CN117143121A - Compounds and uses thereof - Google Patents
Compounds and uses thereof Download PDFInfo
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- CN117143121A CN117143121A CN202210539150.4A CN202210539150A CN117143121A CN 117143121 A CN117143121 A CN 117143121A CN 202210539150 A CN202210539150 A CN 202210539150A CN 117143121 A CN117143121 A CN 117143121A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 162
- 125000003118 aryl group Chemical group 0.000 claims abstract description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 31
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 26
- 229910052722 tritium Inorganic materials 0.000 claims abstract description 26
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 25
- 150000001975 deuterium Chemical group 0.000 claims abstract description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 116
- -1 nitro, carboxyl Chemical group 0.000 claims description 115
- 239000000463 material Substances 0.000 claims description 82
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 39
- 125000004104 aryloxy group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
- 235000010290 biphenyl Nutrition 0.000 claims description 31
- 239000004305 biphenyl Substances 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 21
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 239000002346 layers by function Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001624 naphthyl group Chemical class 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 13
- 229910052796 boron Inorganic materials 0.000 claims description 13
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 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 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 11
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 11
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000005264 aryl amine group Chemical group 0.000 claims description 9
- 229910000085 borane Inorganic materials 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 7
- 230000005669 field effect Effects 0.000 claims description 7
- 238000013086 organic photovoltaic Methods 0.000 claims description 7
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000000956 methoxy group Chemical class [H]C([H])([H])O* 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical class 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical class 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical class 0.000 claims description 4
- 125000001725 pyrenyl group Chemical class 0.000 claims description 4
- 125000004076 pyridyl group Chemical class 0.000 claims description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 238000012984 biological imaging Methods 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical class C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000006748 (C2-C10) heterocycloalkenyl group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical class O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001300 boranyl group Chemical class [H]B([H])[*] 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 125000002178 anthracenyl group Chemical class C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 26
- 229920000642 polymer Polymers 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 44
- 238000003756 stirring Methods 0.000 description 43
- 239000012295 chemical reaction liquid Substances 0.000 description 32
- 239000002994 raw material Substances 0.000 description 31
- 238000004440 column chromatography Methods 0.000 description 28
- 238000010438 heat treatment Methods 0.000 description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 22
- 238000006467 substitution reaction Methods 0.000 description 22
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 20
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 16
- 238000001035 drying Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 7
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000011669 selenium Substances 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 5
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 4
- 230000003190 augmentative effect Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 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 3
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
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- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 2
- AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical group CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
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- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-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
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
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- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical group [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group 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-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
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- 239000010931 gold Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
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- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229960002429 proline Drugs 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 239000004984 smart glass Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical group CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical class C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 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
- 238000003618 dip coating Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000007641 inkjet printing Methods 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
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- XJWOWXZSFTXJEX-UHFFFAOYSA-N phenylsilicon Chemical group [Si]C1=CC=CC=C1 XJWOWXZSFTXJEX-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The embodiment of the application provides a compound which is a polymer with a structure shown in a formula (I):wherein M is 2 、M 3 A substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring, respectively; z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence of which is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, and the like, adjacent R' s 1 Can be connected into a ring. The compound has good luminescence property, and can be used for improving the property of a luminescent device in the luminescent device.
Description
Technical Field
The application relates to the technical field of organic luminescent materials, in particular to a compound and application thereof.
Background
The organic luminescent material has good luminescence property and good adjustability, the molecular design is relatively flexible, and the organic luminescent material can be coated on various base materials to form a film, so the organic luminescent material is widely applied to various fields such as organic electroluminescent devices (Organic Light Emission Diodes, OLEDs), organic luminescent field effect transistors, organic photovoltaic devices, luminescent electrochemical cells, photoelectric converters, light-emitting devices, image sensors, lasers, photosensitive devices, biological imaging devices, paints, organic laser devices and the like. The organic electroluminescent device is an energy conversion device which uses an organic luminescent material as a luminescent material and can convert applied electric energy into light energy. The display device has the characteristics of high brightness, quick response, wide viewing angle, flexibility and the like, and is widely applied to the fields of display, illumination and the like. However, along with the improvement of the display effect of the display device, higher requirements such as high efficiency, stability, high luminous color purity and the like are also put forward for the OLEDs luminescent materials. Therefore, there is a need to develop new organic light emitting materials to meet the growing demands of OLEDs.
Disclosure of Invention
In view of the above, embodiments of the present application provide a compound having good light emitting properties, which can improve the performance of a light emitting device.
Specifically, in a first aspect, an embodiment of the present application provides a compound that is a polymer having a structure represented by formula (one):
wherein M is 2 、M 3 A substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring, respectively; z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted ringAlkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted borane, substituted or unsubstituted silyl, substituted or unsubstituted aromatic silicon group, or C containing at least one heteroatom other than O, N, S, B, P, F 1 -C 18 Electron withdrawing groups of (C), adjacent R 1 Can be connected into a ring.
The compound provided by the embodiment of the application is a polymer with a structure shown in the formula (I), so that the molecular structure of the compound contains two or more structures shown in the formula (I), and the compound has good luminescence property and is easy to synthesize. Specifically, the compound takes a condensed ring structure formed by boron atoms, Y groups, naphthalene rings and the like as a skeleton center, the skeleton center of the condensed ring structure can generate good resonance effect, the resonance area is large, the resonance effect is strong, and the condensed ring structure has high electrical stability; meanwhile, the framework center of the condensed ring structure is a rigid framework structure, so that the relaxation degree of the excited state structure can be effectively reduced, and the compound can obtain higher fluorescence quantum yield, narrower full width at half maximum (FWHM, full Width at Half Maxima), and proper energy levels of HOMO (Highest Occupied Molecular Orbital ) and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital). The compound disclosed by the embodiment of the application has the advantages of high structural stability, high electrical stability, high fluorescence quantum yield and narrow half-peak width, and can be used as a luminescent material to be applied to a luminescent device, so that the device efficiency, the luminescent color purity and the device stability can be improved. In the embodiment of the application, various substituents are introduced into the framework center of the condensed ring structure, so that the adjustment of the luminescence peak position and the like of the compound can be further realized, more compounds with different luminescence colors (such as red light, green light and blue light) and different luminescence behaviors (narrow spectrum, smaller Stokes shift and high color purity) can be obtained, and the application range is enlarged.
In an embodiment of the present application, the compound is a polymer having 2 to 6 structures represented by the formula (one). Different amounts of the structure of formula (one) may result in a greater variety of different compounds.
In an embodiment of the present application, the compound has any one of the structural general formulas shown in the formulas (I) to (X):
in the formulae (I) to (X), Z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or unsubstituted heterocycloalkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted borane group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic silyl group, or a C containing at least one heteroatom other than O, N, S, B, P, F 1 -C 18 Electron withdrawing groups of (C), adjacent R 1 Can be connected into a ring, R 2 Can be adjacent to R 1 Connected into a ring. The compounds of the formulas (I) to (X) have good luminescence property, are easy to prepare, and are beneficial to realizing mass production.
In an embodiment of the present application, the substituents in the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted heterocycloalkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted alkoxy, substituted aryloxy, substituted aryl, substituted heteroaryl, substituted heteroaryloxy, substituted alkylamino, substituted arylamino, substituted heteroarylamino, substituted borane, substituted silyl, substituted aryl comprise one or more of deuterium atom, tritium atom, halogen atom, cyano, nitro, carboxyl, sulfonic, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl. The selection of different substituents can lead the variety of the compounds to be richer, and certain compound products with slightly different properties can be obtained, thereby better realizing the application.
In an embodiment of the present application, the substituted or unsubstituted alkyl group is a substituted or unsubstituted C 1 -C 30 An alkyl group; the substituted or unsubstituted cycloalkyl is substituted or unsubstituted C 3 -C 30 Cycloalkyl; the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C 2 -C 30 A heterocycloalkyl group; the substituted or unsubstituted alkenyl group is a substituted or unsubstituted C 2 -C 30 Alkenyl groups; the substituted or unsubstituted cycloalkenyl is substituted or unsubstituted C 3 -C 10 A cycloalkenyl group; the substituted or unsubstituted heterocycloalkenyl is substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl; the substituted or unsubstituted alkynyl is substituted or unsubstituted C 2 -C 30 Alkynyl; the substituted or unsubstituted cycloalkynyl group is a substituted or unsubstituted C 6 -C 10 A cycloalkynyl group; the substituted or unsubstituted heterocyclylalkynyl is a substituted or unsubstituted C 5 -C 10 Heterocyclic alkynyl; the substituted or unsubstituted alkoxy is substituted or unsubstituted C 1 -C 30 An alkoxy group; the substituted or unsubstituted aryloxy group is a substituted or unsubstituted C 6 -C 30 An aryloxy group; the substituted or unsubstituted aryl is substituted or unsubstituted C 6 -C 30 An aryl group; the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C 3 -C 30 Heteroaryl; the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C 3 -C 30 A heteroaryloxy group; the substituted or unsubstituted alkylamino is substituted or unsubstituted C 1 -C 30 An alkylamino group; the substituted or unsubstituted arylamine group is a substituted or unsubstituted C 6 -C 30 An arylamine group; the substituted or unsubstituted heteroaromatic amine group is a substituted or unsubstituted C 3 -C 30 Heteroaromatic amine groups. The number of carbon atoms of each group is controlled to be a certain number, so that raw materials are easier to obtain, and the preparation process is more controllable.
In an embodiment of the present application, the group other than the above contains C which is at least one hetero atom of O, N, S, B, P, F 1 -C 18 Comprises a substituted or unsubstituted imide group, a substituted or unsubstituted amide group, a cyano group, a nitro group or a hydroxyl group.
In an embodiment of the present application, the R 1 、R 2 Each occurrence is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuteromethyl group, a tritiated methyl group, a fluoro-propyl group, a trifluoromethyl group, an ethyl group, a deuteroethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a phenyl-substituted tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a tert-butyl-substituted dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a tert-butyl-substituted N-substituted carbazolyl group, a 9-dicarbazolyl group, a Methyl fluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, t-butyl substituted phenyl, biphenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, t-butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated t-butyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated ethyl substituted biphenyl, deuterated isopropyl substituted biphenyl, deuterated t-butyl substituted biphenyl, phenyl substituted amino, t-butylbenzene substituted amino, t-butyl substituted dibenzofuranyl, phenyl substituted t-butyl, xanthonyl, triazinyl, phenyl substituted triazinyl, borane, phenyl substituted borane, methoxy or t-butoxy. The above groups are advantageous for obtaining a compound having good light-emitting properties, and enable easy preparation of the compound.
In an embodiment of the present application, adjacent R's are 1 When connected in a ring, the ring structure formed includes any one of the formulae (a) to (i):
In the formulae (a) to (i), the positions of the marks are connection positions, and the structures of the formulae (a) to (i) are connected in a parallel ring manner through the positions of the marks. Adjacent R 1 The compound is connected into the ring structure, so that the compound is richer in variety, better in application, good in luminescence performance and easy to prepare.
In an embodiment of the present application, the R 2 Adjacent to said R 1 When connected in a ring, the ring structure formed includes structures represented by formulas (a) to (D):
r in formula (A) 5 Is a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, n is an integer of 0 to 4; in the formulae (a) to (D), the positions of the marks are connection positions, and the structures of the formulae (a) to (D) are connected in parallel by the positions of the marks. R is R 2 Adjacent to said R 1 The compound is connected into the ring structure, so that the compound is richer in variety, better in application, good in luminescence performance and easy to prepare.
In an embodiment of the present application, the compound includes any one of compounds represented by structural formulas (1) to (268):
a second aspect of embodiments of the present application provides the use of a compound according to the first aspect and salts thereof in electroluminescent devices, organic light emitting field effect transistors, organic photovoltaic devices, light emitting electrochemical cells, photoelectric converters, light opening devices, image sensors, lasers, light sensing devices, biological imaging devices, paints, organic laser devices. The compound provided by the embodiment of the application has good luminescence property, and can improve the property of a luminescent device.
A third aspect of an embodiment of the present application provides a light-emitting layer comprising the compound of the first aspect. The compound provided by the embodiment of the application has good luminescence property, and can improve the property of a luminescent device.
In an embodiment of the present application, the light emitting layer includes a host material and a doping material, and the doping material includes the compound. The compound provided by the embodiment of the application has smaller Stokes displacement, and can be used as a doping material to sensitize a main material emitting visible light better.
According to a fourth aspect of embodiments of the present application there is provided an electronic device comprising a compound according to the first aspect; or comprises a light emitting layer according to the third aspect. The compound provided by the embodiment of the application has good luminescence property, and can improve the property of a luminescent device.
In an embodiment of the application, the electronic device comprises a cathode and an anode, and a functional layer between the cathode and the anode, the functional layer comprising the compound.
In an embodiment of the application, the electronic device comprises an electroluminescent device, an organic light emitting field effect transistor, an organic photovoltaic device or a light emitting electrochemical cell.
A fifth aspect of an embodiment of the present application provides a display device, including the electronic device of the fourth aspect; or comprises a light emitting layer according to the third aspect. The compound provided by the embodiment of the application has good luminescence property, and is beneficial to improving the display effect of a display device.
The embodiment of the application also provides electronic equipment, which is characterized by comprising the display device of the fifth aspect; or comprises the electronic device of the fourth aspect. The compound provided by the embodiment of the application has good luminescence property, is beneficial to improving the display effect of electronic equipment and improves the market competitiveness of the electronic equipment.
The embodiment of the application also provides a lighting device, which is characterized in that the lighting device comprises the electronic device of the fourth aspect; or comprises a light emitting layer according to the third aspect. The compound provided by the embodiment of the application has good luminescence property, is beneficial to improving the luminescence effect of the lighting device and improves the market competitiveness of the lighting device.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device 100 according to an embodiment of the present application;
fig. 2 is a schematic structural diagram of a display device 200 according to an embodiment of the application;
Fig. 3 is a schematic structural diagram of an electronic device 300 according to an embodiment of the present application;
FIG. 4 is a high resolution mass spectrum of compound 4 prepared in example 1 of the present application;
FIGS. 5 and 6 are respectively a hydrogen nuclear magnetic resonance spectrum and a carbon nuclear magnetic resonance spectrum of the compound 4 prepared in example 1 of the present application;
FIG. 7 is an ultraviolet absorption spectrum and a fluorescence spectrum of the compound 4 in example 1 of the present application;
FIG. 8 is a nuclear magnetic resonance hydrogen spectrum of the compound 32 prepared in example 2 of the present application;
FIG. 9 is a fluorescence spectrum of Compound 32 in example 2 of the present application;
FIG. 10 is a nuclear magnetic resonance hydrogen spectrum of compound 139 prepared in example 3 of the present application;
FIG. 11 is an ultraviolet absorption spectrum and a fluorescence spectrum of a compound 139 in example 3 of the present application;
fig. 12 is a schematic structural view of an organic electroluminescent device 100 of device embodiment 1;
FIG. 13 is a graph showing luminescence spectra of the devices of device example 1 and device example 2 of the present application;
FIG. 14 is a plot of current density versus voltage versus luminance for devices of device example 1 and device example 2 of the present application;
fig. 15 is a luminance-external quantum efficiency plot for the devices of device example 1 and device example 2 of the present application.
Detailed Description
Embodiments of the present application will be described below with reference to the accompanying drawings.
Referring to fig. 1, fig. 1 is a schematic structural diagram of an organic electroluminescent device (OLEDs) 100 according to an embodiment of the present application. The organic electroluminescent device 100 shown in fig. 1 includes an anode 10, a cathode 20, and a functional layer 30 between the anode 10 and the cathode 20, the functional layer 30 including a light emitting layer 301. After a certain voltage is applied between the anode 10 and the cathode 20 of the organic electroluminescent device 100, the light-emitting material in the light-emitting layer 301 is excited to emit light by recombination of holes and electrons in the light-emitting layer 301, thereby imparting a light-emitting function to the organic electroluminescent device 100. With the advent of the 5G era, a new generation of display standard has put higher demands on display technologies, for example, the light-emitting material in the light-emitting layer 301 needs to have high light-emitting efficiency, stable properties, high light-emitting color purity, and other performances, so as to meet the display standard with higher demands. For this reason, the embodiment of the present application provides a compound that can be used for the above-described light-emitting layer 301, so that the organic electroluminescent device obtains good light-emitting performance, and the compound is easy to realize preparation.
The following will specifically describe the above compound, which is a boron-containing organic compound, which is a polymer of the structure represented by the formula (one):
Wherein M is 2 、M 3 A substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring, respectively; z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or unsubstituted heterocycloalkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl groupA group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted borane group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic silicon group, or a C containing at least one heteroatom of O, N, S, B, P, F other than the above groups 1 -C 18 Electron withdrawing groups of (C), adjacent R 1 Can be connected into a ring.
The compound provided by the embodiment of the application is a polymer with a structure shown in a formula (I), thus the molecular structure of the compound comprises two or more structures shown in the formula (I), and because the structure shown in the formula (I) is provided with a No. 1 ring comprising B atoms and Y atoms (or groups), the No. 1 ring is a boron heterocycle, and a naphthalene ring is introduced on the No. 2 ring in a parallel ring mode, and meanwhile, M is a compound with a structure shown in the formula (I) 2 Ring, M 3 Under the combined action of the rings, the compound has good luminous performance and is easy to synthesize.
In an embodiment of the present application, in formula (one), M 2 、M 3 A substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring, respectively; in particular, the substituted or unsubstituted aromatic ring may be a substituted or unsubstituted C 6 -C 30 An aromatic ring such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted binaphthyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirofluorene ring, or the like; the substituted or unsubstituted heteroaryl ring may be substituted or unsubstituted C 3 -C 30 Heteroaryl rings such as a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted triazine ring, a substituted or unsubstituted xanthone ring, and the like; taking out The substituted or unsubstituted aliphatic ring may be substituted or unsubstituted C 2 -C 30 Aliphatic ring structures such as substituted or unsubstituted cyclopentane ring, substituted or unsubstituted cyclohexane ring, substituted or unsubstituted cyclopentene ring, substituted or unsubstituted cyclohexene ring, and the like.
In an embodiment of the application, M 2 、M 3 The substituents in the substituted aromatic ring, the substituted heteroaromatic ring and the substituted aliphatic ring comprise one or more of deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic acid group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryl group and substituted or unsubstituted amino group.
