CN108191859A - 一类用作蓝色荧光材料的氮杂芳香化合物及应用 - Google Patents
一类用作蓝色荧光材料的氮杂芳香化合物及应用 Download PDFInfo
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- CN108191859A CN108191859A CN201810078654.4A CN201810078654A CN108191859A CN 108191859 A CN108191859 A CN 108191859A CN 201810078654 A CN201810078654 A CN 201810078654A CN 108191859 A CN108191859 A CN 108191859A
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- unsubstituted
- substituted
- substitution
- aryl
- aromatic compound
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- 239000000463 material Substances 0.000 title claims abstract description 36
- -1 azepine aromatic compound Chemical class 0.000 title claims abstract description 33
- 238000005401 electroluminescence Methods 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- 238000006884 silylation reaction Methods 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000003205 fragrance Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical class CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005013 aryl ether group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 150000003577 thiophenes Chemical class 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 150000003851 azoles Chemical class 0.000 claims 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 229910052594 sapphire Inorganic materials 0.000 abstract description 2
- 239000010980 sapphire Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940125833 compound 23 Drugs 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 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
- 238000005899 aromatization reaction Methods 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 0 C*C1*(C)**C1* Chemical compound C*C1*(C)**C1* 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000004411 aluminium Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 1
- JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical compound [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/46—Aniline
-
- 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
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- 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
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract
本发明属于有机光电材料技术领域,尤其涉及一类用作蓝色荧光材料的氮杂芳香化合物及应用。本发明提供一系列氮杂芳香化合物,作为荧光材料新的核心结构,制备出天蓝色的发光材料,这类有机化合物不仅发光效率高,而且还可以通过取代基和杂原子的位置来精细调节发射光的波长,此类材料可应用在有机电致发光器件中。
Description
技术领域
本发明属于有机光电材料技术领域,尤其涉及一类用作蓝色荧光材料的氮杂芳香化合物及应用。
背景技术
有机电致发光技术作为新兴显示技术,具有高亮度、驱动电压低、发光效率高、结构简单、视角大等优点,具有十分广泛的应用前景。目前,在用于制备全色有机发光二极管的红、绿、蓝三基色材料中,红光材料和绿光材料已基本达到工业化要求,而蓝光材料在荧光效率、色纯度、寿命、亮度等方面距离工业化应用仍有较大距离,成为该行业的技术难题。
研究发现,当三重态能级升高时,非辐射跃迁速率增大幅度往往超过辐射跃迁的速率,使得发光效率下降;并且蓝光短波长发射需要更高能量的激发,材料本身的稳定性也备受考验,因此在蓝光材料的研究中发光效率提高和发射波长蓝移是不可能同时实现的。所以蓝光材料可以转化成绿光和红光材料,反之,则不可行。
因此,决定OLED性能优劣的根本因素为材料的选择。目前,蓝光材料主要以咔唑、蒽、篦、苝、芴、苯乙烯等作为核心结构。寻找一个新的蓝光材料核心结构,进一步设计新型蓝色发光材料,这对于改善和提高蓝光OLED材料的性能有着重要的意义。
发明内容
本发明针对上述现有技术存在的不足,提供一类用作蓝色荧光材料的氮杂芳香化合物及应用。
本发明解决上述技术问题的技术方案如下:一类用作蓝色荧光材料的氮杂芳香化合物,其结构式如下:
其中,X1、X2、X3、X4、X5、X6、X7、X8、X9各自独立的为N或CR1;
R1为氢、氘、卤素、取代或未取代的芳基、取代或未取代的亚芳基、取代或未取代的亚杂芳基、取代或未取代的杂芳基、取代或未取代的苯并杂环芳基、取代或未取代的多环杂芳基、取代或未取代的苯并杂环脂基、取代或未取代的芳氨基、取代或未取代的芳硫基、取代或未取代的亚芳硫基、取代或未取代的芳醚基、取代或未取代的芳基烷基、取代或未取代的二烷基芳基甲硅烷基、取代或未取代的金刚烷、取代或未取代的三芳基甲硅烷基、取代或未取代的芳香化合物及其芳香衍生物、取代或未取代的烷基、取代或未取代的硅烷基、取代或未取代的环烷基、取代或未取代的亚环烷基、取代或未取代的杂环烷基、取代或未取代的亚杂环烷基、取代或未取代的二环烷基、取代或未取代的三烷基甲硅烷基、取代或未取代的烯基、取代或未取代的亚烯基、取代或未取代的炔基、取代或未取代的亚炔基、取代或未取代的杂环脂基、取代或未取代的硫膦基、取代或未取代的氧膦基、取代或未取代的三嗪基、取代或未取代的三唑基、取代或未取代的吗啉基、取代或未取代的硫代吗啉基、取代或未取代的烷氧基、取代或未取代的亚烷氧基、取代或未取代的烷硫基、取代或未取代的亚烷硫基、取代或未取代的烷氨基、取代或未取代的苯磺酰基、取代或未取代的喹啉磺酰基、取代或未取代的苯甲酰基、取代或未取代的肼基、取代或未取代的酯基、取代或未取代的烷基羰基、取代或未取代的烷氧基羰基、取代或未取代的烷氨基羰基、取代或未取代的硅烷基羰基、取代或未取代的烷氧基硅烷、取代或未取代的烷硫基硅烷、取代或未取代的乙酰吡啶、取代或未取代的芴、取代或未取代的苝、取代或未取代的多环芳香族化合物、取代或未取代的咔唑、取代或未取代的噻吩、羟基、羧基或硝基;
