CN115700269A - Organic electroluminescent composition and application thereof - Google Patents
Organic electroluminescent composition and application thereof Download PDFInfo
- Publication number
- CN115700269A CN115700269A CN202110875588.5A CN202110875588A CN115700269A CN 115700269 A CN115700269 A CN 115700269A CN 202110875588 A CN202110875588 A CN 202110875588A CN 115700269 A CN115700269 A CN 115700269A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- phenyl
- carbazolyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 26
- 230000005525 hole transport Effects 0.000 claims abstract description 23
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 17
- -1 phenyl-substituted carbazolyl Chemical group 0.000 claims description 156
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 60
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 36
- 239000010410 layer Substances 0.000 claims description 34
- 125000001624 naphthyl group Chemical group 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 28
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 239000004305 biphenyl Substances 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 235000010290 biphenyl Nutrition 0.000 claims description 19
- 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 17
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- OSOLELDZBFOFHO-UHFFFAOYSA-N 2-phenylphenanthrene Chemical class C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3C=CC2=C1 OSOLELDZBFOFHO-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000005878 benzonaphthofuranyl group Chemical class 0.000 claims description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000005509 dibenzothiophenyl group Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000004957 naphthylene group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical class C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000004306 triazinyl group Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002178 anthracenyl group Chemical class C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 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 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical group C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 2
- MOWKTPHUWHQZSC-UHFFFAOYSA-N 3h-naphtho[1,2-g]indole Chemical group C1=CC=C2C3=CC=C4C=CNC4=C3C=CC2=C1 MOWKTPHUWHQZSC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 60
- 238000003786 synthesis reaction Methods 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- 238000000921 elemental analysis Methods 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000758 substrate Substances 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
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical group OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical group OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- VUYVXCJTTQJVKJ-UHFFFAOYSA-L palladium(2+);tricyclohexylphosphane;dichloride Chemical compound Cl[Pd]Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 VUYVXCJTTQJVKJ-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic electroluminescent composition and application thereof, wherein the organic electroluminescent composition comprises a fused heterocyclic compound containing a quinazoline structure and a hole transport type compound, and the fused heterocyclic compound containing the quinazoline structure is a compound with a structure shown as a formula (1-1) or a formula (1-2). The organic electroluminescent composition can enable an OLED device to have lower driving voltage, higher current efficiency and longer service life.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and relates to an organic electroluminescent composition and application thereof.
Background
An Electroluminescent (EL) device is a self-luminous device, which is advantageous in that it provides a wide viewing angle, a large contrast ratio, and a fast response time.
The most important factor determining the luminous efficiency of an organic EL device is a light emitting material. Heretofore, fluorescent materials have been widely used as light emitting materials. However, in view of the electroluminescent mechanism, since phosphorescent materials theoretically enhance the luminous efficiency four (4) times as compared to fluorescent materials, phosphorescent light-emitting materials are being widely studied. Iridium (III) complexes have been widely referred to as phosphorescent materials. Currently, 4'-N, N' -dicarbazole-biphenyl (CBP) is the most well known host material for phosphorescent materials. But it has the following disadvantages: (1) Due to its low glass transition temperature and poor thermal stability, it may degrade in vacuum during high temperature deposition processes. (2) The power efficiency of the organic EL device is given by [ (pi/voltage) × current efficiency ], and the power efficiency is inversely proportional to the voltage. Although organic EL devices including phosphorescent host materials provide higher current efficiency (cd/a) than organic EL devices including fluorescent materials, significantly high driving voltages are necessary. Therefore, there is no advantage in terms of power efficiency (1 m/W). (3) Further, the organic EL device has a short lifetime, and improvement in luminous efficiency is still required. In order to solve the problem of the aforementioned phosphorescent material, it has been attempted to form a light-emitting layer having two or more host compounds.
WO2011/136755 and WO2013/146645 disclose organic electroluminescent devices in which the light-emitting layer comprises two or more host compounds including indolocarbazole-based compounds. However, the luminous efficiency, lifetime, and the like of the indolocarbazole compounds disclosed in the references are to be further improved.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic electroluminescent composition and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the invention provides an organic electroluminescent composition, which comprises a fused heterocyclic compound containing a quinazoline structure and a hole transport type compound, wherein the fused heterocyclic compound containing the quinazoline structure is a compound having a structure shown as a formula (1-1) or a formula (1-2),
l is selected from a linkage, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C5-C30 heteroarylene,
ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C5-C60 heteroarylamine and substituted or unsubstituted C5-C60 arylheteroarylamine,
R 1 -R 3 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy,
R n1 -R n8 、R m1 -R m6 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy.
In the invention, through the matching of the fused heterocyclic compound containing the quinazoline structure and the hole-transport compound, the combination of electrons and holes is stronger, which is more beneficial to the improvement of luminous efficiency and the prolonging of the service life of devices.
Preferably, ar is selected from the following carbazole groups:
R 4 -R 11 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl wherein one or more methylene groups are substituted by-O-or-S-in such a way that the O atom or S atom is not adjacent, substituted or unsubstitutedC2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are replaced by-O-or-S-in such a way that O atoms or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C5-C60 heteroarylamino, substituted or unsubstituted C5-C60 arylheteroaryl, R arylamino 4 -R 11 Each independently exists or the two adjacent exist and are connected to form a ring A; and/or R 4 And R 11 Through a benzene ring or a naphthalene ring;
preferably, the ring a is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted benzindole ring, a substituted or unsubstituted naphthoindole ring;
preferably, R 4 -R 11 Any two adjacent of them are fused with benzene ring, and/or R 4 And R 11 Through benzene ring or naphthalene ring;
preferably, R 4 -R 11 Each independently selected from the group consisting of substituted or unsubstituted: phenyl, carbazolyl, phenyl-substituted carbazolyl, biphenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzofuran-substituted carbazolyl, terphenyl-substituted carbazolyl;
preferably, R 4 -R 11 Either one of them is combined with
The connection is carried out by connecting the two parts,
L 1 selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 1 、Ar 2 each independently selected from substituted or unsubstitutedThe following groups: phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, biphenyl-substituted carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl;
preferably, ar is selected from
W is selected from O, S, NL 2 Ar 3 、CR 16 R 17 ，
L 2 Selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 3 selected from phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl substituted naphthyl, naphthyl substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuran substituted phenyl, dibenzothiophenyl substituted phenyl, dimethylfluorenyl substituted phenyl, diphenylfluorenyl substituted phenyl, spirobifluorenyl,
R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 each independently selected from hydrogen, deuterium, phenyl and/or adjacent two thereof are connected to form a benzene ring,
R 16 、R 17 each independently selected from methyl, phenyl, or R 16 、R 17 The bonding is carried out to form a fluorenyl group,
and/or R 4 And R 11 Through a benzene ring or a naphthalene ring.
