CN113735794A - Compound containing condensed aryl and organic electroluminescent device thereof - Google Patents
Compound containing condensed aryl and organic electroluminescent device thereof Download PDFInfo
- Publication number
- CN113735794A CN113735794A CN202111131667.1A CN202111131667A CN113735794A CN 113735794 A CN113735794 A CN 113735794A CN 202111131667 A CN202111131667 A CN 202111131667A CN 113735794 A CN113735794 A CN 113735794A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- compound
- group
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 147
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 59
- 239000010410 layer Substances 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 230000000903 blocking effect Effects 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 57
- 238000001704 evaporation Methods 0.000 abstract description 14
- 230000008020 evaporation Effects 0.000 abstract description 14
- 230000009477 glass transition Effects 0.000 abstract description 7
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 98
- 238000003786 synthesis reaction Methods 0.000 description 97
- -1 n-octyl Chemical group 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000543 intermediate Substances 0.000 description 36
- 238000001819 mass spectrum Methods 0.000 description 36
- 238000004128 high performance liquid chromatography Methods 0.000 description 35
- 230000000052 comparative effect Effects 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000012065 filter cake Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 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 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 4
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 3
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 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 2
- 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 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- WYSBZCPNRXECEW-UHFFFAOYSA-N 1-diazo-2H-anthracene Chemical class C1=CC=C2C=C3C(=[N+]=[N-])CC=CC3=CC2=C1 WYSBZCPNRXECEW-UHFFFAOYSA-N 0.000 description 1
- 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 class N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical group C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- RWWUBXBYBPQIJI-UHFFFAOYSA-N cesium;quinolin-8-ol Chemical compound [Cs].C1=CN=C2C(O)=CC=CC2=C1 RWWUBXBYBPQIJI-UHFFFAOYSA-N 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a compound containing condensed aryl and an organic electroluminescent device thereof, relating to the technical field of photoelectric materials. The compound provided by the invention has high electron mobility, is easy to transmit electrons, can balance the transmission of holes and electrons, has high triplet state energy level and wide energy gap, and can limit excitons in a light-emitting layer, thereby improving the light-emitting efficiency and prolonging the service life of an organic electroluminescent device; on the other hand, a bridging group L is introduced0Then, the glass transition temperature and the refractive index of the compound are improved, the film forming property and the thermal stability of the material after evaporation film forming are improved, and when the compound is applied to an organic electroluminescent device, the luminous efficiency and the service life of the organic electroluminescent device can be improved.
Description
Technical Field
The invention relates to the technical field of photoelectric materials, in particular to a compound containing condensed aryl and application thereof in an organic electroluminescent device.
Background
An Organic Light-Emitting Diode (OLED) refers to a phenomenon that an ITO glass transparent electrode and a metal electrode are respectively used as an anode and a cathode of a device, electrons and holes are respectively injected from the cathode and the anode into an electron and hole transport layer under the drive of a certain voltage, then the electrons and the holes respectively migrate to a Light-Emitting layer and meet to form excitons so as to excite Light-Emitting molecules, and the latter emits visible Light after being radiated. The OLED has the advantages of low working voltage, high brightness, high efficiency, high contrast, thin thickness, light weight, wide visual angle, wide working temperature range, simple process, capability of being manufactured on a flexible substrate and the like. With the development of OLED technology, OLED can be widely applied to various portable and wall-mounted terminal displays, and has a very wide application prospect.
The organic electroluminescent device generally has a structure of an anode, a cathode and an organic layer therebetween, and the organic layer materials are mutually overlapped according to the purpose to form the organic electroluminescent device. Wherein the organic layer may include an electron injection layer, an electron transport layer, a hole blocking layer, a light emitting layer, a hole transport layer, a hole injection layer, and the like. Organic electroluminescent devices can be classified into two structures, one is a bottom emission type device and the other is a top emission type device, according to the difference in the direction in which light exits from the device. Because the light emitted by the top emission type device is emitted from the top of the device, the aperture opening ratio can be effectively improved without being influenced by the driving panel at the bottom of the device, and meanwhile, the top emission type device also has the advantages of improving the device efficiency, narrowing the spectrum, improving the color purity, improving the refractive index and the like, so the top emission type device has very good development prospect. The electron transport materials used in OLEDs are required to have high electron mobility and large electron affinity, while having suitable HOMO and LUMO energy levels to allow electrons to have a minimum injection energy barrier. The injection efficiency of electrons and the luminous efficiency of the device are improved. The hole blocking material has good color purity and stable chromaticity, so that current carriers from the anode are blocked into the organic functional layer film, the balance of the current carriers is improved, and the efficiency of the organic electroluminescent device is improved.
At present, the hole mobility of a hole transport material applied to an OLED is generally much greater than the electron mobility of an electron transport material, so that holes and electrons cannot be well combined in a light emitting layer, and meanwhile, the electron transport material does not have a hole blocking effect, so that carrier injection is unbalanced, and on the other hand, the light emitting efficiency is affected due to the problems of low light emitting efficiency and the like caused by the total reflection phenomenon of light at the interface of a device; in order to improve the light emitting efficiency of the organic electroluminescent device and prolong the service life of the device, it is a problem to be urgently broken through to design an electron transport material, a hole blocking material and a covering layer material with good performance.
Disclosure of Invention
In view of the above problems in the prior art, the present invention provides a compound containing a condensed aryl group and an application thereof in an organic electroluminescent device. The compound provided by the invention has higher triplet state energy level, higher glass transition temperature, good film forming property and high light extraction rate, and the designed compound can be used as an electron transport material, a hole blocking material and a covering layer material in an organic electroluminescent device to remarkably improve the luminous efficiency of the device and prolong the service life.
The technical scheme of the invention is as follows:
the invention provides a compound containing a fused aryl, which has a structure shown in a chemical formula 1:
in chemical formula 1, the a are the same as or different from each other and are selected from the group consisting of no, substituted or unsubstituted phenyl, and at least one a is selected from the group consisting of substituted or unsubstituted phenyl;
c is selected from the group represented by chemical formula 2;
the B is different from the C and is not a group represented by chemical formula 2, the B is selected from any one of substituted or unsubstituted C3-C12 naphthenic base, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl or combination thereof,
x is selected from any one of O, S;
said L0Is selected from substituted or unsubstituted arylene of C6-C30;
said L1、L2Any one of a single bond, a substituted or unsubstituted arylene group having C6-C30 groups, and a substituted or unsubstituted heteroarylene group having C2-C30 groups, which are the same or different from each other;
the R is0、R1、R2The aryl group is any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
n is0Independently selected from 0, 1, 2, 3 or 4N is said n1Is selected from 0, 1, 2, 3, 4 or 5, the n2Selected from 0, 1, 2 or 3, when n is0、n1、n2Greater than 1, two or more R0、R1、R2Two R's, equal to or different from each other, or adjacent1May be linked to form a substituted or unsubstituted ring.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode, an organic layer positioned between the anode and the cathode, and/or a covering layer positioned outside the anode and the cathode, wherein at least one of the organic layer or the covering layer comprises at least one of the compounds of the thick aryl described in the invention.
Advantageous effects
The compound containing the thick aryl has high electron mobility, is easy to transmit electrons, can balance the transmission of holes and electrons, and further improves the luminous efficiency of a device; meanwhile, the compound has high triplet state energy level and wide energy gap, and when the compound is applied to an organic layer, the diffusion of excitons to an adjacent functional layer is minimized, so that the luminous efficiency and the service life of an organic electroluminescent device can be improved.
