CN117143134A - Bicarbazole compound and organic electroluminescent device thereof - Google Patents
Bicarbazole compound and organic electroluminescent device thereof Download PDFInfo
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- CN117143134A CN117143134A CN202311092231.5A CN202311092231A CN117143134A CN 117143134 A CN117143134 A CN 117143134A CN 202311092231 A CN202311092231 A CN 202311092231A CN 117143134 A CN117143134 A CN 117143134A
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- deuterium
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 124
- 239000010410 layer Substances 0.000 claims description 98
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 50
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 48
- 229910052805 deuterium Inorganic materials 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000004305 biphenyl Substances 0.000 claims description 30
- 235000010290 biphenyl Nutrition 0.000 claims description 29
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 22
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 15
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 14
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 91
- 238000003786 synthesis reaction Methods 0.000 description 91
- 238000002360 preparation method Methods 0.000 description 65
- 238000001819 mass spectrum Methods 0.000 description 53
- 238000004128 high performance liquid chromatography Methods 0.000 description 52
- 239000000463 material Substances 0.000 description 48
- 238000004519 manufacturing process Methods 0.000 description 42
- -1 alicyclic hydrocarbon Chemical class 0.000 description 38
- 239000000543 intermediate Substances 0.000 description 29
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229940125782 compound 2 Drugs 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 6
- 229910052722 tritium Inorganic materials 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 3
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 3
- 241000720974 Protium Species 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 2
- GWNJZSGBZMLRBW-UHFFFAOYSA-N 9,10-dinaphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 GWNJZSGBZMLRBW-UHFFFAOYSA-N 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 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
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- SHNBXKOUKNSCSQ-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 SHNBXKOUKNSCSQ-UHFFFAOYSA-N 0.000 description 1
- DBNYWRKRZTXMCU-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 DBNYWRKRZTXMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004626 naphthothienyl group Chemical group C1(=CSC2=C1C1=CC=CC=C1C=C2)* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- DVDUMIQZEUTAGK-UHFFFAOYSA-N p-nitrophenyl butyrate Chemical compound CCCC(=O)OC1=CC=C([N+]([O-])=O)C=C1 DVDUMIQZEUTAGK-UHFFFAOYSA-N 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 108091008695 photoreceptors Proteins 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
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- 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
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- 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
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- 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
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- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
The invention provides a dicarbazole compound and an organic electroluminescent device thereof, belonging to the technical field of organic electroluminescent. The dicarbazole compound provided by the invention has proper HOMO energy level and triplet energy gap, can enable the interior of the device to have higher internal quantum efficiency, further improves the luminous efficiency of the organic electroluminescent device, has good thermal stability, and can further prolong the service life of the device when being applied to the organic electroluminescent device. The dicarbazole compound and the organic electroluminescent device thereof have good application effect and industrialization prospect.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a dicarbazole compound and an organic electroluminescent device thereof.
Background
An Organic Light-Emitting Diode (OLED) is used as a new generation display technology, and has the advantages of ultra-thin, self-luminescence, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and has been widely used in industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
The organic electroluminescence phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electroluminescent device utilizing an organic electroluminescent phenomenon generally has the following structure: an anode, a cathode, and an organic material layer between or outside the anode and the cathode. The organic material layer is generally formed in a multi-layered structure composed of different materials to improve brightness, efficiency, and lifetime of the organic electroluminescent device, and may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a capping layer, and the like.
At present, 4'-N, N' -dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material, and Pioneer electronics (pineer) (japan) and the like use Bathocuproine (BCP) called a hole blocking material, aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) and the like as host materials, and have good performance as well. However, while conventional materials provide good luminescence characteristics, they have the following drawbacks: (1) Degradation occurs during the high temperature deposition process in vacuum and shortens the lifetime of the device. (2) The luminous efficiency still cannot meet the requirement of a large-area display.
In the existing organic electroluminescent devices, the most important problems are lifetime and efficiency, along with the large area of the display, the driving voltage is increased, the luminous efficiency is also increased, and a certain service life is ensured, so that it is necessary to continuously develop a novel organic electroluminescent material to further improve the performance of the organic electroluminescent device.
Disclosure of Invention
In order to further improve the performance of the organic electroluminescent device and enable the organic electroluminescent device to be suitable for the large area of a display, the invention provides a dicarbazole compound and the organic electroluminescent device thereof, and the dicarbazole compound has the advantages ofHigh stability, and the compounds have higher HOMO energy level and triplet energy gap (E T ) When the light-emitting diode is applied to an organic electroluminescent device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be prolonged.
The invention provides a dicarbazole compound, which is characterized in that the dicarbazole compound has a structure shown in a chemical formula 1,
the x are the same or different and are selected from CR 3 Or N, wherein is the same as the Ar 0 、L 0 The bonded x is selected from C;
the R is 3 Any one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl, or adjacent R 3 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other;
the Ar is as follows 0 Selected from the group consisting of the structures shown in chemical formula 2,
the z are the same or different and are selected from CR 2 Or N;
the R is 1 、R 2 The same or different is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl, or adjacent R 2 Are connected with each other to form a substituted or unsubstituted ring;
the L is 0 、L 1 、L 2 The same or different arylene groups are selected from any one of single bonds, substituted or unsubstituted C6-C24 arylene groups, substituted or unsubstituted C2-C25 heteroarylene groups and substituted or unsubstituted C3-C12 alicyclic groups;
the Ar is as follows 1 、Ar 2 The same or different aryl groups are selected from any one of substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C24 aryl groups, substituted or unsubstituted C2-C25 heteroaryl groups and substituted or unsubstituted silyl groups;
at least one group of the chemical formula 1 is bonded to Si (R 4 ) 3 Substitution, said R 4 The same or different one is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C12 heteroaryl.
The invention also provides an organic electroluminescent device, which comprises an anode, an organic layer and a cathode, wherein the organic layer comprises one or a combination of at least two of the dicarbazole compounds.
The invention has the beneficial effects that:
the dicarbazole compound provided by the invention has higher HOMO energy level and triplet energy gap (E) T ) The material has good thermal stability and an amorphous state, so that when the dicarbazole compound provided by the invention is applied to an organic electroluminescent device, the luminous efficiency of the device can be effectively improved, and the service life of the device is prolonged.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. It will be apparent that the described embodiments are some, but not all, embodiments of the invention. And embodiments of the invention and features of the embodiments may be combined with each other without conflict. All other embodiments, which can be made by a person skilled in the art without creative efforts, based on the described embodiments of the present invention fall within the protection scope of the present invention.
Unless defined otherwise, technical or scientific terms used herein should be given the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance.
In the present specification, "-" means a moiety attached to another substituent.
In this specification, when a substituent is not fixed in position on a ring, it is meant that it can be attached to any of the corresponding selectable positions of the ring. For example, the number of the cells to be processed,can indicate-> Can represent Can represent And so on.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For exampleCan indicate-> Can indicate-> Can indicate-> And so on.
Halogen refers to fluorine, chlorine, bromine and iodine;
the alkyl group according to the present invention means a monovalent group obtained by removing one hydrogen atom from an alkane molecule, and may be a straight chain alkyl group, a branched chain alkyl group, preferably having 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms, and examples may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.
The alicyclic group according to the present invention means a monovalent group obtained by removing at least one hydrogen atom from an alicyclic hydrocarbon molecule, and may be a cycloalkyl group, a cycloalkenyl group, etc., preferably having 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, most preferably 3 to 7 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.
The aryl group according to the present invention means a monovalent group obtained by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group, a polycyclic aryl group or a condensed ring aryl group, preferably having 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and examples may include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, indenyl, indanyl, dihydronaphthyl, tetrahydronaphthyl, anthracenyl, phenanthryl, pyrenyl, triphenylenyl, perylenyl, and the like, but are not limited thereto.
