CN114335367B - Organic electroluminescent device and electronic device - Google Patents
Organic electroluminescent device and electronic device Download PDFInfo
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- CN114335367B CN114335367B CN202111560813.2A CN202111560813A CN114335367B CN 114335367 B CN114335367 B CN 114335367B CN 202111560813 A CN202111560813 A CN 202111560813A CN 114335367 B CN114335367 B CN 114335367B
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- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 239000010410 layer Substances 0.000 claims abstract description 98
- 239000012044 organic layer Substances 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims description 104
- -1 cyano, methyl Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 37
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 239000004305 biphenyl Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000005760 substituted naphthylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 131
- 125000003118 aryl group Chemical group 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 45
- 239000000463 material Substances 0.000 description 42
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 125000000732 arylene group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 125000005549 heteroarylene group Chemical group 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012071 phase 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
- 238000005406 washing Methods 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
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- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
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- 229910052709 silver Inorganic materials 0.000 description 3
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- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- ROJJKFAXAOCLKK-UHFFFAOYSA-N 1-bromo-4-chloro-2-iodobenzene Chemical compound ClC1=CC=C(Br)C(I)=C1 ROJJKFAXAOCLKK-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-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
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- FQKSBRCHLNOAGY-UHFFFAOYSA-N indolo[2,3-a]carbazole Chemical compound C1=CC=C2N=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 FQKSBRCHLNOAGY-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
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- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 238000001771 vacuum deposition Methods 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Abstract
The application provides an organic electroluminescent device and an electronic device,the organic electroluminescent device includes a cathode, an anode, and an organic layer. The organic layer includes an organic light emitting layer including a first compound and a second compound; the first compound is selected from compounds shown in a formula 1; the second compound is selected from compounds represented by formula 2.
Description
Technical Field
The present disclosure relates to the field of organic electroluminescence, and in particular, to an organic electroluminescent device and an electronic device.
Background
In recent years, organic electroluminescent devices (OLEDs) are very popular flat display products at home and abroad because OLED displays have characteristics of self-luminescence, wide viewing angle, short reaction time, high efficiency, wide color gamut, etc.
An organic electroluminescent device (OLED) generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a hole assist layer, an electron blocking layer, a light emitting layer (containing a host and dopant materials), a hole blocking layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light emitting layer from the anode and the cathode, respectively. Then, in the light emitting layer, the injected holes recombine with electrons to form excitons. The excitons are in an excited state to release energy outwards, so that the light-emitting layer emits light outwards.
At present, the organic electroluminescent device still has the problem of poor performance in the use process, such as the problems of too high driving voltage, too low luminous efficiency or short service life, which affect the use field of the organic electroluminescent device, so that further research on the field is still necessary to improve the performance of the organic electroluminescent device.
It should be noted that the information disclosed in the foregoing background section is only for enhancing understanding of the background of the present application and thus may include information that does not form the prior art that is already known to those of ordinary skill in the art.
Disclosure of Invention
The present application provides an organic electroluminescent device and an electronic apparatus for solving the problems of low luminous efficiency and short device lifetime in the prior art.
In order to achieve the purpose of the invention, the application adopts the following technical scheme:
according to a first aspect of the present application, there is provided an organic electroluminescent device comprising a cathode, an anode and an organic layer;
wherein the cathode and the anode are arranged opposite to each other;
the organic layer is located between the cathode and the anode;
the organic layer includes an organic light emitting layer;
the organic light emitting layer includes a first compound and a second compound;
The first compound is selected from compounds shown in formula 1:
therein, L, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
a. b is independently selected from 0, 1, 2, 3, 4 or 5, and a+b is more than or equal to 1;
said L, L 1 、L 2 、Ar 1 、Ar 2 The substituents in (a) are each independently selected from halogen group, cyano group, aryl group with 6-12 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triphenylsilyl group, alkyl group with 1-10 carbon atoms, and carbon atom numberHaloalkyl of 1 to 10, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 2 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a ring;
each R is 1 、R 2 Or R is 3 Each independently selected from hydrogen, deuterium, a halogen group, cyano, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 Represents a substituent R 2 Number n of (n) 2 Selected from 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 1,2,3 or 4, when n 3 When the number is greater than 1, any two R 3 The same or different;
the second compound is selected from compounds represented by formula 2:
wherein R is 4 、R 5 、R 6 、R 7 Independently selected from hydrogen, deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1,2,3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1,2 or 3, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1,2 or 3, when n 6 When the number is greater than 1, any two R 6 The same or different;
n 7 represents a substituent R 7 Number n of (n) 7 Selected from 1,2,3 or 4, when n 7 When the number is greater than 1, any two R 7 The same or different;
L 3 、L 4 the same or different and are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 3 and Ar is a group 4 The same or different and are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
Each L 5 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
each Ar is Ar 5 Each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 3 、L 4 、L 5 、Ar 3 、Ar 4 、Ar 5 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms;
in Ar 3 、Ar 4 And Ar is a group 5 At least one of which contains one or more deuterium.
The present application aims to provide an organic electroluminescent device composed of a specific luminescent layer host material, wherein the luminescent layer uses a diphenylbenzene-indolo [2,3-A ] carbazole-triazine compound containing deuteration, and a dicarbazole compound also containing deuteration groups; the combination of compounds has a high and balanced carrier mobility. While deuterated groups are simultaneously introduced on the two types of materials, so that the stacking property and chemical stability of the materials can be obviously improved; the two materials are used as the mixed main body material of the green organic electroluminescent device, so that the working voltage of the organic electroluminescent device can be reduced, and the luminous efficiency and the service life of the organic electroluminescent device are improved.
