CN117645609A - Organic compound, organic electroluminescent device and electronic device - Google Patents
Organic compound, organic electroluminescent device and electronic device Download PDFInfo
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- CN117645609A CN117645609A CN202310440255.9A CN202310440255A CN117645609A CN 117645609 A CN117645609 A CN 117645609A CN 202310440255 A CN202310440255 A CN 202310440255A CN 117645609 A CN117645609 A CN 117645609A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 38
- 230000005525 hole transport Effects 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 116
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 239000010410 layer Substances 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- -1 cyano, methyl Chemical group 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 19
- 239000002346 layers by function Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 37
- 150000001875 compounds Chemical class 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 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 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- ZMDPKLISXOYQIZ-UHFFFAOYSA-N COC1=CC2=C(C=C1B(O)O)C1=CC=CC=C1O2 Chemical compound COC1=CC2=C(C=C1B(O)O)C1=CC=CC=C1O2 ZMDPKLISXOYQIZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 238000013461 design Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 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
- 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent 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
- 239000001301 oxygen Substances 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 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
- 238000010183 spectrum analysis Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 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
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-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
Classifications
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
The application belongs to organic materialsThe technical field of materials provides an organic compound, and the structure of the organic compound is shown as a formula 1. The application also provides an organic electroluminescent device and an electronic device comprising the organic compound. The organic compound is used as a hole transport layer material, can effectively reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and prolong the service life of the organic electroluminescent device.
Description
Technical Field
The present disclosure relates to the field of organic materials, and in particular, to an organic compound, an organic electroluminescent device, and an electronic device.
Background
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, and a great number of organic electroluminescent materials with excellent properties have been developed. In general, the direction of the future organic electroluminescent devices is to develop white light devices and full-color display devices with high efficiency, long lifetime and low cost, but the industrialization process of the technology still faces a number of key problems. Therefore, the compound is designed and searched to be a stable and efficient compound which is used as a novel material of the organic electroluminescent device to overcome the defects of the organic electroluminescent device in the practical application process, and is an important point in the research work of the material of the organic electroluminescent device and a research trend in the future. Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of 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.
In general, the stability and the transmission efficiency of the hole transmission material are poor, and when the hole transmission material is used for an organic electroluminescent device, the hole electron transmission cannot be truly balanced, so that the luminous efficiency of the device is reduced, and the service life of the device is shortened.
At present, although a large number of organic electroluminescent materials with excellent properties have been developed, the technology still has a number of problems. Therefore, how to design new materials with better performance, so as to reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and prolong the service life of the organic electroluminescent device is a problem to be solved in the art.
Disclosure of Invention
The present application aims to overcome the defects in the prior art, and provides an organic compound, an organic electroluminescent device and an electronic device containing the same, which can improve luminous efficiency and prolong service life of the device.
To achieve the above object, the first aspect of the present application provides an organic compound having a structure represented by formula 1:
wherein one of the ring A and the ring B is selected from the structure shown in formula 2, the other is a benzene ring, and the formula 2 is represented by the formula 2 and the formula 1A mutually fused position;
x is selected from C (R) 1 R 2 ) O or S;
R 1 and R is 2 The same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms or deuterated alkyl with 1-10 carbon atoms;
R 3 and R is 4 The same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
L、L 1 and L 2 The same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, heteroaryl group with 12-20 carbon atoms, aryl group with 6-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms, halogenated aryl group with 6-20 carbon atoms, and carbon atomTrialkylsilyl group having 3 to 12 child groups, triarylsilyl group having 18 to 24 carbon atoms, haloalkyl group having 1 to 10 carbon atoms or deuterated alkyl group having 1 to 10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring.
