CN117126149A - Heterocyclic compound and organic electroluminescent device thereof - Google Patents
Heterocyclic compound and organic electroluminescent device thereof Download PDFInfo
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- CN117126149A CN117126149A CN202311092184.4A CN202311092184A CN117126149A CN 117126149 A CN117126149 A CN 117126149A CN 202311092184 A CN202311092184 A CN 202311092184A CN 117126149 A CN117126149 A CN 117126149A
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- Prior art keywords
- substituted
- unsubstituted
- ring
- group
- alicyclic
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims description 204
- 125000003118 aryl group Chemical group 0.000 claims description 129
- -1 C25 heterocyclic alkanes Chemical class 0.000 claims description 123
- 239000010410 layer Substances 0.000 claims description 105
- 125000001072 heteroaryl group Chemical group 0.000 claims description 93
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 56
- 229910052805 deuterium Inorganic materials 0.000 claims description 56
- 125000002723 alicyclic group Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 40
- 229910052722 tritium Inorganic materials 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 230000000903 blocking effect Effects 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 16
- 125000005549 heteroarylene group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 abstract description 62
- 238000002360 preparation method Methods 0.000 abstract description 52
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 description 70
- 238000003786 synthesis reaction Methods 0.000 description 70
- 125000004432 carbon atom Chemical group C* 0.000 description 57
- 238000001819 mass spectrum Methods 0.000 description 43
- 238000004128 high performance liquid chromatography Methods 0.000 description 42
- 229940126214 compound 3 Drugs 0.000 description 40
- 239000007787 solid Substances 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 18
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 11
- 239000011777 magnesium Substances 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 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 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 9
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000001544 thienyl group Chemical group 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 8
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 8
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000002883 imidazolyl group Chemical group 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000002971 oxazolyl group Chemical group 0.000 description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 8
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 8
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 8
- 125000003373 pyrazinyl group Chemical group 0.000 description 8
- 125000002098 pyridazinyl group Chemical group 0.000 description 8
- 125000004076 pyridyl group Chemical group 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
- 125000000168 pyrrolyl group Chemical group 0.000 description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 125000000335 thiazolyl group Chemical group 0.000 description 8
- 125000004306 triazinyl group Chemical group 0.000 description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 125000001041 indolyl group Chemical group 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 125000003386 piperidinyl group Chemical group 0.000 description 7
- 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 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000005561 phenanthryl group Chemical group 0.000 description 6
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000001725 pyrenyl group Chemical group 0.000 description 6
- 150000003235 pyrrolidines Chemical class 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 5
- GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 description 5
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229940125773 compound 10 Drugs 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000004431 deuterium atom Chemical group 0.000 description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 5
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 4
- 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
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- BYFGZMCJNACEKR-UHFFFAOYSA-N aluminium(i) oxide Chemical compound [Al]O[Al] BYFGZMCJNACEKR-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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Abstract
The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The heterocyclic compound has good stability and film forming property, has proper triplet state energy level when being applied to an organic electroluminescent device, can effectively reduce driving voltage, improve luminous efficiency of the device and prolong service life of the device, has simple preparation method and easily obtained raw materials, can meet industrial requirements, and has good industrial prospect in the fields of flat panel display, solid-state lighting and the like.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof.
Background
With the continuous updating of electronic devices such as mobile phones and computers in recent years, the requirements and the dependence of people on display are increasing. And organic photoelectric functional materials are attracting attention in the display field because of their excellent properties. The organic light-EmittingDiode, OLED device has the advantages of higher response speed, wider color gamut, lower power consumption and other excellent characteristics compared with the LCD, so that the organic light-EmittingDiode, OLED device has larger advantages and wide application prospect.
The organic electroluminescent device is a multilayer thin film structure belonging to the sandwich type. The most typical organic electroluminescent device generally comprises three organic layers, a hole transport layer HIL, a light emitting layer ELL, and an electron transport layer ETL. In order to further improve the performance parameters such as luminous efficiency, luminous brightness and the like of the device, people continuously perfects the structure of the device and increase material layers with independent functions. I.e. a buffer layer such as an electron injection layer, a hole injection layer, an electron blocking layer, a hole blocking layer, etc. is added inside the electrode.
The electron transport material has poor stability because the electron mobility is far smaller than the hole mobility of the hole transport material, so that electrons and holes cannot be effectively transported to the light-emitting layer, and in addition, because of energy level mismatch, a part of electrons and holes escape to the outside of the light-emitting layer, thereby reducing the light-emitting efficiency of the organic electroluminescent device and increasing the driving voltage. The light-emitting layer is unbalanced in electron and hole migration due to the fact that triplet energy levels of the host and guest materials are not matched, and the efficiency of finally combining to form excitons is low, so that the light-emitting efficiency of the organic electroluminescent device is reduced.
Therefore, development of a host material of a light emitting layer which has high mobility and good stability, a hole blocking material capable of effectively blocking hole emission, and a light emitting layer which makes exciton utilization efficiency higher, so that improvement of various properties of an organic electroluminescent device is a direction that we should study.
Disclosure of Invention
In order to solve the problems, the invention provides a heterocyclic compound and an organic electroluminescent device thereof, and the application of the heterocyclic compound in the organic luminescent device can effectively improve the luminous efficiency of the device and prolong the service life of the device.
Specifically, the invention provides a heterocyclic compound, which has a structure represented by a formula I:
group 1:
wherein the Ar is 1 Any one selected from the formula II and the formula III;
the ring A is selected from any one of the structures in the group 1; * Is a condensed site;
the ring B is selected from any one of C6-C18 aryl;
x is selected from any one of CH and N, and at least one of X is selected from N;
said Y is selected from O, S, N (R) d ) Any one of them;
the Y is 1 、Y 2 Independently selected from O, S, C (R a R b )、N(R c ) Any one of them;
the V is selected from any one of CH and N;
the saidAr 2 Any one selected from the group consisting of aryl groups of formulae II, III, substituted or unsubstituted C6 to C30, heteroaryl groups of substituted or unsubstituted C2 to C30, fused ring groups of substituted or unsubstituted C3 to C30 alicyclic rings and C6 to C30 aromatic rings, fused ring groups of substituted or unsubstituted C1 to C25 heterocyclic alkanes and C6 to C30 aromatic rings, fused ring groups of substituted or unsubstituted C3 to C25 alicyclic rings and C2 to C30 heteroaromatic rings;
The L is selected from any one of a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C30, a substituted or unsubstituted alicyclic ring of C3 to C30 and a fused ring group of an aromatic ring of C6 to C30, a substituted or unsubstituted alicyclic ring of C3 to C25 and a fused ring group of a heteroaromatic ring of C2 to C30, and Ar 1 、Ar 2 、L、R 2 Contains at least one or more deuterium;
the R is 0 、R 1 、R 2 、R 3 、R 4 Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups;
the a 0 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R's are present 0 When two or more R' s 0 Are the same as or different from each other;
the a 1 Selected from 0 or 1;
The a 2 Selected from 0, 1 or 2; when there are two R 2 When two R 2 Are the same as or different from each other;
the a 3 Selected from 0, 1, 2, 3 or 4; when two or more R's are present 3 When two or more R' s 3 Are identical to each otherOr different, or adjacent two R' s 3 Are connected with each other to form a substituted or unsubstituted ring;
the a 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 4 When two or more R' s 4 Are identical or different from each other, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is a 、R b Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R a 、R b Form a substituted or unsubstituted ring;
the R is c Any one selected from the group consisting of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C1-C25 heterocycloalkyl ring and a C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring condensed ring group.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises at least one heterocyclic compound.
The beneficial effects are that:
the invention provides a heterocyclic compound which has higher electron mobility and triplet state energy level, and has good film forming property and thermal stability when being applied to an organic electroluminescent device. When the polymer is used as an electron transport material, the electron mobility can be improved, so that electrons can be effectively transported into the light-emitting layer; when the material is used as a hole blocking material, holes can be prevented from escaping outside the luminescent layer, and the recombination probability of excitons in the luminescent layer is improved; when the light-emitting layer is used as a main body material of the light-emitting layer, the distribution of electrons and holes in the light-emitting layer is balanced, an exciton recombination area is wider, the utilization rate of excitons is improved, the light-emitting efficiency of the device is improved, and the service life of the device is prolonged. Meanwhile, the preparation method of the compound is simple, raw materials are easy to obtain, the industrial requirement can be met, and the compound has good industrialization prospect.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. Modifications of the invention which are obvious to those skilled in the art are intended to fall within the scope of the invention.
In the present specification, "-" means a moiety attached to another substituent. "-" may be attached at any optional position of the attached group/fragment.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed,can indicate-> Can indicate->And so on.
In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring.
For example, the number of the cells to be processed,can indicate-> Can represent Can representAnd so on.
Examples of halogens described herein may include fluorine, chlorine, bromine and iodine.
