CN116023399A - Organic compound for light-emitting device, application of organic compound and organic electroluminescent device - Google Patents
Organic compound for light-emitting device, application of organic compound and organic electroluminescent device Download PDFInfo
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- CN116023399A CN116023399A CN202111233848.5A CN202111233848A CN116023399A CN 116023399 A CN116023399 A CN 116023399A CN 202111233848 A CN202111233848 A CN 202111233848A CN 116023399 A CN116023399 A CN 116023399A
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- heteroaryl
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 229910052796 boron Inorganic materials 0.000 claims abstract description 25
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 23
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 170
- 239000000463 material Substances 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 230000003111 delayed effect Effects 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 77
- 238000003786 synthesis reaction Methods 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- 239000011368 organic material Substances 0.000 description 13
- 230000000903 blocking effect Effects 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 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 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 9
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000001725 pyrenyl group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 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 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 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 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 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 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 150000001793 charged compounds Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000001046 green dye Substances 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000001044 red dye Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000007725 thermal activation Methods 0.000 description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Chemical group 0.000 description 2
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- 230000005540 biological transmission Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 150000004844 dioxiranes Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
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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
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic 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
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 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 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
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 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
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 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
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a boron-containing organic compound, which is characterized by having a structure shown in a formula (1):
Description
Technical Field
The invention relates to a compound for an organic electronic device, in particular to a double-B-N structure organic photoelectric material taking benzene rings as basic frameworks. The invention also relates to application of the material in an organic electroluminescent device.
Background
The main way people acquire information is through vision, so that a display device is important in the process of human interaction with information. Organic Light Emitting Diodes (OLEDs) have many advantages of flexibility, self-luminescence, high contrast, large size, low power consumption, etc., and become one of the currently mainstream display devices.
Currently, optoelectronic devices employing organic materials are becoming increasingly popular. Most materials used to make such devices are more cost effective (organic materials are inexpensive) than inorganic devices. At present, in the structure of an organic electroluminescent device in the field of display and illumination, blue fluorescence is generally adopted to match red and green phosphorescence materials. The red dye and the green dye which are three primary colors can theoretically realize 100% of internal quantum efficiency due to the fact that the red dye and the green dye generally contain heavy atoms such as Ir, pt and the like, and are high in electroluminescent efficiency and low in power consumption, so that the red dye and the green dye become the main stream of the current commercial display equipment. However, the chromaticity and lifetime of blue phosphorescent materials are not as good as the current commercial display requirements. Currently, blue light devices still employ conventional fluorescent materials to achieve high color purity and long device lifetime.
Recently, researchers such as Takuji Hatakeyama and Junji Kido in japan report a series of organic materials DABNA-1 (adv. Mater.2016,28,2777-2781j. Mater. Chem. C,2019,7, 3082-3089) based on TADF (Thermally Activated Delayed Fluorescence ) containing boron resonance, boron atoms, nitrogen atoms and phenyl groups of the compounds constitute a rigid polycyclic aromatic skeleton, and thus have high fluorescence quantum yield. Compared with the traditional blue fluorescent dye, the compound has narrower spectrum and better color purity. However, when such compounds are applied as dyes to devices, the lifetime of the devices is short and the detrimental consequences of spectral broadening and red shifting are likely to occur.
There is still a great room for improvement in the light emitting performance of the existing organic electroluminescent materials, and there is a need in the industry to develop new luminescent material systems to meet the commercial demands. Boron-containing resonant materials have the advantages of high color purity and high luminous efficiency, and are attracting wide attention in the scientific research and industry. However, the light color of the material is limited to the blue light-deep blue light area because the light color of the material is difficult to regulate, and the further application of the material in the fields of high-resolution display, full-color display, white light illumination and the like is greatly limited.
Disclosure of Invention
In order to solve the technical problems, the invention provides a boron-containing organic compound, which is characterized in that the boron-containing organic compound has a structure shown in a formula (1):
in the formula (1), the ring A, the ring D and the ring E are respectively one of C6-C60 aromatic rings and C3-C60 heteroaromatic rings independently;
R a 、R b each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said R a 、R b Each of which may be independently linked to each other by a chemical bond to form a ring; m and n are integers from 0 to the maximum allowable;
X 1 、X 2 each independently selected from O, S, CR 1 R 2 、NR 3 ；
X 3 、X 4 Each independently selected from halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 hetero One of arylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
R 1 、R 2 、R 3 each independently selected from one of hydrogen, halogen, carboxyl, nitro, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 thioalkoxy, amino, alkyl substituted amino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl;
the R is 1 、R 2 、R 3 The ring D and the ring E can be connected with each other through chemical bonds to form a ring;
g is an electron-withdrawing group which is a group,
the "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, and C3-C60 heteroarylamino.
