CN114685539A - Organic compound, application thereof and organic electroluminescent device adopting organic compound - Google Patents
Organic compound, application thereof and organic electroluminescent device adopting organic compound Download PDFInfo
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- CN114685539A CN114685539A CN202011632753.6A CN202011632753A CN114685539A CN 114685539 A CN114685539 A CN 114685539A CN 202011632753 A CN202011632753 A CN 202011632753A CN 114685539 A CN114685539 A CN 114685539A
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- unsubstituted
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- independently selected
- aryl
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 239000000463 material Substances 0.000 claims abstract description 32
- -1 cyano, hydroxyl Chemical group 0.000 claims description 99
- 239000010410 layer Substances 0.000 claims description 96
- 125000001424 substituent group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 17
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 230000005669 field effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 4
- 238000001228 spectrum Methods 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract 2
- 230000005540 biological transmission Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 238000005086 pumping Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 150000001793 charged compounds Chemical class 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 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 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 238000003077 quantum chemistry computational method Methods 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
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- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine group Chemical group 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
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- NWKKGNZTDMMDSH-UHFFFAOYSA-N n,n-ditert-butylaniline Chemical compound CC(C)(C)N(C(C)(C)C)C1=CC=CC=C1 NWKKGNZTDMMDSH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
- H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention relates to an organic compound, a compound for an organic electroluminescent device and an organic electroluminescent device adopting the compound. The organic compound of the present invention has the following structure. The compound adopts a B-N resonance structure, is favorable for improving the luminous efficiency and narrowing the spectrum, and simultaneously, the HOMO and the LUMO of the molecule are alternately distributed on adjacent atoms, so that the molecule has certain TADF property, and is favorable for improving the luminous efficiency and prolonging the service life. When the compound of the present invention is used in an organic electroluminescent device,particularly, when the luminescent layer is made of a material, the carrier transmission balance in the device can be effectively improved, so that the device is ensured to obtain excellent effects of high luminous efficiency and low starting voltage.
Description
Technical Field
The present invention relates to organic compounds, and more particularly, to compounds for organic electroluminescent devices and organic electroluminescent devices using the same.
Background
At present, optoelectronic devices employing organic materials are becoming increasingly popular for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, and optoelectronic devices have potential cost advantages over inorganic devices. Organic Light Emission Diodes (OLED) are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, quick response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the technical field of novel display and novel illumination. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. In the organic electroluminescent device structure in the display and illumination field, blue fluorescence is generally used in combination with red and green phosphorescent materials. Recently, ultra-pure blue fluorescent dye B-N compounds based on TADF (Thermally Activated Delayed Fluorescence) have been reported in the literature, which are based on triphenylboron and contain two nitrogen atoms and form a rigid polycyclic aromatic skeleton. The nitrogen atom has an opposite resonance effect to that of the boron atom, and the opposite resonance effect is enhanced at the position of the para-position thereof. This effect therefore clearly separates the HOMO and LUMO orbitals, and the calculated molecular orbital of DABNA-1 indicates that the LUMO orbitals are distributed in the ortho and para positions relative to the boron atom and to the nitrogen atom and to the meta position relative to the boron atom. DABNA-1 emitted light at 459nm, a half-peak width of 28nm, CIE coordinates (0.13,0.09), and a maximum external quantum yield of 13.5%. The emission of DABNA-2 after the introduction of the substituent is 467nm, the half-peak width is 28nm, the CIE coordinate is (0.12,0.13), and the maximum external quantum yield is improved to 20.2%. However, the molecule emits light too blue, and the hole transport property is poor, which is not suitable for mass production.
B-N compounds, which are based on triphenylboron and contain two nitrogen atoms, form a rigid polycyclic aromatic skeleton. The nitrogen atom has an opposite resonance effect to that of the boron atom, and the opposite resonance effect is enhanced at the position para thereto. Therefore, this effect can separate HOMO and LUMO orbitals significantly, but since B — N forming compounds have emission spectra that are too blue and hole transport properties are poor, they are not suitable for mass production applications.