On the other hand, a bridging group L is introduced0Then, the glass transition temperature and the refractive index of the compound are improved, the film forming property and the thermal stability of the material after film formation by evaporation are improved, and the service life of a device is prolonged when the compound is applied to an organic layer of an organic electroluminescent material; when the organic electroluminescent device is applied to a covering layer of an organic electroluminescent device, the light extraction efficiency of the device can be improved, and the light emitting efficiency of the device is further improved. In addition, the compound of the invention applied to the electron transport layer or the hole blocking layer has asymmetry, so that the material can exist in an amorphous state more stably, and when the compound is applied to an organic electroluminescent device, a more uniform heat-resistant film can be formed, and the service life of the device is prolonged.
In conclusion, the compound containing the condensed aryl provided by the invention has many advantages, and when the compound is applied to an organic electroluminescent device, the high luminous efficiency and the long service life can be realized, and the compound has good application effect and industrialization prospect.
Detailed Description
The following will clearly and completely describe the technical solutions of the specific embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
In the context of the present specification,
means a moiety attached to another substituent.
Can be attached at any optional position of the attached group/fragment. For example
To represent
And so on.
Examples of halogen atoms described herein may include fluorine, chlorine, bromine, and iodine.
The alkyl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from the alkane molecule, and may be a straight-chain or branched alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but is not limited thereto; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, the isomeric form of n-pentyl, the isomeric form of n-hexyl, the isomeric form of n-heptyl, the isomeric form of n-octyl, the isomeric form of n-nonyl, the isomeric form of n-decyl, and the like.
The cycloalkyl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from a cyclic alkane molecule, and preferably has 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and the like, but is not limited thereto.
The aryl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule, and may be monocyclic aryl group, polycyclic aryl group or condensed ring aryl group, and preferably has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, phenyl group and the like, but is not limited thereto; the polycyclic aromatic group means an aromatic group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but is not limited thereto; the fused ring aryl group refers to an aryl group having two or more aromatic rings in a molecule and fused together by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, spirofluorenyl, and the like. The above aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a benzofluorenyl group, a triphenylenyl group, a 9, 9' -spirobifluorenyl group, but is not limited thereto.
The heteroaryl group in the present invention refers to a general term of a group in which one or more of the aromatic nucleus carbon atoms in the aryl group is replaced with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atom, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be located 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. The monocyclic heteroaryl group includes pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl and the like, but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiin, and the like.
The arylene group in the present invention refers to a general term of divalent groups remaining after two hydrogen atoms are removed from the aromatic core carbon of the aromatic compound molecule, and may be monocyclic arylene group, polycyclic arylene group or condensed ring arylene group, and preferably has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene group and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, tetrabiphenylene, 1-phenylnaphthyl, 2-phenylnaphthyl, and the like, but is not limited thereto; the fused ring arylene group includes naphthylene, anthrylene, phenanthrylene, pyrenylene, peryleneene, fluorenylene, benzofluorenylene, triphenylene, fluoranthenylene, spirofluorenylene, and the like, but is not limited thereto.
Heteroarylene as used herein refers to the generic term for groups in which one or more of the aromatic core carbons in the arylene group is replaced with a heteroatom, including, but not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably from 3 to 60 carbon atoms, more preferably from 3 to 30 carbon atoms, particularly preferably from 3 to 18 carbon atoms, most preferably from 3 to 12 carbon atoms. The linking site of the heteroarylene may be located on a ring-forming carbon atom or a ring-forming heteroatom, and the heteroarylene may be a monocyclic heteroarylene, a polycyclic heteroarylene or a fused ring heteroarylene. The monocyclic heteroarylene group includes a pyridylene group, a pyrimidylene group, a triazinylene group, a furanylene group, a thiophenylene group, a pyrrolylene group, an oxazolylene group, a thiazolyl ene group, an imidazolyl group, etc., but is not limited thereto; the polycyclic heteroarylene group includes bipyridyl idene, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroarylene group includes a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a benzoisoquinolylene group, a quinazolinylene group, a quinoxalylene group, a benzoquinazolinylene group, a benzoquinoxalylene group, a naphthyrylene group, an indolyl group, a benzothiophene group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolylene group, a benzothiazolyl group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzooxazolylene group, a dibenzoimidazolyl group, a dibenzothiazolyl group, a carbazolyl group, a benzocarbazylene group, a 9, 10-dihydroacridine group, a phenoxazinyl group, a phenothiazinylene group, a phenoxathiin group and the like, but is not limited thereto.
The term "substituted … …" such as "substituted alkyl, substituted cycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene" as used herein means independently mono-or poly-substituted with: deuterium, a cyano group, a nitro group, a halogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C6 alkoxy group, a substituted or unsubstituted C1-C6 alkylthio group, a substituted or unsubstituted C1-C6 alkylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylamine group, and the like, but are not limited thereto. Preferably monosubstituted or polysubstituted with the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, perylenyl, pyrenyl, benzyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, dianilino, pyridyl, pyrimidyl, triazinyl, carbazolyl, acridinyl, furyl, thienyl, benzofuryl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl.
The term "linked to form a 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 to be connected may be an aromatic ring system, an aliphatic ring system, or a ring system formed by a fusion of the two, and the ring to be connected 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, cyclopentene, cyclopentane, cyclopenta, cyclohexene, cyclohexane, cyclohexan, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but not limited thereto.
The invention provides a compound containing a fused aryl, which has a structure shown in a chemical formula 1:
in chemical formula 1, the a are the same as or different from each other and are selected from the group consisting of no, substituted or unsubstituted phenyl, and at least one a is selected from the group consisting of substituted or unsubstituted phenyl;
c is selected from the group represented by chemical formula 2;
the B is different from the C and is not a group represented by chemical formula 2, the B is selected from any one of substituted or unsubstituted C3-C12 naphthenic base, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl or combination thereof,
x is selected from any one of O, S;
said L0Is selected from substituted or unsubstituted arylene of C6-C30;
said L1、L2Any one of a single bond, a substituted or unsubstituted arylene group having C6-C30 groups, and a substituted or unsubstituted heteroarylene group having C2-C30 groups, which are the same or different from each other;
the R is0、R1、R2The aryl group is any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
n is0Independently selected from 0, 1, 2, 3 or 4, said n1Is selected from 0, 1, 2, 3, 4 or 5, the n2Selected from 0, 1, 2 or 3, when n is0、n1、n2Greater than 1, two or more R0、R1、R2Two R's, equal to or different from each other, or adjacent1May be linked to form a substituted or unsubstituted ring.
Preferably, the compound is selected from any one of the structures shown in chemical formulas 1-1 to 1-3:
the R is0The aryl group is any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C18 heteroaryl;
m is1Is selected from 0, 1, 2, 3 or 4, m2Is selected from 0, 1, 2 or 3, m3Selected from 0, 1 or 2.
Preferably, the compound is selected from any one of the following groups:
still more preferably, said R0The alkyl groups are the same or different from each other and are independently any one of the following groups which are selected from hydrogen, deuterium, cyano, C1-C6 alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and the following groups which are unsubstituted or substituted by deuterium, cyano, adamantyl, norbornyl, phenyl and pyridyl: phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl.
Preferably, said L0Any one selected from the following groups:
each Rn is independently any one of hydrogen, deuterium, cyano, C1-C4 alkyl, C3-C12 cycloalkyl, C6-C12 aryl and C2-C12 heteroaryl;
b is1Selected from 0, 1, 2, 3 or 4, said b2Selected from 0, 1, 2 or 3, said b3Selected from 0, 1 or 2, said b4Selected from 0, 1, 2, 3, 4 or 5.
Still preferably, Rn is independently selected from any one of hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl and pyrimidyl.
