said Y is1～Y4Independently selected from N or C;
said L1～L3Independently selected from any one of single bond, substituted or unsubstituted arylene of C6-C20 and substituted or unsubstituted C3-C20 heteroarylene;
said X2Selected from O, S, N (R)3)、C(R3R4) One of (1), R3、R4Independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 cycloalkenyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C6-C20 arylthio, substituted or unsubstituted C6-C20 arylamine, or R3、R4Can be connected into a ring;
the R is5、R6Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 cycloalkenyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, or two adjacent R5Or R6Can be connected into a ring;
and p and q are independently selected from 0, 1,2,3 or 4.
Preferably, Ar is1Any one selected from the following groups:
preferably, Ar is2Any one selected from the following groups:
the R is7、R8、R9、R10、R11Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 cycloalkenyl, substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl, or adjacent two substituents can be connected to form a ring;
a is a1Selected from 0, 1,2,3, 4,5, 6 or 7; a is2Selected from 0, 1,2,3, 4 or 5; a is3Selected from 0, 1,2,3 or 4; a is4Selected from 0, 1,2,3, 4,5, 6, 7 or 8; a is5Selected from 0, 1,2 or 3;
the R isaAnd any one selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C20 aryl.
Preferably, Ar is2Any one selected from the following groups:
preferably, said L1～L3Independently selected from a single bond or any one of the following groups,
preferably, the heterocyclic derivative is selected from any one of the structures shown in the following,
the present invention is not limited to the listed chemical structures, and any substituent group defined above is included on the basis of the structure shown in formula I.
Further, the invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises the benzo five-membered heterocyclic derivative.
Preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a hole blocking layer and/or an electron transport layer, and the hole blocking layer and/or the electron transport layer comprise the benzo five-membered heterocycle derivative of the invention.
Preferably, the organic layer is located on the side of the cathode facing away from the anode, and the organic layer comprises a capping layer comprising the benzo five-membered heterocycle derivative of the invention described above.
The organic layer in the organic electroluminescent device of the present invention may include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, and the like. Each functional layer may be composed of a single layer or may be composed of a plurality of layers, and each layer may contain one material or a plurality of materials. The material of each layer in the organic electroluminescent device is not particularly limited, and other than the benzo five-membered heterocyclic derivative represented by formula (I) of the present invention described above, those known in the art may be used. The materials in the organic functional layers of the above-mentioned organic electroluminescent devices and the electrode materials of the devices are described below:
the anode material is preferably a material having a high work function and having a good light-transmitting property, and includes a metal, a metal oxide, a metal alloy, a combination of a metal and an oxide, a conductive polymer, and the like. Specific examples include: gold, vanadium, chromium, copper, palladium, nickel, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), zinc oxide, indium oxide, tin oxide antimony (SnO)2Sb), polypyrrole, etc., but are not limited thereto.
The hole injection material is preferably a material capable of lowering a hole injection energy barrier, and includes metal oxides, phthalocyanine compounds, arylamine compounds, polycyano-containing conjugated organic materials, high molecular materials, and the like, and specific examples include: molybdenum trioxide (MoO)3) Copper phthalocyanine (CuPc), 4 '-tris (N-3-methylphenyl-N-phenylamino) triphenylamine (m-MTDATA), 4' -tris [ 2-naphthylphenylamino ] amine]Triphenylamine (2T-NATA), 1,4,5,8,9, 11-hexaazabenzonitrile (HAT-C)N), (2E,2'E,2 "E) -2,2', 2" - (cyclopropane-1, 2, 3-triylidene) tris (2- (perfluorophenyl) -acetonitrile), poly (3, 4-ethylenedioxythiophene)/poly (styrenesulfonic acid) (PEDOT/PSS), and the like, but are not limited thereto.
The hole transport material is a compound having a strong electron donating property, and includes aromatic amine compounds, carbazole compounds and the like, and specific examples include: n, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N4, N4, N4', N4' -tetrakis ([1,1' -biphenyl ] -4-yl) - [1,1' -biphenyl ] -4,4' -diamine, 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), 2,7, 7-tetrakis (diphenylamino) -9, 9-spirobifluorene (Spiro-TAD), 4' -tris (carbazol-9-yl) triphenylamine (TCTA), and the like, but is not limited thereto.
The electron blocking material has a function of blocking electrons in the light emitting layer, and includes aromatic amine compounds and the like. Examples of the electron blocking material include: 4,4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), and the like, but is not limited thereto.
The light emitting material has the ability to accept holes and electrons, and includes fluorescent light emitting materials and phosphorescent light emitting materials, and specific examples of the fluorescent light emitting materials include: 9, 10-di (2-naphthyl) Anthracene (ADN), 9, 10-di (1-naphthyl) anthracene (. alpha. -ADN), and the like, but is not limited thereto; specific examples of the phosphorescent light-emitting material include: 4, 4-bis (9-Carbazolyl) Biphenyl (CBP), 9'- (1, 3-phenyl) bis-9H-carbazole (MCP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 1,3, 5-tris (9-carbazolyl) benzene (TCP), and the like, but is not limited thereto.