Disclosure of Invention
In order to solve the technical problems, the invention provides an organic compound, belongs to a thermal activation delayed fluorescence material, and simultaneously provides an application method of the compound on an OLED device and an organic electroluminescent device adopting the compound.
The structure of the organic compound of the invention is shown as a general formula (1):
in formula (1):
the ring A, the ring D, the ring E and the ring F are respectively and independently selected from one of substituted or unsubstituted C5-C30 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings, and the ring A and the ring D are not connected to form a ring;
when there are substituents on the above-mentioned ring a, ring D, ring E and ring F, the substituents are selected from one of halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1 to C20 chain alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 silyl, substituted or unsubstituted C6 to C60 arylamino, substituted or unsubstituted C3 to C60 heteroarylamino, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl, the substituents are independently connected to a connected aromatic ring or heteroaromatic ring to form a ring, and when there are a plurality of the substituents, any adjacent two of them may be connected to each other through a chemical bond to form a ring;
x is selected from O, S, NR1、CR2R3、SiR4R5One of (1);
the R is1～R5Each independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
The ring A, the ring D, the ring E and the ring F are respectively and independently selected from one of substituted or unsubstituted C5-C14 aromatic rings and substituted or unsubstituted C3-C14 heteroaromatic rings;
preferably, the ring A, the ring D, the ring E and the ring F are respectively and independently selected from one of substituted or unsubstituted C5-C8-membered aromatic rings and substituted or unsubstituted C5-C8 heteroaromatic rings;
when there are substituents on the above-mentioned ring a, ring D, ring E and ring F, the substituents are selected from one of halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1 to C20 chain alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 silyl, substituted or unsubstituted C6 to C60 arylamino, substituted or unsubstituted C3 to C60 heteroarylamino, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl, the substituents are independently connected to a connected aromatic ring or heteroaromatic ring to form a ring, and when there are a plurality of the substituents, any adjacent two of them may be connected to each other through a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
Further, the compound of the general formula of the present invention has a structure represented by formula (1-1):
in formula (1-1), ring A and ring D, X are each as defined in formula (1);
z is1～Z5Are each independently selected from CR6Or N, said R6Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is a substituent selected from the group consisting of hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl6Independently linked to the linking aromatic or heteroaromatic ring to form a ring or not, said R6When there are plural, any two adjacent ones of them may be linked to each other by a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
Still further, the compounds of the general formula of the present invention have the structure shown in formula (1-2):
in the formula (1-2), X is as defined in the formula (1), and Z1～Z5Is the same as defined in formula (1-1);
said Y is1～Y8Are each independently selected from CR7Or N, said R7Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is a substituent selected from the group consisting of hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl7Independently linked to the linking aromatic or heteroaromatic ring to form a ring or not, said R7When there are plural, any two adjacent ones of them may be linked to each other by a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
Further, in the formula (1), the formula (1-1) and the formula (1-2), X is preferably from O, S, NR1One of (1); more preferably, X is NR1。
Preferably, X is NR1Said R is1Is a structure represented by the following formula (4-1):
in the formula (4-1), Z21～Z25Are each independently selected from CR8Or N, said R8Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is a substituent selected from the group consisting of hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl8Independently linked to the linking aromatic or heteroaromatic ring to form a ring or not, said R8When there are plural, any two adjacent ones of them may be linked to each other by a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
More preferably, X is selected from NR1When said R is1Is a structure represented by the following formula (4-2):
in the formula (4-2), the Z21～Z24Are the same as defined in formula (4-1);
the R is selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy and substituted or unsubstituted C1-C20 silane; when a substituent exists on R, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
preferably, in the formula (4-2), R is selected from the following substituted or unsubstituted groups:
in the above-mentioned manner, the first and second substrates are,
represents the position of the access bond of the substituent group;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
Further, in the formulae (1-1) and (1-2), Z1～Z5Are each independently selected from CR6Or N, said R6Independently, one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl is preferable; more preferably, Z is1～Z5Are each independently selected from CR6Said R is6Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 naphthenic base and substituted or unsubstituted C5-C30 aryl. Preferably, Z is1～Z5Are each independently selected from CR6Said R is6Is hydrogen.
