CN112300055A - Nitrogen-containing compound, electronic component, and electronic device - Google Patents
Nitrogen-containing compound, electronic component, and electronic device Download PDFInfo
- Publication number
- CN112300055A CN112300055A CN202011173737.5A CN202011173737A CN112300055A CN 112300055 A CN112300055 A CN 112300055A CN 202011173737 A CN202011173737 A CN 202011173737A CN 112300055 A CN112300055 A CN 112300055A
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- China
- Prior art keywords
- group
- carbon atoms
- substituted
- unsubstituted
- nitrogen
- Prior art date
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 99
- 239000000126 substance Substances 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 152
- 239000010410 layer Substances 0.000 claims description 127
- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 238000002347 injection Methods 0.000 claims description 34
- 239000007924 injection Substances 0.000 claims description 34
- 230000005525 hole transport Effects 0.000 claims description 33
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 30
- 239000002346 layers by function Substances 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 23
- 229910052805 deuterium Inorganic materials 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 239000004305 biphenyl Substances 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 235000010290 biphenyl Nutrition 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000005561 phenanthryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 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 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 37
- 239000011368 organic material Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 41
- 239000000463 material Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
- 239000000543 intermediate Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229940127271 compound 49 Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000021615 conjugation Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- GIMVCZMZRZGDTL-UHFFFAOYSA-N 1-bromo-3-chloro-2-iodobenzene Chemical compound ClC1=CC=CC(Br)=C1I GIMVCZMZRZGDTL-UHFFFAOYSA-N 0.000 description 2
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 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
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 1
- 101100233050 Caenorhabditis elegans ima-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229940126049 IMC-1 Drugs 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
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 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
- SPOHBRIBTFAVAK-UHFFFAOYSA-N [2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxymethyl benzoate Chemical compound CC1=C(CC(=O)OCOC(=O)C=2C=CC=CC=2)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 SPOHBRIBTFAVAK-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 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
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 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
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000011056 performance test Methods 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 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
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The application provides a nitrogen-containing compound shown as chemical formula 1, an electronic element and an electronic device, and belongs to the technical field of organic materials. In the nitrogen-containing compound represented by the chemical formula 1, R1To R8The same or different, and at least two groups selected from the group represented by chemical formula 2. The nitrogen-containing compound can improve the performance of electronic elements, and particularly can improve the performance of organic electroluminescent devices and photoelectric conversion devices.
Description
Technical Field
The present disclosure relates to the field of organic materials, and more particularly, to a nitrogen-containing compound, an electronic component, and an electronic device.
Background
With the development of electronic technology and the advancement of material science, the application range of electronic elements for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components, such as organic electroluminescent devices or photoelectric conversion devices, generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic element is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the organic light emitting layer under the action of the electric field, holes on the anode side also move to the light emitting layer, the electrons and the holes are combined in the organic light emitting layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the organic light emitting layer emits light outwards.
Although there are some organic materials that can be used to transport holes, there is still a need to develop new materials to further improve the performance of electronic components.
The above information disclosed in this background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art. The above information disclosed in this background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art.
Disclosure of Invention
An object of the present application is to provide a nitrogen-containing compound, an electronic component, and an electronic device, in order to improve the performance of the electronic component.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
according to a first aspect of the present application, there is provided a nitrogen-containing compound having a structure represented by chemical formula 1:
R1to R7The same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, and group shown in chemical formula 2; r1To R7At least one group selected from the group represented by chemical formula 2;
R8selected from deuterium, a halogen group, a cyano group, a heteroaryl group with 3-18 carbon atoms, an aryl group with 6-18 carbon atoms, a halogenated aryl group with 6-20 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, an arylsilyl group with 8-12 carbon atoms, an alkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms of a halogenated alkyl group with 1-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms or a group shown in chemical formula 2;
n is R8The number of (a) is selected from 0, 1,2, 3,4, 5; when n is>1, any two R8The same or different;
Ar3is selected from substituted or unsubstituted aryl with 6-12 carbon atoms;
each L, L1、L2The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 6-30 carbon atoms;
each Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 6-24 carbon atoms;
wherein R is1～R8At least 2 of them are selected from the structures shown in formula 2; when chemical formula 1 includes a plurality of groups represented by chemical formula 2, any two of L are the same or different, and any two of L are1Identical or different, any two L2Identical or different, any two Ar1Identical or different, any two Ar2The same or different.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, there is provided an electronic device including the above electronic component.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
The reference numerals of the main elements in the figures are explained as follows:
100. an anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. an electron blocking layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. One skilled in the relevant art will recognize, however, that the subject matter of the present application can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring major technical ideas of the application.