In a preferred embodiment, at least one of the rings D and E in the formula (1) of the present invention is one selected from benzene rings and six-membered heteroaromatic rings, and the ring a is one selected from benzene rings and six-membered heteroaromatic rings.
Minlang Yang, university of Kyushu, in the literature Full-Color, narrowband, and High-Efficiency Electroluminescence from Boron and Carbazole Embedded Polycyclic Heteroaromatics (J.Am. Chem. Soc.2020,142, P19468-P19472) discloses organic light-emitting compounds that appropriately control the red shift of light Color,
however, when the present inventors tried to use the compound in a light-emitting device, the lifetime of the compound as a light-emitting dye was short, and the voltage of the device was high, making the practical use very difficult, and as an organic electroluminescent material, there was a great room for improvement in light-emitting performance, and in particular, improvement in the excitation voltage and lifetime thereof was desired.
The inventor discovers that in the boron-containing organic compound similar to the formula (1), a D ring, an E ring and an A ring are connected with a B atom to form a larger conjugated system, an electron cloud resonates in a larger range and has similar performance to a boron-containing resonant material DABA-1, an aromatic ring is coordinated with the B atom to be aligned and connected with an electron withdrawing group, and on the premise of keeping multiple resonances, effective red shift is generated through energy level splitting of a front line orbit, so that a target molecule has high luminous efficiency and high color purity. The series of materials can obtain red light to near infrared emission.
In particular, the present inventors have found that if an electron withdrawing group is introduced at a position para to the boron atom of the a ring, the lifetime of a device using such a compound can be greatly improved, and the reason for this is not clear, and it is presumed that the electron withdrawing group (G group of the present invention) can make the electrical distribution of such a molecule itself more stable, so that the chemical characteristics become milder and oxidation or the like is less likely to occur.
Meanwhile, the inventor also discovers that the adjacent position of the electron withdrawing group G is provided with a substituted steric hindrance group which is not H, which is beneficial to improving the thermal activation delay property of the B-containing resonance type material and improving the efficiency of the device.
The molecular design of the invention also greatly improves the service life of the device.
The electron withdrawing group G is a group having an electron withdrawing inducing effect on the aromatic ring, that is, a group having a reduced electron cloud density on the aromatic ring after the group has replaced hydrogen on the aromatic ring, and examples of the electron withdrawing group include: halogen atom, nitro group, cyano group, trihalomethyl group, triazinyl group, pyrimidinyl group, benzopyrimidinyl group, benzopyridyl group, naphthyridinyl group, phenanthroline group, pyrazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, pyridazinyl group and the like, however, the electron withdrawing group G in the present invention is not limited to the above-mentioned groups, and generally, a hammett value of more than 0.6 can achieve the technical effect of the present invention. The Hammett value refers to the characterization of the charge affinity for a particular group, and is a measure of the electron withdrawing group (positive Hammett value) or the electron donating group (negative Hammett value). Hammett's equation is described in more detail in Thomas H.Lowry and KatheleenSchueller Richardson, "Mechanism and Theory In Organic Chemistry', new York,1987, pages 143-151, which is incorporated herein by reference. Preferred electron withdrawing groups G in the present invention will be described in detail hereinafter.
It should be noted that unless otherwise defined below, all technical and scientific terms used herein are intended to have the same meaning as commonly understood by one of ordinary skill in the art. References to techniques used herein are intended to refer to techniques commonly understood in the art, including variations of those that are obvious to those skilled in the art or alternatives to equivalent techniques. While the following terms are believed to be well understood by those skilled in the art, the following definitions are set forth to better explain the present invention.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent. When C1-30 is described, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.
The terms "comprising," "including," "having," "containing," or "involving," and other variations thereof herein, are inclusive or open-ended and do not exclude additional unrecited elements or method steps.
In the present invention, unless otherwise specified, the expression of chemical elements generally includes the concept of isotopes of the same chemical nature, for example, the expression of "hydrogen" also includes the concept of "deuterium", "tritium" of the same chemical nature, and carbon (C) includes 12 C、 13 C, etc., and are not described in detail.