Heteroaryl according to the present invention refers to a generic term for a monovalent group left by removing one hydrogen atom from the core carbon of an aromatic heterocycle composed of carbon and heteroatoms, which may be one or more of N, O, S, and may be a monocyclic heteroaryl, polycyclic heteroaryl or fused ring heteroaryl, preferably having 3 to 30 carbon atoms, preferably having 3 to 22 carbon atoms, more preferably having 3 to 16 carbon atoms, most preferably 3 to 8 carbon atoms, and examples may include pyridyl, pyrimidinyl, triazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, indolyl, pyridofuryl, pyridothienyl, pyridopyrrolyl, pyrimidofuranyl, pyrimidothienyl, naphthothienyl, phenanthrofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzonaphthatyl, benzonaphthathioyl, naphthazolyl, benzoxazolyl, thiazolyl, benzoxazolyl, oxazolyl, thiazolyl, oxazolyl, etc.
In the present specification, the "substituted or unsubstituted silyl group" means-Si (R k ) 3 A group wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 ringAlkyl, substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C2-C60, fused cyclic groups of substituted or unsubstituted alicyclic C3-C30 and aromatic C6-C60, and fused cyclic groups of substituted or unsubstituted alicyclic C3-C30 and heteroaromatic C2-C60. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl.
The arylene group refers to a bivalent group formed by removing two hydrogen atoms from the aromatic nucleus carbon of an aromatic hydrocarbon molecule. These are not only divalent groups but also aryl groups as described above.
The heteroarylene group according to the present invention is a divalent group obtained by removing two hydrogen atoms from the nuclear carbon of an aromatic heterocycle comprising carbon and a heteroatom. These are, in addition to the divalent radicals, in each case, suitable for the description of heteroaryl radicals given above.
"substituted" as used herein means that a hydrogen atom in a compound group is replaced with another atom or group, and the position of substitution is not limited.
The term "substituted or unsubstituted" as used herein means that one or more selected from the group consisting ofSubstitution of substituents: protium, deuterium, tritium, cyano, halogen atom, amino, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic group and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl group and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C6-C30 aryloxy group, preferably protium, deuterium, tritium, halogen atom, cyano, C1-C12 alkyl, C3-C18 alicyclic, C6-C25 aryl, C2-C25 heteroaryl, specific examples may include protium, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, trifluoromethyl, phenyl, tolyl, mesityl, penta-phenyl, pentafluorophenyl, biphenyl, naphthyl, anthryl, phenanthryl, benzophenyl, pyrenyl, triphenylenyl, deutero-phenyl, A group, perylene group, fluoranthenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, carbazolyl group, 9-phenylcarbazolyl group, spirobifluorenyl group, carbazoloindolyl group, pyrrolyl group, furanyl group, thienyl group, indolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, oxazolyl group, thiazolyl group, imidazolyl group, benzoxazolyl group, benzothiazolyl group, benzotriazolyl group, benzimidazolyl group, pyridooxazolyl group, pyridothiazolyl group, pyridoimidazolyl group, pyrimidoxazolyl group, pyrimidothiazolyl group, pyrimidoimidazolyl group, quinolino oxazolyl group, quinolyl group, quinolizinyl group, quinolyl groupPhenothiazinyl, phenoxazinyl, acridinyl, and the like, but is not limited thereto. Or when the substituents are two or more, adjacent substituents may be bonded to form a ring; when the substituents are two or more, the two or more substituents are the same or different from each other.
In the present invention, "adjacent two groups are linked to form a ring" means that a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle is formed by bonding adjacent groups to each other and optionally aromatizing. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may include aliphatic or aromatic heterocycles. The aliphatic hydrocarbon ring may be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring may be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may be a single ring or a polycyclic group. In addition, a ring formed by bonding adjacent groups may be linked to another ring to form a spiro structure. As exemplified below:
In the present specification, the ring formed by the connection may be an aromatic ring or a non-aromatic ring, and may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, or the like, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, or the like, but is not limited thereto.
Embodiments of the organic electroluminescent device according to the present invention will be described below, but the embodiments of the present invention may be modified into other forms, and the scope of the present invention is not limited to the embodiments described below.
In describing the structural elements of the present invention, the use of the terms "comprising" or "comprises" and the like in the present invention means that the device or article preceding the term encompasses the device or article listed after the term and equivalents thereof without excluding other devices or articles. The terms "connected" or "connected," and the like, are not limited to physical or mechanical connections, but may include electrical connections, whether direct or indirect. "inner", "outer", "upper", "lower" and the like are used merely to indicate relative positional relationships, which may also be changed when the absolute positions of the structural elements being described are changed. In the case where a structural element such as a layer, a film, a region, or a plate is located "on" another structural element, it is understood that the structural element is located "directly above" the other structural element, and that the structural element is located in the middle. In contrast, when one structural element is located "directly above" another structural element, it is understood that there are no other structural elements in between.
The term "at least one" in the present invention includes one, two, three, four, five or more.
The term "one or more" in the present invention includes one, two, three, four, five or more.
The invention provides a dicarbazole compound, which has a structure shown in a chemical formula 1,
the x are the same or different and are selected from CR 3 Or N, wherein is the same as the Ar 0 、L 0 The bonded x is selected from C;
the R is 3 Any one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl, or adjacent R 3 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other;
the Ar is as follows 0 Selected from the group consisting of the structures shown in chemical formula 2,
the z are the same or different and are selected from CR 2 Or N;
the R is 1 、R 2 The same or different is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl, or adjacent R 2 Are connected with each other to form a substituted or unsubstituted ring;
the L is 0 、L 1 、L 2 The same or different arylene groups are selected from any one of single bonds, substituted or unsubstituted C6-C24 arylene groups, substituted or unsubstituted C2-C25 heteroarylene groups and substituted or unsubstituted C3-C12 alicyclic groups;
the Ar is as follows 1 、Ar 2 The same or different aryl groups are selected from any one of substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C24 aryl groups, substituted or unsubstituted C2-C25 heteroaryl groups and substituted or unsubstituted silyl groups;
at least one group of the chemical formula 1 is bonded to Si (R 4 ) 3 Substitution, said R 4 The same or different one is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C12 heteroaryl.
Preferably, the chemical formula 1 has a structure represented by the following chemical formula 1-1 or chemical formula 1-2,
preferably, the L 1 、L 2 、Ar 1 、Ar 2 、L 0 、Ar 0 At least one of the groups is Si (R) 4 ) 3 Substitution;
more preferably, the L 1 、L 2 、Ar 1 、Ar 2 、L 0 、Ar 0 One, two, three, four, five or six groups of (A) are Si (R) 4 ) 3 Substitution;
more preferably, the L 1 、L 2 、Ar 1 、Ar 2 At least one of the groups is Si (R) 4 ) 3 Substitution;
more preferably, the L 1 、L 2 、Ar 1 、Ar 2 One, two, three or four groups of (A) are Si (R) 4 ) 3 Substitution;
further preferably, the Ar 1 、Ar 2 At least one of the groups is Si (R) 4 ) 3 Substitution;
most preferably, the Ar 1 、Ar 2 One or both groups of (B) are Si (R) 4 ) 3 Substitution;
preferably, said R 4 The same or different groups are selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl and pyrimidinyl;
the R is 4 May be substituted with one or more substituents selected from any one of deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, or a combination thereof; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, the Si (R 4 ) 3 Selected from any one of the structures shown below,
preferably, the method comprises the steps of,the Ar is as follows 0 Selected from any one of the structures shown below,
the a 1 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the a 2 Selected from 1, 2, 3, 4, 5, 6 or 7; the a 3 Selected from 1, 2, 3, 4, 5 or 6; the a 4 Selected from 1, 2, 3, 4 or 5; the a 5 Selected from 1, 2, 3 or 4; when two or more R's are present 2 When two or more R' s 2 Are the same as or different from each other.