The hole blocking material has the function of blocking holes in the light emitting layer, and comprises heterocyclic compounds such as imidazole compounds, phenanthroline compounds and the like. In addition to the benzo five-membered heterocycle derivatives of the formula (I) according to the invention, specific examples include: 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BALq), and the like, but is not limited thereto. The benzo five-membered heterocycle derivatives represented by formula (I) of the present invention are preferred.
Electronic transmitterThe material has high electron accepting capacity and high electron transmitting capacity, has the functions of injecting electrons and balancing current carriers, and comprises benzo five-membered heterocyclic derivatives such as pyridine compounds, imidazole compounds, oxadiazole compounds, triazole compounds and phenanthroline compounds, metal complexes and the like. In addition to the benzo five-membered heterocycle derivatives of the formula (I) according to the invention, specific examples include: tris (8-hydroxyquinoline) aluminum (III) (Alq)3) 3,3'- [5' - [3- (3-pyridyl) phenyl](TmPyPB), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (PBD), 3- (biphenyl-4-yl) -4-phenyl-5- (4-tert-butylphenyl) -1,2, 4-Triazole (TAZ), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), and the like, but are not limited thereto. The benzo five-membered heterocycle derivatives represented by formula (I) of the present invention are preferred.
The electron injecting material can improve the injection ability of electrons in the device, and includes inorganic salts of alkali metals, oxides of alkali metals, organic salts of alkali metals, fluorides of alkali metals, complexes of alkali metals, and the like, and specific examples include: cesium carbonate (Cs)2CO3) Lithium oxide (Li)2O), potassium acetate (CH)3COOK), lithium fluoride (LiF), lithium 8-hydroxyquinoline (Liq), and the like, but is not limited thereto.
The cathode material is preferably a material having a low work function so as to allow electrons to be efficiently injected into the organic layer, and includes metals, metal alloys, and the like, and specific examples include: aluminum, silver, magnesium, calcium, magnesium-silver alloy, and the like, but is not limited thereto.
The cover layer material is preferably a material having a high glass transition temperature. In addition to the benzo five-membered heterocycle derivatives of formula (I) of the present invention, capping layer materials that can be used in the present invention include, but are not limited to: thiophenes, furans, pyrroles, pyrenes, anthracenes, and the like. The benzo five-membered heterocycle derivatives of the formula (I) according to the invention are preferred.
The organic electroluminescent device is mainly applied to the technical field of information display, and is widely applied to various information displays in the aspect of information display, such as tablet computers, flat televisions, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable equipment and the like.
Synthetic examples
The method for producing the benzo five-membered heterocycle derivative represented by formula (I) of the present invention is not particularly limited, and conventional methods known to those skilled in the art may be employed. For example, carbon-carbon coupling reaction, etc., the benzo five-membered heterocycle derivative of formula (I) of the present invention can be prepared by the following synthetic route.
Wherein Ar is1、Ar2、L1～L3、R2、X1、Y1～Y4And m and n are the same as defined above, and Xa to Xe are independently any one selected from the group consisting of I, Br and Cl.
The process for preparing the triarylamine compound represented by formula II of the present invention is not particularly limited, and conventional processes well known to those skilled in the art may be employed. For example, carbon-nitrogen coupling reaction, more specifically, a Buchwald reaction, a Ullmann reaction, and the like can be used.
Raw materials and reagents: the raw materials and reagents used in the invention are all pure reagents. The starting materials and reagents used in the following synthetic examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art.
The instrument comprises the following steps: (1) G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk); (2) a Vario EL cube type organic element analyzer (Elementar corporation, germany); (3) model Bruker-510 nuclear magnetic resonance spectrometer (Bruker, germany).
Synthesis example 1: synthesis of Compound 1
Preparation of intermediate 1-1:
the amount of a-1(54.63g,200.00mmol), b-1(31.90g, 204.00mmol), potassium acetate (39.26g, 400.00mmol), Pd (PPh)3)4(4.62g, 4.00mmol) was added to the reaction flask in admixture with 600mL of toluene, 200mL of ethanol, and 200mL of water. Heating and refluxing for reaction for 2 hours under the protection of nitrogen; after the reaction is finished, cooling the reaction mixture to room temperature, performing suction filtration to obtain a filter cake, washing the filter cake with ethanol, and finally recrystallizing the filter cake with toluene/ethanol (7: 2) to obtain an intermediate 1-1(50.60g, yield 83%); the HPLC purity is more than or equal to 99.41 percent; mass spectrum m/z: 304.1001 (theoretical value: 304.1019).
Preparation of intermediates 1-2:
intermediate 1-1(44.38g, 145.60mmol), c-1(40.67g, 160.16mmol), KOAc (42.87g, 436.80mmol), Pd (dppf) Cl2(3.20g, 4.37mmol) and 1, 4-dioxane (700mL) were added to the reaction flask in admixture. Heating and refluxing for 5 hours under the protection of nitrogen; after the reaction was completed, after the reaction mixture was cooled to room temperature, water was added thereto, followed by extraction with ethyl acetate, and the organic layer was over anhydrous MgSO4Drying, rotary evaporation to remove ethyl acetate, recrystallization with toluene and drying gave intermediate 1-2(48.47g, 84% yield); the HPLC purity is more than or equal to 99.50 percent; mass spectrum m/z: 396.2280 (theoretical value: 396.2261).