A second aspect of the present application provides an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound of the first aspect of the present application.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
Through the technical scheme, the chemical structure of the organic compound comprises benzofluorene, furan, thiophene condensed oxaphenanthrene and triarylamine, in the oxaphenanthrene group, two methyl groups and oxygen can provide electrons for benzene rings through a conjugated/super conjugated effect, so that the group has high conjugated electron cloud density, and after the group is combined with triarylamine, the group has high hole mobility, so that when the material is used for a hole transport layer of an organic electroluminescent device, the luminous efficiency of the device can be improved. The oxaphenanthrene group has a relatively planar structure, and meanwhile, the asymmetry and steric hindrance of the oxaphenanthrene group are larger than those of a general planar conjugated group, so that the oxaphenanthrene group has relatively low crystallinity and good film forming property, and can effectively prolong the service life of the device when being applied to an electroluminescent organic light-emitting device.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
Fig. 1 is a schematic structural view of an 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.
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 electroluminescent layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.
Specific embodiments thereof have been shown by way of example in the drawings and will herein be described in more detail. These drawings and the written description are not intended to limit the scope of the inventive concepts in any way, but to illustrate the concepts of the present application to those skilled in the art by reference to specific embodiments.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
The first aspect of the present application provides an organic compound, wherein the structure of the organic compound is shown in formula 1:
wherein one of the ring A and the ring B is selected from the structure shown in formula 2, the other is a benzene ring, and the formula 2 is represented by the formula 2 and the formula 1A mutually fused position;
x is selected from C (R) 1 R 2 ) O or S;
R 1 and R is 2 The same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms or deuterated alkyl with 1-10 carbon atoms;
R 3 and R is 4 The same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
L、L 1 and L 2 The same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-20 carbon atoms, heteroaryl groups with 12-20 carbon atoms, aryl groups with 6-20 carbon atoms, deuterated aryl groups with 6-20 carbon atoms, halogenated aryl groups with 6-20 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, triarylsilyl groups with 18-24 carbon atoms, halogenated alkyl groups with 1-10 carbon atoms or deuterated alkyl groups with 1-10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, two adjacent substituents form a ring; by "is meant that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In this application, the descriptions used herein of the manner in which each … … is independently "and" … … is independently "and" … … is independently selected from "are interchangeable, and should be understood in a broad sense to mean that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other. For example, "Wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, non-positional connection means a single bond extending from a ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
As another example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one side benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formula (X '-1) -formula (X' -4).
An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means includes any of the possible linkages as shown in formula (Y-1) -formula (Y-7).
In the present application L, L 1 、L 2 、Ar 1 And Ar is a group 2 Refers to all carbon number. For example, if L 1 Selected from the group consisting of substituted arylene groups having 12 carbon atoms, then the arylene groups and all of the substituents thereon have 12 carbon atoms. For example: ar (Ar) 1 Is thatThe number of carbon atoms is 7; l (L) 1 Is->The number of carbon atoms is 12.
In the present application, "hetero" means that at least 1 heteroatom such as B, N, O, S, se, si or P is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.
In this application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, in this application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "1 to 10 carbon atoms" refers to alkyl groups that may contain 1,2, 3,4, 5, 6, 7, 8, 9, or 10 carbon atoms. Alternatively, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In this application cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. Cycloalkyl groups may have 3 to 10 carbon atoms, in this application, numerical ranges such as "3 to 10" refer to each integer in the given range; for example, "5 to 10 carbon atoms" means that 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms may be contained. Alternatively, specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and the like.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenylRadical, pentacenyl, benzo [9,10]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc. The "substituted or unsubstituted aryl" herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 25, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 20, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 18, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 15. For example, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 18, 20, 24, 25 or 30, although other numbers are possible and are not listed herein. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals, as well as unsubstituted aryl radicals.
As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, or the like.
It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, specific examples of aryl groups as substituents include, but are not limited to: phenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In this application, fluorenyl groups may be substituted and two substituents may combine with each other to form a spiro structure, specific examples include, but are not limited to, the following structures:
in the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof containing 1,2, 3,4, 5 or 6 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-aryl carbazolyl (such as N-phenyl carbazolyl) and N-heteroaryl carbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. The "substituted or unsubstituted heteroaryl" herein may contain 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3 to 27, in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12 to 24, and in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12 to 20. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18 or 20, although other numbers are possible and are not listed here.
In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like.
