CN115340464A - 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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- CN115340464A CN115340464A CN202110513932.6A CN202110513932A CN115340464A CN 115340464 A CN115340464 A CN 115340464A CN 202110513932 A CN202110513932 A CN 202110513932A CN 115340464 A CN115340464 A CN 115340464A
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- heteroaryl
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 47
- 239000010410 layer Substances 0.000 claims description 84
- -1 nitro, hydroxyl Chemical group 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 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 9
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 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
- 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
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 114
- 230000015572 biosynthetic process Effects 0.000 description 44
- 238000003786 synthesis reaction Methods 0.000 description 44
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 13
- 239000011368 organic material Substances 0.000 description 11
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001769 aryl amino group Chemical group 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 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 4
- 238000009825 accumulation Methods 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical class C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- AVJBQMXODCVJCJ-UHFFFAOYSA-M 1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium;chloride Chemical compound [Cl-].CC(C)C1=CC=CC(C(C)C)=C1N1C=[N+](C=2C(=CC=CC=2C(C)C)C(C)C)C=C1 AVJBQMXODCVJCJ-UHFFFAOYSA-M 0.000 description 1
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 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
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000001301 oxygen Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—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
- 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
- C07D209/88—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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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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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 I. When the compound is applied to an organic electroluminescent device, the working voltage of the device can be effectively reduced,and simultaneously, the efficiency of the device is 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 become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and crunchy optoelectronic products, with unparalleled advantages over inorganic materials. 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 are particularly rapidly developed and have been commercially successful in the field of information displays. The OLED can provide three colors of red, green and blue 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 colorful, light, thin and soft color and the like.
The core of the OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, to generate excitons and emit light.
People have developed various organic materials, and the organic materials are combined with various peculiar device structures, so that the carrier mobility can be improved, the carrier balance can be regulated, the electroluminescent efficiency can be broken through, and the attenuation of the device can be delayed. For quantum mechanical reasons, common fluorescent emitters mainly utilize singlet excitons generated when electrons and holes are combined to emit light, and are still widely applied to 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-like materials.
As OLED products gradually enter the market, there are increasingly higher requirements on the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, service life, cost and the like.
Therefore, the development of an organic electroluminescent material capable of improving the luminous efficiency of the device, reducing the driving voltage and prolonging the service life is urgently needed in the art.
Disclosure of Invention
The invention aims to provide a compound, in particular to an organic electroluminescent material, and particularly to an electron barrier material, wherein the compound is applied to an organic electroluminescent device, can improve the luminous efficiency of the device, reduces the driving voltage, and can be used as a red electron barrier material.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I;
in formula I:
L、L 1 and L 2 Each independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;
Ar 1 one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
x is CR 1 R 2 Or SiR 3 R 4 Said R is 1 、R 2 、R 3 And R 4 Each independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and the R 1 And R 2 Can be connected into a ring, the R 3 And R 4 Can be connected into a ring;
X 1 ～X 11 are each independently selected from CR 5 Or N, said R 5 Selected from hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, and substituted or unsubstituted C1-C20 siliconOne of alkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 5 Independently with the attached aromatic or heteroaromatic ring to form a ring or not;
X 12 ～X 19 each independently selected from C and CR 6 Or N, said R 6 One selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 6 Independently with the linked aromatic or heteroaromatic ring to form a ring or not;
when the above groups have a substituent, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, C6-C60 aryl and C3-C60 heteroaryl.
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 indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present invention, unless otherwise specified, the expression of chemical elements generally includesThe concept of isotopes thereof, such as the expression "hydrogen (H)", includes isotopes thereof 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 present invention generally means an atom or an atomic group selected from N, O, S, P, si and Se, and 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, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings.
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 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from a 1-pyrenyl group, a 2-pyrenyl group and a 4-pyrenyl group; 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 and 9,9Dipropylfluorenyl group, 9-dibutylfluorenyl group, 9-dipentylfluorenyl group, 9-dihexylfluorenyl group 9,9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
The C3 to C60 heteroaryl group mentioned in the present invention 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 the fused heteroaryl group include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, 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. The number of carbons in the arylene group includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, and the like. 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.
