CN114057705B - Nitrogen-containing compound, and electronic element and electronic device comprising same - Google Patents
Nitrogen-containing compound, and electronic element and electronic device comprising same Download PDFInfo
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- CN114057705B CN114057705B CN202110698599.0A CN202110698599A CN114057705B CN 114057705 B CN114057705 B CN 114057705B CN 202110698599 A CN202110698599 A CN 202110698599A CN 114057705 B CN114057705 B CN 114057705B
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- nitrogen
- carbon atoms
- containing compound
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 92
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 98
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 230000005525 hole transport Effects 0.000 claims description 35
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002346 layers by function Substances 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 description 160
- 125000003118 aryl group Chemical group 0.000 description 57
- 125000001072 heteroaryl group Chemical group 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 32
- 125000000217 alkyl group Chemical group 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 125000004665 trialkylsilyl group Chemical group 0.000 description 16
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
- 239000011737 fluorine Substances 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000004414 alkyl thio group Chemical group 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 10
- 125000000732 arylene group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000005549 heteroarylene group Chemical group 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229910052722 tritium Inorganic materials 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 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 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 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 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 101100233050 Caenorhabditis elegans ima-1 gene Proteins 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- JSVXIWLDFVOHBB-UHFFFAOYSA-N 1-bromo-2-(2-chlorophenyl)benzene Chemical group ClC1=CC=CC=C1C1=CC=CC=C1Br JSVXIWLDFVOHBB-UHFFFAOYSA-N 0.000 description 2
- XDPLWYUXKVCBFV-UHFFFAOYSA-N 1-bromo-3-(3-chlorophenyl)benzene Chemical group ClC1=CC=CC(C=2C=C(Br)C=CC=2)=C1 XDPLWYUXKVCBFV-UHFFFAOYSA-N 0.000 description 2
- HPJCIBVGJBEJPU-UHFFFAOYSA-N 1-fluoro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(F)=CC=C2 HPJCIBVGJBEJPU-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
- WIBSYPXJJKRRRB-UHFFFAOYSA-N 3,6-difluoro-9h-carbazole Chemical compound C1=C(F)C=C2C3=CC(F)=CC=C3NC2=C1 WIBSYPXJJKRRRB-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 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
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 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
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 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
- 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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000002585 base Substances 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
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 238000004891 communication Methods 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence 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
- 230000005283 ground state Effects 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
- 125000002883 imidazolyl group Chemical group 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
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 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
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 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
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—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
- 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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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application belongs to the field of organic luminescent materials, and particularly relates to a nitrogen-containing compound, an electronic element and an electronic device containing the same, wherein the structure of the nitrogen-containing compound is shown as a formula 1, and X is selected from O or S; m is 0, 1 or 2, n is 0, 1 or 2, and 1.ltoreq.m+n.ltoreq.2. The nitrogen-containing compound is used in electronic components, and can improve the performance of the electronic components.
Description
Technical Field
The application belongs to the technical field of organic luminescent materials, and particularly provides a nitrogen-containing compound, and an electronic element and an electronic device containing the nitrogen-containing compound.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. In recent years, organic electroluminescent devices (OLED: organic electroluminescent device) have come into the field of view as a new generation display technology. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of 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. When voltage is applied to the cathode and the anode, the two electrodes generate electric fields, electrons on the cathode side move to the light-emitting layer under the action of the electric fields, electrons on the anode side also move to the light-emitting layer, the two electrodes are combined to form excitons on the light-emitting layer, the excitons are in an excited state to release energy outwards, and the process of releasing energy from the excited state to a ground state emits light outwards. At present, the organic electroluminescent device still has the problem of poor performance, and particularly, how to further improve the service life or efficiency of the device under the condition of ensuring low driving voltage is still a problem to be solved.
Disclosure of Invention
In view of the foregoing problems of the prior art, an object of the present application is to provide a nitrogen-containing compound, which is used in an electronic component and can improve the performance of the electronic component, and an electronic component and an electronic device including the same.
In order to achieve the above object, a first aspect of the present application provides a nitrogen-containing compound having a structure as shown in formula 1:
wherein X is selected from O or S;
ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 and L 2 Identical or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms, and L 1 And L 2 Are not single bonds at the same time;
m is 0, 1 or 2, n is 0, 1 or 2, and 1.ltoreq.m+n.ltoreq.2;
Ar、L、L 1 and L 2 Substituent of (2) and R 1 、R 2 The same or different, each independently selected from: deuterium, tritium, halogen group, cyano group, aryl group having 6 to 18 carbon atoms,Heteroaryl group having 3 to 18 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylthio group having 6 to 18 carbon atoms, triphenylsilyl group;
p 1 R represents 1 And is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when p is 1 When the number is greater than 1, any two R 1 The same or different; optionally, any adjacent two R 1 Forming a ring;
p 2 r represents 2 And is selected from 0, 1, 2, 3 or 4; when p is 2 When the number is greater than 1, any two R 2 The same or different; optionally, any adjacent two R 2 Forming a ring.
