CN106938999A - 一种三唑化合物及其发光器件 - Google Patents
一种三唑化合物及其发光器件 Download PDFInfo
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- CN106938999A CN106938999A CN201710145428.9A CN201710145428A CN106938999A CN 106938999 A CN106938999 A CN 106938999A CN 201710145428 A CN201710145428 A CN 201710145428A CN 106938999 A CN106938999 A CN 106938999A
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- Prior art keywords
- triazole compounds
- unsubstituted
- formula
- substituted
- aryl
- Prior art date
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- -1 triazole compounds Chemical class 0.000 title claims abstract description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical group 0.000 claims description 39
- 239000010410 layer Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000006467 substitution reaction Methods 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 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 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002979 perylenes Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 21
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 230000003111 delayed effect Effects 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000027756 respiratory electron transport chain Effects 0.000 description 9
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 150000003852 triazoles Chemical class 0.000 description 7
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical class C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 0 *1c(cccc2)c2-c2c1cccc2 Chemical compound *1c(cccc2)c2-c2c1cccc2 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000005406 washing Methods 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 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 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- VPQXYAMLSSIGMC-UHFFFAOYSA-O [NH3+]c(cc1)ncc1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 Chemical compound [NH3+]c(cc1)ncc1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 VPQXYAMLSSIGMC-UHFFFAOYSA-O 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011835 investigation Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical class CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
-
- H—ELECTRICITY
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Abstract
本发明涉及有机发光材料技术领域,具体涉及一种三唑化合物及应用该三唑化合物的发光器件。本发明的三唑化合物包括给电子基团Ar1,以及取代基团Ar2;其中,Ar2可表示氢、取代或未取代的C6~36芳香基、取代或未取代的C6~36芳香稠环基。本发明的三唑化合物结构对称,具有合成简单、路线成熟的优势。本发明的三唑化合物,通过取代基Ar2的自身空间位阻,兼顾了成膜性和热致延迟荧光性能,使用该材料的器件具有良好的稳定性。
Description
技术领域
本发明涉及有机发光材料技术领域,具体涉及一种三唑化合物及应用该三唑化合物的发光器件。
背景技术
有机电致发光器件(Organic Electroluminescence Devices,简称OLEDs),又称发光二极管,是在其中施加电压而将电能转化为光能的装置,是理想的手机、彩电等显示屏。电致发光材料与器件的研究引起了世界科技界和工业界的极大兴趣,EL器件被普遍认为能同时兼有低能耗、广视角、大面积的平板显示技术。
TADF(Thermally actiated delayed fluorescence,热活化延迟荧光)材料作为第三代发光材料,能够兼顾发光效率和材料稳定性,受到了业内广泛的关注。TADF材料多要求具有D-π-A结构,其中D为Donor(电子给体),业内常见的电子给体为芳香胺体系或咔唑体系;A为Acceptor(电子受体),具有碳氮双键的杂环体系均可以作为电子受体;π为桥连基团,桥连基团可以为芳香共轭体系,也可以是非芳香共轭体系,也可以是单键,只要能够使Donor基团和Acceptor基团非共轭的连接。
进一步的研究发现,基于D-π-A结构的化合物,只要化合物能够实现HOMO(HighestOccupied Molecular,最高占有轨道)和LUMO(Lowest Unoccupied Molecular,最低空轨道)的电子云分布分离,就能够获得较小的单线态-三线态能级差(ΔEST),成为有价值的TADF材料。也有将这种电子云分布分离,称为空间电荷分离。
现有技术中,比较常见的芳香杂环吸电子基团为吡啶基、三嗪基等六元杂环,具有TADF性能或电荷分离特征的稳定性好的五元杂环三唑化合物报道较少。
因此,需要开发一种玻璃化温度高,成膜性好的具有热活化延迟荧光性能的三唑化合物。
发明内容
本发明的首要发明目的在于提出一种三唑化合物。
本发明的第二发明目的在于提出应用该三唑化合物的发光器件。
为了完成本发明的目的,采用的技术方案为:
本发明涉及一种三唑化合物,所述三唑化合物的结构式如通式I所示,
其中,X1、X2、X3、X4、X5、X6、X7、X8、X9、X10各自独立的表示碳原子或氮原子;
Ar1表示C6~36的给电子基团;
Ar2表示氢、取代或未取代的C6~36芳香基、取代或未取代的C6~36芳香稠环基;取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基和C4~12卤素取代的杂芳基中的一种或多种;
a表示0-2的整数,b表示0-2的整数,m表示1-5的整数,n表示1-5的整数。
本发明还涉及一种发光器件,包括至少一层阳极、至少一层阴极和至少一层有机层层,所述有机层包括通式(I)所述的三唑化合物。
本发明的技术方案至少具有以下有益的效果:本发明的三唑化合物具有对称结构,其合成简单,路线成熟且成本较低。本发明的三唑化合物中通过取代基Ar2的自身空间位阻,既保持了原有的TADF性能,同时保证了成膜性,使用该材料的器件具有良好的稳定性。
附图说明
图1为本发明具体实施方式中发光器件的结构示意图。
具体实施方式
下面结合具体实施例,进一步阐述本申请。应理解,这些实施例仅用于说明本申请而不用于限制本申请的范围。
本申请涉及一种结构对称的三唑化合物,具有合成简单,路线成熟且成本较低的优势,该三唑化合物的结构式如通式I所示,
其中,X1、X2、X3、X4、X5、X6、X7、X8、X9、X10各自独立的表示碳原子或氮原子;
Ar1表示C6~36的给电子基团;
Ar2表示氢、取代或未取代的C6~36芳香基、取代或未取代的C6~36芳香稠环基;取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基和C4~12卤素取代的杂芳基中的一种或多种;
a表示0-2的整数,b表示0-2的整数,m表示1-5的整数,n表示1-5的整数。
在本发明一实施例中,当a=0时,该三唑化合物的结构式如以下通式II所示:
在本发明一实施例中,当a=1时,该三唑化合物的结构式如以下通式III所示:
在本发明一实施例中,当a=2时,该三唑化合物的结构式如以下通式IV所示:
其中,Xa、Xb、Xc、Xd、Xe各自独立的表示碳原子或氮原子。
本发明采用的给电子基团可以为咔唑及其衍生基团,或二苯胺及其衍生基团等。通过取代基Ar2的自身空间位阻,既保持了原有的TADF性能,同时保证了成膜性,使用该材料的器件具有良好的稳定性。取代基Ar2主要作用在于调节材料的成膜性,同时也辅助三唑基团提升空间电荷转移能力。当Ar2为芳香稠环基团时,由于空间的立体效应,也可极大提升了取代基Ar2的空间电荷转移能力。除了三唑基团本身作为吸电子基团,能够使化合物产生空间电荷转移之外,还可以通过引入六元含氮杂环基团(如吡啶基团,三嗪基团等),以进一步增强了材料的空间电荷转移能力。同时由于六元含氮杂环自身的电子传输性能,能够提升材料的电子传输性能,促进了载流子传输平衡,提高了器件稳定性。
作为本发明三唑化合物的一种改进,当环中不含氮原子或分别有一个、两个、三个氮原子时,三唑化合物的结构式如通式IA、通式IB、通式IC、通式ID、通式IE、通式IF、通式IG、通式IH、通式II、通式IJ、通式IK、通式IL、通式IM或通式IN所示:
在上述通式中,Ar1、Ar2所表示的含义与其在通式I中的含义相同。即,Ar1表示C6~36的给电子基团;Ar2表示氢、取代或未取代的C6~36芳香基,或取代或未取代的C6~36芳香稠环基;取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基和C4~12卤素取代的杂芳基中的一种或多种。
作为本发明三唑化合物的一种改进,的结构式如以下之一所示:
其中,R11、R12、R13、R14、R15、R16、R17、R18、R19、R20各自独立的表示氢、卤素、取代或未取代的C1~6烷基、取代或未取代的C6~12芳基,或取代或未取代的C12~24芳胺基;
R1、R2各自独立的选自取代或未取代的C1~6烷基,或取代或未取代的C6~12芳基;R11和R12可以通过共价键相连。
取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基、C4~12卤素取代的杂芳基;
A表示C原子或Si原子;
Z表示O原子、S原子、亚砜基或砜基;
n为0~3的整数。
作为本发明三唑化合物的一种改进,的结构式如以下之一所示:
其中,取代基的含义同上,即取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基和C4~12卤素取代的杂芳基中的一种。
作为本发明三唑化合物的一种改进,Ar2选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的三亚苯基、取代或未取代的联苯基,和取代或未取代的三联苯基中的任意一种。而取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基,和C4~12卤素取代的杂芳基中的任意一种。该取代基优选为取代或未取代的萘基、取代或未取代的菲基,或取代或未取代的联苯基。
在上述通式中,碳原子数为1~12的烷基,烷基可为链状烷基,也可为环烷基。位于环烷基的环上的氢可被烷基取代,烷基中碳原子数优选的下限值为2、3、4,或5;而上限值优选为3、4、5、6、8、10或12。优选地,本发明选择碳原子数为1~10的烷基。进一步优选地,本发明选择碳原子数为1~6的链状烷基或碳原子数为3~8的环烷基。更进一步优选地,本发明选择碳原子数为1~4的链状烷基或碳原子数为5~7的环烷基。其中,烷基额可以为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、己基、2-甲基-戊基、3-甲基-戊基、1,1,2-三甲基-丙基、3,3,-二甲基-丁基、庚基、2-庚基、3-庚基、2-甲基己基、3-甲基己基、异庚基,或辛基。
在上述通式中,碳原子数为6~36的芳基,例如苯基、苯烷基、至少含有一个苯基的芳基如联苯基、稠环芳烃基如萘、蒽、菲、芘均可。此外,联苯基和稠环芳烃基还可被烷基所取代。优选地,本发明选择碳原子数为6~16的芳基。进一步优选地,本发明选择碳原子数为6~24的芳基。更进一步优选地,本发明选择碳原子数为6~18的芳基。其中,芳基可以为苯基、苄基、联苯基、萘基、蒽基、菲基、芘基、苝基、三亚苯基,或三联苯基。
作为本发明三唑化合物的一种改进,三唑化合物选自以下化合物中的其中一种:
作为本发明三唑化合物的一种改进,三唑化合物选自以下化合物中的其中一种:
本发明采用如路线(a)和(b)所示合成三唑化合物。
第一步,原料芳香胺(a-1)与氯代物(a-2)反应,氮气保护条件下高温搅拌反应若干小时可得到中间体(a-3),第二步,将提纯后的中间体(a-3)与另一原料(a-4)在偶联反应条件下反应若干小时,可得到通式(I)所示的目标化合物。偶联反应可根据目标化合物的不同进行相应的调整;该偶联反应优选为通用的钯催化剂下的无水无氧反应。钯催化剂优选为四(三苯基膦)钯或醋酸钯。
其中,合成路线中的符号定义与通式(I)中的定义相同。原料(a-4)中的LG表示为反应中离去的基团,如胺基的氢原子,有机芳香硼酸的硼酸基团。
实施例1:化合物SZA-17的合成。
将0.14g(1mmol)的1-萘胺、0.43g(1mmol)的化合物(s1)、20mL N,N-二甲基苯胺加入到50mL单口茄形瓶中,抽真空除氧气,在氮气保护条件下加热到130℃反应10小时,冷却至室温,加入10mL盐酸溶液(2N)搅拌1小时后抽滤,水洗干燥,产物经柱层析提纯,洗脱剂为乙酸乙酯∶石油醚=5∶1,得到0.25g白色固体。
将0.2g中间体、0.25g(0.8mmol)的3,6-二叔丁基咔唑、77mg(0.8mmol)叔丁醇钠、10mg醋酸钯、10mg三叔丁基膦和10mL甲苯加入到50mL单口茄形瓶中,抽真空除氧气,在氮气保护条件下加热到110℃反应8小时,冷却至室温,用乙酸乙酯萃取三次、水洗、用硫酸镁干燥,旋蒸除去溶剂,经柱层析提纯,洗脱机为石油醚:乙酸乙酯=1∶1,得到0.2g白色固体,收率56%。产物质谱(m/e):902.8(M+1).ΔEST=0.49eV。
实施例2:化合物SZA-18的合成。
将0.14g(1mmol)的1-萘胺、0.43g(1mmol)的化合物(s1)、20mL N,N-二甲基苯胺加入到50mL单口茄形瓶中,抽真空除氧气,在氮气保护条件下加热到130℃反应10小时,冷却至室温,加入10mL盐酸溶液(2N)搅拌1小时后抽滤,水洗干燥,产物经柱层析提纯,洗脱剂为乙酸乙酯∶石油醚=5∶1,得到0.25g白色固体。
将0.2g(0.4mmol)中间体、0.25g(0.88mmol)的4-(9-咔唑)苯硼酸、20mg四(三苯基膦)钯、10mL甲苯、5mL碳酸钠水溶液(2N)、5mL乙醇加入到50mL单口茄形瓶中,抽真空除氧气,在氮气保护条件下加热到110℃反应8小时,冷却至室温,用乙酸乙酯萃取三次、水洗、用硫酸镁干燥,旋蒸除去溶剂,经柱层析提纯,洗脱机为石油醚∶乙酸乙酯=1∶1,得到0.22g白色固体,收率65%。产物质谱(m/e):830.7(M+1),ΔEST=0.53eV。
实施例3:化合物SZA-52的合成
采用与合成实施例1相同的方式,只是用2-[(3’-苯基)苯基]-5-氨基吡啶代替1-萘胺,用咔唑代替3,6-二叔丁基咔唑。得到白色固体。收率46%,产物质谱(m/e):782.2(M+2),ΔEST=0.41eV。
实施例4:化合物SZB-37的合成
采用与合成实施例1相同的方式,只是用4-(9-咔唑基)对联苯胺代替1-萘胺,用二苯胺代替3,6-二叔丁基咔唑。得到白色固体。收率67%,产物质谱(m/e):874.1(M+1),ΔEST=0.49eV。
合成实施例5化合物SZB-46的合成
采用与合成实施例1相同的方式,只是用化合物(s2)代替化合物(s1),用化合物(s3)代替1-萘胺,用化合物(s4)代替3,6-二叔丁基咔唑。得到白色固体。收率59%,产物质谱(m/e):953.7(M+1),ΔEST=0.78eV。
实施例6:化合物SZC-22的合成
采用与合成实施例1相同的方式,只是用N,N-二苯基联苯二胺代替1-萘胺,用化合物(s5)代替3,6-二叔丁基咔唑。得到白色固体。收率67%,产物质谱(m/e):958.8(M+2),ΔEST=0.79eV。
实施例7:化合物SZC-32的合成
采用与合成实施例2相同的方式,只是用N,N-二苯基联苯二胺代替1-萘胺,用化合物9-苯基咔唑-3-硼酸代替4-(9-咔唑)苯硼酸。得到白色固体。收率54%,产物质谱(m/e):1023.0(M+1),ΔEST=0.56eV。
实施例8:化合物SZC-43的合成
采用与合成实施例1相同的方式,只是用N,N-二苯基联苯二胺代替1-萘胺,用化合物二甲苯胺代替3,6-二叔丁基咔唑,用化合物(s2)代替化合物(s1)。得到白色固体。收率69%,产物质谱(m/e):960.2(M+2),ΔEST=0.49eV。
实施例9:化合物SZD-26的合成
采用与合成实施例1相同的方式,只是用化合物(s6)代替1-萘胺,用化合物二甲苯胺代替3,6-二叔丁基咔唑,用化合物(s2)代替化合物(s1)。得到白色固体。收率55%,产物质谱(m/e):931.3(M+2),ΔEST=0.40eV。
材料的成膜性测试:将得到的化合物制成20mg/ml的氯苯溶液。用清洗过的ITO导电玻璃作为基底,先在上面用旋涂法涂一层约40nm厚的ITO/PEDOT:PSS,然后再旋涂含有本发明化合物的溶液,转速为2000转/秒。通过原子力显微镜(AFM)观察薄膜的表面平整度。
本发明的9个化合物,上下起伏均不超过3nm,没有发现针孔和微晶出现。其中,SZA-17,SZB-46,SZC-22,SZC-43,SZD-26上下起伏不超过2nm。
基于所述三唑化合物,本发明提供一种应用所述三唑化合物的发光器件。
请参阅图1,为本发明提供的发光器件的结构示意图。所述发光器件100包括依次沉积形成的阳极11、空穴传输层12、发光层13、电子传输层14和阴极15。其中所述空穴传输层12、发光层13、电子传输层14均为有机层,所述阳极11与所述阴极15与电连接。
所述发光层13可以只有本发明提供的三唑化合物,使所述发光器件100为非掺杂器件。所述发光层13可以还有其他材料,使所述发光器件100为掺杂器件。当采用掺杂器件时,本发明提供的三唑化合物在所述发光层13中的比例不受限制。
所述空穴传输层12可以采用本发明提供的三唑化合物,也可以选择其他芳香胺类有机物作为空穴传输层,只要能够将引入的空穴传递到所述发光层13即可。所述空穴传输层12可以为一层,也可以为多层。
所述电子传输层14可以采用本发明提供的三唑化合物,也可以选择其他化合物作为电子传输层,对电子传输层的化合物结构没有具体的要求,只要能够将引入的电子传递到发光层即可。作为电子传输层14的化合物结构,可以选择含氮的杂环化合物,也可以选择碳氢元素组成的螺环芳香化合物,也可以选择金属配合物。所述电子传输层14可以为一层,也可以为多层。
为了示意性的证明本发明提供的三唑化合物作为发光器件材料的优良特性,发光器件按照如下结构设计:阳极/空穴传输层/本发明所述三唑化合物/电子传输层/阴极。其中,阳极为经过三氧化钼(MoO3)修饰的ITO电极;阴极为经过氟化锂(LiF)修饰的铝(A1)电极。空穴传输材料选择N,N′-二(1-萘基)-N,N′-二(2-萘基)-1,1′-联苯-4-4′-二胺(TNB),电子传输层选择1,3,5-三[(3-吡啶基)-3-苯基]苯(TmPyPB)。所述发光器件为非掺杂发光器件。
所述发光器件100的制作工艺如下:
将涂布了氧化铟锡(ITO)透明导电层的玻璃板在商用清洁剂中超声处理,用去离子水冲洗后,在丙酮:乙醇混合溶剂中超声,在洁净环境下烘烤至完全除去水粉,用紫外光清洗剂曝光20分钟。将上述清洗好的玻璃基板置于真空腔内,抽真空至1×10-3~10-5Pa,蒸镀一层MoO3,蒸镀厚度为10-100nm,继续蒸镀一层TNB,厚度10-100nm,继续蒸镀一层本发明所述三唑化合物,厚度10-50nm,继续蒸镀一层TmPyPB,厚度10-100nm,继续蒸镀一层LiF,厚度0.4-0.6nm,继续蒸镀一层铝电极,厚度20-200nm。
本发明所用的材料为如下结构:
为了进一步说明本发明提供的三唑化合物在发光器件中的优良特性,通过采用不同结构的所述三唑化合物,结合上述制备工艺,分别制作具有实施例1-9的所述的三唑化合物的发光器件100,所述发光器件100为非掺杂器件,其结构为制备如下器件结构:ITO/MoO3(5nm)/TNB(40nm)/三唑化合物(30nm)/TmPyPB(60nm)/LiF(0.5nm)/Al(100nm)。同时采用化合物(d1)、(d2)、(d3)制备对比实施例1(D1)、对比实施例2(D2)、对比实施例3(D3)的非掺杂发光器件,将本发明的发光器件与对比实施例的发光器件进行性能对比。
发光器件寿命为1000cd/m2的条件下进行测试,测试结果如下:
实验结果如表1所示:
表1:
与相关技术相比,本发明提供的三唑化合物的有益效果在于:本发明的三唑化合物具有对称结构,其合成简单,路线成熟且成本较低。另外,本发明的三唑化合物中通过取代基Ar2的自身空间位阻,既保持了原有的TADF性能,同时保证了成膜性,使用该材料的器件具有良好的稳定性。
本发明虽然以较佳实施例公开如上,但并不是用来限定权利要求,任何本领域技术人员在不脱离本发明构思的前提下,都可以做出若干可能的变动和修改,因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
Claims (9)
1.一种三唑化合物,其特征在于,所述三唑化合物结构式如通式I所示,
其中,X1、X2、X3、X4、X5、X6、X7、X8、X9、X10各自独立的表示碳原子或氮原子;
Ar1表示C6~36的给电子基团;
Ar2表示氢、取代或未取代的C6~36芳香基、取代或未取代的C6~36芳香稠环基;取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基和C4~12卤素取代的杂芳基中的一种或多种;
a表示0-2的整数,b表示0-2的整数,m表示1-5的整数,n表示1-5的整数。
2.根据权利要求1所述的三唑化合物,其特征在于,所述三唑化合物的结构式如通式IA、通式IB、通式IC、通式ID、通式IE、通式IF、通式IG、通式IH、通式II、通式IJ、通式IK、通式IL、通式IM或通式IN所示,
其中,Ar1表示C6~36的给电子基团;
Ar2表示氢、取代或未取代的C6~36芳香基,或取代或未取代的C6~36芳香稠环基;取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基和C4~12卤素取代的杂芳基中的一种或多种。
3.根据权利要求1或2所述的三唑化合物,其特征在于,Ar1的结构式如以下之一所示:
其中,R11、R12、R13、R14、R15、R16、R17、R18、R19、R20各自独立的表示氢、卤素、取代或未取代的C1~6烷基、取代或未取代的C6~12芳基,或取代或未取代的C12~24芳胺基;
R1、R2各自独立的选自取代或未取代的C1~6烷基,或取代或未取代的C6~12芳基;
取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基、C4~12卤素取代的杂芳基;
A表示C原子或Si原子;
Z表示O原子、S原子、亚砜基或砜基;
n为0~3的整数。
4.根据权利要求1所述的三唑化合物,其特征在于,Ar2选自取代或未取代的萘基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的三亚苯基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的联苯基,和取代或未取代的三联苯基中的一种;
取代基选自卤素、C1~12烷基、C1~12卤素取代的烷基、C6~12芳基、C6~12卤素取代的芳基、C4~12杂芳基,和C4~12卤素取代的杂芳基中的一种或多种。
5.根据权利要求4所述的三唑化合物,其特征在于,所述三唑化合物选自以下化合物中的其中一种:
6.根据权利要求1所述的三唑化合物,其特征在于,所述三唑化合物选自以下化合物中的其中一种:
7.根据权利要求1所述的三唑化合物,其特征在于,所述三唑化合物选自以下化合物中的其中一种:
8.根据权利要求1所述的三唑化合物,其特征在于,所述三唑化合物选自以下化合物中的其中一种:
9.一种发光器件,其特征在于,包括至少一层阳极、至少一层阴极和至少一层有机层,所述有机层包括权利要求1至8任一项所述的三唑化合物。
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CN111004189B (zh) * | 2019-12-11 | 2021-03-23 | 吉林大学 | 一种有机荧光小分子材料及其制备方法和在荧光检测中的应用 |
EP3943492A1 (en) * | 2020-07-24 | 2022-01-26 | Noctiluca S.A. | Tadf materials comprising 4-(3-(2-(10h-phenoxazin-10-yl)pyridin-5-yl)-9h-carbazol-9-yl)benzonitrile derivatives and related compounds for use in oleds |
CN114230532A (zh) * | 2021-12-21 | 2022-03-25 | 吉林大学 | 一种三氮唑衍生物、基于该类材料的荧光传感器及其在检测化学战剂中的应用 |
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