CN115232097A - Organic compound, application thereof and organic electroluminescent device comprising organic compound - Google Patents
Organic compound, application thereof and organic electroluminescent device comprising organic compound Download PDFInfo
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- CN115232097A CN115232097A CN202110433387.XA CN202110433387A CN115232097A CN 115232097 A CN115232097 A CN 115232097A CN 202110433387 A CN202110433387 A CN 202110433387A CN 115232097 A CN115232097 A CN 115232097A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 52
- 238000002347 injection Methods 0.000 claims abstract description 20
- 239000007924 injection Substances 0.000 claims abstract description 20
- 239000010410 layer Substances 0.000 claims description 88
- -1 nitro, hydroxyl Chemical group 0.000 claims description 86
- 230000005525 hole transport Effects 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 12
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 8
- 125000001725 pyrenyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 7
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003172 aldehyde group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 65
- 230000005540 biological transmission Effects 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000011799 hole material Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000012295 chemical reaction liquid Substances 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 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 10
- 238000003756 stirring Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
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- YPPQXIRIFYYANY-UHFFFAOYSA-N (8-bromonaphthalen-1-yl)boronic acid Chemical compound C1=CC(Br)=C2C(B(O)O)=CC=CC2=C1 YPPQXIRIFYYANY-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- XNDLRPFISURYTA-UHFFFAOYSA-N 1-bromo-8-iodonaphthalene Chemical compound C1=CC(I)=C2C(Br)=CC=CC2=C1 XNDLRPFISURYTA-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
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- 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 2
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- 238000005401 electroluminescence Methods 0.000 description 2
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- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Chemical group 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical group [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HIEUZGKQGFFELW-UHFFFAOYSA-N methyl 8-bromonaphthalene-1-carboxylate Chemical compound C1=CC(Br)=C2C(C(=O)OC)=CC=CC2=C1 HIEUZGKQGFFELW-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KPOJHLVDVOUVBF-UHFFFAOYSA-N n-(4-tert-butylphenyl)-9,9-dimethylfluoren-3-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 KPOJHLVDVOUVBF-UHFFFAOYSA-N 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical class 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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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- 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
- C07D311/78—Ring systems having three or more relevant rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/76—Dibenzothiophenes
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- 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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Abstract
The invention relates to an organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound and an organic electroluminescent device containing the compound. The organic compound has a structure shown in a formula (1). The organic compound has excellent hole transmission efficiency and injection capability, and when the compound is applied to an organic electroluminescent device, the working voltage of the device can be effectively reduced, and the efficiency of the device can be improved.
Description
Technical Field
The invention relates to an organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound and an organic electroluminescent device containing the compound.
Background
In recent years, optoelectronic devices based on organic materials have been developed rapidly and are the focus of research in the field. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLEDs have been developed particularly rapidly, and have been commercially successful in the field of information display. The OLED can provide red, green and blue colors with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of gorgeous colors, lightness, thinness, softness and the like.
The core of the OLED device is a multilayer thin film structure containing various organic functional materials. Common functionalized organic materials are: a hole injection material, a hole transport material, a hole blocking material, an electron injection material, an electron transport material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light.
Conventional fluorescent emitters mainly emit light by using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet excitons and singlet excitons, which are called phosphorescent emitters, and the energy conversion efficiency can be increased by up to four times as compared with conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. Thermal excitation sensitized fluorescence (TASF) technology also achieves higher luminous efficiency by sensitizing the emitter by energy transfer using TADF-based materials.
The hole transport material has obvious influence on the performance of the device, and on one hand, the hole transport material needs to have a proper HOMO energy level and a proper energy gap between the hole material and the anode, so that the hole transport material is favorable for injecting holes and can help to reduce the working voltage; on the other hand, the hole transport material regulates and controls the transport balance of carriers in the device, improves the carrier mobility of the hole transport material, can improve the luminous efficiency, and delays the attenuation of the device. Although products adopting the OLED display technology are commercialized at present, there are still further increasing requirements on the efficiency, the service life, and the like of the device. Therefore, there is a need in the art to develop a wider variety of organic materials for organic electroluminescent devices, such that the devices have higher luminous efficiency, lower driving voltage and longer lifetime.
Disclosure of Invention
In order to further meet the requirements of the OLED device for increasing its photoelectric properties and the requirements of the mobile electronic device for energy saving, it is necessary to develop a new and efficient OLED material, and it is important to develop a new hole transport material with high hole injection capability and high mobility.
An object of the present invention is to provide an organic compound that can be used as an organic thin layer material in an organic electroluminescent device, resulting in a device having a lower voltage and higher luminous efficiency.
The invention provides an organic compound, which has a structure shown as a formula (1):
in the formula (1), the acid-base catalyst,
said L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group;
x is selected fromS、O、SiR 5 R 6 Or CR 7 R 8 ；
Ar is 1 、Ar 2 、Ar 3 、Ar 4 Each independently selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
m and n are each independently 0 or 1, and m + n =1;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde group, ketone group, ester group, carbonyl substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused ring aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 fused ring heteroaryl, substituted or unsubstituted C6-C60 arylamino and substituted or unsubstituted C3-C60 heteroarylamino; r is as defined above 1 、R 2 、R 3 、R 4 May each independently be fused to the aromatic ring to which it is attached; when the substituent is plural, these substituents may be bonded to each other via a chemical bond to form a ring, for example, when there are plural R 1 -R 4 When a substituent is present, R is 1 -R 4 May form a ring by chemical bonding between adjacent two of them.