Heteroatoms in the present invention are generally selected from N, O, S, P, si and Se, preferably from N, O, S.
As used herein, the terms "heterocyclyl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and/or triple bonds within the ring) cyclic group having at least one ring atom that is a heteroatom selected from N, O and S and the remaining ring atoms that are C.
As used herein, the terms "(arylene) and" aromatic ring "refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated pi-electron system. As used herein, the terms "(arylene) heteroaryl" and "heteroaryl ring" refer to a monocyclic, bicyclic, or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably denotes aryl or heteroaryl substituted alkyl, wherein the aryl, heteroaryl and alkyl are as defined herein.
As used herein, the term "halo" or "halogen" group is defined to include F, cl, br or I.
The term "substitution" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution forms a stable compound. Combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.
If substituents are described as "independently selected from" a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another substituent(s).
The term "one or more" as used herein means 1 or more than 1, such as 2, 3, 4, 5 or 10, under reasonable conditions.
As used herein, unless indicated, the point of attachment of a substituent may be from any suitable position of the substituent.
When the bond of a substituent is shown as a bond through the ring connecting two atoms, then such substituent may be bonded to any ring-forming atom in the substitutable ring.
Those skilled in the art will appreciate that not all nitrogen-containing heterocycles are capable of forming N-oxides, as nitrogen requires available lone pairs to oxidize to oxides; those skilled in the art will recognize nitrogen-containing heterocycles capable of forming N-oxides. Those skilled in the art will also recognize that tertiary amines are capable of forming N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are well known to those skilled in the art and include oxidizing heterocycles and tertiary amines with peroxyacids such as peracetic acid and m-chloroperoxybenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes (dioxiranes) such as dimethyl dioxirane. These processes for the preparation of N-oxides have been described and reviewed extensively in the literature, see for example: T.L. Gilchrist, comprehensive Organic Synthesis, vol.7, pp 748-750; katritzky and a.j. Boulton, eds., academic Press; and G.W.H.Cheeseman and E.S.G.Werstiuk, advances in Heterocyclic Chemistry, vol.22, pp 390-392, A.R.Katritzky and A.J.Boulton, eds., academic Press.
The invention also encompasses compounds of the invention containing a protecting group. During any process for preparing the compounds of the present invention, it may be necessary and/or desirable to protect sensitive or reactive groups on any of the molecules of interest, thereby forming a chemically protected form of the compounds of the present invention. This can be achieved by conventional protecting groups, for example those described in T.W.Greene & P.G.M.Wuts, protective Groups in Organic Synthesis, john Wiley & Sons,1991, which are incorporated herein by reference. The protecting group may be removed at a suitable subsequent stage using methods known in the art.
The term "about" means within + -10%, preferably within + -5%, more preferably within + -2% of the stated value.
In the structural formulae disclosed in the present specification, the expression of the ring structure "to which" - "is drawn indicates that the linking site is located at any position on the ring structure that can be bonded.
The above-mentioned C6 to C60 aromatic ring and C3 to C60 heteroaromatic ring in the present invention are aromatic groups satisfying pi conjugated system, and include both cases of monocyclic residues and condensed ring residues unless otherwise specified. By monocyclic residue is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenyl, terphenyl, and the like; condensed ring residues refer to molecules containing at least two benzene rings, but the benzene rings are not independent of each other, but share the ring edges and are condensed with each other, such as naphthyl, anthryl, phenanthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are connected by a single bond, such as pyridine, furan, thiophene, etc.; condensed ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl rings, such as, for example, quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like
In the present specification, the substituted or unsubstituted C6 to C60 aromatic ring is preferably a C6 to C30 aromatic ring, more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthryl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl 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 naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl groupA base; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. Preferred examples of the aromatic ring in the present invention include a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, 
A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises 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 naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl.
