CN111116589B - 含氮杂环化合物、电子器件及其应用 - Google Patents
含氮杂环化合物、电子器件及其应用 Download PDFInfo
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- CN111116589B CN111116589B CN201911367548.9A CN201911367548A CN111116589B CN 111116589 B CN111116589 B CN 111116589B CN 201911367548 A CN201911367548 A CN 201911367548A CN 111116589 B CN111116589 B CN 111116589B
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- Prior art keywords
- nitrogen
- organic
- containing heterocyclic
- electronic device
- heterocyclic compound
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- -1 Nitrogen-containing heterocyclic compound Chemical class 0.000 title claims abstract description 36
- 239000000463 material Substances 0.000 claims description 47
- 239000010410 layer Substances 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 6
- 230000005669 field effect Effects 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 3
- 230000005525 hole transport Effects 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 abstract description 6
- 230000007704 transition Effects 0.000 abstract description 4
- 230000005283 ground state Effects 0.000 abstract description 3
- 230000002950 deficient Effects 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract description 2
- 238000012546 transfer Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- DJMOXMNDXFFONV-UHFFFAOYSA-N 1,3-dimethyl-7-[2-(n-methylanilino)ethyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(C)C1=CC=CC=C1 DJMOXMNDXFFONV-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- IVXBGKPGZOETEW-UHFFFAOYSA-N 10-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9,9-dimethylacridine Chemical compound CC1(C)C2=C(C=CC=C2)N(C2=CC=C(C=C2)C2=NC(=NC(=N2)C2=CC=CC=C2)C2=CC=CC=C2)C2=C1C=CC=C2 IVXBGKPGZOETEW-UHFFFAOYSA-N 0.000 description 8
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 4
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 4
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 4
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 3
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- AVFUHBJCUUTGCD-UHFFFAOYSA-M [Br-].[Mg+]C Chemical class [Br-].[Mg+]C AVFUHBJCUUTGCD-UHFFFAOYSA-M 0.000 description 2
