WO2023207375A1 - Nitrogen-containing compound, electronic element, and electronic device - Google Patents
Nitrogen-containing compound, electronic element, and electronic device Download PDFInfo
- Publication number
- WO2023207375A1 WO2023207375A1 PCT/CN2023/081174 CN2023081174W WO2023207375A1 WO 2023207375 A1 WO2023207375 A1 WO 2023207375A1 CN 2023081174 W CN2023081174 W CN 2023081174W WO 2023207375 A1 WO2023207375 A1 WO 2023207375A1
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- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- carbon atoms
- group
- nitrogen
- Prior art date
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 115
- 239000010410 layer Substances 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 239000002346 layers by function Substances 0.000 claims description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 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 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000000463 material Substances 0.000 description 35
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- CBJHFGQCHKNNJY-UHFFFAOYSA-N 4-bromo-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2Br CBJHFGQCHKNNJY-UHFFFAOYSA-N 0.000 description 2
- GUTJITRKAMCHSD-UHFFFAOYSA-N 9,9-dimethylfluoren-2-amine Chemical compound C1=C(N)C=C2C(C)(C)C3=CC=CC=C3C2=C1 GUTJITRKAMCHSD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 2
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- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 238000010248 power generation Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical compound N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
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- 238000010898 silica gel chromatography Methods 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical class C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present application relates to the field of organic light-emitting materials, and specifically provides a nitrogen-containing compound, electronic components and electronic devices.
- OLED Organic Light Emission Diodes
- the OLED photoelectric functional material film layer that constitutes the OLED device includes at least two or more layers of structure.
- the OLED device structure used in industry includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, and an electron blocking layer.
- There are various film layers such as transport layer and electron injection layer. That is to say, the optoelectronic functional materials used in OLED devices include at least hole injection materials, hole transport materials, luminescent materials, electron transport materials, etc. The types and combinations of materials are rich. characteristics of sex and diversity.
- OLED display technology has been applied in smartphones, tablets and other fields, and will further expand to large-size applications such as TVs.
- the luminous efficiency, service life and other properties of OLED devices Still needs further improvement.
- Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device.
- OLED optoelectronic functional materials to create higher-performance OLED functional materials.
- organic OLED devices When organic OLED devices are used in display devices, the organic OLED devices are required to have long life and high efficiency.
- blue light devices in the blue pixel area (compared with red and green light-emitting devices) have higher driving voltage and shorter lifespan.
- the hole mobility and glass transition temperature of hole transport materials are increased, thereby extending the life of blue light devices and reducing device voltage.
- the purpose of this application is to provide a nitrogen-containing compound, electronic components and electronic devices.
- the nitrogen-containing compound of the present application can effectively improve the performance of electronic components.
- the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
- R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms.
- L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;
- Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;
- R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, and deuterated alkyl group with 1 to 10 carbon atoms. base, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, cycloalkyl group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms or carbon Alkylthio group with atoms 1-10.
- the present application provides an electronic component, including an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound described in the first aspect of the present application.
- the present application provides an electronic device, including the electronic component described in the second aspect of the present application.
- the nitrogen-containing compound of the present application is a triarylamine compound.
- this triarylamine compound three aromatic groups are connected with the nitrogen atom as the center.
- the first aromatic group is a 4-carbazolyl group
- the second aromatic group It is a 4-carbazolyl group connected to the nitrogen atom through an aromatic group (L), and the third one is a small-volume aromatic group (Ar).
- This combination of specific groups can make the different planes of the entire molecule have appropriate angles and form a stable spatial configuration, which not only improves the thermal stability of the compound, but also prevents the compound from crystallizing during evaporation.
- this combination of groups also enables the compound to have a suitable HOMO energy level and helps to improve the carrier (hole) injection and transport capabilities of the compound.
- Using the nitrogen-containing compound of the present application as a hole transport layer in an organic electroluminescent device can effectively improve the luminous efficiency of the device and extend the service life of the device.
- Figure 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
- Figure 2 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
- FIG. 3 is a schematic diagram of an electronic device according to an embodiment of the present application.
- FIG. 4 is a schematic diagram of an electronic device according to another embodiment of the present application.
- Electron injection layer 100. Anode; 200. Cathode; 300. Functional layer; 310. Hole injection layer; 320. Hole transport layer; 321. Electron blocking layer; 330. Organic light-emitting layer; 340. Electron transport layer; 350. Electron injection layer ; 360: photoelectric conversion layer; 400: first electronic device; 500: second electronic device.
- the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
- R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms.
- L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;
- Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;
- R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, Deuterated alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 12 carbon atoms, heteroaryl group with 5 to 12 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, carbon atoms Alkoxy group with 1-10 carbon atoms or alkylthio group with 1-10 carbon atoms.
- each... is independently selected from and “... is independently selected from” are interchangeable and should be understood in a broad sense. They can refer to the same symbol in different groups. The specific options expressed between them do not affect each other. It can also be expressed that in the same group, the specific options expressed by the same symbols do not affect each other. For example, “ Among them, each q is independently selected from 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R on the benzene ring.
- each R can be the same or different, and the options of each R" do not affect each other;
- Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings "The number of substituents q can be the same or different, each R" can be the same or different, and the options for each R" do not affect each other.
- substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituents are collectively referred to as R c ).
- substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
- the above-mentioned substituent, namely R c may be, for example, deuterium, cyano group, heteroaryl group, aryl group, alkyl group, deuterated alkyl group, cycloalkyl group, alkoxy group, alkylthio group, etc.
- the two substituents R c can exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituents R c on the functional group
- the two adjacent substituents R c may exist independently or be fused into a ring with the functional group to which they are connected. It is preferred that the two adjacent substituents R c exist independently.
- the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms.
- aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
- the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group.
- the aryl group can be a single-ring aryl group, a fused-ring aryl group, or two or more single-ring aryl groups conjugated through a carbon-carbon bond.
- Ring aryl groups monocyclic aryl groups conjugated through carbon-carbon bonds and fused-ring aryl groups, two or more fused-ring aryl groups conjugated through carbon-carbon bonds.
- the condensed ring aryl group may include, for example, bicyclic condensed aryl group (such as naphthyl), tricyclic condensed aryl group (such as phenanthrenyl, fluorenyl, anthracenyl), etc.
- Aryl groups do not contain heteroatoms such as B, N, O, S, P, Se and Si. It should be noted that both biphenyl and terphenyl groups are regarded as aryl groups in this application.
- aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl , Key et al.
- the substituted aryl group may be one or more than two hydrogen atoms in the aryl group substituted by deuterium, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl, alkyl, etc. Substituted with oxygen, alkylthio and other groups.
- the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
- a substituted aryl group with a carbon number of 18 refers to the aryl group and the substituted aryl group.
- the total number of carbon atoms in the base is 18.
- heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring.
- the heteroatom can be B , at least one of O, N, P, Si, Se and S.
- a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
- a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
- the ring system is an aromatic single ring or an aromatic fused ring.
- heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridine Aldyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine base, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thieno Thienyl, benzofuranyl,
- the substituted heteroaryl group may be one or more than two hydrogen atoms in the heteroaryl group substituted by, for example, deuterium, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl , alkoxy, alkylthio and other groups substituted. It should be understood that the number of carbon atoms of a substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
- non-located connecting bonds refer to single bonds protruding from the ring system. It means that one end of the bond can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
- the phenanthrene group represented by the formula (X') is connected to other positions of the molecule through an unpositioned bond extending from the middle of one side of the benzene ring, which represents Meaning, including any possible connection method shown in formula (X'-1) to formula (X'-4):
- a non-positioned substituent in this application refers to a substituent connected through a single bond extending from the center of the ring system, which means that the substituent can be connected at any possible position in the ring system.
- the substituent R' represented by the formula (Y) is connected to the quinoline ring through a non-positioned bond, and its meaning includes formula (Y-1) ⁇ Any possible connection method shown in formula (Y-7):
- alkyl groups with 1 to 10 carbon atoms include linear alkyl groups with 1 to 10 carbon atoms and branched chain alkyl groups with 3 to 10 carbon atoms.
- the number of carbon atoms can be 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
- alkyl groups with 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
- the number of carbon atoms of the aryl group as a substituent may be 6-12, and the number of carbon atoms is, for example, 6, 10 or 12, etc.
- Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, Naphthyl, biphenyl.
- the number of carbon atoms of the heteroaryl group as a substituent may be 5-12, and the number of carbon atoms is, for example, 5, 8, 9, 10 or 12, etc.
- Specific examples of the heteroaryl group as a substituent include but It is not limited to pyridyl group, quinolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, etc.
- the number of carbon atoms of the cycloalkyl group as a substituent may be 3-10, preferably 5-8.
- Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
- the number of carbon atoms of the deuterated alkyl group as a substituent may be 1-10, preferably 1-4.
- Specific examples of deuterated alkyl groups include, but are not limited to: trideuterated methyl.
- R 1 and R 2 can each be independently selected from an alkyl group with 1, 2, 3, 4, 5 or 6 carbon atoms, a ring group with 4, 5, 6, 7 or 8 carbon atoms.