According to a second aspect provided herein, there is provided an electronic device comprising the above organic electroluminescent device.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
Fig. 1 is a schematic structural view of an embodiment of an organic electroluminescent device of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. an organic layer; 310. a hole injection layer; 320. a hole transport layer; 321. a hole transport layer; 322. a hole assist layer; 330. an organic light emitting layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.
Specific embodiments thereof have been shown by way of example in the drawings and will herein be described in more detail. These drawings and the written description are not intended to limit the scope of the inventive concepts in any way, but to illustrate the concepts of the present application to those skilled in the art by reference to specific embodiments.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application. One skilled in the relevant art will recognize, however, that the aspects of the application can be practiced without one or more of the specific details, or with other methods, components, materials, etc. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical idea of the present application.
The application provides an organic electroluminescent device, which comprises a cathode, an anode and an organic layer;
wherein the cathode and the anode are arranged opposite to each other;
the organic layer is located between the cathode and the anode;
the organic layer includes an organic light emitting layer;
the organic light emitting layer includes a first compound and a second compound;
the first compound is selected from compounds shown in formula 1:
therein, L, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
a. b is independently selected from 0, 1, 2, 3, 4 or 5, and a+b is more than or equal to 1;
said L, L 1 、L 2 、Ar 1 、Ar 2 The substituents in (2) are independently selected from halogen group, cyano group, aryl group with 6-12 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triphenylsilyl group, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, heterocycloalkyl group with 2-10 carbon atoms and alkoxy group with 1-10 carbon atoms;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a ring;
each R is 1 、R 2 Or R is 3 Each independently selected from hydrogen, deuterium, a halogen group, cyano, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms;
n 1 Represents a substituent R 1 Number n of (n) 1 Selected from 1,2,3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 1,2,3 or 4, when n 3 When the number is greater than 1, any two R 3 The same or different;
the second compound is selected from compounds represented by formula 2:
wherein R is 4 、R 5 、R 6 、R 7 Independently selected from hydrogen, deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1,2,3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1,2 or 3, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1,2 or 3, when n 6 When the number is greater than 1, any two R 6 The same or different;
n 7 represents a substituent R 7 Number n of (n) 7 Selected from 1,2,3 or 4, when n 7 When the number is greater than 1, any two R 7 The same or different;
L 3 、L 4 the same or different and are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 3 And Ar is a group 4 The same or different and are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
each L 5 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
each Ar is Ar 5 Are independently selected from the group consisting of C atoms6-30 substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
L 3 、L 4 、L 5 、Ar 3 、Ar 4 、Ar 5 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms;
in Ar 3 、Ar 4 And Ar is a group 5 At least one of which contains one or more deuterium.
In this application, the description that "… …" is used to refer to "and" … … "are selected independently and interchangeably, and should be understood in a broad sense, which refers to not only that specific options expressed between the same symbols in different groups do not affect each other, but also that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed, Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. Wherein Rc, the substituent mentioned above, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms.
In the present application, a "substituted" functional group may be substituted with one or more substituents of Rc described above; when two substituents Rc are attached to the same atom, the two substituents Rc may be present independently or attached to each other to form a spiro ring with the atom; when one substituent Rc is present on each of two adjacent carbon atoms in the functional group, the adjacent two substituents Rc may be present independently or fused to the functional group to which they are attached to form a ring.
In the present application, D in the first compound is deuterium.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event may, but need not, occur, and that the description includes instances where the event occurs or does not. For example, "optionally, two adjacent substituents x form a ring" means that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring.
In the present application, "optionally, in Ar 1 、Ar 2 In which any two adjacent substituents form a ring "means that in Ar 1 Or Ar 2 Any of (3)It is intended that two adjacent substituents may or may not form a ring. For example, when Ar 1 When two adjacent substituents form a ring, the number of carbon atoms of the ring can be 5-13, and the ring can be saturated or unsaturated; the ring is for example: cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, fluorene ring, and the like, but is not limited thereto.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms. For example: ar (Ar) 1 Is thatThe number of carbon atoms is 7; l is->The number of carbon atoms is 12.
In this application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, in this application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "alkyl of 1 to 10 carbon atoms" refers to an alkyl group that may include 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Furthermore, alkyl groups may be substituted or unsubstituted.
Alternatively, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In the present application, cycloalkyl refers to saturated hydrocarbons containing alicyclic structures, including monocyclic and fused ring structures. Cycloalkyl groups may have 3-10 carbon atoms, a numerical range such as "3 to 10" referring to each integer in the given range; for example, "cycloalkyl of 3 to 10 carbon atoms" refers to cycloalkyl groups that may include 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Cycloalkyl groups may be substituted or unsubstituted. Examples of cycloalkyl groups are cyclopentylalkyl, cyclohexenyl, adamantyl.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, triphenylene, pyrenyl, benzofluoranthryl, A base, etc.
In this application, a "substituted or unsubstituted aryl group" may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 25, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 20, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group may be from 6 to 12. For example, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 28, 29, 30, although other numbers are possible and are not listed herein. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals, as well as unsubstituted aryl radicals.
As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, alkoxy group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, specific examples of the aryl group as a substituent include, but are not limited to: phenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof comprising 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. For example, in the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 3, 4, 5, 6, 10, 12, 18, 20, 24, 25, 28, 29, 30, although other numbers are possible and are not listed here.
In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, and the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to: pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
In the present application, halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl group, triethylsilyl group and the like.
In the present application, specific examples of the haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, trifluoromethyl.
In the present application, non-positional connection means a single bond extending from a ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formula (X '-1) -formula (X' -4).