其中,芳基表示由芳烃通过去除一个氢原子衍生物的有机基团,包括4、5、6、7元的单环或稠环;
杂芳基表示含1-4个选自N、O、S或Si的杂原子作为芳环骨架原子且其余芳环骨架原子为碳原子的芳基、二价芳基、5元或6元单杂环芳基或多环杂芳基;
Y1、Y2各自独立地为C或N。
进一步,X1、X2、X3、X4、X5、X6、X7、X8、X9任意相邻的两个基团连接形成环状基团。
更进一步,任意相邻的两个基团连接形成的环状基团包含一个或多个杂原子。
进一步,所述两个或多个化合物通过共价键连接。
进一步,所述两个或多个化合物通过X1、X2、X3、X4、X5、X6、X7、X8、X9基团连接。
进一步,所述两个或多个化合物通过-(Z)x-的桥基连接,所述Z为C、N、O、S、Se、CR2、NR3或AR4R5;x≥1,且为整数,x个Z相互独立;
其中,A为C、Si或Ge;R2、R3、R4、R5各自独立的为氢、氘、卤素、取代或未取代的芳基、取代或未取代的亚芳基、取代或未取代的亚杂芳基、取代或未取代的杂芳基、取代或未取代的苯并杂环芳基、取代或未取代的多环杂芳基、取代或未取代的苯并杂环脂基、取代或未取代的芳氨基、取代或未取代的芳硫基、取代或未取代的亚芳硫基、取代或未取代的芳醚基、取代或未取代的芳基烷基、取代或未取代的二烷基芳基甲硅烷基、取代或未取代的金刚烷、取代或未取代的三芳基甲硅烷基、取代或未取代的芳香化合物及其芳香衍生物、取代或未取代的烷基、取代或未取代的硅烷基、取代或未取代的环烷基、取代或未取代的亚环烷基、取代或未取代的杂环烷基、取代或未取代的亚杂环烷基、取代或未取代的二环烷基、取代或未取代的三烷基甲硅烷基、取代或未取代的烯基、取代或未取代的亚烯基、取代或未取代的炔基、取代或未取代的亚炔基、取代或未取代的杂环脂基、取代或未取代的硫膦基、取代或未取代的氧膦基、取代或未取代的三嗪基、取代或未取代的三唑基、取代或未取代的吗啉基、取代或未取代的硫代吗啉基、取代或未取代的烷氧基、取代或未取代的亚烷氧基、取代或未取代的烷硫基、取代或未取代的亚烷硫基、取代或未取代的烷氨基、取代或未取代的苯磺酰基、取代或未取代的喹啉磺酰基、取代或未取代的苯甲酰基、取代或未取代的肼基、取代或未取代的酯基、取代或未取代的烷基羰基、取代或未取代的烷氧基羰基、取代或未取代的烷氨基羰基、取代或未取代的硅烷基羰基、取代或未取代的烷氧基硅烷、取代或未取代的烷硫基硅烷、取代或未取代的乙酰吡啶、取代或未取代的芴、取代或未取代的苝、取代或未取代的多环芳香族化合物、取代或未取代的咔唑、取代或未取代的噻吩、羟基、羧基或硝基;
其中,芳基表示由芳烃通过去除一个氢原子衍生物的有机基团,包括4、5、6、7元的单环或稠环;
杂芳基表示含1-4个选自N、O、S或Si的杂原子作为芳环骨架原子且其余芳环骨架原子为碳原子的芳基、二价芳基、5元或6元单杂环芳基或多环杂芳基。
优选地,上述的氮杂芳香化合物,其结构式分别为:
本发明的第二个目的在于提供上述氮杂芳香化合物作为电致发光材料,在有机电致发光器件中的应用。
本发明的有益效果是:本发明提供一系列氮杂芳香化合物,作为荧光材料新的核心结构,制备出天蓝色的发光材料,这类有机化合物不仅发光效率高,而且还可以通过取代基和杂原子的位置来精细调节发射光的波长,此类材料可应用在电致发光器件中。
附图说明
图1为有机电致发光材料的OLED结构示意图;
图2为应用例1-3的发光光谱分析图;
图中,1、玻璃衬底;2、阳极层;3、空穴注入层;4、空穴传输层;5、发光层;6、电子传输层;7、电子注入层;8、阴极层。
具体实施方式
以下对本发明的原理和特征进行描述,所举实例只用于解释本发明,并非用于限定本发明的范围。
实施例1
化合物14的合成,反应方程式如下:
具体制备方法如下:
(1)在100mL三口瓶中,加入1-(3-溴苯基)-8甲基萘(R1a)1.31g(5mmol)、2-吡啶硼酸(Re2)1.48g(12mmol、碳酸钾1.76g(20mmol)、甲苯40g和去离子水15g,氮气保护,加入四三苯基膦钯0.1g,升温到65℃,回流18h,停止反应,降温,分液,收集有机相,脱去溶剂,得到中间体INT1a;
(2)在氮气保护下,将溴化锌(ZnBr2)1.11g(0.5mmol)、MnBr(CO)5 69.0mg(0.25mmol)、二氯乙烷(DCE)50mL、步骤(1)得到的INT1a、6-甲基-苯并呋喃-5-甲醛(R3a)1.6g(10mmol)、Me2Zn 7.5mL(7.5mmol)依次加入到250mL Schlenk瓶;然后升温至60℃,搅拌12h;用50mL乙酸乙酯稀释反应混合物并过滤,再将滤液浓缩后用硅胶柱过滤得到中间体INT2a;
(3)将步骤(2)得到的中间体INT2a加入到100mL三口瓶中,再加入20mL去离子水和HBr(48%,0.4mL,3.5mmol),升温到90℃,反应2h;真空蒸发溶剂,剩余固体加入甲醇溶解,进行结晶分离出固体;室温下加入少量水溶解固体至饱和状态,然后加入碳酸钠,得到浅黄色沉淀物Pa;通过重结晶对Pa粗品进行提纯,得化合物14。
实施例2
化合物23的合成,反应方程式如下:
具体制备方法如下:
与实施例1制备方法相同,区别在于步骤(1)中使用2-(3’-溴-1,1’-联苯基)萘(R1b)与2-吡啶硼酸(Re2)反应;在步骤(2)中,用1,1’-联苯基-4-甲醛(R3b)与INT1b反应;产物Pb为浅黄色固体,得化合物23。
实施例3
化合物29的合成,反应方程式如下:
具体制备方法如下:
与实施例1的制备方法步骤(2)(3)相同,区别在于步骤(1)中使用2-苯基吡啶(R1c)与4-苯并呋喃-4基-苯甲醛(R2c)反应生成INT1c;INT1c经过步骤(2)生成浅黄色固体产物Pc,得化合物29。
如图1所示,有机电致发光器件(OLED)的结构包括依次层叠结合的玻璃衬底1、阳极层2、空穴注入层3、空穴传输层4、发光层5、电子传输层6、电子注入层7和阴极层8。将本发明制得的氮杂芳香化合物应用在OLED的发光层中,表1为应用例1-3的OLED各层成分组成。
表1
应用例1
在玻璃底衬1上沉积一层厚度为100nm的氧化铟锡(ITO)作为透明阳极层2;在透明阳极层2上真空蒸镀厚度为10nm的NPB(N,N’-二(1-萘基)-N,N’-二苯基-1,1’-联苯-4-4’-二胺)空穴传输材料作为空穴注入层3,其中掺杂质量比3%的F4-TCNQ(2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌);空穴注入层3上为一层厚度为100nm的spiro-TAD(2,2',7,7'-四(二苯基氨基)-9,9'-螺双芴)作为空穴传输层4;在空穴传输层4上真空蒸镀一层厚度为40nm的BCP(4,4'-二(9-咔唑)联苯)作为发光层5,其中掺杂有4wt%的化合物14;再在发光层5上依次真空蒸镀一层厚度为30nm的TPQ(2,3,5,8-四苯基喹喔啉)作为电子传输层6、厚度为1nm的Liq作为电子注入层7,最后在电子注入层7上采用真空蒸镀膜沉积技术沉积厚度为100nm的金属铝(Al)作为器件的阴极层8。
经性能测试获知,该器件的电致发光光谱的最大发光波长位于467nm,最大电流效率为1.2cd/A,最大外量子效率为1.5%,CIEx=0.17和CIEy=0.33。
应用例2
与应用例1相同,与应用例1不同之处在于:发光层5为厚度30nm的单一材料发光层,其中发光材料为化合物23。
经性能测试获知,该器件的电致发光光谱的最大发光波长位于483nm,最大电流效率为1.5cd/A,最大外量子效率为1.8%,CIEx=0.10和CIEy=0.31。
应用例3
与应用例1相同,与应用例1不同之处在于:发光层5为厚度30nm的单一材料发光层,其中发光材料为化合物29。
经性能测试获知,该器件的电致发光光谱的最大发光波长位于476nm,最大电流效率为0.9cd/A,最大外量子效率为1.2%,CIEx=0.12和CIEy=0.26。
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (9)
1.一类用作蓝色荧光材料的氮杂芳香化合物,其特征在于,其结构式如下:
其中,X1、X2、X3、X4、X5、X6、X7、X8、X9各自独立的为N或CR1;
R1为氢、氘、卤素、取代或未取代的芳基、取代或未取代的亚芳基、取代或未取代的亚杂芳基、取代或未取代的杂芳基、取代或未取代的苯并杂环芳基、取代或未取代的多环杂芳基、取代或未取代的苯并杂环脂基、取代或未取代的芳氨基、取代或未取代的芳硫基、取代或未取代的亚芳硫基、取代或未取代的芳醚基、取代或未取代的芳基烷基、取代或未取代的二烷基芳基甲硅烷基、取代或未取代的金刚烷、取代或未取代的三芳基甲硅烷基、取代或未取代的芳香化合物及其芳香衍生物、取代或未取代的烷基、取代或未取代的硅烷基、取代或未取代的环烷基、取代或未取代的亚环烷基、取代或未取代的杂环烷基、取代或未取代的亚杂环烷基、取代或未取代的二环烷基、取代或未取代的三烷基甲硅烷基、取代或未取代的烯基、取代或未取代的亚烯基、取代或未取代的炔基、取代或未取代的亚炔基、取代或未取代的杂环脂基、取代或未取代的硫膦基、取代或未取代的氧膦基、取代或未取代的三嗪基、取代或未取代的三唑基、取代或未取代的吗啉基、取代或未取代的硫代吗啉基、取代或未取代的烷氧基、取代或未取代的亚烷氧基、取代或未取代的烷硫基、取代或未取代的亚烷硫基、取代或未取代的烷氨基、取代或未取代的苯磺酰基、取代或未取代的喹啉磺酰基、取代或未取代的苯甲酰基、取代或未取代的肼基、取代或未取代的酯基、取代或未取代的烷基羰基、取代或未取代的烷氧基羰基、取代或未取代的烷氨基羰基、取代或未取代的硅烷基羰基、取代或未取代的烷氧基硅烷、取代或未取代的烷硫基硅烷、取代或未取代的乙酰吡啶、取代或未取代的芴、取代或未取代的苝、取代或未取代的多环芳香族化合物、取代或未取代的咔唑、取代或未取代的噻吩、羟基、羧基或硝基;
Y1、Y2各自独立地为C或N。
2.根据权利要求1所述的氮杂芳香化合物,其特征在于,X1、X2、X3、X4、X5、X6、X7、X8、X9任意相邻的两个基团连接形成环状基团。
3.根据权利要求2所述的氮杂芳香化合物,其特征在于,任意相邻的两个基团连接形成的环状基团包含一个或多个杂原子。
4.根据权利要求1-3任一项所述的氮杂芳香化合物,其特征在于,所述两个或多个化合物通过共价键连接。
5.根据权利要求1-3任一项所述的氮杂芳香化合物,其特征在于,所述两个或多个化合物通过X1、X2、X3、X4、X5、X6、X7、X8、X9基团连接。
6.根据权利要求1-3任一项所述的氮杂芳香化合物,其特征在于,所述两个或多个化合物通过-(Z)x-的桥基连接,所述Z为C、N、O、S、Se、CR2、NR3或AR4R5;x≥1,且为整数,x个Z相互独立;
其中,A为C、Si或Ge;R2、R3、R4、R5各自独立的为氢、氘、卤素、取代或未取代的芳基、取代或未取代的亚芳基、取代或未取代的亚杂芳基、取代或未取代的杂芳基、取代或未取代的苯并杂环芳基、取代或未取代的多环杂芳基、取代或未取代的苯并杂环脂基、取代或未取代的芳氨基、取代或未取代的芳硫基、取代或未取代的亚芳硫基、取代或未取代的芳醚基、取代或未取代的芳基烷基、取代或未取代的二烷基芳基甲硅烷基、取代或未取代的金刚烷、取代或未取代的三芳基甲硅烷基、取代或未取代的芳香化合物及其芳香衍生物、取代或未取代的烷基、取代或未取代的硅烷基、取代或未取代的环烷基、取代或未取代的亚环烷基、取代或未取代的杂环烷基、取代或未取代的亚杂环烷基、取代或未取代的二环烷基、取代或未取代的三烷基甲硅烷基、取代或未取代的烯基、取代或未取代的亚烯基、取代或未取代的炔基、取代或未取代的亚炔基、取代或未取代的杂环脂基、取代或未取代的硫膦基、取代或未取代的氧膦基、取代或未取代的三嗪基、取代或未取代的三唑基、取代或未取代的吗啉基、取代或未取代的硫代吗啉基、取代或未取代的烷氧基、取代或未取代的亚烷氧基、取代或未取代的烷硫基、取代或未取代的亚烷硫基、取代或未取代的烷氨基、取代或未取代的苯磺酰基、取代或未取代的喹啉磺酰基、取代或未取代的苯甲酰基、取代或未取代的肼基、取代或未取代的酯基、取代或未取代的烷基羰基、取代或未取代的烷氧基羰基、取代或未取代的烷氨基羰基、取代或未取代的硅烷基羰基、取代或未取代的烷氧基硅烷、取代或未取代的烷硫基硅烷、取代或未取代的乙酰吡啶、取代或未取代的芴、取代或未取代的苝、取代或未取代的多环芳香族化合物、取代或未取代的咔唑、取代或未取代的噻吩、羟基、羧基或硝基。
7.根据权利要求1或6所述的氮杂芳香化合物,其特征在于,芳基表示由芳烃通过去除一个氢原子衍生物的有机基团,包括4、5、6、7元的单环或稠环;
杂芳基表示含1-4个选自N、O、S或S i的杂原子作为芳环骨架原子且其余芳环骨架原子为碳原子的芳基、二价芳基、5元或6元单杂环芳基或多环杂芳基。
8.根据权利要求1所述的氮杂芳香化合物,其特征在于,其结构式为:
9.一种权利要求1所述用作蓝色荧光材料的氮杂芳香化合物作为电致发光材料,在有机电致发光器件中的应用。
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