Preferably, B is selected from any one of the following groups:
y is selected from C (Rm) or N atom, and at least one Y in each of C-1 to C-6 is selected from N atom;
said X1Selected from O, S, C (Ry)2Any one of the above;
the Ry is any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Ry can be connected to form a substituted or unsubstituted ring;
each Rm is independently any one selected from hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C12 alkyl 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, or two adjacent Rms can be connected to form a substituted or unsubstituted ring;
a is a1Selected from 0, 1, 2, 3, 4 or 5, said a2Selected from 0, 1, 2, 3 or 4, said a3Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a4Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a5Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10 or 11.
Preferably, at least two Y of each of C-1 to C-6 are selected from N atoms, alternatively at least three Y are selected from N atoms, alternatively at least four Y are selected from N atoms. Preferably, up to six Y atoms, or up to five Y atoms, per group of C-1 to C-6 are selected from N atoms.
Preferably, up to three Y atoms, or up to two Y atoms, or up to one Y atom, are selected from N atoms per six-membered aromatic ring in each of the groups C-1 to C-6.
Still preferably, B is selected from any one of the following groups:
preferably, said L1、L2The same or different from each other are selected from a single bond or any one of the following groups:
each Z is independently selected from a C (rz) or N atom; and
the bonded Z is a C atom;
said X2Selected from O atoms, S atoms or C (Rx)2Any one of the above;
the Rz is independently any one selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Rz can be connected to form a substituted or unsubstituted ring;
the Rx are the same or different from each other, and any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two Rx can be connected to form a substituted or unsubstituted ring.
Still more preferably, said L1、L2The same or different from each other are selected from a single bond or any one of the following groups:
preferably, C is selected from any one of the following groups:
most preferably, the compound is selected from any one of the following structures:
while specific structural forms of the compounds of the present invention have been illustrated above, the present invention is not limited to these specific structural forms, and any substituent group having the above-defined substituent group is included on the basis of the structure shown in formula 1.
The present invention also provides a method for preparing the compound represented by chemical formula 1, but the preparation method of the present invention is not limited thereto. The core structure of the compound of chemical formula 1 may be prepared by the reaction scheme shown below, substituents may be bonded by a method known in the art, and the kind and position of the substituents or the number of the substituents may be changed according to the art-known technique.
[ synthetic route of Compound of formula 1]
Xa-Xd are independently selected from any one of I, Br and Cl, and the reaction types related to the invention are Suzuki reaction and Miyaura boric acid esterification reaction.
The invention also provides an organic electroluminescent device comprising an anode, a cathode, an organic layer located between the anode and the cathode, and/or a cover layer located outside at least one of the anode and the cathode, at least one of the organic layer or the cover layer comprising at least one of the compounds according to the invention.
The organic layer of the present invention is located between the anode and the cathode, and the capping layer of the present invention is located outside at least one of the anode and the cathode. The organic layer may sequentially include at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and the organic layer may be correspondingly increased or decreased according to actual needs.
As the organic layer of the present invention, it may have the following structure: 1) a single layer structure comprising a single layer comprising a single material; or comprise a single layer comprising multiple materials; 2) a multi-layer structure comprising a plurality of layers comprising a plurality of materials. Specifically, the hole transport layer may include a first hole transport layer and a second hole transport layer, and the electron transport layer may include a first electron transport layer and a second electron transport layer.
Preferably, the organic layer comprises at least one of an electron transport layer or a hole blocking layer, and the at least one of the electron transport layer or the hole blocking layer comprises the compound of the present invention.
Preferably, the cover layer is located on the outer side of the cathode, and the cover layer comprises the compound of the present invention.
Preferably, the covering layer comprises the structure shown by the compounds 293 to 321 of the invention.
In the organic electroluminescent device according to one embodiment of the present invention, materials other than the compound of chemical formula 1 are shown below, however, these materials are for illustrative purposes only and are not intended to limit the scope of the present application, and may be substituted by materials known in the art.
As the anode material of the present invention, a material having a high work function is preferable. The anode may be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, a material for forming 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, a material for forming the anode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg)-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 triple layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.
As the hole injection layer material of the present invention, a material having a high work function is preferable, and may be selected from any one or more of the following structures: metalloporphyrin, oligothiophene, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.
As the hole transport layer material according to the present invention, a material having a high hole mobility is preferable, and may be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexacarbonitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., but are not limited thereto.
The light-emitting layer material of the present invention can be a red, green or blue light-emitting material, and usually contains a guest (doped) material and a host material, wherein the guest material can be a pure fluorescent material or a phosphorescent material, or can be a combination of fluorescent and phosphorescent materials. The host material of the light-emitting layer needs to have not only a bipolar charge transport property but also an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material, and examples of such materials include distyrylaryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, and the like. The guest material may be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but are not limited thereto.
As the hole-blocking layer material according to the present invention, a material capable of effectively blocking holes is generally preferred, and in addition to the compound containing a condensed aromatic group provided by the present invention, any one or more selected from the following structures may be used: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, and the like, but are not limited thereto.
As the electron transport layer material of the present invention, a material with high electron mobility is preferred, and besides the compound containing the condensed aryl provided by the present invention, the material can be selected from any one or more of the following structures: metal chelates, oxazoie derivatives, thiazole derivatives, triazole derivatives, azepine derivatives, diazoanthracene derivatives, silicon-containing heterocycles, boron-containing heterocycles, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, and the like, but are not limited thereto.
As the electron injection layer material of the present invention, a material having a low work function is preferable, and specific examples may include: alkali metal compounds (e.g., lithium oxide, lithium fluoride, cesium carbonate, cesium 8-hydroxyquinoline, aluminum 8-hydroxyquinoline), metal complexes, etc., and may also be formed using a mixture material of an electron transport material and an insulating organic metal salt, which may include, for example, a metal acetate, a metal benzoate, or a metal stearate, but is not limited thereto.
As the cathode material according to the present invention, a material having a low work function is preferable, and the cathode may be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive electrode, the material used to form the cathode may be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material for forming the cathode may be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.
As the coating layer of the present invention, in addition to the compound containing a condensed aryl group provided by the present invention, any one or more selected from the following structures may be used: inorganic compounds (e.g., metal oxides, metal nitrides, metal fluorides, etc.), organic compounds (arylamine derivatives, carbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, etc.), or may be formed by mixing inorganic compounds with organic compounds, but are not limited thereto.
Description of raw materials, reagents and characterization equipment:
the present invention is not particularly limited to the starting materials and sources of reagents used in the following examples, and they may be commercially available products or prepared by methods known to those skilled in the art.
The mass spectrum uses British Watts G2-Si quadrupole rod series time-of-flight high resolution mass spectrometer, chloroform is used as solvent;
the element analysis uses a Vario EL cube type organic element analyzer of Germany Elementar company, and the mass of a sample is 5-10 mg;
synthesis example 1 Synthesis of Compound 1
Preparation of intermediate 1-1:
under the protection of nitrogen, a-1(302.60mmol, 92.96g), b-1(300.00mmol, 46.91g), Pd (PPh)3)4(2.30mmol, 2.66g) and 900mL of toluene, 300mL of ethanol were added to the reaction flask, the mixture was stirred, and 300mL of 2M K was added2CO3The aqueous solution was injected into the above solution through a syringe and reacted for 2 hours under reflux. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (10: 3 recrystallization to give intermediate 1-1(83.35g, 82% yield); the HPLC purity is more than or equal to 99.46 percent. Mass spectrum m/z: 338.0873 (theoretical value: 338.0862).