The meaning of the non-positional connection or the non-positional substitution is the same as here, and will not be described in detail later.
In the present application, the linking site of carbazole is shown in the figureShown, wherein 1, 2, 3, 4, 5, 6, 7, 8 represent possible ligation sites.
In some embodiments of the present application, in the first compound, R 1 、R 2 、R 3 Each independently selected from hydrogen, deuterium, cyano, fluoro, trifluoromethyl, tridentate methyl, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, phenyl, biphenyl, naphthyl, pyridinyl.
In some embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
Optionally, the substituent in L is selected from fluorine, cyano, alkyl with 1-5 carbon atoms or phenyl.
Alternatively, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene.
More specifically, specific examples of the substituents in L include, but are not limited to: fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In other embodiments of the present application, L is selected from a single bond in the first compound.
In some embodiments of the present application, in the first compound, L is selected from the group consisting of a single bond or:
in some embodiments of the present application, in the first compound, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
Optionally, the L 1 、L 2 The substituents in (a) are each independently selected from fluorine, cyano, alkyl having 1 to 5 carbon atoms or phenyl.
In other embodiments of the present application, in the first compound, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenyl group.
Optionally, the L 1 、L 2 Each of the substituents in (a) is independently selected from fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, in the first compound, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted group T, the unsubstituted group T being selected from the group consisting of:
wherein,represents a chemical bond; the substituted group T contains one or more substituents selected from fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl; and when the substituted group T contains a plurality of substituents, the substituents may be the same or different.
Optionally, in the first compound, L 1 、L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments of the present application, ar 1 、Ar 2 When the aryl group is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 28, 29, 30, although other numbers are possible, and are not specifically mentioned herein. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals, as well as unsubstituted aryl radicals.
In some embodiments of the present application, in the first compound, ar 1 、Ar 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms.
Optionally, the Ar 1 、Ar 2 The substituent groups of the (C) are respectively and independently selected from halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, halogenated alkyl groups with 1-5 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, aryl groups with 6-12 carbon atoms or triphenylsilicon groups;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms.
For example, in Ar 1 And Ar is a group 2 Any two adjacent substituents may form cyclohexaneCyclopentane processBenzene ring, naphthalene ring or fluorene ring->
In other embodiments of the present application, ar in the first compound 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, and substituted or unsubstituted spirobifluorenyl.
Optionally, the Ar 1 、Ar 2 The substituents of (a) are each independently selected from fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, triphenylsilyl, trimethylsilyl, cyclohexenyl, adamantyl, phenyl, biphenyl.
Optionally in Ar 1 、Ar 2 Any two adjacent substituents form a benzene ring or naphthalene ring or fluorene ring.
In other embodiments of the present application, ar in the first compound 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V contains one or more substituents selected from fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, adamantylTrifluoromethyl, triphenylsilyl, phenyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
Optionally, in the first compound, the Ar 1 、Ar 2 Each independently selected from the group consisting of:
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in some embodiments of the present application, in the first compound, a is 5 and b is selected from 0 or 5.
In some embodiments of the present application, wherein Ar is 1 、Ar 2 Each independently selected from the group consisting of:
in some embodiments of the present application, the first compound, formula 1Selected from the following structures:
in deuteration of phenyl groups around the diphenyl benzene, at least one phenyl group is generally selected for perdeuteration in order to reduce the volume of the diphenyl groups and make the spatial overlap of the diphenyl groups and the triazine groups more compact.
In some embodiments of the present application, in the first compound,the connection mode of the three benzene rings is 1,3,5 when connected>The molecular transmission performance is more balanced, the voltage of the organic electroluminescent device can be reduced, and the luminous efficiency of the luminous device can be improved. />
In some more specific embodiments, the Ar 1 、Ar 2 Each independently selected from the group consisting of:
in formula 1Selected from the following structures:
l is a single bond;
L 1 、L 2 each independently selected from the group consisting of a single bond or:
optionally, the first compound is selected from the group consisting of:
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in some embodiments of the present application, the second compound is selected from compounds represented by the following chemical formula:
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in some embodiments of the present application, each R in the second compound 4 、R 5 、R 6 、R 7 Independently selected from hydrogen, deuterium, halogen groups, cyano groups, alkyl groups of 1-5 carbon atoms, or
In a preferred embodiment of the present application, each R 4 、R 5 、R 6 、R 7 One of them isAnd Ar is Ar 5 Containing 1 or more deuterium.
Alternatively, each R 4 、R 5 、R 6 、R 7 Each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl.
Alternatively, each L 5 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.
Alternatively, each L 5 Specific examples of substituents include, but are not limited to: deuterium, halogen group, cyano, alkyl group having 1 to 5 carbon atoms, phenyl group.
In some embodiments of the present application, each L 5 Independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstitutedA substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group.
Alternatively, each L 5 The substituents in (a) are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl.
In some embodiments of the present application, each L 5 Each independently selected from single bond, substituted or unsubstituted group V 1 Unsubstituted group V 1 Selected from the group consisting of:
wherein,represents a chemical bond; substituted group V 1 Containing one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; and when the substituted group V 1 When a plurality of substituents are contained, the substituents may be the same or different.
In some embodiments of the present application, each L 5 Each independently selected from the group consisting of a single bond, or:
in some embodiments of the present application, each Ar 5 Each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.
Alternatively, each Ar 5 The substituents in (2) are independently selected from deuterium, cyano, halogen group, alkyl group with 1-5 carbon atoms, and aryl group with 6-12 carbon atoms.
In some embodiments of the present application, each Ar 5 Identical or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstitutedSubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene.