- R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with a carbon number of 1-5, a cycloalkyl group with a carbon number of 5-8, a cycloalkyl group with a carbon number of 6 -18 substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group with 5 to 18 carbon atoms.
- R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, and an alkyl group with 6 to 15 carbon atoms.
- R 1 and R 2 are the same or different, and are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl base, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Substituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.
- the substituents in R 1 and R 2 are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 4 carbon atoms, and deuterated alkyl group with 1 to 4 carbon atoms. group, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or an alkylthio group with 1 to 4 carbon atoms.
- R 1 and R 2 are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, Naphthyl, cyclopentyl or cyclohexyl.
- R 1 and R 2 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, Substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:
- the substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and trideuterated methyl. , phenyl, naphthyl; when the number of substituents is greater than 1, each substituent may be the same or different.
- R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
- R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
- L is selected from a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.
- L can be selected from: substituted or unsubstituted arylene groups with carbon atoms of 6, 7, 8, 9, 10, 11, 12, or selected from the group consisting of carbon atoms of 5, 6, 7, 8, 9 , 10, 11, 12 substituted or unsubstituted heteroarylene groups.
- L is selected from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.
- L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted Substituted dibenzofurylene, substituted or unsubstituted dibenzothienylene.
- L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.
- each substituent in L is independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms or phenyl group.
- each substituent in L is independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl or phenyl.
- L is selected from the group consisting of:
- Ar can be selected from a substituted or unsubstituted aryl group with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.
- Substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 atoms.
- Ar is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms.
- Ar is selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 15 carbon atoms.
- Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl , substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.
- the substituents in Ar are each independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms, and 6-10 carbon atoms.
- the substituents in Ar are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, pyridyl, di Benzofuryl, dibenzothienyl or carbazolyl.
- Ar is selected from the group consisting of:
- Ar is selected from the group consisting of:
- Ar is selected from a substituted or unsubstituted aryl group with 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group with 12 to 15 carbon atoms.
- the nitrogen-containing compound serving as a hole transport layer can further improve the overall performance of the organic electroluminescent device.
- the definitions of R 1 and R 2 in Formula IA are as shown above.
- the nitrogen-containing compound is selected from the group consisting of:
- the synthesis method of the nitrogen-containing compound provided in this application is not particularly limited. Those skilled in the art can determine the appropriate synthesis method based on the preparation method provided in the synthesis examples section of the nitrogen-containing compound in this application. In other words, the Synthesis Examples section of this application exemplarily provides methods for preparing nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all nitrogen-containing compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Those skilled in the art should not understand that this application is limit.
- a second aspect of the present application provides an electronic component, including an anode, a cathode, and a functional layer 100 disposed between the anode and the cathode, wherein the functional layer includes the nitrogen-containing compound described in the first aspect of the present application. compound.
- the functional layer includes a hole transport layer containing the nitrogen-containing compound of the present application.
- the electronic component may be an organic electroluminescent device or a photoelectric conversion device.
- the electronic component is an organic electroluminescent device.
- the organic electroluminescent device includes an anode 100 , a hole transport layer 320 , an organic light-emitting layer 330 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
- the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
- anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto.
- a transparent electrode including indium tin oxide (ITO) as an anode is included.
- the hole transport layer 320 contains the nitrogen-containing compound of the present application.
- an electron blocking layer 321 (also called a "hole adjustment layer”) is disposed between the hole transport layer 320 and the organic light-emitting layer 330.
- the material of the electron blocking layer 321 may be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorenyl-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this.
- the material of the electron blocking layer is selected from at least one of the following compounds:
- the material of the electron blocking layer 321 is EB-1.
- the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material (also called a "dopant").
- the organic light-emitting layer 330 is composed of a host material and a guest material.
- the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy.
- the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
- the main material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, anthracene derivatives or other types of materials. This application does not Make special restrictions.
- the host material is selected from one or more than two of the following compounds:
- the host material of the organic light-emitting layer 330 is BH-1.
- the guest material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, a bisarylamine derivative with a condensed aromatic subunit, or other materials.
- the guest material is selected from at least one of the following compounds:
- the guest material of the organic light emitting layer 330 is composed of BD-1.
- the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials.
- the electron transport materials may generally include metal complexes and/or nitrogen-containing heterocyclic derivatives, where , the metal complex material can be selected from, for example LiQ, Alq 3 , Bepq 2 , etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton, a condensed aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc., or at least one of the following compounds:
- electron transport layer 340 is composed of ET-5 and LiQ.
- the cathode 200 includes a cathode material, which is a material with a small work function that facilitates the injection of electrons into the functional layer.
- cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.
- a hole injection layer 310 is also provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320 .
- the hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
- hole injection layer 310 is selected from the group consisting of:
- the hole injection layer 310 is composed of HAT-CN.
- an electron injection layer 350 is also provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340 .
- the electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic substance.
- the electron injection layer 350 contains LiQ or Yb.
- the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a blue light device.
- the electronic component is a photoelectric conversion device.
- the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 that are stacked in sequence.
- the hole transport layer 320 contains the nitrogen-containing compound of the present application.
- the photoelectric conversion device is a solar cell, such as an organic thin film solar cell.
- a third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.
- the electronic device is a first electronic device 400
- the first electronic device 400 includes the above-mentioned organic electroluminescent device.
- the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include but is not limited to a computer screen, a mobile phone screen, a television, electronic paper, emergency lighting, an optical module, etc.
- the electronic device is a second electronic device 500
- the second electronic device 500 includes the above-mentioned photoelectric conversion device.
- the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
- the compounds of the synthetic methods not mentioned in this application are all commercially available raw material products.
- IM I-X was synthesized according to the synthesis method of IM 1-A. The difference is that the raw material 1 in Table 1 is used instead of iodobenzene. The obtained intermediate product IM I-X and its yield are shown in Table 1.
- IM I-I was synthesized according to the synthesis method of IM I-H. The difference is that the raw material 2 in Table 2 is used instead of ethyl iodide. The obtained intermediate product IM I-I and its yield are shown in Table 2.
- Example 1 Blue organic electroluminescent device
- the anode is prepared by the following process: the thickness is
- the ITO/Ag/ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can Use ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode, and use organic solvents to clean the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate.
- HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a thickness of hole injection layer (HIL), and then vacuum evaporate compound A12 on the hole injection layer to form a thickness of hole transport layer.
- HIL hole injection layer
- compound BH-1 host
- compound BD-1 dopant
- the compound ET-5 and LiQ were co-evaporated at a weight ratio of 1:1 to form Thick electron transport layer (ETL), Yb is evaporated on the electron transport layer to form a thickness of Electron injection layer (EIL), and then magnesium (Mg) and silver (Ag) are vacuum evaporated together on the electron injection layer at an evaporation rate of 1:9 to form a thickness of the cathode.
- ETL Thick electron transport layer
- EIL Electron injection layer
- Mg magnesium
- Ag silver
- CPL organic coating layer
- An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the hole transport layer, the remaining compounds listed in Table 6 were used instead of compound A12 in Example 1.
- the hole transport layer was prepared using the same method as in Example 1, except that in Comparative Examples 1 to 4, Compound A, Compound B, Compound C and Compound D were used instead of Compound A12 in Example 1. Organic electroluminescent devices.
- the structures of the main materials used to prepare organic electroluminescent devices are as follows:
- the performance of the blue organic electroluminescent devices prepared in Examples 1-32 and Comparative Examples 1-4 was tested. Specifically, the IVL performance of the device was tested under the condition of 10mA/ cm2 . The T95 device life was at 15mA/ cm2. The test was carried out under the conditions, and the test results are shown in Table 6 below.
- using the nitrogen-containing compound of the present application as a hole transport layer in an organic electroluminescent device can further improve the luminous efficiency and service life of the device while maintaining a low driving voltage of the device.
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Abstract
The present application relates to a nitrogen-containing compound, an electronic element, and an electronic device. The nitrogen-containing compound has a structure represented by formula I, and can improve the performance of electronic elements.
Description
相关申请的交叉引用Cross-references to related applications
本申请要求于2022年4月28日递交的申请号为202210461080.5的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。This application claims priority to the Chinese patent application with application number 202210461080.5 submitted on April 28, 2022. The full text of the above Chinese patent application is hereby cited as part of this application.
本申请涉及有机发光材料领域，具体提供一种含氮化合物和电子元件及电子装置。The present application relates to the field of organic light-emitting materials, and specifically provides a nitrogen-containing compound, electronic components and electronic devices.
有机电致发光(OLED:OrganicLightEmissionDiodes)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构，产业上应用的OLED器件结构，则包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层等多种膜层，也就是说应用于OLED器件的光电功能材料至少包含空穴注入材料，空穴传输材料，发光材料，电子传输材料等，材料类型和搭配形式具有丰富性和多样性的特点。Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can be used to manufacture both new display products and new lighting products. It is expected to replace existing liquid crystal displays and fluorescent lighting, and has a wide range of application prospects. The OLED photoelectric functional material film layer that constitutes the OLED device includes at least two or more layers of structure. The OLED device structure used in industry includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, and an electron blocking layer. There are various film layers such as transport layer and electron injection layer. That is to say, the optoelectronic functional materials used in OLED devices include at least hole injection materials, hole transport materials, luminescent materials, electron transport materials, etc. The types and combinations of materials are rich. characteristics of sex and diversity.
