WO2013145667A1 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2013145667A1 WO2013145667A1 PCT/JP2013/001947 JP2013001947W WO2013145667A1 WO 2013145667 A1 WO2013145667 A1 WO 2013145667A1 JP 2013001947 W JP2013001947 W JP 2013001947W WO 2013145667 A1 WO2013145667 A1 WO 2013145667A1
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- unsubstituted
- carbon atoms
- ring
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000010409 thin film Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 110
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- -1 Child Chemical group 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 150000002910 rare earth metals Chemical class 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 150000002909 rare earth metal compounds Chemical class 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 167
- 239000010408 film Substances 0.000 description 22
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 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 6
- 239000011575 calcium Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000008021 deposition Effects 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 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
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 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 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical compound C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- FZTBAQBBLSYHJZ-UHFFFAOYSA-N 2-phenyl-1,3-oxazol-4-ol Chemical compound OC1=COC(C=2C=CC=CC=2)=N1 FZTBAQBBLSYHJZ-UHFFFAOYSA-N 0.000 description 1
- CCMLIFHRMDXEBM-UHFFFAOYSA-N 2-phenyl-1,3-thiazol-4-ol Chemical compound OC1=CSC(C=2C=CC=CC=2)=N1 CCMLIFHRMDXEBM-UHFFFAOYSA-N 0.000 description 1
- HJJXCBIOYBUVBH-UHFFFAOYSA-N 2-phenyl-1h-benzimidazol-4-ol Chemical compound N1C=2C(O)=CC=CC=2N=C1C1=CC=CC=C1 HJJXCBIOYBUVBH-UHFFFAOYSA-N 0.000 description 1
- VHRHRMPFHJXSNR-UHFFFAOYSA-N 2-phenylpyridin-3-ol Chemical compound OC1=CC=CN=C1C1=CC=CC=C1 VHRHRMPFHJXSNR-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical group C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical group C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- LXELBQMGKYWFHS-UHFFFAOYSA-N C=C(C(c1ccccc11)=O)C1=O Chemical compound C=C(C(c1ccccc11)=O)C1=O LXELBQMGKYWFHS-UHFFFAOYSA-N 0.000 description 1
- GSQVDQRKDQPDBY-LMCGJEQXSA-N COc(cc1)cc(-c(c2c3)cc4c3-c3cc(OC)ccc3/C4=N\C#N)c1/C2=N\C#N Chemical compound COc(cc1)cc(-c(c2c3)cc4c3-c3cc(OC)ccc3/C4=N\C#N)c1/C2=N\C#N GSQVDQRKDQPDBY-LMCGJEQXSA-N 0.000 description 1
- GEPSWDHBXGSIGF-UHFFFAOYSA-N COc(cc1C(C2C=C3c4cc(OC)ccc44)C=C3C4=C(C#N)C#N)ccc1C2=C(C#N)C#N Chemical compound COc(cc1C(C2C=C3c4cc(OC)ccc44)C=C3C4=C(C#N)C#N)ccc1C2=C(C#N)C#N GEPSWDHBXGSIGF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(*)c2c(*)c(*)c(*)nc2c2nc(*)c(*)c(*)c12 Chemical compound Cc1c(*)c2c(*)c(*)c(*)nc2c2nc(*)c(*)c(*)c12 0.000 description 1
- AJPAYWQVIQAEDZ-UHFFFAOYSA-N Cc1c(-c2ccc(C(F)(F)F)cc2C2=C(C#N)C#N)c2c(C)c(-c2ccc(C(F)(F)F)cc22)c1C2=C(C#N)C#N Chemical compound Cc1c(-c2ccc(C(F)(F)F)cc2C2=C(C#N)C#N)c2c(C)c(-c2ccc(C(F)(F)F)cc22)c1C2=C(C#N)C#N AJPAYWQVIQAEDZ-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- YFBNEWJCEUJHNU-NCOOAAOESA-N N#C/N=C(/c1c2)\c(cc(cc3)Oc4ccc(C(F)(F)F)cc4)c3-c1cc1c2-c(ccc(Oc2ccc(C(F)(F)F)cc2)c2)c2/C1=N\C#N Chemical compound N#C/N=C(/c1c2)\c(cc(cc3)Oc4ccc(C(F)(F)F)cc4)c3-c1cc1c2-c(ccc(Oc2ccc(C(F)(F)F)cc2)c2)c2/C1=N\C#N YFBNEWJCEUJHNU-NCOOAAOESA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- 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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- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
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- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
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- 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
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- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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Definitions
- the present invention relates to an organic electroluminescence device using a light transmissive electrode as a cathode.
- An organic electroluminescence element is a self-luminous element that utilizes the principle of emitting light by the recombination energy of holes injected from an anode and electrons injected from a cathode.