Alternatively, each Ar 5 The substituents of (2) are each independently selected from deuterium, cyano, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In some embodiments of the present application, each Ar 5 Each independently selected from substituted or unsubstituted groups G 1 Unsubstituted group G 1 Selected from the group consisting of:
wherein,represents a chemical bond; substituted group G 1 Containing one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, biphenyl; and when the substituted group G 1 When a plurality of substituents are contained, the substituents may be the same or different.
Alternatively, each Ar 5 Each independently selected from the group consisting of:
in some embodiments of the present application, L 3 、L 4 Independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Alternatively, L 3 And L 4 The substituents in (2) are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, and aryl group with 6-12 carbon atoms.
Alternatively, L 3 、L 4 Independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a heteroarylene group having 12 to 18 carbon atoms.
In some embodiments of the application, L 3 、L 4 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or substituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazole group.
Optionally, the L 3 And L 4 The substituents in (a) are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl.
In some embodiments of the present application, L 3 And L 4 Each independently selected from a single bond or a substituted or unsubstituted group G 2 Unsubstituted group G 2 Selected from the group consisting of:
wherein,represents a chemical bond; substituted group G 2 Containing one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; and when the substituted group G 2 When a plurality of substituents are contained, the substituents may be the same or different.
Alternatively, L 3 And L 4 Each independently selected from the group consisting of a single bond or:
in some embodiments of the present application, ar 3 And Ar is a group 4 Each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
Alternatively, ar 3 And Ar is a group 4 Each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms and heteroaryl groups having 12 carbon atoms.
Alternatively, ar 3 And Ar is a group 4 The substituents of (2) are each independently selected from deuterium, cyano, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In some embodiments of the present application, ar 3 And Ar is a group 4 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted triphenylene.
Optionally, the Ar 3 And Ar is a group 4 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In some embodiments of the present application, ar 3 And Ar is a group 4 Each independently selected from substituted or unsubstituted groups G 3 Unsubstituted group G 3 Selected from the group consisting of:
wherein,represents a chemical bond; substituted group G 3 Containing one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, biphenyl; and when the substituted group G 3 When a plurality of substituents are contained, the substituents may be the same or different.
Alternatively, ar 3 And Ar is a group 4 Each independently selected from the group consisting of:
in some embodiments of the present application, ar in the second compound 3 、Ar 4 And Ar is a group 5 Is selected from at least one deuterium substituted group selected from the group consisting of:
alternatively, ar 3 、Ar 4 And Ar is a group 5 Is selected from at least one deuterium substituted group selected from the group consisting of:
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alternatively, ar 3 、Ar 4 And Ar is a group 5 And only one of which contains deuterium substitution.
Optionally, the second compound is selected from the group consisting of:
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the application provides an organic electroluminescent device comprising an anode and a cathode which are oppositely arranged, a cathode, an anode and an organic layer. The organic layer includes an organic light emitting layer including a first compound and a second compound.
In some embodiments of the present application, the first compound and the second compound are used as host materials for the organic light emitting layer by mixing.
In some embodiments of the present application, the relative content of the two types of compounds in the organic light emitting layer is not particularly limited, and may be selected according to the specific application of the organic electroluminescent device. Generally, the first compound may be 1% to 99% by mass and the second compound may be 1% to 99% by mass, based on the total weight of the two compounds. For example, the mass ratio of the first compound to the second compound may be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30 80:20, 99:1, etc.
In some embodiments of the present application, the first compound is present in an amount of 20% to 80% by mass and the second compound is present in an amount of 20% to 80% by mass, based on the total weight of the two compounds.
In some preferred embodiments, the first compound is present in an amount of 30% to 60% by mass and the second compound is present in an amount of 40% to 70% by mass, based on the total weight of the two compounds. Preferably, the mass percentage of the first compound is 40% -60%, and the mass percentage of the second compound is 40% -60%. More preferably, the mass percentage of the first compound is 40% -50%, and the mass percentage of the second compound is 50% -60%.
In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.
In some embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device.
In some aspects of the present application, an organic electroluminescent device includes an anode (ITO substrate), a hole transport layer, a hole assist layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (mg—ag mixture), and an organic capping layer in this order.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200 disposed opposite to the anode 100, and at least one organic layer 300 interposed between the anode layer and the cathode layer, the organic layer 300 including a hole injection layer 310, a hole transport layer 321, a hole auxiliary layer 322, an organic light emitting layer 330, an electron transport layer 350, and an electron injection layer 360, which are sequentially stacked.
Optionally, a hole blocking layer 340 may be disposed between the organic light emitting layer 330 and the electron transport layer 350. The organic light emitting layer 330 may contain the organic compound described in the first aspect of the present application.
Alternatively, the anode 100 includes an anode material, which is preferably a material having a large work function that facilitates hole injection into the organic layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxygenCompounds such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene ](PEDT), polypyrrole, and polyaniline, but not limited thereto. A transparent electrode including Indium Tin Oxide (ITO) as an anode is preferable.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, in some embodiments of the present application, hole transport layer 321 consists of HT-01.
Alternatively, the hole auxiliary layer 322 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, in some embodiments of the present application, hole assist layer 322 is comprised of HT-02.
Alternatively, the organic light emitting layer 330 may include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein.
In one embodiment of the present application, the host material of the organic light emitting layer 330 is composed of the composition GH-X provided herein, including an electron-type host material (GH-N), a hole-type host material (GH-P).
In some embodiments of the present application, a green organic electroluminescent device, the organic light-emitting layer 330 includes a first compound, a second compound, and a guest as described hereinMaterial Ir (mppy) 3 。
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in this application. For example, in some embodiments of the present application, electron transport layer 350 may be composed of ET-01 and LiQ.