The R is 5 、R 6 、R 7 、R 8 Each independently selected from one of substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl; and the above R 7 And R 8 Are not connected with each other through chemical bonds to form a ring;
each of said a, b, c, d is independently selected from 1 to the maximum desirable integer value, i.e., each is desirableUpper limit of the generation position, a plurality of R 1 A plurality of R 2 A plurality of R 3 A plurality of R 4 Each is the same or different; when a, b, c, d are each independently an integer value greater than 1, a plurality of R' s 1 A plurality of R 2 A plurality of R 3 Or a plurality of R 4 In (b), two adjacent groups may be independently linked to each other via a chemical bond to form a ring;
when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is selected from one or a combination of at least two of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde group, ketone group, ester group, carbonyl group, chain alkyl group of C1 to C30, alkoxy group of C1 to C30, cycloalkyl group of C3 to C20, heterocycloalkyl group of C3 to C20, aryl group of C6 to C60, and heteroaryl group of C3 to C60.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the present specification, the expression of Ca to Cb represents that the group has a carbon number of a to b, and generally the carbon number does not include the carbon number of the substituent unless otherwise specified.
In the present specification, the expression of the "-" underlined loop structure means that the linking site is located at an arbitrary position on the loop structure capable of forming a bond.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present invention, unless otherwise specified, the expression of a chemical element generally includes the concept of its isotope, for example, the expression of "hydrogen (H)" includes its isotope 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., will not be described in detail.
The hetero atom in the heteroaryl group in the present invention generally means an atom or an atomic group selected from N, O, S, P, si and Se, and is preferably selected from N, O and S.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. By monocyclic aryl is meant a group containing at least one phenyl group in the molecule, and when at least two phenyl groups are present in the molecule, the phenyl groups are independent of each other and are linked by a single bond, as exemplified by: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. The fused ring aryl group means a group having at least two aromatic rings in a molecule, and the aromatic rings are not independent of each other but are fused to each other with two adjacent carbon atoms in common. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,
And mesityl and derivatives thereof. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9' -spirobifluorene and benzofluorenyl.
In the present invention, the substituted or unsubstituted C3 to C60 heteroaryl includes monocyclic heteroaryl and fused heteroaryl, preferably C3 to C30 heteroaryl, more preferably C4 to C20 heteroaryl, and still more preferably C5 to C12 heteroaryl. Monocyclic heteroaryl refers to a heteroaryl group having at least one heteroaryl group in a molecule, and when the molecule has one heteroaryl group and another group (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other group are independently connected by a single bond, and examples of monocyclic heteroaryl groups include: furyl, thienyl, pyrrolyl, pyridyl and the like. The fused ring heteroaryl group means a group which has at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in a molecule, and which are not independent of each other but share two adjacent atoms fused with each other. Examples of fused heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the aryl group. Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the heteroaryl group.
In the present invention, the aryloxy group includes a monovalent group composed of the above-mentioned aryl group, heteroaryl group and oxygen.
Examples of the C6 to C30 arylamino group mentioned in the present invention include: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino and the like.
Examples of the C3 to C30 heteroarylamino group mentioned in the present invention include: pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.
The chain alkyl group referred to in the present invention includes a straight chain alkyl group and a branched chain alkyl group unless otherwise specified. Specifically, the substituted or unsubstituted C1 to C30 chain alkyl group is preferably a substituted or unsubstituted C1 to C16 chain alkyl group, and more preferably a substituted or unsubstituted C1 to C10 chain alkyl group. Substituted or unsubstituted C3-C30 cycloalkyl, preferably substituted or unsubstituted C3-C20 cycloalkyl, more preferably substituted or unsubstituted C3-C10 cycloalkyl, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, tert-pentyl, cyclohexyl, adamantyl and the like.
Further, the organic compound of the present invention represented by the formula (1), wherein X is preferably O or CR 7 R 8 。
Still further, when X is O, the organic compound of the present invention preferably has a structure represented by any one of the formula (2-1), the formula (2-2) or the formula (2-3):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 、R 4 A, b, c, d are all as defined in formula (1).
Preferably, in the formula (2-1), the formula (2-2) or the formula (2-3), L is 1 、L 2 Are all single bonds.
And/or, preferably, in the formula (2-1), the formula (2-2) and the formula (2-3), a, b, c and d are all 0.