Further, in the formula (1-2), Y is1～Y8Are each independently selected from CR7Or N, said R7Independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl and substituted or unsubstituted C3-C30 heteroarylOne kind of (1); more preferably, Y1～Y8Are each independently selected from CR7Or N, said R7Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 naphthenic base and substituted or unsubstituted C5-C30 aryl.
Preferably, Y is1～Y8Are each independently selected from CR7Said R is7Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl.
Still further, in the formula (1-2), said Y1、Y4、Y5、Y8Are each independently selected from CR7Or N, said R7Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein Y is2、Y3、Y6、Y7Are each independently selected from CR17Said R is17Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl, wherein R is17Independently with the attached aromatic ring to form a ring or not;
preferably, said Y is2And Y7Independently selected from CR17Said R is17Independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl, and Y is3And Y6Independently selected from CH;
or, said Y3And Y6Independently selected from CR17Said R is17Independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl, and Y is2And Y7Independently selected from CH;
preferably, said Y is2、Y3、Y6、Y7Each independently selected from CH or one of the following substituent groups:
represents the position of the access bond of the substituent group;
still more preferably, said Y3And Y6Independently selected from CH, said Y2And Y7Independently selected from one of the following substituent groups:
or, said Y2And Y7Independently selected from CH, Y3And Y6Independently selected from one of the following substituent groups:
and represents the position of the bond of the substituent group.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the present specification, the expression of Ca to Cb represents that the group has a carbon number of a to b, and generally the carbon number does not include the carbon number of the substituent unless otherwise specified.
In the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present invention, the monocyclic aryl group means that one or at least two phenyl groups are contained in a molecule, and when the at least two phenyl groups are contained in a molecule, the phenyl groups are independent of each other and are connected by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
The hetero atom in the present invention generally refers to an atom or group of atoms selected from N, O, S, P, Si and Se, preferably N, O, S.
The atomic names given in this disclosure, including their respective isotopes, for example, hydrogen (H) includes1H (protium or H),2H (deuterium or D), etc.; carbon (C) is selected from12C、13C and the like.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, etc
In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and fused ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. The monocyclic aryl group means that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are located between the phenyl groupsIndependently of one another, by a single bond, as exemplified by: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. The fused ring aryl group means a group having at least two aromatic rings in a molecule, and the aromatic rings are not independent of each other but are fused to each other with two adjacent carbon atoms in common. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,
And mesitylene, and derivatives thereof. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl, 9-diamylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene and benzofluorenyl.
The heteroaryl group having C3 to C60 mentioned in the present invention includes monocyclic heteroaryl groups and fused heteroaryl groups, preferably heteroaryl groups having C3 to C30, more preferably heteroaryl groups having C4 to C20, and still more preferably heteroaryl groups having C5 to C12. The monocyclic heteroaryl group means that at least one heteroaryl group is contained in the molecule, and when one heteroaryl group and another group (for example, aryl group, heteroaryl group, alkyl group, etc.) are contained in the molecule, the heteroaryl group and the other group are independently connected by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl and the like. The fused ring heteroaryl group means a group which has at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in a molecule, and which are not independent of each other but share two adjacent atoms fused with each other. Examples of fused heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the aryl group. Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the heteroaryl group.
Examples of the aryloxy group in the present invention include monovalent groups composed of the above aryl group, heteroaryl group and oxygen.
Examples of the C6-C30 arylamino group in the present invention include: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino and the like.
Examples of the heteroarylamino group having C3 to C30 in the present invention include: pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.
The chain alkyl group mentioned in the present invention includes a straight chain alkyl group and a branched chain alkyl group unless otherwise specified. Specifically, the substituted or unsubstituted C1-C20 chain alkyl group is preferably a substituted or unsubstituted C1-C16 chain alkyl group. Examples of the substituted or unsubstituted C1-C10 chain alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl and the like.
In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single cyclic structure; polycyclic alkyl refers to a structure in which two or more cycloalkyl groups share one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and the like.