In some embodiments of the application, M 2 、M 3 Respectively a benzene ring, a deuterated benzene ring, a tritiated benzene ring, a methyl-substituted benzene ring, an ethyl-substituted benzene ring, an isopropyl-substituted benzene ring, a tert-butyl-substituted benzene ring, a deuterated methyl-substituted benzene ring, a deuterated ethyl-substituted benzene ring, a deuterated isopropyl-substituted benzene ring, a deuterated tert-butyl-substituted benzene ring, a cyano-substituted benzene ring, an adamantyl-substituted benzene ring, a pyridinyl-substituted benzene ring, a naphthalene ring, a deuterated naphthalene ring, a tritiated naphthalene ring, an alkyl-substituted naphthalene ring, a deuterated alkyl-substituted naphthalene ring, a tritiated alkyl-substituted naphthalene ring, an anthracene ring, a deuterated anthracene ring, a tritiated anthracene ring, an alkyl-substituted anthracene ring, a phenanthrene ring, a deuterated phenanthrene ring, an alkyl-substituted phenanthrene ring, a tritiated alkyl-substituted phenanthrene ring, a benzene ring, a deuterated biphenyl ring, a methyl-substituted naphthalene ring, a tritiated biphenyl ring, an ethyl-substituted naphthalene ring, an isopropyl-substituted naphthalene ring, a tert-butyl-substituted naphthalene ring, a deuterated alkyl-substituted naphthalene ring, a deuterated benzene ring, a methyl-substituted naphthalene ring, a tert-substituted benzene ring, a deuterated biphenyl ring, a tert-butyl-substituted benzene ring, a tert-substituted benzene ring, a tritiated benzene ring, a tert-substituted terpyridine-substituted benzene ring, a A substituted furan ring, thiophene ring, methyl-substituted thiophene ring, benzothiophene ring, benzofuran ring, methyl-substituted benzofuran ring, carbazole ring, carbazolyl benzene ring, alkyl-substituted carbazolyl benzene ring, phenylamino-substituted benzene ring, alkylphenylamino-substituted benzene ring, N-phenylcarbazole ring, benzofuran ring, dibenzofuran ring, tert-butyl-substituted dibenzofuran ring, dibenzothiophene ring, fluorene ring, alkyl-substituted fluorene ring, spirofluorene ring, triazine ring, phenyl-substituted triazine ring, xanthone ring, cyclopentane ring, deuterated cyclopentane ring, tritiated cyclopentane ring, methyl-substituted cyclopentane ring, cyclohexane ring, deuterated cyclohexane ring, tritiated cyclohexane ring, methyl-substituted cyclohexane ring, cyclopentene ring, deuterated cyclopentene ring, tritiated cyclopentene ring, methyl-substituted cyclopentene ring, cyclohexene ring, deuterated cyclohexene ring, tritiated cyclohexene ring, or methyl-substituted cyclohexene ring, etc.
In an embodiment of the present application, the compound is a polymer of 2 to 6 structures represented by formula (one), for example, the compound may be a polymer of 2, 3, 4, 5 or 6 structures represented by formula (one).
The compound provided by the embodiment of the application can have various structural forms, and the structures shown in the formula (I) in the compound can be connected in different modes, specifically can be connected through sharing certain ring structures, or through combining certain ring structures and ring connection, or through connecting groups and the like. For example, in some embodiments, the plurality of structures of formula (one) in the compound may be represented by a common naphthalene ring, a common M 2 Ring, common M 3 Rings, etc.; in some embodiments, the plurality of structures of formula (one) in the compound may be formed by a 1-ring union, M 2 The ring union ring, the ring union ring number 2 and the like are connected; in some embodiments, the plurality of structures of formula (one) in the compound may be linked by a single bond, phenylene, aromatic ring, aromatic heterocyclic ring, aliphatic ring, or alicyclic heterocyclic ring.
In some embodiments of the present application, the compound may have any one of the structural formulas shown in formulas (I) to (X):
in the formulae (I) to (X), Z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or unsubstituted heterocycloalkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted borane group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic silyl group, or a C containing at least one heteroatom other than O, N, S, B, P, F 1 -C 18 Electron withdrawing groups of (C), adjacent R 1 Can be connected into a ring, R 2 Can be adjacent to R 1 Connected into a ring.
The compound provided by the embodiment of the application takes a condensed ring structure formed by boron atoms, Y groups, naphthalene rings and the like as a skeleton center, the skeleton center of the condensed ring structure can generate good resonance effect, the resonance area is large, the resonance effect is strong, and the electric stability of the condensed ring structure is high; meanwhile, the framework center of the condensed ring structure is a rigid framework structure, so that the relaxation degree of an excited state structure of the compound can be effectively reduced, and the compound can obtain higher fluorescence quantum yield, narrower half width (FWHM, full Width at Half Maxima), and proper HOMO (Highest Occupied Molecular Orbital ) and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy levels; in addition, the compound disclosed by the embodiment of the application has small Stokes displacement and can play a good role in sensitizing materials emitting visible light. The "half-width" refers to the width of the peak at half the height of the luminescence peak in the electroluminescence spectrum of the luminescent material. The compound of the embodiment of the application can realize half-peak width smaller than 30 nm. The compound provided by the embodiment of the application has the advantages of high structural stability, high electrical stability, high fluorescence quantum yield and narrow half-peak width, and can be used as a luminescent material to be applied to a luminescent device, so that the device efficiency, the luminescent color purity and the device stability can be improved.
In the embodiment of the application, various substituents are introduced into the framework center of the condensed ring structure, so that the adjustment of the luminescence peak position and the like of the compound can be further realized, more compounds with different luminescence colors (such as red light, green light and blue light) and different luminescence behaviors (narrow spectrum, smaller Stokes shift and high color purity) can be obtained, and the application range is enlarged. The light-emitting position of the compound can be adjusted to a green light area, and in a full-color light-emitting device, green is taken as a main light-emitting color to provide brightness of about 60% of a full screen, so that the compound is more beneficial to being widely applied to the fields of full-color light-emitting devices of OLED-RGB three primary colors, OLED white light illumination and the like when the compound emits green light. The compound of the embodiment of the application can be obtained through a simpler synthesis path, can be synthesized without using dangerous chemicals such as butyl lithium and the like, is suitable for industrial production, and has good application effect and industrialization prospect in the field of OLED illumination or OLED display.
In an embodiment of the present application, in the formulae (I) to (X), Z represents C (R) 1 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 1 Each occurrence may be a group of the same structure or a group of a different structure. That is, Z at different positions may have the same structure or different structures, and specifically Z at all positions may be the same, or Z at all positions may be different, or Z at some positions may be the same. For example, in some embodiments, in formulas (I) through (X), all Z is C (H), or some Z is C (H), the remainder of Z are-C (CH) 3 )。
In embodiments of the application, in formulae (I) to (X), Y may be a group of the same structure or a group of a different structure at each occurrence, i.e. a plurality of Y may be groups of the same structure or groups of different structures. Wherein when a plurality of Y are groups of the same structure, they may be multipleEach Y is O, S, N (R) 2 ) Or Se; at this time, the boron-containing organic compound is easier to synthesize, the symmetry of the compound is higher, and the symmetrical rigid framework structure is more beneficial to reducing the relaxation degree of the excited state structure of the compound, so that the narrower half-peak width is obtained. When a plurality of Y are groups of different structures, they may be completely different types, for example, two Y are contained in the compound, for example, one Y is S or O or Se and the other Y is N (R 2 ) Or one Y is O and the other Y is S; it is also possible to have groups of the same type with different structures, for example two Y's are each N (R 2 ) But R is 2 Are not identical. Two Y in the formulas (I) to (X) contain hetero atoms, which is more beneficial to generating strong resonance effect with two boron atoms in the structural formulas.
In an embodiment of the present application, the substituents in the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted heterocycloalkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted alkoxy, substituted aryloxy, substituted aryl, substituted heteroaryl, substituted heteroaryloxy, substituted alkylamino, substituted arylamino, substituted heteroarylamino, substituted boranyl, substituted silyl, substituted aromatic silicon group include one or more of deuterium atom, tritium atom, halogen atom, cyano, nitro, carboxyl, sulfonic acid group, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl.