A second aspect of the present application provides an electronic component including 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 the first aspect of the present application.
A third aspect of the application provides an electronic device comprising an electronic component according to the second aspect of the application.
The inventor of the application discovers in the research that in the structure formed by substituting triarylamine with N-phenyl carbazole, when one or two F are connected on the carbazolyl, F has strong electron withdrawing capability, and can reduce the electron cloud density on the parent nucleus structure; meanwhile, specific groups such as dibenzofuran group/dibenzothiophene group and the like are introduced into triarylamine, at least one of the two groups of N-phenyl carbazole group and dibenzofuran/dibenzothiophene group is controlled to be connected with N atoms through aromatic groups, so that the torsion degree of the whole molecular structure can be improved, the molecular structure of the compound is improved, the compound provided by the application has higher thermal stability, the electron transmission speed can be effectively reduced, and the electron transmission in the device is blocked. The nitrogen-containing compound can be used as an electron blocking layer material to improve the performance of an OLED device, and especially improve the luminous efficiency and the service life of the device under the condition of ensuring that the device has lower driving voltage.
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 a first 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 a second electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport 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. and a second electronic device.
Detailed Description
The following describes specific embodiments of the present application in detail with reference to the drawings. It should be understood that the detailed description and specific examples, while indicating and illustrating the application, are not intended to limit the application.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula 1:
wherein X is selected from O or S;
ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted arylene group having 3 to 25 carbon atomsAnd L is heteroarylene of 1 And L 2 Are not single bonds at the same time;
m is 0, 1 or 2, n is 0, 1 or 2, and 1.ltoreq.m+n.ltoreq.2;
Ar、L、L 1 and L 2 Substituent of (2) and R 1 、R 2 The same or different, each independently selected from: deuterium, tritium, a halogen group, a cyano group, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 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 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkoxy 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, a triphenylsilyl group;
p 1 r represents 1 And is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when p is 1 When the number is greater than 1, any two R 1 The same or different; optionally, any adjacent two R 1 Forming a ring;
p 2 r represents 2 And is selected from 0, 1, 2, 3 or 4; when p is 2 Above 1, optionally, any two R 2 The same or different; any two adjacent R 2 Forming a ring.
In the present application, the description that "each … … is independently selected from" and "… … is independently selected from" and "… … is independently selected from" may be used interchangeably, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, "Wherein each q is independently selected from 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, and each R ' can be the same or different, and the options of each R ' are thatThe mutual influence is avoided; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on 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 each other.
In the present application, the terms "optional," "optionally," and "optionally" mean 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, any two substituents adjacent x form a ring" means that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. Wherein the above substituents, i.e., rc, may be, for example, deuterium, tritium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, triphenylsilyl, alkyl, haloalkyl, alkenyl, cycloalkyl, alkylthio, alkoxy, and the like; when two substituents Rc are attached to the same atom, the two substituents Rc may be present independently or attached to each other to form a ring with the atom; when two adjacent substituents Rc are present on a functional group, the adjacent substituents Rc may be present independently or fused to the functional group to which they are attached to form a ring.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, a conjugated bond through a carbon-carbon bond A monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, and a condensed ring aryl group connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present application unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. In the present application, biphenyl, terphenyl, and 9, 9-dimethylfluorenyl are all regarded as aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc. In the present application, the arylene group refers to a divalent group formed by further losing one hydrogen atom from the aryl group.
In the present application, the substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium, a halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, or 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 of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, heteroaryl means a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include, but are not limited to, 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, dibenzothiophenyl, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. In the present application, the heteroarylene group refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or two or more hydrogen atoms in the heteroaryl group are substituted with a group such as deuterium, a halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, or the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, "any two adjacent R forms a ring" (R represents R) 1 、R 2 ) In the above, the "any adjacent" may include two R groups on the same atom, and may include two adjacent atoms each having one R group; wherein, when two R's are present on the same atom, the two R's may form a saturated or unsaturated ring with the atom to which they are commonly attached, e.g. form a 5-to 15-membered saturated or unsaturated ringA ring, for example, a cyclopentane, cyclohexane or fluorene ring may be formed; when two adjacent atoms each have one R, the two R's may be fused into a ring, for example, fused to form a benzene ring, naphthalene ring, or the like.
In the present application, the non-positional connection key refers to a single bond extending from the ring system "By "it is meant that one end of the linkage can be attached to any position in the ring system through which the linkage extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
By an off-site substituent in the context of the present application is meant a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by the same includes any one of possible linkages as shown in the formulae (Y-1) to (Y-7).