Preparation of intermediates 1 to 3:
d-1(26.03g, 100.00mmol), intermediate 1-2(40.43g, 102.00mmol), and K2CO3(27.64g，200.00mmol)、Pd(dppf)Cl2(1.46g, 2.00mmol) was mixed with 300mL of toluene, 100mL of ethanol, and 100mL of water and added to the reaction flask. Heating and refluxing for reaction for 3 hours under the protection of nitrogen; after the reaction is finished, cooling the reaction mixture to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (20: 3 recrystallization to give intermediates 1-3(34.18g, 76% yield); the HPLC purity is more than or equal to 99.54 percent; mass spectrum m/z: 448.0539 (theoretical value: 448.0552).
Preparation of intermediates 1 to 4:
intermediates 1-3(29.24g, 65.00mmol), c-1(54.47g, 214.50mmol), KOAc (57.41g, 585.00mmol), Pd (dppf) Cl2(4.28g, 5.85mmol), 1, 4-dioxane (450mL), mixingAnd then added into a reaction bottle. Heating and refluxing for reaction for 7 hours under the protection of nitrogen; after the reaction was completed, after the reaction mixture was cooled to room temperature, water was added thereto, followed by extraction with ethyl acetate, and the organic layer was over anhydrous MgSO4Drying, rotary evaporation to remove ethyl acetate, then recrystallization with toluene, drying to obtain intermediates 1-4(34.37g, 73% yield); the HPLC purity is more than or equal to 99.62 percent; mass spectrum m/z: 724.4293 (theoretical value: 724.4278).
Preparation of compound 1:
intermediates 1-4(28.97g, 40.00mmol), e-1(24.32g, 122.80mmol), Cs2CO3(78.20g，240.00mmol)、Pd2(dba)3(1.10g，1.20mmol)、P(t-Bu)3(1.94g, 9.60mmol) was mixed with 200ml tetrahydrofuran and added to the reaction flask. Heating and refluxing for 5 hours under the protection of nitrogen; after the reaction is finished, cooling the reaction mixture to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally recrystallizing the filter cake with toluene to obtain the compound 1(18.70g, 67% yield) with the HPLC purity of more than or equal to 99.77%. Mass spectrum m/z: 697.2381 (theoretical value: 697.2365). Theoretical element content (%) C48H31N3O3: c, 82.62; h, 4.48; and N, 6.02. Measured elemental content (%): c, 82.58; h, 4.51; and N, 5.97.
Synthesis example 2: synthesis of Compound 3
Compound 3(19.74g) was obtained in the same preparation method as Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-3; the HPLC purity is more than or equal to 99.69 percent. Mass spectrum m/z: 747.2511 (theoretical value: 747.2522). Theoretical element content (%) C52H33N3O3: c, 83.52; h, 4.45; n, 5.62. Measured elemental content (%): c, 83.49; h, 4.50; and N, 5.59.
Synthetic example 3: synthesis of Compound 5
Compound 5(20.04g) was obtained in the same production method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-5, and its HPLC purity was 99.76% or more. Mass spectrum m/z: 747.2507 (theoretical value: 747.2522). Theoretical element content (%) C52H33N3O3: c, 83.52; h, 4.45; n, 5.62. Measured elemental content (%): c, 83.48; h, 4.46; n, 5.67.
Synthetic example 4: synthesis of Compound 15
Compound 15(20.15g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-15, and the HPLC purity was 99.73% or more. Mass spectrum m/z: 774.2644 (theoretical value: 774.2631). Theoretical element content (%) C53H34N4O3: c, 82.15; h, 4.42; and N, 7.23. Measured elemental content (%): c, 82.19; h, 4.37; and N, 7.21.
Synthesis example 5: synthesis of Compound 20
Compound 20(19.37g) was obtained in the same production method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-20, and its HPLC purity was 99.72% or higher. Mass spectrum m/z: 722.2302 (theoretical value: 722.2318). Theoretical element content (%) C49H30N4O3: c, 81.42; h, 4.18; and N, 7.75. Measured elemental content (%): c, 81.37; h, 4.22; and N, 7.70.
Synthetic example 6: synthesis of Compound 25
Compound 25(20.54g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-25, and the HPLC purity was 99.70% or more. Mass spectrum m/z: 789.2977 (theoretical value: 789.2991). Theoretical element content (%) C55H39N3O3: c, 83.63; h, 4.98; n, 5.32. Measured elemental content (%): c, 83.59; h, 4.99; and N, 5.29.
Synthetic example 7: synthesis of Compound 27
Compound 27(20.06g) was obtained in the same production method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-27, and its HPLC purity was 99.76% or more. Mass spectrum m/z: 759.2505 (theoretical value: 759.2522). Theoretical element content (%) C53H33N3O3: c, 83.78; h, 4.38; n, 5.53. Measured elemental content (%): c, 83.82; h, 4.40; and N, 5.49.