In the present invention, arylamino represents a group formed by substituting one or two aryl groups for hydrogen on an amino group, wherein the linking site of the arylamino group may be linked to an aryl group in the arylamino group or to N in the arylamino group, and exemplary carbon numbers and specific groups of the aryl group in the arylamino group are the same as described above.
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. Examples of the substituted or unsubstituted C1-C10 chain alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl and the like.
In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single cyclic structure; polycyclic alkyl refers to a structure in which two or more cycloalkyl groups share one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and the like.
In the present specification, examples of the substituted or unsubstituted C1-C20 alkoxy group, preferably the substituted or unsubstituted C1-C10 alkoxy group, and the C1-C10 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutyloxy, isopentyloxy, more preferably methoxy, are preferred.
In the present specification, examples of the substituted or unsubstituted C1-C20 silane group, the substituted or unsubstituted C1-C10 silane group and the C1-C10 silane group include a silyl group substituted with the groups exemplified for the above-mentioned C1-C10 alkyl groups, and specific examples thereof include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and the like.
Further, in formula I, L is preferably a single bond; and/or, said L 1 Preferably a single bond; and/or, said L 2 Preferably a single bond.
Further, in the formula I, L is 2 Is connected to X 12 The position of (a); or, said L 2 Is connected to X 13 The position of (a); or, said L 2 Is connected to X 14 The position of (a); or, said L 2 Is connected to X 15 The position of (a).
Further, in the formula I, X is 1 ～X 11 Each independently selected from CR 5 Said R is 5 Independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and the R is 5 Independently with the attached aromatic or heteroaromatic ring to form a ring or not; 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, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 3 to 30 carbon atoms.
More preferably, X is 1 ～X 11 Independently selected from CR 5 Said R is 5 Is hydrogen.
Further, in the formula I, X is 12 ～X 19 Independently selected from C or CR 6 Said R is 6 Independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substitutedOr one of unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 6 Independently with the linked aromatic or heteroaromatic ring to form a ring or not; 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, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 3 to 30 carbon atoms. In particular, when X 12 ～X 19 And when any one of them is C, it represents the position to which N in formula I is bonded.
More preferably, X 12 ～X 19 Independently selected from C or CR 6 Said R is 6 Is hydrogen.
Further, in the formula I, R is 1 、R 2 、R 3 And R 4 Each independently selected from the group consisting of substituted or unsubstituted: 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, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
One of a phenyl group, a tetracenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diethylfluorenyl group, a 9, 9-dipropylfluorenyl group, a 9, 9-dibutylfluorenyl group, a 9, 9-dipentylfluorenyl 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, and said R is 1 And R 2 Can be connected with each other to form a ring, the R 3 And R 4 Can be connected into a ring; when each of the above-mentioned substituted or unsubstituted groups has a substituent group, the substituent group is selected fromDeuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl or at least two combinations;
still further preferably, said R 1 、R 2 、R 3 And R 4 Each independently selected from methyl, phenyl or one of the following substituent groups:
still further preferably, said R 1 、R 2 、R 3 And R 4 Each independently selected from methyl and phenyl.
Further, in formula I, X is CR 1 R 2 Or SiR 3 R 4 And said R is 1 And R 2 When they are connected to form a ring, or R is 3 And R 4 When connected to form a ring, X has one of the following structural formulas:
wherein the dotted line represents the bond of X.