And/or, preferably, in formula (2-1), formula (2-2), formula (2-3), said Ar 1 、Ar 2 、Ar 3 、Ar 4 Each independently is one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; preferably said r 1 、Ar 2 、Ar 3 、Ar 4 Each independently selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, anthryl, phenanthryl, indenyl, anthryl, triphenylene, pyrenyl, perylenyl,
Phenyl and tetracenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl, 9-dipentylfluorenylOne of a phenyl group, a 9, 9-dihexylfluorenyl group, a 9, 9-diphenylfluorenyl group, a 9, 9-dinaphthylfluorenyl group, a spirofluorenyl group and a benzofluorenyl group, a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an acridinyl group, an isobenzofuryl group, an isobenzothienyl group, an acridinyl group, a pyridyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, and a phenazinyl group;
ar above 1 、Ar 2 、Ar 3 、Ar 4 When the substituent group is contained, the substituent group is one or a combination of at least two of deuterium, halogen, chain alkyl of C1-C10, alkoxy of C1-C10, cycloalkyl of C3-C10, heterocycloalkyl of C3-C10, aryl of C6-C30 and heteroaryl of C3-C30.
Still further, when said X is CR 7 R 8 In this case, the organic compound of the present invention preferably has a structure represented by any one of the formula (3-1), the formula (3-2), the formula (3-3), the formula (3-4) or the formula (3-5):
wherein, L is 1 、Ar 1 、Ar 2 、R 1 、R 2 、R 3 、R 4 、R 7 、R 8 A, b, c, d are all as defined in formula (1).
Preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4), formula (3-5), L is 1 Is a single bond.
And/or, preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), a, b, c, d are all 0.
And/or, preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), ar 1 And Ar 2 Each independently is one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; preferably said Ar is 1 And Ar 2 Each independently selected from substituted or unsubstitutedThe following groups: phenyl, naphthyl, anthryl, phenanthryl, indenyl, anthryl, triphenylene, pyrenyl, perylenyl,
Phenyl and tetracenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl, 9,9-diamylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl, furyl, thienyl, o one of pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, and phenazinyl;
further preferably, in the formula (3-1), the formula (3-2), the formula (3-3), the formula (3-4) or the formula (3-5), R is 7 、R 8 Each independently is preferably one of a substituted or unsubstituted C1-C18 chain alkyl group and a substituted or unsubstituted C6-C24 aryl group; more preferably, said R 7 、R 8 Each independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and adamantyl, more preferably phenyl, naphthyl, anthryl, phenanthryl, indenyl, fluoranthyl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
<xnotran> , 2- , 3- ,4- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- , , , , , , , , , , , , , , </xnotran>One of benzothienyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl and phenazinyl;
when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is one or a combination of at least two selected from deuterium, halogen, a C1-C10 chain alkyl group, a C1-C10 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group.
Further, the organic compound of the present invention has a structure represented by any one of the formula (2-1-1), the formula (2-2-1), and the formula (2-3-1), wherein L 1 、Ar 1 、Ar 2 、L 2 、Ar 3 、Ar 4 Are as defined in formula (1):
still further, the organic compound of the present invention has a structure represented by any one of formula (3-1-1), formula (3-2-1), formula (3-3-1), formula (3-4-1), formula (3-5-1), formula (3-1-2), formula (3-2-2), formula (3-3-2), formula (3-4-2) or formula (3-5-2), wherein L is 1 、Ar 1 、Ar 2 Are as defined in formula (1):
still further, in each of the above general formulae of the organic compound of the present invention, ar is represented by 1 -Ar 4 The following substituted or unsubstituted groups may be further preferred:
when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is one or a combination of at least two selected from deuterium, halogen, a chain alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 3 to 30 carbon atoms.
The inventor of the invention researches and discovers that the structure of the chemical formula (A) has good planarity and plane conjugation capability, so that the triarylamine compound has excellent charge transport capability, and has higher hole mobility, improved injection capability and improved device efficiency.
In the invention, a series of triarylamine compounds are designed by adopting a unique parent nucleus structure shown as a formula (A) as a molecular core structure, and the molecules have excellent hole mobility. The compound of the invention can be generally used as a carrier transport layer material in an organic electroluminescent device, and comprises a hole transport layer material, an electron blocking layer material and the like.
The general formula (1) structure of the invention is specifically that two naphthyl groups in the binaphthyl compound are connected through a divalent atom to form a six-membered ring structure with a plane, and the naphthyl groups have the characteristic of plane rigidity, so that the molecules of the formula (1) can form a larger plane pi conjugated structure. The large-plane conjugated structure further promotes the excellent charge transmission capability of binaphthyl, improves the orbital level of molecules, enables the molecules to have lower HOMO level, and can enhance the injection capability of materials from the positive pole.
It is noted that the possible actions of the various groups/features are described separately herein for ease of illustration, but that this does not mean that the groups/features act in isolation. In fact, the reason for obtaining good performance is essentially an optimized combination of the whole molecule, as a result of synergy between the individual groups, rather than the effect of a single group.
Further, the compound of the general formula of the present invention is preferably the following specific compound, but the present invention is not limited to the specific compound shown below:
as another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. In particular, the application as a light-emitting layer material in an organic electroluminescent device is preferred, and the application as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device is more preferred.