Synthesis example 8: synthesis of Compound 36
Compound 36(21.37g) was obtained in the same preparation method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-36, and its HPLC purity was 99.75% or more. Mass spectrum m/z: 821.2696 (theoretical value: 821.2678). Theoretical element content (%) C58H35N3O3: c, 84.76; h, 4.29; n, 5.11. Measured elemental content (%): c, 84.81; h, 4.32; and N, 5.09.
Synthetic example 9: synthesis of Compound 47
Compound 47(21.09g) was obtained in the same production method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-47, and its HPLC purity was 99.74% or higher. Mass spectrum m/z: 823.2567 (theoretical value: 823.2583). Theoretical element content (%) C56H33N5O3: c, 81.64; h, 4.04; and N, 8.50. Measured elemental content (%): c, 81.60; h, 4.07; and N, 8.49.
Synthetic example 10: synthesis of Compound 56
Compound 56(21.40g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-56, and the HPLC purity was 99.65% or more. Mass spectrum m/z: 835.2456 (theoretical value: 835.2471). Theoretical element content (%) C58H33N3O4: c, 83.34; h, 3.98; and N, 5.03. Measured elemental content (%): c, 83.29; h, 4.03; and N, 5.00.
Synthetic example 11: synthesis of Compound 63
Compound 63(21.47g) was obtained in the same production method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-63 and had an HPLC purity of 99.69% or higher. Mass spectrum m/z: 851.2234 (theoretical value: 851.2243). Theoretical element content (%) C58H33N3O3S: c, 81.77; h, 3.90; and N, 4.93. Measured elemental content (%): c, 81.82; h, 3.88; and N, 4.87.
Synthetic example 12: synthesis of Compound 71
Synthesis of example 1Compound 71(22.25g) was obtained in the same preparation method as in Synthesis example 1 except that a-1 in (1) was replaced with equimolar a-71, and the HPLC purity was 99.67% or more. Mass spectrum m/z: 896.2799 (theoretical value: 896.2787). Theoretical element content (%) C63H36N4O3: c, 84.36; h, 4.05; and N, 6.25. Measured elemental content (%): c, 84.41; h, 4.01; and N, 6.28.
Synthetic example 13: synthesis of Compound 83
Compound 83(22.35g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-83, and the HPLC purity was 99.63% or more. Mass spectrum m/z: 886.2931 (theoretical value: 886.2944). Theoretical element content (%) C62H38N4O3: c, 83.95; h, 4.32; and N, 6.32. Measured elemental content (%): c, 83.90; h, 4.34; and N, 6.31.
Synthesis example 14: synthesis of Compound 84
Compound 84(22.23g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-84, and the HPLC purity was 99.59% or more. Mass spectrum m/z: 910.2959 (theoretical value: 910.2944). Theoretical element content (%) C64H38N4O3: c, 84.38; h, 4.20; and N, 6.15. Measured elemental content (%): c, 84.41; h, 4.16; and N, 6.22.
Synthetic example 15: synthesis of Compound 89
Synthesis example 1 was repeated except that a-1 was replaced with equimolar a-89The same preparation as in example 1 gave compound 89(18.27g) with an HPLC purity of 99.79% or more. Mass spectrum m/z: 671.1834 (theoretical value: 671.1845). Theoretical element content (%) C45H25N3O4: c, 80.47; h, 3.75; and N, 6.26. Measured elemental content (%): c, 80.50; h, 3.71; and N, 6.31.
Synthetic example 16: synthesis of Compound 90
Compound 90(18.43g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-90, and its HPLC purity was 99.77% or more. Mass spectrum m/z: 687.1601 (theoretical value: 687.1617). Theoretical element content (%) C45H25N3O3S: c, 78.59; h, 3.66; and N, 6.11. Measured elemental content (%): c, 78.62; h, 3.65; and N, 6.09.
Synthetic example 17: synthesis of Compound 91
Compound 91(19.72g) was obtained in the same production method as in Synthesis example 1 except for replacing a-1 in Synthesis example 1 with equimolar a-91, and its HPLC purity was not less than 99.69%. Mass spectrum m/z: 746.2335 (theoretical value: 746.2318). Theoretical element content (%) C51H30N4O3: c, 82.02; h, 4.05; and N, 7.50. Measured elemental content (%): c, 81.98; h, 4.10; and N, 7.47.
Synthetic example 18: synthesis of Compound 96
Synthesis example 1 was repeated in the same manner as in Synthesis example 1 except that a-1 was replaced with equimolar a-96 and b-1 was replaced with equimolar b-96The preparation of (1) gave compound 96(18.73g) with an HPLC purity of 99.75% or more. Mass spectrum m/z: 698.2330 (theoretical value: 698.2318). Theoretical element content (%) C47H30N4O3: c, 80.79; h, 4.33; and N, 8.02. Measured elemental content (%): c, 80.74; h, 4.40; and N, 7.96.
Synthetic example 19: synthesis of Compound 113
Compound 113(20.09g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-113 and b-1 was replaced with equimolar b-113, and the HPLC purity was 99.67% or more. Mass spectrum m/z: 760.2466 (theoretical value: 760.2474).
Theoretical element content (%) C52H32N4O3: c, 82.09; h, 4.24; and N, 7.36. Measured elemental content (%): c, 82.13; h, 4.19; and N, 7.40.