Further, in formula I, ar 1 Selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthryl, phenanthryl, indenyl, anthryl, triphenylene, pyrenyl, perylenyl,
<xnotran> , 2- ,3- ,4- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- ,9,9- , , , , , , , , , , , , </xnotran>One of a phenyl group, an isobenzofuranyl group, an isobenzothienyl group, an acridinyl group, a pyridyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, and a phenazinyl group;
when each of the above substituted or unsubstituted groups has a substituent group, it is preferable that 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, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms;
preferably, said Ar 1 Selected from the group consisting of substituted or unsubstituted structural groups, wherein the dashed line represents a connecting bond:
when each structural group has a substituent group, the substituent group is one or a combination of at least two selected from deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
The invention provides a novel organic electroluminescent material, which utilizes the coordination of dibenzofluorene derivatives or heterocyclic compounds of silicon and tri-stacked alkene substituted by amino on 2-position to obtain an electronic barrier material with better space structure and better film accumulation form.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Further, the compounds of the general formula of the present invention are preferably the following specific compounds, but the present invention is not limited to the specific compounds P1 to P390 shown below:
the second purpose of the invention is to provide the application of the compound in the first purpose, and the compound is applied to an organic electroluminescent device, and is preferably used as an electron barrier material of the organic electroluminescent device.
When the compound is used as an electron barrier layer material of an organic electroluminescent device, the compound can effectively improve the luminous efficiency and reduce the driving voltage, and is particularly suitable to be used as a red light electron barrier layer material.
It is a third object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer provided between the first electrode and the second electrode, the organic layer containing a compound according to one of the objects;
preferably, the organic layer includes an electron blocking layer containing the compound according to one of the objects.
The compound of the invention can be applied to organic electroluminescent devices, and can also be applied to other types of organic electronic devices, including organic field effect transistors, organic thin-film solar cells, information labels, electronic artificial skin sheets, sheet type scanners or electronic paper.
Specifically, another technical scheme of the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer which are sequentially formed on the substrate; the light-emitting functional layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer and an electron transport layer, wherein the electron blocking layer contains at least one of the compounds.
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. Further, 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 serving 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 ) Oxide transparent conductive 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 have 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) using the compound of formula I according to the present invention.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate)
(PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives including 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 employ one or more compounds of HT-1 to HT-51 described above, or employ one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HI-1 to HI-3 described below may also be doped with one or more compounds HT-1 to HT-51.
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 a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, combinations of one or more of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technology. 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 a 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.
Wherein D is 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 to 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 material 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.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a novel organic electroluminescent material, which utilizes the coordination of a dibenzofluorene derivative or a heterocyclic compound of silicon and a triplet alkene substituted by amino on 2-position, can obtain an electronic barrier material with better space structure and better film accumulation form through reasonable structure adjustment, can further improve the luminous efficiency of a device when being used for an organic light-emitting device, and has obvious effects of improving voltage and improving luminous efficiency compared with the compounds in the prior art.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitation of the present invention.
A representative synthetic route for the compounds of formula I of the present invention is as follows:
wherein Ar is 1 、L、L 1 、X、X 1 -X 19 Are all the same as the symbols in formula I; pd 2 (dba) 3 Represents tris (dibenzylacetone) dipalladium (0), IPr. HCl represents 1, 3-bis (2, 6-diisopropylphenyl) imidazolium chloride, naOBu-t represents sodium tert-butoxide, (t-Bu) 3 P represents tri-tert-butylphosphine. The preparation of the compound of formula I of the present invention includes the above-mentioned methods, but is not limited to the above-mentioned methods, and the compound of formula I synthesized by other methods by those skilled in the art also belongs to the protection scope of the present invention.
More specifically, the following synthesis examples of the present invention exemplarily provide specific synthetic methods of representative compounds, and the solvents and reagents used in the following synthesis examples can be purchased or customized from domestic chemical product markets. In addition, they can be synthesized by a known method by those skilled in the art.
Synthesis example 1: synthesis of Compound P6
In a 1000mL single-necked flask, 13.5g of M1 and 13.5g of 2-bromo-9, 9-dimethylfluorene were added0.5g of tris (dibenzylideneacetone) dipalladium (i.e., pd) 2 (dba) 3 ) 0.5g of IPr. HCl,300mL of toluene, 15g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, filtering an organic phase through a silica gel column twice, concentrating the organic phase, adding methanol, refluxing and stirring for 1 hour, performing suction filtration to obtain light yellow powder M1-1, and recrystallizing twice with ethyl acetate to obtain a pure product.