- a light-transmitting conductive film is generally used for one or both of the anode and the cathode.
- an indium tin oxide film (Indium-Tin-Oxide: ITO) is preferably used because of its excellent transparency and conductivity.
- ITO has a work function of about 5 eV and is suitable for the anode.
- the cathode is not suitable for increasing the difference in affinity level with surrounding layers such as an electron transport layer. Therefore, in an organic EL element that extracts light from the cathode side, a metal having a low work function such as cesium (Cs) and an electron-transporting organic material are provided between the organic light-emitting layer and the electrode made of a transparent conductive film. It has been proposed to form a mixed electron injection layer. Thereby, the electron injection property of the cathode is enhanced.
- Cs cesium
- the transparent conductive films typified by ITO are made of a metal oxide, and are formed by sputtering using argon (Ar) or oxygen (O 2 ) as a process gas.
- Ar argon
- O 2 oxygen
- the electron injection layer containing the above-described low work function metal may be decomposed and oxidized, and the electron injection property may be lowered. For this reason, there are problems that the drive voltage of the element increases, current leakage occurs, and the lifetime decreases.
- an organic EL element using copper phthalocyanine as a base of a transparent conductive film has been disclosed (see Patent Document 1).
- An organic EL element is disclosed in which a laminate of layers made of is formed in an electron transport portion, and a transparent conductive film is formed thereon (see Patent Document 2 and FIG. 19).
- a donor-containing layer, an acceptor-containing layer, and a cathode are provided in this order, and an organic EL device is disclosed in which the donor-containing layer contains at least one selected from the group consisting of a donor metal, a donor metal compound, and a donor metal complex.
- the donor-containing layer contains at least one selected from the group consisting of a donor metal, a donor metal compound, and a donor metal complex.
- An object of the present invention is to provide an organic EL element that extracts light from the cathode side and has high luminous efficiency and low driving voltage.
- the following organic EL device has an anode, one or more organic thin film layers including a light emitting layer, a donor-containing layer, an acceptor-containing layer, and a light-transmitting cathode in this order, and the donor-containing layer is represented by the following formula (I) or (II) An organic electroluminescence device containing the compound.
- R 1a to R 7a and R 1b to R 7b each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted pyridyl group, substituted or An unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted ring group having 7 to 50 carbon atoms An aralkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, A substituted or
- L 1a and L 1b are each a single bond or a linking group.
- Ar 1a and Ar 1b are each a substituted or unsubstituted aromatic group having 6 to 60 carbon atoms.
- n is 1 to 4, and when n is 2 or more, the groups having a phenanthroline skeleton in parentheses may be the same or different.
- an organic EL element that extracts light from the cathode side and has high luminous efficiency and low driving voltage.
- the organic EL device includes an anode, one or more organic thin film layers including a light emitting layer, a donor-containing layer, an acceptor-containing layer, and a light-transmitting cathode in this order.
- FIG. 1 shows an element configuration of an embodiment of an organic light emitting element according to the present invention.
- the organic EL element 1 has a configuration in which an anode 10, a hole injection layer 20, a hole transport layer 30, a light emitting layer 40, a donor-containing layer 50, an acceptor-containing layer 60, and a light-transmitting cathode 70 are stacked in this order. ing.
- the acceptor-containing layer 60 is a layer that extracts electrons from the cathode 70 (accepts electrons) and transfers them to the donor-containing layer 50.
- a material having a small work function is used as a material of the cathode in order to inject electrons from the cathode to an organic substance.
- an increase in driving voltage can be reduced even when a material having a high work function such as ITO is employed.
- the donor-containing layer 50 is a layer that extracts electrons from the acceptor-containing layer 60 and injects electrons into the light-emitting layer 40 (donates electrons). By providing the donor-containing layer 50, it becomes easier to receive electrons from the acceptor layer 60, which is effective in lowering the driving voltage, further increasing the efficiency, and extending the life.
- the acceptor included in the acceptor-containing layer 60 extracts electrons from the contact surface between the cathode 70 and the acceptor. Since the acceptor-containing layer 60 is electron transportable, electrons are transported from the contact surface into the acceptor-containing layer 60 in the direction of the donor-containing layer 50. Further, it is injected from the donor-containing layer 50 toward the light emitting layer 40. On the other hand, holes are injected from the anode 10 into the hole injection layer 20 and the hole transport layer 30 and further injected into the light emitting layer 40. In the light emitting layer 40, holes and electrons are recombined to emit light.
- the provision of the donor-containing layer 50 can eliminate a step having a large affinity level between the light-emitting layer 40 and the acceptor-containing layer 60.