More preferably, ar is selected from the group consisting of substituted or unsubstituted:
wherein the wavy line represents the attachment site of the group.
Preferably, ar is selected from the group consisting of substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, quinazolyl, 2-phenylphenanthrene [3,4-d ] oxazolyl, 2-phenylphenanthrene [3,4-d ] thiazolyl.
Preferably, R n1 -R n8 、R m1 -R m6 Each independently selected from the group consisting of substituted or unsubstituted hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, 2-phenylphenanthrene [3,4-d ] phenyl]Oxazolyl, 2-phenylphenanthrene [3,4-d ]]A thiazolyl group.
Preferably, L is selected from the group consisting of a linker, phenylene, biphenylene, naphthylene, dibenzofuranylene.
When each group contains a substituent as described above, the substituents are independently selected from deuterium, halogen, cyano, unsubstituted or R ' substituted C1-C6 alkyl, unsubstituted or R ' substituted C6-C12 aryl, unsubstituted or R ' substituted C2-C20 heteroaryl;
r' is selected from deuterium, halogen, cyano, deuterium-substituted methyl and halogen-substituted methyl;
preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthyl substituted phenyl, dimethylfluorenyl, diphenyl substituted fluorenyl, spirobifluorenyl,
preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzocarbazolyl, dibenzocarbazolyl,
preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, adamantyl.
Preferably, the quinazoline structure-containing compound having the structure shown in formula (1-1) is any one of the following compounds:
preferably, the quinazoline structure-containing compound having the structure shown in formula (1-2) is any one of the following compounds:
in the present invention, the hole transport compound has a hole conducting property.
Preferably, the hole transport compound is a compound having a structure represented by formula (2):
wherein p is selected from the group consisting of integers from 0 to 4,
q is selected from the group consisting of integers from 0 to 4,
R 7 、R 8 each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl wherein one or more methylene groups are substituted by-O-or-S-in such a way that O atoms or S atoms are not adjacent substituted or unsubstituted C2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a manner that O atoms or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkynyl substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy,
R 7 、R 8 each independently exists, or the adjacent two are connected by a chemical bond to form a ring B or R 7 、R 8 Connected with each other through a phenylene ring or a naphthylene ring;
L 2 、L 3 each independently selected fromA linkage, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene,
Ar 4 -Ar 7 each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
w1 is selected from the group consisting of integers from 0 to 1,
w2 is selected from the group consisting of integers from 0 to 1,
preferably, w1+ w2=1.
Preferably, the ring B is a substituted or unsubstituted group as follows: a benzene ring, a naphthalene ring, a benzothiophene ring, a benzofuran ring, an indene ring or an indole ring;
preferably, the hole transport compound is a compound having any one of the structures shown below:
preferably, R in formula (2) 7 、R 8 Are connected with adjacent ring substituents through phenylene to form a seven-membered fused ring,
preferably, the hole transporting compound is a compound having any one of the structures shown below (a compound having the seven-membered fused ring):
wherein q-2 is selected from 0, 1, 2.
Preferably, in the formula (2), L 2 、L 3 Each independently selected from the group consisting of a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuran-substituted phenylene group, a substituted or unsubstituted dimethylfluorenyl-substituted phenylene group, a substituted or unsubstituted dibenzothiophene-substituted phenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dimethylfluorenyl group;
preference is given toEarth, ar 4 -Ar 7 Each is independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophenyl, dinaphthothiophenyl;
R 7 、R 8 each independently selected from deuterium, halogen, cyano, substituted or unsubstituted groups as follows: methyl, ethyl, tert-butyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophenyl, or dinaphthothiophenyl.
Preferably, when the groups defined in formula (1-1), formula (1-2) and formula (2) in the present invention carry a substituent, each of the substituents is independently selected from deuterium, halogen, cyano, unsubstituted or R ' substituted C1-C6 alkyl, unsubstituted or R ' substituted C6-C12 aryl, unsubstituted or R ' substituted C2-C20 heteroaryl; r' is selected from deuterium, halogen, cyano, deuterium-substituted methyl and halogen-substituted methyl.
Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthyl-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl or spirobifluorenyl;
preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, or dibenzocarbazolyl;
preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl or adamantyl.
Preferably, the compound having the structure represented by formula (2) is any one of the following compounds:
preferably, the thermal decomposition temperature difference between the hole transport compound and the fused heterocyclic compound containing a quinazoline structure is less than 20 degrees centigrade (e.g. the thermal decomposition temperature difference is 18 degrees centigrade, 15 degrees centigrade, 13 degrees centigrade, 10 degrees centigrade, 8 degrees centigrade, 5 degrees centigrade, 3 degrees centigrade, etc.), or the LUMO energy level of the fused heterocyclic compound containing a quinazoline structure is deeper than-2.0 eV (e.g. can be-2.5 eV, -2.8eV, -3.0eV, -3.5eV, -4.0eV, etc.), and the HOMO energy level of the hole transport compound is shallower than-5.8 eV (e.g. -5.5eV, -5.0eV, -4.8eV, -4.5eV, -4eV, -3eV, etc.).
Preferably, the mass ratio of the fused heterocyclic compound containing a quinazoline structure to the hole-transporting compound is 1.
Preferably, the mass ratio of the fused heterocyclic compound containing a quinazoline structure to the hole transport type compound in the organic electroluminescent composition is 1.
Preferably, the mass ratio of the fused heterocyclic compound containing a quinazoline structure to the hole transport type compound in the organic electroluminescent composition is 2.
As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine, preferably fluorine.
As used herein, the term "alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.
As used herein, unless otherwise specified, the term "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 30 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane and the like.