The term "link-forming ring" as used herein means that two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be an aromatic ring system, an aliphatic ring system or a ring system formed by fusing both, and the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane acene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
"substituted or unsubstituted" as used herein, such as "substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene" means that at least one hydrogen atom on the group is replaced with a substituent. When a plurality of hydrogens are replaced with a plurality of substituents, the plurality of substituents may be the same or different. The substituents represented by the "substituted or unsubstituted" in the above-mentioned "substituted or unsubstituted" may be independently selected from deuterium, tritium, cyano, nitro, amino, halogen atom, substituted or unsubstituted C1 to C12 alkyl group, substituted or unsubstituted C3 to C30 silyl group, substituted or unsubstituted C3 to C12 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C12 alkoxy group, substituted or unsubstituted C1 to C6 alkylthio group, substituted or unsubstituted C1 to C12 alkylamino group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C6 to C30 arylamino group, and the like, but are not limited thereto, or may be linked between adjacent two substituents to form a ring. Preferably deuterium, tritium, cyano, nitro, amino, halogen atoms, C1-C12 alkyl groups, C3-C15 silyl groups, C3-C12 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C1-C12 alkoxy groups, specific examples may include deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trifluoromethyl, trifluoroethyl, tridecylmethyl, methoxy, ethoxy, phenyl, tolyl, mesityl, pentadeuterophenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, perylene, pyrenyl, fluoranthenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, 9' -spirobifluorenyl, carbazoloindolyl, pyrrolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, and the like, but is not limited thereto. Or when the substituent is plural, plural substituents are the same or different from each other; or adjacent substituents may be joined to form a ring.
The alkyl group according to the present invention is a generic term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, and the like, but are not limited thereto.
Cycloalkyl according to the invention is a generic term for monovalent radicals obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, most preferably 5 to 7 carbon atoms. Specific examples may include adamantyl, norbornyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like, but are not limited thereto.
The silyl groups according to the invention may be derived from-SiH 3 The radicals mentioned are indicated; the substituted silyl group according to the present invention may be represented by a group as described in-Si (Rs) (Rs) (Rs), and Rs is hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group as described above Substituted or unsubstituted heteroaryl, etc., but not simultaneously hydrogen, deuterium, tritium; the Rs in Si (Rs) (Rs) (Rs) may be the same or different; preferably having 1 to 30 carbon atoms, preferably having 1 to 25 carbon atoms, more preferably having 3 to 22 carbon atoms, most preferably 3 to 18 carbon atoms, examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethylt-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.
The alicyclic group according to the present invention means a generic term of monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule, and may be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 5 to 10 carbon atoms, most preferably 5 to 7 carbon atoms, and specific examples may include adamantyl, norbornyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.
The heterocycloalkyl group according to the present invention refers to a generic term for groups obtained by substituting one or more carbon atoms in the heterocycloalkyl group with hetero atoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 6 carbon atoms. Specific examples may include, but are not limited to, tetrahydropyrrolyl, piperidinyl, and the like.
Aryl in the present invention refers to the generic term for monovalent radicals obtained by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetrabiphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, and the like, but are not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, and specific examples may include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirofluorenyl, spirobifluorenyl, and the like.
Heteroaryl according to the present invention refers to the generic term for groups obtained after substitution of one or more aromatic nucleus carbon atoms in the aryl group with heteroatoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group. Specific examples of the monocyclic heteroaryl group may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, and the like; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused ring heteroaryl group may include, but are not limited to, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorene oxaanthracenyl, spirofluorene thianthrenyl, and the like.
The fused ring group of the alicyclic ring and the aromatic ring refers to the generic term of monovalent groups obtained by removing one hydrogen atom after the alicyclic ring and the aromatic ring are fused together. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, specific examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The fused ring group of the heterocycloalkyl ring and the aromatic ring in the present invention refers to a generic term for monovalent groups obtained by fusing the heterocycloalkyl ring and the aromatic ring together and then removing one hydrogen atom. Preferably having 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, specific examples may include benzoazetidinyl, benzotetrahydropyranyl, benzopiperidinyl, benzoazepanyl, naphthasprings tetrahydropyranyl, naphthasprings piperidinyl, phenanthrlocks piperidinyl, and the like, but are not limited thereto.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the generic term of monovalent groups obtained by fusing the alicyclic ring and the heteroaromatic ring together and removing one hydrogen atom. Preferably having 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, specific examples may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzcycloheptyl, dibenzofuran-cyclopropyl, dibenzofuran-cyclobutyl, dibenzofuran-cyclopentyl, dibenzofuran-cyclohexyl, dibenzofuran-cycloheptyl, dibenzothiophene-cyclopropyl, dibenzothiophene-cyclobutyl, dibenzothiophene-cyclopentyl, dibenzothiophene-cyclohexyl, dibenzothiophene-cycloheptyl, carbazolocyclopropyl, carbazolocyclobutyl, carbazolocyclopentyl, carbazolocyclohexyl, carbazolocycloheptyl, and the like, but are not limited thereto.
The alicyclic group according to the present invention means a generic term for divalent groups obtained by removing two hydrogen atoms from an alicyclic hydrocarbon molecule, and may be a cycloalkylene group, a cycloalkenylene group, or the like, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms, and specific examples may include, but are not limited to, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, an adamantylene group, a norbornylene group, a cyclopropylene group, a cyclobutenyl group, a cyclopentylene group, a cyclohexenylene group, a cycloheptylene group, or the like.
The arylene group according to the present invention means a generic term for divalent groups obtained by removing two hydrogen atoms from an aromatic nucleus of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, and specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, pyrenylene, triphenylene, perylene, fluorenylene, fluoranthrylene, phenylenedenyl, and the like, but are not limited thereto.
Heteroaryl, as used herein, refers to the generic term for groups obtained after substitution of one or more of the aromatic nucleus carbons in the arylene group with heteroatoms, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, the heteroarylene group may be attached to a ring-forming carbon atom or to a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group or a condensed ring heteroarylene group. Specific examples of the monocyclic and condensed ring heteroarylene groups may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, a carbazolylene group, a benzofuranylene group, a benzothienyl group, a benzocarbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzocarbazolylene group, and the like; specific examples of the polycyclic heteroarylene group may include bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but are not limited thereto.
The term "fused ring-sub group" of an alicyclic ring and an aromatic ring as used herein refers to a generic term for divalent groups obtained by fusing an alicyclic ring and an aromatic ring together and then removing two hydrogen atoms. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, specific examples may include benzobicyclopropyl, benzobicyclobutyl, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, benzocyclopentylene, benzocyclohexenylene, benzocycloheptylene, naphthocyclopropyl, naphthocyclobutylene, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The term "fused ring-sub-group" as used herein refers to a generic term for divalent radicals obtained by fusing an alicyclic ring to a heteroaromatic ring and then removing two hydrogen atoms. Preferably having 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, specific examples may include pyrido-cyclopropyl-, pyrido-cyclobutyl-, pyrido-cyclopentyl-, pyrido-cyclohexyl-, pyrido-benzoheptyl-, pyrimido-cyclopropyl-, pyrimido-cyclobutyl-, pyrimido-cyclopentyl-, pyrimido-cyclohexyl-, pyrimido-benzocycloheptyl-, dibenzofuran-cyclopropyl-, dibenzofuran-cyclobutyl-, dibenzofuran-benzocyclopentyl-, dibenzofuran-benzocyclohexyl-, dibenzofuran-benzocycloheptyl-, dibenzothiophene-benzocyclohexyl-, dibenzothiophene-benzocycloheptyl-, carbazolo-cyclopropyl-, carbazolo-and carbazolo-cycloheptyl-, and the like, but are not limited thereto.
The term "at least one", "one or more" as used herein includes one, two, three, four, five, six, seven, eight or more, where permitted.
The invention provides a heterocyclic compound, which has a structure represented by a formula I:
group 1:
wherein the Ar is 1 Any one selected from the formula II and the formula III;
the ring A is selected from any one of the structures in the group 1; * Is a condensed site;
the ring B is selected from any one of C6-C18 aryl;
x is selected from any one of CH and N, and at least one of X is selected from N;
said Y is selected from O, S, N (R) d ) Any one of them;
the Y is 1 、Y 2 Independently selected from O, S, C (R a R b )、N(R c ) Any one of them;
the V is selected from any one of CH and N;
the Ar is as follows 2 Any one selected from the group consisting of aryl groups of formulae II, III, substituted or unsubstituted C6 to C30, heteroaryl groups of substituted or unsubstituted C2 to C30, fused ring groups of substituted or unsubstituted C3 to C30 alicyclic rings and C6 to C30 aromatic rings, fused ring groups of substituted or unsubstituted C1 to C25 heterocyclic alkanes and C6 to C30 aromatic rings, fused ring groups of substituted or unsubstituted C3 to C25 alicyclic rings and C2 to C30 heteroaromatic rings;
the L is selected from any one of a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C30, a substituted or unsubstituted alicyclic ring of C3 to C30 and a fused ring group of an aromatic ring of C6 to C30, a substituted or unsubstituted alicyclic ring of C3 to C25 and a fused ring group of a heteroaromatic ring of C2 to C30, and Ar 1 、Ar 2 、L、R 2 Contains at least one or more deuterium;
the R is 0 、R 1 、R 2 、R 3 、R 4 Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, takenAny one of substituted or unsubstituted cycloalkyl of C3 to C25, substituted or unsubstituted aryl of C6 to C20, substituted or unsubstituted heteroaryl of C2 to C30, substituted or unsubstituted alicyclic of C3 to C30 and condensed cyclic groups of aromatic rings of C6 to C30, substituted or unsubstituted heterocycloalkyl of C1 to C25 and condensed cyclic groups of aromatic rings of C6 to C30, substituted or unsubstituted alicyclic of C3 to C25 and condensed cyclic groups of heteroaromatic rings of C2 to C30;
the a 0 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R's are present 0 When two or more R' s 0 Are the same as or different from each other;
the a 1 Selected from 0 or 1;
the a 2 Selected from 0, 1 or 2; when there are two R 2 When two R 2 Are the same as or different from each other;
the a 3 Selected from 0, 1, 2, 3 or 4; when two or more R's are present 3 When two or more R' s 3 Are identical or different from each other, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
the a 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 4 When two or more R' s 4 Are identical or different from each other, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is a 、R b Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R a 、R b Is connected with each other to form a sampling deviceSubstituted or unsubstituted ring;
the R is c Any one selected from the group consisting of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C1-C25 heterocycloalkyl ring and a C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring condensed ring group.