Optionally, a hole blocking layer 340 is disposed between the organic light emitting layer 330 and the electron transport layer 350. The hole blocking layer may include one or more hole blocking materials, which are not particularly limited in this application.
Alternatively, the cathode 200 includes a cathode material, which is a material having a small work function that facilitates electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. A metal electrode comprising silver and magnesium is preferably included as a cathode.
Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. In some embodiments of the present application, hole injection layer 310 may be composed of TiOPC.
Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).
The application also provides an electronic device comprising the organic electroluminescent device.
For example, as shown in fig. 2, the electronic device provided in the present application is a first electronic device 400, where the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, the first electronic device has the same beneficial effects, and the description thereof is omitted herein.
The present application will be described in detail below in connection with examples, but the following description is intended to explain the present application and is not intended to limit the scope of the present application in any way.
Synthetic examples
In the synthesis examples described below, all temperatures are in degrees celsius unless otherwise indicated. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company, arco Chemical Company and Alfa ChemicalCompany, and some intermediates that could not be purchased directly were prepared by simple reactions from commercially available starting materials, and were used without further purification unless otherwise stated. The rest conventional reagents are purchased from Tianjin good-house chemical limited company, tianjin Fuchen chemical reagent factory, wuhan Xinhua far-tech development limited company, qingdao Tenglong chemical reagent limited company, qingdao marine chemical factory and the like. The reactions in each synthesis example are typically carried out under nitrogen or argon positive pressure, or a dry tube is placed over anhydrous solvent (unless otherwise stated); in the reaction, the reaction flask was capped with a suitable rubber stopper and the substrate was injected into the flask via syringe. The individual glassware used was dried.
In purification, the chromatographic column is a silica gel column, and silica gel (100-200 mesh) is purchased from Qingdao ocean chemical plant.
In each synthesis example, the measurement conditions for low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage HPLC-M (column type: zorbax SB-C18, 2.1X130 mm,3.5 μm, 6min, flow rate 0.6mL/min. Mobile phase: 5% -95% (acetonitrile with 0.1% formic acid) in water with 0.1% formic acid) was detected by electrospray ionization (ESI) at 210nm/254nm with UV.
Nuclear magnetic resonance hydrogen spectrum: bruker 400MHz nuclear magnetic instrument, CD at room temperature 2 Cl 2 TMS (0 ppm) was used as a reference standard for solvents (in ppm).
Synthesis of intermediate a 1-1:
2-bromo-5-chloro-1-iodobenzene (31.22 g;98.42 mmol), phenylboronic acid (10 g;82.01 mmol), tetrakis (triphenylphosphine) palladium (0.95 g;0.82 mmol), potassium carbonate (24.94 g;180.43 mmol), tetrabutylammonium bromide (2.64 g;8.20 mmol), toluene (240 mL), ethanol (60 mL) and deionized water (60 mL) were added to a round-bottomed flask, and the mixture was stirred and warmed to 78℃under nitrogen protection for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as an eluent to give intermediate a1-1 (14.49 g; yield 66%) as a pale yellow solid.
Using a method similar to the synthesis of intermediate a1-1, reactant A in Table 1 below was used in place of phenylboronic acid and reactant B was used in place of 2-bromo-5-chloro-1-iodobenzene to synthesize the intermediate compounds shown in the following tables:
table 1:
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synthesis of intermediate a 1-2:
intermediate a1-1 (10.51 g;39.37 mmol), deuterated phenylboronic acid (5.0 g;39.37 mmol), tetrakis (triphenylphosphine) palladium (0.45 g;0.39 mmol), potassium carbonate (11.97 g;86.6 mmol), tetrabutylammonium bromide (1.30 g;3.93 mmol), toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to a round-bottomed flask and stirred under nitrogen at a temperature of 78℃for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane as eluent gave a1-2 (7.43 g; yield 70%)
Using a similar procedure to the synthesis of intermediate a1-2, the intermediate compound shown in Table 2 below was synthesized using reactant C in place of deuterated phenylboronic acid and reactant D in place of a1-1 in Table 2 below:
table 2:
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synthesis of intermediate a 1-3:
indolo (2, 3-A) carbazole (5.0 g;19.51 mmol), a1-2 (5.26 g;19.5 mmol), tris (dibenzylideneacetone) dipalladium (0.18 g;0.20 mmol), x-phos (0.16 g;0.39 mmol), sodium tert-butoxide (2.81 g;29.26 mmol) and xylene (100 mL) were added to a round bottom flask and reacted under nitrogen at 135℃for 16 hours with stirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane as eluent gave a1-3 (7.16 g; yield 75%).
