CN117986278A - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
- Publication number
- CN117986278A CN117986278A CN202211338102.5A CN202211338102A CN117986278A CN 117986278 A CN117986278 A CN 117986278A CN 202211338102 A CN202211338102 A CN 202211338102A CN 117986278 A CN117986278 A CN 117986278A
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- substituted
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 125
- 125000003118 aryl group Chemical group 0.000 claims abstract description 87
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 79
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 28
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 150000001975 deuterium Chemical group 0.000 claims abstract description 17
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 229910052722 tritium Inorganic materials 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 229910052796 boron Inorganic materials 0.000 claims abstract description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 121
- 239000000463 material Substances 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 33
- 125000004104 aryloxy group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 23
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000002346 layers by function Substances 0.000 claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims description 19
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 19
- 125000001769 aryl amino group Chemical group 0.000 claims description 16
- 239000004305 biphenyl Substances 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 15
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000005264 aryl amine group Chemical group 0.000 claims description 9
- 238000013329 compounding Methods 0.000 claims description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 9
- 230000005669 field effect Effects 0.000 claims description 7
- 238000013086 organic photovoltaic Methods 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001454 anthracenes Chemical group 0.000 claims description 5
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000012984 biological imaging Methods 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 150000003233 pyrroles Chemical group 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000004431 deuterium atom Chemical group 0.000 claims 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims 1
- 150000003248 quinolines Chemical group 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- -1 methyl-substituted phenyl Chemical group 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 41
- 238000002360 preparation method Methods 0.000 description 34
- 238000001816 cooling Methods 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000012299 nitrogen atmosphere Substances 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
- 238000002189 fluorescence spectrum Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 229940125898 compound 5 Drugs 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 4
- 230000003190 augmentative effect Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000004074 biphenyls Chemical class 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- QFUYDAGNUJWBSM-UHFFFAOYSA-N 1-iodo-2-phenylbenzene Chemical group IC1=CC=CC=C1C1=CC=CC=C1 QFUYDAGNUJWBSM-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 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
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- XJWOWXZSFTXJEX-UHFFFAOYSA-N phenylsilicon Chemical group [Si]C1=CC=CC=C1 XJWOWXZSFTXJEX-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000004984 smart glass Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 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 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 description 1
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- CYPYTURSJDMMMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 CYPYTURSJDMMMP-UHFFFAOYSA-N 0.000 description 1
- WQVIVQDHNKQWTM-UHFFFAOYSA-N 1-tert-butyl-4-iodobenzene Chemical compound CC(C)(C)C1=CC=C(I)C=C1 WQVIVQDHNKQWTM-UHFFFAOYSA-N 0.000 description 1
- ZCABEQBKEKVYGK-UHFFFAOYSA-N 2,6-ditert-butyl-9H-carbazole Chemical compound C(C)(C)(C)C1=CC=2NC3=CC=C(C=C3C=2C=C1)C(C)(C)C ZCABEQBKEKVYGK-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 1
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic 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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 125000005577 anthracene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 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 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation 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
- 230000008020 evaporation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 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
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 125000005067 haloformyl group Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 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
- 239000004065 semiconductor Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003595 spectral effect Effects 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
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical class [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 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
- 230000000007 visual effect Effects 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1085—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with other heteroatoms
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- Y02E10/00—Energy generation through renewable energy sources
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- Electroluminescent Light Sources (AREA)
Abstract
The embodiment of the application provides an organic compound, which comprises a polycyclic structure formed by bonding at least one first structural unit shown in a formula (I) and at least one second structural unit shown in a formula (II); Wherein the A ring to the G ring are selected from a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aromatic heterocyclic ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is selected from c= O, N-R 2, O, S, se, P, P =o or p=s; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, and the like; r 1、R2、R3 may be linked to an adjacent group to form a ring. The organic compound has good luminescence property, can be applied to organic electroluminescent devices, and improves the device performance.
Description
Technical Field
The embodiment of the application relates to the technical field of organic luminescent materials, in particular to an organic compound and application thereof.
Background
The Organic luminescent material has good luminescence property, good adjustability, relatively flexible molecular design, and can be coated on various base materials to form a film, so that the Organic luminescent material is widely applied to the fields of Organic Light-Emitting Diodes (OLEDs), organic Light-Emitting field effect transistors, organic photovoltaic devices, light-Emitting 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, with the increasing display effect of display devices, higher requirements are also put on OLEDs luminescent materials, so that new organic luminescent materials have to be developed to meet the growing demands of OLEDs.
Disclosure of Invention
In view of the above, embodiments of the present application provide an organic compound having good light emitting performance, which can improve the performance of a light emitting device.
Specifically, a first aspect of the embodiment of the present application provides an organic compound including a polycyclic structure formed by bonding at least one first structural unit represented by formula (I) and at least one second structural unit represented by formula (II), the second structural unit being bonded to the first structural unit by at least substituting a part of the cyclic structure in the first structural unit;
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted aromatic heterocyclic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
The organic compound provided by the embodiment of the application comprises a brand new molecular skeleton formed by bonding a first structural unit shown in a formula (I) and a second structural unit shown in a formula (II), wherein the molecular skeleton is characterized in that the second structural unit shown in the formula (II) is introduced on the basis of the first structural unit shown in the formula (I), a seven-ring, eight-ring or nine-ring structure is constructed between three ring structures by the second structural unit shown in the formula (II), the second structural unit shown in the formula (II) has larger steric hindrance and higher rigidity, the number of freely rotating phenyl groups in the molecular skeleton can be reduced, the rigidity of the molecular skeleton is improved, the intermolecular aggregation of the compound in a solid state is restrained, and the conjugation length of the molecular skeleton can be limited, so that the molecular skeleton can simultaneously realize the molecular structure characteristics of large steric hindrance, high rigidity and low conjugation, and finally, a novel organic luminescent material with high luminous efficiency and narrow luminous spectrum can be obtained. The special conjugated structure of the organic compound provided by the embodiment of the application has the advantages of larger power supply property and more obvious effect of regulating light color.
In an embodiment of the present application, the formation of the bond between the second structural unit and the first structural unit by at least replacing a part of the ring structure in the first structural unit specifically includes:
The second structural unit forms a bond by substituting the A ring, the B ring or the C ring in the first structural unit; or the second structural unit forms a bond by substituting the A ring-Y in the first structural unit; or the second structural unit forms a bond by substituting the B ring-Z in the first structural unit; or the second structural unit forms a bond by substituting the A ring-Y-C ring in the first structural unit; or the second building block forms a bond by replacing the B ring-Z-C ring in the first building block. Various bonding modes can obtain rich and various organic compounds with different structures, thereby meeting the application scenes of luminescent materials with more different requirements.
In an embodiment of the present application, the polycyclic structure includes any one of the structures represented by the formulas (III-1) to (III-5), or includes a polymer formed by compounding any one or more of the structures represented by the formulas (III-1) to (III-5):
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring. The polycyclic structure can enable the organic compound to have higher luminous efficiency and narrower half-width.
In an embodiment of the present application, when the polycyclic structure includes a polymer formed by compounding any one or more structures represented by the formulas (III-1) to (III-5), any one or more structures represented by the formulas (III-1) to (III-5) form a bond by sharing a part of the ring structures in the formulas (III-1) to (III-5). By sharing the ring structure, an organic compound having a stable and simple structure can be obtained, and the preparation can be made easier.
In an embodiment of the present application, the polymer formed by compounding any one or more structures represented by the formulas (III-1) to (III-5) includes any one of the formulas (IV-1) to (IV-21):
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is independently C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring. The polycyclic structure enables the organic compound to obtain higher luminous efficiency and narrower half-width.
In an embodiment of the application, the substituted or unsubstituted aromatic ring is a substituted or unsubstituted C 6-C30 aromatic ring; the substituted or unsubstituted aromatic heterocycle is a substituted or unsubstituted C 3-C30 aromatic heterocycle;
the hetero atom in the aromatic heterocycle is one or more selected from oxygen atom, sulfur atom, nitrogen atom and selenium atom. The aromatic ring or aromatic heterocyclic structure suitable for the number of carbon atoms can lead the integral structure of the organic compound to be simpler and the preparation to be easier.
In an embodiment of the present application, the substituted or unsubstituted aromatic ring includes one of 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 duplex benzene ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted binaphthyl ring, a substituted or unsubstituted fluorene ring, and a substituted or unsubstituted spirofluorene ring; the substituted or unsubstituted aromatic heterocyclic ring includes one of a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted benzopyrrole 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 triazine ring, and a substituted or unsubstituted xanthone ring. The aromatic ring structure can enable the organic compound to obtain good conjugation effect, and improve the luminous performance of the organic compound.