In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, more preferably a group selected from the group consisting of phenyl, naphthyl, anthryl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylenyl, fluoranthenyl, naphthacene, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimeriindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl 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 naphthyl comprises 1-naphthyl or 2-naphthyl; the anthryl group is selected from 1-anthryl group, 2-anthryl group and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. As preferable examples of the aryl group in the present invention, there may be mentioned a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,
A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises 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 naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The C6-C60 aryl group of the present invention may be a group in which the above groups are bonded by single bonds or/and condensed.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl ring is preferably a C3 to C30 heteroaryl ring, and may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: from furyl, thienyl, pyrrolyl, pyridinyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthyridinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenozolyl, phenanthroozolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, heteroaromatic rings formed by 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like. As preferable examples of the heteroaromatic ring in the present invention, for example, a heteroaromatic ring of furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothiazyl, carbazolyl and derivatives thereof are mentioned, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbozolebocarbazole, dibenzocarbazole or indolocarbazole.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a C3 to C30 heteroaryl group, more preferably an aza-containing heteroaryl group, an oxy-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridinyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenozolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like. As preferable examples of the heteroaryl group in the present invention, for example, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof are mentioned, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbozole or indolocarbazole. The C3-C60 heteroaryl groups of the present invention may also be those wherein the above groups are joined singly or in combination by fusion.
In the present specification, alkyl also includes the concept of cycloalkyl. Examples of the C1-C20 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl and the like.
In the present specification, cycloalkyl includes monocycloalkyl and multicycloalkyl, and may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
In the present specification, examples of the C1 to C20 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 are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, examples of the C1-C20 silyl group include silyl groups substituted with the groups exemplified for the C1-C20 alkyl groups described above, and specific examples include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and the like.
In the present specification, examples of the aryloxy group of C6 to C60 include those in which each group of the substituted or unsubstituted C6 to C60 aryl group is bonded to oxygen, and specific examples thereof are described with reference to the above examples and are not described here.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, the term "C6-C60 arylamino" or "C3-C60 heteroarylamino" means amino-NH 2 One or two H's are substituted by the above-exemplified C6-C60 aryl or C3-C60 heteroaryl groups.
As a preferred embodiment of the present invention, the formula (1) is preferably a structure represented by the formula (2),
in the formula (2), the Z 1 、Z 2 、Z 3 And Z 4 Are independently selected from CR 4 Or N, the R 4 Is one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R is 4 Each of which may be independently linked to each other by a chemical bond to form a ring;
R 4 The "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, C3-C60 heteroarylamino, X 1 、X 2 、X 3 、X 4 G has the same meaning as that of the above.
As a preferred embodiment of the present invention, G is one selected from the group consisting of F, cyano, trifluoromethyl and the following aromatic electron withdrawing groups G1 to G6,
wherein represents the connection location to the parent nucleus.
According to a preferred embodiment of the invention, R 5 Is one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R is 5 The adjacent aromatic rings or the adjacent heteroaromatic rings may each be independently linked to each other by a chemical bond to form a ring. Here, R is 5 Preferably hydrogen.
In the present invention, preferably, the R 5 The "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, C3-C60 heteroarylamino
According to the invention, k is preferably an integer from 0 to the maximum allowed.
In a preferred embodiment of the present invention, the structure represented by formula (2) is one of the following formulas (3), (4), (5) and (6),
in the formulae (3) to (8), the Z 1 、Z 2 、Z 3 And Z 4 Are independently selected from CR 4 ，R 4 The meaning of the expression is as in claim 3, R 3 One selected from hydrogen, halogen, carboxyl, nitro, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 thioalkoxy, amino, alkyl substituted amino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl; r is R 3 Preferably a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C3-C60 heteroaryl group, more preferably a substituted or unsubstituted phenyl group; r is R 3 The ring D and the ring E can be connected with each other through chemical bonds to form a ring,
the "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, and C3-C60 heteroarylamino.
As a preferred embodiment of the present invention, X 3 、X 4 Each independently selected from one of cyano, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, X 3 、X 4 Further preferred are a substituted or unsubstituted C1-C6 chain alkyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl dibenzofuranyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiophenyl group.
As a preferred embodiment of the present invention, X is preferably 3 、X 4 The atom attached to the parent nucleus is not O, S, since the inventors found that when X 3 、X 4 When the atom connected to the parent nucleus is O, S, the effect of the device is not ideal.
As a preferred embodiment of the present invention, X in formula (2) 1 、X 2 Are all NR 3 And G is a group selected from F, cyano and trifluoromethyl, the boron-containing organic compound has a non-axisymmetric structure with a B-G line as an axis.