Preferably, R is as described in the present invention 2 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 2 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, R is as described in the present invention 1 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, gold Rigid alkyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 1 May be substituted with one or more substituents R 11 Substituted, the substituent R 11 Selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, trimethylsilyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, when Si (R 4 ) 3 Substituted for Ar 0 When in the above, it replaces R of corresponding quantity 11 And/or R 2 。
Preferably, R 11 One, two or more of them are selected from Si (R 4 ) 3 。
Preferably, R 2 One, two or more of them are selected from Si (R 4 ) 3 。
Preferably, the Ar 1 、Ar 2 The same or different are selected from Si (R) 4 ) 3 Or any one of the structures shown below,
the v is the same or different and is selected from CH or N;
said Y is selected from O, S, C (Ra) 2 Any one of N (Rb);
the Ra is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Ra can be Directly with L 1 And/or L 2 Connecting;
the Rb is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Rb can be directly combined with L 1 And/or L 2 Connecting;
the R is 5 The same or different one is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl;
said n 1 Selected from 1, 2, 3, 4 or 5; said n 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said n 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said n 5 Selected from 1, 2, 3, 4, 5 or 6; when two or more R's are present 5 When two or more R' s 5 Are identical or different from each other, or adjacent R 5 Are linked to each other to form a substituted or unsubstituted ring.
Preferably, the Ar 1 、Ar 2 The same or different are selected from Si (R) 4 ) 3 Or any one of the structures shown below,
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the R is 5 The same or different groups are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, and,Biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 5 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other;
said n 1 Selected from 1, 2, 3, 4 or 5; said n 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said n 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said n 5 Selected from 1, 2, 3, 4, 5 or 6; said n 6 Selected from 1, 2, 3 or 4; said n 7 Selected from 1, 2 or 3; said n 8 Selected from 1 or 2; said n 9 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said n 10 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R's are present 5 When two or more R' s 5 Are the same as or different from each other.
Preferably, when Si (R 4 ) 3 Substituted for Ar 1 、Ar 2 When in the above, it replaces R of corresponding quantity 5 。
Preferably, R 5 One, two, three, four or more of them are selected from Si (R 4 ) 3 。
More preferably, ar 1 R of (2) 5 One or both of them are selected from Si (R 4 ) 3 。
More preferably, ar 2 R of (2) 5 One or both of them are selected from Si (R 4 ) 3 。
More preferably, ar 1 R of (2) 5 One or both of Ar 2 R of (2) 5 One or two of 0 are selected from Si (R 4 ) 3 . Or Ar 1 R of (2) 5 0, one or two of (a) and Ar 2 R of (2) 5 One or both of them are selected from Si (R 4 ) 3 。
Preferably, the L 0 、L 1 、L 2 The same or different is selected from single bond or any one of the structures shown below,
the u are the same or different and are selected from CH or N;
said E is selected from O, S, C (Rc) 2 Any one of N (Rd);
the Rc is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Rc can be directly combined with Ar 1 And/or Ar 2 And/or an x-connection;
the Rd is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Rb can be directly combined with Ar 1 And/or Ar 2 And/or an x-connection;
the R is 6 The same or different one is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl;
the m is 1 Selected from 1, 2, 3 or 4; the m is 2 Selected from 1, 2, 3, 4, 5 or 6; the m is 3 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m is 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the m is 5 Selected from 1, 2 or 3; the m is 6 Selected from 1 or 2; the m is 7 Selected from 1, 2, 3, 4 or 5; when two or more R's are present 6 When two or more R' s 6 Are identical or different from each other, or adjacent R 6 Are linked to each other to form a substituted or unsubstituted ring.
Preferably, the L 0 、L 1 、L 2 The same or different is selected from single bond or any one of the structures shown below,
said E is selected from O, S, C (Rc) 2 Any one of N (Rd);
the Rc is the same or different and is selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any of the above, rc may be directly bonded to Ar 1 And/or Ar 2 And/or an x-connection;
the Rc may be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, tert-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other;
the Rd is selected from methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any of the Rd may be directly with Ar 1 And/or Ar 2 And/or an x-connection;
the Rd may be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methylIsopropyl, tert-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other;
the R is 6 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 6 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other;
The m is 1 Selected from 1, 2, 3 or 4; the m is 2 Selected from 1, 2, 3, 4, 5 or 6; the m is 3 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m is 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the m is 5 Selected from 1, 2 or 3; the m is 6 Selected from 1 or 2; the m is 7 Selected from 1, 2, 3, 4 or 5; the m is 8 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m is 9 Selected from 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present 6 When two or more R' s 6 Are identical or different from each other, or adjacent R 6 Are linked to each other to form a substituted or unsubstituted ring.
Preferably, when Si (R 4 ) 3 Substituted for L 0 、L 1 、L 2 When in the above, it replaces R of corresponding quantity 6 。
Preferably, R 6 One, two, three, four or more of them are selected from Si (R 4 ) 3 。
More preferably, R 6 One or both of them are selected from Si (R 4 ) 3 。
Preferably, said R 3 Selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of, or adjacent R 3 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other;
the R is 3 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, the dicarbazole compound contains one, two, three, four or more Si (R 4 ) 3 。
Preferably, the dicarbazole compound contains one, two, three or four Si (R 4 ) 3 。
Preferably, the dicarbazole compound is selected from any one of the structures shown in the following,
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the invention also provides a preparation method of the dicarbazole compound, but the preparation method of the dicarbazole compound is not limited to the method. The core structure of formula 1 can be prepared by the reaction scheme shown below:
preparation of chemical formula 1-1:
preparation of chemical formula 1-2:
the Xa is the same or different and is selected from any one of I, br and Cl;
the present invention may bond the above substituents by a method known in the art, and the kind and position of substituents or the number of substituents may be changed according to a technique known in the art.
The invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic layers arranged between or outside the anode and the cathode, wherein the organic layers comprise one or a combination of at least two of the dicarbazole compounds.
Preferably, the organic layer according to the present invention comprises a cover layer comprising one or a combination of at least two of the dicarbazole compounds according to the present invention.
The organic layer of the present invention may further include a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, an encapsulation layer, etc. However, the structure of the organic electroluminescent device of the present invention is not limited to the above-described structure, and if necessary, a plurality of organic layers may be omitted or simultaneously provided, and an organic layer having the same function may be formed in a laminated structure of two or more layers.
The organic electroluminescent device of the invention has the structure that:
substrate/anode/hole transport layer/light emitting layer/electron transport layer/cathode/cover layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode/capping layer;
A substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
a substrate/anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting auxiliary layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;
however, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the device parameter requirement and the material characteristics, partial organic layers can be added or omitted, and the organic layers with the same function can be made into a laminated structure with more than two layers.
The organic electroluminescent device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed.
In the organic electroluminescent device according to the present invention, the anode material preferably uses a high work function material capable of promoting injection of holes into the organic layer. Specific examples of the anode material that can be used in the present invention may include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO); combinations of metals and oxides, such as ITO-Ag-ITO; conductive polymers such as poly (3-methylthiophene), polypyrrole, polyaniline, poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), and the like, but are not limited thereto.
In the organic electroluminescent device of the present invention, the hole injection material is preferably a material having a good hole accepting ability. Specific examples of the hole injecting material that can be used in the present invention may include: silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, other metal oxides, phthalocyanine compounds, biphenylamine compounds, phenazine compounds, other materials, such as copper phthalocyanine (CuPc), titanyl phthalocyanine, N ' -diphenyl-N, N ' -di- [4- (N, N-diphenylamine) phenyl ] benzidine (NPNPB), N ' -tetra (4-methoxyphenyl) benzidine (MeO-TPD), and bisquinoxalino [2,3-a:2',3' -c ] phenazine (HATNA), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like, but are not limited thereto.