Synthesis example 20: synthesis of Compound 144
Compound 144(22.12g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-144 and b-1 was replaced with equimolar b-144, and the HPLC purity was 99.68% or higher. Mass spectrum m/z: 863.2886 (theoretical value: 863.2896). Theoretical element content (%) C59H37N5O3: c, 82.02; h, 4.32; n, 8.11. Measured elemental content (%): c, 81.99; h, 4.33; and N, 8.08.
Synthetic example 21: synthesis of Compound 240
B-in Synthesis example 1Compound 240(18.53g) was obtained in the same preparation method as in Synthesis example 1 except that 1 was replaced with equimolar b-240, and its HPLC purity was 99.73% or more. Mass spectrum m/z: 701.2603 (theoretical value: 701.2616). Theoretical element content (%) C48H27D4N3O3: c, 82.15; h, 5.03; and N, 5.99. Measured elemental content (%): c, 82.19; h, 4.98; and N, 6.02.
Synthetic example 22: synthesis of Compound 247
Compound 247(20.48g) with an HPLC purity of 99.69% or more was obtained by the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-247 and b-1 was replaced with equimolar b-247. Mass spectrum m/z: 787.2460 (theoretical value: 787.2471). Theoretical element content (%) C54H33N3O4: c, 82.32; h, 4.22; n, 5.33. Measured elemental content (%): c, 82.28; h, 4.19; and N, 5.29.
Synthetic example 23: synthesis of Compound 256
Compound 256(22.97g) was obtained in the same production method as in Synthesis example 1 except that e-1 in Synthesis example 1 was replaced with equimolar e-256, and the HPLC purity was 99.74% or more. Mass spectrum m/z: 925.3324 (theoretical value: 925.3304). Theoretical element content (%) C66H43N3O3: c, 85.60; h, 4.68; n, 4.54. Measured elemental content (%): c, 85.58; h, 4.72; and N, 4.49.
Synthetic example 24: synthesis of Compound 278
Synthesis of example 1Compound 278(24.14g) was obtained according to the same preparation method as in synthetic example 1 except that a-1 in (b-1) was replaced with equimolar a-278, b-1 was replaced with equimolar b-113, and e-1 was replaced with equimolar e-256, and the HPLC purity was not less than 99.72%. Mass spectrum m/z: 988.3401 (theoretical value: 988.3413). Theoretical element content (%) C70H44N4O3: c, 85.00; h, 4.48; and N, 5.66. Measured elemental content (%): c, 84.97; h, 4.53; n, 5.67.
Synthetic example 25: synthesis of Compound 304
Compound 304(18.50g) was obtained in the same production method as in Synthesis example 1 except for replacing e-1 in Synthesis example 1 with equimolar e-304, and its HPLC purity was 99.74% or more. Mass spectrum m/z: 700.2216 (theoretical value: 700.2223). Theoretical element content (%) C45H28N6O3: c, 77.13; h, 4.03; and N, 11.99. Measured elemental content (%): c, 77.09; h, 3.98; and N, 12.02.
Synthetic example 26: synthesis of Compound 313
Compound 313(20.22g) was obtained in the same preparation method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-313, b-1 was replaced with equimolar b-113, and e-1 was replaced with equimolar e-313, and the HPLC purity was 99.68% or more. Mass spectrum m/z: 777.2472 (theoretical value: 777.2488). Theoretical element content (%) C50H31N7O3: c, 77.21; h, 4.02; and N, 12.61. Measured elemental content (%): c, 77.17; h, 3.99; n, 12.67.
Synthetic example 27: synthesis of Compound 340
Compound 340(21.50g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-340, b-1 was replaced with equimolar b-340 and e-1 was replaced with equimolar e-340, and the HPLC purity was 99.63% or more. Mass spectrum m/z: 839.2945 (theoretical value: 839.2926). Theoretical element content (%) C50H17D10N11O3: c, 71.50; h, 4.44; n, 18.34. Measured elemental content (%): c, 71.47; h, 4.38; n, 18.29.
Synthetic example 28: synthesis of Compound 354
Compound 354(23.11g) was obtained with HPLC purity of 99.68% or more by the same preparation method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-247 and e-1 was replaced with equimolar e-354. Mass spectrum m/z: 931.3011 (theoretical value: 931.3019). Theoretical element content (%) C60H37N9O3: c, 77.32; h, 4.00; n, 13.53. Measured elemental content (%): c, 77.29; h, 3.97; n, 13.49.
Synthetic example 29: synthesis of Compound 364
Compound 364(22.97g) was obtained in the same production method as in Synthesis example 1 except for replacing e-1 in Synthesis example 1 with equimolar e-364, and its HPLC purity was 99.77% or more. Mass spectrum m/z: 925.3320 (theoretical value: 925.3304). Theoretical element content (%) C66H43N3O3: c, 85.60; h, 4.68; n, 4.54. Measured elemental content (%): c, 85.56; h, 4.70; and N, 4.49.
