CN102459149A - 胺衍生物及有机电致发光器件 - Google Patents
胺衍生物及有机电致发光器件 Download PDFInfo
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- CN102459149A CN102459149A CN2010800247485A CN201080024748A CN102459149A CN 102459149 A CN102459149 A CN 102459149A CN 2010800247485 A CN2010800247485 A CN 2010800247485A CN 201080024748 A CN201080024748 A CN 201080024748A CN 102459149 A CN102459149 A CN 102459149A
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- China
- Prior art keywords
- carbonatoms
- sulfonamide derivatives
- cyclic
- aryl
- heteroaryl
- Prior art date
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- Granted
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- 150000001412 amines Chemical class 0.000 title abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 238000000859 sublimation Methods 0.000 claims abstract description 12
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 150000003456 sulfonamides Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 17
- 230000008021 deposition Effects 0.000 claims description 13
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 11
- 230000005540 biological transmission Effects 0.000 claims description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 9
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000005401 electroluminescence Methods 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 38
- 230000008022 sublimation Effects 0.000 abstract description 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 22
- 239000000126 substance Substances 0.000 description 21
- 239000010410 layer Substances 0.000 description 20
- -1 benzo fluorenyl Chemical group 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000000434 field desorption mass spectrometry Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000000565 sulfonamide group Chemical class 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 235000002597 Solanum melongena Nutrition 0.000 description 4
- 244000061458 Solanum melongena Species 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 238000005576 amination reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 239000002305 electric material Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 230000005477 standard model Effects 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- VUIOUIWZVKVFCI-UHFFFAOYSA-N 1-(2-hydroxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(O)C=CC2=C1 VUIOUIWZVKVFCI-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 1
- ZMCQQCBOZIGNRV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(1,2,4-triazol-1-yl)ethyl]benzamide Chemical compound NCC1=CC(OC2=CC=CC(=C2)C(=O)NCCN2C=NC=N2)=NC(=C1)C(F)(F)F ZMCQQCBOZIGNRV-UHFFFAOYSA-N 0.000 description 1
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- LJHFUFVRZNYVMK-CYBMUJFWSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)O LJHFUFVRZNYVMK-CYBMUJFWSA-N 0.000 description 1
- XCGGCPJWVDAUJX-UHFFFAOYSA-N [O].C(CCCC)OC(CCCCCCCCCCCCCCCCC)OCCCCCC Chemical compound [O].C(CCCC)OC(CCCCCCCCCCCCCCCCC)OCCCCCC XCGGCPJWVDAUJX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000003851 azoles Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- 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
- 238000000059 patterning Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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
- C07C211/57—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
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Abstract
本发明提供一种由通式(1)表示、且[分解温度(℃)-升华温度(℃)]的值为30℃以上的胺衍生物(式中,R1、R2独立地表示可以具有取代基的C6-14芳基或可以具有取代基的C5-40杂芳基。R3、R4独立地表示氢原子、直链、支链或环状的C1-18烷基、直链、支链或环状的C1-18烷氧基、可以具有取代基的C6-40芳基或可以具有取代基的C5-40杂芳基。R3和R4也可以成为一体从而形成环状基)。上述胺衍生物可用作有机EL用材料。
Description
技术领域
本发明涉及一种苯并芴基取代的新的胺衍生物以及利用所述衍生物的有机电致发光(EL)器件。
本发明中的新的苯并芴衍生物可以用作感光材料、有机光导电材料,具体而言,其作为被用于平面光源或显示器的有机EL器件或者电子照相感光体等的空穴传输材料、空穴注入材料及发光材料有用。
背景技术
目前正在积极地进行有机EL器件作为下一代薄型平面显示器的研究,一部分已经开始在手机的次屏幕等中实用化。一般来说,有机EL器件在阳极和阴极之间具有层叠有空穴传输材料、发光材料及电子传输材料的结构,但现在,为了实现上述低功耗化以及长寿命化,在阳极和空穴传输材料之间插入空穴注入材料、并且在阴极和电子传输材料之间插入电子注入材料的结构已成为主流。
作为空穴传输材料,已知有例如:4,4’-二[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)、N,N,N’,N’-四((1,1’-联苯)-4-基)联苯胺(TBDB)等具有二胺结构的三芳基胺衍生物(例如,参考非专利文献1、2),但近年来要求开发用于使有机EL器件进一步高效率化和长寿命化的新材料。
另一方面,提出了具有苯并芴骨架的有机电致发光材料(例如,参考专利文献1)。但没有在苯并芴基上直接键合有氨基的化合物的记载,而且,虽然有特别是具有苯并芴基的聚合物材料用作发光材料的记载,但没有其用作空穴传输材料及空穴注入材料的记载。
作为具有苯并芴基的胺化合物,虽然公知有具有各种结构的物质(例如,参考专利文献2、3),但没有本发明的后述通式(1)所表示的胺衍生物的记载,另外,关于利用真空蒸镀法制造有机EL器件时重要的加工特性也丝毫没有提及。
现有技术文献
专利文献
专利文献1:国际公开第2004/61048号小册子(权利要求书)
专利文献2:日本特开2008-50337公报(权利要求书)
专利文献3:日本特开2008-201769公报(权利要求书)
非专利文献
非专利文献1:“先进材料(Advanced Materials)”,(德国),1998年,第10卷,第14号,p1108-1112(图1、表1)
非专利文献2:“发光杂志(Journal of Luminescence)”,(荷兰),1997年,72-74,p985-991(图1)
发明内容
发明所要解决的问题
本发明的目的在于提供一种新的有机EL用材料,其与现有的有机EL用材料相比,在显示高功率效率的同时具有良好的耐久性,适合采用真空蒸镀法等成型。更详细而言,其目的在于提供一种特定的苯并芴基取代的新的胺衍生物,其适用于有机EL器件等的空穴注入材料、空穴传输材料及发光材料。
进而,本发明另一目的在于提供一种有机EL器件,其具有由上述胺衍生物形成的发光层、空穴传输层及空穴注入层中的任意一层。
用于解决问题的方法
本发明人进行了深入研究,结果发现,与现有公知的有机EL用化合物相比,通式(1)所表示的特定的胺衍生物在功率效率高及寿命长的方面非常优良,而且,其在制作有机EL器件时的加工耐久性优良,从而完成了本发明。
本发明提供一种由下述通式(1)表示、且[分解温度(℃)-升华温度(℃)]的值为30℃以上的胺衍生物。
式中,R1及R2可以相同也可以不同,表示可以具有取代基的碳原子数6~40的芳基或可以具有取代基的碳原子数5~40的杂芳基。R3及R4可以相同也可以不同,表示氢原子、碳原子数1~18的直链、支链或环状的烷基、碳原子数1~18的直链、支链或环状的烷氧基、可以具有取代基的碳原子数6~40的芳基或可以具有取代基的碳原子数5~40的杂芳基。其中,R3及R4也可以与两者所键合的苯并芴骨架中的碳原子一起形成碳原子数3~8的环状烃基。
而且,本发明提供一种有机电致发光器件,其特征在于,具备由上述胺衍生物形成的发光层、空穴传输层及空穴注入层中的任意一层以上。
而且,本发明提供一种有机电致发光器件的制造方法,其特征在于,利用真空蒸镀法将上述胺衍生物制成薄膜,形成发光层、空穴传输层及空穴注入层中的任意一层以上。
发明效果
本发明的通式(1)所表示的胺衍生物与现有的材料相比,可以在低电压下驱动,显示出高的功率效率。因此,可以作为有机EL器件或电子照相感光体等的空穴注入材料、空穴传输材料或发光材料来利用。
具体实施方式
下面,对本发明进行详细说明。
在表示本发明的胺衍生物的通式(1)中,R1及R2可以相同也可以不同,各自独立地表示可以具有取代基的碳原子数6~40的芳基或可以具有取代基的碳原子数5~40的杂芳基。
作为碳原子数6~40的芳基的具体例子,可以列举:苯基、萘基、联苯基、蒽基、芴基、菲基、芘基、基、苝基、苉基、苯并[a]芴基、苯并[b]芴基、苯并[c]芴基等,但不限定于此。需要说明的是,这些芳基也可以具有取代基。考虑到胺衍生物的利用真空蒸镀法的成型稳定性,优选可以具有取代基的碳原子数6~18的芳基。
碳原子数5~40的杂芳基为含有选自氧原子、氮原子及硫原子中的至少一个杂原子的芳香环基,可以列举例如:喹啉基、吡啶基、呋喃基、噻吩基、唑基、噻唑基、苯并唑基、苯并咪唑基等多环基,但不限定于此。需要说明的是,关于这些杂芳基,也可以与上述芳基一样具有取代基。考虑到胺衍生物的利用真空蒸镀法的成型稳定性,优选可以具有取代基的碳原子数5~18的杂芳基。
上述通式(1)所表示的胺衍生物中的R3及R4各自独立地表示氢原子、碳原子数1~18的直链、支链或环状的烷基、碳原子数1~18的直链、支链或环状的烷氧基、可以具有取代基的碳原子数6~40的芳基或可以具有取代基的碳原子数5~40的杂芳基。其中,R3及R4也可以与两者所键合的苯并芴骨架中的碳原子一起形成碳原子数3~8的环状烃基。
作为碳原子数1~18的直链、支链或环状的烷基的具体例子,可以列举:甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、十八烷基、三氯甲基、三氟甲基、环丙基、环己基、1,3-环己二烯基、2-环戊烯-1-基等。考虑到胺衍生物的利用真空蒸镀法的成型稳定性,优选可以具有取代基的碳原子数1~6的烷基。
作为碳原子数1~18的直链、支链或环状的烷氧基的具体例子,可以列举:甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、己氧基、十八烷氧基、三氟甲氧基等。考虑到胺衍生物的利用真空蒸镀法的成型稳定性,优选可以具有取代基的碳原子数1~6的烷氧基。
另外,作为碳原子数6~40的芳基或碳原子数5~40的杂芳基,可以从与上述R1、R2基团相同的基团中选择。考虑到胺衍生物的利用真空蒸镀法的成型稳定性,优选可以具有取代基的碳原子数6~18的芳基或可以具有取代基的碳原子数5~18的杂芳基。
R3及R4也可以与两者所键合的苯并芴骨架中的碳原子一起形成碳原子数3~8的环状烃基。作为该环状烃基的优选例子,可以列举碳原子数3~8的环烷基,例如环戊基及环己基。
作为R1、R2、R3及R4可以具有的取代基的优选的具体例子,可以列举:卤素原子、碳原子数1~10的直链、支链或环状的烷基及碳原子数1~10的直链、支链或环状的烷氧基。
以下例示出优选的胺衍生物,但其不限定于这些化合物。
本发明的通式(1)所表示的胺衍生物,例如可以依据公知的方法进行合成(例如,参考非专利文献3)。
非专利文献3:Tetrahedron Letters(四面体通讯),1998年,第39卷,2367页(胺化反应)
作为代表性的合成方法,例示有使下述通式(2)所表示的卤代苯并芴衍生物(式中,X表示卤素原子)和下述通式(3)所表示的仲胺发生胺化反应的方法。
通过进行层析、重结晶及升华提纯等提纯操作,合成的胺衍生物的纯度可以达到99.9%以上。特别是在要求高纯度品的情况下,优选使用升华提纯,但化合物的升华温度和分解温度接近时,在升华提纯中化合物本身的分解也在进行,因此难以得到高纯度品。另外,在利用真空蒸镀法使化合物形成有机EL器件的薄膜层的情况下,为了抑制化合物的分解,也需要升华温度与分解温度有一定程度的差别,优选[分解温度(℃)-升华温度(℃)]的值(即,升华温度(℃)与分解温度(℃)之差)为30℃以上,从能够进行稳定的升华提纯的观点出发,更优选该差值为50℃以上。
就本发明的胺衍生物而言,优选[LUMO(eV)-HOMO(eV)]的值(即,HOMO(eV)与LUMO(eV)的差)为3.0(eV)以上。其中,HOMO及LUMO表示在前线轨道理论中,被电子所占有的分子轨道中能级最高的轨道(最高已占轨道,Highest Occupied Molecular Orbital,简称为HOMO)和没有被电子占有的分子轨道中能级最低的轨道(最低未占轨道,Lowest Unoccupied Molecular Orbital,简称为LUMO)中的能级的值。有机EL器件的性能虽然不是仅由该值来决定,但该值越大,对各种颜色的器件、荧光以及磷光用材料的适合性也越高。
在将由胺衍生物形成的有机EL器件作为汽车等的车载面板来使用的情况下,考虑到夏天车内温度上升等,器件的耐热性成为问题。随之也要求材料(化合物)具有耐热性,因此优选胺衍生物的玻璃化转变温度为120℃以上。
实施例
下面将基于实施例对本发明更详细地进行说明,但本发明并不受这些实施例的任何限定。
需要说明的是,将本实施例中使用的分析仪器及测定方法列举如下。
[元素分析]
元素分析仪:珀金埃尔默全自动元素分析装置 2400II
氧瓶燃烧-IC测定法:东曹制 离子色谱法 IC-2001
[质量分析]
质量分析装置:日立制作所制 M-80B
测定方法:FD-MS分析
[HOMO测定]
HOMO的测定(循环伏安法)按下述方法进行。
测定装置:北斗电工公司制 HA-501,HB-104
测定方法:工作电极 玻碳电极
对电极 铂电极,
参比电极 Ag/Ag+
支持电解质 四正丁基高氯酸铵
溶剂 二氯甲烷
[LUMO测定]
测定装置:日立制作所制 紫外可见分光光度计 U-2010
测定方法:溶剂 四氢呋喃(10-5mol/l溶液)
[玻璃化转变温度测定]
测定装置:マックサイエンス制 DSC-3100
测定方法:标准样品=Al2O3 5.0mg,升温速度=10℃/分钟(氮气气氛)
[HPLC分析]
测定装置:东曹制マルチステ一ションLC-8020
测定方法:色谱柱 Inertsil ODS-3V(4.6mmΦ×250mm)
检测器 UV检测(波长254nm)
洗脱液 甲醇/四氢呋喃=9/1(v/v比)
[分解温度测定]
测定装置:リガク制system8100
测定方法:标准样品=Al2O3 5.0mg,升温速度=10℃/分钟(氮气气氛)
[升华温度测定]
测定装置:ALSテクノロジ一制有机材料升华提纯装置 P-150
测定方法:升华压力<10-3Pa,目视测定升华温度
合成例1化合物A的合成
在300ml茄型烧瓶中添加18.6g(100mmol)2’-羟基-1’-萘乙酮[和光纯药品]、100ml二氯甲烷[关东化学品]和39.6g(500mmol)吡啶[キシダ化学品],将反应液冷却至5℃以下。以反应温度不超过5℃的方式滴加31.0g(110mmol)三氟甲烷磺酸酐[和光纯药品]后,在室温下搅拌过夜。在反应液中添加水而分层。对有机层,用3.5%盐酸水溶液及水清洗后,用无水硫酸镁进行干燥,浓缩后分离出32.7g微黄色油状物,即1’-萘乙酮-2’-三氟甲磺酸酯。需要说明的是,不对生成物进行提纯,直接将其用于下面的反应。
接着,在500ml茄型烧瓶中添加15.1g(47.5mmol)得到的1’-萘乙酮-2’-三氟甲磺酸酯、7.8g(50.0mmol)4-氯苯基硼酸[东京化成品]、549mg(0.475mmol)四(三苯基膦)钯[アルドリッチ品]、100.7g 20重量%的碳酸钠水溶液及250ml四氢呋喃[关东化学品],在60℃下加热搅拌过夜。冷却至室温后,分层。对得到的有机层,用水进行清洗,用无水硫酸镁进行干燥处理后,浓缩得到12.4g淡黄色的结晶。通过1H-NMR测定确认为目标物2’-(4-氯苯基)-1’-萘乙酮,不对生成物进行提纯,直接将其用于下面的反应。
1H-NMR(200MHz、CDCl3):2.12(3H、s)、7.33-7.65(7H、m)、7.78-8.01(3H、m)
13C-NMR(50MHz、CDCl3):32.9、124.7、126.5、127.1、127.6、128.3、128.8、128.9、129.5、130.6、132.6、134.3、134.4、138.4、138.7、207.1
接着,在300ml茄型烧瓶中添加9.8g(35mmol)之前得到的2’-(4-氯苯基)-1’-萘乙酮、70ml四氢呋喃[关东化学品]、70ml乙醇[关东化学品]。溶解后,添加6.6g(175mmol)硼氢化钠[キシダ化学品],在室温下搅拌8小时。
边注意发泡边添加100g 10%氯化铵水溶液,然后进行减压浓缩。用200ml甲苯萃取残渣,用水清洗,用无水硫酸镁进行干燥处理后,进行浓缩,得到9.4g淡黄色的结晶。通过1H-NMR测定确认为目标物1-(1-羟基)乙基-2-(4-氯苯基)萘,不对生成物进行提纯,直接将其用于下面的反应。
1H-NMR(200MHz、CDCl3):1.71(3H、d、J=7.0Hz)、2.05(1H、br-s)、5.35(1H、q、J=7.0Hz)、7.16-7.63(7H、m)、7.69-7.95(2H、m)、8.76-8.93(1H、br-d)
13C-NMR(50MHz、CDCl3):23.9、68.9、125.8、125.9、127.0、127.8、127.9、128.4、128.8、130.4、130.8、133.2、134.2、136.9、137.1、140.6
接着,在100ml茄型烧瓶中添加2.8g(10mmol)之前得到的1-(1-羟基)乙基-2-(4-氯苯基)萘、20ml氯仿[关东化学品]。冷却到0℃后,滴加1.85g(13mmol)三氟化硼乙醚[关东化学品],在室温下搅拌1小时。
添加20g水终止反应后,将有机层用水进行清洗,用无水硫酸镁进行干燥处理后,浓缩得到2.7g淡黄色的固体。通过1H-NMR测定确认为目标物9-氯-11-甲基-11H-苯并[a]芴,不对生成物进行提纯,直接将其用于下面的反应。
1H-NMR(200MHz、CDCl3):1.66(3H、d、J=7.2Hz)、4.33(1H、q、J=7.2Hz)、7.32-7.65(5H、m)、7.70(1H、d、J=8.1Hz)、7.80-8.01(3H、m)、8.06(1H、d、J=8.0Hz)
将2.7g(10mmol)得到的9-氯-11-甲基-11H-苯并[a]芴、2.3g(10mmol)苄基三乙基氯化铵[キシダ化学品]、4.3g(30mmol)碘甲烷[关东化学品]溶解到20ml二甲亚砜[和光纯药品]中,冷却到0℃后,边搅拌边滴加1.2g(30mmol)48%氢氧化钠水溶液。在室温下搅拌1小时后,加入50ml甲苯[关东化学品],之后,将有机层用水进行清洗。用硫酸镁干燥后,浓缩萃取液而得到淡黄色的结晶。通过硅胶柱层析法(洗脱液:己烷),分离出2.0g作为白色结晶的9-氯-11,11-二甲基-11H-苯并[a]芴(化合物A)(收率72%)。
1H-NMR(200MHz、CDCl3):1.73(6H、s)、7.21-7.66(5H、m)、7.69(1H、d、J=7.8Hz)、7.80-7.99(3H、m)、8.19(1H、d、J=8.3Hz)
13C-NMR(50MHz、CDCl3):26.3、48.8、118.6、120.6、122.8、124.0、125.0、126.2、127.2、128.7、130.0、132.7、134.0、135.6、137.8、147.1、157.0
实施例1化合物1-4的合成
在氮气气氛下,在具备搅拌装置的500ml烧瓶中添加27.9g(0.30mol)苯胺[キシダ化学品]、23.3g(0.10mol)4-溴联苯[和光纯药品]、14.4g(0.15mol)叔丁醇钠[关东化学品]、450mg(2.0mmol)醋酸钯[キシダ化学品]、1.6g(8.0mmol)三叔丁膦[アルドリッチ品]、300.0g邻二甲苯[キシダ化学品],在130℃下搅拌10小时。反应结束后,添加50ml蒸馏水,在室温下搅拌0.5小时并静置后,分离水层。用饱和氯化钠水溶液进行清洗并分液后,通过减压浓缩蒸馏除去邻二甲苯溶剂。再将得到的残渣用硅胶柱层析法进行分离,得到23.1g白色固体(收率94%、纯度99.9%)。
通过质量分析及元素分析的结果,确认得到的白色固体为N-苯基-N-4-联苯基胺。
质量分析(FDMS):245(M+)
元素分析(计算值):C=88.1、H=6.2、N=5.7
元素分析(实测值):C=88.0、H=6.2、N=5.8
接着,在氮气气氛下,在具备搅拌装置的500ml烧瓶中添加12.2g(50mmol)得到的N-苯基-N-4-联苯基胺、14.0g(50mmol)合成例1中得到的化合物A、5.8g(60mmol)叔丁醇钠[关东化学品]、225mg(1.0mmol)醋酸钯[キシダ化学品]、0.8g(4.0mmol)三叔丁膦[アルドリッチ品]、100.0g邻二甲苯[キシダ化学品],在140℃下搅拌10小时。反应结束后,添加50ml蒸馏水,在室温下搅拌0.5小时并静置后,分离水层。用饱和氯化钠水溶液清洗并分液后,通过减压浓缩蒸馏除去邻二甲苯溶剂。再将得到的残渣利用硅胶柱层析法进行分离,得到21.7g淡黄色固体(收率89%、纯度99.9%)。
通过质量分析及元素分析的结果,确认得到的淡黄色固体为目标化合物1-4。
质量分析(FDMS):487(M+)
元素分析(计算值):C=91.1、H=6.0、N=2.9
元素分析(实测值):C=81.1、H=6.1、N=2.8
实施例2化合物1-14的合成
在氮气气氛下,在具备搅拌装置的300ml烧瓶中添加11.1g(40mmol)合成例1中得到的化合物A、1.9g(20mmol)苯胺[和光纯药品]、4.8g(50mmol)叔丁醇钠[キシダ化学品]、225mg(1.0mmol)醋酸钯[キシダ化学品]、0.8g(4.0mmol)三叔丁膦[アルドリッチ品]、100.0g邻二甲苯[キシダ化学品],在140℃下搅拌15小时。反应结束后,添加30ml蒸馏水,在室温下搅拌0.5小时并静置后,分离水层。用饱和氯化钠水溶液清洗并分液后,通过减压浓缩蒸馏除去邻二甲苯溶剂。再将得到的残渣利用硅胶柱层析法进行分离,得到10.2g淡黄色固体(收率88%、纯度99.9%)。
通过质量分析及元素分析的结果,确认得到的淡黄色固体为目标化合物1-14。
质量分析(FDMS):577(M+)
元素分析(计算值):C=91.5、H=6.1、N=2.4
元素分析(实测值):C=91.5、H=6.0、N=2.5
实施例3化合物1-16的合成
使用2.1g(20mmol)对甲苯胺[和光纯药品]代替1.9g(20mmol)苯胺[和光纯药品],除此之外,根据实施例2的方法进行,结果得到10.1g淡黄色固体(收率85%、纯度99.9%)。
通过质量分析及元素分析的结果,确认得到的淡黄色固体为目标化合物1-16。
质量分析(FDMS):591(M+)
元素分析(计算值):C=91.3、H=6.3、N=2.4
元素分析(实测值):C=91.4、H=6.2、N=2.4
实施例4化合物1-18的合成
使用1.9g(20mmol)4-氨基吡啶[和光纯药品]代替1.9g(20mmol)苯胺[和光纯药品],除此之外,根据实施例2的方法进行,结果得到10.0g淡黄色固体(收率87%、纯度99.9%)。
通过质量分析及元素分析的结果,确认得到的淡黄色固体为目标化合物1-18。
质量分析(FDMS):578(M+)
元素分析(计算值):C=89.2、H=5.9、N=4.8
元素分析(实测值):C=89.0、H=6.0、N=4.9
参考例1比较化合物M1的合成
使用6.7g(20mmol)N,N’-二苯基联苯胺[アルドリッチ品]代替1.9g(20mmol)苯胺[和光纯药品],除此之外,根据实施例2的方法进行,结果得到14.0g淡黄色固体(收率85%、纯度99.9%)。
通过质量分析及元素分析的结果,确认得到的淡黄色固体为目标比较化合物M1。
质量分析(FDMS):820(M+)
元素分析(计算值):C=90.7、H=5.9、N=3.4
元素分析(实测值):C=90.7、H=6.0、N=3.3
比较化合物M1
测定实施例1~4中得到的化合物1-4、1-14、1-16、1-18及参考例1中得到的比较化合物M1的HOMO(eV)、LUMO(eV)、玻璃化转变温度(℃)、升华温度(℃)及分解温度(℃)。将结果示于下述表1。为了比较,将对一直以来作为有机EL用材料所公知的α-NPD(4,4’-二[N-(1-萘基)-N-苯基氨基]联苯)所测定的结果也一并示于表1。
[表1]
实施例5有机EL器件的制作
就基板而言,使用带有将2mm宽的氧化铟-锡(ITO)膜图案化为条纹状的ITO透明电极的玻璃基板。用丙酮、异丙醇依次对该基板进行超声波清洗,然后,用异丙醇煮沸清洗后,干燥。进而,将该基板进行UV/臭氧处理后而得到的基板作为透明导电性支撑基板来使用。首先,将上述玻璃基板导入真空蒸镀槽内,减压至1.0×10-4Pa。然后,在该ITO透明电极上,利用真空蒸镀法以25nm的膜厚使铜酞菁成膜,形成空穴注入层。
接着,利用真空蒸镀法以45nm的膜厚使实施例2中合成的化合物(1-14)成膜,形成空穴传输层。接着,利用真空蒸镀法以60nm的膜厚使三羟基喹啉铝络合物成膜,形成发光层兼电子传输层。接着,作为阴极,使LiF成膜为0.5nm、Al成膜为100nm,从而形成金属电极。利用触针式膜厚测定器(DEKTAK)对各自的膜厚进行测定。进而,将该器件密封在氧及水分浓度在1ppm以下的氮气气氛球形箱内。密封使用玻璃制密封帽和上述成膜基板环氧型紫外线固化树脂(ナガセケムテックス公司制)。
在制作的有机EL器件中,以ITO电极为正极、LiF-Al电极为负极外加直流电流,使用TOPCON公司制的LUMlNANCEMETER(BM-9)的亮度计对发光特性进行评价。作为发光特性,测定通过20mA/cm2的电流密度时的驱动电压(V)、亮度(cd/m2)、电流效率(cd/A)和功率效率(lm/W)。将结果示于下述表2中。