It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to: dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, and the like.
In the present application, halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, a deuterated aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with deuterium, and specific examples of deuterated aryl groups include, but are not limited to: pentadeuterated phenyl.
In the present application, a halogenated aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with halogen atoms, and specific examples of the halogenated aryl group include, but are not limited to: fluorophenyl and chlorophenyl.
In the present application, a haloalkyl group may be one in which one or more hydrogen atoms in an alkyl group are substituted with halogen atoms, and specific examples of haloalkyl groups include, but are not limited to: trifluoromethyl.
In the present application, terphenyl includes
In some embodiments of the present application, the organic compound has a structure represented by any one of formulas 3 to 6:
in other embodiments of the present application, the organic compound has a structure represented by any one of formulas a to Z' below:
in some embodiments of the present application, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.
Alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups with 5-12 carbon atoms, aryl groups with 6-12 carbon atoms, deuterated aryl groups with 6-12 carbon atoms or alkyl groups with 1-5 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a fluorene ring
Further alternatively, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
In some embodiments of the present application, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthrylSubstituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9' -spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted phenanthroline group.
Alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.
In some embodiments of the present application, ar 1 And Ar is a group 2 And are identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups V, wherein unsubstituted groups V are selected from the group consisting of:
the substituted group V has one or more than two substituents, the substituents in the substituted group V are respectively and independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl, phenyl, naphthyl or pentadeuterated phenyl, and when the number of the substituents on the group V is more than 1, the substituents are the same or different.
In some embodiments of the present application, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the group consisting of:
in some embodiments of the present application, L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
Alternatively, the substituents in L are the same or different and are each independently selected from deuterium, a halogen group, cyano and an alkyl group having 1 to 5 carbon atoms or phenyl group.
In other embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.
Alternatively, the substituents in L are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
Specifically, L is selected from a single bond or the group consisting of:
in some embodiments of the present application, L 1 And L 2 And are identical or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
Alternatively, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups having 5 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, deuterated aryl groups having 6 to 12 carbon atoms or alkyl groups having 1 to 5 carbon atoms.
In other embodiments of the present application, L 1 And L 2 And are identical or different and are each independently selected from a single bond, a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
the substituted group W has one or more than two substituents, the substituents in the substituted group W are respectively and independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl or phenyl, and when the number of the substituents on the group W is more than 1, the substituents are the same or different.
In some embodiments of the present application, L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.
Alternatively, L 1 And L 2 Substituents in the phases are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
Specifically, L 1 And L 2 Identical or different and are each independently selected from the group consisting of single bonds or the following groups:
in some embodiments of the present application,and->Identical or different and are each independently selected from the group consisting of: />
Alternatively, the process may be carried out in a single-stage,and->Identical or different and are each independently selected from the group consisting of:
in some embodiments of the present application, R 1 And R is 2 Are all methyl groups.
In some embodiments of the present application, R 3 And R is 4 The same or different are respectively and independently selected from methyl or phenyl.
Alternatively, the organic compound is selected from the group of compounds as shown in claim 10.
The synthetic method of the organic compound provided in the present application is not particularly limited, and a person skilled in the art can determine a suitable synthetic method from the preparation method provided in the organic compound in combination with the preparation example section of the present application. All organic compounds provided herein can be obtained by one skilled in the art from these exemplary preparation methods, and all specific preparation methods for preparing the organic compounds are not described in detail herein, and should not be construed as limiting the present application.
A second aspect of the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the organic compound of the first aspect of the present application.
For example, as shown in fig. 1, the organic electroluminescent 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 contains an organic compound provided in the first aspect of the present application.
In another embodiment of the present application, the organic electroluminescent device may be, for example, a blue organic electroluminescent device.
In another embodiment of the present application, the functional layer comprises a hole transport layer comprising the organic compound.
In one embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked.
In one embodiment, anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. The anode material specifically comprises: 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 such as ZnO: al and SnO 2 : sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Also preferably, a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
In one embodiment, hole transport layer 321 may comprise one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, and in one embodiment, hole transport layer 321 is comprised of an organic compound of the present application.