- the difference in affinity level between the acceptor-containing layer 60 and the light-emitting layer 40 is large, so that a high voltage must be applied. For this reason, in this element structure, even if a negative bias is applied to the cathode, it is not possible to emit light well.
- an acceptor-containing layer 60 and a donor-containing layer 50 are provided between the cathode 70 and the light-emitting layer 40, thereby facilitating electron transport and reducing the voltage, efficiency, and life of the organic light-emitting device. Is planned.
- the donor-containing layer contains a compound represented by the following formula (I) or (II).
- the compound represented by the formula (I) or (II) is an organic compound, it is resistant to sputtering damage. Therefore, even if a transparent electrode layer such as ITO is formed on the cathode, deterioration of the organic thin film layer such as the light emitting layer can be suppressed.
- a transparent electrode layer such as ITO
- deterioration of the organic thin film layer such as the light emitting layer can be suppressed.
- R 1a to R 7a and R 1b to R 7b each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, substituted or unsubstituted Substituted pyridyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted ring Aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted ring carbon atoms An amino group substituted with an arylthio group having 6 to 50 carbon atoms
- R 1a to R 7a or R 1b to R 7b adjacent ones may be bonded to each other to form a ring .
- the ring include a benzene ring, a naphthalene ring, a pyrazine ring, a pyridine ring, and a furan ring.
- L 1a and L 1b are each a single bond or a linking group.
- the linking group include a substituted or unsubstituted aromatic group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkylene group having 1 to 8 carbon atoms, and a substituted or unsubstituted heterocyclic group.
- a substituted or unsubstituted benzene ring group, a substituted or unsubstituted naphthalene ring group, a substituted or unsubstituted methylene group, or a substituted or unsubstituted pyridine ring group is preferable.
- Ar 1a and Ar 1b are each a substituted or unsubstituted aromatic group having 6 to 60 carbon atoms.
- n is 1 to 4, and when n is 2 or more, the groups having a phenanthroline skeleton in parentheses may be the same or different.
- R 1a to R 7a , R 1b to R 7b , L 1a and L 1b are each represented by the formula (I) And the same group as R 1a to R 7a , R 1b to R 7b , L 1a and L 1b in (II).
- R 11a to R 20a and R 11b to R 20b are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl.
- substituted or unsubstituted alkyl group having 1 to 50 carbon atoms substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 ring carbon atoms, substituted Or an unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring carbon atoms, substituted or unsubstituted An alkoxycarbonyl group having 2 to 50 carbon atoms, an amino group substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, halogen, Child, a cyano group, a nitro group, a hydroxyl group or a carboxyl group.
- R 11a to R 20a or R 11b to R 20b adjacent ones may be bonded to each other to form a ring.
- the ring include a benzene ring, a naphthalene ring, a pyrazine ring, a pyridine ring, and a furan ring.
- the aryl group includes a monocyclic aromatic hydrocarbon ring group and a condensed aromatic hydrocarbon ring group in which a plurality of hydrocarbon rings are condensed, and the heteroaryl group is a monocyclic heteroaromatic group.
- a hetero-fused aromatic ring group in which a plurality of heteroaromatic rings are condensed and a hetero-fused aromatic ring group in which an aromatic hydrocarbon ring and a heteroaromatic ring are condensed.
- “Unsubstituted” in “substituted or unsubstituted...” Means that a hydrogen atom is substituted, and a hydrogen atom in a compound according to one embodiment of the present invention is an isotope having a different neutron number. That is, it includes light hydrogen (protium), deuterium (deuterium), and tritium.
- Ring-forming carbon means a carbon atom constituting an aromatic ring, and ring-forming atom (nuclear atom) constitutes a heterocyclic ring (including a saturated ring, an unsaturated ring and an aromatic heterocyclic ring). Means carbon and heteroatoms.
- the aryl group having 6 to 60 ring carbon atoms preferably has 6 to 30 carbon atoms, particularly preferably 6 to 20 carbon atoms.
- the aromatic group represented by Ar 1a and Ar 1b include the above-described aryl group and a bivalent or higher-valent group derived by removing a hydrogen atom from the aryl group.
- R 1a to R 7a and R 1b to R 7b in the formulas (I) and (II) are preferably hydrogen, phenyl, or naphthyl.
- alkyl group having 1 to 50 carbon atoms there is a linear or branched alkyl group.
- it has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, and examples thereof include methyl, ethyl, propyl, butyl, pentyl, hexyl and the like.
- Examples of the cycloalkyl group having 3 to 50 ring carbon atoms include cyclopentyl and cyclohexyl.
- the aralkyl group having 7 to 50 ring carbon atoms is represented by —Y—Z.
- Y include alkylene examples corresponding to the above alkyl groups, and examples of Z include the above aryl groups. Is mentioned.
- the aryl part of the aralkyl group preferably has 6 to 30 carbon atoms.
- the alkyl moiety preferably has 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms. For example, benzyl group, phenylethyl group, 2-phenylpropan-2-yl group.
- An alkoxy group having 1 to 50 carbon atoms is represented as —OY, and examples of Y include the above alkyl groups.
- the alkoxy group preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms, and examples thereof include methoxy, ethoxy, propoxy, butoxy and the like.
- An aryloxy group having 6 to 50 ring carbon atoms is represented by —OY, and examples of Y include the above aryl groups.
- the number of carbon atoms is preferably 6 to 20, more preferably 6 to 16, and particularly preferably 6 to 12, and examples thereof include phenyloxy and 2-naphthyloxy.
- An arylthio group having 6 to 50 ring carbon atoms is represented by —SY, and examples of Y include the above aryl groups. Preferably it has 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenylthio.
- the alkoxycarbonyl group having 2 to 50 carbon atoms preferably has 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl and ethoxycarbonyl.
- Examples of the amino group substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms include diarylamino, alkylarylamino, and arylamino.
- Examples of the alkyl group and aryl group bonded to the nitrogen atom include the above-described aryl group and alkyl group. Preferably it has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, particularly preferably 6 carbon atoms, and examples thereof include diphenylamino and the like.
- halogen atom examples include a fluorine atom, a chlorine atom and a bromine atom, preferably a fluorine atom.
- Substituents for the above groups are each independently a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkenyl group having 2 to 20 carbon atoms, or a ring-forming carbon number of 3
- aryl group examples include the aryl group, alkyl group, cycloalkyl group, heteroaryl group, alkoxy group, halogen atom, and cyano group. Furthermore, these groups may have a similar substituent.
- alkenyl group examples include a substituent having an unsaturated bond in the molecule of the alkyl group described above.
- silyl group having an aryl group examples include a triarylsilyl group, an alkylarylsilyl group, and a trialkylsilyl group.
- substituents include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, trimethylsilyl, triphenylsilyl.
- the donor-containing layer preferably contains at least one of an electron-donating metal, a metal compound, and a metal complex in addition to the compound of the above formula (I) or (II).
- a layer containing at least one is preferable.
- alkali metal examples include lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs) and the like, and those having a work function of 2.9 eV or less are particularly preferable. Of these, Li, K, Rb, and Cs are preferable, Li, Rb, and Cs are more preferable, and Li is most preferable.
- alkaline earth metal examples include calcium (Ca), magnesium (Mg) strontium (Sr), barium (Ba) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
- alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
- alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
- the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), include such terbium fluoride (TbF 3) is, YbF 3, ScF 3, TbF 3 are preferable.
- the organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above.
- the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.
- the addition form of the metal, compound and complex it is preferable to form a layer or island in the interface region.
- a forming method while vapor-depositing at least one of the above metal, compound and complex by resistance heating vapor deposition, an organic material which is a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and the above metal, A method of dispersing at least one of the compound and the complex is preferable.
- At least one of the metal, the compound and the complex in a layered form, after forming the light emitting material or the electron injecting material which is an organic layer at the interface in a layered form, at least one of the metal, the compound and the complex is singly used.
- Vapor deposition is performed by resistance heating vapor deposition, and the layer is preferably formed with a thickness of 0.1 nm to 15 nm.
- Vapor deposition is performed by a resistance heating vapor deposition method alone, and is preferably formed with an island thickness of 0.05 nm to 1 nm.
- the ratio of at least one of the main component and the metal, compound, and complex is a film thickness ratio of main component: electron-donating dopant and / or organic metal.
- Complex 100: 1 to 1: 1 is preferable, and 50: 1 to 4: 1 is more preferable.
- the thickness of the donor-containing layer is preferably from 0.1 nm to 100 nm, particularly preferably from 1 nm to 50 nm.
- the organic EL device only needs to use the compound represented by the above formula (I) or (II) in the donor-containing layer, and the anode, the organic thin film layer, As the cathode and the like, members known in the art can be appropriately used.
- the organic light-emitting element is not limited to the structure shown in FIG.
- the hole transport layer and the hole injection layer are arbitrary layers, they can be omitted, and an electron transport layer or the like can be provided between the light emitting layer and the donor-containing layer.
- a hole transport layer, a hole injection layer, a light emitting layer, an electron transport layer, and the like correspond to the organic thin film layer according to one embodiment of the present invention.
- a buffer layer may be formed between the cathode and the acceptor-containing layer.
- Japanese Patent No. 4392050 can be referred to for the buffer layer.