In a 1000mL three-necked flask, 23g of M1-1, 11.5g of 4-bromobiphenyl, and 0.5g of tris (dibenzylideneacetone) dipalladium (i.e., pd) were added 2 (dba) 3 ) 0.5mL of tri-tert-butylphosphine ((t-Bu) 3 P), 300mL of toluene and 15g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, filtering the organic phase through silica gel columns twice to remove inorganic matters, concentrating the organic phase, adding methanol, refluxing and stirring for 1h, performing suction filtration to obtain light yellow powder P6, and recrystallizing the obtained solid with ethyl acetate to obtain a pure product. M/Z theoretical value: 613; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 614.
synthesis example 2: synthesis of Compound P12
The compound M1-2 was synthesized in the same manner as the compound M1-1 except that 2-bromo-9, 9-dimethylfluorene was replaced with 4-bromo-9, 9-dimethylfluorene; the compound P12 is synthesized by the same method as the compound P6 except that 4-bromobiphenyl is replaced by 2-bromobiphenyl and the intermediate M1-1 is replaced by the intermediate M1-2.M/Z theoretical value: 613; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 614.
synthesis example 3: synthesis of Compound P18
The compound P18 is synthesized by the same method as the compound P6 except that 4-bromobiphenyl is replaced by 4-bromoterphenyl. M/Z theoretical value: 689; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 690.
synthesis example 4: synthesis of Compound P30
Compound P30 was synthesized in the same manner as for the synthesis of compound P6 except that 4-bromobiphenyl was changed to B1.M/Z theoretical value: 765 (b) mixing; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 766.
synthesis example 5: synthesis of Compound P54
Compound P54 was synthesized in the same manner as for the synthesis of compound P6 except that 4-bromobiphenyl was changed to B2.M/Z theoretical value: 689; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 690.
synthesis example 6: synthesis of Compound P70
The compound M1-3 is synthesized by the same method of synthesizing the compound M1-1, except that 2-bromo-9, 9-dimethylfluorene is replaced by 2-bromo-9-phenyl-9-methylfluorene; compound P70 was also synthesized by the method for synthesizing compound P6. M/Z theoretical value: 675; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 676.
synthesis example 7: synthesis of Compound P130
The compound M1-4 is synthesized by the same method as the compound M1-1 except that 2-bromo-9, 9-dimethylfluorene is replaced by 2-bromo-9, 9-diphenylfluorene; compound P130 was synthesized in the same manner as compound P6 except that 4-bromobiphenyl was replaced by bromobenzene and intermediate M1-1 was replaced by intermediate M1-4.M/Z theoretical value: 661; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 662.
synthesis example 8: synthesis of Compound P198
The compound M1-5 is synthesized by the same method of synthesizing the compound M1-1, except that 2-bromo-9, 9-dimethylfluorene is replaced by B3; compound P198 was synthesized in the same manner as compound P6 except that intermediate M1-1 was replaced with intermediate M1-5.M/Z theoretical value: 629; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 630.
synthesis example 9: synthesis of Compound P268
The compound M1-6 was synthesized in the same manner as in the synthesis of the compound M1-1 except that 2-bromo-9, 9-dimethylfluorene was replaced with B4; compound P268 was synthesized in the same manner as compound P6 except that 4-bromobiphenyl was changed to 2-bromobiphenyl and intermediate M1-1 was changed to intermediate M1-6.M/Z theoretical value: 691; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 692.
synthesis example 10: synthesis of Compound P2
Compound P2 was synthesized in the same manner as compound P6 except that 4-bromobiphenyl was replaced by bromobenzene. M/Z theoretical value: 537; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 538.
synthesis example 11: synthesis of Compound P7
The compound M1-7 was synthesized in the same manner as in the synthesis of the compound M1-1 except that 2-bromo-9, 9-dimethylfluorene was replaced with 3-bromo-9, 9-dimethylfluorene; the compound P7 was synthesized in the same manner as the compound P6 except that the intermediate M1-1 was replaced by the intermediate M1-7.M/Z theoretical value: 613; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 614.