Preparation of intermediates 1-2:
intermediate 1-1(220.00mmol, 74.54g), d-1(230.00mmol, 58.41g) and KOAc (450.00mmol, 44.16g) were dissolved in anhydrous dioxane (1600mL) under nitrogen atmosphere, and Pd (dppf) Cl was added after nitrogen substitution2(3.00mmol, 2.20g) was heated under reflux for 3.5 hours. After the reaction was completed, it was cooled to room temperature, the mixture was poured into water, extracted with dichloromethane, and the organic layer was extracted with anhydrous MgSO4Drying and rotary evaporation are carried out, and the crude product is recrystallized by ethyl acetate. Drying afforded intermediate 1-2(79.53g, 84% yield); the HPLC purity is more than or equal to 99.54 percent. Mass spectrum m/z: 430.2112 (theoretical value: 430.2104).
Preparation of intermediates 1 to 3:
under the protection of nitrogen, intermediate 1-2(183.40mmol, 78.93g), e-1(180.00mmol, 57.12g), Pd (PPh)3)4(3.40mmol, 3.93g) and 510mL of toluene, 170mL of ethanol were added to the reaction flask, the mixture was stirred, and 170mL of 2M K was added2CO3The aqueous solution was injected into the above solution through a syringe and reacted at reflux for 3.5 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (5: 1 recrystallization to give intermediate 1-3(71.11g, 80% yield); the HPLC purity is more than or equal to 99.38 percent. Mass spectrum m/z: 492.0268 (theoretical value: 492.0280).
Preparation of intermediates 1 to 4:
under nitrogen protection, intermediates 1-3(140.00mmol, 69.14g), d-1(147.00mmol, 37.33g) and KOAc (420.00mmol, 41.22g) were dissolved in anhydrous dioxane (1120mL), and after nitrogen substitution, Pd (dppf) Cl was added2(2.10mmol, 1.54g) was heated under reflux for 4 hours. After the reaction was completed, it was cooled to room temperature, the mixture was poured into water, extracted with dichloromethane, and the organic layer was extracted with anhydrous MgSO4Drying and rotary evaporation are carried out, and the crude product is recrystallized by ethyl acetate. Drying afforded intermediates 1-4(59.07g, 78% yield); the HPLC purity is more than or equal to 99.44 percent. Mass spectrum m/z: 540.2015 (theoretical value: 540.2027).
Preparation of intermediates 1 to 5:
under the protection of nitrogen, intermediates 1-4(102.00mmol, 55.17g), c-1(100.00mmol, 15.70g), Pd (dppf) Cl2(1.00mmol, 0.73g), and 300mL of toluene, 100mL of ethanol were added to the reaction flask, the mixture was stirred, and then 100mL of 2M K was added2CO3Injecting the aqueous solution into the above solution by syringeThe reaction was carried out for 4 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (10: 1 recrystallization to give intermediate 1-5(36.34g, 74% yield); HPLC purity is more than or equal to 99.67%. Mass spectrum m/z: 490.1478 (theoretical value: 490.1488).
Preparation of intermediates 1 to 6:
intermediate 1-5(60.00mmol, 29.46g), d-1(63.50mmol, 16.13g) and KOAc (120.00mmol, 11.78g) were dissolved in anhydrous dioxane (500mL) under nitrogen atmosphere, and after nitrogen substitution, Pd (dppf) Cl was added2(1.05mmol, 0.77g) was heated under reflux for 5 hours. After the reaction was completed, it was cooled to room temperature, the mixture was poured into water, extracted with dichloromethane, and the organic layer was extracted with anhydrous MgSO4Drying and rotary evaporation are carried out, and the crude product is recrystallized by ethyl acetate. Drying afforded intermediates 1-6(26.21g, 75% yield); the HPLC purity is more than or equal to 99.72 percent. Mass spectrum m/z: 582.2743 (theoretical value: 582.2730).
Preparation of compound 1:
under the protection of nitrogen, intermediates 1-6(40.80mmol, 23.77g), f-1(40.00mmol, 7.92g), Pd2(dba)3(0.40mmol，0.37g)，P(t-Bu)3(3.20mmol，0.65g)，K2CO3(80.00mmol, 11.06g) and 200mL of tetrahydrofuran were added to the reaction flask, and the mixture was stirred and refluxed for 5 hours. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, and finally recrystallizing the filter cake with toluene to obtain a compound 1(16.52g, yield 72%); the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 573.2086 (theoretical value: 573.2093). Theoretical element content (%) C43H27NO: c, 90.03; h, 4.74; n, 2.44. Measured elemental content (%): c, 90.07; h, 4.72; and N, 2.43.
Synthesis example 2 Synthesis of Compound 33
Synthesis example 1 was repeated except that a-1 was replaced with equimolar a-33, c-1 was replaced with equimolar c-33, and f-1 was replaced with equimolar f-33The same preparation as in example 1 gave compound 33(17.30 g); the HPLC purity is more than or equal to 99.78 percent. Mass spectrum m/z: 600.2214 (theoretical value: 600.2202). Theoretical element content (%) C44H28N2O: c, 87.97; h, 4.70; and N, 4.66. Measured elemental content (%): c, 87.92; h, 4.72; n, 4.67.
Synthesis example 3 Synthesis of Compound 73
Compound 73(17.96g) was obtained by the same preparation method as in Synthesis example 1 except that intermediate 1-2 in Synthesis example 1 was replaced with equimolar intermediate 73-2, e-1 was replaced with equimolar e-73, and c-1 was replaced with equimolar c-73; the HPLC purity is more than or equal to 99.79 percent. Mass spectrum m/z: 623.2259 (theoretical value: 623.2249). Theoretical element content (%) C47H29NO: c, 90.50; h, 4.69; and N, 2.25. Measured elemental content (%): c, 90.55; h, 4.67; and N, 2.24.
Synthesis example 4 Synthesis of Compound 79
Compound 79(20.35g) was obtained in the same manner as in Synthesis example 1 except that b-1 in Synthesis example 1 was replaced with equimolar b-73, c-1 was replaced with equimolar c-79, and f-1 was replaced with equimolar f-33; the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z: 726.2664 (theoretical value: 726.2671). Theoretical element content (%) C54H34N2O: c, 89.23; h, 4.71; and N, 3.85. Measured elemental content (%): c, 89.21; h, 4.75; n, 3.84.
Synthesis example 5 Synthesis of Compound 96
Substitution of a-1 in Synthesis example 1Compound 96(17.09g) was obtained according to the same preparation method as that of Synthesis example 1, except that a-33 was used in an equimolar amount, b-1 was replaced with b-73 in an equimolar amount, c-1 was replaced with c-96 in an equimolar amount, and f-1 was replaced with f-33 in an equimolar amount; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 601.2166 (theoretical value: 601.2154). Theoretical element content (%) C43H27N3O: c, 85.83; h, 4.52; and N, 6.98. Measured elemental content (%): c, 85.87; h, 4.49; and N, 6.72.
Synthesis example 6 Synthesis of Compound 101
Compound 101(21.19g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-33, b-1 was replaced with equimolar b-73, c-1 was replaced with equimolar c-101, and f-1 was replaced with equimolar f-33; the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z: 767.2589 (theoretical value: 767.2573). Theoretical element content (%) C55H33N3O2: c, 86.03; h, 4.33; and N, 5.47. Measured elemental content (%): c, 86.05; h, 4.34; n, 5.42.
Synthesis example 7 Synthesis of Compound 112
Compound 112(20.59g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-112, b-1 was replaced with equimolar b-112, c-1 was replaced with equimolar c-112, and f-1 was replaced with equimolar f-33; the HPLC purity is more than or equal to 99.65 percent. Mass spectrum m/z: 756.3087 (theoretical value: 756.3079). Theoretical element content (%) C56H32D4N2O: c, 88.86; h, 5.33; and N, 3.70. Measured elemental content (%): c, 88.81; h, 5.35; and N, 3.72.