- it can also be used for an organic EL element (MPE element) having a configuration in which a plurality of light emitting units each composed of an organic layer having at least a light emitting layer are arranged with a charge generation layer interposed between an anode and a cathode.
- MPE element organic EL element
- the organic EL element according to one embodiment of the present invention may be a top emission type or a bottom emission type.
- light is extracted from the cathode side.
- the light transmissive cathode preferably has a light transmittance of 10% or more in the visible light region (450 to 650 nm). Preferably it is 30% or more, more preferably 50% or more.
- Examples of the constituent material of the light transmissive cathode include ITO, tin oxide (NESA), indium zinc oxide alloy (IZO), zinc oxide (ZnO), IZO / Ag / IZO, ITO / Ag / ITO, and the like.
- an easily reducing organic compound can be used as the acceptor-containing layer.
- the ease of reduction of a compound can be measured by a reduction potential.
- the reduction potential using a saturated calomel (SCE) electrode as a reference electrode is preferably ⁇ 0.8 V or more, more preferably ⁇ 0.3 V or more, and particularly preferably tetracyanoquinodimethane (TCNQ) reduction.
- SCE saturated calomel
- TCNQ tetracyanoquinodimethane
- examples of the acceptor-containing layer include a layer containing a compound represented by the following formula (III). Since this compound is resistant to sputtering damage and has high adhesion (contact property) to the donor-containing layer and the cathode, it is effective in improving the lifetime of the device.
- R 1c to R 6c in the formula are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 ring carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted carbon number
- the layer containing the compound represented by following formula (IV) is mentioned.
- Ar 1 is an aromatic ring having 6 to 24 ring carbon atoms or a heterocyclic ring having 5 to 24 ring atoms, preferably an aromatic ring having 6 to 14 ring carbon atoms or the number of ring forming atoms. 5-14 heterocycles.
- the aromatic ring include a benzene ring, a naphthalene ring, a fluorene ring, a 9,9-dimethylfluorene ring, and a 9,9-dioctylfluorene ring.
- heterocyclic ring examples include a pyrazine ring, a pyridine ring, a quinoxaline ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a phenanthroline ring, a naphthyridine ring, and a tetraazaanthracene ring.
- the aromatic ring and heterocyclic ring a substituted or unsubstituted alkyl group represented by R1 ⁇ R 4 described below, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group Substituted or unsubstituted heterocyclic group, halogen atom, substituted or unsubstituted fluoroalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted fluoroalkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted It may be substituted with a substituted aralkyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group.
- R 1 to R 4 may be the same as or different from each other, and are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group.
- R 1 and R 2 and R 3 and R 4 may be bonded to each other to form a ring.
- alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, octyl group and the like.
- cycloalkyl group examples include a cyclopentyl group and a cyclohexyl group.
- Alkenyl groups include vinyl groups, propenyl groups (including double bond positional isomers), butenyl groups (including double bond positional isomers), pentenyl groups (including double bond positional isomers), etc. can give.
- aryl group phenyl group, biphenyl group, naphthyl group, fluorophenyl group, trifluoromethylphenyl group, (trifluoromethyl) fluorophenyl group, trifluorophenyl group, bis (trifluoromethyl) phenyl group, (Trifluoromethyl) difluorophenyl group, trifluoromethoxyphenyl group, trifluoromethoxyfluorophenyl group and the like can be mentioned.
- heterocyclic group include residues such as pyridine, pyrazine, furan, imidazole, benzimidazole, and thiophene.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- fluoroalkyl group examples include a trifluoromethyl group, a pentafluoroethyl group, a perfluorocyclohexyl group, and a perfluoroadamantyl group.
- alkoxy group examples include a methoxy group and an ethoxy group.
- fluoroalkoxy group examples include trifluoromethoxy group, pentafluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3,3-pentafluoropropoxy group, 2,2,3,3- Examples thereof include a tetrafluoropropoxy group and a 1,1,1,3,3,3-hexafluoropropan-2-yloxy group.
- (substituted) aryloxy groups include phenyloxy group, pentafluorophenyloxy group, 4-trifluorophenyloxy group and the like.
- Examples of (substituted) aralkyloxy groups include benzyloxy group, pentafluorobenzyloxy group, 4-trifluoromethylbenzyloxy group and the like.
- Examples of (substituted) amino groups include amino groups, mono- or dimethylamino groups, mono- or diethylamino groups, mono- or diphenylamino groups, and the like.
- Examples of (substituted) silyl groups include silyl groups, mono-, di- or trimethylsilyl groups, mono-, di- or triethylsilyl groups, mono-, di- or triphenylsilyl groups.