In one embodiment, electron blocking layer 322 may comprise one or more materials, which may be selected from carbazole multimers or other types of compounds, without limitation. In one embodiment, electron blocking layer 322 is comprised of compound HT-12.
In this application, the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may further include a material selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited herein. In one embodiment, electron transport layer 350 is comprised of a combination of compound LiQ and compound ET-01.
In this application, the organic electroluminescent layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, the organic electroluminescent layer 330 is composed of a host material and a guest material, and holes injected into the organic electroluminescent layer 330 and electrons injected into the organic electroluminescent layer 330 may be combined at the organic electroluminescent layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic electroluminescent layer 330 may be a metal chelating compound, bisstyryl derivative, aromatic amine derivative, dibenzofuran derivative or other types of materials, and in one embodiment, the host material of the organic electroluminescent layer is composed of a compound BH-1.
The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. In one embodiment, the guest material is compound BD-1.
In one embodiment, the cathode 200 includes a cathode material that is a material with a small work function that facilitates electron injection into the functional layer.In particular, specific examples of cathode materials 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; multilayer materials such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. Preferably, a metal electrode containing silver and magnesium is used as the cathode.
In this application, as shown in fig. 1, a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. In some embodiments of the present application, hole injection layer 310 may be composed of the compound HAT-CN.
In one embodiment, as shown in fig. 1, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. In one embodiment, the electron injection layer 360 may include ytterbium (Yb).
A third aspect of the present application provides an electronic device comprising the organic electroluminescent device provided in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is an electronic device 400, and the electronic device 400 includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthesis method of the nitrogen-containing compound of the present application is specifically described below with reference to synthesis examples, but the present application is not limited thereto.
All compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
Synthesis of intermediate IM a1-X
Taking IM a1-1 as an example, the synthesis of IM a1-X is described:
(1) Methyl 2-bromo-5-chlorobenzoate (15.00 g,60.12 mmol), 3-methoxydibenzofuran-2-boronic acid (14.55 g,60.12 mmol), potassium carbonate (16.62 g,120.25 mmol), tetrabutylammonium bromide (1.94 g,6.01 mmol), toluene (75 mL), ethanol (45 mL) and deionized water (30 mL) were added to a three-necked flask, stirred under nitrogen for 15min, then tetrakis (triphenylphosphine) palladium (0.70 g,0.60 mmol) was added and heated to 75-80℃and stirred for 5h; the reaction solution was cooled to room temperature, toluene (100 mL) was added for extraction, the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed from the organic phases under reduced pressure to give a crude yellow oil, and the crude product was recrystallized and purified using a dichloromethane/ethanol system to give an off-white solid IM a 1 -a 1 (15.90 g, yield: 72.10%).
(2) Intermediate IM a 1 -a 1 (13.50 g,36.80 mmol) and tetrahydrofuran (100 mL) were added to a three-necked flask and stirred, 3M solution of methyl magnesium bromide in THF (24.50 mL,73.60 mmol) was slowly added dropwise under nitrogen protection, and after the addition was completed, the mixture was stirred at room temperature for 1 hour, then the temperature was raised to 60 to 66℃and the mixture was stirred for reaction for 6 hours; cooling the reaction solution to room temperature, adding dichloromethane (135 mL), slowly adding deionized water (100 mL) under stirring, slowly adding the reaction solution into 1mol/L dilute hydrochloric acid (100 mL), standing for liquid separation after stirring, drying the organic phase by using anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; obtaining yellowish oily matter IM a 1 -a 2 (12.40 g, yield: 91.85%).
(3) Intermediate IM a 1 -a 2 (12.00 g,32.71 mmol) and acetonitrile (100 mL) are added into a three-neck flask, stirring is started, the system is cooled to 0-10 ℃, then 1M methylene dichloride solution (32.71 mL,32.71 mmol) of boron tribromide is dropwise added, the temperature is controlled to 0-10 ℃, after 1h, the system is naturally warmed to room temperature, and stirring is carried out for about 5h; deionized water (100 mL) and methylene dichloride (100 mL) are added into the reaction solution, the solution is separated, the organic phase is dried by anhydrous magnesium sulfate, filtered and the solvent is removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using n-heptane to give intermediate IM a1-1 (7.60 g, yield: 69.42%) as a white solid.