Synthesis example 8 Synthesis of Compound 123
Compound 123(20.09g) was obtained in the same preparation as in Synthesis example 1, except that a-1 in Synthesis example 1 was replaced with equimolar a-123, b-1 was replaced with equimolar b-73, c-1 was replaced with equimolar c-123, and f-1 was replaced with equimolar f-123; HPLC purity is more than or equal to 99.84%. Mass spectrum m/z: 727.2637 (theoretical value: 727.2624). Theoretical element content (%) C53H33N3O: c, 87.46; h, 4.57; n, 5.77. Measured elemental content (%): c, 87.40; h, 4.59; n, 5.78.
Synthesis example 9 Synthesis of Compound 127
Compound 127(17.99g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-127, b-1 was replaced with equimolar b-73, and c-1 was replaced with equimolar c-127; the HPLC purity is more than or equal to 99.79 percent. Mass spectrum m/z: 624.2210 (theoretical value: 624.2202). Theoretical element content (%) C46H28N2O: c, 88.44; h, 4.52; and N, 4.48. Measured elemental content (%): c, 88.46; h, 4.53; n, 4.44.
Synthesis example 10 Synthesis of Compound 140
Compound 140(20.06g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-140, b-1 was replaced with equimolar b-73, and c-1 was replaced with equimolar c-140; the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 726.2684 (theoretical value: 726.2671). Theoretical element content (%) C54H34N2O: c, 89.23; h, 4.71; and N, 3.85. Measured elemental content (%)：C,89.25；H,4.72；N,3.81。
Synthesis example 11 Synthesis of Compound 160
Compound 160(18.45g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-160, b-1 was replaced with equimolar b-73, c-1 was replaced with equimolar c-73, and f-1 was replaced with equimolar f-160; the HPLC purity is more than or equal to 99.81 percent. Mass spectrum m/z: 649.2418 (theoretical value: 649.2406). Theoretical element content (%) C49H31NO: c, 90.57; h, 4.81; and N, 2.16. Measured elemental content (%): c, 90.52; h, 4.83; and N, 2.17.
Synthesis example 12 Synthesis of Compound 177
Compound 177(20.48g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-123, b-1 was replaced with equimolar b-177, c-1 was replaced with equimolar c-177, and f-1 was replaced with equimolar f-160; the HPLC purity is more than or equal to 99.79 percent. Mass spectrum m/z: 752.2837 (theoretical value: 752.2828). Theoretical element content (%) C56H36N2O: c, 89.33; h, 4.82; and N, 3.72. Measured elemental content (%): c, 89.29; h, 4.84; n, 3.73.
Synthesis example 13 Synthesis of Compound 206
Compound 206(20.82g) was obtained in the same manner as in Synthesis example 1 except that b-1 in Synthesis example 1 was replaced with equimolar b-206 and c-1 was replaced with equimolar c-206; the HPLC purity is more than or equal to 99.86 percent. Mass spectrum m/z: 776.2836 (theoretical value:776.2828). Theoretical element content (%) C58H36N2O: c, 89.66; h, 4.67; and N, 3.61. Measured elemental content (%): c, 89.60; h, 4.69; and N, 3.62.
Synthesis example 14 Synthesis of Compound 242
Compound 242(19.91g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-242, b-1 was replaced with equimolar b-242, c-1 was replaced with equimolar c-242, and f-1 was replaced with equimolar f-123; the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z: 731.2997 (theoretical value: 731.2985). Theoretical element content (%) C54H29D5N2O: c, 88.62; h, 5.37; and N, 3.83. Measured elemental content (%): c, 88.65; h, 5.39; n, 3.79.
Synthesis example 15 Synthesis of Compound 248
Compound 248(21.53g) was obtained by the same preparation method as in Synthesis example 1 except that b-1 in Synthesis example 1 was replaced with equimolar b-248, c-1 was replaced with equimolar c-248, and f-1 was replaced with equimolar f-33; the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z: 827.2948 (theoretical value: 827.2937). Theoretical element content (%) C61H37N3O: c, 88.49; h, 4.50; and N, 5.08. Measured elemental content (%): c, 88.47; h, 4.55; and N, 5.07.
Synthesis example 16 Synthesis of Compound 272
Synthesis example 1 in which a-1 was replaced with equimolar a-33, b-1 was replaced with equimolar b-272, and c-1 was replacedThe same preparation as in Synthesis example 1 was carried out for equimolar amount of c-272 to give compound 272(19.65 g); the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z: 701.2479 (theoretical value: 701.2467). Theoretical element content (%) C51H31N3O: c, 87.28; h, 4.45; and N, 5.99. Measured elemental content (%): c, 87.29; h, 4.47; and N, 5.95.
[ Synthesis example 17] Synthesis of Compound 287
Compound 287(20.36g) was obtained by the same preparation method as in Synthesis example 1, except that a-1 in Synthesis example 1 was replaced with equimolar a-287, b-1 was replaced with equimolar b-287, c-1 was replaced with equimolar c-287, and f-1 was replaced with equimolar f-33; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 716.2809 (theoretical value: 716.2828). Theoretical element content (%) C53H36N 2O: c, 88.80; h, 5.06; and N, 3.91. Measured elemental content (%): c, 88.85; h, 5.03; and N, 3.93.
Synthesis example 18 Synthesis of Compound 293
Preparation of intermediate 1-1:
under the protection of nitrogen, the raw materials a-1(346.80mmol, 94.37g), b-1(340.00mmol, 65.09g), Pd (PPh)3)4(3.40mmol, 3.93g) and 1020mL of toluene, 340mL of ethanol were added to the reaction flask, the mixture was stirred, and 340mL of 2M K was added2CO3The aqueous solution was injected into the above solution through a syringe and reacted for 2 hours under reflux. After the reaction is finished and the temperature is reduced to room temperature, filtering to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/ethanol (10: 3 recrystallization to give intermediate 1-1(102.53g, 89% yield); the HPLC purity is more than or equal to 99.16 percent. Mass spectrum m/z: 338.0873 (theoretical value: 338.0862).
Preparation of intermediates 1-2:
intermediate 1-1(280.00mmol, 94.87g), d-1(294.00mmol, 74.66g) and KOAc (840.00mmol, 82.44g) were dissolved in anhydrous dioxane (2240mL), and after nitrogen substitution, Pd (dppf) Cl was added2(4.20mmol, 3.07g) was heated under reflux for 4 hours. After the reaction was completed, it was cooled to room temperature, the mixture was poured into water, extracted with dichloromethane, and the organic layer was extracted with anhydrous MgSO4Drying and rotary evaporation are carried out, and the crude product is recrystallized by ethyl acetate. Drying afforded intermediate 1-2(106.04g, 88% yield); the HPLC purity is more than or equal to 99.25 percent. Mass spectrum m/z: 430.2112 (theoretical value: 430.2104).
Preparation of intermediate 293-3:
under the protection of nitrogen, intermediates 1-2(204.00mmol, 87.79g), e-293(100.00mmol, 27.03g), Pd (dppf) Cl2(4.00mmol, 2.93g), 600mL of toluene, 200mL of ethanol were added to the reaction flask, the mixture was stirred, and 200mL of 2M K was added2CO3The aqueous solution was injected into the above solution through a syringe and reacted at reflux temperature for 8 hours. After the reaction is finished and the temperature is reduced to room temperature, filter cakes are obtained through suction filtration, the filter cakes are washed by ethanol, and finally the filter cakes are recrystallized by toluene to obtain an intermediate 293-3(58.82g, yield 82%); the HPLC purity is more than or equal to 99.42 percent. Mass spectrum m/z: 716.2283 (theoretical value: 716.2271).