- Examples of the optional substituent for R 1 to R 4 include the halogen atom, cyano group, alkyl group, aryl group, fluoroalkyl group, fluoroalkoxy group and heterocyclic group mentioned above.
- examples of the optional substituents referred to as “substituted or unsubstituted” include the halogen atoms, cyano groups, alkyl groups, aryl groups, fluoroalkyl groups, fluoroalkoxy groups, and heterocycles mentioned above.
- a cyclic group is mentioned.
- R 1 and R 2 and R 3 and R 4 may be bonded to each other to form a ring.
- the ring include a benzene ring, a naphthalene ring, a pyrazine ring, a pyridine ring, and a furan ring.
- at least one of R 1 to R 4 is a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, a cyano group, or at least one group selected from fluorine, a fluoroalkyl group, a fluoroalkoxy group, and a cyano group.
- An aryl group or a heterocyclic group is preferable. By using these as substituents, electron acceptability can be increased, an appropriate sublimation temperature can be obtained, or crystallization can be suppressed.
- Rg 1 and Rg 2 in the formula (IV) may be the same or different from each other, and are represented by the following formula (i) or (ii).
- X 1 and X 2 may be the same or different from each other, and are any of the divalent groups shown in the following (a) to (g). In particular, (a) to (c) are preferable from the viewpoints of excellent heat resistance or ease of synthesis.
- R 21 to R 24 may be the same or different from each other, and are a hydrogen atom, a substituted or unsubstituted fluoroalkyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, R 22 and R 23 may be bonded to each other to form a ring.
- Specific examples of the fluoroalkyl group, the alkyl group, the cycloalkyl group, the aryl group, and the heterocyclic group include the groups exemplified for R 1 to R 4 .
- Y 1 to Y 4 may be the same as or different from each other, and each represents N, CH, or C (R 5 ), and R 5 represents the same group as R 1 to R 4 . Further, it is preferable that at least one of Y 1 to Y 4 is a nitrogen atom (the same applies to Y 21 to Y 26 and Y 31 to Y 38 described later). Since at least one is a nitrogen atom, electron acceptability can be increased, heat resistance can be increased, or crystallization can be suppressed.
- the indenofluorangeone derivative of the formula (IV) is preferably represented by the following formula (IV-A) or (IV-B).
- Each symbol such as Ar 1 in the following formula (IV-A) has the same meaning as in formula (IV).
- Ar 2 in the following formula (IV-B) is synonymous with Ar 1 in the formula (IV)
- X 3 and X 4 are synonymous with X 1 and X 2 in the formula (IV)
- Y 5 to Y 8 has the same meaning as Y 1 ⁇ Y 4 in formula (IV)
- R 1 ⁇ R 4 have the same meanings as R 1 ⁇ R 4 in formula (IV).
- the indenofluorangeone derivative of the formula (IV) is represented by the following formulas (IVa) to (IVi).
- R 1 ⁇ R 4 have the same meanings as X 1 and X 2, R 1 ⁇ R 4 in formula (IV), Y 21 ⁇ Y 26, Y 31 ⁇ Y 38 and, Y 41 to Y 50 have the same meanings as Y 1 to Y 4 in formula (IV).
- formula (IV) indenofluorangeone derivatives are represented by the following formulas (IV-a) to (IV-n).
- the following formulas (IV-b), (IV-d), (IV-f), (IV-h), (IV-j), (IV-l), (IV-n), (IV-p) ) And (IV-r) have a plurality of isomers depending on the configuration of the cyano groups of the two cyanoimino groups.
- the present invention is not limited to a specific isomer.
- the invention may be a specific isomer alone or a mixture of two or more than two isomers.
- R 31 to R 52 have the same meanings as R 1 to R 4 in formula (IV).
- R 31 to R 52 adjacent to each other may be bonded to each other to form a ring.
- at least one of R 31 to R 52 is a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, a cyano group, or an aryl having at least one group selected from fluorine, a fluoroalkyl group, a fluoroalkoxy group, and a cyano group It is preferably a group or a heterocyclic group.
- the indenofluorangeone derivative has the structure of each of the above formulas, it has electron acceptability, is excellent in heat resistance, has a sublimation temperature of about 200 ° C. or higher, and can be purified by sublimation. High purity can be achieved. Moreover, the drive voltage of an element can be reduced by using it for an organic EL element, and lifetime can be improved. Furthermore, since the sublimation temperature is about 200 ° C. or higher during the manufacture of the element, it does not scatter inside the deposition film forming apparatus, so that the film forming apparatus or the organic EL element is not contaminated.
- indenofluorangeone derivative of the formula (IV) are shown below, but are not limited thereto.
- the acceptor-containing layer may be a layer made of only the compound represented by the formula (IV) or a layer made of a mixture with other materials.
- the acceptor-containing layer is preferably a layer containing a compound represented by the formula (IV) and at least one hole transport material.
- the hole transport material a material used for a hole transport layer or the like can be used. Of these, aromatic tertiary amine compounds are preferred.
- the content of the compound represented by the formula (IV) in the acceptor-containing layer is preferably 0.1% by weight to 100% by weight, and particularly preferably 10% by weight to 70% by weight.
- the film thickness of the acceptor-containing layer is preferably 1 nm to 50 nm, and particularly preferably 5 nm to 20 nm.
- the organic EL device can be produced by a known method.
- the anode and the cathode can be formed by a method such as vapor deposition or sputtering.
- Each organic thin film layer such as a light-emitting layer can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
- the form of the organic EL element which concerns on one form of this invention was demonstrated exemplifying the organic EL element 1 of FIG. 1, this invention is not limited to the form of the organic EL element 1.
- the configuration of the organic EL element according to one embodiment of the present invention is not limited to the above-described embodiment, and other known configurations can be adopted.
- a stack type multi-photon emission element MPE element having a configuration in which two or more light emitting units are sandwiched between an anode and a light transmitting cathode and a charge generation layer is sandwiched between the light emitting units. But you can.
- FIG. 2 is a schematic cross-sectional view of another embodiment of the organic EL element according to one embodiment of the present invention.
- the organic EL element 2 of the present embodiment includes an anode 20, a first light emitting unit 81, a charge generation layer 82, a second light emitting unit 83, a donor containing layer 50, an acceptor containing layer 60, and a light transmitting property on a substrate 10.
- the cathode 70 is provided in this order.
- Each of the two light emitting units has a single layer or a stacked structure having at least a light emitting layer.
- the light emitting unit preferably has a multilayer structure in which a hole transport layer, a light emitting layer, and an electron transport layer are stacked from the anode side.
- the organic EL element 2 has the same configuration as the organic EL element 1 shown in FIG. 1 except that two light emitting units are formed.
- the organic EL element 1 has an element configuration having one light emitting unit composed of the hole injection layer 20, the hole transport layer 30, and the light emitting layer 40.
- an organic EL element that emits white light can be obtained by changing the light emission color of each light emitting unit, that is, by changing the material of the light emitting layer.
- the above-described donor-containing layer and acceptor-containing layer may be used as a layer formed between the light-emitting layer and the charge generation layer.
- the 1st light emission unit 81 may be the structure which laminated
- Examples 1 to 15 ITO was formed to a thickness of 240 nm as an anode on a substrate made of a 30 mm ⁇ 30 mm glass plate.
- a cell for an organic EL element in which a region other than the light emitting region of 2 mm ⁇ 2 mm was masked with an insulating film by SiO 2 vapor deposition was produced.
- hexanitrile azatriphenylene (the following formula (HAT)) was formed to a thickness of 10 nm as a hole injection layer.
- a hole transport layer, a blue light-emitting layer, and an electron transport layer were formed in this order on the hole injection layer.
- the hole transport layer As the hole transport layer, the following formula ( ⁇ -NPD) was formed with a film thickness of 90 nm (deposition rate: 0.2 to 0.4 nm / sec) by vacuum evaporation. Subsequently, a blue light emitting layer was formed on the hole transport layer. A compound of the following formula (1) was used as the host of the light emitting layer, and a compound of the following formula (2) was used as the dopant. Vacuum deposition was performed so that the added amount of the dopant was 5% in terms of the film thickness ratio to obtain a light emitting layer having a film thickness of 30 nm.
- the following formula (Alq3) was formed to a thickness of 30 nm as an electron transport layer on the blue light-emitting layer.
- a donor-containing layer and an acceptor-containing layer were formed on the electron transport layer in this order using the compounds shown in Table 1.
- the donor-containing layer is a mixed layer of the compound of Table 1 and Li (“%” in Table 1 is a value relative to the film thickness ratio).
- the cathode (ITO or IZO: film thickness 200 nm) shown in Table 1 was formed by sputtering to produce an organic EL device.
- Comparative Example 3 An organic EL device was prepared and evaluated in the same manner as in Comparative Example 2 except that the cathode was changed to ITO to make an Mg—Ag alloy and the film thickness was 10 nm. The results are shown in Table 1.
- Comparative Example 4 An organic EL device was prepared and evaluated in the same manner as in Comparative Example 2 except that a layered body of copper phthalocyanine complex (CuPc) 10 nm and Li 1 nm was used instead of the LiF layer. The results are shown in Table 1.
- CuPc copper phthalocyanine complex
- Comparative Example 6 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the donor-containing layer was the following mixed layer of Bphen and Li (Li: 2%), the acceptor-containing layer was HAT, and the cathode was changed to IZO. did. The results are shown in Table 1.