Synthetic example 30: synthesis of Compound 384
Compound 384(18.42g) was obtained with an HPLC purity of 99.75% or more by the same preparation method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-96, b-1 was replaced with equimolar b-384, and d-1 was replaced with equimolar d-384. Mass spectrum m/z: 697.2375 (theoretical value: 697.2365). Theoretical element content (%) C48H31N3O3: c, 82.62; h, 4.48; and N, 6.02. Measured elemental content (%): c, 82.59; h, 4.52; and N, 5.98.
Synthetic example 31: synthesis of Compound 410
Compound 410(21.01g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-278, b-1 was replaced with equimolar b-384, d-1 was replaced with equimolar d-384, and e-1 was replaced with equimolar e-410, and the HPLC purity was 99.73% or more. Mass spectrum m/z: 807.1824 (theoretical value: 807.1837). Theoretical element content (%) C53H33N3S3: c, 78.78; h, 4.12; and N, 5.20. Measured elemental content (%): c, 78.80; h, 4.08; and N, 5.17.
Synthetic example 32: synthesis of Compound 414
Compound 414(22.22g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-247, b-1 was replaced with equimolar b-384, d-1 was replaced with equimolar d-384, and e-1 was replaced with equimolar e-414, and the HPLC purity was 99.70% or more. Mass spectrum m/z: 895.2136 (theoretical value: 895.2150). Theoretical element content (%) C60H37N3S3：C,80.42；H,4.16；N,4.69. Measured elemental content (%): c, 80.37; h, 4.20; and N, 4.72.
Synthetic example 33: synthesis of Compound 437
Compound 437(21.93g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-437, b-1 was replaced with equimolar b-340, and e-1 was replaced with equimolar e-410, and the HPLC purity was 99.68% or more. Mass spectrum m/z: 869.1731 (theoretical value: 869.1742). Theoretical element content (%) C56H31N5S3: c, 77.31; h, 3.59; and N, 8.05. Measured elemental content (%): c, 77.27; h, 3.61; and N, 8.08.
Synthesis example 34: synthesis of Compound 460
Compound 460(24.06g) was obtained in the same production method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-460 and e-1 was replaced with equimolar e-460, and its HPLC purity was not less than 99.62%. Mass spectrum m/z: 985.2817 (theoretical value: 985.2804). Theoretical element content (%) C60H43N9S3: c, 73.07; h, 4.39; n, 12.78. Measured elemental content (%): c, 73.11; h, 4.41; and N, 12.80.
Synthetic example 35: synthesis of Compound 486
Compound 486(23.89g) was obtained with an HPLC purity of 99.68% or more by the same preparation method as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-247, b-1 was replaced with equimolar b-486, and e-1 was replaced with equimolar e-486. Mass spectrum m/z: 978.2363 (Li)Theoretical value: 978.2382). Theoretical element content (%) C61H38N8S3: c, 74.82; h, 3.91; n, 11.44. Measured elemental content (%): c, 74.79; h, 3.88; n, 11.39.
Synthetic example 36: synthesis of Compound 498
Compound 498(22.89g) was obtained in the same production method as in Synthesis example 1 except that e-1 in Synthesis example 1 was replaced with equimolar e-498, and its HPLC purity was 99.73% or more. Mass spectrum m/z: 922.3793 (theoretical value: 922.3784). Theoretical element content (%) C66H46N6: c, 85.87; h, 5.02; and N, 9.10. Measured elemental content (%): c, 85.90; h, 4.97; and N, 9.08.
Device example 1
Firstly, an ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, then the ITO glass substrate is repeatedly cleaned for 2 times, ultrasonic cleaning is carried out for 10 minutes, after the cleaning of the distilled water is finished, isopropanol, acetone and methanol solvents are adopted for carrying out ultrasonic cleaning in sequence, then the ITO glass substrate is dried on a hot plate heated to 120 ℃, the dried substrate is transferred into a plasma cleaning machine, and after 5 minutes of cleaning, the substrate is transferred into an evaporation machine.
Then, HI-1 with the thickness of 50nm is evaporated and plated on the cleaned ITO substrate to be used as a hole injection layer material; evaporating and plating HT-1 with the thickness of 40nm on the hole injection layer to be used as a hole transport layer material; vacuum evaporating a main material RH-1 and a doping material RD-1 on the hole transport layer, forming a luminescent layer by the doping ratio of 96:4, and evaporating to form the luminescent layer with the thickness of 25 nm; evaporating the compound 1 of the invention as a hole blocking layer on the luminescent layer, wherein the evaporation thickness is 10 nm; evaporating ET-1 as an electron transport layer on the hole blocking layer, wherein the evaporation thickness is 35 nm; evaporating LiF as an electron injection layer on the electron transport layer, wherein the evaporation thickness is 0.5 nm; then, Al (110nm) was vapor-deposited on the electron injection layer as a cathode, thereby preparing an organic electroluminescent device.
The compounds involved in the device examples of the invention and the comparative examples are as follows:
device examples 2 to 15
An organic electroluminescent device was produced by the same production method as in device example 1 except that compound 3, compound 15, compound 25, compound 47, compound 56, compound 89, compound 113, compound 144, compound 240, compound 304, compound 354, compound 364, compound 460, and compound 498 of the present invention were used as the hole blocking layer in place of compound 1 in device example 1, respectively.