Preparation of intermediate 293-4:
intermediate 293-3(70.00mmol, 34.37g), d-1(73.50mmol, 18.66g) and KOAc (210.00mmol, 20.61g) were dissolved in anhydrous dioxane (560mL) and, after displacement with nitrogen, Pd (dppf) Cl was added2(1.05mmol, 0.77g) was heated under reflux for 5 hours. After the reaction was completed, it was cooled to room temperature, the mixture was poured into water, extracted with dichloromethane, and the organic layer was extracted with anhydrous MgSO4Drying and rotary evaporation are carried out, and the crude product is recrystallized by ethyl acetate. Drying afforded intermediate 293-4(42.46g, 75% yield); the HPLC purity is more than or equal to 99.69 percent. Mass spectrum m/z: 808.3524 (theoretical value: 808.3513).
Preparation of compound 293:
under the protection of nitrogen, intermediate 293-4(40.80mmol, 33.00g), f-1(40.00mmol, 7.92g), Pd2(dba)3(0.40mmol，0.37g)、P(t-Bu)3(3.20mmol，0.65g)，K2CO3(80.00mmol, 11.06g) and 200mL of tetrahydrofuran were charged into a reaction flask, and the mixture was stirred and refluxed for 5 hours. After the reaction is finished and the temperature is reduced to room temperature, filter cakes are obtained through suction filtration, and finally the filter cakes are recrystallized by toluene to obtain a compound 293(22.08g, the yield is 69%); the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 799.2862 (theoretical value: 799.2875). Theoretical element content (%) C61H37NO: c, 91.59; h, 4.66; n, 1.75. Measured elemental content (%): c, 91.60; h, 4.62; n, 1.74.
Synthesis example 19 Synthesis of Compound 304
Compound 304(21.01g) was obtained in the same manner as in Synthesis example 23, except that a-1 in Synthesis example 18 was replaced with equimolar a-33, b-1 was replaced with equimolar b-112, and f-1 was replaced with equimolar f-33; the HPLC purity is more than or equal to 99.86 percent. Mass spectrum m/z: 783.3365 (theoretical value: 783.3377). Theoretical element content (%) C59H29D8 NO: c, 90.39; h, 5.78; n, 1.79. Measured elemental content (%): c, 90.42; h, 5.74; n, 1.83.
Synthesis example 20 Synthesis of Compound 305
Compound 305(20.80g) was obtained by the same preparation method as in Synthesis example 23 except that a-1 in Synthesis example 23 was replaced with equimolar a-123 and f-1 was replaced with equimolar f-33; HPLC purity is more than or equal to 99.88%. Mass spectrum m/z: 775.2863 (theoretical value: 775.2875). Theoretical element content (%) C59H37NO: c, 91.33; h, 4.81; n, 1.81. Measured elemental content (%): c, 91.37; h, 4.80; and N, 1.80.
Synthesis example 21 Synthesis of Compound 328
Compound 328(20.86g) was obtained in the same manner as in Synthesis example 1 except that b-1 in Synthesis example 1 was replaced with equimolar b-328, c-1 was replaced with equimolar c-328, and f-1 was replaced with equimolar f-328; the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 766.2457 (theoretical value: 766.2443). Theoretical element content (%) C56H34N2S: c, 87.70; h, 4.47; and N, 3.65. Measured elemental content (%): c, 87.75; h, 4.45; and N, 3.64.
Synthesis example 22 Synthesis of Compound 346
Compound 346(21.32g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-238, b-1 was replaced with equimolar b-73, c-1 was replaced with equimolar c-346, and f-1 was replaced with equimolar f-328; the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z: 819.2719 (theoretical value: 819.2708). Theoretical element content (%) C59H37N3S: c, 86.42; h, 4.55; and N, 5.12. Measured elemental content (%): c, 86.44; h, 4.50; and N, 5.13.
Synthesis example 23 Synthesis of Compound 354
Compound 354(20.89g) was obtained in the same manner as in Synthesis example 1 except that a-1 in Synthesis example 1 was replaced with equimolar a-33, b-1 was replaced with equimolar b-264, c-1 was replaced with equimolar c-354, and f-1 was replaced with equimolar f-328; the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z: 767.2405 (theoretical value: 767.2395). Theoretical element content (%) C55H33N3S: c, 86.02; h, 4.33; and N, 5.47. Measured elemental content (%): c,86.04；H,4.34；N,5.42。
Synthesis example 24 Synthesis of Compound 363
Compound 363(17.74g) was obtained by the same preparation method as in Synthesis example 1 except that intermediates 1-4 in Synthesis example 1 were replaced with equimolar of intermediates 73-4, c-1 was replaced with equimolar of c-287, and f-1 was replaced with equimolar of f-363; the HPLC purity is more than or equal to 99.78 percent. Mass spectrum m/z: 624.2215 (theoretical value: 624.2202). Theoretical element content (%) C46H28N2O: c, 88.44; h, 4.52; and N, 4.48. Measured elemental content (%): c, 88.40; h, 4.53; and N, 4.49.
[ Synthesis example 25] Synthesis of Compound 374
Compound 374(18.95g) was obtained by the same preparation method as in Synthesis example 1 except that intermediate 1-4 in Synthesis example 1 was replaced with equimolar intermediate 101-4, c-1 was replaced with equimolar c-73, and f-1 was replaced with equimolar f-374; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 676.2528 (theoretical value: 676.2515). Theoretical element content (%) C50H32N2O: c, 88.73; h, 4.77; n, 4.14. Measured elemental content (%): c, 88.75; h, 4.78; and N, 4.10.
By the above preparation method, the present invention also synthesizes the following compounds, and the structural characterization of the obtained final product is shown in the following table:
EXAMPLE 33 triplet level test
Test samples: the compounds prepared in the synthesis examples of the present invention and comparative compounds 1 to 3.
Testing an instrument: fluorescence spectrophotometer (Hitachi F-4600).
And (3) testing conditions are as follows: toluene as solvent with concentration of 2X 10-5mol/L, temperature-78 ℃. The triplet state energy level (T) is obtained by calculation1) The calculation results are shown in table 1:
EXAMPLE 34 glass transition temperature test
Test samples: the compounds prepared in the synthesis examples of the present invention and comparative compounds 1 to 4.
Testing an instrument: DSC 25 type differential scanning calorimeter (TA, USA);
and (3) testing conditions are as follows: the test atmosphere is nitrogen, and the flow rate of the nitrogen is 50 mL/min; the heating rate is 10 ℃/min, and the temperature range is 50-350 ℃. The glass transition temperature (Tg) test results are shown in table 1:
table 1:
as can be seen from Table 1, the compound of the present invention has higher glass transition temperature, improved thermal stability and film forming property compared with comparative compound 1, comparative compound 2 and comparative compound 4, and can prolong the service life of the device when applied to the organic electroluminescent device; on the other hand, compared with the comparative compounds 1-3, the compound provided by the invention has a higher triplet state energy level, can effectively block excitons in a light-emitting layer, and can effectively improve the light-emitting efficiency of the device and prolong the service life of the device when being applied to an organic electroluminescent device, particularly as an electron transport layer or a hole blocking layer.
[ comparative example 1]
Taking the ITO-evaporated glass substrate as an anode, ultrasonically cleaning the ITO-evaporated glass substrate for 2 times by 5% glass cleaning solution for 20 minutes each time, and ultrasonically cleaning the ITO-evaporated glass substrate for 2 times by deionized water for 10 minutes each time. Ultrasonic cleaning is carried out for 20 minutes by using acetone and isopropyl alcohol in sequence, drying is carried out at 120 ℃, and then the substrate is transferred to an evaporation machine.
The following compounds are sequentially evaporated on an ITO glass substrate to prepare an organic electroluminescent device, a compound m-MTDATA is evaporated to be used as a hole injection layer, the evaporation thickness is 10nm, a compound NPB is evaporated to be used as a first hole transport layer, the evaporation thickness is 95nm, HT-2 is evaporated to be used as a second hole transport layer, the evaporation thickness is 15nm, alpha, beta-ADN is used as a main body, BD-1 is used as a doping material, the doping ratio of the alpha to the beta-ADN to the BD-1 is 98:2 to form a light emitting layer with the thickness of 22nm, the comparison compound 1 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form an electron transport layer with the thickness of 30nm, LiQ is evaporated to be used as an electron injection layer, the evaporation thickness is 1nm, then Al is evaporated to be used as a cathode, and the evaporation thickness is 120 nm.
Comparative examples 2 to 3
Organic electroluminescent devices were prepared in the same manner as in comparative example 1, using comparative compound 2 and comparative compound 3 instead of comparative compound 1 in comparative example 1 as the electron transport layer.
Device examples 1 to 20
An organic electroluminescent device was produced in the same production manner as in comparative example 1, using compound 1, compound 33, compound 73, compound 96, compound 101, compound 112, compound 123, compound 127, compound 140, compound 160, compound 177, compound 206, compound 242, compound 248, compound 272, compound 287, compound 328, compound 346, compound 354, compound 363 of the present invention instead of comparative compound 1 in comparative example 1 as the electron transport layer.
[ comparative example 4]
The following compounds are sequentially evaporated on an ITO glass substrate to prepare an organic electroluminescent device, a compound m-MTDATA is evaporated to be used as a hole injection layer, the evaporation thickness is 10nm, a compound NPB is evaporated to be used as a first hole transport layer, the evaporation thickness is 95nm, HT-2 is evaporated to be used as a second hole transport layer, the evaporation thickness is 15nm, alpha, beta-ADN is used as a main body, BD-1 is used as a doping material, the doping ratio of the alpha to the beta-ADN to the BD-1 is 98:2 to form a light emitting layer with the thickness of 22nm, a comparative compound 1 is evaporated to be used as a hole blocking layer, the evaporation thickness is 5nm, ET-1 and LiQ are mixed and evaporated to form an electron transport layer with the thickness of 30nm in a weight ratio of 1:1, LiQ is evaporated to be used as an electron injection layer, the evaporation thickness is 1nm, Al is evaporated to be used as a cathode, and the evaporation thickness is 120 nm.
[ comparative example 5]
An organic electroluminescent device was produced in the same manner as in comparative example 4, using comparative compound 2 instead of comparative compound 1 in comparative example 4 as the hole blocking layer.
Device examples 21 to 35
An organic electroluminescent device was produced in the same production manner as in comparative example 4, using compound 1, compound 73, compound 79, compound 101, compound 112, compound 123, compound 127, compound 140, compound 177, compound 206, compound 248, compound 272, compound 328, compound 354, compound 374 according to the present invention as a hole blocking layer instead of comparative compound 1 in comparative example 4. The results of the light emission characteristic test of the obtained organic electroluminescent device are shown in table 2.
The test software, computer, K2400 digital source meter manufactured by Keithley corporation, usa, and PR788 spectral scanning luminance meter manufactured by Photo Research corporation, usa were combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature. The results of the light emission characteristic test of the obtained organic electroluminescent device are shown in table 2.
Table 2:
as can be seen from the data in table 2, when the compound of the present invention is applied to an organic electroluminescent device, the light emitting efficiency of the device can be improved, and the lifetime of the device can be prolonged, especially when the compound of the present invention has a twisted structure, the light emitting efficiency and the lifetime are further improved.
[ comparative example 6]
An organic electroluminescent device was prepared by sequentially vapor-depositing m-MTDATA as a hole injection layer and 10nm in thickness on an ITO/Ag/ITO glass substrate, then NPB as a first hole transport layer and 95nm in thickness, HT-2 as a second hole transport layer and 15nm in thickness, α, β -ADN as a host and BD-1 as a dopant at a doping ratio of 98:2 to form a light-emitting layer 22nm in thickness, then mixing 1 and LiQ in a weight ratio of 1:1 and vapor-depositing to form an electron transport layer 30nm in thickness, then LiQ as an electron injection layer and 1nm in thickness, then mixing magnesium (Mg) and silver (Ag) at a vapor deposition rate of 1:9, vacuum-depositing on the electron injection layer to form a cathode 13nm in thickness, then, comparative compound 5 was evaporated as a cap layer to a thickness of 70 nm.
Device examples 36 to 45
An organic electroluminescent device was produced in the same production manner as in comparative example 6, except that compound 293, compound 296, compound 301, compound 304, compound 305, compound 307, compound 310, compound 312, compound 313 and compound 315 of the present invention were used as a capping layer in place of comparative compound 4 in comparative example 6. The light emitting characteristics of the resulting organic electroluminescent devices were measured as above, and the results are shown in table 3.
Table 3:
as can be seen from table 3, when the compound of the present invention is applied to the capping layer of the organic electroluminescent device, the compound of the present invention has higher refractive index and glass transition temperature than the comparative compound 4, and thus has good thermal stability, film-forming property and light-emitting rate during vapor deposition, and can effectively improve the light extraction efficiency of the device, thereby improving the light-emitting efficiency of the device.
It should be noted that while the invention has been particularly described in terms of particular embodiments, it will be apparent to those skilled in the art that numerous changes and modifications can be made without departing from the principles of the invention, and it is intended to cover such changes and modifications as fall within the scope of the invention.
Claims (10)
1. A compound comprising a fused aryl group, wherein the compound has a structure represented by formula 1:
in chemical formula 1, the a are the same as or different from each other and are selected from the group consisting of no, substituted or unsubstituted phenyl, and at least one a is selected from the group consisting of substituted or unsubstituted phenyl;
c is selected from the group represented by chemical formula 2;
the B is different from the C and is not a group represented by chemical formula 2, the B is selected from any one of substituted or unsubstituted C3-C12 naphthenic base, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl or combination thereof,
x is selected from any one of O, S;
said L0Is selected from substituted or unsubstituted arylene of C6-C30;
said L1、L2Any one of a single bond, a substituted or unsubstituted arylene group having C6-C30 groups, and a substituted or unsubstituted heteroarylene group having C2-C30 groups, which are the same or different from each other;
the R is0、R1、R2The same or different from each other, and are independently selected from hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 naphtheneAny one of a substituted or unsubstituted aryl group having C6-C30 and a substituted or unsubstituted heteroaryl group having C2-C30;
n is0Independently selected from 0, 1, 2, 3 or 4, said n1Is selected from 0, 1, 2, 3, 4 or 5, the n2Selected from 0, 1, 2 or 3, when n is0、n1、n2Greater than 1, two or more R0、R1、R2Two R's, equal to or different from each other, or adjacent1May be linked to form a substituted or unsubstituted ring.
2. The compound of claim 1, wherein the compound is selected from any one of the structures of formula 1-1 to formula 1-3:
the R is0The aryl group is any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C18 heteroaryl;
m is1Is selected from 0, 1, 2, 3 or 4, m2Is selected from 0, 1, 2 or 3, m3Selected from 0, 1 or 2.