In addition to the organic electroluminescent device, the compound of the present invention can be applied to a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains a compound represented by formula (1) as described above or a compound having a structure represented by at least one of C1 to C338 as described above.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the organic layer contains the compound of the general formula (1) or the compound of at least one structure of C1-C338.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or the display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The mass spectrum characterization data in the following synthesis examples were obtained by a ZAB-HS type mass spectrometer test manufactured by Micromass, UK.
Synthesis example 1: synthesis of Compound C1
In a 500mL single-necked flask, 30.0g (90.4 mmol) of 1-bromo-8-iodonaphthalene, 20.4g (108.4 mmol) of 2-hydroxy-1-naphthaleneboronic acid, 1.00g (0.900 mmol) of tetrakis (triphenylphosphine) palladium (i.e., pd (PPh) 3 ) 4 ) 300mL of Toluene (Toluene), 50mL of ethanol, 30mL of water, 16.2 (117.6 mmol) of potassium carbonate (K) 2 CO 3 ) Vacuumizing and changing nitrogen for 3 times, and heating to 90 ℃ for reaction for 7 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain 20.0g of yellow powder A-1, measured value of M/Z: 349 (M + H).
In a 500mL single-necked flask, 20.0g (57.4 mmol) of A-1 and 11.8g (86.0 mmol) of potassium carbonate (K) were charged 2 CO 3 ) 400mLN, and N-Dimethylformamide (DMF), heating to 120 ℃ for reaction for 16h, and stopping the reaction after the reaction is finished. Cooling to room temperature, pouring the reaction liquid into water, extracting with ethyl acetate, drying with anhydrous sodium sulfate, concentrating to obtain yellow oily matter, stirring in normal hexane, separating out solid, and performing suction filtration to obtain 6.5g of light yellow powder A-2, M/Z measured value: 269 (M + H).
Dissolving 6.5g (24.3 mmol) of A-2 in tetrahydrofuran in a 250mL three-necked bottle, cooling the reaction system to 0 ℃ through an ice salt bath, then adding 4.3g (24.3 mmol) of N-bromosuccinimide into the reaction liquid in batches, continuing to react for 4 hours after the addition is finished, pouring into a sodium thiosulfate solution, extracting with ethyl acetate, drying with anhydrous sodium sulfate, and concentrating to obtain a yellow solid. Recrystallization from toluene and ethanol, suction filtration gave 6.0g of a pale yellow powder A-3, found M/Z: 347 (M + H)
In a 250mL three-necked flask, 6.0g (17.3 mmol) of A-3, 2.7g (15.6 mmol) of diphenylamine, and 0.16g (0.173 mmol) of tris (dibenzylideneacetone) dipalladium (i.e., pd) were sequentially added 2 (dba) 3 ) 0.1mL of tri-tert-butylphosphine xylene solution, 2.5g (26.0 mmol) of sodium tert-butoxide (NaOBu-t) and 80mL of Toluene (Toluene), the reaction mixture was evacuated and purged with nitrogen 3 times, and the reaction was heated to 100 ℃ for 4 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, enabling the reaction liquid to pass through a silica gel short column, leaching the toluene until no product exists, concentrating the toluene to obtain yellow oily matter, adding methanol, stirring, and slowly separating out a solid. The solid was recrystallized from toluene and ethanol and filtered with suction to give 5.2g of the compound C1 as a pale yellow powder, found in M/Z: 436 (M + H)
The compounds of synthesis examples 2 to 15 were synthesized by referring to the method of synthesis example 1 using a-3 as an intermediate, and the specific structures are shown in table 1:
table 1:
synthesis example 16: compound C113
In a 500mL single-necked flask, 30.0g (100.0 mmol) of 1, 4-dibromo-2-naphthol, 25.0g (100.0 mmol) of 8-bromo-1-naphthaleneboronic acid, 1.00g (0.900 mmol) of tetrakis (triphenylphosphine) palladium (i.e., pd (PPh) 3 ) 4 ) 300mL of Toluene (Toluene), 50mL of ethanol, 50mL of water 16.2 (117.6 mmol) of potassium carbonate (K) 2 CO 3 ) Vacuumizing and changing nitrogen for 3 times, and heating to 90 ℃ for reaction for 7 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain 27.0g of brown powder B-1, actual measured value of M/Z: 427 (M + H).
In a 500mL single-necked flask, 21.0g (50.0 mmol) of B-1 and 19.3g (70.0 mmol) of potassium carbonate (K) were charged 2 CO 3 ) 350mLN, and N-Dimethylformamide (DMF), heating to 120 deg.C, reacting for 16h, and stopping reaction after reaction. Cooling to room temperature, pouring the reaction solution into water, extracting with ethyl acetate, drying with anhydrous sodium sulfate, concentrating to obtain yellow oily substance, stirring in n-hexane, separating out solid, and filtering to obtain 10.6g yellow powder B-2, M/Z measured value: 347 (M + H).