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 alkyl group having 3 to 10 carbon atoms, and the carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 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, the number of carbon atoms of the aryl group as a substituent is, for example, 6 to 18, 6 to 15, etc., and the number of carbon atoms is, for example, 6, 10, 12, 14, 15, 18, etc., and specific examples of the aryl group include, but are not limited to, phenyl, naphthyl, biphenyl, etc.
In the present application, the heteroaryl group as a substituent has, for example, 3 to 18, 5 to 15, 5 to 12 and the like, and the heteroaryl group has, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 and the like, and specific examples of the heteroaryl group include, but are not limited to, a pyridyl group, a quinolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group and the like.
In the present application, the trialkylsilyl group as a substituent may have 3 to 12 carbon atoms, preferably 3 to 7 carbon atoms, and specific examples thereof include, but are not limited to, trimethylsilyl group, ethyldimethylsilyl group, triethylsilyl group and the like.
In the present application, the number of carbon atoms of the cycloalkyl group as a substituent may be 3 to 10, preferably 5 to 10, and specific examples include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present application, specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
According to one embodiment, the nitrogen-containing compound has a structure as shown in formula 1-1:
according to another embodiment, the nitrogen-containing compound has a structure as shown in formulas 1-2:
and, in addition, the processing unit,
in the formula 1-2, L 2 Selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms.
Alternatively, R 1 、R 2 And are the same or different and are each independently selected from deuterium, fluorine, cyano, aryl having 6 to 15 carbon atoms, heteroaryl having 5 to 12 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkylthio having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, aryloxy having 6 to 12 carbon atoms, arylthio having 6 to 12 carbon atoms.
Further alternatively, R 1 、R 2 And are the same or different and are each independently selected from deuterium, fluorine, cyano, aryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, and cycloalkyl having 5 to 10 carbon atoms. R is R 1 、R 2 Specific examples of (c) include, but are not limited to, deuterium, fluoro, cyano, phenyl, naphthyl, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, cyclopentyl, cyclohexyl, and the like, respectively.
Optionally, the substituents in Ar are selected from: deuterium, tritium, fluorine, cyano, aryl having 6 to 15 carbon atoms, heteroaryl having 3 to 12 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkylthio having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, aryloxy having 6 to 12 carbon atoms, arylthio having 6 to 12 carbon atoms, triphenylsilyl.
Further alternatively, the substituents in Ar are selected from: deuterium, tritium, fluorine, cyano, aryl having 6 to 15 carbon atoms, heteroaryl having 5 to 12 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, and triphenylsilyl. Specific examples of substituents in Ar include, but are not limited to, deuterium, tritium, fluorine, cyano, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, cyclohexyl, cyclopentyl, triphenylsilyl, and the like.
Alternatively, ar is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms. Specifically, ar may be selected from: substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 carbon atoms.
Still alternatively, ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.
In one embodiment, ar is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, and substituted or unsubstituted quinolinyl. Substituents in Ar are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, pyridyl, naphthyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, trifluoromethyl; optionally, any adjacent two substituents form a cyclopentane, cyclohexane or fluorene ring. Ar has the above-mentioned carbon atoms.
In some embodiments, ar is selected from the group consisting of groups represented by formulas i-1 through i-15 below:
wherein,represents a chemical bond, M 1 Selected from single bond or->
G 1 ～G 5 Each independently selected from N or C (F) 1 ) And G 1 ～G 5 At least one of which is selected from N; when G 1 ～G 5 More than two of them are selected from C (F 1 ) At any two times F 1 The same or different;
G 6 ～G 13 each independently selected from N or C (F) 2 ) And G 6 ～G 13 At least one of which is selected from N; when G 6 ～G 13 More than two of them are selected from C (F 2 ) At any two times F 2 The same or different;
G 14 ～G 23 each independently selected from N or C (F) 3 ) And G 14 ～G 23 At least one of which is selected from N; when G 14 ～G 23 More than two of them are selected from C (F 3 ) At any two times F 3 The same or different;
G 24 ～G 33 each independently selected from N or C (F) 4 ) And G 24 ～G 33 At least one of which is selected from N; when G 24 ～G 33 More than two of them are selected from C (F 4 ) When in use, any two are usedF (F) 4 The same or different;
Z 1 selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, triphenylsilyl;
Z 2 ～Z 9 、Z 21 each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, heteroaryl having 3 to 15 carbon atoms;
Z 10 ～Z 20 、F 1 ～F 4 Each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 15 carbon atoms;
h 1 ～h 21 in h k Indicating Z 1 ～Z 21 In Z k K represents a variable, an arbitrary integer of 1 to 21, h k Represents a substituent H k Is the number of (3); wherein when k is selected from 5 or 17, h k Selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k Selected from 1, 2, 3 or 4; when k is selected from 1, 3, 4, 6, 9 or 14, h k Selected from 1, 2, 3, 4 or 5; when k is 13, h k Selected from 1, 2, 3, 4, 5 or 6; when k is selected from 10 or 19, h k Selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k Selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is 11, h k Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k When the number is greater than 1, any two Z k The same or different; optionally, any two adjacent Z k Forming a ring;
K 1 selected from O, S, N (Z) 22 )、C(Z 23 Z 24 )、Si(Z 23 Z 24 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein Z is 22 、Z 23 、Z 24 Each independently selected from: hydrogen, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 15 carbon atoms, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 10 carbon atoms, or Z 23 And Z 24 Are linked to each other to form a saturated or unsaturated ring having 5 to 15 carbon atoms with the atoms to which they are commonly linked;
K 2 selected from single bonds, O, S, N (Z) 25 )、C(Z 26 Z 27 )、Si(Z 26 Z 27 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein Z is 25 、Z 26 、Z 27 Each independently selected from: hydrogen, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 15 carbon atoms, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 10 carbon atoms, or Z 26 And Z 27 Are linked to each other so that the atoms to which they are commonly linked form a saturated or unsaturated ring having 5 to 15 carbon atoms.