The terms "comprising" and "having" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.
In the context of the present application, it is,
refers to a position bonded to other substituents or bonding positions.
In this application, the number of carbon atoms of a group refers to all the number of carbon atoms. For example, in a substituted arylene group having 10 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 10. Illustratively, the 9, 9-dimethylfluorenyl group is a substituted aryl group having 15 carbon atoms.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, Se, Si, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
The descriptions used in this application that "… … independently" and "… … independently" and "… … independently selected from" are interchangeable and should be understood in a broad sense to mean that the particular items expressed between the same symbols do not interfere with each other in different groups or that the particular items expressed between the same symbols do not interfere with each other in the same groups. For example: in "
Wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from the group consisting of hydrogen, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means either no substituent or substituted with one or more substituents. Such substituents include, but are not limited to, deuterium, halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, silyl, alkylamino, cycloalkyl, heterocyclyl.
In this application, "optional" or "optionally" means that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, two substituents attached to the same atom are linked to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atom to which they are commonly attached" means: when two substituents are bonded to the same atom, the two substituents may be present independently of each other or may be bonded to each other so as to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atoms to which they are bonded together.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. The alkyl group can also be a medium size alkyl group having 1 to 10 carbon atoms. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. In still other embodiments, the alkyl group contains 1 to 5 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH)3) Ethyl group (Et, -CH)2CH3) N-propyl (n-Pr, -CH)2CH2CH3) Isopropyl group (i-Pr, -CH (CH)3)2) N-butyl (n-Bu, -CH)2CH2CH2CH3) Isobutyl (i-Bu, -CH)2CH(CH3)2) Sec-butyl (s-Bu, -CH (CH)3)CH2CH3) Tert-butyl (t-Bu, -C (CH)3)3) And the like. Further, the alkyl group may be substituted or unsubstituted.
In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups may have 3-20 carbon atoms, a numerical range such as "3 to 20" refers to each integer in the given range; for example, "3 to 20 carbon atoms" refers to a cycloalkyl group that can contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The cycloalkyl group may be a small ring, a normal ring or a large ring having 3 to 20 carbon atoms. Cycloalkyl groups can also be divided into monocyclic-only one ring, bicyclic-two rings-or polycyclic-three or more rings. Cycloalkyl groups can also be divided into spiro rings, fused rings, and bridged rings, in which two rings share a common carbon atom, and more than two rings share a common carbon atom. In addition, cycloalkyl groups may be substituted or unsubstituted. In some embodiments cycloalkyl is 5 to 10 membered cycloalkyl, in other embodiments cycloalkyl is 5 to 8 membered cycloalkyl, examples of which may be, but are not limited to: five-membered cycloalkyl, i.e., cyclopentyl, six-membered cycloalkylcyclohexylalkyl, 10-membered polycycloalkyl such as adamantyl, and the like.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
and the like. The "aryl" groups of the present application may contain6-30 carbon atoms, and in some embodiments the number of carbon atoms in the aryl group can be 6-25, in other embodiments the number of carbon atoms in the aryl group can be 6-18, and in other embodiments the number of carbon atoms in the aryl group can be 6-13. For example, in the present application, the number of carbon atoms of the aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30, 31, 32, 33, 34, 35, 36 or 40, and of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.
In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18.
In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracenyl, phenanthrenyl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorenyl, and the like.
In the present application, the fluorenyl group may be substituted and two substituents may be combined with each other to form a spiro structure, specific examples including, but not limited to, the following structures:
in the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The term "heteroaryl" as used herein may contain from 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 3 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 12 to 20. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, N-phenylcarbazolyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
In the present application, specific examples of the heteroaryl group as the substituent include, but are not limited to: dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthrolinyl, and the like.
In this application, the explanation for aryl applies to arylene, the explanation for heteroaryl applies equally to heteroarylene, the explanation for alkyl applies to alkylene, and the explanation for cycloalkyl applies to cycloalkylene.
In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 6-to 10-membered aromatic ring means a benzene ring, an indene ring, a naphthalene ring and the like.
The "ring" in the present application includes saturated rings, unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl, unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, and 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.
In the present application, specific examples of triaryl silicon groups having 18 to 24 carbon atoms include, but are not limited to: triphenylsilyl, and the like.