In an embodiment of the present application, the hetero atom in the heterocycloalkyl group, the heterocycloalkenyl group, the heterocycloalkynyl group, the heteroaryl group, the heteroaryloxy group and the heteroarylamine group may be one or more selected from an oxygen atom, a sulfur atom, a nitrogen atom and a selenium atom.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted alkyl group may be a linear alkyl group, a branched alkyl group, or a substituted or unsubstituted C 1 -C 30 Alkyl group. In some embodiments, the substituted or unsubstituted alkyl group may be a substituted or unsubstituted C 1 -C 10 Chain alkyl, substituted or unsubstituted C 1 -C 6 The chain alkyl group may be, for example, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted tert-butyl group, or the like. The substituents in the substituted alkyl group may be, but are not limited to, deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryl group. By way of example, the substituted alkyl group may be deuterated methyl, tritiated methyl, fluoroethyl, fluoropropyl, trifluoromethyl, deuterated ethyl, tritiated ethyl, deuterated isopropyl, tritiated isopropyl, deuterated t-butyl, tritiated t-butyl, phenyl-substituted t-butyl, and the like.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C 3 -C 30 Cycloalkyl groups. In some embodiments, the substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C 4 ～C 12 Cycloalkyl, substituted or unsubstituted C 5 ～C 6 Cycloalkyl groups may be specifically exemplified by substituted or unsubstituted cyclopentyl groups, substituted or unsubstituted cyclohexyl groups, substituted or unsubstituted adamantyl groups, and the like; the substituents in the substituted cycloalkyl groups may be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic groups, acyl groups, alkyl groups, alkoxy groups. Illustratively, the substituted cycloalkyl group may be a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, or the like.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted C 2 -C 30 A heterocycloalkyl group. In some embodiments, the substituted or unsubstituted heterocycloalkyl group can be a substituted or unsubstituted C 4 -C 12 Heterocycloalkyl, substituted or unsubstituted C 5 ～C 6 A heterocycloalkyl group. Illustratively, the substituted or unsubstituted heterocycloalkyl group can be a substituted or unsubstituted aziridine, a substituted or unsubstituted azetidine, a substituted or unsubstituted azacyclopentane.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted alkenyl group may be a substituted or unsubstituted C 2 -C 30 Alkenyl groups; the alkenyl group may be a straight chain alkenyl group or a branched chain alkenyl group. In some embodiments, the substituted or unsubstituted alkenyl group may be a substituted or unsubstituted C 2 -C 10 Alkenyl, substituted or unsubstituted C 2 -C 6 The alkenyl group may be, for example, a substituted or unsubstituted vinyl group, a substituted or unsubstituted propenyl group, or the like. The substituents in the substituted alkenyl group may be, but are not limited to, deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryl group. Illustratively, the substituted alkenyl groups may be deuterated vinyl, tritiated vinyl, fluorovinyl, fluoropropenyl, and the like.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted cycloalkenyl group may be a substituted or unsubstituted C 3 -C 10 A cycloalkenyl group. In some embodiments, the substituted or unsubstituted cycloalkenyl group may be a substituted or unsubstituted C 4 -C 7 Cycloalkenyl, substituted or unsubstituted C 5 -C 6 The cycloalkenyl group may be, for example, a substituted or unsubstituted cyclopentenyl group, a substituted or unsubstituted cyclohexenyl group, or the like. The substituents in the substituted cycloalkenyl group may be, but are not limited to, deuterium, tritium, halogen, cyano, nitro, carboxyl, sulfonic, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl. Illustratively, the substituted cycloalkenyl group may be a fluorocyclopentenyl, fluorocyclohexenyl, and the like.
The application is trueIn an embodiment, the above-mentioned substituted or unsubstituted heterocycloalkenyl group may be a substituted or unsubstituted C 2 -C 10 A cycloalkenyl group. In some embodiments, the substituted or unsubstituted heterocycloalkenyl may be substituted or unsubstituted C 3 -C 6 Heterocycloalkenyl, substituted or unsubstituted C 4 -C 5 The heterocycloalkenyl group may be, for example, a substituted or unsubstituted azacyclopentadiene, a substituted or unsubstituted cyclohexene oxide, or the like. The substituents in the substituted heterocycloalkenyl group may be, but are not limited to, deuterium, tritium, halogen, cyano, nitro, carboxyl, sulfonic, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl. By way of example, the substituted heterocycloalkenyl may be fluoroheterocyclopentadienyl, fluorooxahexenyl, and the like.
In embodiments of the application, the substituted or unsubstituted alkynyl group may be a substituted or unsubstituted C 2 -C 30 Alkynyl; the alkynyl group may be a straight chain alkynyl group or a branched chain alkynyl group. In some embodiments, the substituted or unsubstituted alkynyl group may be a substituted or unsubstituted C 2 -C 10 Alkynyl chain, substituted or unsubstituted C 2 -C 6 The alkynyl group may be, for example, a substituted or unsubstituted ethynyl group, a substituted or unsubstituted propynyl group, or the like. The substituents in the substituted alkynyl group may be, but are not limited to, deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryl group. Illustratively, the substituted alkynyl group may be a deuterated ethynyl group, a tritiated ethynyl group, a fluoroacetylenyl group, a fluoropropynyl group, or the like.
In embodiments of the application, the substituted or unsubstituted cycloalkynyl group may be a substituted or unsubstituted C 6 -C 10 Cycloalkynyl groups. The substituted or unsubstituted heterocycloalkynyl group may be substituted or unsubstituted C 5 -C 10 Heterocyclic alkynesA base.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted alkoxy group may be a substituted or unsubstituted C 1 -C 30 Alkoxy, which may be straight chain alkoxy or branched alkoxy; in some embodiments, the substituted or unsubstituted alkoxy group may be a substituted or unsubstituted C 1-20 Alkoxy, C 1 -C 10 Alkoxy, C 1 -C 6 An alkoxy group. As an example, the substituted or unsubstituted alkoxy group may be a substituted or unsubstituted methoxy group (-OCH) 3 ) Substituted or unsubstituted ethoxy (-OCH) 2 CH 3 ) Substituted or unsubstituted t-butoxy, and the like. The substituents in the substituted alkoxy groups may be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic groups, acyl groups, alkyl groups, alkoxy groups, cycloalkyl groups, and the like.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted aryl group may be a substituted or unsubstituted C 6 -C 30 An aryl group; the substituted or unsubstituted aryl group may be a substituted or unsubstituted C 6 -C 30 Aryl, aryl may be monocyclic aryl or polycyclic aryl. In some embodiments, the substituted or unsubstituted aryl group may be a substituted or unsubstituted C 6 -C 20 Aryl, substituted or unsubstituted C 6 -C 12 Aryl groups. Wherein the substituent in the substituted aryl group may be deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic group, acyl group, substituted or unsubstituted alkyl group, cycloalkyl group, alkoxy group, aryl group, aryloxy group, heteroaryl group, etc. The substituted or unsubstituted monocyclic aryl group may be, for example, phenyl, deuterated phenyl, tritiated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, t-butyl-substituted phenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated t-butyl-substituted phenyl, or the like. Wherein the polycyclic aryl group may be of a condensed ring type or a non-condensed ring type (e.g., biphenyls). In particular, the substituted or unsubstituted polycyclic aryl groups of biphenyls may be, but are not limited to, substituted or unsubstituted biphenyl, terphenyl, diphenyl ether A group (two benzene rings linked through an oxygen atom). Among them, the substituted polycyclic aryl groups may be exemplified by deuterated biphenyl groups, tritiated biphenyl groups, methyl-substituted biphenyl groups, ethyl-substituted biphenyl groups, isopropyl-substituted biphenyl groups, t-butyl-substituted biphenyl groups, deuterated methyl-substituted biphenyl groups, deuterated ethyl-substituted biphenyl groups, deuterated isopropyl-substituted biphenyl groups, deuterated t-butyl-substituted biphenyl groups, deuterated terphenyl groups, tritiated terphenyl groups, methyl-substituted diphenyl ether groups, and the like. The substituted or unsubstituted polycyclic aryl group of condensed ring type may be a substituted or unsubstituted naphthyl group, anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, spirofluorenyl group, 9-dimethylfluorenyl group, binaphthyl fluorenyl group, or the like.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted aryloxy group may be a substituted or unsubstituted C 6 -C 30 An aryloxy group; the aryloxy group may be a monocyclic aryloxy group or a polycyclic aryloxy group. In some embodiments, the substituted or unsubstituted aryloxy group may be a substituted or unsubstituted C 6 -C 20 Aryloxy, substituted or unsubstituted C 6 -C 12 An aryloxy group. Specifically, an aryloxy group obtained by oxidizing the above-mentioned aryl group can be mentioned.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C 3 -C 30 Heteroaryl groups. In some embodiments, the substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C 5 -C 20 Heteroaryl, substituted or unsubstituted C 6 -C 12 Heteroaryl groups. The heteroatoms in the heteroaryl group may be selected from one or more of N, O, S, se atoms. The substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, a substituted or unsubstituted benzo heterocycle, a substituted or unsubstituted heterocyclo heterocycle, or the like. The substituted or unsubstituted heteroaryl group may be, for example, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, benzofuryl, dibenzofuryl, tert-butyl-substituted dibenzofuryl, thienyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, xanthonylTriazinyl, phenyl-substituted triazinyl, and the like.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted heteroaryloxy group may be a substituted or unsubstituted C 3 -C 30 A heteroaryloxy group. In some embodiments, the substituted or unsubstituted heteroaryloxy group may be a substituted or unsubstituted C 5 -C 20 Heteroaryloxy, substituted or unsubstituted C 6 -C 12 A heteroaryloxy group. The heteroatoms in the heteroaryloxy group may be selected from one or more of N, O, S, se atoms. Specifically, the heteroaryloxy group may be obtained by oxidizing the heteroaryl group described above, and will not be described herein.
In an embodiment of the application, the substituted or unsubstituted alkylamino group is an amino group substituted with a substituted or unsubstituted alkyl group. The substituted or unsubstituted alkylamino group may be a substituted or unsubstituted C 1 -C 30 An alkylamino group. In some embodiments, the substituted or unsubstituted alkylamino group may be a substituted or unsubstituted C 2 -C 20 Alkylamino, substituted or unsubstituted C 3 -C 12 An alkylamino group. Illustratively, the substituted or unsubstituted alkylamino group may be ethylamino or the like.
In an embodiment of the present application, the substituted or unsubstituted arylamine group is an amino group substituted with a substituted or unsubstituted aryl group, and specifically may be an amino group substituted with the above-mentioned substituted or unsubstituted aryl group. The substituted or unsubstituted arylamino group may be a substituted or unsubstituted C 6 -C 30 An arylamine group. In some embodiments, the substituted or unsubstituted arylamine group may be a substituted or unsubstituted C 6 -C 20 Arylamine group, substituted or unsubstituted C 7 -C 15 An arylamine group. By way of example, the substituted or unsubstituted arylamino group may be, for example, a phenylamino group, a dimethylphenylamino group, a tert-butylbenzene substituted amino group, a di-tert-butylphenylamino group, or the like.
In an embodiment of the present application, the substituted or unsubstituted heteroaryl amino group is an amino group substituted with a substituted or unsubstituted heteroaryl group, and specifically may be an amino group substituted with a substituted or unsubstituted heteroaryl group. The substituted or unsubstituted heteroaromatic amine groups may be substituted or unsubstitutedC 3 -C 30 Heteroaromatic amine groups. In some embodiments, the substituted or unsubstituted heteroaromatic amine group may be a substituted or unsubstituted C 5 -C 20 Heteroaromatic amine groups, substituted or unsubstituted C 6 -C 12 Heteroaromatic amine groups.
In the embodiment of the present application, the above-mentioned substituted or unsubstituted borane group may be a borane group, a phenyl-substituted borane group, or the like, and the substituent in the substituted borane group may be a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an acyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, or the like.
In an embodiment of the present application, the substituted or unsubstituted silyl group may be trimethylsilyl or the like. In an embodiment of the present application, the substituted or unsubstituted aromatic silicon group may be a phenyl silicon group or the like.
In an embodiment of the application, C containing at least one heteroatom of O, N, S, B, P, F in addition to the above groups 1 -C 18 The electron withdrawing group of (c) may be, but is not limited to, a substituted or unsubstituted imide group, a substituted or unsubstituted amide group, a cyano group, a nitro group, or a hydroxyl group. Wherein the substituents in the substituted imide group, the substituted amide group may be, but are not limited to, deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic acid group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryl group.
In an embodiment of the application, R 1 、R 2 Each occurrence of which may be independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a fluoropropyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a phenyl-substituted tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a,Tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, tert-butyl-substituted dibenzofuryl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted carbazolyl, tert-butyl-substituted N-carbazolylphenyl, 9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl tertiary butyl substituted phenyl, biphenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tertiary butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tertiary butyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated ethyl substituted biphenyl, deuterated isopropyl substituted biphenyl, deuterated tertiary butyl substituted biphenyl, phenyl substituted amino, tertiary butyl benzene substituted amino, tertiary butyl substituted dibenzofuranyl, phenyl substituted tertiary butyl, xanthone, triazinyl, phenyl substituted triazinyl, borane, phenyl substituted borane, methoxy or tertiary butoxy.
In some embodiments of the application, R is partially adjacent 1 Connected in a ring, the rest R 1 The optional groups may be independently selected from the above. Wherein, when adjacent R 1 When connected in a ring (i.e., adjacent Z is connected in a ring), the ring structure formed includes, but is not limited to, any of the formulae (a) to (i):
in the formulae (a) to (i), the positions of the marks are connection positions, and the structures of the formulae (a) to (i) are connected in a parallel ring manner through the positions of the marks. Wherein, the case corresponding to the formula (a) can be seen in the compound shown in the following formula (7); the case corresponding to formula (b) can be seen in the compounds of formula (9) below; in some embodiments of the present application, the substitutable position of the structures of formulas (a) to (i) may have a substituent, for example, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an acyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a light-emitting structure of formula (a) or the like may be advantageous.
In some embodiments of the application, R 1 And R is R 2 Connected in a ring, and can participate in the ring formation by one or more R 1 The remainder not participating in cyclization R 1 The optional groups may be independently selected from the above. Wherein when R is 2 With adjacent R 1 When connected in a ring (i.e., Y is connected to adjacent Z) the ring structure formed may be a structure comprising formulae (a) to (D):
r in formula (A) 5 Is a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, n is an integer of 0 to 4; in the formulae (a) to (D), the positions of the marks are connection positions, and the structures of the formulae (a) to (D) are connected in parallel by the positions of the marks. Wherein, correspond toThe compound of the formula (A) may be a compound represented by the formula (II-A), or a compound represented by the following formula (115);
in the formula (II-A), the selection of Y is as defined above.
In the embodiment of the present application, the compounds represented by the formulas (I) to (X) may specifically be any one including compounds represented by the structural formulas (1) to (268):
the compound provided by the embodiment of the application can be prepared by adopting various chemically realizable modes.
In some embodiments of the present application, the compounds of formula (I) may be synthesized according to the following steps:
(1) Raw material 1A was added to a reaction vessel, and raw material 2A, tBuona (sodium t-butoxide), tBu, was added 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating.Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1A;
(2) The intermediate 1A was charged into a reaction vessel, and the starting materials 3A, tBuONa, tBu were further charged 3 P,Pd 2 (dba) 3 And para-xylene, followed by nitrogen substitution, heating and stirring. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 2A;
(3) Adding the intermediate 2A into a reaction vessel, and sequentially adding raw materials 4A, tBuONa and tBu 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 3A;
(4) Adding the intermediate 3A into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating and stirring, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et (diisopropylethylamine), continuing to stir under reflux, followed by direct spin-drying, and separating by silica gel column chromatography to give the compound of formula (I). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (II) may be synthesized according to the following steps:
(1) Raw material 1B was added to a reaction vessel, followed by raw material 2B, tBuona (sodium t-butoxide), tBu 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1;
(2) The intermediate 1B was charged into a reaction vessel, followed by the addition of the starting materials 3B, tBuona, tBu 3 P,Pd 2 (dba) 3 And para-xylene, followed by nitrogen substitution, heating and stirring. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 2B;
(3) Adding the intermediate 2B into a reaction vessel, and sequentially adding the raw materials 4B,tBuONa,tBu 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 3B;
(4) Adding the intermediate 3B into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating and stirring, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing to stir at 180 ℃ under reflux for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to give the compound of formula (II). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (III) may be synthesized according to the following steps:
(1) Adding the raw material 1C into a reaction vessel, adding the raw material 2C, tBuona (sodium tert-butoxide) and tBu 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1C;
(2) The intermediate 1C was added to the reaction vessel, followed by addition of the starting materials 3C, tBuona, tBu 3 P,Pd 2 (dba) 3 And para-xylene, followed by nitrogen substitution, heating and stirring. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 2C;
(3) Adding the intermediate 2C into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating, refluxing, stirring overnight, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (III). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (IV) may be synthesized according to the following steps:
(1) Adding the raw material 1D into a reaction vessel, adding the raw material 2D, tBuona (sodium tert-butoxide) and tBu 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1D;
(2) Adding the intermediate 1D into a reaction vessel, and adding the raw materials 3D and K 2 CO 3 ,Pd(PPh 3 ) 4 (Tetrakis (triphenylphosphine) palladium) and DMF, H 2 O, then replace nitrogen, heat and stir. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid through column chromatography to obtain an intermediate 2D;
(3) Adding the intermediate 2D into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating, refluxing, stirring overnight, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (IV). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (V) may be synthesized according to the following steps:
(1) Adding the raw material 1E into a reaction vessel, and adding the raw material 2E, tBuona (sodium tert-butoxide) and tBu 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1E;
(2) Adding intermediate 1E into a reaction vessel, adding o-ringDichlorobenzene, nitrogen blanket, followed by BBr addition 3 Heating, refluxing, stirring overnight, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (V). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (VI) may be synthesized according to the following steps:
(1) Raw material 1F was added to a reaction vessel, and raw material 2F, tBuona (sodium t-butoxide), tBu, was added 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1F;
(2) Adding the intermediate 1F into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating, refluxing, stirring overnight, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (VI). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (VII) may be synthesized according to the following steps:
(1) Adding the raw material 1G into a reaction vessel, and adding the raw materials 2G and K 2 CO 3 CuI, L-pro line (L-Proline) and p-xylene, followed by nitrogen substitution, heating and stirring. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1G;
(2) Adding the intermediate 1G into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and cooling with ice water bathAdding nBu-Li after warming, stirring at room temperature for reaction, cooling with ice water bath, adding BBr 3 Stirring overnight at room temperature, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (VII). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (VIII) may be synthesized according to the following steps:
(1) Adding the raw material 1H into a reaction vessel, adding the raw material 2H, tBuona (sodium tert-butoxide) and tBu 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1H;
(2) Adding the intermediate 1H into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating, refluxing, stirring overnight, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (VIII). The reaction process is as follows:
In some embodiments of the present application, the compound of formula (IX) may be synthesized according to the following procedure:
(1) Adding the raw material 1I into a reaction vessel, and adding the raw material 2,K 2 CO 3 CuI, L-pro line (L-Proline) and p-xylene, followed by nitrogen substitution, heating and stirring. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1I;
(2) Adding the intermediate 1I into a reaction vessel, adding o-dichlorobenzeneNitrogen protection, cooling with ice water bath, adding nBu-Li, stirring at room temperature, cooling with ice water bath, and adding BBr 3 Stirring overnight at room temperature, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to give the compound of formula (IX). The reaction process is as follows:
in some embodiments of the present application, the compound of formula (X) may be synthesized according to the following steps:
(1) Adding the raw material 1J into a reaction vessel, adding the raw material 2J, tBuona (sodium tert-butoxide) and tBu 3 P (tri-tert-butylphosphine), pd 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) and para-xylene, followed by nitrogen substitution, and stirring with heating. Concentrating the reaction liquid after the reaction is finished, and separating the reaction liquid by column chromatography to obtain an intermediate 1J;
(2) Adding the intermediate 1J into a reaction vessel, adding o-dichlorobenzene, protecting with nitrogen, and then adding BBr 3 Heating, refluxing, stirring overnight, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing stirring and refluxing for 3h, followed by direct spin-drying, and separating by silica gel column chromatography to obtain the compound represented by formula (X). The reaction process is as follows:
the compound provided by the embodiment of the application has higher fluorescence quantum efficiency and narrower half-peak width, can be used in various electronic devices with functions of luminescence, display, illumination and the like, and improves the device performance. The embodiment of the application provides application of the compound and the salt thereof in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, light-emitting electrochemical cells, photoelectric converters, light-emitting devices, image sensors, lasers or photosensitive devices. In particular, the above compounds can be used as light emitting materials in the above devices. For example, the compound provided by the embodiment of the application can be applied to an organic electroluminescent device, can be used as a material of a luminescent layer of the organic electroluminescent device, and can improve the luminescent efficiency, luminescent stability, color purity, service life and the like of the device. Specifically, the compound provided by the embodiment of the application has narrow half-peak width, high fluorescence quantum yield and proper HOMO and LUMO energy levels, and can be used as a luminescent layer doping material of an organic electroluminescent device, so that the device efficiency, the luminescent color purity and the device stability are improved; the compound of the embodiment of the application is introduced into the light-emitting layer as a doping material, so that the exciton sensitization effect can be realized, and the efficiency and the service life of the device are effectively improved.
The embodiment of the application provides an electronic device, which comprises the compound disclosed by the embodiment of the application. The electronic device may be, for example, an organic electroluminescent device, an organic light emitting field effect transistor, an organic photovoltaic device, a light emitting electrochemical cell, or the like. Referring to fig. 1, fig. 1 is a schematic structural diagram of an organic electroluminescent device (OLEDs) 100 according to an embodiment of the application. The organic electroluminescent device 100 shown in fig. 1 includes an anode 10, a cathode 20, and a functional layer 30 between the anode 10 and the cathode 20, the functional layer 30 including a light emitting layer 301. The light emitting layer 301 includes the above-described compound provided in the embodiment of the present application.
In some embodiments of the present application, the light emitting layer 301 contains a host material and a dopant material (also referred to as a "guest material"), wherein the dopant material includes at least one compound of the present application described above. The compound is used as a doping material of the light-emitting layer 301, can play a role of sensitizing excitons, and improves the light-emitting efficiency of the device; the half-peak width of the compound is narrower, so that the luminous color purity of the device can be improved, the color gamut of the device is improved, and the device can meet the display standard with higher requirements; the compound has proper HOMO energy level and LUMO energy level, can effectively reduce the triplet state exciton concentration of a main body material, reduce the quenching probability of the triplet state exciton, and can effectively improve the stability and the service life of a device.
In the embodiment of the present application, the doping material of the light emitting layer 301 may be a material including only one or more of the above-described compounds of the present application; it is also possible to include one or more of the above-described compounds of the application and other doping materials. The other doping materials can be various doping materials available in the field, and can be specifically selected according to actual needs.
In an embodiment of the present application, the host material of the light emitting layer 301 may include one or more kinds, and the host material may be various host materials available in the art, and may be specifically selected according to actual needs.
In some embodiments of the present application, the light emitting layer 301 includes two host materials, which may be referred to as a first host material and a second host material, respectively, at least one of which is a Thermally Activated Delayed Fluorescence (TADF) material. In this embodiment, the host material of the light-emitting layer is formed by matching two materials, the energy transfer efficiency between the host material and the compound serving as the doping material is high, the light-emitting potential of the compound can be fully exerted, and the light-emitting efficiency of the device is high.
In the embodiment of the present application, the constituent materials of the anode 10 and the cathode 20 are conductive materials, and may be independently selected from conductive metals, conductive metal oxides, conductive polymers, and the like. Wherein, the conductive metal can comprise one or more of metal simple substances such as magnesium (Mg), aluminum (Al), gold (Au), silver (Ag), platinum (Pt), target (Pd) and the like and alloys thereof; the conductive metal oxide includes, but is not limited to, one or more of Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), aluminum doped zinc oxide (AZO), fluorine doped tin dioxide (FTO), phosphorus doped tin dioxide (PTO), etc.; conductive polymers include, but are not limited to, polythiophenes, polypyrroles, polyanilines, and the like.
In an embodiment of the present application, referring to fig. 1, the functional layer 30 further includes a first carrier transport layer 302 between the anode 10 and the light emitting layer 301, and a second carrier transport layer 303 between the cathode 20 and the light emitting layer 301. The first carrier transport layer 302 may include one or more of a hole injection layer 3021, a hole transport layer 3022, and an electron blocking layer 3023 between the anode 10 and the light emitting layer 301. Wherein the hole injection layer 3021 is located between the anode 10 and the hole transport layer 3022, and the electron blocking layer 3023 is located between the light emitting layer 301 and the hole transport layer 3022. The second carrier transport layer 303 may be one or more of an electron injection layer 3031, an electron transport layer 3032, and a hole blocking layer 3033 between the cathode 20 and the light emitting layer 301. Wherein the electron injection layer 3031 is located between the cathode 20 and the electron transport layer 3032, and the hole blocking layer 3033 is located between the cathode 20 and the hole transport layer 3022. In some embodiments, as shown in fig. 1, the organic electroluminescent device 100 includes an anode 10, a hole injection layer 3021, a hole transport layer 3022, an electron blocking layer 3023, a light emitting layer 301, a hole blocking layer 3033, an electron transport layer 3032, and an electron injection layer 3031 that are disposed in this order. Note that each layer of the functional layer 30 is not necessarily required, but the light-emitting layer 301 is necessarily required. For example, the functional layer 30 may include a stacked structure of "light emitting layer 301/electron transporting layer 3032" or a stacked structure of "light emitting layer 301/electron injecting layer 3031" or a stacked structure of "hole injecting layer 3021/light emitting layer 301/electron transporting layer 3032" or a stacked structure of "hole injecting layer 3021/light emitting layer 301/electron injecting layer 3031" or a stacked structure of "hole transporting layer 3022/light emitting layer 301/electron transporting layer 3032" or a stacked structure of "hole injecting layer 3021/hole transporting layer 3022 or electron blocking layer 3023/light emitting layer 301/hole blocking layer 3033 or electron transporting layer 3032/electron injecting layer 3031" or a stacked structure of "hole injecting layer 3021/electron blocking layer 3022/electron blocking layer 3023/light emitting layer 301/hole blocking layer 3033/electron transporting layer 3032" in this order. Where "/" indicates the demarcation of the layers. In the present application, the thickness of each of the above layers is not particularly limited, and may be determined according to actual needs by those skilled in the art. The materials of the above layers are conventional choices in the art, and the present application is not particularly limited.
In some embodiments, the organic electroluminescent device 100 may further have a substrate 40 (as shown in fig. 1). The substrate 40 may be a side of the anode 10 away from the functional layer 30 (as shown in fig. 1), in which case the organic electroluminescent device 100 is a bottom emission device. The substrate 40 may also be located on a side of the cathode 20 away from the functional layer 30, where the organic electroluminescent device 100 is a top-emission device comprising the cathode 20, the functional layer 30 and the anode 10 sequentially disposed on the substrate 40. The substrate 40 may be used as a support portion of the entire organic electroluminescent device 100, and may be made of quartz, glass, elemental silicon, metal, plastic, or the like. In some embodiments, the substrate 40 is glass or plastic that is transparent to light. The shape of the substrate 40 may be formed in a plate shape, a film shape, a sheet shape, or the like, for example, depending on the specific application. The thickness of the substrate 40 is not particularly limited.
In the present application, the process for preparing each of the anode 10, the cathode 20 and the functional layer 30 is not particularly limited, and may be prepared by physical vapor deposition, chemical vapor deposition, coating, or the like. Wherein, the physical vapor deposition method can comprise one or more of vacuum evaporation method (such as resistance evaporation source evaporation method, electron beam evaporation source evaporation method, pulse laser deposition method, etc.), sputtering method (such as magnetron sputtering method), etc.; coating methods may include solution spin coating, dip coating, knife coating, spray coating, roll coating, ink jet printing, screen printing, and the like. In general, the anode 10 and the cathode 20 may be prepared by a vacuum evaporation method, and each layer of the functional layer 30 may be prepared by a vacuum evaporation method or a coating method. Taking the preparation of the organic electroluminescent device shown in fig. 1 as an example, the anode 10 may be formed on the substrate 40, then the functional layer 30 including the light emitting layer 301 may be sequentially formed on the anode 10, and then the cathode 20 may be formed on the functional layer 30. In other embodiments of the present application, the cathode 20, the functional layer 30 including the light emitting layer 301, and then the anode 10 may be sequentially formed on the substrate 40.
Referring to fig. 2, the embodiment of the present application further provides a display apparatus 200, where the display apparatus 200 includes the electronic device described above in the embodiment of the present application, and may specifically include the organic electroluminescent device 100 described above.
In an embodiment of the present application, the display device 200 may be a visual display device in any product or component having a display function, such as a mobile phone, a tablet computer, a notebook computer, a wearable device (e.g., a smart watch, a smart bracelet, etc.), a television, a digital camera, a camcorder, a player, a micro-display device (e.g., smart glasses, virtual Reality (VR) device, augmented Reality (Augmented Reality, AR) device, a telephone, a printer, a vehicle, a home appliance, a billboard, an information board, an automobile center control screen, etc.
The embodiment of the application also provides a lighting device, which includes the electronic device according to the embodiment of the application, and specifically may include the organic electroluminescent device 100. Examples of the lighting device include an automobile tail lamp, an automobile head lamp, an automobile fog lamp, an indoor lighting device (including a commercial or household lamp, a ceiling lamp, etc.), an outdoor lighting device (such as a street lamp), a backlight of a liquid crystal display device, and the like, using an organic electroluminescent device.
Referring to fig. 3, an embodiment of the present application further provides an electronic device 300, where the electronic device 300 includes the display apparatus 200 described above in the embodiment of the present application. The electronic device 300 may be any electronic product with display function, such as a mobile phone, a tablet computer, a notebook computer, a wearable device (e.g., a smart watch, a smart bracelet, etc.), a television, a digital camera, a camcorder, a player, a micro-display device (e.g., smart glasses, virtual Reality (VR) device, augmented Reality (Augmented Reality, AR) device, a telephone, a printer, a vehicle, a home appliance, a billboard, an information board, an automobile center control screen, etc.
The following examples are provided to further illustrate embodiments of the application.
Example 1
Synthesis of a compound having the structural formula of formula (4) (hereinafter simply referred to as compound 4):
(1) Raw material 1a was added to the flask, and raw materials 2a, tBuona, tBu were added in this order 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the completion of the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 1a.
(2) The intermediate 1a was added to the flask, and the starting materials 3a, tBuona, tBu were added in this order 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 2a.
(3) The intermediate 2a was added to the flask, and the starting materials 4a, tBuona, tBu were added sequentially 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 3a.
(4) Adding intermediate 3a into bottle, adding o-dichlorobenzene, protecting with nitrogen, and adding BBr 3 Heating and stirring, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing to stir with heating until the reaction is completed, followed by direct spin-drying, and isolating compound 4 by column chromatography on silica gel.
The reaction process of the synthesis process is as follows:
FIG. 4 is a LC-MS (liquid chromatography-mass spectrometry) spectrum of compound 4 prepared in example 1 of the present application. MS: measurement value: 849.45[ M ] + H] + Theoretical value: 848.45. FIGS. 5 and 6 are, respectively, a hydrogen nuclear magnetic resonance spectrum and a carbon nuclear magnetic resonance spectrum of the compound 4 prepared in example 1 of the present application.
Example 2
Synthesis of a compound having the structural formula (32) (hereinafter simply referred to as compound 32):
(1) Raw material 1b was added to the flask, and raw materials 2A, tBuona, tBu were added sequentially 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 1b.
(2) Intermediate 1b was added to the flask and starting materials 3B, tBuona, tBu were added sequentially 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 2b.
(3) Intermediate 2b was added to the flask and starting materials 4a-1, tBuONa, tBu were added sequentially 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 3b.
(4) Adding intermediate 3b into bottle, adding m-dichlorobenzene, protecting with nitrogen, and adding BBr 3 Heating and stirring, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing to stir with heat until the reaction is complete, followed by direct spin-drying, and isolating compound 32 by column chromatography on silica gel. The nuclear magnetic resonance hydrogen spectrum data of the compound 32 prepared in this example is shown in fig. 8.
The reaction process of the synthesis process is as follows:
example 3
Synthesis of a compound having the structural formula (139) (hereinafter simply referred to as compound 139):
(1) Raw material 1c was added to the flask, and raw materials 2c, tBuona, tBu were added sequentially 3 P,Pd 2 (dba) 3 Para-xylene, followed by nitrogen substitution, was heated and stirred. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 1c.
(2) Intermediate 1c was added to the flask, dissolved in THF, and added to feed B (OMe) under ice-water bath 3 Reacting at normal temperature for 1H, cooling to-78 ℃, dropwise adding nBu-Li, reacting for 2H, neutralizing alkali in the system by adopting acetic acid, heating to 0 ℃, and dropwise adding H 2 O 2 Intermediate 2c was isolated by column chromatography on silica gel.
(3) Adding the intermediate 2c into a flask, and sequentially adding the raw materials 3c and K 2 CO 3 Then replacing nitrogen, adding dry DMF solvent, stirring at normal temperature for reaction untilThe reaction was completed. After the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain intermediate 3c.
(4) Adding intermediate 3c into bottle, adding m-dichlorobenzene, protecting with nitrogen, and adding BBr 3 Heating and stirring, then reducing the temperature to 0 ℃, adding iPr 2 -N-Et, continuing to stir with heat until the reaction is complete, followed by direct spin-drying, and isolating compound 139 by column chromatography on silica gel. The nuclear magnetic hydrogen spectrum data of the compound 139 prepared in this example is shown in fig. 10.
The reaction process of the synthesis process is as follows:
the compounds 4, 32 and 139 prepared in example 1 were subjected to ultraviolet absorption spectrum test and fluorescence spectrum test, and the detection results are shown in table 1 and fig. 7, 9 and 11. FIG. 7 is a graph showing the ultraviolet absorption spectrum and fluorescence spectrum of Compound 4 in example 1 of the present application. Wherein, the absorption peak is tested by a double-beam ultraviolet visible spectrophotometer; the luminescence peak and FWHM (full width at half maximum) are obtained by testing with a fluorescence spectrometer under the state of a film; stokes shift (Stokes shift) refers to the red shift of the fluorescence spectrum compared to the corresponding absorption spectrum, calculated by subtracting the absorption peak from the emission peak. The luminescence peak and FWHM of comparative example were obtained by purchasing commercial Ir (ppy) 3 The test film was obtained.
TABLE 1
As can be seen from the data in table 1, compound 4, compound 32, compound 139 have a small stokes shift (only 22 nm), indicating that the material is well sensitized by a sensitizing material that emits visible light. In addition, compound 4, compound 32, compound 139 have a very narrow half-width (fwhm=27 nm), and are doped as a doping material in a host material to prepare an OLED device, which can realize narrow-width emission, thereby realizing high color purity.
Ir (ppy) is used as a commercial phosphorescent material 3 As a comparative example (all named fac-Tris (2-phenylpyridine) iridium (III)), it can be seen that the Stokes shift of the compounds of the examples of the present application is much smaller than that of the commercial phosphorescent material Ir (ppy) 3 The compound provided by the application can be used for preparing devices not only through a common doping system, but also through a sensitization mode, and the comparative example has no such advantage, and besides, the FWHM of the compound spectrum is far narrower than that of Ir (ppy) of the comparative example 3 The material can effectively improve the color gamut of the device and the luminous efficiency of the device.
The effect of the above-synthesized compound of the present application in application to an organic electroluminescent device will be described in detail below with reference to device examples 1 and 2 and device comparative example 1.
Device example 1
An organic electroluminescent device, as shown in fig. 12, comprises a substrate 40 (specifically, a transparent glass substrate), and an ITO anode 10 (150 nm in thickness), a first hole transport layer 3022a (TAPC material, 30nm in thickness), a second hole transport layer 3022b (TCTA material, 10nm in thickness), an electron blocking layer 3023 (mCP material, 10nm in thickness), a light emitting layer 301 (PPF as a host material, DACT-II as a thermally delayed fluorescent sensitizer material, a compound 4 as a fluorescent dopant material, a host material, a sensitizer material, a compound 4 in a mass ratio of 68:30:2, a light emitting layer film thickness of 20 nm), a hole blocking layer 3033 (PPF material, 5nm in thickness), an electron transport layer 3032 (BPhen material, 40nm in thickness), an electron injection layer 3031 (LiF layer, 1nm in thickness), and a cathode 20 (Al, 100nm in this order.
The structural formula of the related materials is shown below.
The preparation process of the OLED light-emitting device comprises the following steps: the ITO anode 10 is washed, i.e., sequentially subjected to a cleaning agent washing, a pure water washing, and drying, and then subjected to an ultraviolet-ozone washing to remove organic residues on the transparent ITO surface. On the ITO anode 10 after the above washing, TAPC having a film thickness of 30nm was deposited as the first hole transport layer 3022a by a vacuum deposition apparatus. Subsequently, TCTA having a thickness of 10nm was deposited as the second hole transport layer 3022b. Subsequently, mCP having a thickness of 10nm was evaporated as an electron blocking layer 3023. After the evaporation of the electron blocking material is finished, a luminescent layer 301 of the OLED luminescent device is manufactured, a PPF main body material and DACT-II are used as a thermal delay fluorescence sensitizer material, a compound 4 is used as a fluorescence doping material, the main body material, the sensitizer material and the compound 4 are mixed according to the mass ratio of 68:30:2, and the thickness of the luminescent layer 301 is 20nm. On the light-emitting layer 301, PPF was continuously vacuum-deposited to a film thickness of 5nm, which was a hole blocking layer 3033. On the hole blocking layer 3033, BPhen 40nm thick was continuously vacuum-deposited as the electron transport layer 3032 and LiF 1nm was continuously deposited as the electron injection layer 3031, and an Al electrode layer having a film thickness of 100nm was formed on the electron injection layer 3031 by a vacuum deposition apparatus, and this layer was the cathode 20.