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229940125936 compound 42 Drugs 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229940102398 methyl anthranilate Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- WUQDRRXKNVIWIR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-bromobenzene Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)C1=CC=CC=C1 WUQDRRXKNVIWIR-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F7/0816—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 said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
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Abstract
本发明公开含氮杂环化合物、电子器件及其应用。所述含氮杂环化合物，具有以下结构:
Description
技术领域
本发明涉及电致发光材料领域，尤其涉及含氮杂环化合物、电子器件及其应用。
背景技术
有机发光二极管(organic light-emitting diodes,OLED)，以其主动发光、响应速度快、可视角度大、驱动电压低、节能、更轻薄、可柔性显示等优点，可满足消费者对显示技术的新要求，在照明显示领域具有广泛的应用前景，市场需求巨大。
近年来，OLED技术虽然取得了巨大的进步，但作为起主导作用的有机发光客体材料依然很大程度上限制了OLED的发展。第一代OLED材料所使用的传统荧光材料由于其产生的单重态激子与三重态激子的比例为1：3，导致OLED的理论内量子效率(IQE)最高为25％。由于重原子具有自旋轨道耦合作用，基于重金属配合物材料的第二代磷光材料可同时利用单线态和三重态激子，使得OLED的理论IQE最高可达100％。然而，磷光材料所使用重金属的大多数为铱、铂等贵金属，价格昂贵，资源短缺。
基于荧光材料和磷光材料的不足，日本九州大学Adachi课题组提出热活化延迟荧光(Thermally Activated Delayed Fluorescence,TADF)材料。纯有机TADF材料不含有重金属，并且利用分子具有较小的单重态和三重态能极差((ΔEST)，使得三重态激子可通过反向系间窜越(RISC)回到单重态，再以辐射跃迁的方式回到基态，这样也可以实现100％的IQE。
对于TADF材料而言，同时实现快速的RISC过程以及高的光致发光量子效率(PLQY)是实现高效OLED的关键，包括材料稳定性和效率等指标有待提高，也是目前亟需解决的问题。
有机发光材料的发展对OLED的发展起着关键的作用，因此开发新型的、稳定高效的有机发光材料成为了该领域的研究目标。
发明内容
鉴于上述现有技术的不足，本发明的目的在于提供含氮杂环化合物、电子器件及其应用，旨在解决现有基于TADF材料的热稳定性低和效率低的问题。
本发明的技术方案如下：
一种含氮杂环化合物，其中，具有以下结构:
其中，Ar为取代或未取代的环原子数为5～20的芳香环基或环原子数为5～20的芳香杂环基；
X1选自单键、-N(R1)-、-O-、-S-、-S＝O-、-SO2-、-C(R1R1’)-、-S(R1R1’)-、-P(R1)-、-P＝O(R1)-中的任意一种；
X2选自单键、-N(R2)-、-O-、-S-、-S＝O-、-SO2-、-C(R2R2’)-、-S(R2R2’)-、-P(R2)-、-P＝O(R2)-中的任意一种；
M1、M2、R1、R1’、R2和R2’各自独立地选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基；
Y1和Y2各自独立地选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基；
其中，Y1、Y2、M1、M2、R1、R1’、R2和R2’均能够相互以共价键方式相连成环。
进一步地，Ar选自以下结构中的一种：
进一步地，具有以下结构中的一种:
其中，M1、M2、R1、R1’、R2和R2’各自独立地选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基。
更进一步地，M1、M2、R1、R1’、R2和R2’各自独立地选自以下结构中的一种：
进一步地，具有以下结构中的一种：
一种电子器件，其中，包括本发明所述的含氮杂环化合物。
进一步地，所述电子器件为有机电致发光器件、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机传感器、有机光伏电池、有机自旋电子器件中的一种。
更进一步地，所述电子器件为有机电致发光器件，所述有机电致发光器件包括功能层，所述功能层由质量百分含量为0.1～99.9％的含氮杂环化合物和质量百分含量为0.1～99.9％的有机功能材料组成；
所述有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、激子阻隔材料、荧光发光材料、磷光发光材料、主体材料及有机染料中的一种。
进一步地，所述电子器件为有机电致发光器件，所述有机电致发光器件包括发光层，所述发光层包括本发明所述的含氮杂环化合物。