In formulas i-13 to i-15, F 2 To F 4 Can be F i I is a variable, and represents 2, 3 or 4. For example, when i is 2, F i Refer to F 2 . It should be appreciated that when the non-locating connection is connected to C (F i ) When in the upper position, C (F i ) F in (F) i Is not present. For example, in chemical formula i-13, when'"connected to G 12 When G 12 The structure which can only represent a C atom, i.e., formula i-13, is specifically: />
In the present application, Z is as described above 23 And Z is 24 Z is as described above 26 And Z is 27 In two groups, eachThe ring formed by the interconnection of two groups in a group may be saturated or unsaturated, for example, a saturated or unsaturated 5-to 15-membered ring may be formed. For example, in formula i-10, when K 2 And M 1 All are single bonds, Z 19 Is hydrogen, h 19 =7, and K 1 Is C (Z) 23 Z 24 ) When Z is 23 And Z is 24 When the atoms which are mutually connected with the two are mutually connected to form a 5-membered ring, the chemical formula i-10 isSimilarly, formula i-10 may also representI.e. H 23 And H is 24 The atoms that are linked to each other so as to be linked together with them form a partially unsaturated 13-membered ring.
Optionally Ar is selected from the group consisting of substituted or unsubstituted radicals V 1 Unsubstituted group V 1 Selected from the group consisting of:
substituted group V 1 Each substituent is independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, fluoroalkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, trialkylsilyl with 3-7 carbon atoms, phenyl, naphthyl, pyridyl and triphenylsilyl; and when the number of the substituents is greater than 1, each substituent is the same or different; optionally, any adjacent two substituents form a ring, for example forming a fluorene ring, cyclohexane or cyclopentane.
Optionally, ar is selected from the group consisting of:
further alternatively, ar is selected from the group consisting of:
in one embodiment, ar isPreferably Ar is->
Optionally L, L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 20 carbon atoms. Specifically L, L 1 And L 2 May each be independently selected from: a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Also optionally, L, L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms.
Optionally L, L 1 And L 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, fluoroalkyl having 1 to 4 carbon atoms, methoxy, trimethylsilyl Triethylsilyl, phenyl.
Further optionally, L, L 1 And L 2 Each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, cyclopentyl, cyclohexyl, trifluoromethyl, trimethylsilyl, phenyl.