The term "asymmetric" as used herein means that the structure on the left and right sides is not axisymmetric, taking the compound of formula (1) as an example, and taking the B-G line as an axis. It may be that ring D and ring E are not identical, and here include the difference in substituents thereof; may also be X 1 And X 2 R not identical, or attached thereto 1 、R 2 、R 3 Different from each other on the left side and the right side; x may also be 3 、X 4 Different; combinations of the above are also possible.
The inventors found that when X 1 、X 2 Are all NR 3 And when G is a group selected from F, cyano and trifluoromethyl, the life property of the device is not ideal, probably because the steric effect of the group selected from F, cyano and trifluoromethyl as the group is too small, the sublimation difficulty of the material is improved, and the film forming performance is poor. This case is X 1 、X 2 And O and S are not obvious. However, the inventors have found that when the whole molecule is of a non-axisymmetric structure having a B-G line as an axis, the lifetime characteristics of the device can be greatly improved. The specific reasons are not clear, and the possible reasons are presumed to be: the material has asymmetric characteristics, is beneficial to adjusting the light color of the material and the sublimation temperature of the material, and is beneficial to film formation, thereby realizing better service life characteristics. At the same time, when X 1 、X 2 In the case of O and S, the compounds themselves are less difficult to sublimate and the number of groups attached is less than X 1 、X 2 In the case of N, the influence of the symmetrical structure of the molecule on the film formation becomes small.
Further, the organic compound of the present invention may preferably be a compound having a specific structure shown below, which is merely representative and does not limit the scope of the present invention.
Meanwhile, the fluorescent quantum efficiency is high, and the fluorescent quantum efficiency is used as an OLED luminescent layer material, so that the balance of carrier transmission of the luminescent layer is facilitated, the luminescent efficiency of the device is improved, and the service life of the device is prolonged.
When the compound provided by the invention is used as a luminescent material, especially as a red light material, the compound has good luminescent performance, and the compound is used as an OLED luminescent layer material, so that the luminescent efficiency of a device is improved. The compounds of the invention can be used as luminescent dyes, in particular red luminescent dyes.
The specific reason why the above-described compound of the present invention is excellent in performance as a light-emitting layer in an organic electroluminescent device is not clear, and it is presumed that the following reasons are possible:
1. in the invention, the para position of the coordination of the molecular center aromatic ring and the B atom is connected with the electron withdrawing group, and on the premise of keeping multiple resonances, the effective red shift is generated through the energy level splitting of the front line orbit, so that the target molecule has high luminous efficiency and high color purity. The series of materials can obtain red light to near infrared emission.
2. In the invention, the aromatic substituent groups connected on the aromatic ring in the molecular center are not identical, and the material has asymmetric characteristics. The light color of the material and the sublimation temperature of the material are adjusted, and the material can be taken out to have a certain positive effect, so that the luminous efficiency of the material can be improved.
3. Besides the electron withdrawing group on the aromatic ring in the molecular center, a substituted steric hindrance group which is not H is arranged, so that the thermal activation delay property of the B-containing resonance type material is improved, and the efficiency of the device is improved.
The compound of the invention is suitable for being used as a functional material of an organic light-emitting device. However, the application of the compound of the invention is not an organic light-emitting device. Such organic electronic devices include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, information labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.
The invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one or more luminescent functional layers inserted between the first electrode and the second electrode, wherein the luminescent functional layers contain at least one compound shown in the general formula (1).
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturing enterprises on high-performance materials.
The compound disclosed by the invention can be used as a TADF material, a light-emitting layer guest material or a doping agent, is suitable for a TADF OLED or a TASF OLED device, and can effectively improve the performance of the device. The OLED device has good carrier transmission performance and high luminous efficiency, and has potential application in solving the problem of efficiency roll-off of the OLED device under high current density and prolonging the service life of the device.
Detailed Description
The technical scheme of the invention is further more specifically described below. It should be apparent to those skilled in the art that the detailed description, as well as the examples, are merely intended to facilitate an understanding of the invention and are not intended to limit the invention to the particular forms disclosed.