3. The fused aryl containing compound of claim 1, wherein L is0Any one selected from the following groups:
each Rn is independently any one of hydrogen, deuterium, cyano, C1-C4 alkyl, C3-C12 cycloalkyl, C6-C12 aryl and C2-C12 heteroaryl;
b is1Selected from 0, 1, 2, 3 or 4, said b2Selected from 0, 1, 2 or 3, said b3Selected from 0, 1 or 2, said b4Selected from 0, 1, 2, 3, 4 or 5.
4. The compound of claim 1, wherein B is selected from any one of the following groups:
y is selected from C (Rm) or N atom, and at least one Y in each of C-1 to C-6 is selected from N atom;
said X1Selected from O, S, C (Ry)2Any one of the above;
the Ry is any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Ry can be connected to form a substituted or unsubstituted ring;
each Rm is independently any one selected from hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C12 alkyl 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, or two adjacent Rms can be connected to form a substituted or unsubstituted ring;
a is a1Selected from 0, 1, 2, 3, 4 or 5, said a2Selected from 0, 1, 2, 3 or 4, said a3Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a4Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a5Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10 or 11.
5. The compound of claim 1, wherein B is selected from any one of the following groups:
6. the fused aryl containing compound of claim 1, wherein L is1、L2The same or different from each other are selected from a single bond or any one of the following groups:
each Z is independently selected from a C (rz) or N atom; and
the bonded Z is a C atom;
said X2Selected from O atoms, S atoms or C (Rx)2Any one of the above; the Rz is independently any one selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Rz can be connected to form a substituted or unsubstituted ring;
the Rx are the same or different from each other, and any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two Rx can be connected to form a substituted or unsubstituted ring.
7. The compound of claim 1, wherein C is selected from any one of the following groups:
8. the fused aryl containing compound of claim 1, selected from any one of the following structures:
9. an organic electroluminescent device comprising an anode, a cathode, an organic layer between the anode and the cathode, and/or a cover layer on the outside of at least one of the anode and the cathode, characterized in that at least one of the organic layer or the cover layer comprises at least one of the compounds comprising a thick aryl group of any one of claims 1 to 8.
10. An organic electroluminescent device according to claim 9, wherein the organic layer comprises at least one of an electron transport layer or a hole blocking layer, and the at least one of an electron transport layer or a hole blocking layer comprises at least one of the compounds containing a condensed aromatic group according to any one of claims 1 to 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111131667.1A CN113735794B (en) | 2021-09-26 | 2021-09-26 | Compound containing condensed aryl and organic electroluminescent device thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111131667.1A CN113735794B (en) | 2021-09-26 | 2021-09-26 | Compound containing condensed aryl and organic electroluminescent device thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113735794A true CN113735794A (en) | 2021-12-03 |
| CN113735794B CN113735794B (en) | 2023-11-28 |
Family
ID=78741246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111131667.1A Active CN113735794B (en) | 2021-09-26 | 2021-09-26 | Compound containing condensed aryl and organic electroluminescent device thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113735794B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114149361A (en) * | 2021-12-17 | 2022-03-08 | 长春海谱润斯科技股份有限公司 | Heterocyclic derivative and organic electroluminescent device thereof |
| CN114805013A (en) * | 2022-07-01 | 2022-07-29 | 江苏欣诺科催化剂有限公司 | Synthesis method of halogenated biaryl compound |
| CN115073440A (en) * | 2022-07-21 | 2022-09-20 | 长春海谱润斯科技股份有限公司 | Compound with benzoxazole ring and organic electroluminescent device thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101575259A (en) * | 2007-12-04 | 2009-11-11 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN111138342A (en) * | 2018-11-05 | 2020-05-12 | 乐金显示有限公司 | Novel compound and organic electroluminescent device comprising same |
| CN113336744A (en) * | 2021-06-23 | 2021-09-03 | 长春海谱润斯科技股份有限公司 | Heterocyclic derivative and organic electroluminescent device thereof |
-
2021
- 2021-09-26 CN CN202111131667.1A patent/CN113735794B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101575259A (en) * | 2007-12-04 | 2009-11-11 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN111138342A (en) * | 2018-11-05 | 2020-05-12 | 乐金显示有限公司 | Novel compound and organic electroluminescent device comprising same |
| CN113336744A (en) * | 2021-06-23 | 2021-09-03 | 长春海谱润斯科技股份有限公司 | Heterocyclic derivative and organic electroluminescent device thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114149361A (en) * | 2021-12-17 | 2022-03-08 | 长春海谱润斯科技股份有限公司 | Heterocyclic derivative and organic electroluminescent device thereof |
| CN114149361B (en) * | 2021-12-17 | 2024-01-26 | 长春海谱润斯科技股份有限公司 | Heterocyclic derivative and organic electroluminescent device thereof |
| CN114805013A (en) * | 2022-07-01 | 2022-07-29 | 江苏欣诺科催化剂有限公司 | Synthesis method of halogenated biaryl compound |
| CN114805013B (en) * | 2022-07-01 | 2022-09-27 | 江苏欣诺科催化剂有限公司 | Synthesis method of halogenated biaryl compound |
| CN115073440A (en) * | 2022-07-21 | 2022-09-20 | 长春海谱润斯科技股份有限公司 | Compound with benzoxazole ring and organic electroluminescent device thereof |
| CN115073440B (en) * | 2022-07-21 | 2024-05-14 | 长春海谱润斯科技股份有限公司 | Compound with benzoxazole ring and organic electroluminescent device thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113735794B (en) | 2023-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113372313B (en) | Triarylamine compound and organic electroluminescent device thereof | |
| CN112661714B (en) | Heterocyclic compound and organic electroluminescent device containing same | |
| KR102258084B1 (en) | Composition for optoelectronic device and organic optoelectronic device and display device | |
| EP2796529B1 (en) | Compound for an organic optoelectronic device, organic light-emitting element comprising same, and display device comprising the organic light-emitting element | |
| CN113735794B (en) | Compound containing condensed aryl and organic electroluminescent device thereof | |
| CN112521360B (en) | Arylamine organic compound and organic electroluminescent device thereof | |
| CN113735793B (en) | Compound containing benzo five-membered heterocycle and organic electroluminescent device thereof | |
| CN110964002A (en) | Arylamine derivative and organic light-emitting device thereof | |
| WO2021140896A1 (en) | Organic electroluminescence element | |
| KR20210129999A (en) | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device | |
| CN113717058A (en) | Triarylamine compound containing fluorene derivative group and organic electroluminescent device thereof | |
| CN111116505A (en) | Amine compound and organic light-emitting device thereof | |
| CN114436942A (en) | Arylamine compound containing carbazole group and organic electroluminescent device thereof | |
| CN114634419A (en) | Aromatic amine compound and organic electroluminescent device thereof | |
| TW201332943A (en) | Aromatic amine derivative and organic electroluminescence device using same | |
| CN115417806B (en) | Carbazole compound and organic electroluminescent device thereof | |
| CN117164535A (en) | Fluorene group-containing compound and organic electroluminescent device thereof | |
| CN117126149A (en) | Heterocyclic compound and organic electroluminescent device thereof | |
| CN113717196B (en) | Azabenzoxazole or thiazole compound and organic electroluminescent device thereof | |
| CN115745906A (en) | Compound containing heterocycle and organic electroluminescent device thereof | |
| CN114122288A (en) | Organic electroluminescent device comprising light extraction layer | |
| CN113594393B (en) | Organic electroluminescent device | |
| KR102586096B1 (en) | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device | |
| CN115583943A (en) | Compound containing fused aromatic ring and organic electroluminescent device thereof | |
| CN114149361A (en) | Heterocyclic derivative and organic electroluminescent device thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |