CN109553606B - 一种通式化合物及有机发光器件 - Google Patents
一种通式化合物及有机发光器件 Download PDFInfo
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- CN109553606B CN109553606B CN201710871417.9A CN201710871417A CN109553606B CN 109553606 B CN109553606 B CN 109553606B CN 201710871417 A CN201710871417 A CN 201710871417A CN 109553606 B CN109553606 B CN 109553606B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- -1 imino, methylene Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000004802 cyanophenyl group Chemical group 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract description 9
- 125000004122 cyclic group Chemical group 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 63
- 239000010410 layer Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 239000000463 material Substances 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 17
- 239000003208 petroleum Substances 0.000 description 16
- 239000007810 chemical reaction solvent Substances 0.000 description 15
- 239000012043 crude product Substances 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- IAJCAZVXGKGAQK-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC(Cl)=C(C#N)C(Cl)=N1 IAJCAZVXGKGAQK-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000001045 blue dye Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZTOFNRMEKUYYOE-UHFFFAOYSA-N 1-propan-2-yl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(C)C ZTOFNRMEKUYYOE-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 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 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000002346 layers by function Substances 0.000 description 4
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 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 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005309 thioalkoxy group Chemical group 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical class C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- STLFZKZBGXSIQJ-UHFFFAOYSA-N 1,1'-biphenyl;naphthalene Chemical group C1=CC=CC2=CC=CC=C21.C1=CC=CC=C1C1=CC=CC=C1 STLFZKZBGXSIQJ-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- ITFIPASQLAETLZ-UHFFFAOYSA-N 1-(2-bromophenyl)-2-methylnaphthalene Chemical compound CC1=CC=C2C=CC=CC2=C1C1=CC=CC=C1Br ITFIPASQLAETLZ-UHFFFAOYSA-N 0.000 description 1
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- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 1
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- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
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- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium 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
- 239000010406 cathode material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- IZWRXCGNSVOSAT-UHFFFAOYSA-L dichloronickel;diphenyl(propyl)phosphane Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 IZWRXCGNSVOSAT-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SDVJQGKADKSAPX-UHFFFAOYSA-M methoxymethyl(trimethyl)phosphanium;chloride Chemical compound [Cl-].COC[P+](C)(C)C SDVJQGKADKSAPX-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种下式表示的通式化合物:式(I)中:A4选自氰基或苯氰基;A1、A2和A3分别独立由下式(II)或式(III)表示:式(II)和式(III)中:R1‑R8和R9‑R16分别独立选自氢、C1~C10的烷基、C6~C30的取代或未取代的芳基或稠环芳烃基团、C3~C30的取代或未取代的杂芳基或稠杂环芳烃基团;且R1‑R8中任何相邻的两个任选地接成环状结构,R9‑R16中任何相邻的两个任选地接成环状结构;且当A1选自式(II)时,式(Ⅱ)中的R1和R8中至少一个为氢;当A1选自式(III)时,式(Ⅲ)中的R9和R16中至少一个为氢;式(III)中:X选自氧、硫、亚氨基、亚甲基、亚甲硅烷基中。本发明还涉及采用上述通式化合物的有机电致发光器件。
Description
技术领域
本发明涉及一种新型通式化合物,同时涉及一种采用该化合物的有机电致发光器件。
背景技术
有机电致发光显示器(以下简称OLED)具有自主发光、低电压直流驱动、全固化、视角宽、重量轻、组成和工艺简单等一系列的优点,与液晶显示器相比,有机电致发光显示器不需要背光源,视角大,功率低,其响应速度可达液晶显示器的1000倍,其制造成本却低于同等分辨率的液晶显示器,因此,有机电致发光器件具有广阔的应用前景。
随着OLED技术在照明和显示两大领域的不断推进,人们对于影响OLED器件性能的高效有机材料的研究更加关注,一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。
典型的OLED由玻璃基板、ITO、阳极、有机发光层与阴极等组成,其中发光材料是决定OLED发光效率的最要因素。第一类荧光材料,只能利用25%的单线态S1激子。第二类磷光材料,不仅可以利用25%的单线态S1激子,还能利用75%的三线态T1激子,所以理论内量子效率可达100%。但磷光材料一般包含例如Ir和Pt的稀有金属,材料成本较高且依赖于有限的全球资源。2011年,日本九州大学Adachi教授等人报道了一种新型的热激活延迟荧光材料(TADF)。TADF材料具有较小的能隙足以使三重态激子从T1逆向隙间窜越(RISC)转化为S1,再由S1态辐射衰减至基态S0,从而使TADF材料能够实现通过在S1处的电激发产生的100%激子形成。但目前这种材料仍然不多,开发新型高性能的TADF材料,特别是蓝光材料势在必行。
发明内容
为了克服以上现有技术中传统主体材料的缺点,本发明的提供本发明提供一类新型用于有机电致发光器件的化合物。
本发明的化合物由如下通式(Ⅰ)表示:
式(I)中:
A4选自氰基或苯氰基;
A1、A2和A3分别独立由下式(II)或式(III)表示:
式(II)和式(III)中:
R1-R8和R9-R16分别独立选自氢、C1~C10的烷基、C6~C30的取代或未取代的芳基或稠环芳烃基团、C3~C30的取代或未取代的杂芳基或稠杂环芳烃基团;
当R1-R8和R9-R16选自取代的芳基、稠环芳基、杂环芳基或稠杂环芳基基团时,所述其上的取代基团独立选自卤素、氰基、硝基,或选自C1~C10的烷基或环烷基、烯基、C1~C6的烷氧基或硫代烷氧基,或者独立选自具有4~20个环碳原子的单环或稠环芳基、含有选自N、O、S、Si的杂原子且具有4~20个环碳原子的单环或稠环芳基;
且R1-R8中任何相邻的两个任选地接成环状结构,R9-R16中任何相邻的两个任选地接成环状结构;
且当A1选自式(II)时,式(Ⅱ)中的R1和R8中至少一个为氢,此时,另一个与嘧啶环上的氮原子会形成分子内氢键。
当A1选自式(III)时,式(Ⅲ)中的R9和R16中至少一个为氢,此时另一个与含N杂环上的氮原子形成分子内氢键。
式(III)中:
X选自氧、硫、亚氨基、亚甲基、亚甲硅烷基中。
具体说,当定义上述R1-R8和R9-R16分别独立选自芳基或亚芳基时,是指选自具有一定数目环骨架碳原子的芳族环系,包括单环结构取代基团例如苯基等,也包括共价连接结构的芳环取代基团例如联苯基、三联苯基等。
具体说,当定义上述R1-R8和R9-R16分别独立选自稠环芳烃或亚稠环芳烃基团时是指具有一定数目环骨架碳原子的芳族环系,包括稠环结构取代基团例如萘基、蒽基等,也包括稠环结构取代基团与单环结构芳基相连接的结构基团例如苯联萘基、萘联苯基、联苯联蒽基等,还包括共价连接结构的稠芳环取代基团例如联萘基等。
具体说,当定义上述R1-R8和R9-R16分别独立选自杂芳基或稠杂环芳烃基团时是指包含一个或多个选自B、N、O、S、P(=O)、Si和P的杂原子且具有环碳原子的单环或稠环芳基。
进一步的,式(I)中,R1-R8和R9-R16分别独立优选自氢、C1~C8的烷基、C6~C15的取代或未取代的芳基或稠环芳烃基团、C3~C15的取代或未取代的杂芳基或稠杂环芳烃基团;
当R1-R8和R9-R16选自取代的芳基、稠环芳基、杂环芳基或稠杂环芳基基团时,所述其上的取代基团独立优选自F、氰基,或选自C1~C10的烷基或环烷基、烯基、烷氧基或硫代烷氧基基团,或者独立选自具有4~15个环碳原子的单环或稠环芳基、含有选自N、O、S杂原子且具有4~15个环碳原子的单环或稠环芳基。
更进一步的,式(I)中,R1-R8和R9-R16分别独立优选自下述基团:氢、甲基、乙基、异丙基、叔丁基、环戊基、环己基、氰基、硝基、苯基、联苯基、三联苯基、萘基、三亚苯基、蒽基、菲基、茚基、荧蒽基、9,9二甲基芴、螺二芴基、呋喃基、苯基呋喃基、噻吩基、苯基噻吩基、吡咯基、苯基吡咯基、吡啶基、苯基吡啶基、吡嗪基、芴基、茚并芴基、喹啉、三嗪基、苯并呋喃基、苯并噻吩基、苯并三嗪、苯并吡嗪、异苯并呋喃基、吲哚基、苯并喹啉、二苯并呋喃基、二苯并噻吩基、二苯并吡咯基、咔唑基及其衍生物、苯基取代的二唑、啡啉基、啡啉并噻唑基和苯并间二氧杂环戊烯基中的至少一种,其中,所述咔唑基衍生物可以包括但不限于9-苯基咔唑、9-萘基咔唑苯并咔唑、二苯并咔唑、和吲哚并咔唑中的至少一种。
更进一步的,式(I)中,A1、A2和A3分别独立由下式(II-1)或式(III-1)表示:
式(II-1)和式(III-1)中:
R3、R6和R11、R14与通式(Ⅰ)中的定义相同且不为氢;X与通式(Ⅰ)中的定义相同。
本发明的化合物均满足最低单重态S1与最低三重态T1之间的能极差△EST=ES1-ET1≤0.50eV。
进一步优选为化合物最低单重态S1与最低三重态T1之间的能极差△EST=ES1-ET1≤0.30eV。
最优选为化合物最低单重态S1与最低三重态T1之间的能极差△EST=ES1-ET1≤0.10eV。
上述Ca~Cb的表达方式代表该基团具有的碳原子数为a~b,除非特殊说明,一般而言该碳原子数不包括取代基的碳原子数。
上述对于化学元素的表述包含化学性质相同的同位素的概念,例如“氢”的表述,也包括化学性质相同的“氘”、“氚”的概念。
在本发明的一个优选实施方式中,出于成膜性能以及加工性能方面的考虑,所述化合物的分子量介于400~1200之间,优选为450~1100之间。
更进一步的,结合本发明的通式可以优选出下述具体结构化合物:P1~P42,这些化合物仅为代表性的:
本发明还提供了上述有机电致发光化合物在制备有机电致发光器件中的用途。有机电致发光器件一般包括第一电极、第二电极和位于所述第一电极和第二电极之间的一层或多层有机功能层,作为第一电极和第二电极之间的有机层,通常有电子注入层、电子传输层、发光层、空穴传输层、空穴注入层等有机层。本发明的化合物可以用作但不限于发光主体材料。
本发明还提供了一种有机电致发光器件,该器件包括第一电极、第二电极和位于所述第一电极和第二电极之间的一层或多层有机层,所述有机层中包括至少一种由通式(Ⅰ)表示的化合物:
式(I)中:
A4选自氰基或苯氰基;
A1、A2和A3分别独立由下式(II)或式(III)表示:
式(II)和式(III)中:
R1-R8和R9-R16分别独立选自氢、C1~C10的烷基、C6~C30的取代或未取代的芳基或稠环芳烃基团、C3~C30的取代或未取代的杂芳基或稠杂环芳烃基团;
当R1-R8和R9-R16选自取代的芳基、稠环芳基、杂环芳基或稠杂环芳基基团时,所述其上的取代基团独立选自卤素、氰基、硝基,或选自C1~C10的烷基或环烷基、烯基、C1~C6的烷氧基或硫代烷氧基,或者独立选自具有4~20个环碳原子的单环或稠环芳基、含有选自N、O、S、Si的杂原子且具有4~20个环碳原子的单环或稠环芳基;
且R1-R8中任何相邻的两个任选地接成环状结构,R9-R16中任何相邻的两个任选地接成环状结构;
且当A1选自式(II)时,式(Ⅱ)中的R1和R8中至少一个为氢;当A1选自式(III)时,式(Ⅲ)中的R9和R16中至少一个为氢;
式(III)中:
X选自氧、硫、亚氨基、亚甲基、亚甲硅烷基中。
本发明还提供了一种有机电致发光器件,该器件包括第一电极、第二电极和位于所述第一电极和第二电极之间的一层或多层有机层,所述有机层中包括至少一种下述具体结构化合物:
本发明的新型通式化合物的优点在于:
本发明的化合物结构设计选用嘧啶结构作为母核基团,分别引入咔唑和氰基基团作为电子给体和受体,从而形成D-π-A结构,化合物具有较小的△Est有利于三线态能量的应用。其嘧啶上的氮原子与通式上的A1所选择的式(II)或式(III)结构上的氢原子相邻,由于N的电负性大,共用电子对强烈偏向N原子一边,而H原子核外只有一个电子,其电子云向N原子偏移的结果,使得它几乎要呈质子状态,从而形成分子内氢键,形成如下图所示的六元环结构,这种结构由于形成六元环结构,提高化合物的平面性,从而抑制分子内转动,减小了材料发光光谱的半峰宽,有利于显示应用。同时,由于基团与母核间的近平面结构,大的共轭结构有利于提高载流子迁移率,使得激子复合区域扩展,从而提高器件效率。
因此,本发明的采用该通式化合物的有机电致发光器件具备较好的技术效果,具有更高的电流效率和内量子效率。
附图说明
从下面结合附图对本发明实施例的详细描述中,本发明的这些和/或其它方面和优点将变得更加清楚并更容易理解,其中:
图1为本发明化合物P1的最高已占分子轨道(HOMO)能级图;
图2为本发明化合物P1的最低未占分子轨道(LUMO)能级图。
具体实施方式
为了使本领域技术人员更好地理解本发明,下面结合附图和具体实施方式对本发明作进一步详细说明。
本发明中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。实施例中所用的各种化学药品如石油醚、乙酸乙酯、正己烷、甲苯、四氢呋喃、二氯甲烷、四氯化碳、丙酮、1,2-双(溴甲基)苯、CuI、邻苯二甲酰氯、盐酸苯肼、三氟乙酸、乙酸、反式-二氨基环己烷、碘苯、碳酸铯、磷酸钾、乙二胺、二苯甲酮、环戊酮、9-芴酮、叔丁醇钠、甲烷磺酸、1-溴-2-甲基萘、邻二溴苯、丁基锂、二溴乙烷、邻二溴苯、过氧化苯甲酰、1-(2-溴苯基)-2-甲基萘、N-溴代丁二酰亚胺、甲氧甲基三甲基氯化鏻、三(二亚苄基丙酮)二钯、四(三苯基膦)钯、1,3-双二苯基膦丙烷氯化镍、咔唑、3,6-二叔丁基咔唑、、N-苯基咔唑-3-溴、2-溴芴酮、2-(4-溴苯)-4,6-二苯基三嗪等基础化工原料均可在国内化工产品市场买到。
本发明中的中间体和化合物的分析检测使用ABSCIEX质谱仪(4000QTRAP)和布鲁克核磁共振仪(400M)。
化合物的合成实施例:
本发明中的所有化合物均按以下合成路线获得,在合成路线中Ar代表Ar1,Ar2或Ar3,并且Ar1,Ar2或Ar3的定义如前:
将35mmol的Ar加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将30mmol的NaH分批加入到反应瓶中,继续搅拌1h。将10mmol的2,4,6-三氯-5-氰基嘧啶或2,4,6-三氯-5-氰苯基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷为流动相过柱子。
下面以化合物P1,P2,P5,P9,P10,P11,P12,P21,P34,P36和P42的合成实施例详细说明化合物的合成方案。
合成例1:化合物P1的合成
将8.79g(35mmol)异丙基咔唑加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末5.56g,产率为65.2%。(1HNMR(δ,CDCl3):7.40(6H,s),7.28(6H,s),6.71-6.68(6H,d),3.08-3.01(6H,m),1.19-1.10(12H,m),MS:(852.4)
合成例2:化合物P2的合成
将8.79g(35mmol)异丙基咔唑加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.83g(10mmol)2,4,6-三氯-5-氰苯基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末4.99g,产率为53.7%。
(1HNMR(δ,CDCl3):7.60-7.56(4H,d),7.38(6H,s),7.30(6H,s),6.66-6.60(6H,d),3.13-3.08(6H,m),1.25-1.16(12H,m),MS:(928.4)
合成例3:化合物P5的合成
在氮气保护下,将6.28g(25mmol)异丙基咔唑,2.83g(10mmol)2,4,6-三氯-5-氰基嘧啶,1.92g(20mmol)NaOBu-t,1.92g(0.2mmol)(t-Bu)3HBF4,0.09g(0.1mmol)Pd2(dba)3加入到250ml的三口瓶中,加入100ml甲苯作为反应溶剂,升温至回流温度,在磁力搅拌器上搅拌过夜。反应结束后,将反应液旋干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=5:1)为流动相过柱子。得到中间体1,为白色固体粉末,重4.70g,产率为73.7%。
将1.56g(7.5mmol)9,9-二甲基吖啶加入到250ml的三口瓶中,加入50ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.36g(15mmol)NaH分批加入到反应瓶中,继续搅拌1h。将3.19g(5mmol)中间体1溶解在20ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入100ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末2.79g,产率为68.9%。
(1HNMR(δ,CDCl3):7.44(4H,s),7.34(4H,s),6.92-6.85(8H,t),6.50-6.40(4H,d),3.14-3.06(4H,m),1.52-1.34(10H,m),MS:(810.5)
合成例4:化合物P9的合成
将7.32g(35mmol)9,9-二甲基吖啶加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末4.29g,产率为59.1%。(1HNMR(δ,CDCl3):6.90-6.80(12H,d),6.56-6.44(12H,d),1.71-1.65(6H,m),MS:(726.4)
合成例5:化合物P10的合成
将6.37g(35mmol)吩噁嗪加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末3.91g,产率为60.3%。(1HNMR(δ,CDCl3):6.75-6.68(12H,d),6.56-6.46(12H,m),MS:(648.2)
合成例6:化合物P11的合成
将7.84g(35mmol)10,10-二甲基-二苯基并苯基硅氧烷加入到250ml的三口瓶中,加入100mlN,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末3.94g,产率为50.9%。(1HNMR(δ,CDCl3):7.31(6H,s),7.09(6H,s),6.71-6.64(12H,d)0.85-0.70(6H,m),MS:(774.4)
合成例7化合物P12合成
将9.00g(35mmol)10-苯基酚嗪加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末4.87g,产率为55.8%。
(1HNMR(δ,CDCl3):7.03(6H,s),6.64(3H,s),6.42-6.36(18H,m),6.61-6.58(12H,m),MS:(818.5)
合成例8:化合物P21的合成
在氮气保护下,将2.08g(10mmol)9,9-二甲基吖啶,2.83g(10mmol)2,4,6-三氯-5-氰苯基嘧啶,2.76g(20mmol)K2CO3,0.12g(0.1mmol)Pd(PPh3)4加入到250ml的三口瓶中,加入100ml甲苯作为反应溶剂,升温至回流温度,在磁力搅拌器上搅拌过夜。反应结束后,将反应液旋干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=5:1)为流动相过柱子。得到中间体2,为白色固体粉末,重2.77g,产率为60.7%。
在氮气保护下,将2.73g(15mmol)吩噁嗪,2.83g(10mmol)2,4,6-三氯-5-氰基嘧啶,1.92g(20mmol)NaOBu-t,1.92g(0.2mmol)(t-Bu)3HBF4,0.09g(0.1mmol)Pd2(dba)3加入到250ml的三口瓶中,加入100ml甲苯作为反应溶剂,升温至回流温度,在磁力搅拌器上搅拌过夜。反应结束后,将反应液旋干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=5:1)为流动相过柱子。得到中间体3,为白色固体粉末,重3.37g,产率为55.8%。
将1.89g(7.5mmol)异丙基咔唑加入到250ml的三口瓶中,加入50ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.36g(15mmol)NaH分批加入到反应瓶中,继续搅拌1h。将3.02g(5mmol)中间体3溶解在20ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入100ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末2.60g,产率为63.5%。(1HNMR(δ,CDCl3):7.46-7.43(4H,d),7.28-7.24(4H,d),6.89-6.81(8H,m),6.63-6.52(10H,m),3.09(2H,s),1.42-1.26(6H,m),MS:(852.4)
合成例9:化合物P34的合成
将11.17g(35mmol)3,6-二苯基咔唑加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末5.31g,产率为50.3%。
(1HNMR(δ,CDCl3):7.72(6H,s),7.44-7.40(18H,m),7.36-7.22(24H,m),MS:(1056.7)
合成例10:化合物P36的合成
将6.93g(35mmol)噻噁嗪加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将2.07g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末4.64g,产率为66.7%。(1HNMR(δ,CDCl3):7.01-6.97(12H,d),6.72-6.66(12H,m),MS:(696.1)
合成例11:化合物P42的合成
将8.79g(35mmol)异丙基咔唑加入到250ml的三口瓶中,加入100ml N,N-二甲基甲酰胺作为反应溶剂,在冰浴条件下,在磁力搅拌器上搅拌10min。将0.72g(30mmol)NaH分批加入到反应瓶中,继续搅拌1h。将4.97g(10mmol)2,4,6-三氯-5-氰基嘧啶溶解在40ml的N,N-二甲基甲酰胺溶液里,逐滴加入到反应体系中,添加完毕后,在室温下反应24h。反应结束后,将反应液倒入200ml浓度为10%的稀盐酸中淬灭,减压抽滤后,水洗,烘干,得到的粗产品用石油醚和二氯甲烷(PE:DCM=10:1)为流动相过柱子。得到白色固体粉末7.98g,产率为50.2%。(1HNMR(δ,CDCl3):7.58-7.55(18H,m),7.44-7.38(18H,m),7.12-7.01(30H,m),MS:(1590.56)
以下对本发明的有机电致发光器件的发光层和有机电致发光器件进行说明。
本发明的有机电致发光器件的发光层,包括主体材料和染料:所述的染料采用本发明中的嘧啶类化合物和TCzCN,所述的主体材料选用DPEPO。
本发明的有机电致发光器件,包括基板,以及依次形成在所述基板上的阳极层、多个发光功能层和阴极层;
所述的发光功能层包括空穴注入层、空穴传输层、发光层、电子传输层,所述的空穴注入层形成在所述的阳极层上,所述的空穴传输层形成在所述的空穴注入层上,所述的阴极层形成在所述的电子传输层上,所述的空穴传输层与所述的电子传输层之间为发光层;所述的发光层为上述本发明的有机电致发光器件的发光层。
OLED有机电致发光器件的典型结构为:
基片/阳极/空穴传输层(HTL)/有机发光层(EL)/电子传输层(ETL)/阴极
上述“/”表示不同功能层之间按顺序层叠。
基片可以使用传统有机发光有机电致发光器件中的基板,例如:玻璃或塑料。阳极材料可以采用透明的高导电性材料,例如铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等。在实施例的有机电致发光器件制作中选用玻璃基板,ITO作阳极材料。