Preferably, said R 0 、R 1 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthacenecyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthacenecyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthacenecyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthacenecyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylene, unsubstituted phenyl, unsubstituted tri-or unsubstituted phenylsilyl, tri-or unsubstituted phenyl, tri-substituted or unsubstituted phenylsilyl, tri-or unsubstituted phenyl, unsubstituted or unsubstituted phenylyl, substituted or unsubstituted phenylcyclopropyl, substituted or unsubstituted naphthacene A perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzobenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted benzoxazolyl group substituted or unsubstituted dibenzoxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridine, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, any one of substituted or unsubstituted spirofluorene-thioxanthoyl and substituted or unsubstituted spirofluorene-thioxanthoyl.
Preferably, the heterocyclic compound is selected from any one of the following structures:
the R is p 、R q 、R r Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups;
said g 1 Selected from 0, 1, 2, 3, 4, 5 or 6; said g 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 3 Selected from 0, 1, 2, 3, 4 or 5; said g 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present q When two or more R' s q Are identical or different from each other, or adjacent two R q Are connected with each other to form a substituted or unsubstituted ring;
the h is 1 Selected from 0, 1, 2, 3 or 4; when two or more R's are present r When two or more R' s r Are identical or different from each other, or adjacent two R r Are linked to each other to form a substituted or unsubstituted ring.
Preferably, said R p 、R q 、R r Each independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentylUnsubstituted benzocyclopentyl, substituted or unsubstituted naphthacyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthacyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzodibenzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl A substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted spirofluorene xanthenyl group, a substituted or unsubstituted spirofluorene thioxanthenyl group.
More preferably, the heterocyclic compound is selected from any one of the following structures:
preferably, 0V in each structure of said group 1 and derived from group 1 is selected from the group consisting of N atoms, or 1V in each structure of said group 1 and derived from group 1 is selected from the group consisting of N atoms, or two V in each structure of said group 1 and derived from group 1 is selected from the group consisting of N atoms.
Preferably, the saidSelected from any one of the following structures:
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preferably, the formula II is selected from any one of the following structures:
the R is 9 Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
Said f 1 Selected from 1, 2, 3, 4 or 5; said f 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said f 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said f 4 Selected from 1 or 2; said f 5 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said f 6 Selected from 1, 2, 3 or 4; said f 7 Selected from 1, 2 or 3; when two or more R's are present 9 When two or more R' s 9 Are identical or different from each other, or adjacent two R 9 Are linked to each other to form a substituted or unsubstituted ring.
Preferably, said R 9 Selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, Substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridinyl substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthroline group Any one of substituted naphthyridinyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted spirofluorene oxaanthryl, substituted or unsubstituted spirofluorene thiaanthryl.
In one embodiment, R in each structure 9 Is selected from deuterium.
Preferably, R in each structure 9 Is not hydrogen.
Preferably, R in each structure 9 Are all selected from deuterium.
Preferably, the formula III is selected from any one of the following structures:
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the R is 5 Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
said b 1 Selected from 1, 2, 3, 4 or 5; said b 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said b 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 4 Selected from 1 or 2; said b 5 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said b 6 Selected from 1, 2, 3 or 4; said b 7 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b 8 Selected from 1, 2, 3, 4, 5 or 6; said b 9 Selected from 1, 2 or 3; when two or more R's are present 5 When two or more R' s 5 Are identical or different from each other, or adjacent two R 5 Are linked to each other to form a substituted or unsubstituted ring.
Preferably, said R 5 Ra, rb are independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthacene cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthacene cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthacene cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthacene cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted benzocyclol, substituted or unsubstituted trimethylsilyl, unsubstituted or unsubstituted phenyl, substituted or unsubstituted benzotriazolyl, unsubstituted fluorenyl, unsubstituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, trisubstituted or unsubstituted fluorenyl, substituted or unsubstituted benzoguanyl, substituted or unsubstituted phenyl, unsubstituted or unsubstituted three-substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylo-or unsubstituted fluorenyl, substituted or unsubstituted benzoguanyl, substituted or unsubstituted, substituted or unsubstituted pioglitazone A pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzodibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted dibenzooxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group a substituted or unsubstituted dibenzothiazyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted dibenzoimidazolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted spirofluorene oxaanthryl group, or a substituted or unsubstituted spirofluorene thiaanthryl group.
Preferably, said R c Selected from the group consisting of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, and takenSubstituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl A quinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted spirofluorenoxaanthryl group, a substituted or unsubstituted spirofluorenylthioanthryl group.
In one embodiment, R in each structure 5 Is selected from deuterium.
Preferably, R in each structure 5 Is not hydrogen.
Preferably, R in each structure 5 Are all selected from deuterium.
Preferably, the Ar 2 When the structural formula is not represented by the formulas II and III, the structural formula is selected from any one of the following structures:
the R is 6 The same or different is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 condensed ring groups of aromatic rings, substituted or unsubstituted C3-C25 alicyclic and C2-C30 condensed ring groups of heteroaromatic rings;
The c 1 Selected from 0, 1, 2, 3, 4 or 5; the c 2 Selected from 0, 1, 2, 3 or 4; the c 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c 5 Selected from 0, 1 or 2; the c 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the c 7 Selected from 0, 1, 2 or 3; when two or more R's are present 6 When two or more R' s 6 Are identical or different from each other, or adjacent two R 6 Are connected with each other to form a substituted or unsubstituted ring;
the R is d Independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
z is selected from any one of CH and N;
the Y is 4 、Y 5 Each independently selected from O, S, C (R) e R f )、N(R g ) Any one of them;
the R is e 、R f Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R e 、R f Form a substituted or unsubstituted ring;
the R is g Selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and combinations thereof,Any one of a substituted or unsubstituted alicyclic ring of C3 to C30 and a condensed ring group of an aromatic ring of C6 to C30, a substituted or unsubstituted heterocyclic alkane of C1 to C25 and a condensed ring group of an aromatic ring of C6 to C30, a substituted or unsubstituted alicyclic ring of C3 to C25 and a condensed ring group of a heteroaromatic ring of C2 to C30.
Still preferably, the Ar 2 When the structural formula is not represented by the formulas II and III, the structural formula is selected from any one of the following structures:
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the R is 8 The same or different is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 condensed ring groups of aromatic rings, substituted or unsubstituted C3-C25 alicyclic and C2-C30 condensed ring groups of heteroaromatic rings;
Said e 1 Selected from 0, 1, 2, 3, 4 or 5; said e 2 Selected from 0, 1, 2, 3 or 4; said e 3 Selected from 0, 1, 2 or 3; said e 4 Selected from 0, 1 or 2; said e 5 Selected from 0 or 1; said e 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said e 7 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said e 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said e 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 12 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; said e 13 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; said e 14 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; said e 15 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 8 When two or more R' s 8 Are identical or different from each other, or adjacent two R 8 Are connected with each other to form a substituted or unsubstituted ring;
the R is m 、R n Each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups.
Preferably, said R 8 Selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstitutedOr an unsubstituted cycloheptyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted tetrahydropyrrole group, a substituted or unsubstituted piperidyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triethylsilyl group, a substituted or unsubstituted triisopropylsilyl group, a substituted or unsubstituted tri-tert-butylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodithioenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzimidazolyl, substituted or unsubstituted quinolinyl substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzene And any one of a quinoxalinyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted acridine group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted spirofluorenoxaanthryl group, and a substituted or unsubstituted spirofluorenthioanthryl group.
In one embodiment, R in each structure 8 Is selected from deuterium.
Preferably, R in each structure 8 Is not hydrogen.
Preferably, R in each structure 8 Are all selected from deuterium.
Preferably, L is selected from a single bond or from any one of the following structures:
the R is 7 Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups;
Said d 1 Selected from 0, 1, 2, 3 or 4; said d 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 4 Selected from 0, 1 or 2; said d 5 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present 7 When two or more R' s 7 Are identical or different from each other, or adjacent two R 7 Are connected with each other to form a substituted or unsubstituted ring;
the L is 1 Any one selected from a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C30, a substituted or unsubstituted alicyclic ring of C3 to C30 and a fused ring-back group of an aromatic ring of C6 to C30, a substituted or unsubstituted alicyclic ring of C3 to C25 and a fused ring-back group of a heteroaromatic ring of C2 to C30;
the J is selected from any one of CH and N;
the R is h Any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the Y is 6 、Y 7 、Y 8 Is independently selected from O, S, C (R) i R j )、N(R k ) Any one of them;
The R is i 、R j Each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R i 、R j Form a substituted or unsubstituted ring;
the R is k Selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring groupsAny one of a ring-closing group, a substituted or unsubstituted C3-C25 alicyclic ring and a condensed ring group of a C2-C30 heteroaromatic ring.
Still more preferably, L is selected from a single bond or from any one of the following structures:
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preferably Ar 1 、Ar 2 At least one of L is selected from those containing deuterium in the foregoing groups.
More preferably, ar 1 Selected from those containing deuterium in the foregoing groups.