本发明所述的电子器件在电子设备中的应用。
有益效果：本发明的含氮杂环化合物具有热活化延迟荧光的性质，其以含氮杂环为电子给体(Donor)，与缺电子的受体(Acceptor)基团相连接，构成一类具有分子内电荷转移的D-A型分子，同时利用D-A之间大的扭转角以减小分子前线轨道的重叠，从而减小单重态-三重态能级，使得三重态激子可通过反向系间穿越回到单重态，最后以辐射跃迁的方式回到基态发出荧光，以提高激子利用率，最终达到提高器件效率的目的。
具体地，本发明具有以下优点：
(1)上述含氮杂环化合物利用扭曲的D-A结构使得HOMO和LUMO有效分离，且含氮杂环化合物的ΔEST小于或等于0.3eV，足够小的ΔEST可以实现TADF性质。
(2)上述含氮杂环化合物将多个D-A发光体部分连接在一个单分子上，可以增强发光体的吸收和光致发光量子产率(PLQY)。
(3)上述含氮杂环化合物通过拓展分子共轭提高分子刚性，可以最小化分子激发态中的非辐射跃迁过程，并且高的分子刚性对于提高PLQY至关重要。
(4)上述含氮杂环化合物的玻璃化转变温度Tg大于或等于120℃，分解温度Td大于或等于350℃，高的Tg和Td使得材料具有良好的热稳定性，材料的应用范围更广。
(5)上述含氮杂环化合物可通过连接不同的受体单元来调节结构，以实现多种波长的发射光。使其作为有机发光层客体材料应用于电致发光器件中具有良好的综合性能。
具体实施方式
本发明提供含氮杂环化合物、电子器件及其应用，为使本发明的目的、技术方案及效果更加清楚、明确，以下对本发明进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
实施例1：化合物61的制备：
(1)中间体1-1的制备，反应式如下：
选取100mL两口烧瓶，在氩气保护下加入1，3-二溴苯(2.36g，10mmol)，邻氨基苯甲酸甲酯(3.62g，24mmol)，醋酸钯(224.5mg，1mmol)，碳酸铯(13.0g，40mmol)，三叔丁基磷四氟硼酸盐(754.3mg，2.6mmol)和30mL甲苯，120℃下反应12小时。冷却至室温后，经硅藻土过滤掉无机盐，硅胶柱层析分离，得白色固体2.86g，产率76％。MS(EI):m/z376.1[M+]。
(2)给体单元(a)的制备，反应式如下：
选取200mL施兰克(Schlenk)瓶，在氩气保护下加入中间体1-1(1.88g，5mmol)，再加入20mL无水无氧四氢呋喃，在0℃条件下再逐滴加入甲基溴化镁(18.75mL，30mmol)。在室温下搅拌4h，反应结束用饱和氯化铵溶液淬灭，DCM(3×50mL)萃取，水洗(3×50mL)，有机相用无水Na2SO4干燥，通过旋转蒸发除去多余溶剂，最终得到中间产物为叔醇，为淡黄色液体，干燥后直接投入下一步反应。
在氩气保护下，将上述中间产物加入100mL圆底烧瓶中，加入15mL二氯甲烷，再加入10mL三氟化硼乙醚，室温搅拌过夜。反应结束后在冰浴条件下加入氢氧化钠溶液中和淬灭，用DCM(3×50mL)萃取，水洗(3×50mL)，有机相用无水Na2SO4干燥，旋转蒸发除去多余溶剂，硅胶柱层析分离，得白色固体0.85g，两步反应综合产率：50％。1H NMR(500MHz,DMSO-d6)δ[ppm]:8.6(s,1H),7.34(ddd,J＝13.2,7.9,1.4Hz,2H),7.26(dd,J＝8.0,1.2Hz,1H),7.15-7.04(m,3H),6.97(ddd,J＝8.2,7.2,1.4Hz,1H),6.88(td,J＝7.4,1.3Hz,1H)，6.73(ddd,J＝8.2,7.2,1.3Hz,1H),6.64-6.58(m,1H),6.33(d,J＝8.4Hz,1H),1.83(s,6H),1.43(s,6H).13C NMR(125MHz,DMSO-d6)δ[ppm]:139.00,137.59,136.14,135.99,130.34,129.55,127.41,126.48,126.12,123.86,123.46,121.29,120.50,118.67,114.70,112.47,110.16,106.78,35.65,34.61,32.56,28.86。MS(EI):m/z 340.2[M+]。
(3)化合物61的制备，反应式如下：
选取50mL两口烧瓶，在氩气保护下加入给体单元(a)(340mg，1mmol)，2-(4-溴苯基)-4，6-二苯基-1，3，5-三嗪(0.46g，1.2mmol)，醋酸钯(11.2mg，0.05mmol)，叔丁醇钠(192.2mg，2mmol)，三叔丁基磷四氟硼酸盐(37.7mg，0.13mmol)和10mL甲苯，120℃下反应12小时。冷却至室温后，经硅藻土过滤掉无机盐，硅胶柱层析分离，得绿色粉末，产率73％。1HNMR(500MHz,CDCl3)δ[ppm]:9.01(d,J＝8.4Hz,2H),8.86-8.73(m,4H),7.67-7.58(m,6H),7.52(d,J＝8.4Hz,2H),7.38(dd,J＝7.7,1.3Hz,1H),7.16(d,J＝1.5Hz,1H),7.03(d,J＝8.8Hz,1H),6.99-6.95(m,1H),6.94-6.89(m,2H),6.86(dd,J＝7.8,1.1Hz,1H),6.73(s,1H),6.16(d,J＝9.6Hz,1H),5.90(d,J＝8.8Hz,1H),2.11(s,6H),1.53(s,6H).13C NMR(125MHz,CDCl3)δ[ppm]:171.86,171.11,145.95,138.77,138.24,138.01,137.77,136.09,132.71,132.02,131.90,131.73,129.92,129.04,128.73,127.79,126.55,126.51,124.61,123.43,123.21,121.11,120.05,113.76,113.70,111.60,108.02,36.21,34.54,33.61,29.16。MS(EI):m/z 647.3[M+]。
实施例2：化合物62的制备，反应式如下：
利用与化合物61相同的合成方式来制备化合物62，不同之处在于使用2-(4-溴苯基)-2，6-二苯基嘧啶代替实施例1中的2-(4-溴苯基)-4，6-二苯基-1，3，5-三嗪，得绿色粉末，产率72％。1H NMR(500MHz,CDCl3)δ[ppm]:8.78(dd,J＝8.0,1.7Hz,2H),8.55(d,J＝8.4Hz,2H),8.35(dd,J＝7.8,1.9Hz,2H),8.12(s,1H),7.64-7.51(m,9H),7.39(d,J＝7.6Hz,1H),7.17(t,J＝8.2Hz,1H),7.05(d,J＝8.8Hz,1H),7.00-6.83(m,4H),6.74(s,1H),6.26-6.08(m,1H),5.91(d,J＝8.8Hz,1H),2.12(s,6H),1.54(s,6H).13C NMR(125MHz,CDCl3)δ[ppm]:165.01,164.69,163.99,144.34,138.74,138.29,138.06,137.98,137.74,132.12,131.99,130.94,130.79,130.00,129.88,128.98,128.51,128.50,127.77,127.31,126.53,126.46,124.58,123.39,123.16,121.08,120.00,113.74,113.68,111.57,110.45,107.98,36.18,34.50,33.59,29.14。MS(EI):m/z 646.3[M+]。
实施例3：化合物70的制备，反应式如下：
利用与化合物61相同的合成方式来制备化合物70，不同之处在于使用4-溴-N-(4-叔丁基苯基)-1，8-萘酰亚胺代替实施例1中的2-(4-溴苯基)-4，6-二苯基-1，3，5-三嗪，得红色粉末，产率75％。MS(EI):m/z 667.3[M+]。
实施例4：化合物77的制备，反应式如下：
氩气保护下加入化合物70(667mg，1mmol)，碘苯(408mg，2mmol)，铜粉(12.8mg，0.2mmol)，碘化亚铜(19.0mg，0.1mmol)，碳酸钾(276mg，2mmol)和10mL二苯甲醚，180℃下反应24小时。冷却至室温后，减压蒸馏掉溶剂，硅胶柱层析分离，得白色固体，产率50％。MS(EI):m/z743.4[M+]。
实施例5：化合物95的制备，反应式如下：
选取50mL两口烧瓶，氩气保护下加入给体单元(a)(340mg，1mmol)，5-(4-溴苯基)-5H-二苯并[b，d]硼(318mg，3mmol)，铜粉(25.6mg，0.4mmol)，碘化亚铜(38.0mg，0.2mmol)，碳酸钾(552mg，4mmol)和15mL二苯甲醚，180℃下反应24小时。冷却至室温后，减压蒸馏掉溶剂，硅胶柱层析分离，得白色固体，产率55％。MS(EI):m/z 816.4[M+]。
实施例6：化合物84的制备：
(1)本实施例的一种含氮杂环化合物给体单元(b)的制备，反应式如下:
利用与给体单元(a)相同的合成方式来制备给体单元(b)，不同之处在于使用氘代甲基溴化镁代替实施例1中的甲基溴化镁，得到给体单元(b)，两步反应综合产率：46％。MS(EI):m/z 352.3[M+]。
(2)化合物84的制备，反应式如下:
利用与化合物61相同的合成方式来制备化合物84，不同之处在于使用给体单元(b)代替实施例1中的给体单元(a)，得绿色粉末，产率70％。MS(EI):m/z 658.4[M+]。
实施例7：化合物9的制备：
(1)本实施例的一种含氮杂环化合物给体单元(c)的制备，反应式如下:
利用与给体单元(a)相同的合成方式来制备给体单元(c)，不同之处在于使用2,5-二溴吡啶代替实施例1中的1，3-二溴苯，得白色粉末，产率38％。MS(EI):m/z 341.2[M+]。
(2)化合物9的制备，反应式如下:
利用与化合物61相同的合成方式来制备化合物9，不同之处在于使用给体单元(c)代替实施例1中的给体单元(a)，得绿色粉末，产率71％。MS(EI):m/z 955.4[M+]。
实施例8：化合物24的制备：
本实施例的一种含氮杂环化合物给体单元(d)的制备，反应式如下:
利用与给体单元(a)相同的合成方式来制备给体单元(d)，不同之处在于使用中间体8-1代替实施例1中的1，3-二溴苯，使用苯胺代替实施例1中的邻氨基苯甲酸甲酯，使用氘代甲基溴化镁代替实施例1中的甲基溴化镁，得白色粉末，产率40％。MS(EI):m/z 352.3[M+]。
(2)化合物24的制备,反应式如下:
利用与化合物61相同的合成方式来制备化合物24，不同之处在于使用给体单元(d)代替实施例1中的给体单元(a)，得绿色粉末，产率72％。MS(EI):m/z 966.5[M+]。
实施例9：化合物42的制备，反应式如下：
(1)本实施例的一种含氮杂环化合物给体单元(e)的制备，反应式如下:
利用与给体单元(a)相同的合成方式来制备给体单元(e)，不同之处在于使用中间体9-1代替实施例1中的1，3-二溴苯，使用苯基溴化镁代替实施例1中的甲基溴化镁，得白色粉末，产率49％。MS(EI):m/z 438.2[M+]。
化合物42的制备，反应式如下:
选取50mL两口烧瓶，在氩气保护下加入给体单元(e)(438mg，1mmol)，1-溴-4-(苯磺酰基)苯(355.2mg，1.2mmol)，醋酸钯(22.4mg，0.1mmol)，叔丁醇钠(384mg，4mmol)，三叔丁基磷四氟硼酸盐(75.4mg，0.26mmol)和10mL甲苯，120℃下反应12小时。冷却至室温后，经硅藻土过滤掉无机盐，硅胶柱层析分离，得白色粉末，产率71％。MS(EI):m/z 870.2[M+]。
测试：
测定实施例1～9的化合物，化合物DMAC-TRZ[10-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine，即10-(4-(4,6-二苯基-1,3,5-三唑-2-基)苯基)-9,9-二甲基-9,10-二氢吖啶]的玻璃化转变温度、分解温度。化合物的能级利用含时密度泛函理论(TD-DFT)通过Gaussian09软件模拟，运用函数B3LYP方法计算。表1列出了实施例1～9的化合物和DMAC-TRZ的能级数据。
表1、能级数据
由表1可以看出，实施例1～9的化合物的HOMO和LUMO能极差较小，表明实施例1～9的化合物热稳定性均较好；同时，实施例1～9的化合物的ΔEST均很小，说明包括实施例1～9的化合物的材料的发光效率较高。
进一步的，实施例1和例2得到的化合物61和化合物62、DMAC-TRZ可以用于电致发光器件中的发光层。
器件具体结构为：
器件1：
ITO/HAT-CN(5nm)/TAPC(30nm)/mCP(10nm)/DPEPO:10wt％化合物61(20nm)/DPEPO(10nm)/TmPyPB(30nm)/Liq(1.5nm)/Al(100nm)
器件2：
ITO/HAT-CN(5nm)/TAPC(30nm)/mCP(10nm)/DPEPO:10wt％化合物62(20nm)/DPEPO(10nm)/TmPyPB(30nm)/Liq(1.5nm)/Al(100nm)
器件3：
ITO/HAT-CN(5nm)/TAPC(30nm)/mCP(10nm)/DPEPO:10wt％DMAC-TRZ(20nm)/DPEPO(10nm)/TmPyPB(30nm)/Liq(1.5nm)/Al(100nm)其中HAT-CN、TAPC、mCP、DPEPO和TmPyPB的结构式分别如下：
氧化铟锡导电玻璃(ITO)依次经用去离子水、丙酮和异丙醇超声清洗30分钟，紫外臭氧处理15分钟。然后在高真空条件下依次蒸镀各有机层及阴极Al层，并在手套箱中封装得OLED器件。
进一步的，对以上电致发光器件进行性能测试，结果如下表2所示：
表2、测试结果
由表2可以看出，实施例1的化合物61为客体材料的OLED发光器件寿命高于DMAC-TRZ。实施例2的化合物62为客体材料的OLED发光器件发光效率与寿命均高于DMAC-TRZ。这主要由于实施例中化合物61和化合物62的玻璃化转变温度均在110℃以上，均高于DMAC-TRZ，说明实施例1和2的化合物的热稳定性均优于DMAC-TRZ。
由器件性能数据可得出，本发明上述的实施例实现了如下技术效果：基于含氮杂环化合物，给受体之间近乎垂直的扭转角，导致HOMO和LUMO的有效分离以减小分子前线轨道的重叠，从而获得较低的ΔEST，具有热活化延迟荧光性质，进而实现更高的能量利用率，获得很高的荧光量子产率；同时通过拓展分子共轭提高分子刚性，具有非常好的热力学稳定性；上述热激活延迟荧光材料可作为OLED中的热激活延迟荧光(TADF)发光层客体材料，通过掺入主体材料，获得了高的器件效率和良好的稳定性。
本发明中所涉及的其他衍生物的制备方法与相应的实施例方法相似，只是链接的给体和受体的种类数量不同，通过Buchwald-Hartwig偶联均可制得。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (6)
1.一种含氮杂环化合物，其特征在于，具有以下结构中的一种：
2.一种电子器件，其特征在于，包括权利要求1所述的含氮杂环化合物。
3.根据权利要求2所述的电子器件，其特征在于，所述电子器件为有机电致发光器件、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机传感器、有机光伏电池、有机自旋电子器件中的一种。
4.根据权利要求3所述的电子器件，其特征在于，所述电子器件为有机电致发光器件，所述有机电致发光器件包括功能层，所述功能层由质量百分含量为0.1～99.9％的含氮杂环化合物和质量百分含量为0.1～99.9％的有机功能材料组成；
所述有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、激子阻隔材料、荧光发光材料、磷光发光材料、主体材料及有机染料中的一种。
5.根据权利要求2所述的电子器件，其特征在于，所述电子器件为有机电致发光器件，所述有机电致发光器件包括发光层，所述发光层包括权利要求1-2任一项所述的含氮杂环化合物。
6.权利要求2-5任一项所述的电子器件在电子设备中的应用。
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