The compounds of the invention are obtained wherein M is halogen, typically F, cl, br, I:
general synthetic route:
the compounds of formula (I) according to the invention can be obtained by known methods, for example by synthesis by known organic synthesis methods. Exemplary synthetic routes are given below, but may be obtained by other methods known to those skilled in the art. The representative synthetic route for the compounds of the general formula of the present invention is as follows:
device implementation method
The device structure of the Organic Light Emitting Device (OLED) of the present invention is the same as the prior art. In general, an OLED includes a first electrode and a second electrode, 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 particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. 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 the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations 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 hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below 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 of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds of HT-1 through HT-51 may also be used to dope one or more of HI-1-HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise 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 various colors may be arranged in a planar manner in accordance with the pixel pattern, or may be stacked together to form a color light-emitting layer. When 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 simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the present invention, the host material of the light emitting layer is preferably selected from one or more of PH-1 to PH-85, but is not limited to these materials.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described above; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, but are not limited thereto.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following:
LiQ、LiF、NaCl、CsF、Li 2 O、Cs 2 CO 3 、BaO、Na、Li、Ca、Mg、Yb。
examples
The organic compound of the invention is representatively synthesized, and is applied to an organic electroluminescent device together with a corresponding comparative compound to test the device performance under the same conditions.
Synthetic examples
Specific methods for preparing the above novel compounds of the present invention will be described below by way of example with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples. It should be noted that, the method for obtaining the compound is not limited to the synthetic method and raw materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the compound proposed in the present invention. All compounds of the synthesis process not mentioned in the present invention are commercially available starting products or are prepared by such starting products according to known methods. The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, t-butylbenzene, boron tribromide, carbazole, diphenylamine, etc., may be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai pichia pharmaceutical company, carboline reagent company, etc. Analytical detection of intermediates and compounds in the present invention uses an absiex mass spectrometer (4000 QTRAP).
Synthesis example 1
Synthesis of compound M4:
synthesis of intermediate M4-1:
adding A (40 g,130 mmol), B (76.24 g,272.8 mmol), potassium carbonate (53.8 g,389.8 mmol) and N, N-dimethylformamide (300 ml) into a 1L three-port bottle, replacing 3 times with nitrogen, heating to 70 ℃ for 4 hours, performing TLC analysis, dropping water (2L) into the reaction solution, suction filtering, collecting, refluxing and pulping with ethanol (1L) for 1 hour, cooling to room temperature, filtering, collecting filter cake, recrystallizing with toluene/ethanol, and drying with air at 50 ℃ to obtain white solid 58g
Synthesis of intermediate M4-2:
m4-1 (20 g,24.19 mmol), C (23.18 g,72.58 mmol), cesium carbonate (31.53 g,96.77 mmol), N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, nitrogen was purged 3 times, and the temperature was raised to 110℃for reaction for 12 hours. The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate M4-2 30g.
Synthesis of compound M4:
intermediate M1-3 (24.66 g,18 mmol) was added to a 500ml three-necked flask, tert-butylbenzene (170 ml) was added, and after stirring for 20 minutes, the reaction system was cooled to 0℃and then n-butyllithium (12 mL,30 mmol) was added, and stirring was continued for 30 minutes while maintaining a low temperature. Then gradually heating to 60 ℃ and continuously heating for 2h. The reaction system temperature was again lowered to 0℃and boron tribromide (2.9 ml,30 mmol) was added under nitrogen protection, followed by stirring for 10 minutes and then heating to 60℃for 30 minutes. The temperature of the system was again lowered to 0deg.C and diisopropylethylamine (6 mL,34.4 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gives 10.2g crude product, toluene/ethanol recrystallization gives 5.2g red solid with 99.32% purity. Mass spectrometry determines molecular ion mass: 1299.67 (theory: 1299.63).
Synthesis example 2
Synthesis of compound M7:
synthesis of intermediate M7-1:
synthesis of M4-1 gave 68g of a white solid after recrystallization.
Synthesis of intermediate M7-2:
m7-1 (20 g,24.19 mmol), C (12.4 g,72.58 mmol), cesium carbonate (31.53 g,96.77 mmol), N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, nitrogen was purged 3 times, and the temperature was raised to 110℃for reaction for 12 hours. The temperature of the system was lowered to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate M7-2.19 g.
Synthesis of compound M7:
the synthesis scheme is the same as that of M4, 11.2g of crude product is obtained by chromatography, 5.1g of red solid is obtained by toluene/ethanol recrystallization, and the purity is 99.12%. Mass spectrometry determines molecular ion mass: 1001.78 (theory: 1001.50).
Synthesis example 3
Synthesis of Compound M50:
synthesis of intermediate M50-1:
a (37.1 g,90 mmol), B (27.23 g,97.44 mmol), potassium carbonate (16.16 g,116.93 mmol) and N, N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, the mixture was purged with nitrogen 3 times, and the temperature was raised to 40℃for 5 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate M50-1.9 g.