In the present application, specific examples of the cycloalkyl group having 3 to 20 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
An delocalized bond in the present application refers to a single bond extending from a ring system
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule. For example, as shown in the following formula (X), naphthyl represented by the formula (X) is connected to other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (X-1) to the formula (X-10) includes any possible connecting mode shown in the formula (X-1).
For example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is bonded to the rest of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in the formulas (X '-1) to (X' -4).
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, in the following formula (Y), the substituent R group represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes shown by the formulas (Y-1) to (Y-7).
The application provides a nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
R1to R7The same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, and group shown in chemical formula 2; r1To R7At least one group selected from the group represented by chemical formula 2;
R8selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or a group represented by chemical formula 2;
n is R8The number of (a) is selected from 0, 1,2, 3,4, 5; when n is>1, any two R8The same or different;
Ar3is selected from substituted or unsubstituted aryl with 6-12 carbon atoms;
each L, L1、L2The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 6-30 carbon atoms;
each Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted aryl with 6-24 carbon atomsA substituted heteroaryl group;
wherein R is1～R8At least 2 of them are selected from the structures shown in formula 2; when chemical formula 1 includes a plurality of groups represented by chemical formula 2, any two of L are the same or different, and any two of L are1Identical or different, any two L2Identical or different, any two Ar1Identical or different, any two Ar2The same or different.
In the nitrogen-containing compound provided by the application, a triarylamine structure is connected to an N-phenyl-4-arylcarbazole parent nucleus in a conjugated manner. The carbazolyl and the triarylamine group both have good hole transport capability, and the hole transport capability can be further enhanced after the carbazolyl and the triarylamine group are connected in a conjugated manner. The phenyl group connected with N on the N-phenyl-4-arylcarbazole mother nucleus and the aryl group at the 4-position can further enlarge the conjugated plane of the nitrogen-containing compound and strengthen the conjugated system thereof, and the electron cloud density on the nitrogen-containing compound is improved so as to improve the hole transmission capability thereof. Furthermore, in the N-phenyl-4-arylcarbazole core, the phenyl group attached to N is sterically competitive with the hydrogen or substituent at position 1/8 of carbazole, and the aryl group at position 4 is sterically competitive with the hydrogen or substituent at position 5 of carbazole; the planes of the phenyl connected to N and the aryl at the 4-position are deviated from the plane of carbazole, so that the conjugation degree of the nitrogen-containing compound can be adjusted to realize the adjustment of the HOMO (highest occupied molecular orbital) energy level, the HOMO energy level of the nitrogen-containing compound can be better matched with an electron blocking layer or an organic light-emitting layer, and the efficiency of injecting holes into the organic light-emitting layer is further improved. In addition, the planes of the phenyl on N and the aryl at the 4-position are deviated from the plane of carbazole, so that the asymmetry of the nitrogen-containing compound can be improved, the pi-pi stacking effect of the nitrogen-containing compound can be reduced, the film forming property of the nitrogen-containing compound can be improved, and the thermal stability of an electronic element using the nitrogen-containing compound can be improved.
Alternatively, R1To R7The same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexylCyclopentyl, adamantyl, norbornyl, or the group of formula 2.
Alternatively, R8Selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, naphthyl, biphenyl, fluorenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or a group of formula 2.
In this application, R1To R4At most one group selected from the group represented by chemical formula 2, R5To R7At most one group selected from the group represented by chemical formula 2, when n>At 1 time, each R8At most one group selected from the group represented by chemical formula 2.
In this application, R1To R8In total, 2 or 3 groups are represented by chemical formula 2, and the remainder are hydrogen.
In one embodiment of the present application, R1To R8Are the same or different and are each independently selected from hydrogen or a group represented by chemical formula 2.
In the present application, the nitrogen-containing compound is selected from compounds represented by the following chemical formula:
preferably, Ar is3Selected from phenyl, naphthyl and biphenyl.
In one embodiment of the present application, L, L1、L2The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene group with 6-15 carbon atoms, and substituted or unsubstituted heteroarylene group with 12-20 carbon atoms.
In another embodiment of the present application, L, L1、L2The same or different, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted phenylene groupDibenzothiophenyl, substituted or unsubstituted dimethylfluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolylidene.
Optionally, said L, L1、L2The substituents are the same or different and are independently selected from deuterium, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
Specifically, the L, L1And L2Substituents of (a) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, and the like.
In one embodiment of the present application, L, L1、L2The same or different, and each is independently selected from a single bond or substituted or unsubstituted W: unsubstituted W is selected from the group consisting of:
wherein,
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl; when the number of substituents of the group W is more than 1, the substituents may be the same or different.
Alternatively, L, L1、L2The same or different, and each is independently selected from the group consisting of a single bond or the following substituents:
in the application of this applicationIn the embodiment, Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-20 carbon atoms.
Optionally, the Ar is1And Ar2The substituents of (a) are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.
Specifically, Ar is1And Ar2Substituents of (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, N-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, and the like.
Preferably, Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-15 carbon atoms and substituted or unsubstituted heteroaryl with 12-18 carbon atoms.
In another embodiment of the present application, Ar1And Ar2Identical or different and each is independently selected from the group consisting of substituted or unsubstituted V: unsubstituted V is selected from the group consisting of:
wherein,
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen groups, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl; when the number of substituents of the group V is more than 1, the substituents may be the same or different.
Alternatively, Ar1And Ar2Is the same or differentAnd each independently selected from the group consisting of:
in some embodiments, the chemical formula 2
The groups shown are selected from the group consisting of:
preferably, the nitrogen-containing compound is selected from the group consisting of:
the application also provides an electronic element, which comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
The nitrogen-containing compounds provided herein can be used to form at least one organic film layer in a functional layer to improve voltage characteristics, efficiency characteristics, or lifetime characteristics of an electronic component. Optionally, an organic film layer containing a nitrogen-containing compound of the present application is positioned between the anode and the energy conversion layer of the electronic component to improve the transport of holes between the anode and the energy conversion layer. Further, the functional layer comprises a hole transport layer, and the hole transport layer comprises the nitrogen-containing compound of the present application; or the functional layer comprises a hole injection layer, and the hole injection layer comprises the nitrogen-containing compound of the present application; or the functional layer comprises a hole transport layer and a hole injection layer, and the hole transport layer and the hole injection layer both contain the nitrogen-containing compound of the present application.
The electronic element of the present application may be, for example, an organic electroluminescent device or a photoelectric conversion device. For an organic electroluminescent device, its functional layers may include an organic light-emitting layer as an energy conversion layer; for a photoelectric conversion device, the functional layer may include a photoelectric conversion layer as an energy conversion layer.
According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device may be, for example, a red organic electroluminescent device, a blue organic electroluminescent device, a green organic electroluminescent device, a yellow organic electroluminescent device, a white organic electroluminescent device, or an organic electroluminescent device of other colors.
As shown in fig. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises a nitrogen-containing compound as provided herein.
Alternatively, the functional layer 300 includes a hole injection layer 310, and the hole injection layer 310 is disposed on a surface of the anode 100 near the organic light emitting layer 330.
Alternatively, the functional layer 300 includes a hole transport layer 321, and the hole transport layer 321 is disposed between the organic light emitting layer 330 and the anode 100. Further, when the functional layer 300 includes the hole transport layer 321 and the hole injection layer 310, the hole injection layer 310 is interposed between the hole transport layer 321 and the anode 100.
In a specific embodiment, the hole injection layer 310 comprises a nitrogen-containing compound as provided herein. Preferably, the hole injection layer 310 includes a hole injection host material and the nitrogen-containing compound of the present application as a hole injection adjusting material. Further, in the hole injection layer 310, the amount of the hole injection host material is larger than the nitrogen-containing compound of the present application. In one embodiment of the present application, the hole injection host material is F4-TCNQ.
In a specific embodiment, the hole transport layer 321 includes the nitrogen-containing compound provided herein to improve the hole transport capability of the organic electroluminescent device, thereby improving the light emitting efficiency of the organic electroluminescent device and reducing the driving voltage of the organic electroluminescent device. Alternatively, the hole transport layer 321 may be composed of the nitrogen-containing compound of the present application.
Optionally, the anode 100 comprises an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably comprising a transparent electrode comprising Indium Tin Oxide (ITO) as anode.
Alternatively, 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. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, and the exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. In one embodiment of the present application, the host material of the organic light emitting layer 330 may be BH-01.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be BD-01.
Optionally, cathode 200 includes a cathode material that is a cathode material with small outgassing that facilitates electron injection into the functional layerA material of work. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2But not limited thereto,/Ca. Preferably, a metal electrode comprising an Mg-Ag alloy is included as a cathode.
Alternatively, as shown in fig. 1, an electron transport layer 340 may be further disposed between the cathode 200 and the organic light emitting layer 330. The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, in one embodiment of the present application, the electron transport layer 340 may be composed of ET-06 and LiQ.
Optionally, as shown in fig. 1, an electron blocking layer 322 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability of injecting holes into the organic light emitting layer 330. The electron blocking layer 322 may be selected from benzidine derivatives, triarylamine compounds, or other materials, which are not particularly limited in this application. In one embodiment of the present application, the electron blocking layer 322 may be composed of EB-01.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed 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 material. In one embodiment of the present application, the electron injection layer 350 may include Yb.
According to another embodiment, the electronic component may be a photoelectric conversion device, which may include an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200, as shown in fig. 3; the functional layer 300 comprises a nitrogen-containing compound as provided herein. Among them, the functional layer includes a photoelectric conversion layer 360 as an energy conversion layer.
Alternatively, the nitrogen-containing compound provided herein may be used to form at least one organic thin layer in the functional layer 300 to improve the photoelectric conversion device performance, in particular, to increase the open circuit voltage of the photoelectric conversion device or to increase the photoelectric conversion efficiency of the photoelectric conversion device.
Alternatively, the functional layer 300 includes a hole transport layer 321, and the hole transport layer 321 includes the nitrogen-containing compound of the present application. The hole transport layer 321 may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.
Alternatively, the functional layer 300 includes a hole injection layer containing the nitrogen-containing compound of the present application.
In one embodiment of the present application, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 321, a photoelectric conversion layer 360 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, the solar cell includes an anode 100, a hole transport layer 321, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked, wherein the hole transport layer 321 contains the nitrogen-containing compound of the present application.
In another embodiment of the present application, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole injection layer (not shown in fig. 3), a hole transport layer 321, a photoelectric conversion layer 360 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. Wherein the hole injection layer contains the nitrogen-containing compound of the present application.
The application also provides an electronic device which comprises the electronic element.
According to one embodiment, as shown in fig. 2, the electronic device provided by the present application is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The electronic device may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device has the organic electroluminescent device, the electronic device has the same beneficial effects, and the details are not repeated.
According to another embodiment, as shown in fig. 4, the electronic device provided by the present application is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The electronic device may be, for example, a solar power generation device, a light detector, a fingerprint recognition device, a light module, a CCD camera, or another type of electronic device. Since the electronic device has the photoelectric conversion device, the electronic device has the same beneficial effects, and the details are not repeated herein.
Hereinafter, the present application will be described in further detail with reference to examples. However, the following examples are merely illustrative of the present application and do not limit the present application.
And (3) synthesis of an intermediate:
to a dry nitrogen-purged round-bottom flask, 1-bromo-2-iodo-3-chlorobenzene (50.0g,157.5mmol), phenylboronic acid (19.2g,157.5mmol), tetrakis (triphenylphosphine) palladium (9.1g,7.8mmol), tetrabutylammonium bromide (2.5g,7.8mmol), potassium carbonate (65.2g,472.6mmol), toluene (400mL), ethanol (200mL), deionized water (100mL) were added, and the mixture was heated to 75 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain SM-D (35.8g, yield 85%).
To a dried nitrogen-substituted round-bottomed flask, SM-D (35.8g,133.8mmol) and tetrahydrofuran (400mL) were added, the temperature was reduced to-78 ℃ and n-butyllithium (12.8g,200.7mmol) was added dropwise, after the addition, the temperature was maintained at-78 ℃ for 30min, trimethyl borate (41.7g,401.4mmol) was added dropwise, and after the addition, the temperature was maintained at-78 ℃ for 30 min. Heating to room temperature, stirring for 12h, and adding hydrochloric acid aqueous solution to adjust pH to neutral. The resulting reaction was filtered to give a crude product, which was recrystallized from n-heptane (600mL) to give SM-D-1(19.6g, 63% yield).
Referring to the synthesis method of intermediate SM-D, the intermediates shown in table 1 below were synthesized by substituting reactant Q in table 1 below for phenylboronic acid:
table 1: synthesis of partial intermediates
Referring to the synthesis method of intermediate SM-D, the intermediates shown in table 2 below were synthesized by substituting reactant N for 1-bromo-2-iodo-3-chlorobenzene and reactant M for phenylboronic acid in table 2 below:
table 2: synthesis of partial intermediates
Referring to the synthesis of intermediate SM-D-1, the intermediates shown in table 3 below were synthesized as (reactant) intermediates instead of SM-D:
table 3: synthesis of partial intermediates
To a dry and nitrogen-purged round-bottom flask, SM-D-1(5.0g,26.0mmol),2, 4-dichloronitrobenzene (6.1g,26.0mmol), tetrakis (triphenylphosphine) palladium (0.6g, 0.5mmol), tetrabutylammonium bromide (0.4g, 1.3mmol), potassium carbonate (10.8g, 78.1mmol), toluene (40mL), ethanol (20mL), deionized water (10mL) were added, and the mixture was heated to 78 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain IM-A-1(6.3 g; yield 70%).
To a dry nitrogen-purged round-bottom flask, IMA-1(5.0g 14.5mmol), triphenylphosphine (9.5g 36.3mmol) and o-dichlorobenzene (40mL) were added, and the mixture was heated to 160 ℃ with stirring to react for 6 hours; and then silica gel was added thereto to volatilize the liquid therein, followed by silica gel column chromatography purification using methylene chloride/n-heptane (1:3) as a mobile phase to give IMB-1(2.7g, yield 60%).
Adding IM-B-1(5.0g,16.0mmol), iodobenzene (3.3g,16.3mmol), cuprous iodide (0.61g,3.2mmol), potassium carbonate (4.9g,35.2mmol), 1, 10-phenanthroline (1.2g,6.4mmol), 18-crown ether-6 (0.4g,1.6mmol), N, N, -dimethylformamide (50mL) into a dried and nitrogen-replaced round-bottom flask, and heating to 160 ℃ under a stirring condition for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain IM-C-1(4.9g, yield 80%).
Referring to the synthesis of IM-A-1, in Table 4 below, starting material A was used instead of 2, 4-dichloronitrobenzene and SM-X was used instead of SM-D-1. Intermediates shown in table 4 below were synthesized:
table 4: synthesis of partial intermediates
Referring to the synthesis of IM-B-1, the intermediates shown in Table 5 below were synthesized by substituting raw material B in Table 5 below for IM-A-1:
table 5: synthesis of partial intermediates
Referring to the synthesis of IM-C-1, the intermediates shown in Table 6 below were synthesized by substituting IM-B-1 with starting material C in Table 6 below:
table 6: synthesis of partial intermediates
To a dry nitrogen-purged round-bottom flask, p-chlorobenzeneboronic acid (4.0g,25.7mmol), IM-C-1(5.0g,12.9mmol), tetrakis (triphenylphosphine) palladium (0.3g, 0.3mmol), tetrabutylammonium bromide (0.18g,0.6mmol), potassium carbonate (5.3g,38.6mmol), toluene (40mL), ethanol (20mL), deionized water (10mL) were added, and the temperature was raised to 75 ℃ with stirring and maintained for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (100mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the crude product obtained was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to give IM-D-1(5.6g, yield 80%).
Referring to the synthesis method of IM-D-1, the intermediates in Table 7 below were synthesized by substituting IM-C-1 with raw material D and p-chlorobenzeneboronic acid with SM-D in Table 7 below:
table 7: synthesis of partial intermediates
To a dry and nitrogen-purged round-bottom flask, biphenyl-2-boronic acid (51.6g,260.4mmol), 2, 4-dichloronitrobenzene (50.0g,260.4mmol), tetrakis (triphenylphosphine) palladium (15.0g,13.0mmol), tetrabutylammonium bromide (4.2g,13.0mmol), potassium carbonate (107.9g,781.3mmol), toluene (400mL), ethanol (200mL), deionized water (100mL) were added, and the mixture was heated to 75 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to give IM-O-1(56.5 g; yield 70%).
To a dry nitrogen-purged round-bottomed flask, IM-O-1(56.5g,182.4mmol), triphenylphosphine (119.6g,456.0mmol) and O-dichlorobenzene (400mL) were added, and the mixture was heated to 160 ℃ with stirring and reacted for 6 hours; then, silica gel was added thereto to volatilize the liquid therein, followed by silica gel column chromatography purification using methylene chloride/n-heptane (1:3) as a mobile phase to obtain IM-P-1(30.4g, yield 60%).
Adding IM-P-1(5.0g,17.9mmol), P-iodochlorobenzene (4.4g,18.3mmol), cuprous iodide (0.7g,3.6mmol), potassium carbonate (5.5g,39.6mmol), 1, 10-phenanthroline (1.3g,7.2mmol), 18-crown ether-6 (0.5g,1.8mmol), N, N, -dimethylformamide (30mL) into a dried and nitrogen-replaced round-bottom flask, and heating to 160 ℃ under a stirring condition for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain IM-Q-1(5.2g, yield 75%).