Using a similar procedure to the synthesis of intermediates a1-3, using reactant E in Table 3 below in place of a1-2, the intermediate compounds shown in Table 3 below were synthesized:
table 3:
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preparation example 1: synthesis of Compound 1:
intermediate a1-3 (5.0 g;10.21 mmol), reactant i1 (2.73 g;10.21 mmol) and N, N-Dimethylformamide (DMF) (50 mL) were added to a round bottom flask, the temperature of the system was reduced to-5℃under nitrogen, and then sodium hydride (0.37 g,15.32 mmol) was added to continue the reaction at room temperature for 12h; washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane as eluent followed by recrystallization purification using a toluene/n-heptane solvent system yielded compound 1 (4.4 g, 60%)
Using a similar method to the synthesis of compound 1, the compounds shown in table 4 below were synthesized using reactant F instead of intermediates a1-3 and reactant G instead of reactant i1 in table 4 below:
table 4:
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mass spectrum data for the compounds are shown in table 5:
table 5:
| compound 1 | m/z＝721.3(M+H) + | Compound 8 | m/z＝771.3(M+H) + |
| Compound 13 | m/z＝815.4(M+H) + | Compound 41 | m/z＝726.3(M+H) + |
| Compound 32 | m/z＝797.3(M+H) + | Compound 50 | m/z＝876.4(M+H) + |
| Compound 39 | m/z＝873.3(M+H) + | Compound 58 | m/z＝847.3(M+H) + |
| Compound 43 | m/z＝802.4(M+H) + | Compound 70 | m/z＝855.4(M+H) + |
| Compound 53 | m/z＝797.3(M+H) + | Compound 78 | m/z＝842.3(M+H) + |
| Compound 65 | m/z＝852.4(M+H) + | Compound 90 | m/z＝964.4(M+H) + |
| Compound 75 | m/z＝739.2(M+H) + | Compound 93 | m/z＝797.3(M+H) + |
| Compound 85 | m/z＝822.3(M+H) + |
Preparation example 19: synthesis of Compound 2-401
SM-A-1(10g;30.08mmol),SM-B-1(4.89g;30.08mmol),tris(dibenzylideneacetone)dipalladium(0.28g;0.3mmol),2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl(0.25g;0.60mmol),sodiumt-butoxide(4.34g;45.13mmol),xylene(100mL)wereaddedtoaroundbottomflaskandreactedundernitrogenat135℃for16hourswithstirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent gave SM-1 (4.6 g, 37% yield).
Referring to the method for SM-11, using A in the following table instead of SM-B, the intermediate compounds SM-X shown in Table 6 below were synthesized:
TABLE 6
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SM-1 (5 g;12.11 mmol), SM-C-1 (3.19 g;12.11 mmol), tris (dibenzylideneacetone) dipalladium (0.11 g;0.12 mmol), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.10 g;0.24 mmol), sodium t-butoxide (1.75 g;18.16 mmol), xylene (100 mL) were added to a round bottom flask and reacted under nitrogen at 135℃with stirring for 16 hours; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent afforded 2-401 (5.77 g, 80% yield).
Referring to the synthesis of compounds 2-401, compound P shown in the following Table was synthesized using N instead of SM-1,O instead of SM-C-1 in Table 7 below.
TABLE 7
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Synthesis of intermediate A-1:
to a 500mL round bottom flask that was dried and replaced with nitrogen was added 2, 4-dichloronitrobenzene (30 g,156.25 mmol), 2-biphenylboronic acid (31.73 g,156.25 mmol), tetrakis (triphenylphosphine) palladium (9.03 g,7.81 mmol), tetrabutylammonium bromide (2.52 g,7.81 mmol), potassium carbonate (64.79 g,468.75 mmol), toluene (240 mL), ethanol (120 mL), deionized water (60 mL), and the temperature was raised to 75-80℃with stirring for 8h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirring was performed for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using 1:6 dichloromethane/n-heptane as mobile phase to give intermediate A-1 (34.43 g; 70%).
To a dried and nitrogen-purged round bottom flask was added intermediate A-1 (30 g,95.29 mmol), triphenylphosphine (62.49 g,238.25 mmol), o-dichlorobenzene (300 mL), and the temperature was raised to 170℃with stirring for 18h; then the reaction mixture was cooled to room temperature, o-dichlorobenzene was distilled off under normal pressure, toluene (200 mL) was added, stirring was carried out for 15 minutes, and then the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using methylene chloride/n-heptane as mobile phase to give intermediate A-2 (13.47 g; 50%).
To a dried and nitrogen-purged round bottom flask was added intermediate A-2 (10 g,35.36 mmol), iodobenzene (10.82 g,53.04 mmol), cuprous iodide (0.67 g,3.54 mmol), potassium carbonate (12.12 g,88.40 mmol), phenanthroline (0.35 g,1.77 mmol), 18-crown-6 (0.93 g,3.54 mmol), DMF (100 mL), and the mixture was warmed to 150℃with stirring for 16h; the reaction mixture was then cooled to room temperature, ethyl acetate (200 mL) and deionized water (200 mL) were added, stirred for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using methylene chloride/n-heptane as mobile phase to give intermediate A-3 (8.25 g; 65%).
Synthesis of Compound 2-409 from preparation 39
A-3 (10 g;27.86 mmol), M-1 (10.12 g;27.86 mmol), tetrakis (triphenylphosphine) palladium (1.61 g;1.39 mmol), potassium carbonate (5.78 g;41.79 mmol), tetrabutylammonium bromide (0.44 g;1.39 mmol), toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to a round-bottomed flask, and the mixture was stirred and warmed to 78℃under nitrogen protection for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as an eluent to give compound 2-409 (12.52 g; yield 70%).
M-2 (30 g;104.49 mmol), deuterated bromobenzene (16.92 g;104.49 mmol), tetrakis (triphenylphosphine) palladium (6.03 g;5.22 mmol), potassium carbonate (21.66 g;156.74 mmol), tetrabutylammonium bromide (1.68 g;5.22 mmol), toluene (240 mL), ethanol (120 mL) and deionized water (60 mL) were added to a round-bottomed flask, and the mixture was stirred and warmed to 78℃under nitrogen protection for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by column chromatography on silica gel using methylene chloride/n-heptane as eluent to give B-1 (23.72 g; yield 70%).
B-1 (23 g;70.89 mmol), N-bromosuccinimide (12.62 g;70.89 mmol), methylene chloride (240 mL) were added to a round bottom flask and reacted under nitrogen at room temperature with stirring for 16 hours; the reaction mixture was washed with water, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as eluent to give B-2 (20.01 g; yield 70%).