In the organic electroluminescent device according to the present invention, the hole transporting material is preferably a material having excellent hole transporting property and HOMO level matching with the corresponding anode material. Specific examples of the hole transporting material that can be used in the present invention may include materials such as diphenylamines, triphenylamines, fluorenes, and carbazoles, such as N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -di (naphthalen-1-yl) -N, N ' -di (phenyl) -2,2' -dimethylbenzidine (α -NPD), N ' -diphenyl-N, N ' -di (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), 4- [1- [4- [ di (4-methylphenyl) amino ] phenyl ] cyclohexyl ] -N- (3-methylphenyl) -N- (4-methylphenyl) aniline (TAPC), and the like, but are not limited thereto.
In the organic electroluminescent device, the luminescent auxiliary layer is preferably a material with good hole transmission performance and electron blocking performance. Specific examples of the light-emitting auxiliary material that can be used in the present invention may include triarylamine derivatives, spirofluorene derivatives, furan derivatives, and the like, such as TPD, NPB, N, N4-bis ([ 1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1,1':4',1 "-terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4 '-diamine, N- ([ 1,1' -diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9 '-spirobifluorene-2-amine, N-bis ([ 1,1' -biphenyl ] -4-yl) -3'- (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, and the like, but is not limited thereto.
In the organic electroluminescent device of the present invention, the luminescent layer material comprises a luminescent layer host material and a luminescent layer doping material, and the luminescent layer host material may be selected from 4,4 '-bis (9-Carbazolyl) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -ADN), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4', 1':4', 1' -tetrabiphenyl]-4, 4' -diamine (4 PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), etc., but is not limited thereto. Preferably, the host material of the light emitting layer of the present invention is selected from 9, 10-bis (2-naphthyl) Anthracene (ADN), 9'- (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), AND the like. The light-emitting layer doping material can be selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4' -di [4- (diphenylamino) styryl)]Biphenyl (BDAVBi), 4' -di [4- (di-p-tolylamino) styryl]Diphenyl (DPAVBi), bis (2-hydroxyphenylpyridine) beryllium (Bepp 2), bis (4, 6-difluorophenylpyridine-C2, N) iridium picolinate (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminomethyl) aminePhenylstyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq) 3 ) Ir (piq) iridium bis (1-phenylisoquinoline) (acetylacetonate) 2 (acac)) and the like, but is not limited thereto. Preferably, the light-emitting layer guest according to the present invention is selected from the group consisting of 4,4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 9, 10-di [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like.
The doping ratio of the host material for the light-emitting layer and the doping material for the light-emitting layer may be varied depending on the materials used, and is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.
In the organic electroluminescent device according to the present invention, the hole blocking material has a strong hole blocking ability and suitable HOMO and LUMO energy levels, and specific examples of the hole blocking material that can be used in the present invention may include imidazoles, triazoles, phenanthroline derivatives, etc., such as 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-t-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), etc., but are not limited thereto.
In the organic electroluminescent device according to the present invention, the electron transport material is preferably a material having a strong electron withdrawing ability and low HOMO and LUMO energy levels, and specific examples of the electron transport material usable in the present invention may include imidazoles, triazoles, phenanthroline derivatives, quinolines, and the like, such as 2,9- (dimethyl) -4, 7-biphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris [ (3-pyridyl) -phenyl ] benzene (TmPyPB), 4' -bis (4, 6-diphenyl-1, 3, 5-triazinyl) biphenyl (BTB), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 2- (naphthalene-2-yl) -4,7- (diphenyl) -1, 10-phenanthrene (hnb), 8-hydroxy-Lithium (LiQ), and the like, but not limited thereto.
In the organic electroluminescent device of the present invention, the electron injection material is preferably selected from the group consisting ofThe adjacent organic transport material, host material, or the like has a smaller potential barrier difference material, and has an effect of injecting electrons from the cathode. Examples of electron injection materials that can be used in the present invention include: alkali metal salts (e.g., liF, csF), alkaline earth metal salts (e.g., mgF) 2 ) Metal oxides (such as Al 2 O 3 、MoO 3 ) But is not limited thereto.
In the organic electroluminescent device according to the present invention, the cathode material preferably uses a low work function material capable of promoting electron injection into the organic layer. Specific examples of the cathode material that can be used in the present invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metallic materials, e.g. LiF/Al, mg/Ag, li/Al, liO 2 /Al、BaF 2 Al, etc., but is not limited thereto.
In the organic electroluminescent device according to the present invention, the material for the cover layer is preferably a material for improving optical coupling. Specific examples of the material for the capping layer that can be used in the present invention may include arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, the biscarbazole compounds according to the present invention, and the like, and preferably the biscarbazole compounds according to the present invention, the capping layer may be formed on the outside of the anode and the outside of the cathode at the same time, or may be disposed on the outside of the anode or the outside of the cathode, and preferably the capping layer according to the present invention is disposed on the outside of the cathode.
The thickness of each organic layer of the organic electroluminescent device is not particularly limited, and may be any thickness commonly used in the art.
The organic electroluminescent device of the present invention may be any one of a vacuum evaporation method, a spin coating method, a vapor deposition method, a blade coating method, a laser thermal transfer method, an electrospray coating method, a slit coating method, and a dip coating method, and in the present invention, a vacuum evaporation method is preferably used.
The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, indication boards, signal lamps and the like.
The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.
Preparation and characterization of the Compounds
Description of the starting materials, reagents and characterization equipment:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;
synthesis example 1: preparation of intermediate A-54
Preparation of intermediate c-54:
under nitrogen, intermediate a-54 (29.12 g,100 mmol), toluene (500 mL), b-54 (22.18 g,110 mmol), pd 2 (dba) 3 (0.92 g,1.00 mmol), BINAP (1.89 g,3.00 mmol) and sodium tert-butoxide (19.22 g,200 mmol) were added to a reaction flask, stirred and dissolved, the reaction was refluxed for 7.5 hours, after the reaction was completed, the mixture was cooled to room temperature, filtered, the organic solvent was removed from the filtrate by distillation under reduced pressure, and the obtained solid was recrystallized from methanol to give intermediate c-54 (32.13 g, yield 78%), and HPLC purity was not less than 99.81%. Mass spectrum m/z:411.0564 (theory: 411.0597).
Preparation of intermediate A-54:
under nitrogen, c-54 (30.89 g,75.00 mmol), pinacol biborate (19.05 g,75.00 mmol), potassium acetate(16.19g，165.00mmol)，PdCl 2 (dppf) (0.54 g,0.75 mmol) and 1, 4-dioxane (250 mL) were added to the reaction flask, and the mixture was stirred and heated to reflux for 6 hours. After the reaction is completed and cooled to room temperature, filtering to obtain a filter cake, flushing the filter cake with ethanol, and finally recrystallizing the filter cake with toluene to obtain an intermediate A-54 (31.34 g, 83%); HPLC purity is more than or equal to 99.85%. Mass spectrum m/z:503.1833 (theory: 503.1839).
The following intermediates were prepared by the preparation method of synthetic example 1 by replacing the raw materials correspondingly, and the specific conditions of the raw materials and intermediates are shown in the following table:
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synthesis example 2: preparation of intermediate B-2
Preparation of intermediate g-2
700mL of dehydrated tetrahydrofuran and 46.62g (200.00 mmol) of raw material d-2 were charged into a reaction flask under an argon atmosphere. The mixture was cooled to-78 ℃ and a 2.5M n-hexane solution (100 ml,250 mmol) of n-butyllithium was slowly added dropwise to the mixture, and the mixture was stirred for 2.5 hours. To the mixture was added a solution of 66.67g (200.00 mol) of raw material e-2 dissolved in 650mL of tetrahydrofuran, and the mixture was stirred for 5.5 hours. After that, the temperature of the mixture was set to room temperature, and the mixture was stirred overnight. Thereafter, 300mL of 1M hydrochloric acid was added to the mixture, extracted with ethyl acetate, and the organic phase was collected and dried over anhydrous MgSO 4 Drying, filtering, and concentrating the filtrate under reduced pressure to remove the solvent to obtain oily substance. The resulting oil, 250mL glacial acetic acid, and 4mL concentrated hydrochloric acid were added to the reaction flask. The reaction was heated at reflux for 6 hours. After the reaction was completed, distilled water was added to the mixture, followed by extraction with ethyl acetate,the organic phase was collected, washed with saturated aqueous sodium bicarbonate and saturated brine, and then with anhydrous MgSO 4 Drying, filtering, concentrating the filtrate under reduced pressure to obtain oily substance, purifying by column chromatography (n-hexane: toluene=10:2 as eluent), and finally obtaining intermediate g-2 (72.30 g, yield 77%) with HPLC purity not less than 99.21%. Mass spectrum m/z:469.0976 (theory: 468.0909).