当前，OLED显示技术已经在智能手机，平板电脑等领域获得应用，进一步还将向电视等大尺寸应用领域扩展，但是，和实际的产品应用要求相比，OLED器件的发光效率，使用寿命等性能还需要进一步提升。对于OLED发光器件提高性能的研究包括：降低器件的驱动电压，提高器件的发光效率，提高器件的使用寿命等。为了实现OLED器件的性能的不断提升，不但需要从OLED器件结构和制作工艺的创新，更需要OLED光电功能材料不断研究和创新，创制出更高性能OLED的功能材料。At present, OLED display technology has been applied in smartphones, tablets and other fields, and will further expand to large-size applications such as TVs. However, compared with actual product application requirements, the luminous efficiency, service life and other properties of OLED devices Still needs further improvement. Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to continuously improve the performance of OLED devices, it is not only necessary to innovate the OLED device structure and manufacturing process, but also to continuously research and innovate OLED optoelectronic functional materials to create higher-performance OLED functional materials.
当有机OLED器件应用于显示装置时，要求有机OLED器件具有长寿命和高效率，特别是蓝色像素区的蓝光器件(与红、绿发光器件相比)，驱动电压偏高，寿命较短。为了提升蓝色像素的寿命、降低驱动电压，提高空穴传输类材料的空穴迁移率和玻璃化转变温度，从而提升蓝光器件寿命，降低器件电压。When organic OLED devices are used in display devices, the organic OLED devices are required to have long life and high efficiency. In particular, blue light devices in the blue pixel area (compared with red and green light-emitting devices) have higher driving voltage and shorter lifespan. In order to extend the life of blue pixels and reduce the driving voltage, the hole mobility and glass transition temperature of hole transport materials are increased, thereby extending the life of blue light devices and reducing device voltage.
发明内容Contents of the invention
针对现有技术存在的上述问题，本申请的目的在于提供一种含氮化合物、电子元件和电子装置。本申请的含氮化合物能有效改善电子元件的性能。In view of the above problems existing in the prior art, the purpose of this application is to provide a nitrogen-containing compound, electronic components and electronic devices. The nitrogen-containing compound of the present application can effectively improve the performance of electronic components.
第一方面，本申请提供一种含氮化合物，所述含氮化合物的结构如式I所示：
In a first aspect, the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
In a first aspect, the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
其中，R1和R2相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为6-25的取代或未取代的芳基、碳原子数为5-25的取代或未取代的杂芳基；Wherein, R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms. Unsubstituted aryl, substituted or unsubstituted heteroaryl with 5-25 carbon atoms;
L选自碳原子数为6-18的取代或未取代的亚芳基、碳原子数为5-18的取代或未取代的亚杂芳基；L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;
Ar选自碳原子数为6-23的取代或未取代的芳基、碳原子数为5-23的取代或未取代的杂芳基；
Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;
R1、R2、L和Ar中的取代基相同或不同，且各自独立地选自氘、氰基、碳原子数为1-10的烷基、碳原子数为1-10的氘代烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基或碳原子为1-10的烷硫基。The substituents in R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, and deuterated alkyl group with 1 to 10 carbon atoms. base, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, cycloalkyl group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms or carbon Alkylthio group with atoms 1-10.
第二方面，本申请提供一种电子元件，包括阳极、阴极，以及设置在所述阳极和阴极之间的功能层，其中，所述功能层包含本申请第一方面所述的含氮化合物。In a second aspect, the present application provides an electronic component, including an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound described in the first aspect of the present application.
第三方面，本申请提供一种电子装置，包括本申请第二方面所述的电子元件。In a third aspect, the present application provides an electronic device, including the electronic component described in the second aspect of the present application.
本申请的含氮化合物为三芳胺化合物，在该三芳胺化合物中，以氮原子为中心连接了三个芳香基团，第一个芳香基团为4-咔唑基，第二个芳香基团为通过芳香基团(L)连接于氮原子上的4-咔唑基，第三个为小体积的芳香性基团(Ar)。这种特定基团的组合，可以使得整个分子的不同平面之间具有适当的夹角，形成稳定的空间构型，不仅提升化合物的热稳定性，还能防止化合物在蒸镀时出现结晶现象。此外，这种基团的组合方式还使化合物具有合适的HOMO能级，且有助于提高化合物的载流子(空穴)的注入和传输能力。将本申请的含氮化合物作为空穴传输层用于有机电致发光器件中，能有效提高器件的发光效率并延长器件的使用寿命。The nitrogen-containing compound of the present application is a triarylamine compound. In this triarylamine compound, three aromatic groups are connected with the nitrogen atom as the center. The first aromatic group is a 4-carbazolyl group, and the second aromatic group It is a 4-carbazolyl group connected to the nitrogen atom through an aromatic group (L), and the third one is a small-volume aromatic group (Ar). This combination of specific groups can make the different planes of the entire molecule have appropriate angles and form a stable spatial configuration, which not only improves the thermal stability of the compound, but also prevents the compound from crystallizing during evaporation. In addition, this combination of groups also enables the compound to have a suitable HOMO energy level and helps to improve the carrier (hole) injection and transport capabilities of the compound. Using the nitrogen-containing compound of the present application as a hole transport layer in an organic electroluminescent device can effectively improve the luminous efficiency of the device and extend the service life of the device.
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。Other features and advantages of the present application will be described in detail in the following detailed description.
图1是本申请一种实施方式的有机电致发光器件的结构示意图。Figure 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
图2是本申请一种实施方式的光电转化器件的结构示意图。Figure 2 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
图3是本申请一种实施方式的电子装置的示意图。FIG. 3 is a schematic diagram of an electronic device according to an embodiment of the present application.
图4是本申请另一种实施方式的电子装置的示意图。FIG. 4 is a schematic diagram of an electronic device according to another embodiment of the present application.
附图标记说明Explanation of reference signs
100、阳极；200、阴极；300、功能层；310、空穴注入层；320、空穴传输层；321、电子阻挡层；330、有机发光层；340、电子传输层；350、电子注入层；360：光电转化层；400：第一电子装置；500：第二电子装置。100. Anode; 200. Cathode; 300. Functional layer; 310. Hole injection layer; 320. Hole transport layer; 321. Electron blocking layer; 330. Organic light-emitting layer; 340. Electron transport layer; 350. Electron injection layer ; 360: photoelectric conversion layer; 400: first electronic device; 500: second electronic device.
以下结合附图对本申请的具体实施方式进行详细说明。应当理解地是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。Specific embodiments of the present application will be described in detail below with reference to the accompanying drawings. It should be understood that the specific embodiments described here are only used to illustrate and explain the present application, and are not used to limit the present application.
第一方面，本申请提供一种含氮化合物，所述含氮化合物的结构如式I所示：
In a first aspect, the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
In a first aspect, the application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Formula I:
其中，R1和R2相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为6-25的取代或未取代的芳基、碳原子数为5-25的取代或未取代的杂芳基；Wherein, R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms. Unsubstituted aryl, substituted or unsubstituted heteroaryl with 5-25 carbon atoms;
L选自碳原子数为6-18的取代或未取代的亚芳基、碳原子数为5-18的取代或未取代的亚杂芳基；L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;
Ar选自碳原子数为6-23的取代或未取代的芳基、碳原子数为5-23的取代或未取代的杂芳基；Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;
R1、R2、L和Ar中的取代基相同或不同，且各自独立地选自氘、氰基、碳原子数为1-10的烷基、
碳原子数为1-10的氘代烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基或碳原子为1-10的烷硫基。The substituents in R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, Deuterated alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 12 carbon atoms, heteroaryl group with 5 to 12 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, carbon atoms Alkoxy group with 1-10 carbon atoms or alkylthio group with 1-10 carbon atoms.
本申请中，所采用的描述方式“各……独立地选自”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。举例来讲，“其中，各q独立地选自0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同或不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。In this application, the description methods "each... is independently selected from" and "... is independently selected from" are interchangeable and should be understood in a broad sense. They can refer to the same symbol in different groups. The specific options expressed between them do not affect each other. It can also be expressed that in the same group, the specific options expressed by the same symbols do not affect each other. For example, " Among them, each q is independently selected from 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R on the benzene ring. ", each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings "The number of substituents q can be the same or different, each R" can be the same or different, and the options for each R" do not affect each other.
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基，即Rc，例如可以为氘、氰基、杂芳基、芳基、烷基、氘代烷基、环烷基、烷氧基、烷硫基等。当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环，优选两个相邻的两个取代基Rc独立地存在。另外，取代或未取代的官能团的碳原子数，指的是所有碳原子数。In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituents are collectively referred to as R c ). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent, namely R c , may be, for example, deuterium, cyano group, heteroaryl group, aryl group, alkyl group, deuterated alkyl group, cycloalkyl group, alkoxy group, alkylthio group, etc. When there are two substituents R c connected to the same atom, the two substituents R c can exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituents R c on the functional group When , the two adjacent substituents R c may exist independently or be fused into a ring with the functional group to which they are connected. It is preferred that the two adjacent substituents R c exist independently. In addition, the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms.