Heteroaryl, heteroarylene groups of the invention include monocyclic, polycyclic or fused ring aryl groups, which rings may be interrupted by short non-aromatic units, including, but not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenazinyl, phenothiazinyl, phenanthrolinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof, and the like.
Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl or spirobifluorenyl.
Preferably, the heteroaryl group is selected from dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthoimidazolyl, naphthooxazolyl, naphthothiazolyl, phenanthroimidazolyl, phenanthrooxazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidyl, benzofuropyrazinyl, benzofuropyrimidinyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl, indenopyrimidinyl, spiro (fluorene-9, 1 '-indene) pyrazinyl, spiro (fluorene-9, 1' -indene) pyrimidinyl, benzofurocarbazolyl, or benzothiophenocarbazolyl.
As used herein, the term "aryloxy" refers to a monovalent substituent represented by RO-, wherein R represents an aryl group having 6 to 30 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
As used herein, the term "substituted" means that the hydrogen atom in the compound is replaced with another substituent. The position is not limited to a specific position as long as hydrogen at the position can be substituted by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.
The phrase "two adjacent groups are linked to form a ring" as used herein means that 2 substituents at adjacent positions on the same or adjacent rings can pass throughChemical bonds are connected with each other to form a ring, and the invention does not limit the specific connecting ring mode (for example, by single bond connection, etc.)
Thickening and passing
Thickening and passing
Thickening and passing
Thickening and passing
Thickening; wherein
Indicating a thick and dense position) has the same meaning as when the same description is referred to below.
In the present invention, the definition of a group defines a range of carbon numbers, the number of carbon atoms of which is any integer within the defined range, such as a C6-C60 aryl group, and the number of carbon atoms representing an aryl group can be any integer within the range encompassed by 6-60, such as 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55, 60, or the like.
In the invention, the preparation route of the compound containing the quinazoline structure is as follows:
the general formula of the synthesis of the compound with the structure shown in the formula (1-1)
When L is selected from the link, the third step takes the route of (2);
the general formula of the synthesis of the compound with the structure shown in the formula (1-2)
When L is selected from the group consisting of the linkages, the second step follows the path of (2).
The preparation route of the hole transport type compound in the present invention is as follows:
in another aspect, the present invention provides the use of an organic electroluminescent composition as described above for the manufacture of an optical device.
Preferably, the optical device comprises any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light emitting electrochemical cell, an organic laser diode or an organic photoreceptor.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the organic electroluminescent composition as described above.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are stacked in this order from the anode side to the cathode side.
Preferably, the material of the light-emitting layer comprises a host material and a guest material, the host material comprising the organic electroluminescent composition as described above; the thermal decomposition temperature difference between the fused heterocyclic compound containing the quinazoline structure and the hole transport type compound is not more than 20 ℃, preferably 10 ℃, and further preferably 5 ℃;
preferably, the guest material comprises a phosphorescent dopant comprising a complex comprising Ir or Pt.
In another aspect, the present invention provides an organic electroluminescent device comprising the organic electroluminescent device as described above.
Compared with the prior art, the invention has the following beneficial effects:
compared with a single-component luminescent main body material, the organic electroluminescent composition has stronger combination of electrons and holes, and is more beneficial to improving the luminescent efficiency and prolonging the service life of a device. The organic electroluminescent device has lower driving voltage (below 3.55V), higher current efficiency (above 24 Cd/A) and longer service life (above 433 h).
Detailed Description
The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthetic examples
1-B Synthesis, 50ml of two-neck round-bottom flask is taken and put into a stirrer and an upper reflux pipe, nitrogen is filled after drying, 1-A (1 mmol), bis (pinacolato) diboron (1.2 mmol), potassium acetate (2 mmol), 1, 4-dioxane (20 ml) are respectively added, nitrogen protection is carried out, 1-bis (diphenylphosphino) ferrocene ] palladium (II) dichloride (0.05 mmol) is added, reflux is carried out for 12 hours, and after the reaction is finished, the crude product is purified by column chromatography (ethyl acetate/n-hexane: volume ratio is 1/10) to obtain 1-B (0.11 g, yield is 47%).
Synthesis of 1-D: taking a 50ml double-neck round-bottom flask, putting a stirrer and an upper connecting reflux pipe, introducing nitrogen after drying, and respectively adding a compound 1-C (1 mmol), a compound 1-B (1 mmol) and potassium carbonate (K) 2 CO 3 1.5mmol, ethanol (3 ml), water (3 ml), toluene (15 ml) and tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.05 mmol), heating to 60 ℃ and reacting for 12 hours, cooling to room temperature after the reaction is finished, adding 20 ml of water for quenching, extracting with dichloromethane (3X 20 ml), adding magnesium sulfate to the obtained extract in sequence for drying, filtering and spin-drying, and obtaining crude extractThe product was purified by chromatography (ethyl acetate/n-hexane: 1/10 by volume) to give 1-D (0.15 g, 43% yield).
Synthesis of 1-F: a100-milliliter two-neck round-bottom flask is taken and placed with a stirrer and an upper reflux pipe, nitrogen is filled after drying, 1-D (1 mmol), carbazole (1 mmol), cesium carbonate (0.012 mol), tris (dibenzylideneacetone) dipalladium (Pd 2 (dba) 3, 0.05mmol) and 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (xphos, 0.055 mmol) are respectively added, then toluene is added, the mixture is refluxed for 24 hours, the reaction system is cooled to room temperature after reaction, the reaction system is filtered and concentrated, and the crude product is purified by chromatography (dichloromethane/n-hexane, 1/10 (volume ratio)) to obtain 1-F (0.38 g, 79% of yield).
Synthesis of Compound 1: taking a 50ml double-neck round-bottom flask, putting a stirrer and an upper reflux pipe, introducing nitrogen after drying, and respectively adding 1-F (1 mmol) and dichlorobis (tricyclohexylphosphine) palladium (PdCl) 2 (PCy 3 ) 2 0.05 mmol), pivalic acid (t-BuCO) 2 H,2 mmol), cesium carbonate (Cs) 2 CO 3 2 mmol) and dimethylacetamide (20 ml) at 120 ℃ for 10 hours, after completion of the reaction, cooled to room temperature, the reaction was concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane: volume ratio 1/10), yielding 1 (0.27 g, 61% yield).