In an embodiment of the present application, the substituent in the substituted aromatic ring, the substituted aromatic heterocycle includes one or more of deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic acid group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamino group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted acyl group, substituted or unsubstituted borane group, substituted or unsubstituted silane group, and substituted or unsubstituted aromatic silicon group. The introduction of various substituents can further realize the adjustment of the luminescence properties of the organic compound.
In an embodiment of the application, the substituted or unsubstituted alkyl is a substituted or unsubstituted C 1-C30 alkyl; the substituted or unsubstituted cycloalkyl is a substituted or unsubstituted C 3-C30 cycloalkyl; the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C 2-C30 heterocycloalkyl; the substituted or unsubstituted alkoxy is a substituted or unsubstituted C 1-C30 alkoxy; the substituted or unsubstituted aryl is a substituted or unsubstituted C 6-C30 aryl; the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C 3-C30 heteroaryl; the substituted or unsubstituted aryloxy is a substituted or unsubstituted C 6-C30 aryloxy; the substituted or unsubstituted heteroaryloxy is a substituted or unsubstituted C 3-C30 heteroaryloxy; the substituted or unsubstituted alkylamino is a substituted or unsubstituted C 1-C30 alkylamino; the substituted or unsubstituted arylamine group is a substituted or unsubstituted C 6-C30 arylamine group; the substituted or unsubstituted heteroarylamino group is a substituted or unsubstituted C 3-C30 heteroarylamino group; the substituted or unsubstituted acyl is a substituted or unsubstituted C 1-C30 acyl; the substituted or unsubstituted aryl silicon group is a substituted or unsubstituted C 6-C30 aryl silicon group. The group suitable for the number of carbon atoms can lead the whole organic compound to have a simpler structure and is easier to realize preparation.
In an embodiment of the present application, at least one of the W, L 1、L2 groups is a nitrogen-containing group. The nitrogen-containing group can improve the conjugation effect of the whole organic compound and improve the luminous performance.
The embodiment of the application also provides a preparation method of the organic compound, which comprises the following steps:
Reacting an intermediate formed by bonding a third structural unit shown in a formula (IA) and a second structural unit shown in a formula (II) with a precursor capable of providing X to introduce X into the intermediate and realize ring closure to obtain an organic compound; the organic compound comprises a polycyclic structure formed by bonding at least one first structural unit shown in a formula (I) and at least one second structural unit shown in a formula (II), wherein the second structural unit is bonded with the first structural unit by at least replacing part of a ring structure in the first structural unit;
Wherein the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring are independently selected from substituted or unsubstituted aromatic rings or substituted or unsubstituted aromatic heterocyclic rings, and the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring can be mutually connected to form a ring in the organic compound; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring. The preparation method does not need to introduce dangerous chemical reagents, has simple preparation process and is easy to realize industrial production.
A second aspect of embodiments of the present application provides the use of the organic compounds and salts thereof according to the first aspect in electroluminescent devices, organic light emitting field effect transistors, organic photovoltaic devices, light emitting electrochemical cells, photoelectric converters, light opening devices, image sensors, lasers, photosensitive devices, biological imaging devices, paints, organic laser devices. The organic compound provided by the embodiment of the application has good luminescence property, and can be used as a luminescent material in various scenes, so that the properties of various devices, equipment and materials can be improved.
A third aspect of the embodiments of the present application provides a light-emitting layer comprising the organic compound according to the first aspect of the embodiments of the present application. The organic compound provided by the embodiment of the application has good luminescence property, and can improve the luminescence property of the luminescence layer.
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 organic compound, that is, the organic compound according to the embodiment of the present application forms the light emitting layer together with the host material as a guest material. The organic compound provided by the embodiment of the application can be used as a doping material to sensitize a main body material emitting visible light better, so that the luminous performance of the luminous layer is improved.
A fourth aspect of the embodiments of the present application provides an electronic device comprising the organic compound according to the first aspect of the embodiments of the present application; or comprises a light emitting layer according to the third aspect of the embodiments of the present application. The organic compound provided by the embodiment of the application has good luminescence property, and can improve the device performance.
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 organic compound. Specifically, the functional layer may include the light emitting layer.
In an embodiment of the present application, the electronic device may be a device comprising an electroluminescent device, an organic light emitting field effect transistor, an organic photovoltaic device or a light emitting electrochemical cell.
A fifth aspect of the embodiment of the present application provides a display device, where the display device includes an electronic device according to the fourth aspect of the embodiment of the present application; or comprises a light emitting layer according to the third aspect of the embodiments of the present application. The organic compound provided by the embodiment of the application has good luminescence property, and is beneficial to improving the display effect of the display device.
The embodiment of the application also provides electronic equipment, which comprises the display device of the fifth aspect of the embodiment of the application; or an electronic device according to the fourth aspect of the embodiments of the present application. The organic 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 comprises the electronic device according to the fourth aspect of the embodiment of the application; or comprises a light emitting layer according to the third aspect of the embodiments of the present application. The organic 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 fluorescence spectrum of the organic compound produced in example 1 of the present application;
FIG. 5 is a fluorescence spectrum of the organic compound produced in example 2 of the present application;
FIG. 6 is a fluorescence spectrum of the organic compound produced in example 3 of the present application;
FIG. 7 is a fluorescence spectrum of the organic compound produced in example 4 of the present application;
FIG. 8 is a fluorescence spectrum of the organic compound produced in example 5 of the present application;
FIG. 9 is a fluorescence spectrum of the organic compound produced in example 6 of the present application;
FIG. 10 is a fluorescence spectrum of the organic compound produced in example 7 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. In order to better meet better color development standards, it is of great importance to develop organic luminescent materials with good luminescent properties. Therefore, the embodiment of the application provides an organic compound which has narrow half-peak width and higher fluorescence quantum efficiency, can be used as a light-emitting layer 301 doping material of an organic electroluminescent device, and improves the light-emitting performance of the light-emitting device.
The organic compound comprising a polycyclic structure in which at least one first structural unit represented by the formula (I) and at least one second structural unit represented by the formula (II) are bonded to each other by substituting at least a part of the cyclic structure in the first structural unit will be specifically described below;
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted aromatic heterocyclic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
The organic compound provided by the embodiment of the application comprises a brand new molecular skeleton formed by bonding a first structural unit shown in a formula (I) and a second structural unit shown in a formula (II), wherein the molecular skeleton is characterized in that the second structural unit shown in the formula (II) is introduced on the basis of the first structural unit shown in the formula (I), a seven-ring, eight-ring or nine-ring structure is constructed between three ring structures by the second structural unit shown in the formula (II), the second structural unit shown in the formula (II) has larger steric hindrance and higher rigidity, the number of freely rotating phenyl groups in the molecular skeleton can be reduced, the rigidity of the molecular skeleton is improved, the intermolecular aggregation of the compound in a solid state is restrained, and the conjugation length of the molecular skeleton can be limited, so that the molecular skeleton can simultaneously realize the molecular structure characteristics of large steric hindrance, high rigidity and low conjugation, and finally, a novel organic luminescent material with high luminous efficiency and narrow luminous spectrum can be obtained. The special conjugated structure of the organic compound provided by the embodiment of the application has the advantages of larger power supply property and more obvious effect of regulating light color.
In an embodiment of the present application, the organic compound is formed by bonding at least one first structural unit represented by formula (I) and at least one second structural unit represented by formula (II) to form a polycyclic structure as a molecular skeleton, and the bonding means a bonding manner in which atoms are connected to each other by chemical bonds. The polycyclic structure may specifically be formed by bonding a first structural unit represented by the formula (I) with a second structural unit represented by the formula (II); it may be formed by bonding one first structural unit represented by the formula (I) to a plurality of (two or more) second structural units represented by the formula (II). The bonding manner of the first structural unit and the second structural unit may specifically be that the second structural unit forms a bond with the first structural unit by at least replacing a part of the ring structure in the first structural unit. When the polycyclic structure includes a plurality of second structural units represented by the formula (II), the plurality of second structural units may be substituted for part of the structure in the first structural unit, respectively, and bonding may be formed between the plurality of second structural units by sharing part of the cyclic structure; the plurality of second structural units may have the same structure or may have different structures. Wherein a portion of the ring structure may be one or more ring structures.