In a 250mL three-necked flask, 8.5g (24.6 mmol) of B-2, 8.3g (24.6 mmol) of N- (4- (tert-butyl) phenyl) -9, 9-dimethyl-9H-fluoren-3-amine, 0.23g (0.246 mmol) of tris (dibenzylideneacetone) dipalladium (i.e., pd) were added in this order 2 (dba) 3 ) 0.1mL of tri-tert-butylphosphine xylene solution, 3.5g (37.0 mmol) of sodium tert-butoxide (NaOBu-t) and 150mL of Toluene (Toluene), the reaction mixture was evacuated and purged with nitrogen 3 times, and the reaction was heated to 100 ℃ for 4 hours. And stopping the reaction after the reaction is finished. Cooling the mixture to the room temperature,and (3) enabling the reaction liquid to pass through a silica gel short column, leaching toluene until no product exists, concentrating the toluene to obtain yellow oily matter, adding methanol, stirring, and slowly separating out a solid. The solid was recrystallized from toluene and ethanol and filtered with suction to give 7.3g of the compound C113 as a pale yellow powder, found in M/Z: 608 (M + H)
The compounds of synthesis examples 17 to 26 were synthesized by referring to the method of synthesis example 16 using B-2 as an intermediate, and the specific structures are shown in table 2:
table 2:
synthesis example 27: compound C125
In a 250mL single-necked flask, 18.0g (70.3 mmol) of 1-bromo-6-chloro-2-naphthol, 19.4g (77.3 mmol) of 8-bromo-1-naphthaleneboronic acid, 0.80g (0.700 mmol) of tetrakis (triphenylphosphine) palladium (i.e., pd (PPh) 3 ) 4 ) 180mL of Toluene (Toluene), 20mL of ethanol, 20mL of water, 11.6 (84.5 mmol) of potassium carbonate (K) 2 CO 3 ) Vacuumizing and changing nitrogen for 3 times, and heating to 90 ℃ for reaction for 7 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain 14.6g of earthy yellow powder C-1, measured value of M/Z: 383 (M + H).
In a 250mL single-necked flask, 14.0g (36.5 mmol) of C-1, 6.9g (50.0 mmol) of potassium carbonate (K) were added 2 CO 3 ) 200mLN, N-Dimethylformamide (DMF), heating to 120 ℃ for reaction for 16h, and stopping reaction after the reaction is finishedIt should be used. After cooling to room temperature, the reaction mixture was poured into water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated and passed through a silica gel column (petroleum ether/ethyl acetate, 10/1) to give a pale yellow solid, 7.8g of yellow powder C-2, M/Z found: 303 (M + H).
Into a 250mL three-necked flask, 5.0g (16.5 mmol) of C-2 and 6.0g (16.5 mmol) of N- [1,1' -biphenyl were added in this order]-4-yl-9, 9-dimethyl-9H-fluoren-2-amine, 0.16g (0.170 mmol) of tris (dibenzylideneacetone) dipalladium (i.e. Pd) 2 (dba) 3 ) 0.1mL of tri-tert-butylphosphine xylene solution, 3.0g (22.0 mmol) of sodium tert-butoxide (NaOBu-t) and 80mL of Toluene (Toluene), the reaction mixture was evacuated and purged with nitrogen 3 times, and the reaction mixture was heated to 120 ℃ for 6 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, enabling the reaction liquid to pass through a silica gel short column, leaching the toluene until no product exists, concentrating the toluene to obtain yellow oily matter, adding methanol, stirring, and slowly separating out a solid. The solid was recrystallized from toluene and ethanol and filtered with suction to give 5.3g of the compound C125 as a pale yellow powder, found in M/Z: 628 (M + H)
The compounds of synthesis examples 28 to 38 were synthesized by referring to the method of synthesis example 27 using C-2 as an intermediate, and the specific structures are shown in table 3:
table 3:
the synthesis method of the intermediate D-3 required by the formula (6-1) is as follows:
in a 250mL single-necked flask, 20.0g (75.8 mmol) of methyl 8-bromo-1-naphthoate, 17.2g (83.3 mmol) of 4-chloro-1-naphthalene boronic acid, 0.80g (0.700 mmol) of tetrakis (triphenylphosphine) palladium (i.e., pd (PPh) 3 ) 4 ) 180mL of Toluene (Toluene), 30mL of ethanol, 30mL of water, 20.9g (151.6 mmol) of potassium carbonate (K) 2 CO 3 ) Vacuumizing and changing nitrogen for 3 times, and heating to 90 ℃ for reaction for 7 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain 20.6g of earthy yellow powder D-1, wherein the measured value of M/Z is as follows: 347 (M + H).
In a dry 500mL three-necked flask, a reflux condenser tube, a nitrogen conduit, and a constant pressure dropping funnel were provided. 15g (43.4 mmol) of D-1 was dissolved in anhydrous tetrahydrofuran solution dried with sodium, placed in a bottle and cooled to-5 ℃ by means of a ice salt bath, and a tetrahydrofuran solution of methylmagnesium bromide (43.4 mL,130.2mmol,3.0M in THF) was slowly added dropwise to the above solution via a constant pressure dropping funnel under nitrogen protection, after completion of the dropwise addition, the reaction was allowed to incubate for half an hour, then the ice salt bath was removed and allowed to warm to room temperature and stirred overnight. The reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by concentration to give a brown oil. The crude product is purified by column chromatography (petrol ether/ethyl acetate, 10/1-5/1) to give 8.9g of a pale yellow solid D-2, the measured value of M/Z: 347 (M + H).
8g (23.1 mmol) of D-2 was dissolved in a mixture of 30mL of acetic acid and 5mL of concentrated hydrochloric acid, heated to 100 ℃ for reaction for 16 hours, and then cooled to room temperature to precipitate a solid. The solid was collected and washed with water and methanol to give 7.0g of product D-3, M/Z found: 329 (M + H).
Similarly, intermediate E-3, required for formula (6-2), can be obtained with reference to the synthetic procedure for D-3:
replacement of 4-chloro-1-naphthalene boronic acid in D-3 with 8-chloro-1-naphthalene boronic acid, found M/Z: 329 (M + H). Similarly, intermediate F-3 required for formula (6-3) can be obtained by reference to the synthetic procedure for D-3:
replacement of 4-chloro-1-naphthalene boronic acid in D-3 with 7-chloro-1-naphthalene boronic acid, found M/Z: 329 (M + H). Similarly, the intermediate G-3 required for formula (6-4) can be obtained by reference to the synthetic procedure for D-3:
replacement of 4-chloro-1-naphthalene boronic acid in D-3 with 6-chloro-1-naphthalene boronic acid, found M/Z: 329 (M + H). Similarly, the intermediate H-3 required for formula (6-5) can be obtained by reference to the synthetic procedure for D-3:
replacement of 4-chloro-1-naphthalene boronic acid in D-3 with 5-chloro-1-naphthalene boronic acid, found M/Z: 329 (M + H). The synthesis method of the intermediate I-3 required by the formula (7-1) is as follows:
in a 500mL single-necked flask, 30.0g (90.4 mmol) of 8-iodo-1-bromonaphthalene, 19.6g (95.0 mmol) of 4-chloro-1-naphthylboronic acid, 1.1g (0.900 mmol) of tetrakis (triphenylphosphine) palladium (i.e., pd (PPh) 3 ) 4 ) 300mL of Toluene (Toluene), 50mL of ethanol, 50mL of water, 20.9g (151.6 mmol) of potassium carbonate (K) 2 CO 3 ) Vacuumizing and changing nitrogen for 3 times, and heating to 90 ℃ for reaction for 7 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain 26.5g of earthy yellow powder I-1, measured value of M/Z: 367 (M + H).
In a dry 500mL three-necked flask, a nitrogen gas tube and a constant pressure dropping funnel were provided. 20g (54.6 mmol) of I-1 are dissolved in 250mL of anhydrous tetrahydrofuran solution which has been dried over sodium, placed in a flask and cooled to-78 ℃ by means of a liquid nitrogen-acetone bath. Under the protection of nitrogen, an n-butyllithium solution (26.0mL, 65.2mmol,2.5M in hexane) was slowly added dropwise to the solution through a constant-pressure dropping funnel, after dropwise addition, the reaction was kept at an incubation temperature for half an hour, 11.9g (65.2 mmol) of benzophenone was dissolved in 80mL of anhydrous tetrahydrofuran, and the solution was added dropwise to the reaction mixture, and the mixture was stirred overnight at room temperature. The reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, and the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent to give a brown oil. The crude product is purified by column chromatography (petrol ether/ethyl acetate, 10/1-5/1) to give 18g of a pale yellow solid I-2, M/Z found: 471 (M + H).
18g (38.2 mmol) of I-2 was dissolved in a mixture of 200mL of acetic acid and 40mL of concentrated hydrochloric acid, heated to 100 ℃ and reacted for 16 hours, and then cooled to room temperature to precipitate a solid. The solid was collected and washed with water and methanol to give 10.0g of product I-3, found M/Z: 453 (M + H).
The synthesis method of the intermediate J-3 required by the formula (7-2) is as follows:
replacement of 4-chloro-1-naphthalene boronic acid in I-3 with 8-chloro-1-naphthalene boronic acid, M/Z found: 453 (M + H).
The synthesis method of the intermediate K-3 required by the formula (7-3) is as follows:
replacement of 4-chloro-1-naphthalene boronic acid in I-3 with 7-chloro-1-naphthalene boronic acid, M/Z found: 453 (M + H).
The synthesis of intermediate L-3 required by formula (7-4) is as follows:
replacement of 4-chloro-1-naphthalene boronic acid in I-3 with 6-chloro-1-naphthalene boronic acid, M/Z found: 453 (M + H).
The synthesis of intermediate M-3 required by formula (7-5) is as follows:
replacement of 4-chloro-1-naphthalene boronic acid in I-3 with 5-chloro-1-naphthalene boronic acid, M/Z found: 453 (M + H).
Synthesis examples 38 to 60 were obtained by referring to the synthesis method of the last step in synthesis example 27, and the desired intermediates and starting materials were as shown in table 4:
table 4:
device embodiments
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used under the first electrode or over the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) may be used 2 ) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, the compounds of the present invention or phthalocyanine derivative groups such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivative groups such as compounds shown below as HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may use one or more compounds of HT-1 to HT-51 described above, or use one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
The light emitting layer includes a light emitting dye (i.e., dopant) that can emit different wavelength spectrums, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of multiple different light emitting technologies may be used. These different luminescent materials, which are technically classified, may emit light of the same color, but also of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, the combination of one or more of BFD-1 through BFD-24 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light-emitting layer is selected from, but not limited to, one or more of PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
D represents deuterium.
In one aspect of the invention, the light emitting layer employs a phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of RPD-1 to RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1-YPD-11 listed below.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-73 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ、LiF、NaCl、CsF、Li 2 O、Cs 2 CO 3 BaO, na, yb, li or Ca.
The preparation process of the organic electroluminescent device in the embodiment is as follows:
example 1 use of Compounds of the invention as hole transport materials
The glass plate coated with the ITO transparent conductive layer was sonicated in a commercial cleaner, rinsed in deionized water, and dried in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cationic beam;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10 -5 Pa, performing vacuum thermal evaporation on the anode layer film to form a 10nm compound C3: HI-3 (97/3, w/w) mixture as hole injection layer, 60nm compound C3 as hole transport layer, 5nm compound HT-48 as electron blocking layer; a binary mixture of a compound pH-34 at 40nm, RPD-10 (100, w/w), as a light-emitting layer; 5nm of ET-23 as hole blocking layer, 25nm of a mixture of compounds ET-69, ET-57 (50/50, w/w) as electron transport layer, 1nm of LiF as electron injection layer, 150nm of metallic aluminum as cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
The organic electroluminescent device prepared by the above process was subjected to the following property measurements:
the driving voltage and current efficiency of the organic electroluminescent device prepared in the above manner were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 3000cd/m 2 The current voltage is the driving voltage, and the current density at the moment is measured; the ratio of the luminance to the current density is the current efficiency. The life test of LT98 is as follows: using a luminance meter at 10000cd/m 2 The luminance drop of the organic electroluminescent device was measured to be 9800cd/m with a constant current maintained at luminance 2 Time in hours.
Examples 2-26 compound C3 in example 1 was replaced with the compounds of the invention listed in table 1; comparative examples 1 to 4 Compound C3 was replaced with comparative compounds R-1, R-2, R-3, R-4 shown in Table 1, respectively.
Comparative compounds R-1 to R-4 are as follows:
R-1:(CN111662188A)
R-2:(CN101228250A)
R-3:(KR1020190118514A)
R-4:(KR1020170137976A)
table 5: the performance of the devices prepared with the compounds of the invention and the comparative compounds as hole transport materials were compared.
From the results in table 5, it can be seen that when the compound of the present invention is used as a hole transport material for a device, the current efficiency can reach 16.0cd/a or more, and at the same time, the lifetime is greatly improved, the voltage is reduced, and the compound is a hole transport material with good performance.
The compound R-1 in the comparative example 1 has a structure containing an electron-deficient fused heteroaromatic phenanthridine structure, forms a trap for hole carriers, is not beneficial to hole transmission, destroys the carrier balance of a device, and is short in efficiency and service life. The fused aromatic ring structure of the compound R-4 in comparative example 4 is much inferior to the arylamine structure in hole carrier transport mobility, and thus the device performance is seriously affected.
Compared with comparative examples 2 and 3, the compound of the invention also shows obvious performance advantages, which means that the arylamine compound has stronger carrier transport capability and is beneficial to meeting charge transport balance of devices, thereby obviously improving the voltage, the luminous efficiency and the service life of the devices.
The compounds of the present invention can also be used as electron blocking materials to complete examples 27-45, where compound C3 in example 1 was replaced with HT49 and HT-48 was replaced with the compounds shown in table 6.
Table 6: comparison of device Performance between the Compound of the present invention and the comparative Compound when used as an Electron Barrier Material
As can be seen from table 6, when the compound of the present invention is used as an electron blocking layer, the voltage, the light emitting efficiency and the device lifetime of the organic electroluminescent device prepared by using the compound of the present invention are significantly improved as compared to the device prepared by using the comparative compound.
According to the compound, the arylamine compound taking the formula (1) as a mother nucleus is introduced through a plane large conjugated structure, so that the HOMO energy level of the material is improved, and the injection of holes is facilitated, so that the working voltage of a device is reduced; the transmission capability of current carriers is improved, the luminous efficiency of the device is improved, and the service life is prolonged. Therefore, the compound is a hole transport material and an electron blocking material with good performance.
Although the present invention has been described in connection with the embodiments, the present invention is not limited to the above-described embodiments, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the present invention, and the scope of the present invention is outlined by the appended claims.
Claims (10)
1. An organic compound having a structure represented by formula (1):
in the formula (1), the reaction mixture is,
said L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group;
x is selected from S, O, siR 5 R 6 Or CR 7 R 8 ；
The R is 5 、R 6 、R 7 、R 8 Each independently selected from one of substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and the R is 7 And R 8 Are not connected with each other through chemical bonds to form a ring;
ar is 1 、Ar 2 、Ar 3 、Ar 4 Each independently selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
m and n are each independently 0 or 1, and m + n =1;
the R is 1 、R 2 、R 3 、R 4 Each independently represents hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde group, ketone group, ester group, carbonyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C1-C30 cycloalkylOr one of unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino; r is as defined above 1 、R 2 、R 3 、R 4 May each independently be fused to the aromatic ring to which it is attached;
a, b, c, d are each independently selected from 1 up to a maximum desirable integer value, a plurality of R 1 A plurality of R 2 A plurality of R 3 A plurality of R 4 Each is the same or different; when a, b, c, d are each independently an integer value greater than 1, a plurality of R' s 1 A plurality of R 2 A plurality of R 3 Or a plurality of R 4 In (b), two adjacent groups may be independently linked to each other via a chemical bond to form a ring;
when each of the above substituted or unsubstituted groups has a substituent group, the substituent group is selected from one or a combination of at least two of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde group, ketone group, ester group, carbonyl, C1-C30 chain alkyl group, C1-C30 alkoxy group, C3-C20 cycloalkyl group, C3-C20 heterocycloalkyl group, C6-C60 aryl group, and C3-C60 heteroaryl group.
2. The organic compound according to claim 1, wherein X is O or CR in formula (1) 7 R 8 。
3. The organic compound according to claim 1, having a structure represented by any one of formula (2-1), formula (2-2), or formula (2-3):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 、R 4 A, b, c, d are all as defined in formula (1).
4. The organic compound according to claim 3, wherein L is represented by formula (2-1), formula (2-2) or formula (2-3) 1 、L 2 Are all single bonds;
and/or in the formula (2-1), the formula (2-2) and the formula (2-3), a, b, c and d are all 0;
and/or, in the formula (2-1), the formula (2-2) and the formula (2-3), ar 1 、Ar 2 、Ar 3 、Ar 4 Each independently is one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; preferably, ar is 1 、Ar 2 、Ar 3 、Ar 4 Each independently selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, anthryl, phenanthryl, indenyl, anthryl, triphenylene, pyrenyl, perylenyl,
Phenyl and tetracenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl, mesityl, and biphenyl 9,9-diamylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl, furyl, thienyl, o one of a pyrrolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzofuranyl group, an indolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an acridinyl group, an isobenzofuranyl group, an isobenzothiophenyl group, an acridinyl group, a pyridyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, and a phenazinyl group;
ar mentioned above 1 、Ar 2 、Ar 3 、Ar 4 When the substituent group is contained, the substituent group is one or a combination of at least two of deuterium, halogen, chain alkyl of C1-C10, alkoxy of C1-C10, cycloalkyl of C3-C10, heterocycloalkyl of C3-C10, aryl of C6-C30 and heteroaryl of C3-C30.
5. The organic compound of claim 1, having a structure as shown in any one of formula (3-1), formula (3-2), formula (3-3), formula (3-4), or formula (3-5):
wherein L is 1 、Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 1 、R 2 、R 3 、R 4 、R 7 、R 8 A, b, c, d are all as defined in formula (1).
6. The organic compound according to claim 5, wherein L is represented by formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5) 1 Is a single bond;
and/or in the formula (3-1), the formula (3-2), the formula (3-3), the formula (3-4) or the formula (3-5), a, b, c and d are all 0;
and/or, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), ar 1 And Ar 2 Each independently is one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; preferably, ar is 1 And Ar 2 Each independently selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, anthryl, phenanthryl, indenyl, anthryl, triphenylene, pyrenyl, perylenyl,
Phenyl and tetracenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl, mesityl, and biphenyl 9,9-diamylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl, furyl, thienyl, o one of pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, and phenazinyl;
preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), said R 7 、R 8 Each independently is one of substituted or unsubstituted C1-C18 chain alkyl and substituted or unsubstituted C6-C24 aryl; more preferably, said R 7 、R 8 Each independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, anthryl, phenanthryl, indenyl, anthryl, triphenylene, pyrenyl, perylenyl,
Phenyl and tetracenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9-dimethylfluorenyl, 9-diethylfluorenyl, 9-dipropylfluorenyl, 9-dibutylfluorenyl, mesityl, and biphenyl 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl, furyl, thienyl, one of pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, and phenazinyl;
when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is one or a combination of at least two selected from deuterium, halogen, a C1-C10 chain alkyl group, a C1-C10 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group.
7. The organic compound according to claim 1, having a structure represented by any one of formula (2-1-1), formula (2-2-1), formula (2-3-1), wherein L 1 、Ar 1 、Ar 2 、L 2 、Ar 3 、Ar 4 Are as defined in formula (1):
or a structure represented by any one of formula (3-1-1), formula (3-2-1), formula (3-3-1), formula (3-4-1), formula (3-5-1), formula (3-1-2), formula (3-2-2), formula (3-3-2), formula (3-4-2) or formula (3-5-2), wherein L is 1 、Ar 1 、Ar 2 Are as defined in formula (1):
8. the organic compound according to claim 1, having the structure shown below:
9. use of the organic compound according to any one of claims 1 to 8 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
preferably, the organic compound is applied as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 8 therein;
preferably, the light emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, and the hole transport layer or the electron blocking layer contains the organic compound according to any one of claims 1 to 8.
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