Synthesis of Compound 2-388 of preparation 40
B-2 (10 g;27.87 mmol), M-3 (10.12 g;27.86 mmol), tetrakis (triphenylphosphine) palladium (1.61 g;1.39 mmol), potassium carbonate (7.70 g;55.73 mmol), tetrabutylammonium bromide (0.39 g;1.39 mmol), toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to a round-bottomed flask, and the mixture was stirred and warmed to 78℃under nitrogen protection for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as an eluent to give compound 2-388 (10.7 g; yield 60%).
Synthesis of Compound 2-393 from preparation 41
B-2 (10 g;24.79 mmol), M-4 (9.76 g;24.79 mmol), tetrakis (triphenylphosphine) palladium (1.43 g;1.24 mmol), potassium carbonate (5.14 g;37.19 mmol), tetrabutylammonium bromide (0.39 g;1.24 mmol), toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to a round-bottomed flask, and the mixture was stirred and warmed to 78℃under nitrogen protection for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as an eluent to give compound 2-393 (11.99 g; yield 72%).
Mass spectrum data of the above compounds are shown in the following table 8
TABLE 8
| Compounds of formula (I) | Mass spectral data | Compounds of formula (I) | Mass spectral data |
| 2-401 | m/z＝596.3[M+H] + | 2-399 | m/z＝580.2[M+H] + |
| 2-383 | m/z＝655.3[M+H] + | 2-382 | m/z＝718.3[M+H] + |
| 2-344 | m/z＝640.3[M+H] + | 2-342 | m/z＝731.3[M+H] + |
| 2-4 | m/z＝566.3[M+H] + | 2-8 | m/z＝616.3[M+H] + |
| 2-384 | m/z＝655.3[M+H] + | 2-385 | m/z＝731.3[M+H] + |
| 2-352 | m/z＝656.3[M+H] + | 2-356 | m/z＝672.3[M+H] + |
| 2-359 | m/z＝718.3[M+H] + | 2-364 | m/z＝718.3[M+H] + |
| 2-369 | m/z＝672.3[M+H] + | 2-376 | m/z＝731.3[M+H] + |
| 2-373 | m/z＝718.3[M+H] + | 2-388 | m/z＝643.3[M+H] + |
| 2-408 | m/z＝737.3[M+H] + | 2-409 | m/z＝642.3[M+H] + |
| 2-393 | m/z＝672.3[M+H] + |
The nuclear magnetic data of some compounds are shown in table 9 below:
TABLE 9
Preparation and performance evaluation of organic electroluminescent devices
Example 1
Green organic electroluminescent device
An anode is formed of Indium Tin Oxide (ITO) on a substrate with a reflective layer formed thereon, and has a thickness ofCut into dimensions of 40mm by 0.7mm, and prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process,cleaning the surface of the ITO substrate by adopting an organic solvent to remove impurities on the surface of the ITO substrate; or by ultraviolet ozone and O 2 :N 2 Plasma surface treatment to increase the work function of the anode.
Vacuum deposition of TiOPC by PVD at substrate anode to form a thicknessIs deposited on the hole injection layer>HT-01 of (A) forms a hole transport layer.
Vapor deposition on hole transport layerHT-02 of (A) forms a hole assist layer.
GH-1 and Ir (mppy) are deposited on the hole-assist layer 3 100%: co-evaporation was performed at a rate of 10% to form a film having a thickness ofAn organic light emitting layer (green organic light emitting layer).
Evaporating ET-01 and LiQ in a ratio of 1:1 to formA thick electron transport layer formed by vapor deposition of Yb on the electron transport layer to a thickness +.>Is formed by co-evaporating magnesium and silver on the electron injection layer at a vapor deposition ratio of 1:9>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAn organic capping layer (CPL) is formed, thereby realizing the preparation of an organic light emitting device.
Examples 2 to 24:
in forming the organic light emitting layer, an organic electroluminescent device was fabricated by the same method as in example 1, substituting the composition GH-1 in example 1 with the composition of GH-X-based host material shown in table 11.
Comparative examples 1 to 5:
an organic electroluminescent device was prepared in the same manner as in device example 1, except that GH-X was used in forming the organic light-emitting layer.
In the above examples and comparative examples, the host materials GH-X used were obtained by mixing the first compound of preparation examples 1 to 18 and the second compound of preparation examples 19 to 40, respectively, and the specific compositions are shown in Table 10, wherein the mass ratio refers to the ratio of the mass percentages of the compounds shown in the front and the compounds shown in the rear. Taking the composition GH-1 as an example, it is clear from Table 11 that GH-1 is prepared by mixing compound 1 and compound 2-4 in a mass ratio of 50:50; as can be seen from Table 10, GH-D1 is obtained by mixing compound I and compound 2-401 in a mass ratio of 40:60, taking the host material GH-D1 as an example.
The material structures used in device examples 1-26 and comparative examples 1-3 are shown in Table 10 below:
table 10
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The device performance was analyzed under the conditions, and the results are shown in table 11 below.
TABLE 11
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As can be seen from the results in Table 11, the voltage of the examples was reduced by at least 0.29V, the current efficiency Cd/A was increased by at least 24.8%, the external quantum efficiency was increased by at least 25.1%, and the lifetime was increased by at least 55.25% as compared with comparative examples 1 to 3.