More preferably, ar 2 Selected from those containing deuterium in the foregoing groups.
More preferably, L is selected from those containing deuterium in the aforementioned groups.
Preferably, R 2 Are all selected from deuterium.
Preferably, the compounds of the present invention contain at least one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, said Ar 1 、Ar 2 At least one of L is one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twoThirteen, twenty-four or twenty-five deuterium atoms.
Preferably, said Ar 1 Substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, said Ar 2 Substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Preferably, said L is substituted with one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty-one, twenty-two, twenty-three, twenty-four or twenty-five deuterium atoms.
Most preferably, the compound of formula I is selected from any one of the following structures:
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The heterocyclic compounds of formula I of the present invention are shown in the above list of specific structural forms, but the present invention is not limited to the listed chemical structures, and substituents are included in the structures of formula I.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises at least one heterocyclic compound.
Preferably, the organic layer comprises at least one of an electron transport layer and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer comprises at least one of the heterocyclic compounds according to the present invention.
Preferably, the organic layer comprises a light-emitting layer comprising at least one of the heterocyclic compounds described in the present invention.
Still preferably, the organic layer comprises an electron transport layer comprising at least one of the heterocyclic compounds described herein.
Still preferably, the organic layer comprises a hole blocking layer comprising at least one of the heterocyclic compounds described herein.
The material of each layer of thin film in the organic electroluminescent device is not particularly limited, and materials known in the art can be used. The following describes each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device, respectively:
the anode material of the present invention is preferably a material having a high work function in order to improve hole injection efficiency. The anode may be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2 ) Zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single-layer structure or a multi-layer structure including two or more layers, for example, the anode may have a single-layer structure of Al or a three-layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.
The cathode material according to the present invention, preferably a material having a low work function, in order to improve electron injection efficiency, may be selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, a compound including the same, or a mixture thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.
The hole injection layer material disclosed by the invention is preferably a material with better hole injection capability and has more proper HOMO energy level so as to reduce the interface potential barrier between the anode and the hole transport layer and improve the hole injection capability. The hole injection layer material may include metalloporphyrin, oligothiophene, anthraquinone-based compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene-based compounds, quinacridone-based compounds, anthraquinone-based compounds, and polyaniline-based and polythiophene-based conductive polymers, etc., but is not limited thereto.
The hole transport layer material according to the present invention is preferably a material having high hole mobility for hole injection, and may include, but is not limited to, biphenyldiamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, and the like.
The electron blocking layer material of the present invention is preferably a material having a good hole transporting ability and an electron blocking ability so as to efficiently transport holes and limit the escape of electrons to the light emitting layer interface. The electron blocking layer material can be selected from aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include N, N-bis ([ 1,1' -biphenyl ] -4-yl) - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-amine, N- (4 ' - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-N- ([ 1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine, N ' -bis (naphthalen-1-yl) -N, N ' -diphenyl-benzidine (NPD), and the like, but are not limited thereto.
The light-emitting layer material of the present invention may use red, green or blue light-emitting materials, and generally comprises a host material (also referred to as a host material) and a doped material (also referred to as a guest material), and the light-emitting layer material may comprise a plurality of host materials and a plurality of doped materials, and the guest material may be a simple fluorescent material or a phosphorescent material, or may be formed by combining fluorescent and phosphorescent materials. The host material of the light-emitting layer is required to have a bipolar charge transport property and an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material, and may contain anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, and the like, and heterocyclic ring-containing compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, distyrylaryl derivatives, stilbene derivatives, and the like, in addition to the heterocyclic compounds provided by the present invention, but is not limited thereto. The guest material may comprise: metal complexes (for example, iridium complex, platinum complex, osmium complex, rhodium complex, terbium complex, europium complex, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., but are not limited thereto.
The hole blocking layer of the present invention is preferably a material having a good electron transporting ability and a hole blocking ability so as to efficiently transport electrons and limit the escape of holes to the light emitting layer interface. The hole blocking layer material can be selected from metal complexes, quinoline derivatives, imidazole derivatives, phenanthrene derivatives, triazole derivatives, azabenzene derivatives and the like, and preferably at least one of the heterocyclic compounds according to the invention. Specific examples may include bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 3' - [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 "-terphenyl ] -3,3" -diyl ] bipyridine (TmPyPB), and the like, but are not limited thereto.
The electron transport layer material according to the present invention is preferably a material having high electron mobility for electron injection, and may include any one or more of the heterocyclic compounds according to the present invention or the following structures, thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxaoxazole derivatives, azabenzene derivatives, diazene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, and the like, but is not limited thereto.
The electron injection layer material of the present invention is preferably a material having a good electron injection capability and a suitable LUMO energy level so as to reduce an interface barrier between the cathode and the electron transport layer and improve the electron injection capability, and may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances having high electron injection capability. Specific examples may include: li, ca, sr, liF, csF, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 、Al2O 3 、MoO 3 、MgF 2 LiOx, yb, tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, and the like, but is not limited thereto.
The cover layer material of the present invention, preferably a material having a high refractive index in order to improve light extraction efficiency, may include: tris (8-hydroxyquinoline) aluminum (Alq) 3 ) N, N '-bis (naphthalen-1-yl) -N, N' -bis (phenyl) -2,2 '-dimethylbenzidine (NPD), 4' -bis (9-Carbazole) Biphenyl (CBP), and the like, but are not limited thereto.
The method for producing the thin films of each layer in the organic electroluminescent device of the present invention is not particularly limited, and vacuum deposition, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.
The organic electroluminescent device is mainly applied to the technical field of information display and the field of illumination, and is widely applied to various information displays in the aspect of information display, such as mobile phones, tablet computers, flat televisions, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices and the like.
The following is one preparation method of the compound represented by the formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of formula I may be prepared by the reaction scheme shown below, substituents may be bonded through methods known in the art, and the kind and position of substituents or the number of substituents may be changed according to techniques known in the art.
[ synthetic route ]
Preparation of the compound of formula I:
the source of the raw materials used in the present invention is not particularly limited and may be commercially available products or prepared by a preparation method well known to those skilled in the art, for example, the intermediate d may be prepared by the following synthetic route:
preparation of intermediate d:
xa, xb, xc, xd, xe, xf are independently selected from any one of Cl, br and I; the ring A, ar 1 、Ar 2 、L、X、Y、R 0 、R 1 、R 2 、a 0 、a 1 、a 2 The definition of (2) is the same as the definition described above.
Description of the starting materials, reagents and characterization equipment:
The raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis was carried out using a VarioELcube organic elemental analyzer from Elementar, germany, and the sample mass was 5-10 mg.
Synthesis example 1: preparation of Compound 3
Preparation of A-3:
to magnesium (4.08 g,168 mmol) was added two pieces of iodine under nitrogen protection, 50mL of anhydrous tetrahydrofuran solvent was further added, then a tetrahydrofuran solution (100 mL) of b-3 (31.52 g,160 mmol) was slowly added dropwise, the reaction was initiated in a format, after the completion of the dropwise addition, the reaction was carried out at room temperature for 7 hours, and after the completion of the reaction, the mixture was cooled to room temperature.
Under the protection of nitrogen, a-3 (29.50 g,160 mmol) is added into a reaction bottle, then 200mL of tetrahydrofuran solvent is added, the system temperature is reduced to minus 5 ℃, then the format reagent prepared in the step 1 is slowly dripped for 2-3 hours, the reaction is carried out for 6 hours at minus 5 ℃ after the dripping is finished, the reaction liquid is poured into 12% dilute hydrochloric acid after the reaction is finished, after the reaction is fully stirred for 30 minutes, dichloromethane is used for extraction (300 mL multiplied by 3 times), the organic phase is separated, the organic phase is dried by anhydrous magnesium sulfate, the solvent is concentrated by vacuum distillation, and the solvent is recrystallized by tetrahydrofuran after suction filtration, thus obtaining an intermediate A-3 (33.21 g, yield 78%) with HPLC purity of not less than 99.75 percent. Mass spectrum m/z:264.9828 (theory: 264.9810).
Preparation of B-3:
to the reaction flask was added intermediate A-3 (23.42 g,88 mmol), c-3 (10.16 g,80 mmol), anhydrous potassium carbonate (22.11 g,160 mmol) under nitrogen protection, then 200mL of toluene solution was added, and after 3 times of air replacement with nitrogen, tetrakis (triphenylphosphine) palladium (0.92 g,0.8 mmol) was added and the reaction was stirred and heated for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the solvent was concentrated by distillation under reduced pressure, the filter cake was then washed with ethanol, and the obtained filter cake was recrystallized from toluene to give intermediate B-3 (18.77 g, yield 75%) with HPLC purity ≡ 99.85%. Mass spectrum m/z:312.0839 (theory: 312.0826).
Preparation of compound 3:
b-3 (12.51 g,40 mmol), d-3 (13.57 g,40 mmol), potassium carbonate (11.06 g,80 mmol) and then 150mL of toluene/ethanol/water mixed solvent (toluene: ethanol: water volume ratio=2:1:1) were added under nitrogen protection, palladium acetate (0.18 g,0.8 mmol) was then added after 3 times of nitrogen replacement, xphos (0.76 g,1.6 mmol) was then added, after the reaction was completed, the reaction was cooled to room temperature, distilled water was added, the mixture was left to stand for liquid separation, the separated organic phase was concentrated by distillation under reduced pressure, the solvent was suction filtered, the filter cake was washed with ethanol and distilled water, and the obtained filter cake was recrystallized with toluene to give compound 3 (16.46 g, 72%) with HPLC purity > 99.99%, mass spectrum m/z:571.2043 (theory: 571.2057). Theoretical element content (%) C 38 H 17 D 5 N 4 O 2 : c,79.84; h,4.76; n,9.80. Measured element content (%): c,79.87; h,4.74; n,9.82.