synthesis example 12: synthesis of Compound P385
The compound M2-1 is synthesized by the same method as the compound M1-1 except that M1 is replaced by M2; compound P385 was also synthesized by the method for synthesizing compound P6, except that intermediate M1-1 was replaced by intermediate M2-1.M/Z theoretical value: 613; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 614.
synthesis example 13: synthesis of compound P386
The compound M1-2 was synthesized in the same manner as in the synthesis of the compound M1-1 except that 2-bromo-9, 9-dimethylfluorene was replaced with A1; compound P386 was synthesized in the same manner as compound P6 except that 4-bromobiphenyl was replaced by bromobenzene and intermediate M1-1 was replaced by intermediate M1-8.M/Z theoretical value: 613; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 614.
synthesis example 14: synthesis of Compound P387
Compound P387 was synthesized in the same manner as for the synthesis of compound P6, except that 4-bromobiphenyl was replaced by 3-bromobenzofuran. M/Z theoretical value: 627; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 628.
synthesis example 15: synthesis of Compound P388
Compound P388 was synthesized in the same manner as compound P6 except that 4-bromobiphenyl was replaced by 2-bromo-9-phenylcarbazole. M/Z theoretical value: 702; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 703.
synthesis example 16: synthesis of Compound P389
The compound M3-1 is synthesized by the same method as the compound M1-1 except that M1 is replaced by M3; compound P389 was synthesized in the same manner as for compound P6 except that 4-bromobiphenyl was changed to bromobenzene and intermediate M1-1 was changed to intermediate M3-1.M/Z theoretical value: 593; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z found: 594.
synthesis example 17: synthesis of Compound P390
The compound M1-9 was synthesized in the same manner as in the synthesis of the compound M1-1 except that 2-bromo-9, 9-dimethylfluorene was replaced with A2; the compound P390 is synthesized by the synthesis method of the compound P6, except that 4-bromobiphenyl is replaced by bromobenzene, and the intermediate M1-1 is replaced by the intermediate M1-9.M/Z theoretical value: 629; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 630.
example 1
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 1 × 10 -5 Pa, performing vacuum evaporation on the anode layer film to obtain a mixture of HT-4 HI-3 (97/3, w/w) as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 60nm;
vacuum evaporating P2 on the hole-hole transport layer to serve as an electron blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35nm;
a light-emitting layer of the device is evaporated in vacuum on the hole transport layer, the light-emitting layer comprises a host material and a dye material, a ternary mixture of PH-61, PH-3;
vacuum evaporation is carried out on the electron transport layer material ET-69 (50/50, w/w) mixture of the device on the light-emitting layer, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 25nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Examples 2 to 17 and comparative examples 1 to 3 provided organic electroluminescent devices that were fabricated in the same manner as in example 1 except that the compound P2 as an electron blocking layer material was replaced with the compounds shown in table 1, respectively.
The structures of the electron barrier materials of comparative examples 1 to 3 are as follows:
synthesis of comparative Compounds R-1, R-2, R-3: specific methods refer to the synthesis methods in patent documents CN1479561A, CN107108499A and CN102203213A, and the description thereof is omitted here.
And (4) performance testing:
the organic electroluminescent devices prepared by the above processes were subjected to the following performance measurements of the current efficiencies of the organic electroluminescent devices prepared in the above examples and comparative examples. 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 10000cd/m 2 Then, the ratio of the brightness to the current density at this time was measured as the current efficiency, and the test results are shown in table 1.
TABLE 1
As can be seen from the data in Table 1, when the compound of the present invention is used as an electron blocking layer material of an organic electroluminescent device, the luminance of the device reaches 10000cd/m 2 When the voltage is low to 4.1, the current efficiency is as high as more than 58.5cd/A, the voltage of the device can be effectively reduced, the current efficiency can be improved, and the material is an electron barrier layer material with good performance.