Preparation of intermediate h-2:
to a reaction flask was added 500mL of dehydrated tetrahydrofuran as intermediate g-2 (70.42 g,150.00 mmol) under an argon atmosphere, then the reaction solution was cooled to-78℃and 75mL (120 mmol) of a 1.6M n-hexane solution of n-butyllithium was slowly added dropwise, and after stirring at-78℃for 4 hours, 75mL of a dehydrated tetrahydrofuran solution of trimethyl borate (39.49 g,380.00 mmol) was added dropwise, and after stirring for 2.5 hours, the mixture was slowly warmed to room temperature. 400mL of 3M hydrochloric acid was added, stirred for 4 hours, distilled water was added, followed by extraction with methylene chloride, and the organic phase was collected and dried over anhydrous MgSO 4 Drying, distilling under reduced pressure to remove the solvent, and recrystallizing with dichloromethane to obtain intermediate h-2 (48.22 g, yield 74%) with HPLC purity of 99.61%. Mass spectrum m/z:434.1810 (theory: 434.1873).
Preparation of intermediate j-2:
intermediate h-2 (43.44 g,100.00 mmol), starting material i-2 (29.79 g,100.00 mmol), and dried Cu (OAc) 2 ·H 2 O (1.82 g,10.00 mmol), n-decanoic acid (3.45 g,20.00 mmol) was added to CaCl 2 In a protected reaction flask, DBU (18.27 g,120.00 mmol) and anhydrous toluene (350 mL) were then added sequentially to the reaction mixture and stirred at room temperature for 26 hours. After the completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined ethyl acetate portions were washed with brine solution, with anhydrous Na 2 SO 4 The filtrate was dried, filtered and concentrated under reduced pressure, and the crude product was purified by column chromatography (n-hexane: ethyl acetate=95:5 as eluent) to give intermediate j-2 (48.74 g, 71% yield) with HPLC purity > 99.37%. Mass spectrum m/z:685.0244 (theory: 685.0297).
Preparation of intermediate B-2:
intermediate j-2 (48.06 g,70.00 mmol), anhydrous toluene (350 mL) and Pd (OAc) 2 (0.79 g,3.5 mmol) and DBU (60.90 g,400.00 mmol) were added successively to a reaction flask, and the reaction mixture was degassed with argon and heated at 100℃for 10 hours. After the reaction was completed, it was cooled to room temperature, and the reaction mixture was diluted with water and extracted with ethyl acetate. The combined ethyl acetate portions were washed with brine solution, with anhydrous Na 2 SO 4 The filtrate was dried, filtered and concentrated under reduced pressure, and the crude product was purified by column chromatography (n-hexane: ethyl acetate=80:20 as eluent) to give intermediate B-2 (29.33 g, 75% yield) with HPLC purity ≡ 99.72%. Mass spectrum m/z:557.1121 (theory: 557.1174).
The following intermediates were prepared by the preparation method of synthetic example 2 by replacing the raw materials correspondingly, and the specific conditions of the raw materials and intermediates are shown in the following table:
synthesis example 3: preparation of intermediate C-2
A-2 (22.32 g,52 mmol), intermediate B-2 (27.93 g,50 mmol) and Pd (PPh) were added sequentially to a reaction flask under argon 3 ) 4 (0.58 g,0.50 mmol), potassium acetate (10.80 g,110 mmol), toluene (300 mL), ethanol (100 mL), and water (100 mL), and the mixture was stirred and the above-mentioned system was refluxed for 5 hours; after the reaction was completed, cooled to room temperature, suction filtered to obtain a filter cake, and the filter cake was rinsed with ethanol, and finally the filter cake was purified with toluene/ethanol=10: 1 to obtain intermediate C-2 (31.52 g, yield 79%) with HPLC purity not less than 99.65%. Mass spectrum m/z:797.3227 (theory: 797.3226).
The following intermediates can be prepared by correspondingly replacing raw materials or intermediates according to the preparation method of the synthesis example 3, and the specific conditions of the raw materials and the intermediates are shown in the following table:
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synthesis example 4: preparation of Compound 2
Intermediate C-2 (19.95 g,25.00 mmol), toluene (175 mL), D-2 (6.83 g,25.00 mmol), pd under nitrogen 2 (dba) 3 (0.27 g,0.30 mmol), BINAP (0.37 g,0.60 mmol) and sodium tert-butoxide (7.21 g,75.00 mmol) were added to a reaction flask, stirred and dissolved, the reaction was refluxed for 7.5 hours, after the reaction was completed, the mixture was cooled to room temperature, filtered, the organic solvent was removed from the filtrate by distillation under reduced pressure, and the obtained solid material was recrystallized from methanol to give compound 2 (16.84 g) with an HPLC purity of not less than 99.94%. Mass spectrum m/z:989.4152 (theory: 989.4165). Theoretical element content (%) C 72 H 55 N 3 Si: c,87.32; h,5.60; n,4.24. Measured element content (%): c,87.35; h,5.62; n,4.23.
Synthesis example 5: preparation of Compound 8
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-8, D-8, respectively, to give Compound 8 (16.39 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:922.3759 (theory: 922.3743). Theoretical element content (%) C 68 H 50 N 2 Si: c,88.46; h,5.46; n,3.03. Measured element content (%): c,88.48; h,5.43; n,3.02.
Synthesis example 6: preparation of Compound 28
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-8, D-28, respectively, to give Compound 28 (16.77 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:1000.3988 (theory: 1000.3961). Theoretical element content (%) C 72 H 52 N 4 Si: c,86.37; h,5.23; n,5.60. Measured element content (%): c,86.38; h,5.26; n,5.62.
Synthesis example 7: preparation of Compound 54
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-54, D-54, respectively, to give Compound 54 (17.67 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:1086.3232 (theory: 1086.3246). Theoretical element content (%) C 74 H 50 N 4 S 2 Si: c,81.73; h,4.63; n,5.15. Measured element content (%): c,81.77; h,4.61; n,5.16.
Synthesis example 8: preparation of Compound 130
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-130, D-130, respectively, to give Compound 130 (15.94 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:872.3576 (theory: 872.3587). Theoretical element content (%) C 64 H 48 N 2 Si: c,88.03; h,5.54; n,3.21. Measured element content (%): c,88.05; h,5.53; n,3.24.
Synthesis example 9: preparation of Compound 133
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-133, D-133, respectively, to give Compound 133 (15.14 g); HPLC purity is more than or equal to 99.99%. Mass spectrum m/z:806.3528 (theory: 806.3513). Theoretical element content (%) C 56 H 50 N 2 Si 2 : c,83.33; h,6.24; n,3.47. Measured element content (%): c,83.31; h,6.25; n,3.46.
Synthesis example 10: preparation of Compound 143
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-143, D-133, respectively, to give Compound 143 (15.75 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:874.2819 (theory: 874.2803). Theoretical element content (%) C 57 H 39 F 5 N 2 Si: c,78.24; h,4.49; n,3.20. Measured element content (%): c,78.26; h,4.45; n,3.21.