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。需要说明地是，联苯基、三联苯基在本申请中均视为芳基。芳基的实例包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、基等。In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group. In other words, the aryl group can be a single-ring aryl group, a fused-ring aryl group, or two or more single-ring aryl groups conjugated through a carbon-carbon bond. Ring aryl groups, monocyclic aryl groups conjugated through carbon-carbon bonds and fused-ring aryl groups, two or more fused-ring aryl groups conjugated through carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in this application. Among them, the condensed ring aryl group may include, for example, bicyclic condensed aryl group (such as naphthyl), tricyclic condensed aryl group (such as phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl groups do not contain heteroatoms such as B, N, O, S, P, Se and Si. It should be noted that both biphenyl and terphenyl groups are regarded as aryl groups in this application. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl , Key et al.
在本申请中，取代的芳基可以是芳基中的一个或者两个以上的氢原子被诸如氘、氰基、芳基、杂芳基、烷基、环烷基、氘代烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。In this application, the substituted aryl group may be one or more than two hydrogen atoms in the aryl group substituted by deuterium, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl, alkyl, etc. Substituted with oxygen, alkylthio and other groups. It should be understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with a carbon number of 18 refers to the aryl group and the substituted aryl group. The total number of carbon atoms in the base is 18.
在本申请中，杂芳基是指环中包含1个、2个、3个、4个、5个、6个或更多个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基
等，而不限于此。本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。In this application, heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring. The heteroatom can be B , at least one of O, N, P, Si, Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic The ring system is an aromatic single ring or an aromatic fused ring. Exemplarily, heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridine Aldyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine base, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thieno Thienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silicon fluorenyl, dibenzofuranyl and N-phenylcarbazolyl, N-pyridyl Carbazolyl, N-methylcarbazolyl etc., but not limited to this. In this application, the heteroarylene group refers to a bivalent group formed by the heteroaryl group further losing one hydrogen atom.
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上的氢原子被诸如氘、氰基、芳基、杂芳基、烷基、环烷基、氘代烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。In this application, the substituted heteroaryl group may be one or more than two hydrogen atoms in the heteroaryl group substituted by, for example, deuterium, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl , alkoxy, alkylthio and other groups substituted. It should be understood that the number of carbon atoms of a substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
本申请中，不定位连接键是指从环体系中伸出的单键其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。举例而言，如下式(X')中所示地，式(X')所表示的菲基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式：
In this application, non-located connecting bonds refer to single bonds protruding from the ring system. It means that one end of the bond can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (X'), the phenanthrene group represented by the formula (X') is connected to other positions of the molecule through an unpositioned bond extending from the middle of one side of the benzene ring, which represents Meaning, including any possible connection method shown in formula (X'-1) to formula (X'-4):
In this application, non-located connecting bonds refer to single bonds protruding from the ring system. It means that one end of the bond can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (X'), the phenanthrene group represented by the formula (X') is connected to other positions of the molecule through an unpositioned bond extending from the middle of one side of the benzene ring, which represents Meaning, including any possible connection method shown in formula (X'-1) to formula (X'-4):
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，如下式(Y)中所示地，式(Y)所表示的取代基R'通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式：
A non-positioned substituent in this application refers to a substituent connected through a single bond extending from the center of the ring system, which means that the substituent can be connected at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is connected to the quinoline ring through a non-positioned bond, and its meaning includes formula (Y-1)~ Any possible connection method shown in formula (Y-7):
A non-positioned substituent in this application refers to a substituent connected through a single bond extending from the center of the ring system, which means that the substituent can be connected at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is connected to the quinoline ring through a non-positioned bond, and its meaning includes formula (Y-1)~ Any possible connection method shown in formula (Y-7):
在本申请中，碳原子数为1-10的烷基包括碳原子数1-10的直链烷基和碳原子数为3-10的支链烷基，碳原子数可以为1、2、3、4、5、6、7、8、9或10。碳原子数为1-10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。In this application, alkyl groups with 1 to 10 carbon atoms include linear alkyl groups with 1 to 10 carbon atoms and branched chain alkyl groups with 3 to 10 carbon atoms. The number of carbon atoms can be 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. Specific examples of alkyl groups with 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
在本申请中，作为取代基的芳基的碳原子数可以为6-12，碳原子数例如为6、10或12等，作为取代基的芳基的具体实例包括但不限于，苯基、萘基、联苯基。In this application, the number of carbon atoms of the aryl group as a substituent may be 6-12, and the number of carbon atoms is, for example, 6, 10 or 12, etc. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, Naphthyl, biphenyl.
在本申请中，作为取代基的杂芳基的碳原子数可以为5-12，碳原子数例如为5、8、9、10或12等，作为取代基的杂芳基的具体实例包括但不限于，吡啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、咔唑基等。In this application, the number of carbon atoms of the heteroaryl group as a substituent may be 5-12, and the number of carbon atoms is, for example, 5, 8, 9, 10 or 12, etc. Specific examples of the heteroaryl group as a substituent include but It is not limited to pyridyl group, quinolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, etc.
在本申请中，作为取代基的环烷基的碳原子数可以为3-10，优选为5-8。环烷基的具体实例包括但不限于，环戊基、环己基等。In this application, the number of carbon atoms of the cycloalkyl group as a substituent may be 3-10, preferably 5-8. Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
在本申请中，作为取代基的氘代烷基的碳原子数可以为1-10，优选为1-4。氘代烷基的具体实例包括但不限于：三氘代甲基。In this application, the number of carbon atoms of the deuterated alkyl group as a substituent may be 1-10, preferably 1-4. Specific examples of deuterated alkyl groups include, but are not limited to: trideuterated methyl.
在本申请中，R1、R2可以各自独立地选自碳原子数为1、2、3、4、5或6的烷基，碳原子数为4、5、6、7或8的环烷基，碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19或20的取代或未取代的芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17或18的取代或
未取代的杂芳基。In this application, R 1 and R 2 can each be independently selected from an alkyl group with 1, 2, 3, 4, 5 or 6 carbon atoms, a ring group with 4, 5, 6, 7 or 8 carbon atoms. Alkyl, a substituted or unsubstituted aryl group with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, with 5 carbon atoms , 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 in place of or Unsubstituted heteroaryl.
在一种实施方式中，R1和R2相同或不同，且各自独立地选自碳原子数为1-5的烷基、碳原子数为5-8的环烷基、碳原子数为6-18的取代或未取代的芳基、碳原子数为5-18的取代或未取代的杂芳基。In one embodiment, R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with a carbon number of 1-5, a cycloalkyl group with a carbon number of 5-8, a cycloalkyl group with a carbon number of 6 -18 substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group with 5 to 18 carbon atoms.
可选地，R1和R2相同或不同，且各自独立地选自碳原子数为1-4的烷基、碳原子数为5-8的环烷基、碳原子数为6-15的取代或未取代的芳基、碳原子数为12-15的取代或未取代的杂芳基。Alternatively, R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, and an alkyl group with 6 to 15 carbon atoms. Substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 12-15 carbon atoms.
在一种实施方式中，R1和R2相同或不同，且各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环戊基、环己基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的吡啶基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基。In one embodiment, R 1 and R 2 are the same or different, and are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl base, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Substituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.
可选地，R1和R2中的取代基相同或不同，且各自独立地选自氘、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氘代烷基、碳原子数为6-10的芳基、碳原子数为5-8的环烷基、碳原子数为1-4的烷氧基或碳原子为1-4的烷硫基。Optionally, the substituents in R 1 and R 2 are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 4 carbon atoms, and deuterated alkyl group with 1 to 4 carbon atoms. group, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or an alkylthio group with 1 to 4 carbon atoms.
可选地，R1和R2中的取代基各自独立地选自氘、氰基、甲基、乙基、正丙基、异丙基、叔丁基、三氘代甲基、苯基、萘基、环戊基或环己基。Alternatively, the substituents in R 1 and R 2 are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, Naphthyl, cyclopentyl or cyclohexyl.
在一种实施方式中，R1和R2各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环戊基、环己基、取代或未取代的基团W，其中，未取代的基团W选自以下基团所组成的组：
In one embodiment, R 1 and R 2 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, Substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:
In one embodiment, R 1 and R 2 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, Substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:
取代的基团W中具有一个或两个以上取代基，取代基各自独立地选自氘、氰基、甲基、乙基、正丙基、异丙基、叔丁基、三氘代甲基、苯基、萘基；当取代基的个数大于1时，各取代基相同或不同。The substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and trideuterated methyl. , phenyl, naphthyl; when the number of substituents is greater than 1, each substituent may be the same or different.
可选地，R1和R2各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和以下基团所组成的组：
Alternatively, R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
Alternatively, R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
进一步可选地，R1和R2各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和以下基团所组成的组：
Further optionally, R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
Further optionally, R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the following groups:
可选地，L选自碳原子数为6-12的取代或未取代的亚芳基、碳原子数为5-12的取代或未取代的亚杂芳基。例如，L可以选自：碳原子数为6、7、8、9、10、11、12的取代或未取代的亚芳基，或者选自碳原子数为5、6、7、8、9、10、11、12的取代或未取代的亚杂芳基。Alternatively, L is selected from a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms. For example, L can be selected from: substituted or unsubstituted arylene groups with carbon atoms of 6, 7, 8, 9, 10, 11, 12, or selected from the group consisting of carbon atoms of 5, 6, 7, 8, 9 , 10, 11, 12 substituted or unsubstituted heteroarylene groups.
进一步可选地，L选自碳原子数为6-12的取代或未取代的亚芳基。Further optionally, L is selected from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.
在一种实施方式中，L选自取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基。In one embodiment, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted Substituted dibenzofurylene, substituted or unsubstituted dibenzothienylene.
进一步可选地，L选自取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基。Further optionally, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.
可选地，L中的取代基各自独立地选自氘、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氘代烷基或苯基。Alternatively, each substituent in L is independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms or phenyl group.
进一步可选地，L中的取代基各自独立地选自氘、氰基、甲基、乙基、异丙基、叔丁基、三氘代甲基或苯基。Further optionally, each substituent in L is independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl or phenyl.
在一种具体的实施方式中，L选自以下基团所组成的组：
In a specific embodiment, L is selected from the group consisting of:
In a specific embodiment, L is selected from the group consisting of:
本申请中，Ar可以选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19或20取代或未取代的芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17或18的取代或未取代的杂芳基。In this application, Ar can be selected from a substituted or unsubstituted aryl group with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms. Substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 atoms.
可选地，Ar选自碳原子数为6-18的取代或未取代的芳基、碳原子数为5-18的取代或未取代的杂芳基。Alternatively, Ar is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms.
进一步可选地，Ar选自碳原子数为6-15的取代或未取代的芳基、碳原子数为12-15的取代或未取代的杂芳基。Further optionally, Ar is selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 15 carbon atoms.
在一种实施方式中，Ar选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的三联苯基、取代或未取代的吡啶基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基。In one embodiment, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl , substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.
可选地，Ar中的取代基各自独立地选自氘、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氘代烷基、碳原子数为6-10的芳基、碳原子数为5-12的杂芳基。Optionally, the substituents in Ar are each independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms, and 6-10 carbon atoms. Aryl groups and heteroaryl groups with 5-12 carbon atoms.
进一步可选地，Ar中的取代基各自独立地选自氘、氰基、甲基、乙基、异丙基、叔丁基、三氘代甲基、苯基、萘基、吡啶基、二苯并呋喃基、二苯并噻吩基或咔唑基。Further optionally, the substituents in Ar are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, pyridyl, di Benzofuryl, dibenzothienyl or carbazolyl.
在一种具体的实施方式中，Ar选自以下基团所组成的组：
In a specific embodiment, Ar is selected from the group consisting of:
In a specific embodiment, Ar is selected from the group consisting of:
可选地，Ar选自以下基团所组成的组：
Optionally, Ar is selected from the group consisting of:
Optionally, Ar is selected from the group consisting of:
在一种优选的实施方式中，所述含氮化合物的结构如式IA所示：
In a preferred embodiment, the structure of the nitrogen-containing compound is shown in formula IA:
In a preferred embodiment, the structure of the nitrogen-containing compound is shown in formula IA:
其中，Ar选自碳原子数为6-15的取代或未取代的芳基、碳原子数为12-15的取代或未取代的杂芳基。该实施方式中，所述含氮化合物作为空穴传输层能进一步提高有机电致发光器件的综合性能。式IA中的R1、R2的定义如上文所示。
Wherein, Ar is selected from a substituted or unsubstituted aryl group with 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group with 12 to 15 carbon atoms. In this embodiment, the nitrogen-containing compound serving as a hole transport layer can further improve the overall performance of the organic electroluminescent device. The definitions of R 1 and R 2 in Formula IA are as shown above.
可选地，所述含氮化合物选自以下化合物所组成的组：
Optionally, the nitrogen-containing compound is selected from the group consisting of:
Optionally, the nitrogen-containing compound is selected from the group consisting of:
本申请对提供的含氮化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的含氮化合物结合合成例部分提供的制备方法确定合适的合成方法。换言之，本申请的合成例部分示例性地提供了含氮化合物的制备方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有含氮化合物，在此不再详述制备该含氮化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。The synthesis method of the nitrogen-containing compound provided in this application is not particularly limited. Those skilled in the art can determine the appropriate synthesis method based on the preparation method provided in the synthesis examples section of the nitrogen-containing compound in this application. In other words, the Synthesis Examples section of this application exemplarily provides methods for preparing nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all nitrogen-containing compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Those skilled in the art should not understand that this application is limit.
本申请第二方面提供一种电子元件，包括阳极、阴极，以及设置在所述阳极与所述阴极之间的功能层100，其中，所述功能层包含本申请第一方面所述的含氮化合物。A second aspect of the present application provides an electronic component, including an anode, a cathode, and a functional layer 100 disposed between the anode and the cathode, wherein the functional layer includes the nitrogen-containing compound described in the first aspect of the present application. compound.
可选地，所述功能层包括空穴传输层，所述空穴传输层包含本申请的含氮化合物。Optionally, the functional layer includes a hole transport layer containing the nitrogen-containing compound of the present application.
本申请中，所述电子元件可以为有机电致发光器件或光电转化器件。In this application, the electronic component may be an organic electroluminescent device or a photoelectric conversion device.
按照一种具体的实施方式，所述电子元件为有机电致发光器件。如图1所示，所述有机电致发光器件包括依次层叠设置的阳极100、空穴传输层320、有机发光层330、电子传输层340和阴极200。According to a specific implementation, the electronic component is an organic electroluminescent device. As shown in FIG. 1 , the organic electroluminescent device includes an anode 100 , a hole transport layer 320 , an organic light-emitting layer 330 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
本申请中，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indiumtin oxide)(ITO)作为阳极的透明电极。In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as an anode is included.
可选地，所述空穴传输层320包含本申请的含氮化合物。Optionally, the hole transport layer 320 contains the nitrogen-containing compound of the present application.
可选地，所述空穴传输层320与有机发光层330之间还设有电子阻挡层321(也称为“空穴调整层”)。所述电子阻挡层321的材料可以选自咔唑多聚体、咔唑连接芳胺类化合物、二苯并呋喃连接芳胺类化合物、取代的芴基连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。例如，所述电子阻挡层的材料选自以下化合物中的至少一种：
Optionally, an electron blocking layer 321 (also called a "hole adjustment layer") is disposed between the hole transport layer 320 and the organic light-emitting layer 330. The material of the electron blocking layer 321 may be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorenyl-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this. For example, the material of the electron blocking layer is selected from at least one of the following compounds:
Optionally, an electron blocking layer 321 (also called a "hole adjustment layer") is disposed between the hole transport layer 320 and the organic light-emitting layer 330. The material of the electron blocking layer 321 may be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorenyl-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this. For example, the material of the electron blocking layer is selected from at least one of the following compounds:
在一种具体的实施方式中，所述电子阻挡层321的材料为EB-1。In a specific implementation, the material of the electron blocking layer 321 is EB-1.
有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料(也称“掺杂剂”)。可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330内复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
The organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material (also called a "dopant"). Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy. To the host material, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物、蒽类衍生物或者其他类型的材料，本申请对此不做特殊的限制。例如，所述主体材料选自以下化合物中的一种或两种以上：
The main material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, anthracene derivatives or other types of materials. This application does not Make special restrictions. For example, the host material is selected from one or more than two of the following compounds:
The main material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, anthracene derivatives or other types of materials. This application does not Make special restrictions. For example, the host material is selected from one or more than two of the following compounds:
在一种具体的实施方式中，有机发光层330的主体材料为BH-1。In a specific implementation, the host material of the organic light-emitting layer 330 is BH-1.
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、具有稠合芳香亚基的双芳胺衍生物或者其他材料，本申请对此不做特殊的限制。例如，所述客体材料选自以下化合物中的至少一种：
The guest material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, a bisarylamine derivative with a condensed aromatic subunit, or other materials. There are no special restrictions on this application. For example, the guest material is selected from at least one of the following compounds:
The guest material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, a bisarylamine derivative with a condensed aromatic subunit, or other materials. There are no special restrictions on this application. For example, the guest material is selected from at least one of the following compounds:
在一种具体的实施方式中，有机发光层330的客体材料由BD-1组成。In a specific implementation, the guest material of the organic light emitting layer 330 is composed of BD-1.