Synthesis example 2: preparation of Compound 4
According to the same production method as that of Compound 3 in Synthesis example 1, d-3 was replaced with equimolar d-4, and the other steps were the same, to obtain Compound 4 (16.69 g), and the purity of the solid was not less than 99.98% as measured by HPLC.Mass spectrum m/z:571.2041 (theory: 571.2057). Theoretical element content (%) C 38 H 17 D 5 N 4 O 2 : c,79.84; h,4.76; n,9.80. Measured element content (%): c,79.85; h,4.73; n,9.84.
Synthesis example 3: preparation of Compound 10
According to the same production method as that of Compound 3 in Synthesis example 1, c-3 was replaced with equimolar c-10, and the other steps were the same, to obtain Compound 10 (17.99 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:651.2635 (theory: 651.2621). Theoretical element content (%) C 44 H 17 D 9 N 4 O 2 : c,81.08; h,5.41; n,8.60. Measured element content (%): c,81.05; h,5.42; n,8.63.
Synthesis example 4: preparation of Compound 28
According to the same production method as that of Compound 3 in Synthesis example 1, c-3 and d-3 were replaced with equimolar amounts of c-28 and d-28, respectively, and the other steps were the same, to give Compound 28 (18.41 g), and the purity of the solid as measured by HPLC was not less than 99.95%. Mass spectrum m/z:676.2586 (theory: 676.2573). Theoretical element content (%) C 45 H 16 D 9 N 5 O 2 : c,79.86; h,5.06; n,10.35. Measured element content (%): c,79.82; h,5.05; n,10.37.
Synthesis example 5: preparation of Compound 93
According to the same production method as that of compound 3 in Synthesis example 1, b-3 was replaced with equimolar one respectivelyb-93, other steps are the same, and the compound 93 (16.93 g) is obtained, and the purity of the solid detected by HPLC is more than or equal to 99.99%. Mass spectrum m/z:587.1811 (theory: 587.1828). Theoretical element content (%) C 38 H 17 D 5 N 4 OS: c,77.66; h,4.63; n,9.53. Measured element content (%): c,77.68; h,4.64; n,9.52.
Synthesis example 6: preparation of Compound 100
According to the same manner as in Compound 3 of Synthesis example 1, A-3, c-3 and d-3 were replaced with equimolar amounts of A-93, c-100 and d-4, respectively, and the other steps were the same, to obtain Compound 100 (19.10 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:712.2249 (theory: 712.2235). Theoretical element content (%) C 48 H 24 D 4 N 4 OS: c,80.87; h,4.52; n,7.86. Measured element content (%): c,80.85; h,4.53; n,7.83.
Synthesis example 7: preparation of Compound 102
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3, c-3 and d-3 were replaced with equimolar amounts of b-102, c-102 and d-4, respectively, compound 102 (18.82 g) was obtained, and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:691.2381 (theory: 691.2392). Theoretical element content (%) C 46 H 17 D 9 N 4 OS: c,79.86; h,5.10; n,8.10. Measured element content (%): c,79.85; h,5.13; n,8.13.
Synthesis example 8: preparation of Compound 138
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 was replaced with b-138 in equimolar amounts, and the other steps were the same, to obtain Compound 138 (17.66 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:621.2226 (theory: 621.2213). Theoretical element content (%) C 42 H 19 D 5 N 4 O 2 : c,81.14; h,4.70; n,9.01. Measured element content (%): c,81.11; h,4.74; n,9.02.
Synthesis example 9: preparation of Compound 144
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 and c-3 were replaced with b-144 and c-144, respectively, the procedure was otherwise the same, to give Compound 144 (17.49 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z:633.2232 (theory: 633.2244). Theoretical element content (%) C 43 H 23 D 3 N 4 O 2 : c,81.50; h,4.61; n,8.84. Measured element content (%): c,81.53; h,4.62; n,8.82.
Synthesis example 10: preparation of Compound 147
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 was replaced with b-147 in equimolar amounts, compound 147 (17.41 g) was obtained in the same manner as in the other steps, and the purity of the solid was not less than 99.97% as measured by HPLC. Mass spectrum m/z:621.2227 (theory: 621.2213). Theoretical element content (%) C 42 H 19 D 5 N 4 O 2 : c,81.14; h,4.70; n,9.01. Measured element content (%): c,81.16; h,4.73; n,9.02.
Synthesis example 11: preparation of Compound 151
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 was replaced with b-151 in equimolar amounts, compound 151 (17.66 g) was obtained in the same manner as in the other steps, and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:621.2229 (theory: 621.2213). Theoretical element content (%) C 42 H 19 D 5 N 4 O 2 : c,81.14; h,4.70; n,9.01. Measured element content (%): c,81.16; h,4.71; n,9.02.
Synthesis example 12: preparation of Compound 155
According to the same manner as in Compound 3 of Synthesis example 1, A-3 and c-3 were replaced with equimolar A-151 and c-155, respectively, and the other steps were the same, to obtain Compound 155 (18.95 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:696.2474 (theory: 696.2463). Theoretical element content (%) C 48 H 24 D 4 N 4 O 2 : c,82.74; h,4.63; n,8.04. Measured element content (%): c,82.75; h,4.66; n,8.03.
Synthesis example 13: preparation of Compound 159
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 and c-3 were replaced with b-159 and c-159 in equimolar amounts, respectively, and the other steps were the same, to obtain Compound 159 (17.21 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:623.2325 (theory: 623.2339). Theoretical element content (%) C 42 H 17 D 7 N 4 O 2 : c,80.88; h,5.01; n,8.98. Measured element content (%): c,80.85; h,5.03; n,8.96.
Synthesis example 14: preparation of Compound 161
According to the same manner as in Compound 3 of Synthesis example 1, A-3 and c-3 were replaced with equimolar amounts of A-159 and c-161, respectively, and the other steps were the same, to obtain Compound 161 (20.01 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:757.3448 (theory: 757.3434). Theoretical element content (%) C 52 H 31 D 7 N 4 O 2 : c,82.40; h,5.98; n,7.39. Measured element content (%): c,82.42; h,5.95; n,7.38.
Synthesis example 15: preparation of Compound 164
According to the same manner as in Compound 3 of Synthesis example 1, A-3 and c-3 were replaced with equimolar A-159 and c-164, respectively, and the other steps were the same, to obtain Compound 164 (18.49 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:679.2977 (theory: 679.2965). Theoretical element content (%) C 46 H 25 D 7 N 4 O 2 : c,81.27; h,5.78; n,8.24. Measured element content (%): c,81.28; h,5.76; n,8.28.
Synthesis example 16: preparation of Compound 165
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 and c-3 were replaced with equimolar amounts of b-165 and c-165, respectively, and the other steps were the same, to obtain Compound 165 (17.91 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z:648.2282 (theory: 648.2291). Theoretical element content (%) C 43 H 16 D 7 N 5 O 2 ：C,79.61；H4.66; n,10.80. Measured element content (%): c,79.62; h,4.63; n,10.84.
Synthesis example 17: preparation of Compound 173
According to the same manner as in Compound 3 of Synthesis example 1 except that A-3 was replaced with equimolar A-159, compound 173 (17.86 g) was obtained in the same manner as in the other steps, and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:628.2663 (theory: 628.2652). Theoretical element content (%) C 42 H 12 D 12 N 4 O 2 : c,80.23; h,5.77; n,8.91. Measured element content (%): c,80.25; h,5.75; n,8.94.
Synthesis example 18: preparation of Compound 174
According to the same manner as in Compound 3 of Synthesis example 1 except that A-3 and c-3 were replaced with equimolar amounts of A-159 and c-174, respectively, the other steps were the same, to obtain Compound 174 (19.32 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z:720.2871 (theory: 720.2884). Theoretical element content (%) C 48 H 12 D 14 N 4 O 3 : c,79.98; h,5.59; n,7.77. Measured element content (%): c,79.95; h,5.57; n,7.78.
Synthesis example 19: preparation of Compound 175
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 was replaced with b-175 in equimolar amounts, compound 175 (18.11 g) was obtained in the same manner as in other steps, and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:637.1971 (theoretical value: 637.198) 5). Theoretical element content (%) C 42 H 19 D 5 N 4 OS: c,79.10; h,4.58; n,8.78. Measured element content (%): c,79.12; h,4.55; n,8.76.
Synthesis example 20: preparation of Compound 188
According to the same production method as that of Compound 3 in Synthesis example 1, b-3 and c-3 were replaced with equimolar amounts of b-188 and c-188, respectively, and the other steps were the same, to obtain Compound 188 (20.48 g), and the purity of the solid was not less than 99.91% as measured by HPLC. Mass spectrum m/z:799.3346 (theory: 799.3359). Theoretical element content (%) C 57 H 33 D 5 N 4 O: c,85.58; h,5.42; n,7.00. Measured element content (%): c,85.56; h,5.45; n,7.03.