Comparative device examples 1 to 4
An organic electroluminescent device was produced by the same production method as in device example 1 except that compound 1 in device example 1 was replaced with comparative compound 1, comparative compound 2, and comparative compound 3 as a hole blocking layer.
The driving voltage and the luminous efficiency of the organic electroluminescent device were tested by combining test software, a computer, a K2400 digital source manufactured by Keithley, usa, and a PR788 spectral scanning luminance meter manufactured by Photo Research, usa, into a combined IVL test system. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature. The light emitting characteristics of the devices 1 to 15 in the device examples of the present invention and the organic electroluminescent devices obtained in the comparative examples 1 to 4 were measured, and the results are shown in table 1 below.
Table 1: test of light emission characteristics of organic electroluminescent device
The test results in table 1 show that, compared with the comparative device examples 1 to 3, the benzo five-membered heterocyclic derivative provided by the invention applied to the organic electroluminescent device as the hole blocking layer material can effectively block the holes in the luminescent layer, improve the recombination rate of the holes and electrons, thereby improving the luminous efficiency of the device and prolonging the service life.
Device example 16
Firstly, an ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, then the ITO glass substrate is repeatedly cleaned for 2 times, ultrasonic cleaning is carried out for 10 minutes, after the cleaning of the distilled water is finished, isopropanol, acetone and methanol solvents are adopted for carrying out ultrasonic cleaning in sequence, then the ITO glass substrate is dried on a hot plate heated to 120 ℃, the dried substrate is transferred into a plasma cleaning machine, and after 5 minutes of cleaning, the substrate is transferred into an evaporation machine.
Then, HI-1 with the thickness of 50nm is evaporated and plated on the cleaned ITO substrate to be used as a hole injection layer material; evaporating and plating HT-1 with the thickness of 40nm on the hole injection layer to be used as a hole transport layer material; vacuum evaporating a main material RH-1 and a doping material RD-1 on the hole transport layer, forming a luminescent layer by the doping ratio of 96:4, and evaporating to form the luminescent layer with the thickness of 25 nm; evaporating the compound 5 of the invention on the luminescent layer as an electron transport layer, wherein the evaporation thickness is 35 nm; evaporating LiF as an electron injection layer on the electron transport layer, wherein the evaporation thickness is 0.5 nm; then, Al (110nm) was vapor-deposited on the electron injection layer as a cathode, thereby preparing an organic electroluminescent device.
Device examples 17 to 30
An organic electroluminescent device was produced by the same production method as in device example 16, except that compound 15, compound 20, compound 27, compound 36, compound 71, compound 83, compound 90, compound 96, compound 144, compound 278, compound 304, compound 313, compound 384, and compound 486 of the present invention were used as electron transport layers in place of compound 5 in device example 16, respectively.
Comparative device examples 5 to 8
An organic electroluminescent device was produced by the same production method as that of device example 16 except that compound 5 in device example 16 was replaced with compound 1, compound 2 and compound 3 as an electron transport layer. The test results are shown in table 2 below.
Table 2: test of light emission characteristics of organic electroluminescent device
The test results in table 2 show that the benzo five-membered heterocyclic derivative provided by the invention has better electron transfer efficiency as an electron transport layer material, can effectively improve the injection balance of holes and electrons, and has high luminous efficiency and long service life when applied to an organic electroluminescent device, compared with comparative examples 4 to 6.
Device example 31
Firstly, an ITO/Ag/ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, then the substrate is repeatedly cleaned for 2 times, ultrasonic cleaning is carried out for 10 minutes, after the cleaning of the distilled water is finished, isopropanol, acetone and methanol are adopted for carrying out ultrasonic cleaning in sequence, then the substrate is dried on a hot plate heated to 120 ℃, the dried substrate is transferred into a plasma cleaning machine, and the substrate is transferred into an evaporation machine after 5 minutes of cleaning.
HI-1 with the thickness of 50nm is evaporated on the cleaned ITO/Ag/ITO substrate to be used as a hole injection layer material; evaporating and plating HT-1 with the thickness of 40nm on the hole injection layer to be used as a hole transport layer material; vacuum evaporating a main material RH-1 and a doping material RD-1 on the hole transport layer, forming a luminescent layer by the doping ratio of 96:4, and evaporating to form the luminescent layer with the thickness of 25 nm; evaporating ET-1 as an electron transport layer on the luminescent layer, wherein the evaporation thickness is 35 nm; evaporating LiF as an electron injection layer on the electron transport layer, wherein the evaporation thickness is 1 nm; then, Mg/Ag is evaporated on the electron injection layer to be used as a cathode, the evaporation thickness is 12nm, and finally, the compound 1 is evaporated on the cathode to be used as a covering layer, and the evaporation thickness is 70nm, so that the organic electroluminescent device is prepared.
Device examples 32 to 45
An organic electroluminescent device was produced by the same production method as that of device example 31, except that compound 47, compound 63, compound 71, compound 84, compound 91, compound 247, compound 256, compound 304, compound 313, compound 340, compound 384, compound 410, compound 414, and compound 437 of the present invention were used as capping layers in place of compound 1 in device example 31, respectively.
Comparative device examples 9 to 10
An organic electroluminescent device was produced by the same production method as in device example 31 except that compound 1 in device example 31 was replaced with compound 1 and compound 2 as the capping layer. The test results are shown in table 3 below.