Referring to the synthesis of IM a1-1, the other IM a1-X listed in Table 1 were synthesized, except that raw material 1 was used in place of methyl 2-bromo-5-chlorobenzoate in step (1), raw material 2 was used in place of 3-methoxydibenzofuran-2-boronic acid in step (1), the structures of raw material 1, raw material 2 and IM a1-X, and the final step yields were as shown in Table 1.
TABLE 1
Synthesis of Compound 1-1
(1) IM a1-1 (7.00 g,20.91 mmol), 4-aminobiphenyl (3.54 g,20.91 mmol), tris (dibenzylideneacetone) dipalladium (0.19 g,0.21 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.17 g,0.42 mmol) and sodium tert-butoxide (3.01 g,31.36 mmol) were added to toluene (70 mL), heated to 108℃under nitrogen protection, stirred for 2h, then cooled to room temperature, the reaction solution was washed with water and then separated, the organic phase was dried over anhydrous magnesium sulfate, and the filtrate was filtered and the solvent was removed under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give intermediate IM A1-A1 (7.20 g, 73.64%) as an off-white solid.
(2) IM A1-A1 (6.00 g,12.83 mmol), 4-bromobiphenyl (2.99 g,12.83 mmol), tris (dibenzylideneacetone) dipalladium (0.12 g,0.13 mmol), 2-dicyclohexylphosphorus-2 ',6' -dimethoxybiphenyl (0.12 g,0.26 mmol) and sodium tert-butoxide (1.85 g,19.25 mmol) were added to toluene (60 mL), heated to 108℃under nitrogen protection, stirred for 3h, then cooled to room temperature, the reaction solution was washed with water and then separated, the organic phase was dried over anhydrous magnesium sulfate, and the filtrate was filtered and the solvent was removed under reduced pressure; the crude product was purified by recrystallization from toluene to give compound 1-1 (5.30 g, yield 66.7%) as a white solid. Mass spectrometry: m/z=620.3 [ m+h ]] + ；
The compounds listed in Table 4 were synthesized by referring to the method for the compounds 1-1, except that IM a1-X was replaced with the raw material 3, 4-aminobiphenyl was replaced with the raw material 4, 4-bromobiphenyl was replaced with the raw material 5, and the main raw materials used, the synthesized compounds and the final step yields and mass spectrometry results thereof were shown in Table 2.
TABLE 2
The above synthesized compounds were subjected to nuclear magnetic resonance hydrogen spectrum analysis to obtain the data shown in table 3 below:
TABLE 3 Table 3
Example 1: preparation of blue organic electroluminescent device
The anode was prepared by the following procedure: the ITO/Ag/ITO thickness isThe ITO substrate of (C) was cut into a size of 40mm (length). Times.40 mm (width). Times.0.7 mm (thickness), and a photolithography step was used to prepare an experimental substrate having cathode, anode and insulating layer patterns, and ultraviolet ozone and O were used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
On an experimental substrate (anode), HAT-CN and a compound HT-11 are subjected to co-evaporation at an evaporation rate ratio of 2% to 98%, and the thickness is equal toIs deposited on the Hole Injection Layer (HIL) to form a layer of compound 1-1 having a thickness +.>Is provided.
Vacuum evaporating HT-12 on the hole transport layer to form a film with a thickness ofIs a barrier to electrons.
On the electron blocking layer, compound BH-1 (doping host) and compound BD-1 (doping guest) were mixed in 98%: co-evaporation is carried out according to the thickness proportion of 2 percent to form the film with the thickness ofAn organic electroluminescent layer (EML).