Synthesis example 21: preparation of Compound 199
Preparation of d-199:
e-199 (29.70 g,70 mmol), pinacol diboronate (18.66 g,73.5 mmol), KOAc (20.61 g,210 mmol) and then 300mL of 1, 4-dioxane were added under nitrogen, after 3X-substitution of nitrogen with Pd (dppf) Cl 2 (0.59 g,0.8 mmol) was stirred at 90℃for 5 hours, after the reaction was completed, the reaction was cooled to room temperature, distilled water was added, followed by extraction with ethyl acetate (500 mL. Times.3), the organic phase was separated, dried over anhydrous magnesium sulfate, and the obtained solid was obtained with hexane: ea=7:1 (v/v) to give d-199 (27.06 g, 82%), HPLC purity ≡99.84%, mass spectrum m/z:471.2017 (theory: 471.2006).
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 and d-3 were replaced with equimolar amounts of b-199 and d-199, respectively, the other steps were the same, compound 199 (19.72 g) was obtained, HPLC analysisThe purity of the measured solid is more than or equal to 99.93 percent. Mass spectrum m/z:746.2859 (theory: 746.2842). Theoretical element content (%) C 52 H 26 D 5 N 5 O: c,83.62; h,4.86; n,9.38. Measured element content (%): c,83.63; h,4.84; n,9.36.
Synthesis example 22: preparation of Compound 207
According to the same manner as that of Compound 3 in Synthesis example 1 except that b-3 was replaced with b-207 in equimolar amounts, compound 207 (18.54 g) was obtained in the same manner, and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:671.2385 (theory: 671.2370). Theoretical element content (%) C 46 H 21 D 5 N 4 O 2 : c,82.25; h,4.65; n,8.34. Measured element content (%): c,82.23; h,4.66; n,8.32.
Synthesis example 23: preparation of Compound 216
Preparation of e-216:
to a reaction flask was added f-216 (28.69 g,100 mmol), d-3 (33.92 g,100 mmol), potassium carbonate (27.64 g,200 mmol), then 350mL toluene/ethanol/water mixed solvent (toluene: ethanol: water volume ratio=2:1:1), then tetrakis (triphenylphosphine) palladium (0.12 g,0.10 mmol) under stirring and refluxing conditions were added, after completion of the reaction, the reaction was cooled to room temperature, distilled water was added, and the mixture was left to stand for separation, the separated organic phase was concentrated by distillation under reduced pressure, the solvent was suction filtered, the filter cake was rinsed with ethanol, and the obtained filter cake was recrystallized with toluene to give e-216 (38.62 g, 85%), HPLC purity +.99.81%, mass spectrum m/z:453.0651 (theory: 453.0666).
Preparation d-216:
to the reaction flask was added e-216 (31.81 g,70 mmol), pinacol diboronate (18.66 g,73.5 mmol), KOAc (20.61 g,210 mmol), then 300ml1, 4-dioxane, 3 times with nitrogen, pd (dppf) Cl 2 (0.59 g,0.8 mmol) was stirred at 90℃for 6 hours, after the reaction was completed, the reaction was cooled to room temperature, distilled water was added, followed by extraction with ethyl acetate (500 mL. Times.3), the organic phase was separated, dried over anhydrous magnesium sulfate, and the obtained solid was obtained with hexane: ea=7:1 (v/v) to give d-216 (29.13 g, 83%), HPLC purity ≡99.84%, mass spectrum m/z:501.2427 (theory: 501.2413).
According to the same manner as in Compound 3 of Synthesis example 1, c-3 and d-3 were replaced with equimolar amounts of c-159 and d-216, respectively, and the other steps were the same, to obtain Compound 216 (18.37 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:646.2323 (theory: 646.2307). Theoretical element content (%) C 44 H 22 D 4 N 4 O 2 : c,81.71; h,4.67; n,8.66. Measured element content (%): c,81.74; h,4.65; n,8.67.
Synthesis example 24: preparation of Compound 229
According to the same manner as that of compound 216 in Synthesis example 23 except that f-216 and d-216 were replaced with equimolar amounts of f-229 and d-229, respectively, the other steps were the same, to obtain compound 229 (19.01 g), and the purity of the solid as measured by HPLC was not less than 99.95%. Mass spectrum m/z:698.2577 (theory: 698.2589). Theoretical element content (%) C 48 H 22 D 6 N 4 O 2 : c,82.50; h,4.90; n,8.02. Measured element content (%): c,82.52; h,4.93; n,8.01.
Synthesis example 25: preparation of Compound 237
According toThe same procedures as in preparation example 23 were repeated except for using f-216, B-216 and d-216 as the starting materials instead of f-237, B-3 and d-237 in the same molar amounts, respectively, to give 237 (18.25 g) as a compound having a purity of not less than 99.97% as measured by HPLC. Mass spectrum m/z:651.2638 (theory: 651.2621). Theoretical element content (%) C 44 H 17 D 9 N 4 O 2 : c,81.08; h,5.41; n,8.60. Measured element content (%): c,81.06; h,5.45; n,8.63.
Synthesis example 26: preparation of Compound 290
According to the same manner as in Compound 3 of Synthesis example 1, A-3, c-3 and d-3 were replaced with equimolar amounts of A-151, c-290 and d-290, respectively, and the other steps were the same, to give Compound 290 (19.80 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:749.2822 (theory: 749.2808). Theoretical element content (%) C 52 H 23 D 7 N 4 O 2 : c,83.29; h,4.97; n,7.47. Measured element content (%): c,83.28; h,4.95; n,7.46.
Synthesis example 27: preparation of Compound 295
Preparation of g-295:
under nitrogen protection, h-295 (52.39 g,140 mmol), pinacol diboronate (37.33 g,147 mmol), KOAc (41.22 g,420 mmol) and 600ml1, 4-dioxane were added, after 3 air substitutions with nitrogen, pd (dppf) Cl were added 2 (1.17 g,1.6 mmol) was stirred at 90℃for 6.5 hours, after the reaction was completed, the reaction was cooled to room temperature, distilled water was added, followed by extraction with ethyl acetate (500 mL. Times.3), the organic phase was separated, dried over anhydrous magnesium sulfate, and the obtained solid was purified with hexane: EA=7:1 (v/v) to yield g-295 (50.72 g, 86%), HPLC purity ∈99.76%, mass spectrum m/z:421.1836 (theory: 421.1849).
According to the same manner as that for the preparation of compound 216 in Synthesis example 23, f-216, d-3, A-3 and d-216 were replaced with equimolar amounts of f-237, g-295, A-175 and d-295, respectively, and the other steps were the same, to obtain compound 295 (19.10 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z:712.2247 (theory: 712.2235). Theoretical element content (%) C 48 H 24 D 4 N 4 OS: c,80.87; h,4.52; n,7.86. Measured element content (%): c,80.86; h,4.54; n,7.88.
Synthesis example 28: preparation of Compound 311
According to the same manner as in Compound 3 of Synthesis example 1 except that d-3 was replaced with d-311 in equimolar amounts, compound 311 (16.93 g) was obtained in the same manner as in other steps, and the purity of the solid was not less than 99.99% as measured by HPLC. Mass spectrum m/z:587.1815 (theory: 587.1828). Theoretical element content (%) C 38 H 17 D 5 N 4 OS: c,77.66; h,4.63; n,9.53. Measured element content (%): c,77.68; h,4.64; n,9.55.
Synthesis example 29: preparation of Compound 334
According to the same manner as in Compound 3 of Synthesis example 1 except that b-3 and d-3 were replaced with equimolar amounts of b-334 and d-311, respectively, the other steps were the same, to give Compound 334 (18.11 g), and the purity of the solid as measured by HPLC was not less than 99.98%. Mass spectrum m/z:637.1974 (theory: 637.1985). Theoretical element content (%) C 42 H 19 D 5 N 4 OS: c,79.10; h,4.58; n,8.78. Measured element content (%): c,79.12; h,4.55; n,8.76.
Synthesis example 30: preparation of Compound 394
According to the same manner as in Compound 3 of Synthesis example 1, A-3, c-3 and d-3 were replaced with equimolar amounts of A-147, c-394 and d-311, respectively, and the other steps were the same, to give Compound 394 (19.10 g), the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:712.2223 (theory: 712.2235). Theoretical element content (%) C 48 H 24 D 4 N 4 OS: c,80.87; h,4.52; n,7.86. Measured element content (%): c,80.86; h,4.54; n,7.87.
Synthesis example 31: preparation of Compound 405
According to the same manner as in Compound 3 of Synthesis example 1 except that B-3 and d-3 were replaced with equimolar amounts of B-175 and d-311, respectively, the other steps were the same, to give Compound 405 (18.05 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z:653.1742 (theory: 653.1756). Theoretical element content (%) C 42 H 19 D 5 N 4 S 2 : c,77.15; h,4.47; n,8.57. Measured element content (%): c,77.16; h,4.49; n,8.55.
Synthesis example 32: preparation of Compound 429
According to the same manner as that of compound 216 in Synthesis example 23 except that f-216, d-3, b-3, c-159 and d-216 were replaced with equimolar amounts of f-429, d-311, b-429, c-429 and d-429 respectively, the other steps were the same, to obtain compound 429 (20.36 g), and the purity of the solid as measured by HPLC was not less than 99.92%. Mass spectrum m/z:782.2968 (theory: 782.2955). Theoretical element content (%) C 53 H 26 D 8 N 4 OS: c,81.30; h,5.41; n,7.16. Measured element content (%): c,81.33; h,5.42; n,7.15.