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料通常可以包含金属络合物和/或含氮杂环衍生物，其中，所述金属络合物材料例如可以选自
LiQ、Alq3、Bepq2等；所述含氮杂环衍生物可以为具有含氮六元环或五元环骨架的芳香族环、具有含氮六元环或五元环骨架的稠合芳香族环化合物等，具体实例包括但不限于，BCP、Bphen、NBphen、DBimiBphen、BimiBphen等1,10-菲咯啉类化合物，或者以下化合物中的至少一种：
The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may generally include metal complexes and/or nitrogen-containing heterocyclic derivatives, where , the metal complex material can be selected from, for example LiQ, Alq 3 , Bepq 2 , etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton, a condensed aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc., or at least one of the following compounds:
The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may generally include metal complexes and/or nitrogen-containing heterocyclic derivatives, where , the metal complex material can be selected from, for example LiQ, Alq 3 , Bepq 2 , etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton, a condensed aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc., or at least one of the following compounds:
在一种具体的实施方式中，电子传输层340由ET-5和LiQ组成。In a specific embodiment, electron transport layer 340 is composed of ET-5 and LiQ.
本申请中，阴极200包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO2/Al、LiF/Ca、LiF/Al和BaF2/Ca。优选包括包含镁和银的金属电极作为阴极。In this application, the cathode 200 includes a cathode material, which is a material with a small work function that facilitates the injection of electrons into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.
可选地，如图1所示，在阳极100和空穴传输层320之间还设置有空穴注入层310，以增强向空穴传输层320注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310选自以下化合物所组成的组：
Optionally, as shown in FIG. 1 , a hole injection layer 310 is also provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320 . The hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application. For example, hole injection layer 310 is selected from the group consisting of:
Optionally, as shown in FIG. 1 , a hole injection layer 310 is also provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320 . The hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application. For example, hole injection layer 310 is selected from the group consisting of:
在一种具体的实施方式中，空穴注入层310由HAT-CN组成。In a specific implementation, the hole injection layer 310 is composed of HAT-CN.
可选地，如图1所示，在阴极200和电子传输层340之间还设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。例如，电子注入层350包含LiQ或Yb。Optionally, as shown in FIG. 1 , an electron injection layer 350 is also provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340 . The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 contains LiQ or Yb.
本申请中，所述有机电致发光器件可以为蓝光器件、红光器件或绿光器件，优选为蓝光器件。In this application, the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a blue light device.
按照另一种实施方式，电子元件为光电转化器件。如图3所示，光电转化器件可包括依次层叠设置的阳极100、空穴传输层320、光电转化层360、电子传输层340和阴极200。其中，所述空穴传输层320包含本申请的含氮化合物。According to another embodiment, the electronic component is a photoelectric conversion device. As shown in FIG. 3 , the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 that are stacked in sequence. Wherein, the hole transport layer 320 contains the nitrogen-containing compound of the present application.
可选地，光电转化器件为太阳能电池，例如为有机薄膜太阳能电池。Optionally, the photoelectric conversion device is a solar cell, such as an organic thin film solar cell.
本申请第三方面提供一种电子装置，包括本申请第二方面所述的电子元件。A third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
According to one embodiment, as shown in FIG. 2 , the electronic device is a first electronic device 400 , and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include but is not limited to a computer screen, a mobile phone screen, a television, electronic paper, emergency lighting, an optical module, etc.
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。According to another embodiment, as shown in FIG. 4 , the electronic device is a second electronic device 500 , and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
以下，通过实施例对本申请进一步详细说明。但是，下述实施例仅是本申请的例示，而并非限定本申请。Hereinafter, the present application will be further described in detail through examples. However, the following examples are only examples of the present application and do not limit the present application.
本申请中未提到的合成方法的化合物的都可通过商业途径获得的原料产品。The compounds of the synthetic methods not mentioned in this application are all commercially available raw material products.
一、中间体的合成1. Synthesis of intermediates
1、中间体IM I-X的合成：1. Synthesis of intermediate IM I-X:
以IM I-A为例来说明部分IM I-X的合成
Take IM IA as an example to illustrate the synthesis of part of IM IX
Take IM IA as an example to illustrate the synthesis of part of IM IX
在氮气保护下，向500mL的三口烧瓶中依次加入4-溴咔唑(30g，121.90mmol)、碘苯(24.87g，121.89mmol)、碘化亚铜(1.16g,6.09mmol)、碳酸钾(42.05g，304.74mmol)、1,10-菲啰啉(2.19g，11.05mmol)和18-冠醚-6(1.61g,6.09mmol)，然后加入500mL的DMF，继续通氮气20min。将反应体系缓慢加热升温至回流并搅拌反应24h。反应结束后降温至室温，将反应液倒入水中用二氯甲烷萃取，萃取后用无水硫酸镁干燥30min，然后减压蒸馏除去溶剂，用二氯甲烷/石油醚(体积比为1：2)过硅胶色谱柱，得到为灰白色固体的中间体IM I-A(30.28g，收率：77.1％)。Under nitrogen protection, add 4-bromocarbazole (30g, 121.90mmol), iodobenzene (24.87g, 121.89mmol), copper iodide (1.16g, 6.09mmol), potassium carbonate ( 42.05g, 304.74mmol), 1,10-phenanthroline (2.19g, 11.05mmol) and 18-crown ether-6 (1.61g, 6.09mmol), then add 500mL of DMF, and continue to vent nitrogen for 20min. The reaction system was slowly heated to reflux and stirred for 24 h. After the reaction is completed, the temperature is cooled to room temperature, and the reaction solution is poured into water and extracted with dichloromethane. After extraction, it is dried with anhydrous magnesium sulfate for 30 minutes, and then the solvent is distilled off under reduced pressure, and the mixture is distilled with dichloromethane/petroleum ether (volume ratio is 1:2). ) was passed through a silica gel chromatography column to obtain intermediate IM I-A (30.28g, yield: 77.1%) as an off-white solid.
参照IM 1-A的合成方法合成IM I-X，不同之处在于，用表1中的原料1代替碘苯，所得中间体产物IM I-X及收率见表1。IM I-X was synthesized according to the synthesis method of IM 1-A. The difference is that the raw material 1 in Table 1 is used instead of iodobenzene. The obtained intermediate product IM I-X and its yield are shown in Table 1.
表1
Table 1
Table 1
中间体IM I-H合成：
Intermediate IM IH synthesis:
Intermediate IM IH synthesis:
在氮气保护下，向250mL三口烧瓶中投入4-溴咔唑(20g，81.26mmol)、KOH(18.23g，325.06mmol)、甲苯(120mL)以及聚乙二醇400(2mL)，保持温度在30-35℃，搅拌充分后，滴加碘乙烷(19.01g,121.90mmol)。滴加完毕后，恒温反应3h。反应结束后将反应液抽滤，固相用甲苯冲洗，回收液相，合并液相得到有机相，将所得有机相并水洗至中性，加入硫酸钠干燥，减压蒸除溶剂，得黄白色固体物质，使用乙醇对固体产物进行重结晶，得到中间体IM I-H(13.97g，收率：62.7％)。Under nitrogen protection, put 4-bromocarbazole (20g, 81.26mmol), KOH (18.23g, 325.06mmol), toluene (120mL) and polyethylene glycol 400 (2mL) into a 250mL three-necked flask, keeping the temperature at 30 -35°C, after stirring thoroughly, add ethyl iodide (19.01g, 121.90mmol) dropwise. After the dropwise addition is completed, react at a constant temperature for 3 hours. After the reaction, filter the reaction solution, rinse the solid phase with toluene, recover the liquid phase, combine the liquid phases to obtain an organic phase, wash the obtained organic phase with water until neutral, add sodium sulfate to dry, and evaporate the solvent under reduced pressure to obtain a yellow-white color. The solid material was recrystallized using ethanol to obtain the intermediate IM I-H (13.97g, yield: 62.7%).
参照IM I-H的合成方法合成IM I-I，不同之处在于，使用表2中的原料2代替碘乙烷，所得中间体产物IM I-I及收率见表2。IM I-I was synthesized according to the synthesis method of IM I-H. The difference is that the raw material 2 in Table 2 is used instead of ethyl iodide. The obtained intermediate product IM I-I and its yield are shown in Table 2.
表2
Table 2
Table 2
2、中间体IM I-Y-Z2. Intermediate IM I-Y-Z
以IM I-A-1为例说明IM I-Y-Z的合成
Taking IM IA-1 as an example to illustrate the synthesis of IM IYZ
Taking IM IA-1 as an example to illustrate the synthesis of IM IYZ
在氮气保护下，向500mL三口烧瓶中投入IM I-A(20.00g,62.07mmol)，对氯苯硼酸(14.56g,93.11mmol)，K2CO3(17.16g，124.14mmol)、四丁基溴化铵(4.01g，12.41mmol)、甲苯(160mL)、乙醇(40mL)和水(40mL)，开启搅拌并充氮气保护30min，加热升温至50℃-60℃，然后加入Pd(PPh3)4(1.44g,1.24mmol)，继续升温至70℃-75℃回流反应24h。反应结束后降至室温，用二氯甲烷萃取，收集有机相，将有机相水洗至中性后，干燥，过滤，浓缩，用甲苯和正庚烷混合溶剂重结晶，烘干得白色固体，即
IM I-A-1(14.05g，收率：64.0％)。Under nitrogen protection, put IM IA (20.00g, 62.07mmol), p-chlorophenylboronic acid (14.56g, 93.11mmol), K 2 CO 3 (17.16g, 124.14mmol), and tetrabutyl bromide into a 500mL three-necked flask. Ammonium (4.01g, 12.41mmol), toluene (160mL), ethanol (40mL) and water (40mL), start stirring and fill with nitrogen for 30min, heat to 50℃-60℃, then add Pd(PPh 3 ) 4 ( 1.44g, 1.24mmol), continue to raise the temperature to 70℃-75℃ and reflux for 24h. After the reaction is completed, it is lowered to room temperature, extracted with dichloromethane, and the organic phase is collected. The organic phase is washed with water until neutral, dried, filtered, concentrated, recrystallized with a mixed solvent of toluene and n-heptane, and dried to obtain a white solid, namely IM IA-1 (14.05g, yield: 64.0%).