In some embodiments, L, L 1 And L 2 Identical or different, each independently selected from a single bond or from a group represented by formulae j-1 to j-13:
wherein M is 2 Selected from single bonds orRepresents a chemical bond;
Q 1 ～Q 5 each independently selected from N or C (J) 5 ) And Q is 1 ～Q 5 At least one of which is selected from N; when Q is 1 ～Q 5 More than two of them are selected from C (J) 5 ) At any two J 5 The same or different;
Q 6 ～Q 13 each independently selected from N or C (J) 6 ) And Q is 6 ～Q 13 At least one of which is selected from N; when Q is 6 ～Q 13 More than two of them are selected from C (J) 6 ) At any two J 6 The same or different;
Q 14 ～Q 23 each independently selected from N or C (J) 7 ) And Q is 14 ～Q 23 At least one of which is selected from N; when Q is 14 ～Q 23 More than two of them are selected from C (J) 7 ) At any two J 7 The same or different;
Q 24 ～Q 32 each independently selected from N or C (J) 8 ) And Q is 24 ～Q 32 At least one of which is selected from N; when Q is 24 ～Q 32 More than two of them are selected from C (J) 8 ) At any two J 8 The same or different;
E 1 ～E 14 、J 5 ～J 9 each independently selected from: hydrogen, deuterium, halogen group, heteroaryl group having 3 to 15 carbon atoms, aryl group having 6 to 15 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 12 carbon atoms, arylthio group having 6 to 12 carbon atoms;
e 1 ～e 14 E is as follows r Representation, E 1 ～E 14 By E r R is a variable, and represents an arbitrary integer of 1 to 14, e r Represents a substituent E r Is the number of (3); when r is selected from 1, 2, 3, 4, 5, 6, 9, 13 or 14, e r Selected from 1, 2, 3 or 4; when r is selected from 7 or 11, e r Selected from 1, 2, 3, 4, 5 or 6; when r is 12, e r Selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, e r Selected from 1, 2, 3, 4, 5, 6, 7 or 8; when e r When greater than 1, any two E r The same or different;
K 3 selected from O, S, se, N (E) 15 )、C(E 16 E 17 )、Si(E 16 E 17 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein E is 15 、E 16 、E 17 Each independently selected from: aryl having 6 to 15 carbon atoms, heteroaryl having 3 to 15 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, or E 16 And E is 17 Are linked to each other to form a saturated or unsaturated ring having 5 to 15 carbon atoms with the atoms to which they are commonly linked;
K 4 selected from single bonds, O, S, se, N (E) 18 )、C(E 19 E 20 )、Si(E 19 E 20 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein E is 18 To E to 20 Each independently selected from: aryl having 6 to 15 carbon atoms, heteroaryl having 3 to 15 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, or E 19 And E is 20 Are linked to each other so that the atoms to which they are commonly linked form a saturated or unsaturated ring having 5 to 15 carbon atoms.
Optionally L, L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted 9, 9-dimethylfluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazole group; wherein each substituent is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl, pyridyl, trifluoromethyl, trimethylsilyl, methoxy, methylthio, cyclohexyl, cyclopentyl. L, L 1 And L 2 The number of carbon atoms of (2) is as indicated above.
In one embodiment, L, L 1 And L 2 Identical or different and are each independently selected from single bonds, substituted or unsubstituted groups V 2 Unsubstituted group V 2 Selected from the group consisting of:
substituted group V 2 Each substituent is independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, fluoroalkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, trialkylsilyl with 3-7 carbon atoms, phenyl and naphthyl; when the number of substituents is greater than 1, each substituent may be the same or different.
Alternatively, L 1 Selected from the group consisting of single bonds and:
alternatively, the process may be carried out in a single-stage,selected from the group consisting of: />
Wherein, represent andis linked to, # denotes and +.>Is a ligation site of (2).
Preferably, the method comprises the steps of,selected from->
Alternatively, L and L 2 Each independently selected from the group consisting of a single bond and:
in one embodiment, the total number of carbon atoms of groups L and Ar is no more than 25, and the total number of carbon atoms of groups L and Ar is preferably 10 to 22. Alternatively, L 2 Is a single bond or phenylene.
Alternatively, the process may be carried out in a single-stage,selected from the group consisting of: />
In the present application,specifically, the compound can be selected from the group consisting of the following structures:
/>
in a preferred embodiment of the present application,selected from->I.e. < ->Selected from the group consisting of:
in the present application,specifically, the group may be selected from the group consisting of:
preferably, m=1, and n=1 or 0, i.eSelected from->
According to a preferred embodiment, the structure of the nitrogen-containing compound is selected from the group represented by formulas 1-a to 1-D:
/>
in this preferred embodiment, the nitrogen-containing compound is applied to an OLED device, which can further increase the lifetime of the device.
Further preferably, the structure of the nitrogen-containing compound is selected from the group consisting of:
Under the condition, the compound has better configuration, three groups on the aromatic amine have higher compatibility, the interaction among the groups can be fully realized, and the performance of the device can be further improved. More preferably, X is O.
Optionally, the nitrogen-containing compound is selected from the group consisting of:
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the method of synthesizing the nitrogen-containing compound provided by the present application is not particularly limited, and a person skilled in the art can determine a suitable synthesis method from the method of preparing the nitrogen-containing compound according to the present application provided in connection with the synthesis example section. In other words, the synthesis examples section of the present application illustratively provides a process for the preparation of nitrogen-containing compounds, using starting materials which are commercially available or are well known in the art. All of the nitrogen-containing compounds provided herein may be obtained by one skilled in the art from these exemplary methods of preparation, and all specific methods of preparation for such nitrogen-containing compounds are not described in detail herein and should not be construed as limiting the application.
A second aspect of the present application provides an electronic component including 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 the first aspect of the present application.
The nitrogen-containing compound provided by the application can be used for forming at least one organic film layer in the functional layer so as to improve the characteristics of electronic elements, such as service life and the like.
Optionally, the functional layer comprises a hole transport layer comprising the nitrogen-containing compound provided by the present application. The hole transport layer may be composed of the nitrogen-containing compound provided by the present application, or may be composed of the nitrogen-containing compound provided by the present application together with other materials. The hole transport layer may be one layer or two or more layers.
Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device. The organic electroluminescent device may be a green light device, a red light device or a blue light device.
According to one embodiment, the electronic component is an organic electroluminescent device, the hole transport layer comprising a first hole transport layer and a second hole transport layer (also referred to as "electron blocking layer"), the first hole transport layer being closer to the anode than the second hole transport layer, the second hole transport layer comprising the nitrogen-containing compound, i.e. the electron blocking layer comprising the nitrogen-containing compound.
According to a specific embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Anode material concreteExamples 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 metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the first hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. For example, the first hole transport layer 321 may be composed of the compound NPB.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to 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 are not particularly limited in the present application. For example, the host material may be α, β -ADN.
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 are not particularly limited in the present application. For example, the guest material may be BD-1 (structure shown below).
The electron transport layer 340 may be a single layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of TPBi and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. A metal electrode containing magnesium and silver is preferable as the cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. For example, hole injection layer 310 may be composed of F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 350 may also be provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 may include LiQ.
According to an exemplary embodiment, the organic electroluminescent device is a blue light device.
According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises the nitrogen-containing compound provided by the present application.
According to an exemplary embodiment, as shown in fig. 3, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the nitrogen-containing compound of the present application. The hole transport layer 320 may be formed of the nitrogen-containing compound provided by the present application, or may be formed of the nitrogen-containing compound provided by the present application and other materials.
Optionally, the hole transport layer 320 may further include an inorganic doping material to improve hole transport properties of the hole transport layer 320.
According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transporting layer, a photoelectric conversion layer, an electron transporting layer, and a cathode, which are sequentially stacked, wherein the hole transporting layer includes the nitrogen-containing compound of the present application.
A third aspect of the application provides an electronic device comprising an electronic component according to the first aspect of the application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device described above. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting device, an optical module, etc.
According to another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, a light module, a CCD camera, or other type of electronic device.
All of the compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
The application is further illustrated by the following examples, which are not intended to be limiting in any way.
The synthesis examples are used to illustrate the synthesis of the nitrogen-containing compounds of the present application.
The synthetic route is as follows:
the raw material Sub Z may be obtained commercially or by methods well known in the art, and specific preparation methods thereof are well known in the art and will not be described herein.
1. Synthesis of intermediate IM A-X
1) Description of the Synthesis of IM A-X Using IM A-1 as an illustration
1-fluoro-9H-carbazole (4.63 g,25.00 mmol), 2-bromo-2 ' -chloro-1, 1' -biphenyl (6.68 g,25.00 mmol), tris (dibenzylideneacetone) dipalladium (0.23 g,0.25 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.24 g,0.50 mmol) and sodium tert-butoxide (4.8 g,50.0 mmol) were added to toluene (50 mL), heated to 108℃under nitrogen and stirred for 3H; then cooling to room temperature, washing the obtained reaction liquid with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was recrystallized from toluene (1 g crude: 8mL toluene) and purified to give white intermediate IMA-1 (4.83 g, yield 52%).
2) The intermediates IM A-X listed in Table 1 were synthesized by reference to the IMA-1 synthesis method, except that starting material Sub X was used in place of 1-fluoro-9H-carbazole, starting material Sub Y was used in place of 2-bromo-2 '-chloro-1, 1' -biphenyl, and the main materials employed, the synthesized intermediates, and the yields thereof were as shown in Table 1.
TABLE 1
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2. Synthesis of Compounds
Synthesis example 1: synthesis of Compound 1
Intermediate IMA-1 (18.6 g,50.00 mmol), starting Sub 1 (20.6 g,50.00 mmol), tris (dibenzylideneacetone) dipalladium (0.46 g,0.50 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.48 g,1.00 mmol) and sodium tert-butoxide (9.61 g,100.00 mmol) were added to toluene (150 mL), heated to 105℃under nitrogen and stirred for 4h; then cooling to room temperature, washing the obtained reaction liquid with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was recrystallized from toluene (1 g crude: 10mL toluene) to give compound 1 (20.9 g, 56% yield) as a white solid, mass spectrum: m/z=747.3 [ m+h ] ] + 。
Synthesis examples 2 to 22
The compounds listed in Table 2 were synthesized by the method of Synthesis example 1, except that each intermediate IMA-X was used in place of IMA-1, and Sub Z was used in place of Sub 1, and the main raw materials used, as well as the corresponding synthesized compounds, the compound yields and the mass spectrum characterization were as shown in Table 2.