Synthesis example 33: preparation of Compound 454
According to the same manner as that of compound 216 in Synthesis example 23, f-216, d-3, B-216 and d-216 were replaced with equimolar amounts of f-237, d-311, B-295 and d-454, respectively, and the other steps were the same, to obtain compound 454 (19.54 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z:728.2021 (theory: 728.2006). Theoretical element content (%) C 48 H 24 D 4 N 4 S 2 : c,79.09; h,4.42; n,7.69. Measured element content (%): c,79.08; h,4.45; n,7.65.
Synthesis example 34: preparation of Compound 461
According to the same manner as that of Compound 216 in Synthesis example 23 except that e-216, B-216 and d-216 were replaced with equimolar amounts of e-461, B-3 and d-461, respectively, compound 461 (17.19 g) was obtained, and the purity of the solid was not less than 99.99% as measured by HPLC. Mass spectrum m/z:596.2361 (theory: 596.2373). Theoretical element content (%) C 40 H 20 D 5 N 5 O: c,80.52; h,5.07; n,11.74. Measured element content (%): c,80.54; h,5.04; n,11.72.
Synthesis example 35: preparation of Compound 510
According to the same manner as in Compound 216 of Synthesis example 23, e-216, a-3, b-3, c-159 and d-216 were each replaced with equimolar onesThe steps of e-510, a-510, b-510, c-3 and d-510 are the same, and the compound 510 (17.12 g) is obtained, and the purity of the solid detected by HPLC is more than or equal to 99.98 percent. Mass spectrum m/z:602.1633 (theory: 602.1647). Theoretical element content (%) C 39 H 18 D 5 N 3 S 2 : c,77.71; h,4.68; n,6.97. Measured element content (%): c,77.72; h,4.65; n,6.96.
Synthesis example 36: preparation of Compound 531
According to the same manner as in Compound 3 of Synthesis example 1 except that a-3, b-3 and d-3 were replaced with equimolar amounts of a-531, b-531 and d-311, respectively, the other steps were the same, compound 531 (17.55 g) was obtained, and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:635.2096 (theory: 635.2080). Theoretical element content (%) C 44 H 21 D 5 N 2 OS: c,83.12; h,4.91; n,4.41. Measured element content (%): c,83.15; h,4.92; n,4.43.
Device example 1
The glass substrate was washed with distilled water and ultrasonic waves. After the distilled water washing is completed, ultrasonic washing is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying is performed. An anode is formed of Indium Tin Oxide (ITO) on the substrate on which the reflective layer is formed. Vacuum evaporating compound HI on anode to obtain a film with a thickness of A Hole Injection Layer (HIL). Evaporating a compound HT on the hole injection layer to a thickness of +.>Is provided. Evaporating compound EB on the hole transport layer to form a layer with a thickness of +>Is a barrier to electrons. In electron blockingOn the layer, both the inventive compound 3 and the inventive compound H-1 were mixed in a weight ratio of 60% to 40% to form a mixed body, which was mixed with the dopant Ir (piq) 2 (acac) according to 94%:6% of evaporation rate is higher than common vacuum evaporation to form a film with a thickness of +>Is an emission layer (EML). Evaporating a compound HB on the light-emitting layer to form a film having a thickness +.>Is a hole blocking layer of (a). On the hole blocking layer, the compounds ET and LiQ are mixed in a weight ratio of 50% to 50% and evaporated to a thickness +.>Electron Transport Layer (ETL). Evaporating LiF on electron transport layer to form LiF with thickness +.>Electron Injection Layer (EIL). On the electron injection layer, magnesium (Mg) and silver (Ag) were mixed in a ratio of 1:9, and vacuum vapor deposition to a thickness ofIs provided. Evaporating CP on the cathode to form a film with a thickness of +.>Is an organic Coating (CPL). Thereby completing the manufacture of the organic light emitting device. />
Device examples 2 to 36
An organic electroluminescent device was produced by the same production method as in device example 1, except that compound 3 in device example 1 was replaced with compound 4, compound 10, compound 28, compound 93, compound 100, compound 102, compound 138, compound 144, compound 147, compound 151, compound 155, compound 159, compound 161, compound 164, compound 165, compound 173, compound 174, compound 175, compound 188, compound 199, compound 207, compound 216, compound 229, compound 237, compound 290, compound 295, compound 311, compound 334, compound 394, compound 405, compound 429, compound 454, compound 461, compound 510 and compound 531, respectively, as a host material for the light-emitting layer.
Comparative device examples 1 to 5
An organic electroluminescent device was produced by the same production method as in device example 1, except that compound H-2, compound H-3, compound H-4, compound H-5, and compound H-6 were used as the host material of the light-emitting layer in place of compound 3 in device example 1, respectively.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photoresearch company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000OLED life test system from McScience was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 1 to 36 in the device examples according to the present invention and the organic electroluminescent devices obtained in the comparative examples 1 to 5 are shown in table 1 below.
Table 1:
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as can be seen from the results in Table 1, when the heterocyclic compound of the present invention is applied to the host material of the light-emitting layer of the organic electroluminescent device, the device has higher light-emitting efficiency and longer service life, and the compound of the present invention is a host material of the light-emitting layer with good performance.
Device example 37
The glass substrate was washed with distilled water and ultrasonic waves. After the distilled water washing is completed, ultrasonic washing is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying is performed. An anode is formed of Indium Tin Oxide (ITO) on the substrate on which the reflective layer is formed. Vacuum evaporating HI-2 on anode to obtain a film with a thickness ofA Hole Injection Layer (HIL). Evaporating compound HT-2 on the hole injection layer to form a layer having a thickness of +>Is provided. Evaporating compound EB on the hole transport layer to form a layer with a thickness of +>Is a barrier to electrons. On the electron blocking layer, compound H-7 is reacted with the dopant Ir (ppy) 2 (acac) according to 95%: vapor deposition rate of 5% is higher than common vacuum vapor deposition to form a film having a thickness +.>Is an emission layer (EML). On the light-emitting layer, a compound HB-2 was vapor-deposited to a thickness of +.>Is a hole blocking layer of (a). Evaporating the compound 3 of the present invention on the hole blocking layer to form a film having a thickness of +>Electron Transport Layer (ETL). Evaporating LiF on electron transport layer to form LiF with thickness +.>Electron Injection Layer (EIL). On the electron injection layer, magnesium (Mg) and silver (Ag) were mixed in a ratio of 1:9, and vacuum evaporating to form a film with a thickness +.>Is provided. Thereby completing the manufacture of the organic light emitting device.
Device examples 38 to 72
An organic electroluminescent device was produced by the same production method as in device example 37, except that compound 3 in device example 37 was replaced with compound 4, compound 10, compound 28, compound 93, compound 100, compound 102, compound 138, compound 144, compound 147, compound 151, compound 155, compound 159, compound 161, compound 164, compound 165, compound 173, compound 174, compound 175, compound 188, compound 199, compound 207, compound 216, compound 229, compound 237, compound 290, compound 295, compound 311, compound 334, compound 394, compound 405, compound 429, compound 454, compound 461, compound 510 and compound 531, respectively, as an electron transporting material.
Comparative device examples 6 to 10
An organic electroluminescent device was produced by the same production method as in device example 37, except that compound H-2, compound H-3, compound H-4, compound H-5 and compound H-6 were used as electron transporting materials in place of compound 3 in device example 37, respectively.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photoresearch company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000OLED life test system from McScience was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 37 to 72 in the device examples according to the present invention and the organic electroluminescent devices obtained in comparative examples 6 to 10 are shown in table 2 below.
Table 2:
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as can be seen from the results of table 2, when the heterocyclic compound of the present invention is applied to the electron transport layer material of the organic electroluminescent device, the device has higher luminous efficiency and longer service life, and the compound of the present invention is an electron transport layer material with good performance.
Device example 73]
The glass substrate was washed with distilled water and ultrasonic waves. After the distilled water washing is completed, ultrasonic washing is performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying is performed. An anode is formed of Indium Tin Oxide (ITO) on the substrate on which the reflective layer is formed. Vacuum evaporating HI-3 on anode to form a film with a thickness ofA Hole Injection Layer (HIL). Evaporating compound HT-3 on the hole injection layer to form a layer having a thickness of +>Is provided. Evaporating compound EB on the hole transport layer to form a layer with a thickness of +>Is a barrier to electrons. On the electron blocking layer, compound H-8 is reacted with the dopant Ir (ppy) 3 According to 93%: the evaporation rate of 7% is higher than that of common vacuum evaporation to form a film with a thickness of + >Is an emission layer (EML). Evaporating the compound 3 of the present invention on the light-emitting layer to form a film having a thickness of +>Is a hole blocking layer of (a). On the hole blocking layer, the compounds ET and LiQ are mixed in a weight ratio of 50% to 50% and evaporated to a thickness +.>Electron Transport Layer (ETL). Evaporating LiF on electron transport layer to form LiF with thickness +.>Electron Injection Layer (EIL). On the electron injection layer, magnesium (Mg) and silver (Ag) were mixed in a ratio of 1:9, and vacuum evaporating to form a film with a thickness +.>Is provided. Thereby completing the manufacture of the organic light emitting device.
Device examples 74 to 108
An organic electroluminescent device was produced by the same production method as in device example 73, except that compound 3 in device example 73 was replaced with compound 4, compound 10, compound 28, compound 93, compound 100, compound 102, compound 138, compound 144, compound 147, compound 151, compound 155, compound 159, compound 161, compound 164, compound 165, compound 173, compound 174, compound 175, compound 188, compound 199, compound 207, compound 216, compound 229, compound 237, compound 290, compound 295, compound 311, compound 334, compound 394, compound 405, compound 429, compound 454, compound 461, compound 510 and compound 531, respectively, as a hole blocking material.