Elemental analysis: c 32 H 19 N 3 Theoretical value: c,86.27; h,4.30; n,9.43; measured value: c,86.32; h,4.28; n,9.40; HRMS (ESI) M/z (M +): theoretical values are as follows: 445.1579; measured value: 445.1584.
2-F Synthesis: the synthesis of 1-F was identical except that 2-C was used instead of carbazole to give 2-F (0.47 g, 77% yield).
Synthesis of Compound 2: synthesis of Compound 1 except substituting 2-F for 1-F gave Compound 2 (0.38 g, 67% yield).
Elemental analysis: c 42 H 23 N 3 Theoretical values are as follows: and C,88.55; h,4.07; n,7.38; measured value: c,88.59; h,4.05; n,7.36; HRMS (ESI) M/z (M +): theoretical values are as follows: 569.1892; measured value: 569.1898.
synthesis of 5-F: the synthesis of 1-F was identical except that 5-C was used instead of carbazole to give 5-F (0.49 g, 71% yield).
Synthesis of Compound 5: synthesis of Compound 1, except that 1-F was replaced with 5-F, gave Compound 5 (0.46 g, 70% yield).
Elemental analysis: c 48 H 28 N 4 Theoretical value: c,87.25; h,4.27; n,8.48; measured value: c,87.30; h,4.25; n,8.45; HRMS (ESI) M/z (M +): theoretical value: 660.2314; measured value: 660.2319.
synthesis of 7-F: the same synthesis as 1-D except that 1-D was used instead of 1-C, and 7-C was used instead of 1-B gave 7-F (0.42 g, 67% yield).
Synthesis of compound 7: synthesis of Compound 1 except substituting 7-F for 1-F gave Compound 7 (0.45 g, 76% yield).
Elemental analysis: c 44 H 27 N 3 Theoretical values are as follows: c,88.42; h,4.55; n,7.03; measured value: c,88.38; h,4.57; n,7.05; HRMS (ESI) M/z (M +): theoretical values are as follows: 597.2205; measured value: 597.2213.
synthesis of 8-C: the same as 1-D except that 8-A was used instead of 1-C, and 8-B was used instead of 1-B, gave 8-C (0.12 g, 35% yield).
Synthesis of 8-D: the synthesis of 1-D was identical except that 1-C was replaced with 8-C and 1-B was replaced with o-chlorophenylboronic acid to give 8-D (0.18 g, 48% yield).
Synthesis of 8-E: the same synthesis as 1-D except that 1-C was replaced with 8-D and 1-B was replaced with phenylboronic acid gave 8-E (0.24 g, 58% yield).
Synthesis of 8-F: synthesis of Compound 1, except that 1-F was replaced with 8-E, yielded 8-F (0.30 g, 77% yield).
Synthesis of 8-G: in a 50ml three-necked bottle, 8-F (1 mmol), dichloromethane (20 ml) and a solution of boron tribromide (2 mmol) in dichloromethane are added dropwise at 0 ℃, after the reaction is completed, the solvent is removed, and the crude product is purified by column chromatography (ethyl acetate/n-hexane, 1/10) to obtain 8-G (0.33G, 88% yield).
Synthesis of 8-H: taking a 50ml two-neck round-bottom flask, putting a stirrer, adding 8-G (1 mmol), dichloromethane (20 ml) and pyridine (6 mmol), cooling a reaction system to 0 ℃, and adding Tf 2 O (1.5 mmol), stirring at room temperature for 30 minutes, cooling to 0 ℃, adding 30 ml dichloromethane, 40 ml water, drying the organic phase over anhydrous magnesium sulfate, distilling under reduced pressure to remove the solvent, and isolating the crude product by column chromatography (ethyl acetate/n-hexane, 1/10) to obtain 8-H (0.45 g, 90% yield).
Synthesis of 8-J: taking a 50ml round-bottom double-neck bottle, putting a stirrer and an upper reflux pipe, adding the double pinacolyl diboron (1.5 mmol), the potassium acetate (2 mmol), protecting with nitrogen, and adding Pd (dppf) Cl 2 (0.05 mmol) and 8-H (1 mmol) are heated to 80 ℃ to react for 2 hours, water is added after the reaction is finished to quench, the system is extracted by ethyl acetate, an organic phase is dried by anhydrous magnesium sulfate to remove an organic solvent, and a crude product is separated by column chromatography (ethyl acetate/n-hexane, 1/10) to obtain 8-J (0.43 g, 89 percent of yield).
Synthesis of compound 8: taking a 50ml double-neck round-bottom flask, putting a stirrer and an upper connecting reflux pipe, introducing nitrogen after drying, and respectively adding a compound 8-J (1 mmol), a compound 8-K (1 mmol) and potassium carbonate (K) 2 CO 3 1.5mmol, ethanol (3 ml), water (3 ml), toluene (15 ml) and tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.05 mmol), heated to 60 ℃ and reacted for 12 hours, cooled to room temperature after completion of the reaction, quenched by addition of 20 ml of water, extracted with dichloromethane (3 × 20 ml), the resulting extract dried over magnesium sulfate, filtered and spun, and the crude product purified by chromatography (ethyl acetate/n-hexane: volume ratio 1/10), yield 8 (0.48 g, 86% yield).
Elemental analysis: c 40 H 24 N 4 Theoretical value: c,85.69; h,4.31; n,9.99; measured value: c,85.73; h,4.30; n,9.97; HRMS (ESI) M/z (M +): theoretical value: 560.2001; measured value: 560.2009.
synthesis of compound 9: the same synthesis as 8, except that 8-K was replaced with 9-K gave 9 (0.60 g, 85% yield).
Elemental analysis: c 50 H 33 N 5 Theoretical value: c,85.32; h,4.73; n,9.95; measured value: c,85.27; h,4.75; n,9.98; HRMS (ESI) M/z (M +): theoretical value: 703.2736; measured value: 703.2742.
synthesis of 12-F: the same synthesis as 1-D except that 1-D was used instead of 1-C,12-C was used instead of 1-B gave 12-F (0.56 g, 72% yield).
Synthesis of compound 12: synthesis of Compound 1 except substituting 12-F for 1-F gave Compound 12 (0.58 g, 79% yield). Elemental analysis: c 53 H 33 N 5 Theoretical values are as follows: c,86.04; h,4.50; n,9.47; measured value: c,85.98; h,4.52; n,9.50; HRMS (ESI) M/z (M +): theoretical values are as follows: 739.2736; measured value: 739.2744.
synthesis of 1' -C: the synthesis of 1-D was identical except that 1' -A was used instead of 1-C,1' -B was used instead of 1-B to give 1' -C (0.13 g, 40% yield).
Synthesis of 1' -E: the same synthesis as 1-F, except that 1' -C was used instead of 1-D and 1' -D was used instead of carbazole, gave 1' -E (0.55 g, 78% yield).
Synthesis of compound 1': synthesis of Compound 1, except that 1'-E was used instead of 1-F, gave Compound 1' (0.53 g, 81% yield). Elemental analysis: c 48 H 28 N 4 Theoretical value: c,87.25; h,4.27; n,8.48; measured value: c,87.30; h,4.25; n,8.45; HRMS (ESI) M/z (M +): theoretical value: 660.2314; measured value: 660.2309.
synthesis of 2' -E: the same synthesis as 1-F, except that 1' -C was used instead of 1-D and 2' -D was used instead of carbazole, gave 2' -E (0.53 g, 76% yield).
Synthesis of compound 2': compound 2 '(0.53 g, 80% yield) was obtained by substituting 2' -E for 1-F, which is a difference in the synthesis of Compound 1. Elemental analysis: c 48 H 28 N 4 Theoretical value: c,87.25; h,4.27; n,8.48; measured value: c,87.29; h,4.26; n,8.45; HRMS (ESI) M/z (M +): theoretical values are as follows: 660.2314; measured value: 660.2305.
synthesis of 3' -E: the synthesis of 1-F was identical except that 1' -C was used instead of 1-D and 3' -D was used instead of carbazole to give 3' -E (0.47 g, 77% yield).
Synthesis of compound 3': the synthesis of compound 1 was performed with the difference that 1-F was replaced with 3'-E to give compound 3' (0.47 g,yield 82%). Elemental analysis: c 40 H 21 N 3 S theoretical value: c,83.45; h,3.68; n,7.30; s,5.57; measured value: c,83.40; h,3.69; n,7.32; s,5.59; HRMS (ESI) M/z (M +): theoretical values are as follows: 575.1456; measured value: 575.1464.
synthesis of 4' -E: the same synthesis as 1-F, except that 1' -C was used instead of 1-D and 4' -D was used instead of carbazole, gave 4' -E (0.45 g, 78% yield).
Synthesis of compound 4': synthesis of Compound 1, except that 1-F was replaced with 4'-E, gave Compound 4' (0.44 g, 81% yield). Elemental analysis: c 40 H 21 N 3 Theoretical value: c,88.38; h,3.89; n,7.73; measured value: c,88.42; h,3.88; n,7.70; HRMS (ESI) M/z (M +): theoretical values are as follows: 543.1735; measured value: 543.1730.
synthesis of 5' -E: the same synthesis as 1-F, except that 1' -C was used instead of 1-D and 5' -D was used instead of carbazole, gave 5' -E (0.47 g, 76% yield).
Synthesis of compound 5': compound 5 '(0.47 g, 80% yield) was obtained by substituting 5' -E for 1-F, which is a difference in the synthesis of Compound 1. Elemental analysis: c 42 H 26 N 4 Theoretical value: c,85.98; h,4.47; n,9.55; measured value: c,86.03; h,4.45; n,9.52; HRMS (ESI) M/z (M +): theoretical values are as follows: 586.2157; measured value: 586.2165.
synthesis of 6' -D: the same synthesis as 1-D except that 1' -C was used instead of 1-C,6' -D instead of 1-B gave 6' -E (0.43 g, 71% yield).
Synthesis of compound 6': compound 6 '(0.45 g, 80% yield) was obtained by substituting 6' -E for 1-F, which is a difference in the synthesis of Compound 1. Elemental analysis: c 40 H 24 N 4 Theoretical value: c,85.69; h,4.31; n,9.99; measured value: c,85.75; h,4.29; n,9.96; HRMS (ESI) M/z (M +): theoretical values are as follows: 560.2001; measured value: 560.2010.
in a 100 ml three-necked flask, nitrogen gas was introduced, and the compound H1-A (0.01 mol), the compound H1-B (0.01 mol), sodium tert-butoxide (0.02 mol), tris (dibenzylideneacetone) dipalladium (0) (0.2 mmol), a 50% tri-tert-butylphosphine solution (0.8 mmol) and 50ml of toluene were added, followed by stirring under reflux. After cooling to 25 ℃ with ethyl acetate and H 2 O extracts the organic layer. The extracted organic layer was over MgSO 4 Dried and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM/hexane) and then recrystallization purification using DCM/acetone mixed solvent, thereby obtaining compound H1 (0.43 g, yield 72%).
Elemental analysis: c 45 H 34 N 2 Theoretical value: c,89.67; h,5.69; n,4.65; measured value: c,89.70; h,5.67; n,4.63; HRMS (ESI) M/z (M +): theoretical value: 602.2722; measured value: 602.2713.
the same as H1, except that H2-A was used instead of H1-A and H2-B was used instead of H1-B, to give H2 (0.62 g, 88% yield)
Elemental analysis: c 52 H 32 N 2 Theoretical value of O: c,89.12; h,4.60; n,4.00; measured value: c,89.08; h,4.62; n,4.02; HRMS (ESI) M/z (M +): theoretical values are as follows: 700.2515; measured value: 700.2521.
good synthesis with H1, except substituting H3-A for H1-A and H3-B for H1-B, gave H3 (0.48 g, 86% yield)
Elemental analysis: c 42 H 28 N 2 Theoretical values are as follows: c,89.97; h,5.03; n,5.00; measured value: c,90.00; h,5.01; n,4.99; HRMS (ESI) M/z (M +): theoretical value: 560.2252; measured value: 560.2259.
the same as H1, except that H4-A was used instead of H1-A and H4-B was used instead of H1-B, to give H4 (0.57 g, 89% yield)
Elemental analysis: c 48 H 38 N 2 Theoretical value: c,89.68; h,5.96; n,4.36; measured value: c,89.72; h,5.94; n,4.34; HRMS (ESI) M/z (M +): theoretical value: 642.3035; measured value: 642.3042.