参照IM I-A-1的合成方法合成合成IM I-Y-1，不同之处在于，用表3中的原料3代替IM I-A，用原料4代替对氯苯硼酸，所得中间体产物IM I-Y-Z及收率见表3。Refer to the synthesis method of IM I-A-1 to synthesize IM I-Y-1. The difference is that the raw material 3 in Table 3 is used instead of IM I-A, and the raw material 4 is used instead of p-chlorophenylboronic acid. The obtained intermediate product IM I-Y-Z and the yield are shown in table 3.
表3
table 3
table 3
二、化合物的合成2. Synthesis of compounds
合成例1：化合物A12的合成
Synthesis Example 1: Synthesis of Compound A12
Synthesis Example 1: Synthesis of Compound A12
(1)在氮气保护下，向500mL三口烧瓶中投入IM I-A(20g，62.07mmol)、2-氨基-9,9-二甲基芴(12.99g，62.07mmol)和甲苯(160mL)，升温至110℃，待原料溶清后，降温至70℃，依次加入Pd2(dba)3(0.57g,0.62mmol)、X-Phos(0.59g，1.24mmol)和叔丁醇钠(8.95g，93.11mmol)，升温回流2h，然后降至室温，水洗3次，加入10g无水硫酸镁干燥除水，静置30min，抽滤浓缩。过柱层析色谱柱纯化，得到中间体IM I-A-O(21.03g，收率：75.2％)。
(1) Under nitrogen protection, put IM IA (20g, 62.07mmol), 2-amino-9,9-dimethylfluorene (12.99g, 62.07mmol) and toluene (160mL) into a 500mL three-necked flask, and heat to 110°C. After the raw materials are dissolved, cool down to 70°C and add Pd 2 (dba) 3 (0.57g, 0.62mmol), X-Phos (0.59g, 1.24mmol) and sodium tert-butoxide (8.95g, 93.11 mmol), raise the temperature and reflux for 2 hours, then reduce to room temperature, wash with water three times, add 10g of anhydrous magnesium sulfate to dry and remove water, let stand for 30 minutes, and then concentrate by suction filtration. It was purified by column chromatography to obtain the intermediate IM IAO (21.03g, yield: 75.2%).
(1) Under nitrogen protection, put IM IA (20g, 62.07mmol), 2-amino-9,9-dimethylfluorene (12.99g, 62.07mmol) and toluene (160mL) into a 500mL three-necked flask, and heat to 110°C. After the raw materials are dissolved, cool down to 70°C and add Pd 2 (dba) 3 (0.57g, 0.62mmol), X-Phos (0.59g, 1.24mmol) and sodium tert-butoxide (8.95g, 93.11 mmol), raise the temperature and reflux for 2 hours, then reduce to room temperature, wash with water three times, add 10g of anhydrous magnesium sulfate to dry and remove water, let stand for 30 minutes, and then concentrate by suction filtration. It was purified by column chromatography to obtain the intermediate IM IAO (21.03g, yield: 75.2%).
(2)在氮气保护下，向500mL三口烧瓶中投入IM I-A-O(20.00g，44.38mmol)、IM I-A-1(15.71g，44.39mmol)和甲苯(160mL)，升温至110℃，待原料溶清后，降温至70℃，依次加入Pd2(dba)3(0.41g，0.45mmol)、S-Phos(0.36g，0.89mmol)和叔丁醇钠(6.40g，66.58mmol)，升温回流反应2h。反应结束后降至室温，将反应液水洗3次，然后加入10g无水硫酸镁干燥除水，静置30min，抽滤浓缩。将浓缩液过柱层析色谱柱纯化，得到化合物A12(21.20g，收率：62.2％)；质谱：m/z＝768.3[M+H]+。(2) Under nitrogen protection, put IM IAO (20.00g, 44.38mmol), IM IA-1 (15.71g, 44.39mmol) and toluene (160mL) into a 500mL three-necked flask, raise the temperature to 110°C, wait until the raw materials are dissolved Afterwards, the temperature was lowered to 70°C, Pd 2 (dba) 3 (0.41g, 0.45mmol), S-Phos (0.36g, 0.89mmol) and sodium tert-butoxide (6.40g, 66.58mmol) were added in sequence, and the temperature was raised to reflux for 2 hours. . After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was washed three times with water, then 10 g of anhydrous magnesium sulfate was added to dry it to remove water, left to stand for 30 minutes, and then concentrated by suction filtration. The concentrated solution was purified by column chromatography to obtain compound A12 (21.20g, yield: 62.2%); mass spectrum: m/z=768.3[M+H] + .
合成例2～32Synthesis Examples 2 to 32
参照化合物A12的合成方法合成下表所列的化合物，不同之处在于，使用表4中的原料5代替2-氨基-9,9-二甲基芴，使用原料6代替IM I-A，使用原料7代替IM I-A-1，所合成的化合物及其总收率和质谱结果如表4所示。Compounds listed in the table below were synthesized with reference to the synthesis method of compound A12. The difference is that raw material 5 in Table 4 was used instead of 2-amino-9,9-dimethylfluorene, raw material 6 was used instead of IM I-A, and raw material 7 was used Instead of IM I-A-1, the synthesized compounds, their overall yields and mass spectrometry results are shown in Table 4.
表4
Table 4
Table 4
化合物的核磁数据如表5所示。The NMR data of the compounds are shown in Table 5.
表5
table 5
table 5
有机电致发光器件的制作及评估实施例Examples of fabrication and evaluation of organic electroluminescent devices
实施例1：蓝色有机电致发光器件Example 1: Blue organic electroluminescent device
通过以下过程制备阳极：将厚度依次为的ITO/Ag/ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，并可利用紫外臭氧以及O2:N2等离子进行表面处理，以增加阳极的功函数，并采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。The anode is prepared by the following process: the thickness is The ITO/Ag/ITO substrate is cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can Use ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode, and use organic solvents to clean the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate.
在实验基板(阳极)上真空蒸镀HAT-CN以形成厚度为的空穴注入层(HIL)，然后在空穴注入层上真空蒸镀化合物A12，以形成厚度为的空穴传输层。HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a thickness of hole injection layer (HIL), and then vacuum evaporate compound A12 on the hole injection layer to form a thickness of hole transport layer.
在空穴传输层上真空蒸镀EB-1，形成厚度为的电子阻挡层。Vacuum evaporate EB-1 on the hole transport layer to form a thickness of electron blocking layer.
接着，在电子阻挡层上，将化合物BH-1(主体)和化合物BD-1(掺杂剂)以质量比97％：3％
的比例进行共同蒸镀，形成厚度为的发光层(EML)。Next, on the electron blocking layer, compound BH-1 (host) and compound BD-1 (dopant) were mixed at a mass ratio of 97%:3%. The ratio is co-evaporated to form a thickness of Emissive layer (EML).
然后，将化合物ET-5和LiQ以1:1的重量比进行共同蒸镀形成厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1:9的蒸镀速率在电子注入层上共同真空蒸镀，以形成厚度为的阴极。Then, the compound ET-5 and LiQ were co-evaporated at a weight ratio of 1:1 to form Thick electron transport layer (ETL), Yb is evaporated on the electron transport layer to form a thickness of Electron injection layer (EIL), and then magnesium (Mg) and silver (Ag) are vacuum evaporated together on the electron injection layer at an evaporation rate of 1:9 to form a thickness of the cathode.
此外，在上述阴极上真空蒸镀CP-1，形成厚度为的有机覆盖层(CPL)，从而完成蓝色有机电致发光器件的制造。In addition, CP-1 was vacuum evaporated on the above cathode to form a thickness of organic coating layer (CPL) to complete the fabrication of blue organic electroluminescent devices.
实施例2至实施例32Example 2 to Example 32
除了在制备空穴传输层时，以表6所列的其余化合物替代实施例1中的化合物A12之外，利用与实施例1相同的方法制备有机电致发光器件。An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the hole transport layer, the remaining compounds listed in Table 6 were used instead of compound A12 in Example 1.
比较例1至比较例4Comparative Example 1 to Comparative Example 4
除了在制备空穴传输层时，比较例1-比较例4中分别以化合物A、化合物B、化合物C和化合物D代替实施例1中的化合物A12之外，利用与实施例1相同的方法制备有机电致发光器件。The hole transport layer was prepared using the same method as in Example 1, except that in Comparative Examples 1 to 4, Compound A, Compound B, Compound C and Compound D were used instead of Compound A12 in Example 1. Organic electroluminescent devices.
以上实施例和比较例中，制备有机电致发光器件所使用的主要材料的结构如下：
In the above embodiments and comparative examples, the structures of the main materials used to prepare organic electroluminescent devices are as follows:
In the above embodiments and comparative examples, the structures of the main materials used to prepare organic electroluminescent devices are as follows:
对实施例1-32和比较例1-4制备所得的蓝色有机电致发光器件进行性能测试，具体在10mA/cm2的条件下测试了器件的IVL性能，T95器件寿命在15mA/cm2的条件下进行测试,测试结果展示在下表6中。The performance of the blue organic electroluminescent devices prepared in Examples 1-32 and Comparative Examples 1-4 was tested. Specifically, the IVL performance of the device was tested under the condition of 10mA/ cm2 . The T95 device life was at 15mA/ cm2. The test was carried out under the conditions, and the test results are shown in Table 6 below.
表6
Table 6
Table 6
参照上表6可知，相较于比较例1-4所制备的有机电致发光器件，实施例1-32以本申请的含氮化合物作为空穴传输层所制备的有机电致发光器件性能得到改善，主要表现为器件的电流效率至少提高了9.4％，T95寿命至少提高了10.4％。Referring to Table 6 above, it can be seen that compared with the organic electroluminescent device prepared in Comparative Examples 1-4, the performance of the organic electroluminescent device prepared in Examples 1-32 using the nitrogen-containing compound of the present application as a hole transport layer is obtained. The improvement is mainly reflected in the current efficiency of the device being increased by at least 9.4%, and the T95 life span being increased by at least 10.4%.
可见，以本申请的含氮化合物作为空穴传输层应用到有机电致发光器件中，在维持器件具有较低的驱动电压的情况下，能进一步提高器件的发光效率和使用寿命。
It can be seen that using the nitrogen-containing compound of the present application as a hole transport layer in an organic electroluminescent device can further improve the luminous efficiency and service life of the device while maintaining a low driving voltage of the device.
Claims (13)
- 含氮化合物，其结构如式I所示：
Nitrogen-containing compounds, their structures are shown in formula I:
其中，R1和R2相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为6-25的取代或未取代的芳基、碳原子数为5-25的取代或未取代的杂芳基；Wherein, R 1 and R 2 are the same or different, and are each independently selected from an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a substituted or substituted group with 6 to 25 carbon atoms. Unsubstituted aryl, substituted or unsubstituted heteroaryl with 5-25 carbon atoms;L选自碳原子数为6-18的取代或未取代的亚芳基、碳原子数为5-18的取代或未取代的亚杂芳基；L is selected from a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 18 carbon atoms;Ar选自碳原子数为6-23的取代或未取代的芳基、碳原子数为5-23的取代或未取代的杂芳基；Ar is selected from a substituted or unsubstituted aryl group with 6 to 23 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 23 carbon atoms;R1、R2、L和Ar中的取代基相同或不同，且各自独立地选自氘、氰基、碳原子数为1-10的烷基、碳原子数为1-10的氘代烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基或碳原子为1-10的烷硫基。The substituents in R 1 , R 2 , L and Ar are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 10 carbon atoms, and deuterated alkyl group with 1 to 10 carbon atoms. base, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, cycloalkyl group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms or carbon Alkylthio group with atoms 1-10. - 根据权利要求1所述的含氮化合物，其中，R1和R2相同或不同，且各自独立地选自碳原子数为1-5的烷基、碳原子数为5-8的环烷基、碳原子数为6-18的取代或未取代的芳基、碳原子数为5-18的取代或未取代的杂芳基；The nitrogen-containing compound according to claim 1, wherein R 1 and R 2 are the same or different, and each is independently selected from an alkyl group with 1 to 5 carbon atoms and a cycloalkyl group with 5 to 8 carbon atoms. , a substituted or unsubstituted aryl group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 18 carbon atoms;可选地，R1和R2中的取代基相同或不同，且各自独立地选自氘、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氘代烷基、碳原子数为6-10的芳基、碳原子数为5-8的环烷基、碳原子数为1-4的烷氧基或碳原子为1-4的烷硫基。Optionally, the substituents in R 1 and R 2 are the same or different, and are each independently selected from deuterium, cyano group, alkyl group with 1 to 4 carbon atoms, and deuterated alkyl group with 1 to 4 carbon atoms. group, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or an alkylthio group with 1 to 4 carbon atoms.
- 根据权利要求1所述的含氮化合物，其中，R1和R2相同或不同，且各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环戊基、环己基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的吡啶基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基；The nitrogen-containing compound according to claim 1, wherein R1 and R2 are the same or different, and each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted Fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl;可选地，R1和R2中的取代基各自独立地选自氘、氰基、甲基、乙基、正丙基、异丙基、叔丁基、三氘代甲基、苯基、萘基、环戊基或环己基。Alternatively, the substituents in R 1 and R 2 are each independently selected from deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, Naphthyl, cyclopentyl or cyclohexyl.
- 根据权利要求1所述的含氮化合物，其中，R1和R2相同或不同，且各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和以下基团所组成的组：
The nitrogen-containing compound according to claim 1, wherein R1 and R2 are the same or different, and each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, The group consisting of tert-butyl and the following groups:
- 根据权利要求1所述的含氮化合物，其中，L选自碳原子数为6-12的取代或未取代的亚芳基、碳原子数为5-12的取代或未取代的亚杂芳基；The nitrogen-containing compound according to claim 1, wherein L is selected from a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms. ;可选地，L中的取代基各自独立地选自氘、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氘代烷基或苯基。Alternatively, the substituents in L are each independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms or phenyl group.
- 根据权利要求1所述的含氮化合物，其中，L选自取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基；The nitrogen-containing compound according to claim 1, wherein L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene. Pyridyl, substituted or unsubstituted dibenzofurylene, substituted or unsubstituted dibenzothienylene;可选地，L中的取代基各自独立地选自氘、氰基、甲基、乙基、异丙基、叔丁基、三氘代甲基或苯基。Alternatively, each substituent in L is independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl or phenyl.
- 根据权利要求1所述的含氮化合物，其中，Ar选自碳原子数为6-18的取代或未取代的芳基、碳原子数为5-18的取代或未取代的杂芳基；The nitrogen-containing compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group with a carbon number of 6-18, a substituted or unsubstituted heteroaryl group with a carbon number of 5-18;可选地，Ar选自碳原子数为6-15的取代或未取代的芳基、碳原子数为12-15的取代或未取代的杂芳基；Alternatively, Ar is selected from a substituted or unsubstituted aryl group with 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group with 12 to 15 carbon atoms;可选地，Ar中的取代基各自独立地选自氘、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氘代烷基、碳原子数为6-10的芳基、碳原子数为5-12的杂芳基。Optionally, the substituents in Ar are each independently selected from deuterium, cyano group, alkyl group having 1-4 carbon atoms, deuterated alkyl group having 1-4 carbon atoms, and 6-10 carbon atoms. Aryl groups and heteroaryl groups with 5-12 carbon atoms.
- 根据权利要求1所述的含氮化合物，其中，Ar选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的三联苯基、取代或未取代的吡啶基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基；The nitrogen-containing compound according to claim 1, wherein Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted of carbazolyl;可选地，Ar中的取代基各自独立地选自氘、氰基、甲基、乙基、异丙基、叔丁基、三氘代甲基、苯基、萘基、吡啶基、二苯并呋喃基、二苯并噻吩基或咔唑基。Alternatively, the substituents in Ar are each independently selected from deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, pyridyl, diphenyl furanyl, dibenzothienyl or carbazolyl.
- 根据权利要求1所述的含氮化合物，其中，Ar选自以下基团所组成的组：
The nitrogen-containing compound according to claim 1, wherein Ar is selected from the group consisting of the following groups:
- 根据权利要求1所述的含氮化合物，其中，所述含氮化合物选自以下化合物所组成的组：
The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of the following compounds:
- 电子元件，包括阳极、阴极，以及设置在所述阳极和阴极之间的功能层，所述功能层包含权利要求1-10中任一项所述的含氮化合物。An electronic component includes an anode, a cathode, and a functional layer disposed between the anode and the cathode, the functional layer containing the nitrogen-containing compound according to any one of claims 1-10.
- 根据权利要求11所述的电子元件，其中，所述功能层包括空穴传输层，所述空穴传输层包含所述含氮化合物；The electronic component according to claim 11, wherein the functional layer includes a hole transport layer, and the hole transport layer contains the nitrogen-containing compound;可选地，所述电子元件为有机电致发光器件或光电转化器件。Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.
- 电子装置，包括权利要求11或12所述的电子元件。 An electronic device including the electronic component according to claim 11 or 12.
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