From the above results, it is apparent that the present application provides an organic electroluminescent device composed of a specific light-emitting layer host material, which has significantly improved device performance compared to comparative examples 1 to 3. The reason for this may be that the first compound used in this application uses a specific fused version of the indolo [2,3-a ] carbazole group, combining a diaryl substituted triazine with a deuterated diphenyl group; aryl on a triazine group in the molecular structure does not have deuteration, and the diaryl triazine and the diphenyl phenyl group have overlapped spatial position relation and have space conjugation property, so that the material has enhanced electron transmission capability; the volume of the diphenyl phenyl group can be reduced by deuteration on the phenyl at the periphery of the diphenyl benzene, so that the spatial overlapping of the diphenyl phenyl group and the triazine group is more compact, and the electron transmission characteristic is further improved; the organic light-emitting device is applied to a main material of a light-emitting layer of the phosphorescent organic light-emitting device, so that the light-emitting layer has good electron transmission characteristics, the charge balance and exciton recombination efficiency are promoted, and the device has reduced voltage, improved light-emitting efficiency and service life characteristics.
As can be seen from the above table, in the first compound,the connection mode of the three benzene rings is 1,3 and 5 when connectedThe molecular transmission performance is more balanced, the voltage of the organic electroluminescent device can be effectively reduced, and the efficiency of the device is improvedAnd lifetime.
Next, the organic light-emitting layer of the present application uses a compound containing deuterated diphenyl-indolo [2,3-A ]]Carbazole-triazine compounds, as well as biscarbazoles containing deuterated groups; the combination of compounds has a high and balanced carrier mobility. While deuterated groups are simultaneously introduced on the two types of materials, so that the stacking property and chemical stability of the materials can be obviously improved; the two materials are used as the mixed main body material of the green organic electroluminescent device, so that the working voltage of the organic electroluminescent device can be reduced, and the luminous efficiency and the service life of the organic electroluminescent device are improved. In particular, in the case of the biscarbazoles, whenIn position 5 of the dicarbazole, and Ar 5 Containing deuterated groups and deuterated diphenylbenzene-indolo [2,3-A ]]When the carbazole-triazine compound is used as a main body material of an organic electroluminescent device after being mixed, the device performance is optimal.
Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the application following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the application pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims. It is to be understood that the present application is not limited to the precise arrangements and instrumentalities shown in the drawings, which have been described above, and that various modifications and changes may be effected without departing from the scope thereof. The scope of the application is limited only by the appended claims.
Claims (6)
1. An organic electroluminescent device includes a cathode, an anode, and an organic layer;
wherein the cathode and the anode are arranged opposite to each other;
the organic layer is located between the cathode and the anode;
the organic layer includes an organic light emitting layer;
the organic light emitting layer includes a first compound and a second compound;
the first compound is selected from compounds shown in formula 1:
wherein L is selected from a single bond, a substituted or unsubstituted phenylene group;
the substituent in L is selected from fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl;
L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene;
L 1 、L 2 each of the substituents in (a) is independently selected from fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, and substituted or unsubstituted spirobifluorenyl;
Ar 1 、Ar 2 wherein each substituent is independently selected from fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, trifluoromethyl, adamantyl, phenyl;
a is 5, b is selected from 0 or 5;
each R is 1 、R 2 Or R is 3 Each independently selected from hydrogen, deuterium, halogen groups, and cyano;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 1,2,3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 1,2,3 or 4, when n 3 When the number is greater than 1, any two R 3 The same or different;
the second compound is selected from compounds represented by formulas 2-3-3:
wherein R is 4 Selected from hydrogen orR 5 、R 6 、R 7 Selected from hydrogen;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1,2,3 or 4, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 3;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 3;
n 7 represents a substituent R 7 Number n of (n) 7 Selected from 4;
L 3 and L 4 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or substituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazole group;
L 3 and L 4 Wherein each substituent is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl;
each L 5 Selected from single bonds;
Each Ar is Ar 5 Selected from substituted or unsubstituted phenyl;
each Ar is Ar 5 Wherein the substituents are selected from deuterium;
Ar 3 and Ar is a group 4 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted triphenylene;
Ar 3 and Ar is a group 4 Wherein each substituent is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl;
in Ar 3 、Ar 4 And Ar is a group 5 At least one of which contains one or more deuterium.
2. The organic electroluminescent device according to claim 1, wherein, in the first compound, ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V contains one or more substituents selected from fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, adamantyl, phenyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
3. The organic electroluminescent device of claim 1, wherein the first compound is selected from the group consisting of:
4. the organic electroluminescent device according to claim 1, wherein, in the second compound, ar 3 、Ar 4 At least one of which is a deuterium substituted group selected from the group consisting of:
Ar 5 at least one of which is a deuterium substituted group selected from the group consisting of:
5. the organic electroluminescent device of claim 1, wherein the second compound is selected from the group consisting of:
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6. an electronic device comprising the organic electroluminescent device as claimed in any one of claims 1 to 5.
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| CN112103395A (en) * | 2020-08-10 | 2020-12-18 | 陕西莱特光电材料股份有限公司 | Organic electroluminescent device and electronic apparatus |
| KR102193015B1 (en) * | 2020-03-11 | 2020-12-18 | 주식회사 엘지화학 | Organic light emitting device |
| CN112375083A (en) * | 2020-11-19 | 2021-02-19 | 陕西莱特光电材料股份有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR102193015B1 (en) * | 2020-03-11 | 2020-12-18 | 주식회사 엘지화학 | Organic light emitting device |
| CN112103395A (en) * | 2020-08-10 | 2020-12-18 | 陕西莱特光电材料股份有限公司 | Organic electroluminescent device and electronic apparatus |
| CN112375083A (en) * | 2020-11-19 | 2021-02-19 | 陕西莱特光电材料股份有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
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