good synthesis with H1, except substituting H5-A for H1-A and H5-B for H1-B, gave H5 (0.61 g, 83% yield)
Elemental analysis: c 52 H 32 N 2 The theoretical value of OS: c,85.22; h,4.40; n,3.82; s,4.37; measured value: c,85.19; h,4.41; n,3.83; s,4.39; HRMS (ESI) M/z (M +): theoretical value: 732.2235; measured value: 732.2242.
good synthesis as H1 except substituting H6-A for H1-A and H6-B for H1-B gave H6 (0.37 g, 81% yield)
Element classificationAnd (3) analysis: c 34 H 24 N 2 Theoretical value: c,88.67; h,5.25; n,6.08; measured value: c,88.71; h,5.23; n,6.06; HRMS (ESI) M/z (M +): theoretical value: 460.1939; measured value: 460.1946.
the same as H1, except that H2-A was used instead of H1-A and H7-B was used instead of H1-B, to give H7 (0.53 g, 80% yield)
Elemental analysis: c 50 H 32 N 2 Theoretical value: c,90.88; h,4.88; n,4.24; measured value: c,90.91; h,4.86; n,4.23; HRMS (ESI) M/z (M +): theoretical values are as follows: 660.2565; measured value: 660.2574.
the same as H1, except that H8-A was used instead of H1-A, and H8-B was used instead of H1-B, to give H8 (0.57 g, 87% yield)
Elemental analysis: c 48 H 32 N 2 Theoretical value of O: c,88.32; h,4.94; n,4.29; measured value: c,88.29; h,4.95; n,4.31; HRMS (ESI) M/z (M +): theoretical value: 652.2515; measured value: 652.2523.
the same as H1, except that H6-A was used instead of H1-A and H9-B was used instead of H1-B, to give H9 (0.49 g, 85% yield)
Elemental analysis: c 43 H 32 N 2 Theoretical value: c,89.55; h,5.59; n,4.86; measured value: c,89.51; h,5.61; n,4.88; HRMS (ESI) M/z (M +): theoretical value: 576.2565; measured value: 576.2575.
good synthesis with H1, except substituting H10-A for H1-A and H10-B for H1-B, gave H10 (0.46 g, 85% yield)
Elemental analysis: c 40 H 28 N 2 Theoretical values are as follows: c,89.52; h,5.26; n,5.22; measured value: c,89.48; h,5.28; n,5.24; HRMS (ESI) M/z (M +): theoretical value: 536.2252; measured value: 536.2247.
good Synthesis with H1, except that H3-A was used instead of H1-A, and H11-B was used instead of H1-B, to give H11 (0.51 g, 86% yield)
Elemental analysis: c 44 H 30 N 2 Theoretical value: c,90.07; h,5.15; n,4.77; measured value: c,90.10; h,5.14; n,4.76; HRMS (ESI) M/z (M +): theoretical value: 586.2409; measured value: 586.2416.
device embodiment
The OLED has the following layer structure: a base ((ITO) coated glass substrate)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/emissive layer (EML)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL), and finally a cathode.
The materials used are specified in table 1, and the materials required to make an OLED are as follows.
The preparation of the organic electroluminescent device comprises the following steps:
(1) Substrate cleaning: carrying out ultrasonic treatment on the ITO-coated glass substrate in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are less than or equal to 10wt% of glycol solvent and less than or equal to 1wt% of triethanolamine), washing in deionized water, and carrying out ultrasonic treatment in the following steps of: ultrasonic degreasing is carried out in an ethanol mixed solvent (volume ratio is 1.
(2) Evaporating an organic light-emitting functional layer:
placing the glass substrate with the anode layer in a vacuum chamber, and vacuumizing to 1 × 10 -6 To 2X 10 -4 Pa, performing vacuum evaporation on the anode layer film to form a PD as a hole injection layer, wherein the evaporation thickness is 5nm;
a hole transport layer is evaporated on the hole injection layer, and the thickness of the evaporated film is 80nm;
the luminescent layer is vapor-plated on the hole transport layer, and the specific preparation method comprises the following steps: carrying out vacuum evaporation on a luminescent host material and a guest material in a co-evaporation manner, wherein the total thickness of the evaporation is 30nm;
a layer of electron transport layer is vacuum evaporated on the luminescent layer, and the preparation method comprises the following steps: carrying out vacuum evaporation on Bphen and LiQ in a co-evaporation mode, wherein the total film thickness of evaporation is 30nm;
vacuum evaporating an electron injection layer on the electron transmission layer, wherein the total film thickness of the evaporation is 1nm;
and evaporating Mg and Ag on the electron injection layer, wherein the total thickness of the evaporated film is 80nm.
The parameters of the layers in the device, their materials and thicknesses, etc., are shown in table 1.
TABLE 1
Testing the performance of the device:
the instrument comprises: the characteristics of the device such as current, voltage, brightness, luminescence spectrum and the like are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
and (3) testing conditions: the current density is 10mA/cm 2 Room temperature.
And (3) life test: the time (in hours) was recorded when the device brightness dropped to 95% of the original brightness.
The device performance test results are shown in table 2:
TABLE 2
As can be seen from Table 2, the organic electroluminescent device of the present invention has a low driving voltage (below 3.55V), a high current efficiency (above 24 Cd/A) and a long lifetime (above 433 h).
The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent composition and the application thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must be implemented by relying on the above examples. It should be understood by those skilled in the art that any modifications of the present invention, equivalent substitutions of the raw materials of the product of the present invention, and the addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An organic electroluminescent composition is characterized by comprising a fused heterocyclic compound containing a quinazoline structure and a hole transport type compound, wherein the fused heterocyclic compound containing the quinazoline structure is a compound with a structure shown as a formula (1-1) or a formula (1-2),
l is selected from a linkage, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C5-C30 heteroarylene,
ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C5-C60 heteroarylamine, substituted or unsubstituted C5-C60 arylheteroarylamine,
R 1 -R 3 each independently selected from hydrogenDeuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy,
R n1 -R n8 、R m1 -R m6 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy.