实施例6有机EL器件的制作
作为空穴传输层,使用实施例3中合成的化合物(1-16)代替实施例2中合成的化合物(1-14),除此之外,根据实施例5同样地制作有机EL器件。将在20mA/cm2的恒电流密度条件下驱动时的驱动电压、亮度、电流效率及功率效率的测定结果一并示于下述表2中。
比较例1有机EL器件的制作
作为空穴传输层,使用α-NPD代替实施例2中合成的化合物(1-14),除此之外,根据实施例5同样地制作有机EL器件。将在20mA/cm2的恒电流密度条件下驱动时的驱动电压、亮度、电流效率及功率效率的测定结果一并示于下述表2中。
比较例2有机EL器件的制作
作为空穴传输层,使用参考例1中合成的化合物(M1)代替实施例2中合成的化合物(1-14),除此之外,根据实施例5同样地制作有机EL器件。将在20mA/cm2的恒电流密度条件下驱动时的驱动电压、亮度、电流效率及功率效率的测定结果一并示于下述表2中。
[表2]
产业上的可利用性
与现有的材料相比,本发明的通式(1)所表示的胺衍生物可以在低电压下驱动,且显示出高功率效率,因此可以作为有机EL器件或电子照相感光体等的空穴注入材料、空穴传输材料或发光材料来利用。特别是作为空穴传输材料使用时,可以期待比现有材料优良的驱动电压的改善和高功率效率。
而且,也可以在光电转换器件、太阳能电池、图像传感器等有机光导电材料领域中应用。
Claims (7)
2.根据权利要求1所述的胺衍生物,其中,通式(1)中的R1及R2表示可以具有取代基的碳原子数6~18的芳基或可以具有取代基的碳原子数5~18的杂芳基。
3.根据权利要求1或2所述的胺衍生物,其中,通式(1)中的R3及R4表示氢原子、碳原子数1~6的直链、支链或环状的烷基、碳原子数1~6的直链、支链或环状的烷氧基、可以具有取代基的碳原子数6~18的芳基或可以具有取代基的碳原子数5~18的杂芳基;或者,R3及R4与两者所键合的苯并芴骨架中的碳原子一起形成碳原子数3~8的环烷基。
4.根据权利要求1~3中任一项所述的胺衍生物,其中,[LUMO(eV)-HOMO(eV)]的值为3.0(eV)以上。
5.根据权利要求1~4中任一项所述的胺衍生物,其中,玻璃化转变温度(℃)为120℃以上。
6.一种有机电致发光器件,其特征在于,具备由权利要求1~5中任一项所述的胺衍生物形成的发光层、空穴传输层及空穴注入层中的任意一层以上。
7.一种有机电致发光器件的制造方法,其特征在于,利用真空蒸镀法将权利要求1~5中任一项所述的胺衍生物制成薄膜,形成发光层、空穴传输层及空穴注入层中的任意一层以上。
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KR102321559B1 (ko) | 2019-10-21 | 2021-11-05 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102192497B1 (ko) | 2019-10-21 | 2020-12-17 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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EP2439190A1 (en) | 2012-04-11 |
JP2011012047A (ja) | 2011-01-20 |
TWI490188B (zh) | 2015-07-01 |
EP2439190B1 (en) | 2015-04-15 |
KR20120029446A (ko) | 2012-03-26 |
KR101652096B1 (ko) | 2016-08-29 |
WO2010140617A1 (ja) | 2010-12-09 |
TW201105616A (en) | 2011-02-16 |
EP2439190A4 (en) | 2013-10-23 |
CN102459149B (zh) | 2014-10-29 |
US8846214B2 (en) | 2014-09-30 |
US20120112177A1 (en) | 2012-05-10 |
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