In an embodiment of the present application, the formation of the bond between the second structural unit and the first structural unit by at least replacing a part of the ring structure in the first structural unit may specifically include:
The second structural unit forms a bond by substituting the A ring, the B ring or the C ring in the first structural unit; or a second structural unit forms a bond by substituting the A ring-Y in the first structural unit; or the second structural unit forms a bond by substituting the B ring-Z in the first structural unit; or the second structural unit forms a bond by substituting the A ring-Y-C ring in the first structural unit; or the second building block forms a bond by replacing the B ring-Z-C ring in the first building block. When the polycyclic structure includes a plurality of second structural units represented by the formula (II), the plurality of second structural units may be independently bonded to the first structural unit in any of the above bonding manners, and the plurality of second structural units may be bonded to each other by sharing a partial ring structure.
In some embodiments of the application, the polycyclic structure comprises any one of the structures of formulas (III-1) to (III-5), or comprises a polymer composited by any one or more of the structures of formulas (III-1) to (III-5):
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
The above formula (III-1) and formula (III-2) are formed by bonding a second structural unit shown in formula (II) by replacing the ring A in the first structural unit shown in formula (I); the above formula (III-3) and formula (III-4) are formed by bonding a second structural unit represented by formula (II) by substituting the A ring-Y-C ring in the first structural unit represented by formula (I).
In an embodiment of the present application, when the polycyclic structure includes a polymer formed by compounding any one or more structures represented by the formulas (III-1) to (III-5), any one or more structures represented by the formulas (III-1) to (III-5) form a bond by sharing a part of the ring structures in the formulas (III-1) to (III-5).
In some embodiments of the application, the polycyclic structure may be a polymer comprising a complex of any one or more structures represented by formulas (III-1) to (III-5). Wherein the polycyclic structure includes a polymer formed by compounding any one of structures represented by formulas (III-1) to (III-5), specifically, a polymer formed by compounding a plurality of structures represented by formula (III-1), a plurality of structures represented by formula (III-2), a plurality of structures represented by formula (III-3), a plurality of structures represented by formula (III-4), or a plurality of structures represented by formula (III-5). For example, in some embodiments, the polycyclic structure comprises a polymer composited from two structures of formula (III-4); in some embodiments, the polycyclic structure comprises a polymer formed by compounding two structures of formula (III-5). The polycyclic structure may be a polymer comprising a combination of any of a plurality of structures represented by the formulae (III-1) to (III-5), and specifically means a polymer comprising a combination of any two or more of at least one structure represented by the formula (III-1), at least one structure represented by the formula (III-2), at least one structure represented by the formula (III-3), at least one structure represented by the formula (III-4), and at least one structure represented by the formula (III-5). In some embodiments, the polycyclic structure may be specifically represented by, for example, formula (IV-1) through formula (IV-21).
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is independently C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
When the number of the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring is plural, the plural rings may have the same structure or may have different structures. For example, in formula (IV-1), the two E rings may have the same or different structures, the two F rings may have the same or different structures, and the two G rings may have the same or different structures.
In an embodiment of the present application, at least one of W, L 1、L2 is a nitrogen-containing group, specifically, W is N, and L 1、L2 is a single bond; or W is N, one of L 1、L2 is a single bond, and the other is N-R 3; it is also possible that W is N and L 1、L2 are both N-R 3.
In the embodiment of the application, the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring, and can be specifically connected to form a ring through a single bond or a substituent group.
In an embodiment of the application, the substituted or unsubstituted aromatic ring is a substituted or unsubstituted C 6-C30 aromatic ring; the substituted or unsubstituted aromatic heterocycle is a substituted or unsubstituted C 3-C30 aromatic heterocycle; the aromatic ring may be a monocyclic aryl or a polycyclic aryl; the aromatic heterocycle may be a monocyclic heteroaryl or a polycyclic heteroaryl. Polycyclic aryl groups may be fused or non-fused (e.g., biphenyls). In some embodiments, the substituted or unsubstituted aromatic ring may be a substituted or unsubstituted C 6-C20 aromatic ring, a substituted or unsubstituted C 6-C12 aromatic ring. In some embodiments, the substituted or unsubstituted aromatic heterocycle may be a substituted or unsubstituted C 3-C20 aromatic heterocycle, a substituted or unsubstituted C 3-C12 aromatic heterocycle.
The hetero atom in the aromatic heterocycle is one or more selected from oxygen atom, sulfur atom, nitrogen atom and selenium atom.
In an embodiment of the present application, the substituted or unsubstituted aromatic ring includes one of 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 pyrene ring, a substituted or unsubstituted spirofluorene ring, and a substituted or unsubstituted binaphthyl fluorene ring; the substituted or unsubstituted aromatic heterocyclic ring includes one of a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted benzopyrrole 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 triazine ring, and a substituted or unsubstituted xanthone ring. For example, the substituted benzene ring may be deuterated phenyl, tritiated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, and the like. The substituted biphenyl ring may be deuterated biphenyl, tritiated biphenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, and the like.
In an embodiment of the application, the substituents in the substituted aromatic ring, substituted aromatic heterocycle include one or more of deuterium atom, tritium atom, halogen atom, cyano group, nitro group, carboxyl group, sulfonic acid group, isocyano group, thiocyanate group, isothiocyanate group, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamino group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted acyl group, substituted or unsubstituted borane group, substituted or unsubstituted silane group, and substituted or unsubstituted aromatic silicon group.
In some embodiments of the present application, the A ring, B ring, C ring, D ring, E ring, F ring, G ring may be, for example, a ring selected from the group consisting of 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 naphthalene ring, an anthracene ring, a deuterated anthracene ring, an alkyl-substituted anthracene ring, a tritiated alkyl-substituted anthracene ring, a phenanthrene ring, a deuterated phenanthrene ring, an alkyl-substituted phenanthrene ring, a tritiated phenanthrene ring deuterated alkyl-substituted phenanthrene ring, tritiated alkyl-substituted phenanthrene ring, biphenyl ring, deuterated biphenyl ring, tritiated biphenyl ring, methyl-substituted biphenyl ring, ethyl-substituted biphenyl ring, isopropyl-substituted biphenyl ring, tert-butyl-substituted biphenyl ring, deuterated methyl-substituted biphenyl ring, deuterated ethyl-substituted biphenyl ring, deuterated isopropyl-substituted biphenyl ring, deuterated tert-butyl-substituted biphenyl ring, terphenyl ring, deuterated terphenyl ring, tritiated terphenyl ring, pyridine ring, phenyl-substituted pyridine ring, quinoline ring, furan ring, methyl-substituted furan ring, phenyl-substituted furan ring, thiophene ring, methyl-substituted thiophene ring, phenyl-substituted pyrrole ring, benzothiophene ring, benzofuran ring, methyl-substituted benzofuran ring, any one of carbazole rings.
In the embodiment of the application, the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G may have the same structure partially or completely or may have different structures.
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-C30 alkyl group. In some embodiments, the substituted or unsubstituted alkyl group may be a substituted or unsubstituted C 1-C20 chain alkyl group, a substituted or unsubstituted C 1-C10 chain alkyl group, a substituted or unsubstituted C 1-C6 chain alkyl group, and specifically may be, for example, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted tert-butyl group, or the like. 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, and the like.
In embodiments of the present application, the substituted or unsubstituted cycloalkyl groups referred to above may be substituted or unsubstituted C 3-C30 cycloalkyl groups. In some embodiments, the substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C 3-C20 cycloalkyl group, a substituted or unsubstituted C 4-C12 cycloalkyl group, a substituted or unsubstituted C 5-C6 cycloalkyl group, specifically may be, for example, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, or the like. 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-C30 heterocycloalkyl group. In some embodiments, the substituted or unsubstituted heterocycloalkyl may be a substituted or unsubstituted C 3-C20 heterocycloalkyl, a substituted or unsubstituted C 4-C12 heterocycloalkyl, a substituted or unsubstituted C 5-C6 heterocycloalkyl. 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 alkoxy group may be a substituted or unsubstituted C 1-C30 alkoxy group, may be a linear alkoxy group, or may be a branched alkoxy group; in some embodiments, the substituted or unsubstituted alkoxy group may be a substituted or unsubstituted C 1-20 alkoxy group, a C 1-C10 alkoxy group, a C 1-C6 alkoxy group. As an example, the substituted or unsubstituted alkoxy group may be a substituted or unsubstituted methoxy group (-OCH 3), a substituted or unsubstituted ethoxy group (-OCH 2CH3), a substituted or unsubstituted propoxy group, a substituted or unsubstituted t-butoxy group, or the like.
In embodiments of the present application, the substituted or unsubstituted aryl groups referred to above may be substituted or unsubstituted C 6-C30 aryl groups; the substituted or unsubstituted aryl may be a substituted or unsubstituted C 6-C30 aryl, and the aryl may be a monocyclic aryl or a polycyclic aryl. In some embodiments, the substituted or unsubstituted aryl may be a substituted or unsubstituted C 6-C20 aryl, a substituted or unsubstituted C 6-C12 aryl. Wherein 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). Specifically, the substituted or unsubstituted polycyclic aryl group of biphenyls may be, but is not limited to, a substituted or unsubstituted biphenyl group, a terphenyl group, a diphenyl ether 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-C30 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-C20 aryloxy group, a substituted or unsubstituted C 6-C12 aryloxy group. Specifically, the aryloxy group may be an aryloxy group obtained by oxidation of the above aryl group, for example, a phenoxy group obtained by oxidation of a phenyl group, and the like, and will not be described in detail herein.
In embodiments of the present application, the substituted or unsubstituted heteroaryl groups referred to above may be substituted or unsubstituted C 3-C30 heteroaryl groups. In some embodiments, the substituted or unsubstituted heteroaryl may be a substituted or unsubstituted C 5-C20 heteroaryl, a substituted or unsubstituted C 6-C12 heteroaryl. 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. Illustratively, the substituted or unsubstituted heteroaryl group may be a pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, benzofuryl, dibenzofuryl, tert-butyl-substituted dibenzofuryl, thienyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, xanthonyl, triazinyl, phenyl-substituted triazinyl, and the like.
In embodiments of the present application, the substituted or unsubstituted heteroaryloxy groups referred to above may be substituted or unsubstituted C 3-C30 heteroaryloxy groups. In some embodiments, the substituted or unsubstituted heteroaryloxy group may be a substituted or unsubstituted C 5-C20 heteroaryloxy group, a substituted or unsubstituted C 6-C12 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-C30 alkylamino group. In some embodiments, the substituted or unsubstituted alkylamino may be a substituted or unsubstituted C 2-C20 alkylamino, a substituted or unsubstituted C 3-C12 alkylamino. 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 arylamine group may be a substituted or unsubstituted C 6-C30 arylamine group. In some embodiments, the substituted or unsubstituted arylamine group may be a substituted or unsubstituted C 6-C20 arylamine group, a substituted or unsubstituted C 7-C15 arylamine group. By way of example, the substituted or unsubstituted arylamino group may be, for example, a phenylamino group, a diphenylamino group, a dimethylphenylamino group, a tert-butylphenyl-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 heteroarylamino group may be a substituted or unsubstituted C 3-C30 heteroarylamino group. In some embodiments, the substituted or unsubstituted heteroarylamino group may be a substituted or unsubstituted C 5-C20 heteroarylamino group, a substituted or unsubstituted C 6-C12 heteroarylamino group.
In an embodiment of the present application, the above-mentioned substituted or unsubstituted acyl group may be a substituted or unsubstituted C 1-C30 acyl group; in some embodiments, the substituted or unsubstituted acyl group may be a substituted or unsubstituted C 1-C20 acyl group, a substituted or unsubstituted C 1-C10 acyl group; examples of the "acyl" include formyl, acetyl, propionyl, butyryl, hexanoyl, carbamoyl and haloformyl.
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, an alkylphenyl-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 present application, the substituted or unsubstituted aryl group is a substituted or unsubstituted C 6-C30 aryl group; in some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted C 6-C20 aryl; specifically, for example, phenyl silicon group and the like are mentioned.
In an embodiment of the present application, a method of manufacturing a semiconductor device, R 1、R2、R3 can be 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 fluoropropyl 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 deuterated 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 dibenzofuranyl, dibenzothiophenyl, tert-butyl substituted dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, tert-butyl substituted carbazolyl, tert-butyl substituted N-carbazolylphenyl, 9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, biphenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert-butyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated ethyl substituted biphenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted biphenyl, deuterated amino substituted biphenyl, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, triazinyl, phenyl-substituted triazinyl, borane, phenyl-substituted borane, methoxy or tert-butoxy.
In an embodiment of the present application, the organic compound may specifically include, but is not limited to, any one of organic compounds represented by structural formulas (1) to (1362):
The organic compound provided by the embodiment of the application can be prepared by adopting various chemically realizable modes.
The embodiment of the application provides a preparation method of an organic compound, which comprises the following steps:
Reacting an intermediate formed by bonding a third structural unit shown in a formula (IA) and a second structural unit shown in a formula (II) with a precursor capable of providing X to introduce X into the intermediate and realize ring closure to obtain an organic compound; the organic compound comprises a polycyclic structure formed by bonding at least one first structural unit shown in a formula (I) and at least one second structural unit shown in a formula (II), wherein the second structural unit is bonded with the first structural unit by at least replacing part of a ring structure in the first structural unit;
Wherein the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring are independently selected from substituted or unsubstituted aromatic rings or substituted or unsubstituted aromatic heterocyclic rings, and the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring can be mutually connected to form a ring in the organic compound; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
In one embodiment of the application, the organic compound can be specifically obtained by constructing a polycyclic aromatic amine skeleton intermediate through carbon-nitrogen coupling and then carrying out boronation and ring closure by utilizing boron tribromide. The synthesis process of the organic compound does not need to use dangerous reagents such as butyl lithium and the like, reduces the synthesis difficulty of the organic luminescent material, and is easy for large-scale production.
The organic compound provided by the embodiment of the application has higher fluorescence quantum yield and narrower half-peak width, can be used in various electronic devices with functions of luminescence, display, illumination and the like, and improves the performance of device efficiency and the like. The organic 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.
The embodiment of the application provides application of the organic compound and the salt 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, photosensitive devices, biological imaging equipment, paints and organic laser equipment. Specifically, the above-mentioned organic compound can be used as a light-emitting material in the above-mentioned device. For example, the organic 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 of the device and the like. Specifically, the organic compound provided by the embodiment of the application has narrow half-peak width and high fluorescence quantum yield, can be used as a light-emitting layer doping material of an organic electroluminescent device, and improves the device efficiency.
The embodiment of the application provides an electronic device, which comprises the organic compound. 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 contains the above-described organic 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 of the organic compounds described above in the present application. The organic compound is used as a doping material of the light-emitting layer 301, and can play a role of sensitizing excitons, so that the light-emitting efficiency of the device is improved; the half-peak width of the organic compound is narrower, 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.
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 organic compounds of the present application; it is also possible to include one or more of the above-described organic compounds of the application together with 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, and the energy transfer efficiency between the host material and the organic compound serving as the doping material is high, so that the light-emitting potential of the organic 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 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 vehicle-mounted display device, 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 in-car control screen, etc.
The following examples are provided to further illustrate embodiments of the application.
Example 1
Synthesis of organic Compound 1
1) Preparation of intermediate Compound 1-1
2-Iodobiphenyl (50 mmol), 2-bromoaniline (1.5 eq. Equivalent), cesium carbonate (Cs 2CO3, 2.0 eq.) palladium acetate (Pd (OAc) 2, 5 mol%), triphenylphosphine (PPh, 10 mol%) were added to a 200mL three-necked flask, 100mL of ultra-dry DMF (N, N-dimethylformamide) was added to the system at room temperature under nitrogen atmosphere, sealed, and vigorously stirred at 120 ℃ for 36 hours. After cooling to room temperature, the mixture was filtered with celite, washed with ethyl acetate, extracted with ethyl acetate and water, and the organic phase was dried under reduced pressure. Recrystallization from ethyl acetate and petroleum ether gave the intermediate compound 1-1 target molecule (8.47 g, 70%). The reaction process is shown in the following formula:
2) Preparation of intermediate Compounds 1-2
2, 6-Di-t-butylcarbazole (t-BuCz, 11mmol,1.1 eq.) was added to a 100mL three-necked flask, and 30mL of ultra-dry DMF was added to the system at room temperature under nitrogen atmosphere to dissolve all; subsequently, naH (12 mmol,1.2eq.60% dispersed in liquid paraffin) was added to the system in portions in an ice-water bath and nitrogen atmosphere, and after almost no solid was present in the system, an ultra-dry DMF solution (10mmol,1eq.20mL DMF) of 3-fluoro-2, 3-dibromobenzene was slowly added dropwise to the system through a constant pressure dropping funnel at room temperature in nitrogen atmosphere, and stirred for 1 hour; thereafter, the mixture was stirred at 120℃for 12 hours in a nitrogen atmosphere. After cooling to room temperature, slowly adding water to quench reaction, extracting with ethyl acetate for three times, collecting organic phase, and spin drying under reduced pressure. By PE: ea=20: 1 to give the corresponding intermediate compound 1-2 target molecule (4.34 g, 85%). The reaction process is shown in the following formula:
3) Preparation of intermediate Compounds 1-3
Intermediate compounds 1-2 (8 mmol), intermediate compounds 1-1 (1.5 eq.) sodium tert-butoxide (t-BuONa, 1.5 eq.) palladium acetate (5 mol%), S-Phos (2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, 10 mol%) were added to a 100mL three-necked flask, and 30mL of ultra-dry toluene (Toluene) was added to the system at room temperature under nitrogen atmosphere followed by stirring under reflux at 120 ℃ for 24 hours. After cooling to room temperature, the mixture was filtered with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: ea=20: 1 to give the corresponding intermediate compound 1-3 target molecule (4.85 g, 90%). The reaction process is shown in the following formula:
4) Preparation of organic Compound 1
The intermediate compounds 1-3 (4 mmol) obtained were added to a 100mL dry three-necked flask, and 30mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by cooling to-78 ℃. 2.5M n-butyllithium solution (n-BuLi, 4.4mmol,1.76 mL) was slowly added dropwise via a constant pressure dropping funnel, and the mixture was stirred under nitrogen for 1 hour. Subsequently, the temperature was raised to-40℃and boron tribromide (BBr 3, 6.6mmol,0.625 mL) was slowly added dropwise, which was then allowed to stir at room temperature for 1 hour. Super-dry N, N-diisopropylethylamine (i-Pr 2NEt2, 16mmol,2.8 mL) was then slowly added dropwise at 0deg.C, and after the addition was completed it was moved to 120deg.C for reaction for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: dcm=40: 1, and recrystallised from ethyl acetate and petroleum ether to give the corresponding organic compound 1 target molecule (1.11 g, 46%). Product characterization: MS (ESI) 605.
The reaction process is shown in the following formula:
Example 2
Synthesis of organic Compound 2
1) Preparation of intermediate Compound 2-1
1,2, 3-Tribromobenzene (20 mmol), diphenylamine (1.1 eq.), sodium t-butoxide (1.5 eq.), palladium acetate (5 mol%), xant-Phos (10 mol%) were added to a 150mL three-necked flask, 80mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by stirring under reflux at 120℃for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: ea=50: 1 to give the corresponding intermediate compound 2-1 target molecule (6.41 g, 80%). The reaction process is shown in the following formula:
2) Preparation of intermediate Compound 2-2
The intermediate compound 2-1 (10 mmol) obtained was added, the intermediate compound 1-1 (1.5 eq.) obtained in example 1, sodium tert-butoxide (1.5 eq.) and palladium acetate (5 mol%), xant-Phos (4, 5-bis-diphenylphosphine-9, 9-dimethylxanthene, 10 mol%) were added to a 150mL three-necked flask, 40mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by stirring under reflux at 120 ℃ for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: ea=20: 1 to give the corresponding intermediate compound 2-2 target molecule (4.79 g, 85%). The reaction process is shown in the following formula:
3) Preparation of organic Compound 2
The intermediate compound 2-2 (4 mmol) thus prepared was added to a 100mL dry three-necked flask, and 30mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by cooling to-78 ℃. 2.5M n-butyllithium solution (4.4 mmol,1.76 mL) was slowly added dropwise via a constant pressure dropping funnel and stirred under nitrogen for 1 hour. Subsequently, the temperature was raised to-40℃and boron tribromide (6.6 mmol,0.625 mL) was slowly added dropwise, and after the addition was completed, it was allowed to stand at room temperature for stirring for 1 hour. Super-dry N, N-diisopropylethylamine (16 mmol,2.8 mL) was then slowly added dropwise at 0deg.C, and after completion of the addition, it was moved to 120deg.C for reaction for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: dcm=20: 1 and recrystallised from methylene chloride and petroleum ether to give the corresponding target molecule of organic compound 2 (0.593 g, 30%). Product characterization: MS (ESI): 494.
The reaction process is shown in the following formula:
Example 3
Synthesis of organic Compound 3
1) Preparation of intermediate Compound 3-1
1,2, 3-Tribromobenzene (10 mmol), compound 1-1 (3 eq.) prepared in example 1, sodium t-butoxide (3 eq.), palladium acetate (5 mol%), S-Phos (10 mol%) were added to a 100mL three-necked flask, and 30mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by stirring under reflux at 120℃for 24 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: ea=20: 1 to give the corresponding intermediate compound 3-1 target molecule (6.26 g, 62%). The reaction process is shown in the following formula:
2) Preparation of organic Compound 3
The intermediate compound 3-1 (4 mmol) thus prepared was added to a 100mL dry three-necked flask, and 30mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by cooling to-78 ℃. 2.5M n-butyllithium solution (4.4 mmol,1.76 mL) was slowly added dropwise via a constant pressure dropping funnel and stirred under nitrogen for 1 hour. Subsequently, the temperature was raised to-40℃and boron tribromide (6.6 mmol,0.625 mL) was slowly added dropwise, and after the addition was completed, it was allowed to stand at room temperature for stirring for 1 hour. Super-dry N, N-diisopropylethylamine (16 mmol,2.8 mL) was then slowly added dropwise at 0deg.C, and after completion of the addition, it was moved to 120deg.C for reaction for 12 hours. After cooling to room temperature, the solid was collected by suction filtration, washed with deionized water (40 mL), dichloromethane (20 mL) and ethyl acetate (20 mL) to give the corresponding target molecule of organic compound 3 (0.618 g, 25%). Product characterization: MS (ESI): 568.
The reaction process is shown in the following formula:
Example 4
Synthesis of organic Compound 4
1) Preparation of intermediate Compound 4-1
4, 6-Dibromo-1, 3-diphenylamine (40 mmol), 2-iodobiphenyl (2.2 eq.), cesium carbonate (3.0 eq.), palladium acetate (5 mol%), triphenylphosphine (10 mol%) were added to a 200mL three-necked flask, 100mL of ultra-dry DMF was added to the system at room temperature under nitrogen atmosphere, sealed, stirred at room temperature for 30min, followed by vigorous stirring at 120℃for 48 hours. After cooling to room temperature, the mixture was filtered with celite, washed with ethyl acetate, extracted with ethyl acetate and water, and the organic phase was dried under reduced pressure. The intermediate compound 4-1 target molecule (8.47 g, 68%) can be obtained by recrystallization from ethyl acetate and petroleum ether. The reaction process is shown in the following formula:
2) Preparation of intermediate Compound 4-2
The intermediate compound 4-1 (10 mmol) thus prepared was added to a 150mL three-necked flask, 80mL of methylene chloride was added to the system at room temperature in an air atmosphere, followed by addition of N-bromosuccinimide (1.1 eq.) in multiple batches at 0 ℃ and vigorous stirring for 1 hour. The reaction was quenched with water, extracted with ethyl acetate and water, the organic phase was taken, and the product was directly put into the next step after spin-drying under reduced pressure without further purification. This compound (10 mmol), 4-tert-butyliodobenzene (2.0 eq.), sodium tert-butoxide (2.0 eq.), palladium acetate (5 mol%), S-Phos (10 mol%) were added to a 100mL three-necked flask, and 30mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by stirring under heating at 120 ℃ under reflux for 24 hours. After cooling to room temperature, the mixture was filtered with celite, washed with ethyl acetate, extracted with ethyl acetate and water, and the organic phase was dried under reduced pressure. By PE: dcm=100: 1, and recrystallizing with ethyl acetate and petroleum ether to obtain intermediate compound 4-2 target molecule (2.85 g, 38%). The reaction process is shown in the following formula:
3) Preparation of organic Compound 4
The intermediate compound 4-2 (3 mmol) thus prepared was added to a 100mL dry three-necked flask, and 30mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by cooling to-78 ℃. 2.5M n-butyllithium solution (3.3 mmol,1.32 mL) was slowly added dropwise via a constant pressure dropping funnel and stirred under nitrogen for 1 hour. Subsequently, the temperature was raised to-40℃and boron tribromide (4.95 mmol,0.469 mL) was slowly added dropwise, and after the addition was completed, it was allowed to warm to room temperature and stirred for 1 hour. Super-dry N, N-diisopropylethylamine (12 mmol,2.1 mL) was then slowly added dropwise at 0deg.C, and after completion of the addition, it was moved to 120deg.C for reaction for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: dcm=100: 1 and recrystallised from methylene chloride and petroleum ether to give the corresponding target molecule of organic compound 4 (0.448 g, 22%). Product characterization: MS (ESI) 681.
The reaction process is shown in the following formula:
Example 5
Synthesis of organic Compound 5
1) Preparation of intermediate Compound 5-1
1,3, 5-Tribromobenzene (20 mmol), 4-dimethyldiphenylamine (1.1 eq.) sodium t-butoxide (1.5 eq.), palladium acetate (5 mol%), xant-Phos (10 mol%) were added to a 100mL three-necked flask, 60mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by stirring at 120℃under heating reflux for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: ea=100: 1 to give the corresponding intermediate compound 5-1 target molecule (7.48 g, 87%). The reaction process is shown in the following formula:
2) Preparation of intermediate Compound 5-2
The prepared compound 5-1 (10 mmol), intermediate compound 1-1 (2.2 eq.), sodium t-butoxide (3 eq.), palladium acetate (5 mol%), tri-t-butylphosphine tetrafluoroborate (10 mol%) were added to a 100mL three-necked flask, 40mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by stirring under heating at 120 ℃ for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: ea=10: 1 to give the corresponding intermediate compound 5-2 target molecule (6.79 g, 90%). The reaction process is shown in the following formula:
3) Preparation of organic Compound 5
The prepared compound 5-2 (2 mmol) was added to a 100mL dry autoclave branch, and 20mL of super-dry o-dichlorobenzene (oDCB), boron tribromide (6 eq.) was added to the system at room temperature under nitrogen atmosphere, followed by vigorous stirring at 180℃for 24 hours. After cooling to room temperature, the system was slowly poured into 50mL of ice water, extracted with ethyl acetate, and the organic phase was taken and dried under reduced pressure. 30mL of methanol was added, and the mixture was suction-filtered after precipitation of a solid. By PE: ea=1: 1 (20 mL), slurried for 20 minutes at 80℃in a 25mL round bottom flask, cooled to room temperature, suction filtered, and treated with PE: ea=1: 1 (20 mL) and finally spin-drying the product under reduced pressure to give the target molecule of organic compound 5 (0.763 g, 50%). Product characterization: MS (ESI) 764. The reaction process is shown in the following formula:
Example 6
Synthesis of organic Compound 6
The intermediate compound 5-2 (1 mmol) prepared in example 5 was added to a 100mL dry autoclave branch, and 15mL of super dry mesitylene, boron tribromide (32 eq.) was added to the system at room temperature under nitrogen atmosphere, followed by vigorous stirring at 180 ℃ for 24 hours. After cooling to room temperature, the system was slowly poured into 50mL of ice water, extracted with ethyl acetate, and the organic phase was taken and dried under reduced pressure. By PE: ea=100: 1 to give the corresponding organic compound 6 target molecule (0.077 g, 10%). Product characterization: MS (ESI): 772.
The reaction process is shown in the following formula:
Example 7
Synthesis of organic Compound 7
1) Preparation of intermediate Compound 7-1
O-nitroaniline (100 g,716 mmol) was dissolved in 100mL acetic acid and warmed to 60 ℃. N-bromosuccinimide (NBS, 130g,736 mmol) was added to 150mL acetic acid (AcOH) to prepare a turbid liquid, and the turbid liquid was slowly added to an acetic acid solution of o-nitroaniline, and the reaction was continued at 65℃for 3.5 hours. After cooling to room temperature, 2L of water was added to the reaction system, the supernatant was decanted after standing, and washing with water was repeated twice again. Proper amount of 1M sodium hydroxide solution is added to adjust the pH to 7. Suction filtration, washing the residue with a proper amount of water three times, and drying the residue to obtain 116.5g of target molecule of intermediate compound 7-1 in 75% yield. The reaction process is shown in the following formula:
2) Preparation of intermediate Compound 7-2
Sodium nitrite (18 g,260 mmol) was slowly added to 100mL concentrated sulfuric acid (conc. H 2SO4) (note: substantial exotherm) at 0deg.C, warmed to 70deg.C and stirred for 15 minutes. After the solution was sufficiently dissolved, the ice bath was cooled to 0 ℃. Simultaneously, intermediate compound 7-1 (45 g,207 mmol) was added to 100mL of acetic acid to prepare a turbid liquid. The cloudy solution was slowly added to the prepared concentrated sulfuric acid solution of sodium nitrite at 0℃and the system was stirred at room temperature for 50 minutes (note: a large exotherm). An aqueous solution (75 mL) of potassium iodide (KI, 45g,271 mmol) was then slowly added at 0deg.C (note: substantial exotherm, substantial gassing). Then the temperature was raised to 50℃and the reaction was carried out for 1 hour. After cooling to room temperature, adding 2L of water into the reaction system, adding a proper amount of sodium thiosulfate to quench the reaction, standing, pouring out the supernatant, and repeatedly adding water for washing twice again. Proper amount of 1M sodium hydroxide solution is added to adjust the pH to 7. Suction filtration, using a proper amount of water to wash the filter residue three times, and drying the filter residue to obtain the intermediate compound 7-2 target molecule 40g, with a yield of 60%. The reaction process is shown in the following formula:
3) Preparation of intermediate Compound 7-3
Tin dichloride (SnCl 2, 200g,886 mmol) was slowly added to 100mL of concentrated hydrochloric acid at 0deg.C, after which a cloudy solution of intermediate compound 7-2 (60 g,163 mmol) in ethanol (EtOH, 150 mL) was slowly added (note: delay of intense exotherm after a period of time). Stirring was continued for 15 minutes at 0 ℃. Then the temperature was raised to 60℃and the reaction was carried out for 45 minutes. After cooling to room temperature, adding 2L of water into the reaction system, adding a proper amount of sodium thiosulfate to quench the reaction, standing, pouring out the supernatant, and repeatedly adding water for washing twice again. Adding a proper amount of 1M sodium hydroxide solution to adjust the pH to 7, carrying out suction filtration, and washing the filter residue with a proper amount of water for three times. After drying the filter residue, the filter residue is dissolved with dichloromethane and a suitable amount of silica gel is added. Purification by flash chromatography on silica gel with dichloromethane as eluent afforded the corresponding intermediate compound 7-3 target molecule (26.7 g, 55%). The reaction process is shown in the following formula:
4) Preparation of intermediate Compounds 7-4
The intermediate compound 7-3 (29.8 g,100 mmol) prepared, the anthranilic acid pinacol ester (1 eq.), potassium carbonate (K 2CO3, 3 eq.) and tetrakis (triphenylphosphine) palladium (Pd (PPh 3)4, 2.5 mol%) were added to a 500mL three-port flask, 100mL of ethylene glycol dimethyl ether (DME) and 100mL of water were added to the system at room temperature under nitrogen atmosphere, followed by stirring for 12 hours under heating reflux at 120 ℃ c.
5) Preparation of intermediate Compounds 7-5
The intermediate compound 7-4 (26.3 g,100 mmol) prepared, tris (dibenzylideneande-acetone) dipalladium (Pd 2(dba)3, 2 mol%), bis (2-diphenylphosphinophenyl) ether (DPE-phos, 4 mol%), sodium tert-butoxide (NaO t Bu,3 eq.) was added to a 500mL three-necked flask, 200mL of ultra-dry toluene (PhMe) was added to the system at room temperature under nitrogen atmosphere, and iodobenzene (2 eq.) was added, and the system was stirred at room temperature for 15 minutes, followed by heating at 90 ℃ for 10 hours. After cooling to room temperature, filtering, adding a proper amount of silica gel, and drying under reduced pressure. The eluent is PE: ea=50: 1 to give the corresponding intermediate compound 7-5 target molecule (29 g, 70%). The reaction process is shown in the following formula:
6) Preparation of intermediate Compounds 7-6
The intermediate compound 7-5 (41.5 g,100 mmol), tris (dibenzylideneandene acetone) dipalladium (2 mol%), tris-tert-butylphosphine tetrafluoroborate (tBu3PHBF4, 8 mol%), sodium t-butoxide (3 eq.) was added to a 500mL three-necked flask, 200mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, and o-diiodobenzene (1 eq.) was added, and the system was stirred at room temperature for 15 minutes, followed by heating at 90 ℃ for 10 hours. After cooling to room temperature, filtering, adding a proper amount of silica gel, and drying under reduced pressure. The eluent is PE: ea=120: 1 to give the corresponding intermediate compound 7-6 target molecule (17 g, 35%). The reaction process is shown in the following formula:
7) Preparation of intermediate Compounds 7-7
The intermediate compound 7-6 (14.7 g,30 mmol), tris (dibenzylideneandene acetone) dipalladium (2 mol%), 4, 5-bis-diphenylphosphine-9, 9-dimethylxanthene (Xant-Phos, 4 mol%), sodium t-butoxide (3 eq.) were prepared in a 500mL three-necked flask, 200mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, and p-t-butylaniline (1 eq.) was added, and the system was stirred at room temperature for 15 minutes, followed by heating at 110 ℃ for 9 hours. After cooling to room temperature, filtering, adding a proper amount of silica gel, and drying under reduced pressure. The eluent is PE: dcm=5: 1 to give the corresponding intermediate compound 7-7 target molecule (15 g, 90%). The reaction process is shown in the following formula:
8) Preparation of intermediate Compounds 7-8
1,2, 3-Tribromobenzene (31.3 g,100 mmol), bis (4-t-butylphenyl) amine (1 eq.), tris (dibenzylideneacetone) dipalladium (1 mol%), bis (2-diphenylphosphinophenyl) ether (DPE-phos, 2 mol%), sodium t-butoxide (1.5 eq.) were added to a 500mL three-necked flask, 200mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, and the system was stirred at room temperature for 15 minutes followed by heating at 110℃for 10 hours. After cooling to room temperature, filtering, adding a proper amount of silica gel, and drying under reduced pressure. The eluent is PE: dcm=30: 1 to give the corresponding intermediate compound 7-8 target molecule (20 g, 40%). The reaction process is shown in the following formula:
9) Preparation of intermediate Compounds 7-9
The prepared intermediate compound 7-7 (5.58 g,10 mmol), intermediate compound 7-8 (1 eq.) dipalladium tris (dibenzylideneacetone) (2 mol%), tri-t-butylphosphine tetrafluoroborate (8 mol%), sodium t-butoxide (2 eq.) were added to a 250mL three-necked flask, 100mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, and the system was stirred at room temperature for 15 minutes, followed by stirring at 110 ℃ for 16 hours. After cooling to room temperature, filtering, adding a proper amount of silica gel, and drying under reduced pressure. The eluent is PE: dcm=10: 1 to give the corresponding intermediate compound 7-9 target molecule (8.1 g, 82%). The reaction process is shown in the following formula:
10 Preparation of organic Compound 7
The intermediate compound 7-9 (2.97 g,3 mmol) was added to a 50mL dry three-necked flask, and 20mL of ultra-dry toluene was added to the system at room temperature under nitrogen atmosphere, followed by cooling to-78 ℃. 2.4M n-hexane solution of n-butyllithium (4.5 mmol,1.9 mL) was slowly added dropwise via a constant pressure dropping funnel, and the mixture was stirred at room temperature under nitrogen atmosphere for 1 hour. Subsequently, the temperature was lowered to-40℃and boron tribromide (7.5 mmol,0.72 mL) was slowly added dropwise, and after the addition was completed, it was allowed to warm to room temperature and stirred for 1 hour. Super-dry N, N-diisopropylethylamine (DIPEA, 15mmol,2,6 mL) was then slowly added dropwise at 0deg.C, and after completion of the addition, it was moved to 120deg.C for reaction for 12 hours. After cooling to room temperature, the mixture was filtered off with celite, washed with ethyl acetate to remove inorganic salts, then extracted with ethyl acetate and water, and the organic phase was taken and dried under reduced pressure. By PE: dcm=30: 1 and recrystallised from petroleum ether to give the corresponding organic compound 7 target molecule (0.552 g, 20%). Product characterization: MS (ESI): 921.
The reaction process is shown in the following formula:
the organic compounds prepared in the above examples 1 to 7 of the present application, and the existing organic light emitting materials of comparative examples 1 to 3 were subjected to physical and chemical property tests, wherein the chemical structural formulas of the existing organic light emitting materials of comparative examples 1, 2 and 3 are as follows.
The fluorescence spectra of the organic compounds of examples 1 to 7 are shown in fig. 4 to 10, fig. 4 is the fluorescence spectrum of the organic compound of example 1, fig. 5 is the fluorescence spectrum of the organic compound of example 2, fig. 6 is the fluorescence spectrum of the organic compound of example 3, fig. 7 is the fluorescence spectrum of the organic compound of example 4, fig. 8 is the fluorescence spectrum of the organic compound of example 5, fig. 9 is the fluorescence spectrum of the organic compound of example 6, and fig. 10 is the fluorescence spectrum of the organic compound of example 7.
The test results of the fluorescence emission peaks, half-widths, and fluorescence quantum yields (PLQY) of the organic compounds of examples 1 to 7 and comparative examples 1 to 3 are shown in Table 1:
TABLE 1
| Examples | Fluorescence emission peak/nm | Half width/nm | PLQY/％ |
| Example 1 | 489 | 36 | 92 |
| Example 2 | 474 | 35 | 90 |
| Example 3 | 490 | 42 | 94 |
| Example 4 | 481 | 38 | 92 |
| Example 5 | 463 | 32 | 89 |
| Example 6 | 474 | 23 | 88 |
| Example 7 | 460 | 20 | 85 |
| Comparative example 1 | 453 | 26 | 85 |
| Comparative example 2 | 478 | 28 | 80 |
| Comparative example 3 | 465 | 30 | 83 |
Wherein, the emission peak value, the full width at half maximum (FWHM) and the fluorescence quantum yield are obtained by testing a fluorescence spectrometer in a film state.
As can be seen from the results of Table 1, the organic compounds prepared in examples 1 to 7 of the present application have emission peaks in the blue spectral range, have a narrower half-width and a higher fluorescence quantum yield, and can be used as a light-emitting material in organic electroluminescent devices for improving the performance of the light-emitting devices, as compared with the performance of the existing mature light-emitting materials in comparative examples 1 to 3.
The effect of the above-synthesized organic compound of the present application applied to an organic electroluminescent device will be described in detail below with reference to device examples 1 to 2 and device comparative example 1.
Device example 1
An organic electroluminescent device, as shown in fig. 1, comprises a substrate 40 (specifically transparent glass), and an ITO anode 10 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)), a hole injection layer 3021 (PD and HT-1, the ratio of PD to HT-1 being 3:100, the thickness being 10 nm), a hole transport layer 3022 (HT-1, the thickness being 120 nm), an electron blocking layer 3023 (HT-2, the thickness being 10 nm), a light emitting layer 301 (BH as a host material, the organic compound 5 of example 5 being a fluorescent doping material, the mass ratio of BH to the organic compound 5 being 98:2, the thickness being 25 nm), a hole blocking layer 3033 (ET-1, the thickness being 2 nm), an electron transport layer 3032 (ET-2 and LiQ, the mass ratio of ET-2 to LiQ being 1, the thickness being 35 nm), an electron injection layer 3031 (Yb layer, the thickness being 1.5 nm), and a cathode 20 (Mg: the mass ratio of 1:9, the thickness being 17 nm) which are sequentially stacked on the substrate 40.
The preparation process of the OLED light-emitting device comprises the following steps: the ITO anode 10 is washed, i.e., sequentially by a cleaning agent washing, a pure water washing, an isopropyl alcohol ultrasonic washing, and after drying, by an Ar 2 ozone treatment to remove residues on the transparent ITO surface. On the ITO anode 10 after the above washing, PD and HT-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3021 by a vacuum vapor deposition apparatus, and the mass ratio of PD to HT-1 was 3:100. Next, HT-1 was evaporated to a thickness of 120nm as a hole transport layer 3022. HT-2 was then evaporated to a thickness of 10nm as an electron blocking layer 3023. After the electron blocking material was evaporated, a light emitting layer 301 of an OLED light emitting device was formed, and using BH as a host material, the organic compound 5 of example 5 was used as a fluorescent dopant material, and the mass ratio of BH to the organic compound 5 was 98:2, whereby the film thickness of the light emitting layer 301 was 25nm. Vacuum deposition of ET-1 was continued on the light-emitting layer 301 to a film thickness of 2nm, which was a hole blocking layer 3033. And continuously vacuum evaporating ET-2 and LiQ on the hole blocking layer 3033, wherein the mass ratio of the ET-2 to the LiQ is 1:1, the film thickness is 35nm, and the electron transport layer 3032 is formed. On the electron transport layer 3032, an Yb (ytterbium) layer having a film thickness of 1.5nm was formed by a vacuum vapor deposition apparatus, and this layer was the electron injection layer 3031. On the electron injection layer 3031, mg having a film thickness of 17nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is a cathode 20.
Device example 2
Device example 2 differs from device example 1 only in that the light-emitting layer employs the organic compound 7 of example 7 as a fluorescent doping material. The thickness of the hole transport layer was 115nm.
Device comparative example 1
The device comparative example 1 differs from the device example 1 only in that the organic light-emitting material of comparative example 1 was used as the fluorescent doping material for the light-emitting layer.
The molecular structural formula of the related material is shown as follows:
After the OLED light emitting device was fabricated as described above, the anode and cathode were connected using a well-known driving circuit, and the external quantum efficiency, emission peak, operating voltage and current efficiency of the device were measured. The results of testing the external quantum efficiency, the light emission peak value and the lifetime of the obtained device are shown in table 2.