In summary, compared with the prior art, the present invention utilizes the dibenzofluorene derivative or the heterocyclic compound of silicon to cooperate with the triplet substituted by the amino group at the 2-position, so as to obtain the electronic blocking material with better space structure and better film accumulation form.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An organic compound having the structure shown in formula i:
in formula I:
L、L 1 and L 2 Each independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;
Ar 1 one selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
x is CR 1 R 2 Or SiR 3 R 4 Said R is 1 、R 2 、R 3 And R 4 Each independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and the R 1 And R 2 Can be connected with each other to form a ring, the R 3 And R 4 Can be connected into a ring;
X 1 ～X 11 are each independently selected from CR 5 Or N, said R 5 One selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 5 Independently of each otherThe connected aromatic ring or heteroaromatic ring is connected to form a ring or is not connected to form a ring;
X 12 ～X 19 each independently selected from C and CR 6 Or N, said R 6 One selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 6 Independently with the linked aromatic or heteroaromatic ring to form a ring or not;
when the above groups have a substituent, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, C6-C60 aryl and C3-C60 heteroaryl.
2. The organic compound according to claim 1, wherein in formula I, L is a single bond;
and/or, said L 1 Is a single bond;
and/or, said L 2 Is a single bond;
preferably, in formula I, L is 2 Is connected to X 12 The position of (a);
or, said L 2 Is connected to X 13 The position of (a);
or, said L 2 Is connected to X 14 The position of (a);
or, said L 2 Is connected to X 15 The position of (a).
3. The organic compound according to claim 1, formula I wherein X 1 ～X 11 Each independently selected from CR 5 Said R is 5 Independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstitutedOne of substituted C3-C60 heteroaryl, said R 5 Independently with the attached aromatic or heteroaromatic ring to form a ring or not;
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 C6-C30 aryl group, and a C3-C30 heteroaryl group;
preferably, X is 1 ～X 11 Independently selected from CR 5 Said R is 5 Is hydrogen.
4. The organic compound according to claim 1, formula I wherein X 12 ～X 19 Independently selected from C or CR 6 Said R is 6 Independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 6 Independently with the attached aromatic or heteroaromatic ring to form a ring or not;
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 of C1 to C10, an alkoxy group of C1 to C10, a cycloalkyl group of C3 to C10, an aryl group of C6 to C30, and a heteroaryl group of C3 to C30;
preferably, X 12 ～X 19 Independently selected from C or CR 6 Said R is 6 Is hydrogen.
5. The organic compound according to claim 1, wherein R is 1 、R 2 、R 3 And R 4 Each independently selected from the group consisting of substituted or unsubstituted: 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, pyreneA perylene group,
One of a phenyl group, a tetracenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diethylfluorenyl group, a 9, 9-dipropylfluorenyl group, a 9, 9-dibutylfluorenyl group, a 9, 9-dipentylfluorenyl 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, and said R is 1 And R 2 Can be connected into a ring, the R 3 And R 4 Can be connected into a ring;
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 C6-C30 aryl group, and a C3-C30 heteroaryl group;
preferably, said R is 1 、R 2 、R 3 And R 4 Each independently selected from methyl, phenyl or one of the following substituent groups:
more preferably, R is 1 、R 2 、R 3 And R 4 Each independently selected from methyl and phenyl.
6. The organic compound according to claim 1, wherein X is CR 1 R 2 Or SiR 3 R 4 And said R is 1 And R 2 When they are connected to form a ring, or R is 3 And R 4 When the two are connected to form a ring, X is shown in the following structural formulaOne of (1):
wherein the dotted line represents the bond of X.
7. The organic compound according to claim 1, formula I, wherein Ar is 1 Selected from the following substituted or unsubstituted 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; 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 of C1 to C10, an alkoxy group of C1 to C10, a cycloalkyl group of C3 to C10, an aryl group of C6 to C30, and a heteroaryl group of C3 to C30;
preferably, ar is 1 Selected from the group consisting of substituted or unsubstituted structural groups wherein the dashed line represents a connecting bond:
when each structural group has a substituent group, the substituent group is one or a combination of at least two of deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
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 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 electron blocking layer contains the organic compound according to any one of claims 1 to 8.
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