On the light-emitting layer, the compounds ET-01 and LiQ are carried out together in a thickness ratio of 1:1 and vapor deposition is carried out to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:10, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +.>Cathode of (2)。
In addition, the thickness of the vacuum evaporation on the cathode isAnd thus completing the fabrication of the blue organic electroluminescent device.
Examples 2 to 42
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound 1-1 in example 1 was replaced with the compound in table 5 when preparing a hole transport layer.
Comparative examples 1 to 3
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound 1-1 in example 1 was replaced with the compound in table 5 when preparing a hole transport layer.
The blue organic electroluminescent devices prepared in examples 1 to 42 and comparative examples 1 to 3 were subjected to performance test, in particular, at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 15mA/cm 2 The test results are shown in table 5 below.
The material structures used in the above examples and comparative examples are shown in table 4 below:
TABLE 4 Table 4
TABLE 5
From the data in Table 5, it is understood that the organic electroluminescent devices of examples 1 to 42 are significantly improved in performance over the organic electroluminescent devices of comparative examples 1 to 3. Specifically, examples 1-42 improved current efficiency by at least 19.0% and life by at least 17.0%.
Claims (13)
1. An organic compound, characterized in that the structure of the organic compound is shown in formula 1:
wherein one of the ring A and the ring B is selected from the structure shown in formula 2, the other is a benzene ring, and the formula 2 is represented by the formula 2 and the formula 1A mutually fused position;
x is selected from C (R) 1 R 2 ) O or S;
R 1 and R is 2 The same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms or deuterated alkyl with 1-10 carbon atoms;
R 3 and R is 4 The same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms;
L、L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen groupsCyano, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroaryl having 12 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 24 carbon atoms, halogenated alkyl having 1 to 10 carbon atoms or deuterated alkyl having 1 to 10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring.
2. The organic compound according to claim 1, wherein L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms;
optionally, the substituents in L are the same or different and are each independently selected from deuterium, a halogen group, cyano, alkyl having 1 to 5 carbon atoms, or phenyl.
3. The organic compound according to claim 1, wherein L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group;
alternatively, the substituents in L are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
4. The organic compound according to claim 1, wherein L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms;
alternatively, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups having 5 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, deuterated aryl groups having 6 to 12 carbon atoms or alkyl groups having 1 to 5 carbon atoms.
5. The organic compound according to claim 1, wherein L 1 And L 2 And are identical or different and are each independently selected from a single bond, a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
the substituted group W has one or more than two substituents, the substituents in the substituted group W are respectively and independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl or phenyl, and when the number of the substituents on the group W is more than 1, the substituents are the same or different.
6. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms or substituted or unsubstituted heteroaryl groups with 12-24 carbon atoms;
alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups with 5-12 carbon atoms, aryl groups with 6-12 carbon atoms, deuterated aryl groups with 6-12 carbon atoms or alkyl groups with 1-5 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a fluorene ring.
7. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 And are identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups V, wherein unsubstituted groups V are selected from the group consisting of:
the substituted group V has one or more than two substituents, the substituents in the substituted group V are respectively and independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl, phenyl, naphthyl or pentadeuterated phenyl, and when the number of the substituents on the group V is more than 1, the substituents are the same or different.
8. The organic compound according to claim 1, wherein,identical or different and are each independently selected from the group consisting of:
9. the organic compound according to claim 1, wherein R 1 And R is 2 Are all methyl groups;
R 3 and R is 4 The same or different and are each independently selected from methyl or phenyl.
10. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
11. an organic electroluminescent device, characterized in that it comprises an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound according to any one of claims 1 to 10.
12. The organic electroluminescent device of claim 11, wherein the functional layer comprises a hole transport layer comprising the organic compound.
13. An electronic device comprising the organic electroluminescent device as claimed in claim 11 or 12.
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| CN202310440255.9A CN117645609A (en) | 2023-04-20 | 2023-04-20 | Organic compound, organic electroluminescent device and electronic device |
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| CN202310440255.9A CN117645609A (en) | 2023-04-20 | 2023-04-20 | Organic compound, organic electroluminescent device and electronic device |
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