Synthesis example 11: preparation of Compound 158
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-133, D-158, respectively, to give Compound 158 (15.86 g); HPLC purity is more than or equal to 99.98%. Mass spectrum m/z:868.4222 (theory: 868.4213). Theoretical element content (%) C 63 H 56 N 2 Si: c,87.05; h,6.49; n,3.22. Measured element content (%): c,87.08; h,6.45; n,3.25.
Synthesis example 12: preparation of Compound 161
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-161, D-133, respectively, to give Compound 161 (15.21 g); HPLC purity is more than or equal to 99.99%. Mass spectrum m/z:810.3447 (theory: 810.3430). Theoretical element content (%) C 59 H 46 N 2 Si: c,87.37; h,5.72; n,3.45. Measured element content (%): c,87.38; h,5.75; n,3.43.
Synthesis example 13: preparation of Compound 181
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-133, D-181, respectively, to give compound 181 (15.17 g); HPLC purity is more than or equal to 99.98%. Mass spectrum m/z:819.3983 (theory: 819.3995). Theoretical element content (%) C 59 H 37 D 9 N 2 Si: c,86.40; h,6.76; n,3.42. Measured element content (%): c,86.42; h,6.73; n,3.41.
Synthesis example 14: preparation of Compound 201
According to the preparation method of synthetic example 4, equimolar amounts of C-2 and D-2 are replaced respectivelyEquimolar changes were made to C-201 and D-201 to give compound 201 (15.21 g); HPLC purity is more than or equal to 99.99%. Mass spectrum m/z:810.3443 (theory: 810.3430). Theoretical element content (%) C 59 H 46 N 2 Si: c,87.37; h,5.72; n,3.45. Measured element content (%): c,87.38; h,5.75; n,3.47.
Synthesis example 15: preparation of Compound 253
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-133, D-253, respectively, to give Compound 253 (16.04 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:878.3321 (theory: 878.3304). Theoretical element content (%) C 60 H 45 F 3 N 2 Si: c,81.98; h,5.16; n,3.19. Measured element content (%): c,81.96; h,5.19; n,3.15.
Synthesis example 16: preparation of Compound 257
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-161, D-257, respectively, to give compound 257 (15.97 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:886.3761 (theory: 886.3743). Theoretical element content (%) C 65 H 50 N 2 Si: c,88.00; h,5.68; n,3.16. Measured element content (%): c,88.05; h,5.64; n,3.18.
Synthesis example 17: preparation of Compound 296
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-161 and D-296, respectively, to give compound 296 (16.95 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:996.3916 (theory: 996.3900). Theoretical element content (%) C 74 H 52 N 2 Si: c,89.12; h,5.26; n,2.81. Measured element content (%): c,89.13; h,5.28; n,2.82.
Synthesis example 18: preparation of Compound 305
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-305, D-133, respectively, to give Compound 305 (17.14 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:992.3996 (theory: 992.3982). Theoretical element content (%) C 71 H 56 N 2 Si 2 : c,85.84; h,5.68; n,2.82. Measured element content (%): c,85.86; h,5.65; n,2.84.
Synthesis example 19: preparation of Compound 315
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-315 and D-315, respectively, to give Compound 315 (15.24 g); HPLC purity is more than or equal to 99.99%. Mass spectrum m/z:801.3571 (theory: 801.3588). Theoretical element content (%) C 58 H 39 D 5 N 2 Si: c,86.85; h,6.16; n,3.49. Measured element content (%): c,86.86; h,6.19; n,3.47.
Synthesis example 20: preparation of Compound 347
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-347, D-133, respectively, to give Compound 347 (15.86 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:880.4078 (theory: 880.4089). Theoretical element content (%) C 64 H 40 D 8 N 2 Si: c,87.23; h,6.40; n,3.18. Measured element content (%): c,87.25; h,6.41; n,3.16.
Synthesis example 21: preparation of Compound 361
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-315 and D-130, respectively, to give compound 361 (15.94 g); HPLC purity is more than or equal to 99.98%. Mass spectrum m/z:872.3572 (theory: 872.3587). Theoretical element content (%) C 64 H 48 N 2 Si: c,88.03; h,5.54; n,3.21. Measured element content (%): c,88.07; h,5.53; n,3.22.
Synthesis example 22: preparation of Compound 375
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-375, D-130, respectively, to give Compound 375 (16.75 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:984.4825 (theory: 984.4839). Theoretical element content (%) C 72 H 64 N 2 Si: c,87.76; h,6.55; n,2.84. Measured element content (%): c,87.78; h,6.58; n,2.83.
Synthesis example 23: preparation of Compound 390
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-390, D-390, respectively, to give Compound 390 (16.93 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:980.4938 (theory: 980.4921). Theoretical element content (%) C 69 H 68 N 2 Si 2 : c,84.44; h,6.98; n,2.85. Measured element content (%): c,84.46; h,6.95; n,2.83.
Synthesis example 24: preparation of Compound 437
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-437 and D-257, respectively, to give Compound 437 (16.85 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:948.3913 (theory: 948.3900). Theoretical element content (%) C 70 H 52 N 2 Si: c,88.57; h,5.52; n,2.95. Measured element content (%): c,88.55; h,5.56; n,2.96.
Synthesis example 25: preparation of Compound 454
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-454, D-454, respectively, to give Compound 454 (16.70 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:953.4228 (theory: 953.4214). Theoretical element content (%) C 70 H 47 D 5 N 2 Si: c,88.10; h,6.02; n,2.94. Measured element content (%): c,88.11; h,6.06; n,2.92.
Synthesis example 26: preparation of Compound 495
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-495, D-495, respectively, to give Compound 495 (16.74 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:1013.3815 (theory: 1013.3801). Theoretical element content (%) C 73 H 51 N 3 OSi: c,86.44; h,5.07; n,4.14. Measured element content (%): c,86.46; h,5.04; n,4.11.
Synthesis example 27: preparation of Compound 496
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-496 and D-133, respectively, to give compound 496 (15.25 g); HPLC purity is more than or equal to 99.99%. Mass spectrum m/z:812.3348 (theory: 812.3335). Theoretical element content (%) C 57 H 44 N 4 Si: c,84.20; h,5.45; n,6.89. Measured element content (%): c,84.23; h,5.44; n,6.84.
Synthesis example 28: preparation of Compound 499
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-499 and D-133, respectively, to give Compound 499 (15.70 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:871.4072 (theory: 871.4088). Theoretical element content (%) C 61 H 41 D 7 N 4 Si: c,84.00; h,6.35; n,6.42. Measured element content (%): c,84.02; h,6.31; n,6.46.
Synthesis example 29: preparation of Compound 521
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-521, D-257, respectively, to give Compound 521 (15.72 g); HPLC purity is more than or equal to 99.98%. Mass spectrum m/z:860.3573 (theory: 860.3587). Theoretical element content (%) C 63 H 48 N 2 Si: c,87.87; h,5.62; n,3.25. Measured element content (%): c,87.88; h,5.66; n,3.23.
Synthesis example 30: preparation of Compound 526
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-526, D-526, respectively, to give compound 526 (17.05 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:1032.4789 (theory: 1032.4777). Theoretical element content (%) C 76 H 56 D 4 N 2 Si: c,88.33; h,6.24; n,2.71. Measured element content (%): c,88.35; h,6.21; n,2.74.
Synthesis example 31: preparation of Compound 527
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-527 and D-257, respectively, to give compound 527 (16.55 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:972.3912 (theory: 972.3900). Theoretical element content (%) C 72 H 52 N 2 Si: c,88.85; h,5.39; n,2.88. Measured element content (%): c,88.86; h,5.34; n,2.86.