TABLE 2
Note that: the working voltage, the current efficiency, the external quantum efficiency and the luminescence peak value of the device are tested by using an IVL (current-voltage-brightness) testing system; the external quantum efficiency and the luminescence peak value are all tested under 1000cd/m 2; j50 represents the time at which the device brightness decays by 5% at a current density of 50mA/m 2.
As can be seen from the device data results of table 2, the devices of the embodiment of the present application can obtain higher external quantum efficiency, can obtain a light emission peak in the blue region, and have suitable operating voltage and higher current efficiency, and the devices of the device embodiment 2 and the device embodiment 3 can also obtain a higher lifetime than the device of the device comparative example 1.
It should be understood that the first, second, and various numerical numbers referred to herein are merely descriptive convenience and are not intended to limit the scope of the application.
In the present application, "and/or" describing the association relationship of the association object means that there may be three relationships, for example, a and/or B may mean: a alone, a and B together, and B alone, wherein a, B may be singular or plural. The character "/" generally indicates that the context-dependent object is an "or" relationship.
In the present application, "at least one" means one or more, and "a plurality" means two or more. "at least one of" or the like means any combination of these items, including any combination of single item(s) or plural items(s). For example, "at least one (individual) of a, b, or c," or "at least one (individual) of a, b, and c," may each represent: a, b, c, a-b (i.e., a and b), a-c, b-c, or a-b-c, wherein a, b, c may be single or multiple, respectively.
It should be understood that, in various embodiments of the present application, the sequence number of each process described above does not mean that the execution sequence of some or all of the steps may be executed in parallel or executed sequentially, and the execution sequence of each process should be determined by its functions and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present application.
Claims (20)
1. An organic compound, characterized in that the organic compound comprises a polycyclic structure formed by bonding at least one first structural unit represented by formula (I) and at least one second structural unit represented by formula (II), the second structural unit being bonded to the first structural unit by at least replacing part of the cyclic structure in the first structural unit;
Wherein, the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring are independently selected from substituted or unsubstituted aromatic rings or substituted or unsubstituted aromatic heterocyclic rings, and the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring can be mutually connected to form a ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
2. The organic compound of claim 1, wherein the second structural unit forms a bond with the first structural unit by at least replacing a portion of the ring structure in the first structural unit specifically comprises:
The second structural unit forms a bond by substituting the A ring, the B ring or the C ring in the first structural unit; or the second structural unit forms a bond by substituting the A ring-Y in the first structural unit; or the second structural unit forms a bond by substituting the B ring-Z in the first structural unit; or the second structural unit forms a bond by substituting the A ring-Y-C ring in the first structural unit; or the second building block forms a bond by replacing the B ring-Z-C ring in the first building block.
3. The organic compound according to claim 1 or 2, wherein the polycyclic structure comprises any one of structures represented by formulas (III-1) to (III-5), or comprises a polymer formed by compositing any one or more structures represented by formulas (III-1) to (III-5):
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
4. The compound according to claim 3, wherein when the polycyclic structure comprises a polymer formed by compounding any one or more structures represented by the formulae (III-1) to (III-5), any one or more structures represented by the formulae (III-1) to (III-5) form a bond by sharing a part of the ring structures in the formulae (III-1) to (III-5).
5. The compound according to claim 3 or 4, wherein the polymer formed by compounding any one or more structures represented by the formulas (III-1) to (III-5) comprises any one of the formulas (IV-1) to (IV-21):
Wherein the A ring, B ring, C ring, D ring, E ring, F ring, G ring are independently selected from a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; the ring A, the ring B, the ring C, the ring D, the ring E, the ring F and the ring G can be mutually connected to form a ring; w is independently C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
6. The compound of any one of claims 1-5, wherein the substituted or unsubstituted aromatic ring is a substituted or unsubstituted C 6-C30 aromatic ring; the substituted or unsubstituted aromatic heterocycle is a substituted or unsubstituted C 3-C30 aromatic heterocycle;
the hetero atom in the aromatic heterocycle is one or more selected from oxygen atom, sulfur atom, nitrogen atom and selenium atom.
7. The compound of any one of claims 1-6, wherein the substituted or unsubstituted aromatic ring comprises one of 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; the substituted or unsubstituted aromatic heterocyclic ring includes one of a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted benzopyrrole 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 triazine ring, and a substituted or unsubstituted xanthone ring.
8. The organic compound of any of claims 1-7, wherein the substituents in the substituted aromatic ring, substituted aromatic heterocycle comprise one or more of deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic acid groups, isocyano groups, isocyanato groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted alkylamino groups, substituted or unsubstituted arylamino groups, substituted or unsubstituted heteroarylamino groups, substituted or unsubstituted acyl groups, substituted or unsubstituted borane groups, substituted or unsubstituted silyl groups, and substituted or unsubstituted aromatic silicon groups.
9. The organic compound of any one of claims 1-8, wherein the substituted or unsubstituted alkyl is a substituted or unsubstituted C 1-C30 alkyl; the substituted or unsubstituted cycloalkyl is a substituted or unsubstituted C 3-C30 cycloalkyl; the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C 2-C30 heterocycloalkyl; the substituted or unsubstituted alkoxy is a substituted or unsubstituted C 1-C30 alkoxy; the substituted or unsubstituted aryl is a substituted or unsubstituted C 6-C30 aryl; the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C 3-C30 heteroaryl; the substituted or unsubstituted aryloxy is a substituted or unsubstituted C 6-C30 aryloxy; the substituted or unsubstituted heteroaryloxy is a substituted or unsubstituted C 3-C30 heteroaryloxy; the substituted or unsubstituted alkylamino is a substituted or unsubstituted C 1-C30 alkylamino; the substituted or unsubstituted arylamine group is a substituted or unsubstituted C 6-C30 arylamine group; the substituted or unsubstituted heteroarylamino group is a substituted or unsubstituted C 3-C30 heteroarylamino group; the substituted or unsubstituted acyl is a substituted or unsubstituted C 1-C30 acyl; the substituted or unsubstituted aryl silicon group is a substituted or unsubstituted C 6-C30 aryl silicon group.
10. The organic compound of any one of claims 1-9, wherein at least one of said W, L 1、L2 is a nitrogen-containing group.
11. A method for producing an organic compound, comprising the steps of:
Reacting an intermediate formed by bonding a third structural unit shown in a formula (IA) and a second structural unit shown in a formula (II) with a precursor capable of providing X to introduce X into the intermediate and realize ring closure to obtain an organic compound; the organic compound comprises a polycyclic structure formed by bonding at least one first structural unit shown in a formula (I) and at least one second structural unit shown in a formula (II), wherein the second structural unit is bonded with the first structural unit by at least replacing part of a ring structure in the first structural unit;
Wherein the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring are independently selected from substituted or unsubstituted aromatic rings or substituted or unsubstituted aromatic heterocyclic rings, and the A ring, the B ring, the C ring, the D ring, the E ring, the F ring and the G ring can be mutually connected to form a ring in the organic compound; w is C (R 1), N, P, P =o or Al; x is B, N, P, P =o or Al; y, Z is independently selected from c= O, N-R 2, O, S, se, P, P = O, P =s or p=se; l 1、L2 is independently selected from a single bond or N-R 3;R1、R2、R3 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an isocyano group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy 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 acyl group, a substituted or unsubstituted borane group, a substituted or unsubstituted silane group, a substituted or unsubstituted aromatic silicon group; r 1、R2、R3 may be linked to an adjacent group to form a ring.
12. Use of the organic compounds and salts thereof according to any of claims 1-10 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.
13. A light-emitting layer, characterized in that the light-emitting layer comprises the organic compound according to any one of claims 1 to 10.
14. The light-emitting layer according to claim 13, wherein the light-emitting layer comprises a host material and a doping material, and wherein the doping material comprises the organic compound.
15. An electronic device comprising the organic compound according to any one of claims 1 to 10; or comprises a light emitting layer according to any of claims 13-14.
16. The electronic device of claim 15, 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 organic compound.
17. The electronic device of claim 15 or 16, 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.
18. A display device, characterized in that it comprises an electronic device according to any of claims 15-17; or comprises a light emitting layer according to any of claims 13-14.
19. An electronic device, characterized in that it comprises the display device of claim 18; or comprises an electronic device according to any of claims 15-17.
20. A lighting device comprising the electronic device of any one of claims 15-17; or comprises a light emitting layer according to any of claims 13-14.
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| CN202211338102.5A CN117986278A (en) | 2022-10-28 | 2022-10-28 | Organic compound and application thereof |
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| CN114478593A (en) * | 2020-10-26 | 2022-05-13 | 北京鼎材科技有限公司 | Boron-containing organic compound and organic electroluminescent device containing same |
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