The intermediates of Table 8 below were synthesized by the same method as that of IM-O-1, substituting O for 2, 4-dichloronitrobenzene and SM-M for biphenyl-2-boronic acid in Table 8 below:
table 8: synthesis of partial intermediates
Referring to the same procedure as IM-P-1, the intermediates shown in Table 9 below were synthesized by substituting the starting material P in Table 9 for IM-O-1:
table 9: synthesis of partial intermediates
Referring to the synthesis method of IM-Q-1, the intermediate shown in Table 10 below was synthesized by substituting IM-P-1 with Q as a raw material and P-chloroiodobenzene with N as a raw material in Table 10 below:
table 10: synthesis of partial intermediates
A reaction flask was charged with IMC-1(5.0g, 12.9mmol), SM-1 (diphenylamine) (4.4g, 25.8mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.25mmol), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.21g, 0.5mmol), sodium tert-butoxide (4.9g, 51.6mmol) and toluene solvent (50mL), heated to 110 ℃ under nitrogen protection, heated under reflux and stirred for 8 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed with dichloromethane (50mL) and water (50mL) 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtering, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system (1:3) to obtain 49(6.3g, 75%).
Referring to the synthesis of compound 49, in Table 11 below SM-Y is substituted for SM-1 (diphenylamine) and IM-X is substituted for IM-C-1. The compounds shown in table 11 below were synthesized:
table 11: synthesis of partial Compound
Mass spectrometry analysis of the above synthesized compounds yielded mass spectrometry data for each compound as shown in table 12 below:
table 12: mass spectral data of partial compounds
| Compound numbering | Mass spectrum [ M + H]+ | Compound numbering | Mass spectrum [ M + H]+ |
| Compound 49 | 654.3 | Compound 178 | 906.4 |
| Compound 47 | 654.3 | Compound 113 | 654.3 |
| Compound 26 | 654.3 | Compound 175 | 834.3 |
| Compound 146 | 806.3 | Compound 176 | 886.4 |
| Compound 147 | 958.4 | Compound 179 | 1115.4 |
| Compound 148 | 820.3 | Compound 180 | 1109.4 |
| Compound 149 | 730.3 | Compound 199 | 682.3 |
| Compound 150 | 754.3 | |
766.4 |
| Compound 151 | 958.4 | Compound 201 | 674.4 |
| Compound 173 | 958.4 | Compound 202 | 922.4 |
| Compound 174 | 806.3 | Compound 203 | 704.3 |
| Compound 177 | 920.4 |
Nuclear magnetic analysis of the partially synthesized compounds above gave the following nuclear magnetic data for each compound as shown in table 13 below:
table 13: mass spectral data of partial compounds
Preparation and evaluation of organic electroluminescent device
Example 1: preparation of blue organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
Compound 49 and F4-TCNQ were applied to an experimental substrate (anode) at 97%: 3% by mass of the above components was co-evaporated to a thickness of
And a compound is vapor-deposited on the Hole Injection Layer (HIL)49 to a thickness of
A Hole Transport Layer (HTL).
Vacuum evaporating EB-01 on the hole transport layer to form a layer with a thickness of
The electron blocking layer of (1).
On the electron blocking layer, BH-01 and BD-01 were mixed in a ratio of 98%: 2% by mass ratio, and forming a film having a thickness of
Blue light emitting layer (EML).
ET-06 and LiQ were formed by vapor deposition at a film thickness ratio of 1:1
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is formed on the electron injection layer to a thickness of
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 23
An organic electroluminescent device was fabricated by the same method as example 1, except that compounds shown in the column (HIL/HTL) in table 14 below were used instead of compound 49 in forming the hole injection layer/hole transport layer.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that in the formation of the hole injection layer/hole transport layer, the compound a-1 was used instead of the compound 49.
Comparative example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound a-2 was used instead of the compound 49 in forming the hole injection layer/hole transport layer.
Comparative example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound a-3 was used instead of the compound 49 in forming the hole injection layer/hole transport layer.
The structures of the materials used in the above examples and comparative examples are as follows:
for the organic electroluminescent device prepared as above, at 20mA/cm2Formation tests were performed under the conditions of (1), and the test results are shown in table 14.
Table 14: performance test results of organic electroluminescent device
From the results in table 14, it is understood that in examples 1 to 23, which are examples of the compound for the hole injection layer/hole transport layer, the luminous efficiency (Cd/a) of the above-mentioned organic electroluminescent device prepared by using the compound used in the present application as the hole injection layer/hole transport layer is improved by at least 13.51%, the external quantum efficiency EQE (%) is improved by at least 13.49%, and the lifetime is improved by at least 6.80%, compared with comparative examples 1 to 4, which are examples of devices corresponding to known compounds.
It should be understood that this application is not intended to limit the application to the details of construction and the arrangement of components set forth in the specification. The application is capable of other embodiments and of being practiced and carried out in various ways. The foregoing variations and modifications are within the scope of the present application. It will be understood that the application disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the text and/or drawings. All of these different combinations constitute a number of alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known for carrying out the application and will enable those skilled in the art to make and use the application.
Claims (12)
1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
R1to R7The same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, and group shown in chemical formula 2;
R8selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or a group represented by chemical formula 2;
n is R8The number of (a) is selected from 0, 1,2, 3,4, 5; when n is>At 1 hourAny two R8The same or different;
Ar3selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;
each L, L1、L2The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 6-30 carbon atoms;
each Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 6-24 carbon atoms;
wherein R is1～R8At least 2 of them are selected from the structures shown in formula 2; when chemical formula 1 includes a plurality of groups represented by chemical formula 2, any two of L are the same or different, and any two of L are1Identical or different, any two L2Identical or different, any two Ar1Identical or different, any two Ar2The same or different;
each L, L1、L2、Ar1And Ar2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms and a phosphinyloxy group having 6 to 18 carbon atoms;
Ar3wherein the substituent is selected from deuterium, halogen group, cyano group, C1-5 alkyl group, phenyl group.
2. The nitrogen-containing compound according to claim 1, wherein Ar is Ar3Selected from phenyl, naphthyl and biphenyl.
3. The nitrogen-containing compound of claim 1, wherein R is1To R4At most one group selected from the group represented by chemical formula 2, R5To R7At most one group selected from the group represented by chemical formula 2, each R8At most one of them is a group represented by chemical formula 2.
4. The nitrogen-containing compound of claim 1, wherein L, L1、L2The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-15 carbon atoms, substituted or unsubstituted heteroarylene with 12-20 carbon atoms;
preferably, said L, L1、L2The substituents are the same or different and are independently selected from deuterium, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
5. The nitrogen-containing compound of claim 1, wherein L, L1、L2The same or different, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl subunit;
preferably, said L, L1And L2The substituents of (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl.
6. The nitrogen-containing compound of claim 1, wherein each L, L1、L2The same or different, and each is independently selected from a single bond or substituted or unsubstituted W: unsubstituted W is selected from the group consisting of:
wherein,
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl; when the number of substituents of the group W is more than 1, the substituents may be the same or different.
7. The nitrogen-containing compound according to claim 1, wherein each Ar is Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-20 carbon atoms;
preferably, Ar is1And Ar2The substituents of (a) are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.
8. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Identical or different and each is independently selected from the group consisting of substituted or unsubstituted V: unsubstituted V is selected from the group consisting of:
wherein,
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen groups, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl; when the number of substituents of the group V is more than 1, the substituents may be the same or different.
9. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
10. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode;
the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 9;
preferably, the functional layer comprises a hole injection layer comprising the nitrogen-containing compound;
preferably, the functional layer comprises a hole transport layer comprising the nitrogen-containing compound.
11. The electronic component according to claim 10, wherein the electronic component is an organic electroluminescent device or a solar cell.
12. An electronic device, characterized by comprising the electronic component of claim 10 or 11.
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| CN113582909A (en) * | 2021-07-30 | 2021-11-02 | 上海钥熠电子科技有限公司 | Large steric hindrance carbazole compound and application thereof in organic electroluminescent display device |
| CN113773207A (en) * | 2021-06-18 | 2021-12-10 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device comprising same |
| WO2022088865A1 (en) * | 2020-10-28 | 2022-05-05 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, electronic element, and electronic apparatus |
| WO2022206389A1 (en) * | 2021-03-31 | 2022-10-06 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound and electronic element comprising same, and electronic device |
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| Publication number | Publication date |
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| CN112300055B (en) | 2023-02-10 |
| WO2022088865A1 (en) | 2022-05-05 |
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