Comparative device examples 11 to 15
An organic electroluminescent device was produced by the same production method as in device example 73, except that compound H-2, compound H-3, compound H-4, compound H-5 and compound H-6 were used as hole blocking materials in place of compound 3 in device example 73, respectively.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photoresearch company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000OLED life test system from McScience was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of devices 73 to 108 in the device examples according to the present invention and the organic electroluminescent devices obtained in comparative examples 11 to 15 are shown in table 3 below.
Table 3:
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as can be seen from the results in Table 3, when the heterocyclic compound of the present invention is applied to a hole blocking layer material of an organic electroluminescent device, the device has higher luminous efficiency and longer service life, and the compound of the present invention is a hole blocking layer material with good performance.
It should be noted that while the present invention has been specifically described with reference to individual embodiments, it will be apparent to those skilled in the art that numerous modifications and variations can be made without departing from the principles of the present invention, and such modifications and variations fall within the scope of the present invention.
Claims (10)
1. A heterocyclic compound, wherein the heterocyclic compound has a structure represented by formula I:
group 1:
wherein the Ar is 1 Any one selected from the formula II and the formula III;
the ring A is selected from any one of the structures in the group 1; * Is a condensed site;
the ring B is selected from any one of C6-C18 aryl;
x is selected from any one of CH and N, and at least one of X is selected from N;
said Y is selected from O, S, N (R) d ) Any one of them;
the Y is 1 、Y 2 Independently selected from O, S, C (R a R b )、N(R c ) Any one of them;
the V is selected from any one of CH and N;
the Ar is as follows 2 Any one selected from the group consisting of aryl groups of formulae II, III, substituted or unsubstituted C6 to C30, heteroaryl groups of substituted or unsubstituted C2 to C30, fused ring groups of substituted or unsubstituted C3 to C30 alicyclic rings and C6 to C30 aromatic rings, fused ring groups of substituted or unsubstituted C1 to C25 heterocyclic alkanes and C6 to C30 aromatic rings, fused ring groups of substituted or unsubstituted C3 to C25 alicyclic rings and C2 to C30 heteroaromatic rings;
the L is selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstitutedAny one of C3-C30 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 heteroaromatic ring, and Ar 1 、Ar 2 、L、R 2 Contains at least one or more deuterium;
the R is 0 、R 1 、R 2 、R 3 、R 4 Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups;
the a 0 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R's are present 0 When two or more R' s 0 Are the same as or different from each other;
the a 1 Selected from 0 or 1;
the a 2 Selected from 0, 1 or 2; when there are two R 2 When two R 2 Are the same as or different from each other;
the a 3 Selected from 0, 1, 2, 3 or 4; when two or more R's are present 3 When two or more R' s 3 Are identical or different from each other, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
the a 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 4 When two or more R' s 4 Are identical or different from each other, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is a 、R b Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstitutedC1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R a 、R b Form a substituted or unsubstituted ring;
the R is c Any one selected from the group consisting of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C1-C25 heterocycloalkyl ring and a C6-C30 aromatic ring condensed ring group, a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring condensed ring group.
2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is selected from any one of the following structures:
the R is p 、R q 、R r Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C30 heteroarylAny one of a substituted or unsubstituted C3 to C30 alicyclic ring and a C6 to C30 condensed ring group of an aromatic ring, a substituted or unsubstituted C1 to C25 heterocyclic alkane and a C6 to C30 condensed ring group of an aromatic ring, a substituted or unsubstituted C3 to C25 alicyclic ring and a C2 to C30 condensed ring group of a heteroaromatic ring;
said g 1 Selected from 0, 1, 2, 3, 4, 5 or 6; said g 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 3 Selected from 0, 1, 2, 3, 4 or 5; said g 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present q When two or more R' s q Are identical or different from each other, or adjacent two R q Are connected with each other to form a substituted or unsubstituted ring;
the h is 1 Selected from 0, 1, 2, 3 or 4; when two or more R's are present r When two or more R' s r Are identical or different from each other, or adjacent two R r Are linked to each other to form a substituted or unsubstituted ring.
3. The heterocyclic compound according to claim 1, wherein said formula II is selected from any one of the following structures:
the R is 9 Selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring groupsAny one of a substituted or unsubstituted C3 to C25 alicyclic ring and a C2 to C30 condensed cyclic group of a heteroaromatic ring;
said f 1 Selected from 1, 2, 3, 4 or 5; said f 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said f 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said f 4 Selected from 1 or 2; said f 5 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said f 6 Selected from 1, 2, 3 or 4; said f 7 Selected from 1, 2 or 3; when two or more R's are present 9 When two or more R' s 9 Are identical or different from each other, or adjacent two R 9 Are linked to each other to form a substituted or unsubstituted ring.
4. The heterocyclic compound according to claim 1, wherein the formula III is selected from any one of the following structures:
the R is 5 Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups;
said b 1 Selected from 1, 2, 3, 4 or 5; said b 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said b 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 4 Selected from 1 or 2; said b 5 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said b 6 Selected from 1, 2, 3 or 4; said b 7 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b 8 Selected from 1, 2, 3, 4, 5 or 6; said b 9 Selected from 1, 2 or 3; when two or more R's are present 5 When two or more R' s 5 Are identical or different from each other, or adjacent two R 5 Are linked to each other to form a substituted or unsubstituted ring.
5. The heterocyclic compound according to claim 1, wherein Ar 2 When the structural formula is not represented by the formulas II and III, the structural formula is selected from any one of the following structures:
the R is 6 The same or different is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 condensed ring groups of aromatic rings, substituted or unsubstituted C3-C25 alicyclic and C2-C30 condensed ring groups of heteroaromatic rings;
the c 1 Selected from 0, 1, 2, 3, 4 or 5; the c 2 Selected from 0, 1, 2, 3 or 4; the c 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c 5 Selected from 0, 1 or 2; the c 6 Selected from 0, 1, 2, 3, 4, 5, 6,7. 8, 9, 10 or 11; the c 7 Selected from 0, 1, 2 or 3; when two or more R's are present 6 When two or more R' s 6 Are identical or different from each other, or adjacent two R 6 Are connected with each other to form a substituted or unsubstituted ring;
the R is d Independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
z is selected from any one of CH and N;
the Y is 4 、Y 5 Each independently selected from O, S, C (R) e R f )、N(R g ) Any one of them;
the R is e 、R f Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R e 、R f Form a substituted or unsubstituted ring;
the R is g Any of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groupsOne of the two.
6. The heterocyclic compound according to claim 1, wherein L is selected from a single bond or from any one of the following structures:
the R is 7 Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups;
Said d 1 Selected from 0, 1, 2, 3 or 4; said d 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 4 Selected from 0, 1 or 2; said d 5 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present 7 When two or more R' s 7 Are identical or different from each other, or adjacent two R 7 Are connected with each other to form a substituted or unsubstituted ring;
the L is 1 Any one selected from a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C30, a substituted or unsubstituted alicyclic ring of C3 to C30 and a fused ring-back group of an aromatic ring of C6 to C30, a substituted or unsubstituted alicyclic ring of C3 to C25 and a fused ring-back group of a heteroaromatic ring of C2 to C30;
the J is selected from any one of CH and N;
the R is h Selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkylAny one of a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group;
the Y is 6 、Y 7 、Y 8 Is independently selected from O, S, C (R) i R j )、N(R k ) Any one of them;
The R is i 、R j Each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R i 、R j Form a substituted or unsubstituted ring;
the R is k Any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups.
7. The heterocyclic compound according to claim 1, wherein Ar 2 When the structural formula is not represented by the formulas II and III, the structural formula is selected from any one of the following structures:
the R is 8 The same or different is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 condensed ring groups of aromatic rings, substituted or unsubstituted C3-C25 alicyclic and C2-C30 condensed ring groups of heteroaromatic rings;
said e 1 Selected from 0, 1, 2, 3, 4 or 5; said e 2 Selected from 0, 1, 2, 3 or 4; said e 3 Selected from 0, 1, 2 or 3; said e 4 Selected from 0, 1 or 2; said e 5 Selected from 0 or 1; said e 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said e 7 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said e 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said e 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 12 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; said e 13 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; said e 14 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; said e 15 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R's are present 8 When two or more R' s 8 Are identical or different from each other, or adjacent two R 8 Are connected with each other to form a substituted or unsubstituted ring;
the R is m 、R n Each independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups.
8. The heterocyclic compound according to claim 1, wherein the compound of formula I is selected from any one of the following structures:
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9. an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic layer comprises at least one of an electron transport layer and a hole blocking layer, the at least one of an electron transport layer and a hole blocking layer comprising at least one of the heterocyclic compounds according to any one of claims 1 to 8.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117510399A (en) * | 2024-01-08 | 2024-02-06 | 广东阿格蕾雅光电材料有限公司 | Compound, functional material, electronic element and electronic device |
| CN117510399B (en) * | 2024-01-08 | 2024-05-14 | 广东阿格蕾雅光电材料有限公司 | Compound, functional material, electronic element and electronic device |
-
2023
- 2023-08-28 CN CN202311092184.4A patent/CN117126149A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117510399A (en) * | 2024-01-08 | 2024-02-06 | 广东阿格蕾雅光电材料有限公司 | Compound, functional material, electronic element and electronic device |
| CN117510399B (en) * | 2024-01-08 | 2024-05-14 | 广东阿格蕾雅光电材料有限公司 | Compound, functional material, electronic element and electronic device |
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