Synthesis example 32: preparation of Compound 534
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-534, D-133, respectively, to give compound 534 (16.67 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:965.3931 (theory: 965.3914). Theoretical element content (%) C 68 H 51 N 5 Si: c,84.53; h,5.32; n,7.25. Measured element content (%): c,84.54; h,5.35; n,7.22.
Synthesis example 33: preparation of Compound 550
According to the synthesisThe preparation of example 4 replaced equimolar C-2, D-2 with equimolar C-550, D-257, respectively, yielding compound 550 (16.46 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:926.4042 (theory: 926.4056). Theoretical element content (%) C 68 H 54 N 2 Si: c,88.08; h,5.87; n,3.02. Measured element content (%): c,88.06; h,5.88; n,3.05.
Synthesis example 34: preparation of Compound 564
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-564, D-257, respectively, to give compound 564 (16.83 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:989.3819 (theory: 989.3801). Theoretical element content (%) C 71 H 51 N 3 OSi: c,86.11; h,5.19; n,4.24. Measured element content (%): c,86.15; h,5.18; n,4.26.
Synthesis example 35: preparation of Compound 574
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-574 and D-133, respectively, to give Compound 574 (16.69 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:926.3823 (theory: 926.3805). Theoretical element content (%) C 66 H 50 N 4 Si: c,85.49; h,5.44; n,6.04. Measured element content (%): c,85.48; h,5.47; n,6.05.
Synthesis example 36: preparation of Compound 600
According to the preparation method of Synthesis example 4, equimolar C-2 and D-2 were replaced with equimolar C-201 and D-600, respectively, to give Compound 600 (16)58 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:960.3916 (theory: 960.3900). Theoretical element content (%) C 71 H 52 N 2 Si: c,88.71; h,5.45; n,2.91. Measured element content (%): c,88.73; h,5.46; n,2.92.
Synthesis example 37: preparation of Compound 607
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-315, D-607, respectively, to give Compound 607 (16.38 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:962.3673 (theory: 962.3692). Theoretical element content (%) C 70 H 50 N 2 OSi: c,87.28; h,5.23; n,2.91. Measured element content (%): c,87.26; h,5.24; n,2.93.
Synthesis example 38: preparation of Compound 616
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-616, D-616, respectively, to give Compound 616 (16.28 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:916.3323 (theory: 916.3307). Theoretical element content (%) C 65 H 48 N 2 SSi: c,85.11; h,5.27; n,3.05. Measured element content (%): c,85.12; h,5.24; n,3.03.
Synthesis example 39: preparation of Compound 628
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-628, D-628, respectively, to give Compound 628 (16.68 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:980.4421 (theory: 980.4402). Theoretical element content (%) C 72 H 44 D 8 N 2 Si: c,88.12; h,6.16; n,2.85. Measured element content (%): c,88.15; h,6.14; n,2.88.
Synthesis example 40: preparation of Compound 632
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-454, D-632, respectively, to give Compound 632 (16.74 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:969.4126 (theory: 969.4114). Theoretical element content (%) C 69 H 55 N 3 OSi: c,85.41; h,5.71; n,4.33. Measured element content (%): c,85.42; h,5.73; n,4.36.
Synthesis example 41: preparation of Compound 648
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-454 and D-648, respectively, to give Compound 648 (16.84 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:1004.3634 (theory: 1004.3620). Theoretical element content (%) C 72 H 52 N 2 SSi: c,86.02; h,5.21; n,2.79. Measured element content (%): c,86.03; h,5.24; n,2.78.
Synthesis example 42: preparation of Compound 660
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-660, D-130, respectively, to give compound 660 (16.85 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:948.3916 (theory: 948.3900). Theoretical element content (%) C 70 H 52 N 2 Si: c,88.57; h,5.52; n,2.95. Measured element content (%): c,88.58；H,5.54；N,2.97。
Synthesis example 43: preparation of Compound 675
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-675, D-675, respectively, to give Compound 675 (16.63 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:977.3421 (theory: 977.3438). Theoretical element content (%) C 69 H 47 N 3 O 2 Si: c,84.72; h,4.84; n,4.30. Measured element content (%): c,84.71; h,4.85; n,4.33.
Synthesis example 44: preparation of Compound 704
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-704, D-704, respectively, to give Compound 704 (16.85 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:1020.3329 (theory: 1020.3318). Theoretical element content (%) C 70 H 48 N 4 OSSi: c,82.32; h,4.74; n,5.49. Measured element content (%): c,82.36; h,4.73; n,5.48.
Synthesis example 45: preparation of Compound 727
According to the production method of Synthesis example 4, equimolar amounts of C-2 and D-2 were replaced with equimolar amounts of C-727 and D-727, respectively, to give Compound 727 (16.22 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:939.3662 (theory: 939.3645). Theoretical element content (%) C 67 H 49 N 3 OSi: c,85.59; h,5.25; n,4.47. Measured element content (%): c,85.54; h,5.27; n,4.46.
Synthesis example 46: preparation of Compound 732
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-732, D-130, respectively, to give Compound 732 (16.82 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:1018.4664 (theory: 1018.4682). Theoretical element content (%) C 75 H 62 N 2 Si: c,88.37; h,6.13; n,2.75. Measured element content (%): c,88.33; h,6.16; n,2.74.
Synthesis example 47: preparation of Compound 735
According to the production method of Synthesis example 4, equimolar C-2 and D-2 were replaced with equimolar C-735 and D-735, respectively, to give Compound 735 (17.52 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:1077.4102 (theory: 1077.4114). Theoretical element content (%) C 78 H 55 N 3 OSi: c,86.87; h,5.14; n,3.90. Measured element content (%): c,86.88; h,5.11; n,3.93.
Synthesis example 48: preparation of Compound 762
According to the production method of Synthesis example 4, equimolar C-2, D-2 were replaced with equimolar C-762, D-133, respectively, to give Compound 762 (17.06 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:1017.4461 (theory: 1017.4478). Theoretical element content (%) C 74 H 59 N 3 Si: c,87.28; h,5.84; n,4.13. Measured element content (%): c,87.25; h,5.86; n,4.15.
Device examples 1 to 45
Device example 1: the ITO glass substrate is ultrasonically cleaned by 5% glass cleaning liquid for 2 times each for 20 minutes, and then ultrasonically cleaned by deionized water for 2 times each for 10 minutes. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. Vacuum evaporation HI on ITO substrate: HT-1=97:3 (mass ratio) as hole injection layer evaporation thickness 15nm; vacuum evaporating HT-2 on the hole injection layer as a hole transport layer, wherein the evaporating thickness is 80nm; vacuum evaporation of inventive compound 2 on hole transport layer: RD=95:5 (mass ratio) as a light-emitting layer, and the vapor deposition thickness is 30nm; vacuum evaporating ET on the luminous layer as an electron transport layer, wherein the evaporating thickness is 35nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1nm; al is vacuum evaporated on the electron injection layer as a cathode, and the evaporation thickness is 80nm.
Device examples 2 to 45: an organic electroluminescent device was produced by the same procedure as in device example 1, except that the compound 2 of the present invention in device example 1 was replaced as the host material with the compounds 8, 28, 54, 130, 133, 143, 158, 161, 181, 201, 253, 257, 296, 305, 315, 347, 361, 375, 390, 437, 454, 495, 496, 499, 521, 526, 527, 534, 550, 564, 574, 600, 607, 616, 628, 632, 648, 660, 675, 704, 727, 732, 735, 762, respectively.
Comparative examples 1, 2: an organic electroluminescent device was produced by the same procedure as in device example 1, except that the compound 2 of the present invention in device example 1 was replaced with the comparative compound 1 and the comparative compound 2 as the host material.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.
The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 1. Table 1 shows the results of the test of the luminescence characteristics of the organic electroluminescent devices prepared from the compounds according to the examples of the present invention and the comparative materials.
Table 1 test of light emitting characteristics of organic electroluminescent device
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As can be seen from the results in table 1, the device examples 1 to 45 prepared using the dicarbazole compound of the present invention have higher luminous efficiency and longer device lifetime than the comparative examples 1 and 2.
Device examples 46 to 90
Device example 46: the ITO glass substrate is ultrasonically cleaned by 5% glass cleaning liquid for 2 times each for 20 minutes, and then ultrasonically cleaned by deionized water for 2 times each for 10 minutes. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. Vacuum evaporation HI on ITO substrate: HT-1=98:2 (mass ratio) as hole injection layer evaporation thickness 15nm; vacuum evaporating HT-2 on the hole injection layer as a hole transport layer, wherein the evaporating thickness is 70nm; vacuum evaporation of inventive compound 2 on hole transport layer: gd=97:3 (mass ratio) as light-emitting layer, vapor deposition thickness 40nm; vacuum evaporating ET on the luminous layer as an electron transport layer, wherein the evaporating thickness is 30nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1nm; al is vacuum evaporated on the electron injection layer as a cathode, and the evaporation thickness is 80nm.
Device examples 47 to 90: an organic electroluminescent device was produced by the same procedure as in device example 46, except that the compound 2 of the present invention in device example 46 was replaced as the host material with the compounds 8, 28, 54, 130, 133, 143, 158, 161, 181, 201, 253, 257, 296, 305, 315, 347, 361, 375, 390, 437, 454, 495, 496, 499, 521, 526, 527, 534, 550, 564, 574, 600, 607, 616, 628, 632, 648, 660, 675, 704, 727, 732, 735, 762, respectively.
Comparative examples 3, 4: an organic electroluminescent device was produced by the same procedure as in device example 46, except that the compound 2 of the present invention in device example 46 was replaced with the comparative compound 1 and the comparative compound 2 as the host materials.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.
The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 2. Table 2 shows the results of the luminescence characteristics of the organic electroluminescent devices prepared from the compounds according to the examples of the present invention and the comparative materials.
Table 2 test of light emission characteristics of organic electroluminescent devices
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As can be seen from the results in table 2, device examples 46 to 90 prepared using the dicarbazole-based compound of the present invention have higher luminous efficiency and longer device lifetime than comparative examples 3 and 4.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.
Claims (10)
1. A dicarbazole compound is characterized in that the dicarbazole compound has a structure shown in a chemical formula 1,
the x are the same or different and are selected from CR 3 Or N, wherein is the same as the Ar 0 、L 0 The bonded x is selected from C;
the R is 3 Any one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl, or adjacent R 3 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other;
the Ar is as follows 0 Selected from the group consisting of the structures shown in chemical formula 2,
the z are the same or different and are selected from CR 2 Or N;
the R is 1 、R 2 The same or different is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl, or adjacent R 2 Are connected with each other to form a substituted or unsubstituted ring;
The L is 0 、L 1 、L 2 The same or different arylene groups are selected from any one of single bonds, substituted or unsubstituted C6-C24 arylene groups, substituted or unsubstituted C2-C25 heteroarylene groups and substituted or unsubstituted C3-C12 alicyclic groups;
the Ar is as follows 1 、Ar 2 The same or different aryl groups are selected from any one of substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C24 aryl groups, substituted or unsubstituted C2-C25 heteroaryl groups and substituted or unsubstituted silyl groups;
at least one group of the chemical formula 1 is bonded to Si (R 4 ) 3 Substitution, said R 4 The same or different one is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C12 heteroaryl.
2. A dicarbazole compound according to claim 1, wherein Ar 0 Selected from any one of the structures shown below,
the a 1 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the a 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the a 3 Selected from 0, 1, 2, 3, 4, 5 or 6; the a 4 Selected from 0, 1, 2, 3, 4 or 5; the a 5 Selected from 0, 1, 2, 3 or 4; when two or more R's are present 2 When two or more R' s 2 Are the same as or different from each other;
the R is 2 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, goldRigid alkyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 2 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other;
the R is 1 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 1 May be substituted with one or more substituents R 11 Substituted, the substituent R 11 Selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, trimethylsilyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other.
3. A dicarbazole compound according to claim 1, wherein Ar 1 、Ar 2 The same or different are selected from Si (R) 4 ) 3 Or any one of the structures shown below,
the v is the same or different and is selected from CH or N;
said Y is selected from O, S, C (Ra) 2 Any one of N (Rb);
the Ra is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Ra can be directly connected with L 1 And/or L 2 Connecting;
the Rb is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Rb can be directly combined with L 1 And/or L 2 Connecting;
the R is 5 The same or different one is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl;
said n 1 Selected from 1, 2, 3, 4 or 5; said n 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said n 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said n 5 Selected from 1, 2, 3, 4, 5 or 6; when two or more R's are present 5 When two or more R' s 5 Are identical or different from each other, or adjacent R 5 Are linked to each other to form a substituted or unsubstituted ring.
4. A dicarbazole compound according to claim 1, wherein Ar 1 、Ar 2 The same or different are selected from Si (R) 4 ) 3 Or as followsAny one of the structures shown in the figures,
the R is 5 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of them;
the R is 5 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other;
said n 1 Selected from 1, 2, 3, 4 or 5; said n 2 Selected from 1, 2, 3, 4, 5, 6 or 7; said n 3 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said n 5 Selected from 1, 2, 3, 4, 5 or 6; said n 6 Selected from 1, 2, 3 or 4; said n 7 Selected from 1, 2 or 3; said n 8 Selected from 1 or 2; said n 9 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said n 10 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R's are present 5 When two or more R' s 5 Are the same as or different from each other.
5. The dicarbazole compound according to claim 1, wherein theThe L is 0 、L 1 、L 2 The same or different is selected from single bond or any one of the structures shown below,
the u are the same or different and are selected from CH or N;
Said E is selected from O, S, C (Rc) 2 Any one of N (Rd);
the Rc is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Rc can be directly combined with Ar 1 And/or Ar 2 And/or an x-connection;
the Rd is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl, and the Rb can be directly combined with Ar 1 And/or Ar 2 And/or an x-connection;
the R is 6 The same or different one is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl and substituted or unsubstituted silyl;
the m is 1 Selected from 1, 2, 3 or 4; the m is 2 Selected from 1, 2, 3, 4, 5 or 6; the m is 3 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m is 4 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the m is 5 Selected from 1, 2 or 3; the m is 6 Selected from 1 or 2; the m is 7 Selected from 1, 2, 3, 4 or 5; when two or more R's are present 6 When two or more R' s 6 Are mutually connected with each otherIdentical or different, or adjacent R' s 6 Are linked to each other to form a substituted or unsubstituted ring.
6. A dicarbazole compound according to claim 1, wherein R 3 Selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, si (R) 4 ) 3 Any one of, or adjacent R 3 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other;
the R is 3 May be substituted with one or more substituents selected from deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, biphenyl, deuterated phenyl, pentafluorophenyl, naphthyl, si (R) 4 ) 3 Any one or a combination of the above; when two or more substituents are present, the two or more substituents may be the same or different from each other.
7. A dicarbazole compound according to claim 1, wherein L 1 、L 2 、Ar 1 、Ar 2 At least one of the groups is Si (R) 4 ) 3 Substitution;
the R is 4 The same or different groups are selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl and pyrimidinyl;
the R is 4 May be substituted with one or more substituents selected from any one of deuterium, cyano, halogen, trifluoromethyl, methyl, isopropyl, t-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, or a combination thereof;when two or more substituents are present, the two or more substituents may be the same or different from each other.
8. The dicarbazole compound according to claim 1, wherein the dicarbazole compound is selected from any one of the structures shown below,
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9. an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer comprises one or a combination of at least two of the dicarbazole compounds of any of claims 1 to 8.
10. An organic electroluminescent device according to claim 9, wherein the organic layer comprises a light-emitting layer comprising one or a combination of at least two of the biscarbazole compounds according to any of claims 1-8.
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