Synthesis of intermediate M50-2:
synthesis of M4-2 gave 55.8g of a white solid after recrystallization.
Synthesis of Compound M50:
the synthesis scheme is the same as that of M4, and the chromatography is performed to obtain 10.2g of crude product, and toluene/ethanol is recrystallized to obtain 6.3g of solid with the purity of 99.14%. Mass spectrometry determines molecular ion mass: 748.65 (theory: 748.32).
Synthesis example 4
Synthesis of compound M91:
synthesis of intermediate M91-1:
a (48.8 g,90 mmol), B (27.23 g,97.44 mmol), potassium carbonate (16.16 g,116.93 mmol) and N, N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, the mixture was purged with nitrogen 3 times, and the temperature was raised to 40℃for 5 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate M50-1.2 g.
Synthesis of intermediate M91-2:
synthesis of M4-2 gave 64.6g of a white solid after recrystallization.
Synthesis of compound M91:
the synthesis scheme is the same as that of M4, and the chromatography is carried out to obtain 8.5g of crude product, and toluene/ethanol recrystallization is carried out to obtain 4.2g of red solid with the purity of 99.03 percent. Mass spectrometry determines molecular ion mass: 1030.56 (theory: 1030.41).
Device embodiment
Example 1
The above examples and comparative examples respectively provide an organic electroluminescent device, which is prepared as follows:
(1) The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed 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 cation beam;
(2) Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, vacuum evaporating HI-3 as a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 2nm;
(3) Vacuum evaporating a hole transport layer HT-28 on the hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30nm;
(4) Vacuum evaporating an electron blocking layer HT-32 on the hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 10nm;
(5) The luminescent layer is formed by vacuum evaporation on the electron blocking layer, the luminescent layer comprises a main body material PH-14 and a boron-containing organic material in the patent, the mass doping concentration of the boron-containing organic material is 10wt%, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm by utilizing a multi-source co-evaporation method.
(6) Vacuum evaporating ET-17 on the luminous layer as a hole blocking layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 5nm;
(7) Vacuum evaporating ET-60 and ET-57 on the hole blocking layer as electron transport layers, wherein the ratio is 1:1, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 25nm;
(8) Liq with the thickness of 1nm is vacuum evaporated on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
The structures of the organic electroluminescent devices provided in the above examples and comparative examples include an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an emission layer (EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode in this order from bottom to top.
Examples 2 to 17, comparative examples 1 to 3
Examples 2 to 17 and comparative examples 1 to 3 were prepared in the same manner as in example 1, except that the dyes in the light-emitting layer were replaced with other materials, including Ref-1, ref-2 and Ref-3, respectively. The examples and comparative examples described above differ from each other only in the specific choice of boron-containing organic material, see in particular table 1.
Wherein Ref-1 is obtained according to the synthesis method of the invention, replacing an intermediate. The method for obtaining Ref-2 is described in https:// doi.org/10.26434/chemrxiv.1405502.v1, which is not described in detail herein. Ref-3 refers to the method described in CN 110407859A and is not described in detail herein.
The testing method of the device comprises the following steps:
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices manufactured in examples 1 to 17 and comparative examples 1 to 3 were measured using a digital source table and PR650 at the same brightness. Specifically, the voltage was increased at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 10mA/cm 2 The voltage at the time is the corresponding driving voltage, and meanwhile, the external quantum efficiency (EQE%) of the device can be obtained through direct test on PR 650;
the lifetime test of LT95 is as follows: maintaining the device at 50mA/cm 2 The time for which the luminance of the organic electroluminescent device was reduced to 95% of the original luminance was measured at a constant current density in hours using a luminance meter, with the life of Ref-1 as 100%, and the rest was compared with the percentage.
Table 1 organic electroluminescent device Performance of examples
The results show that the novel organic material is used for the organic electroluminescent device, compared with the comparative example devices 1-3, the example devices 1-17 can effectively reduce the landing voltage, improve the current efficiency, prolong the service life of the device, and are luminescent materials with good performance.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. While the invention has been described in connection with the embodiments, it is to be understood that the invention is not limited to the above embodiments, but is capable of numerous modifications and improvements within the spirit of the invention, as will be apparent to those skilled in the art, and it is intended to cover in the appended claims all such modifications and improvements as fall within the true scope and spirit of the invention.