2. The organic electroluminescent composition according to claim 1, wherein Ar is selected from the group consisting of carbazole-based groups:
R 4 -R 11 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl wherein one or more methylene groups are substituted by-O-or-S-in such a way that O atoms or S atoms are not adjacent substituted or unsubstituted C2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a manner that O atoms or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkynyl substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxyA substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C5-C60 heteroarylamine group, a substituted or unsubstituted C5-C60 arylheteroarylamine group,
R 4 -R 11 each independently exists or the two adjacent are connected to form a ring A; and/or R 4 And R 11 Through a benzene ring or a naphthalene ring;
preferably, the ring a is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted benzindole ring, a substituted or unsubstituted naphthoindole ring;
preferably, R 4 -R 11 Any two adjacent of them are fused with benzene ring, and/or R 4 And R 11 Connected through benzene ring and naphthalene ring;
preferably, R 4 -R 11 Each is independently selected from the following substituted or unsubstituted groups: phenyl, carbazolyl, phenyl-substituted carbazolyl, biphenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzofuran-substituted carbazolyl, terphenyl-substituted carbazolyl;
preferably, R 4 -R 11 Either one of them is combined with
The connection is carried out by connecting the two parts,
L 1 selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 1 、Ar 2 each is independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, biphenyl-substituted carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl;
preferably, ar is selected from
W is selected from O, S, NL 2 Ar 3 、CR 16 R 17 ，
L 2 Selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 3 selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothienyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, diphenylfluorenyl-substituted phenyl, spirobifluorenyl,
R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 each independently selected from hydrogen, deuterium, phenyl and/or adjacent two are connected to form a benzene ring,
R 16 、R 17 each independently selected from methyl, phenyl, or R 16 、R 17 The bonding is carried out to form a fluorenyl group,
and/or R 4 And R 11 Through benzene ring or naphthalene ring;
more preferably, ar is selected from the group consisting of substituted or unsubstituted:
wherein the wavy line represents the attachment site of the group;
preferably, ar is selected from the group consisting of substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, quinazolinyl, 2-phenylphenanthrene [3,4-d ] oxazolyl, 2-phenylphenanthrene [3,4-d ] thiazolyl;
preferably, R n1 -R n8 、R m1 -R m6 Each independently selected from the group consisting of substituted or unsubstituted hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, 2-phenylphenanthrene [3,4-d ] phenyl]Oxazolyl, 2-phenylphenanthrene [3,4-d ]]A thiazolyl group;
preferably, L is selected from a linker, phenylene, biphenylene, naphthylene, dibenzofuranylene;
preferably, the substituents are each independently selected from deuterium, halogen, cyano, unsubstituted or R ' substituted C1-C6 alkyl, unsubstituted or R ' substituted C6-C12 aryl, unsubstituted or R ' substituted C2-C20 heteroaryl;
r' is selected from deuterium, halogen, cyano, deuterium-substituted methyl and halogen-substituted methyl;
preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthyl substituted phenyl, dimethylfluorenyl, diphenyl substituted fluorenyl, spirobifluorenyl,
preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzocarbazolyl, dibenzocarbazolyl,
preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, adamantyl;
preferably, the quinazoline structure-containing compound having the structure shown in the formula (1-1) is any one of the following compounds:
preferably, the quinazoline structure-containing compound having the structure shown in formula (1-2) is any one of the following compounds:
3. the organic electroluminescent composition according to any one of claims 1 to 3, wherein the hole transport compound is a compound having a structure represented by formula (2):
wherein p is selected from the group consisting of integers from 0 to 4,
q is selected from the group consisting of integers from 0 to 4,
R 7 、R 8 each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl wherein one or more methylene groups are substituted by-O-or-S-in such a manner that O atoms or S atoms are not adjacent substituted or unsubstituted C2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a manner that O atom or S atom is not adjacent, substituted or unsubstituted C2-C30 alkynyl substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy,
R 7 、R 8 each independently exists, or the two adjacent compounds are connected by chemical bonds to form a ring B or R 7 、R 8 Connected with each other through a phenylene ring or a naphthylene ring;
L 2 、L 3 each independently selected from the group consisting of a bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene,
Ar 4 -Ar 7 each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,
w1 is selected from the group consisting of integers from 0 to 1,
w2 is selected from the group consisting of integers from 0 to 1,
preferably, w1+ w2=1.
4. The organic electroluminescent composition according to any one of claims 1 to 3, wherein the ring B is a substituted or unsubstituted group selected from the group consisting of: a benzene ring, a naphthalene ring, a benzothiophene ring, a benzofuran ring, an indene ring or an indole ring;
preferably, the hole transport compound is a compound having any one of the structures shown below:
preferably, R in formula (2) 7 、R 8 Are connected with adjacent ring substituents through phenylene to form a seven-membered fused ring,
preferably, the hole transport compound is a compound having any one of the structures shown below (a compound having the seven-membered fused ring):
wherein q-2 is selected from 0, 1, 2;
preferably, in the formula (2), L 2 、L 3 Each independently selected from the group consisting of a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuran-substituted phenylene group, a substituted or unsubstituted dimethylfluorenyl-substituted phenylene group, a substituted or unsubstituted phenylene groupSubstituted dibenzothiophene substituted phenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dimethylfluorenyl;
preferably, ar 4 -Ar 7 Each is independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophenyl, dinaphthothiophenyl;
R 7 、R 8 each independently selected from deuterium, halogen, cyano, substituted or unsubstituted groups as follows: methyl, ethyl, tert-butyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothienyl or dinaphthothiophenyl;
preferably, when the groups defined in formula (1-1), formula (1-2) and formula (2) carry substituents, each of said substituents is independently selected from deuterium, halogen, cyano, unsubstituted or R ' substituted C1-C6 alkyl, unsubstituted or R ' substituted C6-C12 aryl, unsubstituted or R ' substituted C2-C20 heteroaryl; r' is selected from deuterium, halogen, cyano, deuterium-substituted methyl and halogen-substituted methyl;
preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthyl-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl or spirobifluorenyl;
preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzocarbazolyl, or dibenzocarbazolyl;
preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl or adamantyl.