TABLE 2
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Wherein, the nuclear magnetic data of the compound 11 are: 1 H NMR(600MHz，CD 2 Cl 2 )，8.12-8.80(m,2H),8.03(d,1H),7.95(d,1H),7.90(d,2H),7.81(s,1H),7.76(d,1H),7.70(t,1H),7.65-7.61(m,6H),7.59(d,2H),7.52-7.37(m.8H),7.34-7.29(m,8H),7.16(d,1H),7.04(t,1H)；
the nuclear magnetic data for compound 15 are: 1 HNMR(600MHz，CD 2 Cl 2 )，8.12(d,1H),8.03(d,1H),7.95(d,1H),7.90(d,2H),7.83-7.81(m,2H),7.75(d,1H),7.70(t,1H),7.64-7.61(m,6H),7.59(d,2H),7.53-7.42(m,8H),7.39(t,1H),7.34-7.29(m,8H),7.18(t,1H)。
3. synthesis of intermediate IMA-X (X > 16)
1) Using IMA-17 as an example to illustrate the synthesis of IMA-X (X > 16)
3, 6-difluoro-9H-carbazole (4.06 g,20.00 mmol), 3 '-chloro-3-bromobiphenyl (5.35 g,20.00 mmol), tris (dibenzylideneacetone) dipalladium (0.18 g,0.20 mmol), 2-dicyclohexylphosphorus-2', 4',6' -triisopropylbiphenyl (0.19 g,0.40 mmol) and sodium tert-butoxide (3.84 g,40.0 mmol) were added to toluene (50 mL), heated to 108℃under nitrogen and stirred for 3H; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallisation from toluene (1 g: 6mL toluene) to give the intermediate IMA-17 as a white solid (5.13 g, 66% yield).
2) The procedure of reference IMA-17 was followed to synthesize the intermediate IMA-X listed in Table 3, except that starting material Sub X was used in place of 3, 6-difluoro-9H-carbazole, starting material Sub Y was used in place of 3' -chloro-3-bromobiphenyl, and the main starting materials employed, the synthesized intermediates and their yields were as shown in Table 3.
TABLE 3 Table 3
4. Synthesis of Compounds
Synthesis example 23: synthesis of Compound 121
Intermediate IMA-17 (9.74 g,25.00 mmol), starting Sub 1 (10.28 g,25.00 mmol), tris (dibenzylideneacetone) dipalladium (0.23 g,0.25 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.24 g,0.50 mmol) and sodium tert-butoxide (4.8 g,50.0 mmol) were added to toluene (150 mL), heated to 108℃under nitrogen and stirred for 3h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was recrystallized from toluene (1 g crude: 15mL toluene) and purified to give white solid compound 121 (9.57 g, yield 50%), mass spectrum: m/z=765.3 [ m+h ]] + 。
Synthesis examples 24 to 28
The compounds listed in Table 4 were synthesized by the method of Synthesis example 23, except that each intermediate IMA-X was used in place of intermediate IM A-17, and Sub Z was used in place of Sub 1, and the main raw materials used and the corresponding synthesized compounds, compound yields and mass spectrum characterization were as shown in Table 4.
TABLE 4 Table 4
Example 1: blue organic electroluminescent device
The anode was prepared by the following procedure: will be of the thickness ofThe ITO substrate (manufactured by Corning) was cut into a size of 40mm by 0.7mm, and a test substrate having a cathode, an anode and an insulating layer pattern was prepared by using a photolithography process, and surface treatment was performed using ultraviolet ozone and O2: N2 plasma to increase the work function of the anode (test substrate) and remove scum.
Vacuum evaporating F4-TCNQ on experimental substrate (anode) to obtain a film with a thickness ofIs deposited on the hole injection layer to form a Hole Injection Layer (HIL) having a thickness of +.>Is provided.
Vacuum evaporating compound 1 on the first hole transport layer to form a film having a thickness ofElectron Blocking Layer (EBL).
On the electron blocking layer, using alpha, beta-ADN as main body, doping BD-1 according to film thickness ratio of 100:3 to form thickness ofIs an emission layer (EML).
Performing co-evaporation on TPBi and LiQ at a film thickness ratio of 1:1 to formA thick Electron Transport Layer (ETL), liQ is evaporated on the electron transport layer to form a thickness +.>Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) are mixed at 1:9, and vacuum evaporating on the electron injection layer to form a film with a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAnd forming an organic capping layer (CPL), thereby completing the manufacture of the organic light emitting device.
Example 2-example 28
An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound shown in table 6 below was substituted for the compound 1 at the time of forming the electron blocking layer.
Comparative examples 1 to 4
An organic electroluminescent device was fabricated by the same method as in example 1, except that compound a, compound B, compound C, and compound D were used instead of compound 1, respectively, in forming the electron blocking layer.
The main material structures used in the above examples and comparative examples are shown in table 5 below:
TABLE 5
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For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The device performance was analyzed under the conditions and the results are shown in table 6 below:
TABLE 6
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From the results of Table 6, it is understood that examples 1 to 28, which are compounds of the electron blocking layer, have an improvement in current efficiency (Cd/A) of at least 6.04%, an improvement in power efficiency (lm/W) of at least 6.63%, an improvement in External Quantum Efficiency (EQE) of at least 7.49%, and an improvement in lifetime (T95) of at least 20.63% in the above-mentioned organic electroluminescent devices prepared using the compounds of the present application as the electron blocking layer, as compared with comparative examples 1 to 4, which use the known compounds A, B, C and D; meanwhile, the organic electroluminescent devices prepared in examples 1 to 28 also have a low driving voltage.
In addition, as can be seen from comparing examples 1 to 28 with comparative examples 1 to 4, the compound of the present application can improve the service life and luminous efficiency of the device by introducing one or two F as substituents on the carbazolyl group, which may be because fluorine can effectively pull electrons, and avoid "running" out of electrons of the host material in the organic light emitting layer adjacent to the electron blocking layer; meanwhile, F is introduced to carbazolyl to interact with dibenzofuran/dibenzothiophene groups on aromatic amine, and at least one of the two groups of N-phenylcarbazolyl and dibenzofuran/dibenzothiophene groups is controlled to be connected with N atoms through aromatic groups, so that the distortion degree of the whole molecule can be improved, and the whole molecule has a better configuration; in contrast, the molecular weight of compound D in comparative example 4 was too small, and the entire molecular structure was too flat by directly adjacent the N atom to the N-phenylcarbazolyl group and dibenzothiophene/dibenzofuran group to which F was bonded, and the molecular weight was too low, so that compound D could not be effectively applied to the device. Further, examples 2, 3, 11, 15, etc., control the corresponding L 1 For a specific structure, the adopted compound has higher thermal stability, F on the carbazole group and other two substituents on the arylamine have higher compatibility, the function of each group is fully reflected, the transmission speed of electrons can be effectively reduced, the transmission of electrons in the device is blocked, and the service life of the device is obviously prolonged.
The preferred embodiments of the present application have been described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the scope of the technical concept of the present application, and all the simple modifications belong to the protection scope of the present application. In addition, the specific features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described further. Moreover, any combination of the various embodiments of the application can be made without departing from the spirit of the disclosure, which should also be considered as the disclosure of the application.
Claims (15)
1. A nitrogen-containing compound, characterized in that the structure of the nitrogen-containing compound is shown in formula 1:
Wherein X is selected from O or S;
ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl;
substituents in Ar are the same or different and are each independently selected from deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl;
L、L 1 and L 2 Identical or different and are each independently selected from single bonds, substituted or unsubstituted groups V 2 Unsubstituted group V 2 Selected from the group consisting of:
substituted group V 2 Has one or more substituents, each substituent being independently selected from deuterium;
and L is 1 And L 2 Are not single bonds at the same time;
m is 0, 1 or 2, n is 0, 1 or 2, and 1.ltoreq.m+n.ltoreq.2;
R 1 、R 2 identical or different and are each independently selected from deuterium, phenyl;
p 1 r represents 1 And is selected from 0 or 1;
p 2 r represents 2 And is selected from 0.
2. The nitrogen-containing compound according to claim 1, wherein the structure of the nitrogen-containing compound is represented by formula 1-1 or formula 1-2:
3. the nitrogen-containing compound according to claim 1 or 2, wherein Ar is selected from the group consisting of substituted or unsubstituted groups V 1 Unsubstituted group V 1 Selected from the group consisting of:
substituted group V 1 Each substituent is independently selected from deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl and naphthyl; and when the number of substituents is greater than 1, each substituent is the same or different.
4. The nitrogen-containing compound according to claim 1 or 2, wherein Ar is selected from the group consisting of:
5. the nitrogen-containing compound according to claim 1Wherein L is 1 Selected from the group consisting of single bonds and:
6. the nitrogen-containing compound according to claim 1, wherein,selected from the group consisting of:
wherein, represent andis linked to, # denotes and +.>Is a ligation site of (2).
7. The nitrogen-containing compound according to claim 6, wherein,selected from->
8. The nitrogen-containing compound according to claim 1, wherein L and L 2 Each independently selected from the group consisting of a single bond and:
9. a nitrogen-containing compound according to claim 1 or 2, wherein,selected from->
10. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
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11. An electronic component, characterized by comprising 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 nitrogen-containing compound according to any one of claims 1 to 10.
12. The electronic component of claim 11, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
13. The electronic element according to claim 11, wherein the functional layer comprises a hole-transporting layer, the hole-transporting layer containing the nitrogen-containing compound.
14. The electronic component of claim 13, wherein the electronic component is an organic electroluminescent device, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is closer to the anode than the second hole transport layer, and the second hole transport layer comprises the nitrogen-containing compound.
15. An electronic device comprising the electronic component as claimed in any one of claims 11 to 14.
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