Claims (11)
1. A boron-containing organic compound characterized by having a structure represented by formula (1):
in the formula (1), the ring A, the ring D and the ring E are respectively one of C6-C60 aromatic rings and C3-C60 heteroaromatic rings independently;
R a 、R b each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said R a 、R b Adjacent toThe aromatic rings or with adjacent heteroaromatic rings may each independently be linked to each other by a chemical bond to form a ring; m and n are integers from 0 to the maximum allowable;
X 1 、X 2 each independently selected from O, S, CR 1 R 2 、NR 3 ；
X 3 、X 4 Each independently selected from one of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
R 1 、R 2 、R 3 each independently selected from one of hydrogen, halogen, carboxyl, nitro, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 thioalkoxy, amino, alkyl substituted amino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl; the R is 1 、R 2 、R 3 The ring D and the ring E can be connected with each other through chemical bonds to form a ring;
G is an electron withdrawing group;
the "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, and C3-C60 heteroarylamino.
2. The boron-containing organic compound according to claim 1, wherein,
at least one of the ring D and the ring E is a benzene ring or a six-membered heteroaromatic ring, and the ring A is a benzene ring or a six-membered heteroaromatic ring.
3. The boron-containing organic compound according to claim 2, wherein the structure thereof is represented by formula (2):
in the formula (2), the Z 1 、Z 2 、Z 3 And Z 4 Are independently selected from CR 4 Or N, the R 4 Is one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R is 4 Each of which may be independently linked to each other by a chemical bond to form a ring;
R 4 The "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, and C3-C60 heteroarylamino;
X 1 、X 2 、X 3 、X 4 the meaning of G is the same as in claim 1.
4. A boron-containing organic compound according to any one of claims 1 to 3, wherein G is at least one aromatic electron withdrawing group selected from the group consisting of F, cyano, trifluoromethyl and G1 to G6,
wherein represents the connection position to the parent nucleus;
R 5 is one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R is 5 Each of which may be independently linked to each other by a chemical bond to form a ring; preferably R 5 Is hydrogen;
k is an integer from 0 to the maximum allowable.
5. The boron-containing organic compound according to claim 4, wherein the structure represented by the formula (2) is at least one of the following formulas (3), (4), (5) and (6),
in the formulae (3) to (8), the Z 1 、Z 2 、Z 3 And Z 4 Are independently selected from CR 4 ，R 4 The meaning of the expression is as in claim 3, R 3 Selected from the group consisting of hydrogen, halogen, carboxyl, nitro, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 thioalkoxy, amino, alkyl substituted amino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstitutedOne of an aryloxy group of C6-C60, a substituted or unsubstituted heteroaryl group of C3-C60; r is R 3 Preferably a substituted or unsubstituted C6-C60 aryl group, or one of a substituted or unsubstituted C3-C60 heteroaryl group, more preferably a substituted or unsubstituted phenyl group; r is R 3 The ring D and the ring E can be connected with each other through chemical bonds to form a ring,
the "substituted or unsubstituted" means substituted with one or a combination of at least two selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylamino, and C3-C60 heteroarylamino.
6. A boron-containing organic compound according to any one of claim 1 to 3,
X 3 、X 4 each independently selected from one of cyano, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, X 3 、X 4 Further preferred are a substituted or unsubstituted C1 to C6 chain alkyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl dibenzofuranyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group.
7. The boron-containing organic compound according to claim 4, wherein X in the formula (2) 1 、X 2 Are all NR 3 And G is a group selected from F, cyano and trifluoromethyl, the boron-containing organic compound has a non-axisymmetric structure with a B-G line as an axis.
8. The boron-containing organic compound according to claim 1, wherein the structure represented by formula (1) is a compound structure represented by:
9. an organic electroluminescent material which is the compound according to any one of claims 1 to 8;
Preferably, the luminescent material is a red luminescent material;
preferably, the luminescent material is applied in a fluorescent organic light emitting device; further preferably, the organic light emitting device is a thermally activated delayed fluorescence light emitting device.
10. Use of a compound according to any one of claims 1 to 8 as a functional material in an organic electronic device comprising: organic electroluminescent devices, optical sensors, solar cells, lighting elements, information labels, electronic artificial skin sheets, sheet scanners, or electronic papers.
11. 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 compound according to any one of claims 1 to 8.
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