In the present specification, examples of the substituted or unsubstituted C1-C20 alkoxy group, preferably substituted or unsubstituted C1-C10 alkoxy group, and C1-C10 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
In the present specification, examples of the substituted or unsubstituted C1-C20 silyl group, the substituted or unsubstituted C1-C10 silyl group, and the C1-C10 silyl group include silyl groups substituted with the groups exemplified for the C1-C10 alkyl groups, and specific examples thereof include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and the like.
Preferred structures of the compounds according to the present invention include, but are not limited to, the following compounds:
as another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. In particular, the use as a material for a light-emitting layer in an organic electroluminescent device is preferred, and the use as a light-emitting dye and/or sensitizer in a light-emitting layer in an organic electroluminescent device is more preferred.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer contains the compound of formula (1) as described above or contains the compound having the structure represented by P1 to P139 as described above.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains the compound represented by the general formula (1), the formula (1-1) or the formula (1-2) or the compound having the structure of P1 to P139.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or the display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The specific reason why the above-mentioned compound of the present invention is excellent as a material for a light-emitting dye and/or a sensitizer in a light-emitting layer in an organic electroluminescent device is not clearly understood, and it is presumed that the following reasons are possible:
the naphthalene ring is introduced into the parent nucleus structure of the compound, so that the molecular rigidity is improved, and the improvement of the luminous efficiency and the narrowing of the spectrum are facilitated. The compound adopts a B-N resonance structure, so that HOMO and LUMO of molecules are alternately distributed on adjacent atoms, the molecules have certain TADF property, and the improvement of luminous efficiency and the prolonging of service life are facilitated.
It is noted that the possible actions of the various groups/features are described separately herein for ease of illustration, but that this does not mean that the groups/features act in isolation. In fact, the reason for obtaining good performance is essentially an optimized combination of the whole molecule, as a result of synergy between the individual groups, rather than the effect of a single group.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
However, it should be noted that the method and materials for obtaining the compound are not limited to the method and materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the novel compounds of the present invention. The compounds of the present invention, for which no synthetic method is mentioned, are commercially available starting products or are prepared by the starting products according to known methods.
Solvents and reagents used in the synthesis examples, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole and other chemical reagents, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bide pharmaceutical, Bailingwei reagents, and the like. In addition, they can be synthesized by a known method by those skilled in the art.
Analytical testing of synthetic examples intermediates and compounds an abciex mass spectrometer (4000QTRAP) was used.
The following provides a brief description of the synthesis of the compounds of the present invention
Synthesis examples.
Representative synthetic route:
more specifically, the following shows a method for synthesizing a representative compound of the present invention.
Synthetic examples
Synthesis example 1: synthesis of Compound P1
Synthesis of intermediate P1-1:
1, 8-dibromo-7-chloronaphthalene (50g, 156.05mmol), phenylboronic acid (19.03g, 156.05mmol), potassium carbonate (43.13g, 312.10mmol), tetrakistriphenylphosphine palladium (1.80g, 1.56mmol), dioxane 500ml, water 100ml, 110 ℃ were added to a 2L single-neck flask at room temperature for reaction overnight. Stopping heating, cooling to room temperature, filtering with 100-200 mesh silica gel, evaporating to remove solvent, and performing silica gel column chromatography (PE) to obtain 31.21g of white solid product. Mass spectrometric analysis determined molecular ion mass: 317.61 (theoretical value: 317.61).
Synthesis of intermediate P1-2:
at room temperature, P1-1(30g, 94.46mmol), diphenylamine (15.98g, 94.46mmol), Pd2(dba)3(4.32g, 4.72mmol), tri-tert-butylphosphine tetrafluoroborate (4.29g, 9.45mmol), sodium tert-butoxide (18.16g, 188.91mmol), xylene (600ml) were added to a 2L one-neck flask, and nitrogen was evacuated three times and heated to 130 ℃ for reaction overnight. The reaction solution is cooled to room temperature, filtered by 100-200 mesh silica gel, the filtrate is concentrated by mixing with silica gel, column chromatography (PE: DMC 10:1) is carried out to obtain 40g of crude product, and toluene/ethanol recrystallization is carried out to obtain 35g of white solid. Mass spectrometric analysis determined molecular ion mass: 405.92 (theoretical value: 405.93).
Synthesis of compound P1:
adding P1-2(30.00g, 73.91mmol) into a 1000ml three-necked bottle, adding o-xylene (300ml), pumping and charging nitrogen for three times, dropwise adding a coarse needle N-butyl lithium solution (147.81mmol) into the three-necked bottle under an ice water bath, stirring for 1 hour, pumping boron tribromide (55.54g, 221.72mmol) through a coarse needle under the ice water bath, adding the boron tribromide into the reaction solution, stirring for 30 minutes, heating to 45 ℃, stirring for 50 minutes, pumping N, N-diisopropylethylamine (28.66g, 221.72mmol) into the reaction system under the ice water bath, stirring for 30 minutes, heating to 120 ℃, and reacting overnight. The heating was stopped and after the system had cooled to room temperature, water (500ml) was added to quench. The organic phase was separated, the lower layer was taken, the aqueous phase was extracted three times with ethyl acetate (500ml), and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is mixed with silica gel, concentrated and subjected to column chromatography to obtain 13g of crude product, and the crude product is recrystallized by toluene/ethanol to obtain 7.14g of yellow solid. Mass spectrometric analysis determined molecular ion mass: 379.27 (theoretical value: 379.27).
Synthesis example 2: synthesis of Compound P4
Synthesis of intermediate P4-1:
1, 8-dibromo-7-chloronaphthalene (50g, 156.05mmol), 4-tert-butylbenzoic acid (27.78g, 156.05mmol), potassium carbonate (43.13g, 312.10mmol), tetrakistriphenylphosphine palladium (1.80g, 1.56mmol), dioxane 500ml, water 100ml, 110 ℃ were added to a 2L single-neck flask at room temperature and reacted overnight. Stopping heating, cooling to room temperature, filtering with 100-200 mesh silica gel, evaporating the solvent, and performing silica gel sample-mixing column chromatography (PE) to obtain 36.56g of white solid product. Mass spectrometric analysis determined molecular ion mass: 373.72 (theoretical value: 373.72).
Synthesis of intermediate P4-2:
at room temperature, P4-1(30g, 80.27mmol), di-tert-butylaniline (22.59g, 80.27mmol), Pd2(dba)3(3.68g, 4.01mmol), tri-tert-butylphosphine tetrafluoroborate (3.65g, 8.03mmol), sodium tert-butoxide (15.43g, 160.55mmol), xylene (600ml) were added to a 2L one-neck flask, nitrogen was purged three times, and the mixture was heated to 130 ℃ for reaction overnight. The reaction solution was cooled to room temperature, filtered through 100-mesh 200-mesh silica gel, the filtrate was concentrated with silica gel, column chromatography (PE: DMC 10:1) gave 44g of crude product, and toluene/ethanol recrystallization afforded 41.2g of white solid. Mass spectrometric determination of molecular ion mass: 574.25 (theoretical value: 574.25).
Synthesis of compound P4:
adding P4-2(30.00g, 52.24mmol) into a 1000ml three-necked bottle, adding o-xylene (300ml), pumping and charging nitrogen for three times, dropwise adding an N-butyllithium solution (104.48mmol) with a coarse needle into the three-necked bottle under an ice-water bath, stirring for 1 hour, pumping boron tribromide (39.26g, 156.73mmol) with the coarse needle under the ice-water bath, adding into the reaction solution, stirring for 30 minutes, heating to 45 ℃, stirring for 50 minutes, pumping N, N-diisopropylethylamine (20.26g, 156.73mmol) into the reaction system under the ice-water bath, stirring for 30 minutes, heating to 120 ℃, and reacting overnight. The heating was stopped and after the system had cooled to room temperature, water (500ml) was added to quench. The organic phase was separated, the lower organic phase was extracted three times with ethyl acetate (500ml), and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is mixed with silica gel, concentrated and subjected to column chromatography to obtain 16g of crude product, and the crude product is recrystallized by toluene/ethanol to obtain 8.12g of yellow solid. Mass spectrometric analysis determined molecular ion mass: 547.59 (theoretical value: 547.59).
Synthetic example 3: synthesis of Compound P49
Synthesis of intermediate P49-1:
at room temperature, P1-1(30g, 94.46mmol), naphthylaniline (20.71g, 94.46mmol), Pd2(dba)3(4.32g, 4.72mmol), tri-tert-butylphosphine tetrafluoroborate (4.29g, 9.45mmol), sodium tert-butoxide (18.16g, 188.91mmol), xylene (600ml) were added to a 2L one-neck flask, and nitrogen was evacuated three times and heated to 130 ℃ for reaction overnight. The reaction solution was cooled to room temperature, filtered through 100-mesh 200-mesh silica gel, the filtrate was concentrated with silica gel, column chromatography (PE: DMC 10:1) gave 45g of crude product, and toluene/ethanol recrystallization afforded 32.5g of white solid. Mass spectrometric analysis determined molecular ion mass: 460.00 (theoretical value: 455.99).
Synthesis of compound P49:
adding P49-1(30.00g, 65.79mmol) into a 1000ml three-necked bottle, adding o-xylene (300ml), pumping and charging nitrogen for three times, dropwise adding an N-butyllithium solution (131.58mmol) with a coarse needle into the three-necked bottle under an ice-water bath, stirring for 1 hour, pumping boron tribromide (49.45g, 197.37mmol) with the coarse needle under the ice-water bath, adding into the reaction solution, stirring for 30 minutes, heating to 45 ℃, stirring for 50 minutes, pumping N, N-diisopropylethylamine (25.51g, 197.37mmol) into the reaction system under the ice-water bath, stirring for 30 minutes, heating to 120 ℃, and reacting overnight. The heating was stopped and after the system had cooled to room temperature, water (500ml) was added to quench. The organic phase was separated, the lower organic phase was extracted three times with ethyl acetate (500ml), and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is mixed with silica gel, concentrated and subjected to column chromatography to obtain a crude product of 15, and the crude product is recrystallized by toluene/ethanol to obtain 6.08g of yellow solid. Mass spectrometric analysis determined molecular ion mass: 429.33 (theoretical value: 429.33).
Device embodiments
Detailed description of the preferred embodiments
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the material of the light-emitting layer can be different materials such as a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The host material of the light-emitting layer is selected from, but not limited to, one or more of the combinations of PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more of TDE1-TDE 37.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77 may also be used, but are not limited thereto.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-73 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds from ET-1 to ET-73 or one or more compounds from PH-1 to PH-46; mixtures of one or more compounds from ET-1 to ET-73 with one or more compounds from PH-1 to PH-46 may also be used, but are not limited thereto.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca，Yb，Mg。
Computational chemistry:
the invention adopts Gaussian03 to carry out quantum chemical calculation on the compounds, adopts a time-dependent density functional method to respectively carry out theoretical calculation on the compounds listed in the table 1, and the calculation result is shown in the table 1. Wherein comparative compound C2 has the following structural formula:
synthesis of comparative compound C2: for a specific method, reference is made to the synthesis method in patent document KR1020190078541A, and the description thereof is omitted here.
Table 1 shows the results of quantum chemical calculations for the compounds of the present invention and comparative examples.
Table 1:
the fluorescence emission wavelength of the material is related to the first singlet state energy level, and the higher the energy level, the shorter the fluorescence emission wavelength of the material, the more blue the emission. The phosphorescence emission wavelength of the material is related to the first triplet level, the higher the level, the shorter the phosphorescence emission wavelength of the material, and the bluer the emission. As can be seen from the calculation results in Table 1, the examples of the compound of the present invention have higher singlet state energy than the comparative compound C2, and the emission wavelength thereof can be expected to be shorter, and the compound is more suitable as a light emitting material of a blue OLED device. This is probably because the nitrogen atom of the compound of the present invention is located between the benzene ring and the naphthalene ring, and this special connection mode leads to such compound having higher first singlet state and first triplet state energy levels, thus emitting more blue light, and meeting the requirement of deep blue light OLED device more.
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum thermal evaporation on the anode layer film in sequence to obtain a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer, a 60nm compound HT-4 as a hole transport layer and a 5nm compound HT-14 as an electron blocking layer; a binary mixture of 20nm compounds BFH-4: P1(100:3, w/w) as a light emitting layer, 5nm ET-23 as a hole blocking layer, 25nm compounds ET-69: ET-57(50/50, w/w) as an electron transport layer, 1nm LiF as an electron injection layer, and 150nm metallic aluminum as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Device examples 2 to 18 and comparative examples 1 to 2 were prepared in the same manner as in device example 1 except that P1 in the light emitting layer was replaced with the compounds P17, P81, P4, P85, P86, P87, P88, P90, P89, P36, P139, P11, P125, P8, P16, P20, P9 of the present invention and the comparative compounds C1 and C2 of the prior art.
The structure of comparative compound C1 is as follows:
synthesis of comparative compound C1: for a specific method, reference is made to the synthesis method in patent document KR1020190078541A, and the description thereof is omitted here.
Method of testing the device (including equipment and test conditions):
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and external quantum efficiency of the organic electroluminescent devices prepared in the compounds and the comparative materials were measured at the same brightness using a digital source meter, a luminance meter and PR 650. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The voltage at time is the drive voltage.
The properties of the organic electroluminescent devices prepared in the above device examples and comparative examples are shown in table 2 below.
Table 2:
as can be seen from table 1, in the case that the material schemes and the preparation processes of other functional layers in the organic electroluminescent device structure are completely the same, compared with the comparative example, the B-N type organic material of the present invention used in the organic electroluminescent device has a rigid structure, and thus has higher light emitting efficiency, and thus shows higher external quantum efficiency in the OLED device.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. 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 (11)
1. An organic compound having a structure represented by the following formula (1):
in formula (1):
the ring A, the ring D, the ring E and the ring F are respectively and independently selected from one of substituted or unsubstituted C5-C30 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings, and the ring A and the ring D are not connected to form a ring;
when there are substituents on the above-mentioned ring a, ring D, ring E and ring F, the substituents are selected from one of halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1 to C20 chain alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 silyl, substituted or unsubstituted C6 to C60 arylamino, substituted or unsubstituted C3 to C60 heteroarylamino, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl, the substituents are independently connected to a connected aromatic ring or heteroaromatic ring to form a ring, and when there are a plurality of the substituents, any adjacent two of them may be connected to each other through a chemical bond to form a ring;
x is selected from O, S, NR1、CR2R3、SiR4R5One of (1);
the R is1～R5Each independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
2. The organic compound according to claim 1, wherein each of ring a, ring D, ring E, and ring F is independently selected from one of a substituted or unsubstituted C5-C14 aromatic ring, a substituted or unsubstituted C3-C14 heteroaromatic ring;
preferably, the ring A, the ring D, the ring E and the ring F are respectively and independently selected from one of substituted or unsubstituted C5-C8-membered aromatic rings and substituted or unsubstituted C5-C8 heteroaromatic rings;
when there are substituents on the above-mentioned ring a, ring D, ring E and ring F, the substituents are selected from one of halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1 to C20 chain alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 silyl, substituted or unsubstituted C6 to C60 arylamino, substituted or unsubstituted C3 to C60 heteroarylamino, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl, the substituents are independently connected to a connected aromatic ring or heteroaromatic ring to form a ring, and when there are a plurality of the substituents, any adjacent two of them may be connected to each other through a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
3. The organic compound according to claim 1 or 2, having a structure represented by the following formula (1-1):
in formula (1-1), ring A and ring D, X are each as defined in formula (1);
z is1～Z5Are each independently selected from CR6Or N, said R6Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is a substituent selected from the group consisting of hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl6Independently linked to the linking aromatic or heteroaromatic ring to form a ring or not, said R6When there are plural, any two of them may be linked to each other by a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
4. The organic compound according to claim 3, having a structure represented by the following formula (1-2):
in the formula (1-2), X is as defined in the formula (1), and Z1～Z5Is the same as defined in formula (1-1);
said Y is1～Y8Are each independently selected from CR7Or N, said R7Independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl and substituted or unsubstituted C6-C60One of arylamino, substituted or unsubstituted C3-C60 heteroaryl amino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is one of aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl7Independently linked to the linking aromatic or heteroaromatic ring to form a ring or not, said R7When there are plural, any two adjacent ones of them may be linked to each other by a chemical bond to form a ring;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
5. The organic compound of any one of claims 1-4, wherein X is selected from O, S, NR1One of (1);
preferably, X is NR1；
Preferably, R1Is a structure represented by the following formula (4-1):
in the formula (4-1), Z21～Z25Are each independently selected from CR8Or N, said R8Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is a substituent selected from the group consisting of hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl8Independently linked to the linking aromatic or heteroaromatic ring to form a ring or not, said R8When there are plural, any two adjacent ones of them may be linked to each other by a chemical bond to form a ring;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
preferably, R1Is a structure represented by the following formula (4-2):
in the formula (4-2), the Z21～Z24Are all as defined in formula (4-1);
the R is selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy and substituted or unsubstituted C1-C20 silane; when a substituent exists on R, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
preferably, in the formula (4-2), R is selected from the following substituted or unsubstituted groups:
one of (1);
represents the position of the access bond of the substituent group;
when the substituent exists in the groups, the substituent is selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
6. The organic compound according to claim 3 or 4, formula (1-1) or formula (1-2), wherein Z is1～Z5Are each independently selected from CR6Or N, said R6Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
preferably, Z is1～Z5Are each independently selected from CR6Said R is6Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl;
when the substituent exists in the groups, the substituent is selected from one or a combination of at least two of halogen, cyano-group, hydroxyl, nitro-group, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
preferably, Z is1～Z5Are each independently selected from CR6Said R is6Is hydrogen.
7. The organic compound according to claim 4, formula (1-2), wherein Y is1～Y8Are each independently selected from CR7Or N, said R7Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
preferably, Y is1～Y8Are each independently selected from CR7Or N, said R7Independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3EOne of C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl;
preferably, Y is1～Y8Are each independently selected from CR7Said R is7Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl;
when the substituent exists in the groups, the substituent is selected from one or the combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
8. The organic compound of claim 4, said Y1、Y4、Y5、Y8Are each independently selected from CR7Or N, said R7Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein Y is2、Y3、Y6、Y7Are each independently selected from CR17Said R is17Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl, wherein R is17Independently with the attached aromatic or heteroaromatic ring to form a ring or not;
preferably, said Y is2And Y7Independently selected from CR17Said R is17Independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl, and Y is3And Y6Independently selected from CH;
or, said Y3And Y6Independently selected from CR17Said R is17Independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl and substituted or unsubstituted C5-C30 aryl, and Y is2And Y7Independently selected from CH;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
preferably, said Y is2、Y3、Y6、Y7Each independently selected from CH or one of the following substituent groups:
represents the position of the access bond of the substituent group;
still more preferably, said Y3And Y6Independently selected from CH, said Y2And Y7Independently selected from one of the following substituent groups:
or, said Y2And Y7Independently selected from CH, said Y3And Y6Independently selected from one of the following substituent groups:
and represents the position of the bond of the substituent group.
9. The organic compound of claim 1, having the structure shown below:
10. use of a compound according to any one of claims 1 to 9 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
further, the compound is applied to be used as a luminescent layer material in an organic electroluminescent device, and is particularly used as luminescent dye of a luminescent layer.
11. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic functional layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound according to any one of claims 1 to 9;
preferably, the organic functional layer comprises a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light emitting layer is disposed between the hole transport layer and the electron transport layer, wherein the light emitting layer contains the compound according to any one of claims 1 to 9.
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