Device example 2
Device embodiment 2 differs from device embodiment 1 only in the light-emitting layer 301. In this embodiment, the light emitting layer 301 uses PPF host material, DACT-II as the thermally delayed fluorescence sensitizer material, compound 4 as the fluorescence dopant material, and the mass ratio of host material, sensitizer material, and compound 4 is 78:20:2.
Device comparative example 1 differs from device example 1 only in that CBP and Ir (ppy) were used for the light-emitting layer 301 3 Mixing and blending according to the mass ratio of 97:3.
After the OLED light emitting device was completed as described above, the anode and cathode were connected using a well-known driving circuit, and the luminance voltage, external quantum efficiency and half-height bandwidth of the device were measured. The results of the tests of the luminance voltage, external quantum efficiency and half-height bandwidth of the obtained device are shown in table 2 and fig. 13, and fig. 14 and fig. 15. Wherein, FIG. 13 is a luminescence spectrum of the device example 1 and the device example 2 of the present application; FIG. 14 is a plot of current density versus voltage versus luminance for devices of device example 1 and device example 2 of the present application; fig. 15 is a luminance-external quantum efficiency plot for the devices of device example 1 and device example 2 of the present application. The device luminance voltage can be found from fig. 14, and the external quantum efficiency of the device can be found from fig. 15.
TABLE 2
Note that: the device in table 2 was tested for brightness onset voltage, external quantum efficiency, and peak luminescence using an IVL (current-voltage-brightness) test system; the lighting voltage is 1cd/m 2 The external quantum efficiency and the luminescence peak value are all 1000cd/m under the test of brightness 2 And (5) testing.
As can be seen from the device data results in table 2, compared with the device prepared from the known material in device comparative example 1, the OLED device prepared from the compound of the embodiment of the present application has improved external quantum efficiency, greatly reduced half-height bandwidth of the light-emitting peak of the device, and improved color purity of the device. The compound provided by the embodiment of the application has a relatively high narrow spectrum FWHM as a doping material, can effectively improve the color gamut of the device, improves the luminous efficiency of the device, and can also improve the luminous stability. In addition, the OLED device prepared by the compound disclosed by the embodiment of the application has lower lighting voltage.
Claims (19)
1. A compound characterized in that the compound is a multimer of the structure of formula (one):
wherein M is 2 、M 3 A substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring, respectively; z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted alkenyl, taken Substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted borane, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or C containing at least one heteroatom other than those described above O, N, S, B, P, F 1 -C 18 Electron withdrawing groups of (C), adjacent R 1 Can be connected into a ring.
2. The compound of claim 1, wherein said compound is a multimer of 2 to 6 of said structures of formula (one).
3. The compound according to claim 1 or 2, wherein the compound has any one of the structural formulae (I) to (X):
in the formulae (I) to (X), Z is C (R) 1 ) Y is NR 2 O, S or Se; r is R 1 、R 2 Each occurrence is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, and a substituted or unsubstituted heterocycloalkyl group Substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted borane, substituted or unsubstituted silane, substituted or unsubstituted aromatic silicon, or C containing at least one heteroatom in O, N, S, B, P, F other than the above 1 -C 18 Electron withdrawing groups of (C), adjacent R 1 Can be connected into a ring, R 2 Can be adjacent to R 1 Connected into a ring.
4. A compound according to any one of claims 1 to 3, wherein the substituents in the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted heterocycloalkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted alkoxy, substituted aryloxy, substituted aryl, substituted heteroaryl, substituted heteroaryloxy, substituted alkylamino, substituted arylamino, substituted heteroarylamino, substituted borane, substituted silyl, substituted polysilyl comprise one or more of deuterium atoms, tritium atoms, halogen atoms, cyano, nitro, carboxyl, sulfonic acid groups, acyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups.
5. The compound of any one of claims 1-4, wherein the substituted or unsubstituted alkyl is substituted or unsubstituted C 1 -C 30 An alkyl group; the substituted or unsubstituted cycloalkyl is substituted or unsubstituted C 3 -C 30 Cycloalkyl; the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C 2 -C 30 A heterocycloalkyl group; the substituted or unsubstituted alkenyl group is a substituted or unsubstituted C 2 -C 30 Alkenyl groups; the substituted or unsubstituted cycloalkenyl is substituted or unsubstituted C 3 -C 10 A cycloalkenyl group; the substituted or unsubstituted heterocycloalkenyl is substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl; the substituted or unsubstituted alkynyl is substituted or unsubstituted C 2 -C 30 Alkynyl; the substituted or unsubstituted cycloalkynyl group is a substituted or unsubstituted C 6 -C 10 A cycloalkynyl group; the substituted or unsubstituted heterocyclylalkynyl is a substituted or unsubstituted C 5 -C 10 Heterocyclic alkynyl; the substituted or unsubstituted alkoxy is substituted or unsubstituted C 1 -C 30 An alkoxy group; the substituted or unsubstituted aryloxy group is a substituted or unsubstituted C 6 -C 30 An aryloxy group; the substituted or unsubstituted aryl is substituted or unsubstituted C 6 -C 30 An aryl group; the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C 3 -C 30 Heteroaryl; the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C 3 -C 30 A heteroaryloxy group; the substituted or unsubstituted alkylamino is substituted or unsubstituted C 1 -C 30 An alkylamino group; the substituted or unsubstituted arylamine group is a substituted or unsubstituted C 6 -C 30 An arylamine group; the substituted or unsubstituted heteroaromatic amine group is a substituted or unsubstituted C 3 -C 30 Heteroaromatic amine groups.
6. A compound according to any one of claims 1 to 5 wherein said C containing at least one heteroatom of O, N, S, B, P, F in addition to said groups 1 -C 18 Comprises a substituted or unsubstituted imide group, a substituted or unsubstituted amide group, a cyano group, a nitro group or a hydroxyl group.
7. The compound of any one of claims 1-6, wherein R 1 、R 2 Each occurrence is independently a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, adamantyl group, methyl group, deuteromethyl group, tritium methyl group, fluoropropyl group, trifluoromethyl group, ethyl group, deuteration groupEthyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, phenyl-substituted tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyrenyl, pyridinyl, phenyl-substituted pyridinyl, quinolinyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, tert-butyl-substituted dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted carbazolyl, tert-butyl-substituted N-carbazolylphenyl 9, 9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, t-butyl-substituted phenyl, biphenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, t-butyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteroethyl-substituted phenyl, deuteroisopropyl-substituted phenyl, deuterated t-butyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroethyl-substituted biphenyl, deuteroisopropyl-substituted biphenyl, deuterated t-butyl-substituted biphenyl, phenyl-substituted amino, t-butylbenzene-substituted amino, t-butyl-substituted dibenzofuranyl, phenyl-substituted t-butyl, xanthonyl, triazinyl, phenyl-substituted triazinyl, boranyl, phenyl-substituted boranyl, methoxy or t-butoxy.
8. The compound of any one of claims 1-7, wherein adjacent R' s 1 When connected in a ring, the ring structure formed includes any one of the formulae (a) to (i):
in the formulae (a) to (i), the positions of the marks are connection positions, and the structures of the formulae (a) to (i) are connected in a parallel ring manner through the positions of the marks.
9. The compound of any one of claims 3-8, wherein R 2 Adjacent to said R 1 When connected in a ring, the ring structure formed includes structures represented by formulas (a) to (D):
r in formula (A) 5 Is a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, n is an integer of 0 to 4; in the formulae (a) to (D), the positions of the marks are connection positions, and the structures of the formulae (a) to (D) are connected in parallel by the positions of the marks.
10. The compound of claims 1-9, wherein the compound comprises any one of the compounds of structural formulas (1) - (268):
11. use of a compound according to any one of claims 1-10 and salts thereof in electroluminescent devices, organic light emitting field effect transistors, organic photovoltaic devices, light emitting electrochemical cells, photoelectric converters, light opening devices, image sensors, lasers, light sensing devices, biological imaging devices, paints, organic laser devices.
12. A light-emitting layer comprising the compound according to any one of claims 1 to 10.
13. The light-emitting layer according to claim 12, wherein the light-emitting layer comprises a host material and a doping material, and wherein the doping material comprises the compound.
14. An electronic device comprising the compound of any one of claims 1-10; or comprises a light emitting layer according to any of claims 12-13.
15. The electronic device of claim 14, wherein the electronic device comprises a cathode and an anode, and a functional layer between the cathode and the anode, the functional layer comprising the compound.
16. The electronic device of claim 14 or 15, wherein the electronic device comprises an electroluminescent device, an organic light emitting field effect transistor, an organic photovoltaic device, or a light emitting electrochemical cell.
17. A display device, characterized in that it comprises an electronic device according to any of claims 14-16; or comprises a light emitting layer according to any of claims 12-13.
18. An electronic device, characterized in that the electronic device comprises the display device of claim 17; or comprises an electronic device according to any of claims 14-16.
19. A lighting device comprising the electronic device of any one of claims 14-16; or comprises a light emitting layer according to any of claims 12-13.
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