Table 3: test of light emission characteristics of organic electroluminescent device
The test results in table 3 show that the nitrogen-containing heterocyclic derivative provided by the present invention, when applied to an organic electroluminescent device, can effectively improve the light extraction efficiency of the device, thereby improving the light emission efficiency of the device, compared with comparative example 7; in addition, the lifetime of the device can be significantly improved.
The results show that the heterocyclic compound provided by the invention can be used as an electron transport layer material, a hole blocking layer material or a covering layer material when being applied to an organic light-emitting device, shows higher luminous efficiency and longer service life, and is an organic light-emitting material with good performance.
It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.
Claims (10)
1. A benzo five-membered heterocyclic derivative is characterized by having a structure represented by formula (I),
n is selected from 3,4 or 5; ar (Ar)1Independently selected from the structures shown below,
said X1Selected from O, S, NR1Any one of the above;
the R is1Any one selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl and substituted or unsubstituted C6-C30 aryl;
the R is2Any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; m is selected from 0, 1,2,3 or 4, when m is greater than 1, a plurality of R2Two R's which are the same or different from each other, or adjacent to each other2Can be connected into a ring;
said Y is1～Y4Independently selected from N or C;
said L1～L3Independently selected from single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted C3-C30Any one of heteroaryl;
ar is2Is a structure shown in a formula (III),
said X2Selected from O, S, N (R)3)、C(R3R4) One of (1), R3、R4Independently selected from any one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C20 arylamine, or R3、R4Can be connected into a ring;
the R is5、R6Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or two adjacent R5Or R6Can be connected into a ring;
p and q are independently selected from 0, 1,2,3 or 4;
the above-mentioned "substituted or unsubstituted alkyl group", "substituted or unsubstituted cycloalkyl group", "substituted or unsubstituted alkenyl group", "substituted or unsubstituted cycloalkenyl group", "substituted or unsubstituted aryl group", "substituted or unsubstituted heteroaryl group", "substituted or unsubstituted aryloxy group", "substituted or unsubstituted arylthio group", "substituted or unsubstituted arylamine group", "substituted or unsubstituted arylene group", "substituted or unsubstituted heteroarylene group" are each substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, and substituted or unsubstituted C3 to C30 heteroaryl group, when substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other; or when the substituent is plural, adjacent substituents may be linked to form a ring.
2. The benzo five-membered heterocycle derivative according to claim 1, wherein said benzo five-membered heterocycle derivative is selected from any one of the following chemical formulas:
said X1Selected from O, S, NR1Any one of the above;
the R is1Any one selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C20 aryl;
the R is2Any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl; m is selected from 0, 1,2,3 or 4, when m is greater than 1, a plurality of R2Two R's which are the same or different from each other, or adjacent to each other2Can be connected into a ring;
said Y is1～Y4Independently selected from N or C;
said L1～L3Independently selected from any one of single bond, substituted or unsubstituted arylene of C6-C20 and substituted or unsubstituted C3-C20 heteroarylene;
said X2Selected from O, S, N (R)3)、C(R3R4) One of (1), R3、R4Independently selected from substituted or unsubstituted C1-C10 alkyl,Any one of substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C2-C20 cycloalkenyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C6-C20 arylthio, substituted or unsubstituted C6-C20 arylamino, or R3、R4Can be connected into a ring;
the R is5、R6Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, or two adjacent R5Or R6Can be connected into a ring;
and p and q are independently selected from 0, 1,2,3 or 4.
3. The benzo five-membered heterocycle derivative of claim 1, wherein Ar is Ar1Any one selected from the following groups:
4. the benzo five-membered heterocycle derivative of claim 1, wherein Ar is Ar2Any one selected from the following groups:
the R is7、R8、R9、R10、R11Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 cycloalkenyl, substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl, or adjacent two substituents can be connected to form a ring;
a is a1Selected from 0, 1,2,3, 4,5, 6 or 7; a is2Selected from 0, 1,2,3, 4 or 5; a is3Selected from 0, 1,2,3 or 4; a is4Selected from 0, 1,2,3, 4,5, 6, 7 or 8; a is5Selected from 0, 1,2 or 3;
the R isaAnd any one selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C20 aryl.
5. The benzo five-membered heterocycle derivative of claim 1, wherein Ar is Ar2Any one selected from the following groups:
6. benzo five-membered heterocycle derivative according to claim 1, wherein said L is1～L3Independently selected from a single bond or any one of the following groups,
7. the heterocyclic derivative according to claim 1, which is selected from any one of the following structures,
8. an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer contains the benzo five-membered heterocycle derivative according to any one of claims 1 to 7.
9. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, the organic layer comprises a hole blocking layer and/or an electron transporting layer, and the hole blocking layer and/or the electron transporting layer comprises the benzo five-membered heterocycle derivative according to any one of claims 1 to 7.
10. An organic electroluminescent device according to claim 8, wherein the organic layer is located on the side of the cathode facing away from the anode, and the organic layer comprises a capping layer comprising the benzo five-membered heterocycle derivative according to any one of claims 1 to 7.
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