5. The organic electroluminescent composition according to any one of claims 1 to 4, wherein the compound having the structure represented by formula (2) is any one of the following compounds:
6. the organic electroluminescent composition according to any one of claims 1 to 5, wherein the difference between the thermal decomposition temperatures of the hole-transporting compound and the fused heterocyclic compound containing the quinazoline structure is less than 20 ℃, or the LUMO energy level of the fused heterocyclic compound containing the quinazoline structure is deeper than-2.0 eV, and the HOMO energy level of the hole-transporting compound is shallower than-5.8 eV.
7. The organic electroluminescent composition according to any one of claims 1 to 6, wherein the mass ratio of the fused heterocyclic compound containing a quinazoline structure to the hole transport compound in the organic electroluminescent composition is 1.
8. Use of an organic electroluminescent composition according to any one of claims 1 to 7 for the preparation of an optical device;
preferably, the optical device comprises any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light emitting electrochemical cell, an organic laser diode or an organic photoreceptor.
9. An organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the organic electroluminescent composition according to any one of claims 1 to 7;
preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are stacked in this order from the anode side to the cathode side;
preferably, the material of the light-emitting layer comprises a host material and a guest material, the host material comprising the organic electroluminescent composition according to any one of claims 1 to 7; the thermal decomposition temperature difference between the fused heterocyclic compound containing the quinazoline structure and the hole transport type compound is not more than 20 ℃, preferably 10 ℃, and further preferably 5 ℃;
preferably, the guest material comprises a phosphorescent dopant comprising a complex comprising Ir or Pt.
10. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises the organic electroluminescent device as claimed in claim 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110875588.5A CN115700269A (en) | 2021-07-30 | 2021-07-30 | Organic electroluminescent composition and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110875588.5A CN115700269A (en) | 2021-07-30 | 2021-07-30 | Organic electroluminescent composition and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115700269A true CN115700269A (en) | 2023-02-07 |
Family
ID=85120810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110875588.5A Pending CN115700269A (en) | 2021-07-30 | 2021-07-30 | Organic electroluminescent composition and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115700269A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140026783A (en) * | 2012-08-23 | 2014-03-06 | 주식회사 두산 | Organic light-emitting compound and organic electroluminescent device using the same |
| CN107556310A (en) * | 2017-09-20 | 2018-01-09 | 石家庄诚志永华显示材料有限公司 | Imdazole derivatives, material and organic electroluminescence device comprising the imdazole derivatives |
| CN109232377A (en) * | 2018-09-30 | 2019-01-18 | 长春海谱润斯科技有限公司 | A kind of aromatic amino-derivative and its organic electroluminescence device |
| CN109456203A (en) * | 2018-11-03 | 2019-03-12 | 长春海谱润斯科技有限公司 | A kind of triarylamine derivative and its organic electroluminescence device |
| CN112939946A (en) * | 2019-12-10 | 2021-06-11 | 北京鼎材科技有限公司 | Compound and application thereof |
| CN113121364A (en) * | 2019-12-31 | 2021-07-16 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
-
2021
- 2021-07-30 CN CN202110875588.5A patent/CN115700269A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140026783A (en) * | 2012-08-23 | 2014-03-06 | 주식회사 두산 | Organic light-emitting compound and organic electroluminescent device using the same |
| CN107556310A (en) * | 2017-09-20 | 2018-01-09 | 石家庄诚志永华显示材料有限公司 | Imdazole derivatives, material and organic electroluminescence device comprising the imdazole derivatives |
| CN109232377A (en) * | 2018-09-30 | 2019-01-18 | 长春海谱润斯科技有限公司 | A kind of aromatic amino-derivative and its organic electroluminescence device |
| CN109456203A (en) * | 2018-11-03 | 2019-03-12 | 长春海谱润斯科技有限公司 | A kind of triarylamine derivative and its organic electroluminescence device |
| CN112939946A (en) * | 2019-12-10 | 2021-06-11 | 北京鼎材科技有限公司 | Compound and application thereof |
| CN113121364A (en) * | 2019-12-31 | 2021-07-16 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102613323B1 (en) | Heterocyclic compound and organic light emitting device comprising the same | |
| EP3683217A1 (en) | Heterocyclic compound and organic light emitting element comprising same | |
| EP4190779A1 (en) | Heterocyclic compound, organic light-emitting device comprising same, and composition for organic layer of organic light-emitting device | |
| KR20220047661A (en) | Nitrogen-containing compound, electronic device and electronic device comprising same | |
| TWI637953B (en) | Hetero-cyclic compound and organic light emitting device using the same | |
| KR102589217B1 (en) | Hetero-cyclic compound and organic light emitting device using the same | |
| EP4201931A1 (en) | Heterocyclic compound and organic light-emitting device comprising same | |
| JP2022532949A (en) | Nitrogen-containing compounds, electronic components and electronic devices | |
| JP2022504349A (en) | Organic electroluminescent compounds and organic electroluminescent devices containing them | |
| CN114773286B (en) | Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof | |
| JP2021158350A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| KR102143580B1 (en) | Organic light emitting device, manufacturing method of the same and composition for organic layer of organic light emitting device | |
| CN114805179A (en) | Nitrogen-containing compound, organic electroluminescent device, and electronic device | |
| CN116261347A (en) | Organic electroluminescent device | |
| CN113227084A (en) | Compound, composition, organic photoelectric device and display device | |
| JP2022517639A (en) | Organic electroluminescent compounds and organic electroluminescent devices containing them | |
| CN116143739A (en) | Diamine compound and organic light-emitting device thereof | |
| KR102559828B1 (en) | Compound and organic light emitting device using the same | |
| JP2022022206A (en) | Organic electroluminescent compound, plural host materials, and organic electroluminescent device using the same | |
| JP2023500759A (en) | Heterocyclic compound, organic light-emitting device containing the same, composition for organic layer of organic light-emitting device, and method for manufacturing organic light-emitting device | |
| CN115700269A (en) | Organic electroluminescent composition and application thereof | |
| KR102589223B1 (en) | Hetero-cyclic compound and organic light emitting device using the same | |
| JP2022519189A (en) | Compounds, organic optoelectronic devices and display devices | |
| CN115700247B (en) | Compound containing quinazoline structure and application thereof | |
| CN114497424B (en) | Organic electroluminescent device and electronic device including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |