CN113493455A - Organic compound, electronic element, and electronic device - Google Patents
Organic compound, electronic element, and electronic device Download PDFInfo
- Publication number
- CN113493455A CN113493455A CN202110757597.4A CN202110757597A CN113493455A CN 113493455 A CN113493455 A CN 113493455A CN 202110757597 A CN202110757597 A CN 202110757597A CN 113493455 A CN113493455 A CN 113493455A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 81
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 33
- 125000000732 arylene group Chemical group 0.000 claims abstract description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 8
- 239000010410 layer Substances 0.000 claims description 93
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 35
- -1 cyano, methyl Chemical group 0.000 claims description 34
- 230000005525 hole transport Effects 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000002346 layers by function Substances 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
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- 125000005843 halogen group Chemical group 0.000 claims description 6
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 239000011368 organic material Substances 0.000 abstract description 2
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- 238000003786 synthesis reaction Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000376 reactant Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 238000002347 injection Methods 0.000 description 16
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000012043 crude product Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 5
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- 125000002950 monocyclic group Chemical group 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
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- 125000003107 substituted aryl group Chemical group 0.000 description 3
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- 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
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
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- 125000003373 pyrazinyl group Chemical group 0.000 description 2
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention belongs to the technical field of organic materials, and provides an organic compound, an electronic element and an electronic device, wherein the organic compound has a structure shown in a formula 1: wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms; ar (Ar)1And Ar2Each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms. The organic compound of the present invention can improve the performance of electronic components.
Description
Technical Field
The present disclosure relates to the field of organic materials, and more particularly, to an organic compound, an electronic component, and an electronic device.
Background
With the development of electronic technology and the advancement of material science, the application range of electronic elements for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components, such as organic electroluminescent devices or photoelectric conversion devices, generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic element is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the organic light emitting layer under the action of the electric field, holes on the anode side also move to the organic light emitting layer, the electrons and the holes are combined in the organic light emitting layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the organic light emitting layer emits light outwards.
CN108084195A discloses a dicarbazole fused cyclic compound used in an organic light emitting device, which is according to the publication, has the characteristics of low driving voltage and high light emitting efficiency when applied to an organic light emitting layer, but the compound is not suitable for a hole transport material.
Disclosure of Invention
The invention provides an organic compound, an electronic element and an electronic device, wherein the organic compound can improve the performance of the electronic element.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
in a first aspect, the present invention provides an organic compound having a structure represented by formula 1:
L、L1、L2the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, and C5-30 substituted or unsubstituted heteroaryl;
L、L1、L2、Ar1and Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, and a heteroaryl group having 5 to 15 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring.
Another aspect of the present invention is to provide an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound described in any one of the above.
Another aspect of the present invention is to provide an electronic device including the above electronic component.
The organic compound provided by the invention carries out condensation ring on the carbazole compound, so that the carbazole compound has a larger conjugated system in a molecule and stronger intramolecular electron transfer capability, has higher thermal stability, and reduces the possibility of agglomeration of the conventional carbazole compound in a solid phase. In addition, the invention fuses benzene rings on the same benzene ring of the carbazole group and combines N atoms of carbazole to form an aza-benzene part, three formed six-membered rings are fused with each other, thereby increasing the structural rigidity, improving the thermal stability of the derivative, reducing the molecular agglomeration, and the triarylamine group is connected with the fused ring structure, being beneficial to dispersing the charge of the material, reducing the coplanarity of molecules, enabling the formed organic compound to be easier to form a film, improving the glass transition temperature of the product, enabling the product not to be easy to crystallize, effectively enhancing the conductivity of the material, and being more beneficial to the generation and transmission of holes. The organic compound is used in an organic electroluminescent device, the service life and the luminous efficiency of an organic electroluminescent device are obviously improved, and the working voltage is reduced to a certain extent.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. an electron blocking layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
In a first aspect, the present application provides an organic compound having a structure represented by formula 1:
L、L1、L2the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 5-30 carbon atoms;
L、L1、L2、Ar1and Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, and a heteroaryl group having 5 to 15 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring.
In this application, the terms "optional" and "optionally" mean that the subsequently described event can, but need not, occur, and that the description includes instances where the event either occurs or does not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may but need not form a ring, including: a case where two adjacent substituents form a ring and a case where two adjacent substituents do not form a ring.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc) or not, and if having a substituent, the number of the substituent may be one or more. For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl group having one or more substituents Rc. Among them, the substituent, i.e., Rc, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, or the like. When two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.
In the present application, the description that "each … … is independently selected from" and "… … is independently" and "… … is independently selected from" is used interchangeably and should be understood broadly to mean that the particular items expressed between the same symbols do not affect each other in different groups or that the particular items expressed between the same symbols do not affect each other in the same groups. For example,' A "
Wherein each q is independently selected from 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a hetero atom such as B, N, O, S, P or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
and the like.
In the present application, substituted aryl groups may be aryl groups in which one or more than two hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, and the like. Specific examples of heteroaryl as a substituent include, but are not limited to, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof that contains at least one heteroatom, which may be at least one of B, O, N, P, Si and S, in the ring. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl is heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).
As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).
In the present application, a cycloalkyl group having 3 to 10 carbon atoms may be used as a substituent for the aryl group or the heteroaryl group, and specific examples thereof include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a linear alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms, and examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups, and the like.
In the present application, halogen may include fluorine, chlorine, bromine, iodine.
In the present application, the aryl group having 6 to 15 carbon atoms as a substituent may have 6 (for example, phenyl), 10 (for example, naphthalene), 12 (for example, biphenyl), 13 (for example, fluorenyl), 15 or the like carbon atoms.
In the present application, the carbon number of the heteroaryl group having 5 to 15 carbon atoms as a substituent may be 5 (for example, pyridyl group), 12 (for example, dibenzothienyl group, dibenzofuranyl group), or the like.
In the present application, the structure of formula 1 is understood to mean an arylamine group
The connecting bond L in (1) may be fused with the structure in the parentheses
Through any of the 11 sites shown.
In some embodiments, the organic compound has a structure selected from the group consisting of:
alternatively, L, L1、L2The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 20 carbon atoms. Specifically, L, L1、L2May each be independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Alternatively, L, L1、L2The same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group.
In one embodiment, L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiazyl groupA thienyl group. L is1、L2The same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.
Alternatively, L, L1And L2Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms.
Alternatively, L, L1、L2Each substituent in (1) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl.
In a preferred embodiment, L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 6 to 18 carbon atoms, which further improves the lifetime and external quantum efficiency of the device.
In one embodiment, L is selected from the group consisting of a single bond and the following groups:
alternatively, L is selected from the group consisting of a single bond and:
preferably, L is selected from the group consisting of:
in one embodiment, L1And L2Each independently selected from the group consisting of a single bond and:
alternatively, L1、L2Each independently selected from the group consisting of a single bond and:
in one embodiment, Ar1And Ar2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl.
Alternatively, Ar1And Ar2Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms; optionally, any two adjacent substituents form a 5-13 membered saturated or unsaturated ring.
Alternatively, Ar1And Ar2Wherein the substituents are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl; optionally, any two adjacent substituents form a fluorene ring, cyclohexane or cyclopentane.
Alternatively, Ar1And Ar2Each independently selected from substituted or unsubstituted groupsZ, an unsubstituted group Z selected from the group consisting of:
the substituted group Z has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, cyclohexyl and cyclopentyl; when the number of the substituents is more than 1, the substituents are the same or different, and optionally, any two adjacent substituents form a fluorene ring, cyclopentane, cyclohexane.
Alternatively, Ar1、Ar2Each independently selected from the group consisting of:
alternatively, Ar1、Ar2Each independently selected from the group consisting of:
optionally, the organic compound is selected from the group consisting of:
the method for synthesizing the organic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the method for preparing the organic compound of the present invention in combination with the synthesis examples. In other words, the synthetic examples section of the present application illustratively provides methods for the preparation of organic compounds, and the starting materials employed can be obtained commercially or by methods well known in the art. All organic compounds provided herein are accessible to those skilled in the art in light of the preparation of these exemplary syntheses, and all specific methods of preparing the organic compounds will not be described in detail herein, and should not be construed as limiting the application to those skilled in the art.
In a second aspect, the present application provides an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound described above.
Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
Optionally, the functional layer comprises a hole transport layer comprising an organic compound provided herein. The hole transport layer may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein and other materials. The hole transport layer may be one layer, or may be two or more layers.
According to one embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
The organic compound provided by the application can be applied to the hole transport layer 321 of the organic electroluminescent device to prolong the service life of the organic electroluminescent device, and has higher luminous efficiency and lower working voltage.
In the present application, the anode 100 includes an anode material, which is preferably a material having a large work function (work function) that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Optionally, an electron blocking layer 322 is disposed between the hole transport layer 321 and the organic light emitting layer 330, and the electron blocking layer 322 can effectively block the transport of electron carriers to the anode 100 direction, so as to protect the material of the hole transport layer 321, and the material of the electron blocking layer may be TCTA.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. In one embodiment, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
Alternatively, the host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in this application. For example, the host material may be CBP, α, β -ADN. The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application, for example, the guest material may be ir (mdq)2(acac)、Ir(dmpq)3、BD-1。
Alternatively, the electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of TPBi and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF/Al、Liq/Al、LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the material of the hole injection layer 310 may be selected from m-MTDATA, HAT-CN, 1T-NATA or 2T-NATA.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as alkali metal sulfide, alkali metal halide, Yb, or the like, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 may include LiQ or Yb.
Alternatively, as shown in fig. 1, the hole injection layer 310, the hole transport layer 321, the electron blocking layer 322, the organic light emitting layer 330, the electron transport layer 340, and the electron injection layer 350 constitute the functional layer 300.
In another embodiment, the electronic component is a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.
Alternatively, the functional layer 300 includes a hole transport layer 321, and the hole transport layer 321 includes the organic compound of the present application. The hole transport layer 321 may be made of an organic compound provided herein, or may be made of an organic compound provided herein and other materials.
Alternatively, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 321, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole transport layer includes the organic compound of the present application.
In a third aspect, the present application also provides an electronic device comprising the electronic component according to the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400 including the organic electroluminescent device described above. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
In another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500 including the above-described photoelectric conversion device. The second electronic device 500 may be a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.
The present application is further illustrated by the following examples.
Synthesis of intermediate IM-1-X
1. Synthesis of intermediate IM-1-1
In N2Under an atmosphere, the starting material SA-1-1(127g, 549.57mmol), 25% by weight sulfuric acid (127mL), and azido acid (23.65g, 549.57mmol) were added and stirred at 50 ℃ for 3 hours. After the reaction was completed, 60mL of a 20 wt% potassium carbonate aqueous solution was added for neutralization, and after washing with water, anhydrous MgSO was used4The organic layer solvent was dried and collected and purified by column chromatography to obtain intermediate IM-1-1-a (21.6g, yield 15.9%) and intermediate IM-1-1-b (17.6g, yield 13.1%), respectively.
2. Referring to the synthesis method of intermediate IM-1-1, intermediate IM-1-X shown in Table 1 below was synthesized, wherein SA-1-1 was replaced with starting material SA-1-X, and intermediate IM-1-X shown in Table 1 below was synthesized.
TABLE 1
Synthesis of intermediate IM-2-Y
1. Synthesis of intermediate IM-2-1
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding an intermediate IM-1-1-a (17.5g, 71.11mmol), a reactant SA-2-1(16.9g, 71.11mmol), tris (dibenzylideneacetone) dipalladium (0.65g), X-phos (0.68g), sodium tert-butoxide (10.2g) and toluene (144mL), heating to 105 ℃ and 110 ℃, stirring for reaction for 2h, and cooling to room temperature after the reaction is finished. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulfate, filtering to remove the solvent, and purification by recrystallization of the crude product using a dichloromethane/n-heptane system gave intermediate IM-2-1(18.0g, 71.0% yield).
2. Referring to the synthesis of intermediate IM-2-1, intermediate IM-2-Y shown in Table 2 below was synthesized, wherein intermediate IM-1-X (wherein IM-1-5 was purchased directly) was substituted for intermediate IM-1-1-a and reactant SA-2-Z was substituted for reactant SA-2-1, to synthesize intermediate IM-2-Y shown in Table 2 below.
TABLE 2
Synthesis of intermediate IM-3-Y
1. Synthesis of intermediate IM-3-1
A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15min, and then added with intermediate IM-2-1(17.8g,49.91mmol), palladium acetate (5.61g), tricyclohexylphosphonium fluoroborate (18.38g), cesium carbonate (65.05g) and N, N-dimethylacetamide (178 mL). Starting stirring, heating and refluxing for reaction for 2h, and cooling to room temperature after the reaction is finished. Extracting the reaction solution with chloroform, separating an organic phase, drying the organic phase with anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography to give intermediate IM-3-1(8.47g, yield 53.0%).
2. The intermediate IM-3-X shown in Table 3 below was synthesized by referring to the synthesis method of the intermediate IM-3-1, wherein the intermediate IM-2-X was substituted for the intermediate IM-2-1 to synthesize the intermediate IM-3-X shown in Table 3 below.
TABLE 3
Synthesis of IV, intermediate IM-4-X
1. Synthesis of intermediate IM-4-1
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, sequentially adding an intermediate IM-3-1(17.8g, 55.59mmol), pinacol diboron diboride (14.12g, 55.59mmol), potassium acetate (8.18g), x-Phos (0.53 g), tris (dibenzylideneacetone) dipalladium (0.51g) and 1, 4-dioxane (144mL), heating to 75-85 ℃, refluxing for reaction for 3h, and cooling to room temperature after the reaction is finished. The reaction solution was extracted, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was freed of the solvent under reduced pressure, and the crude product was purified by recrystallization from a toluene system and filtered to give intermediate IM-4-1(14.54g, 71.2%).
2. The intermediate IM-4-X shown in Table 4 below was synthesized by referring to the synthesis method of the intermediate IM-4-1, wherein the intermediate IM-3-X was substituted for the intermediate IM-3-1 to synthesize the intermediate IM-4-X shown in Table 4 below.
TABLE 4
Fifthly, synthesis of intermediate IM-5-Z
1. Synthesis of intermediate IM-5-1
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, and adding intermediate IM-4-1(14.30g, 38.94mmol), reactant SA-4-1(7.45g, 38.94mmol), palladium acetate (0.087g), potassium carbonate (8.06g), s-phos (0.32g), toluene (84mL), absolute ethanol (28mL) and deionized water (28 mL); stirring and heating are started, reflux reaction is carried out for 4 hours when the temperature rises to 70-80 ℃, and cooling to room temperature is carried out after the reaction is finished. Extraction, water washing, combined organic phases, drying over anhydrous magnesium sulfate, filtration to remove the solvent, and purification by recrystallization of the crude product using a dichloromethane/n-heptane system gave solid intermediate IM-5-1(9.45g, 69.0% yield).
2. IM-5-Z shown in Table 5 below was synthesized by referring to the synthesis method of IM-5-1, wherein IM-4-1 was replaced by the intermediate IM-4-X and the reactant SA-4-1 was replaced by the reactant SA-4-Y, and IM-5-Z shown in Table 5 below was synthesized.
TABLE 5
Synthesis of intermediate IM-6-X
1. Synthesis of intermediate IM-6-1
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, and adding a reactant SA-5-1(7.5g, 28.5mmol), a reactant SA-6-1(4.46g, 28.5mmol), tetrakis (triphenylphosphine) palladium (0.33g), potassium carbonate (5.90g), TBAB (0.18g), toluene (48mL), absolute ethanol (16mL) and deionized water (16 mL); stirring and heating are started, reflux reaction is carried out for 4 hours when the temperature rises to 70-80 ℃, and cooling to room temperature is carried out after the reaction is finished. Extraction, water washing, combined organic phases, drying over anhydrous magnesium sulfate, filtration to remove the solvent, and purification by recrystallization of the crude product using a dichloromethane/n-heptane system gave solid intermediate IM-6-1(5.13g, yield 61.0%).
2. Referring to the synthesis of intermediate IM-6-1, intermediate IM-6-X shown in Table 6 below was synthesized, wherein reactant SA-5-Y was substituted for reactant SA-5-1 and reactant SA-6-Z was substituted for reactant SA-6-1, to synthesize intermediate IM-6-X shown in Table 6 below.
TABLE 6
Synthesis of heptahydrate intermediate IM-7-Y
1. Synthesis of intermediate IM-7-1
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding an intermediate IM-3-1(9.3g, 29.05mmol), a reactant SA-7-1(4.92g, 29.05mmol), tris (dibenzylideneacetone) dipalladium (0.27g), X-phos (0.28g), sodium tert-butoxide (4.19g) and toluene (93mL), heating to 105-110 ℃, stirring for reaction for 1h, and cooling to room temperature after the reaction is finished. Extraction, water washing, combined organic phases, drying over anhydrous magnesium sulfate, filtration to remove the solvent, and purification by recrystallization of the crude product using a dichloromethane/n-heptane system gave solid intermediate IM-7-1(8.42g, yield 70.9%).
2. The intermediates IM-7-Z shown in Table 7 below were synthesized by referring to the synthesis method of the intermediate IM-7-1, wherein the intermediate IM-3-1 was replaced by the intermediate IM-3-X or IM-5-Z and the reactant SA-7-W was replaced by the reactant SA-7-1, to synthesize the intermediates IM-7-X shown in Table 7 below.
TABLE 7
Synthesis example 1
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding intermediate IM-7-1(7.5g, 18.36mmol), reactant SA-8-1(4.28g, 18.36mmol), tris (dibenzylideneacetone) dipalladium (0.17g), s-phos (0.22g), sodium tert-butoxide (2.65g) and toluene (64mL), heating to 105-phos (110 ℃, stirring for reaction for 2h, and cooling to room temperature after the reaction is finished. Extraction, water washing, combination of the organic phases, drying over anhydrous magnesium sulfate, filtration to remove the solvent, and purification by recrystallization of the crude product using a dichloromethane/n-heptane system gave compound 21 as a solid (6.90g, yield 6)7.0%), ms spectrum: 561.23[ M + H ] M/z]+。
Referring to the synthesis of compound 21, compound X was synthesized by substituting IM-7-1 for intermediate IM-7-Z and SA-8-1 for reactant SA-8-Y (or IM-6-X), and the main starting materials, the synthesized compounds, their yields and mass spectrum characterization results are shown in Table 8.
TABLE 8
Preparation and evaluation of organic electroluminescent device
Example 1
An organic electroluminescent device was prepared by the following procedure: cutting the substrate coated with ITO/Ag/ITO (5nm/100nm/5nm) electrode into 40mm × 40mm × 0.7mm, performing photolithography to obtain experimental substrate with cathode, anode and insulating layer patterns, and treating with ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
The HAT-CN compound was vacuum-deposited on the test substrate (anode) to a thickness of
A Hole Injection Layer (HIL); followed by vacuum evaporation of a compound 21 over the hole injection layer to a thickness of
A Hole Transport Layer (HTL).
A compound TCTA as an Electron Blocking Layer (EBL) is evaporated on the Hole Transport Layer (HTL) to a thickness of
A compound alpha, beta-ADN is used as a main body and BD-1 with the weight ratio of 2 percent is doped on the Electron Blocking Layer (EBL) by evaporation to form the thickness of
The organic light emitting layer (EML).
On the organic light emitting layer (EML), TPBi and LiQ were mixed at a weight ratio of 1:1 and evaporated to form an Electron Transport Layer (ETL) with a thickness of
Vapor plating on an Electron Transport Layer (ETL)
As an Electron Injection Layer (EIL), and then magnesium (Mg) and silver (Ag) were mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer as a cathode having a thickness of
A compound CP-1 is vapor-deposited as an organic capping layer (CPL) on the cathode to a thickness of
The evaporated device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.
Examples 2 to 21
In the above-described device structure, an organic electroluminescent device was produced in the same manner as in example 1, except that the compound shown in table 10 was used in place of the compound 21 in the Hole Transport Layer (HTL).
Comparative examples 1 to 4
In comparative examples 1 to 4, organic electroluminescent devices were fabricated in the same manner as in example 1, except that the compound a, the compound B, the compound C, and the compound D were each used as a material for a Hole Transport Layer (HTL) instead of the compound 21.
Wherein, HAT-CN, alpha, beta-AND, TCTA, LiQ, TPBi, CP-1, BD-1, compound A, compound B, compound C, compound D have the structural formulas shown in Table 9.
TABLE 9
The properties of the prepared organic electroluminescent device are shown in Table 10, wherein the voltage, efficiency and color coordinates are 10mA/cm at constant current density2The test is carried out, and the service life of the T95 device is 20mA/cm at constant current density2The test was performed.
Watch 10
Referring to the results of table 10, it was found that the organic electroluminescent devices obtained in examples 1 to 21 generally had long life and high luminous efficiency as compared with the organic electroluminescent devices of comparative examples 1 to 4 in the case where the color coordinate CIEy was around 0.051. Wherein, the external quantum efficiency of the organic electroluminescent devices of the embodiments 1 to 21 is improved by more than 7% compared with that of the comparative example; compared with the comparative example, the service life of the organic electroluminescent device T95 is prolonged by at least 14%. Meanwhile, the driving voltage is reduced by more than 0.2V. In short, the organic compound of the present invention is applied to a Hole Transport Layer (HTL) of an organic electroluminescent device, which significantly improves the lifetime and external quantum efficiency of the organic electroluminescent device and also reduces the operating voltage to a certain extent.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (14)
1. An organic compound having a structure represented by formula 1:
L、L1、L2the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 5-30 carbon atoms;
L、L1、L2、Ar1and Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an alkyl group having 1 to 1 carbon atom0 haloalkyl group, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 5 to 15 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring.
2. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of the following structures:
3. an organic compound according to claim 1, wherein L, L is represented by1、L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 20 carbon atoms;
preferably L, L1And L2Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms.
4. An organic compound according to claim 1, wherein L, L is represented by1、L2Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group;
preferably L, L1、L2Wherein the substituents are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methyl, ethyl, pentyl, and pentyl,Cyclohexyl, phenyl, naphthyl, pyridyl.
5. The organic compound of claim 1, wherein L is selected from the group consisting of a single bond and:
6. the organic compound of claim 1, wherein L is1And L2Each independently selected from the group consisting of a single bond and:
7. the organic compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms;
preferably, Ar1And Ar2Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms; optionally, any two adjacent substituents form a 5-13 membered saturated or unsaturated ring.
8. The organic compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranylDibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl;
preferably, Ar1And Ar2Wherein the substituents are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl; optionally, any two adjacent substituents form a fluorene ring, cyclohexane or cyclopentane.
9. The organic compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from a substituted or unsubstituted group Z selected from the group consisting of:
the substituted group Z has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, cyclohexyl and cyclopentyl; when the number of the substituents is more than 1, the substituents are the same or different, and optionally, any two adjacent substituents form a fluorene ring, cyclopentane, cyclohexane.
10. The organic compound of claim 1, wherein Ar is Ar1、Ar2Each independently selected from the group consisting of:
11. the organic compound of claim 1, wherein the organic compound is selected from the group consisting of:
12. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1 to 11;
preferably, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
13. The electronic component according to claim 12, wherein the functional layer comprises a hole transport layer containing the organic compound.
14. An electronic device, characterized by comprising the electronic component of claim 12 or 13.
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