空穴传输层采用N,N’-二(3-甲苯基)-N,N’-二苯基-[1,1-联苯基]-4,4’-二胺(TPD)或N,N’-二苯基-N,N’-二(1-萘基)-(1,1’-联苯基)-4,4’-二胺(NPB)等三芳胺类材料。其中NPB是常用的空穴传输材料,在实施例的有机电致发光器件制作中所选用的空穴传输材料选用NPB。
有机电致发光器件结构可以为单发光层也可以是多发光层结构。本发明实施例中采用了单发光层的结构。
电子传输层采用Alq3或者TAZ或者TPBi或者取自这三种材料的任意两种的搭配。
在本发明实施例的有机电致发光器件制作中选用阴极材料是LiF/Al。
本发明中使用的几种材料具体结构见下:
实施例:制作有机光电装置
本发明的化合物作为蓝色荧光OLED有机电致发光器件中的蓝光染料:
共制备12个有机电致发光器件((实施例1-11和对比实施例))。有机电致发光器件结构是在基片上,按照“阳极/空穴传输层(HTL)/有机发光层(EL)/电子传输层(ETL)/阴极”的顺序层叠,各层由以下材料构成:
ITO(100nm)/NPB(40nm)/DPEPO(30nm):蓝光染料[5%]/Alq3(20nm)/LiF(0.5nm)/Al(100nm)。
对比实施例中蓝光染料选用TBPe,其余实施例中蓝光染料选用本发明中的化合物。
本发明中有机电致发光器件的制备过程如下:将具有膜后为100nm的ITO薄膜的阳极基板用蒸馏水、丙酮、异丙酮在超声中清洗并放入烘箱中干燥,使用紫外光和臭氧处理表面30min,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;
在空穴传输层之上真空蒸镀“DPEPO:蓝光染料[5%]”的材料作为有机电致发光器件的发光层,蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;其中“蓝光染料[5%]”是指蓝光染料的掺杂比例,即DPEPO与蓝光染料的重量份比为100:5。
在发光层之上真空蒸镀Alq3作为有机电致发光器件的电子传输层,其蒸镀速率为0.1nm/s,蒸镀总膜厚为20nm;
在电子传输层上真空蒸镀0.5nm的LiF,Al 100nm的Al作为阴极。
对所得有机电致发光器件在相同亮度下测定驱动电压和电流效率,性能见表1。
表1
由上表可以看到,在荧光发光层中,发光染料采用本发明化合物的有机电致发光器件相对于染料TCzCN的有机电致发光器件获得了较好的效果,获得了更高的电流效率、内量子效率。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合,为了避免不必要的重复,本发明对各种可能的组合方式不再另行说明。
此外,本发明的各种不同的实施方式之间也可以进行任意组合,只要其不违背本发明的思想,其同样应当视为本发明所公开的内容。
Claims (6)
1.一种化合物由通式(Ⅰ)表示:
式(I)中:
A4选自氰基或氰基苯基;
A1、A2和A3分别独立由下式(II-1)或式(III)表示:
式(II-1)和式(III)中:
R3、R6分别独立选自C1~C8的烷基、C6~C15的取代或未取代的芳基或稠环芳烃基团、C3~C15的取代或未取代的杂芳基或稠杂环芳烃基团,R9-R16分别独立选自氢、C1~C8的烷基、C6~C15的取代或未取代的芳基或稠环芳烃基团、C3~C15的取代或未取代的杂芳基或稠杂环芳烃基团;
当R3、R6和R9-R16选自取代的芳基、稠环芳基、杂环芳基或稠杂环芳基基团时,所述其上的取代基团独立选自C1~C10的烷基;
当A1选自式(III)时,式(Ⅲ)中的R9和R16中至少一个为氢;
式(III)中:
X选自氧、硫、亚氨基、亚甲基、亚甲硅烷基中。
4.根据权利要求1或2所述的通式化合物在有机电致发光器件中的应用。
5.根据权利要求3所述的结构化合物在有机电致发光器件中的应用。
6.一种有机电致发光器件,该器件包括第一电极、第二电极和位于所述第一电极和第二电极之间的一层或多层有机层,其特征在于,所述有机层中包括至少一种由通式(Ⅰ)表示的化合物:
式(I)中:
A4选自氰基或氰基苯基;
A1、A2和A3分别独立由下式(II-1)或式(III)表示:
式(II-1)和式(III)中:
R3、R6分别独立选自C1~C8的烷基、C6~C15的取代或未取代的芳基或稠环芳烃基团、C3~C15的取代或未取代的杂芳基或稠杂环芳烃基团,R9-R16分别独立选自氢、C1~C8的烷基、C6~C15的取代或未取代的芳基或稠环芳烃基团、C3~C15的取代或未取代的杂芳基或稠杂环芳烃基团;
当R3、R6和R9-R16选自取代的芳基、稠环芳基、杂环芳基或稠杂环芳基基团时,所述其上的取代基团独立选自C1~C10的烷基;
当A1选自式(III)时,式(Ⅲ)中的R9和R16中至少一个为氢;
式(III)中:
X选自氧、硫、亚氨基、亚甲基、亚甲硅烷基中。
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