- Comparative Example 7 An organic EL device was prepared and evaluated in the same manner as in Comparative Example 6 except that the donor-containing layer was a mixed layer of the compound of formula (3) and Ca (Ca: 10%). The results are shown in Table 1.
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Abstract
Description
そのため、陰極側から光を取り出す有機EL素子では、有機発光層と、透明導電膜からなる電極との間に、セシウム(Cs)のような仕事関数の低い金属と電子輸送性の有機材料とを混合させた電子注入層を形成することが提案されている。これにより、陰極の電子注入性を高めている。
また、仕事関数が4.0eV以下の低仕事関数金属のイオンのうち少なくとも1種を含む有機金属錯体化合物とアルミニウム(Al)等の熱還元性金属を接触させた層と、酸化モリブデン、ポルフィリン等からなる層の積層体を電子輸送部に形成し、その上に透明導電膜を形成した有機EL素子が開示されている(特許文献2、図19参照)。
さらに、ドナー含有層、アクセプター含有層及び陰極をこの順に設け、ドナー含有層が、ドナー性金属、ドナー性金属化合物及びドナー性金属錯体から選ばれる群のうち少なくとも一種を含有する有機EL素子が開示されている(特許文献3参照)。
しかしながら、蒸着で形成した低仕事関数の金属陰極を使用した素子と比較すると、素子の効率が低下したり、寿命が短くなるという問題があった。
1.陽極、発光層を含む1層以上の有機薄膜層、ドナー含有層、アクセプター含有層及び光透過性陰極をこの順に有し、前記ドナー含有層が、下記式(I)又は(II)で表される化合物を含有する、有機エレクトロルミネッセンス素子。
L1a及びL1bは、それぞれ、単結合又は連結基である。
Ar1a及びAr1bは、それぞれ、置換もしくは無置換の炭素数6~60の芳香族基である。
nは、1~4であり、nが2以上の場合、括弧の内のフェナントロリン骨格を有する基は、同一でも異なっていてもよい。]
図1に本発明に係る有機発光素子の一実施形態の素子構成を示す。
有機EL素子1は、陽極10、正孔注入層20、正孔輸送層30、発光層40、ドナー含有層50、アクセプター含有層60及び光透過性の陰極70を、この順に積層した構成をしている。
ドナー含有層50が無い場合は、アクセプター含有層60と発光層40のアフィニティレベルの差が大きいため、高電圧の印加が必要となる。このためこの素子構成では、陰極に負バイアスを施しても良好に発光することはできない。
本発明は、陰極70と発光層40の間に、アクセプター含有層60とドナー含有層50を設けることにより、電子の輸送を容易にし、有機発光素子の低電圧化、高効率化、長寿命化が図られる。
以下、式(I)及び式(II)の化合物について説明する。
R1a~R7a又はR1b~R7bのうち、隣接するものは互いに結合して環を形成してもよい。環の例としては、ベンゼン環、ナフタレン環、ピラジン環、ピリジン環、フラン環等が挙げられる。
L1a及びL1bは、それぞれ、単結合又は連結基である。連結基としては、置換もしくは無置換の環形成炭素数6~20の芳香族基、置換もしくは無置換の炭素数1~8のアルキレン基、置換もしくは無置換の複素環基が挙げられる。具体的としては、置換もしくは無置換のベンゼン環基、置換もしくは無置換のナフタレン環基、置換もしくは無置換のメチレン基、又は置換もしくは無置換のピリジン環基が好ましい。
Ar1a及びAr1bは、それぞれ、置換もしくは無置換の炭素数6~60の芳香族基である。
nは、1~4であり、nが2以上の場合、括弧の内のフェナントロリン骨格を有する基は、同一でも異なっていてもよい。
R11a~R20a及びR11b~R20bは、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数6~60のアリール基、置換もしくは無置換のピリジル基、置換もしくは無置換のキノリル基、置換もしくは無置換の炭素数1~50のアルキル基、置換もしくは無置換の環形成炭素数3~50のシクロアルキル基、置換もしくは無置換の環形成炭素数7~50のアラルキル基、置換もしくは無置換の炭素数1~50のアルコキシ基、置換もしくは無置換の環形成炭素数6~50のアリールオキシ基、置換もしくは無置換の環形成炭素数5~50のアリールチオ基、置換もしくは無置換の炭素数2~50のアルコキシカルボニル基、置換もしくは無置換の環形成炭素数6~50のアリール基で置換されたアミノ基、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシル基又はカルボキシル基である。
R11a~R20a又はR11b~R20bのうち、隣接するものは互いに結合して環を形成してもよい。環の例としては、ベンゼン環、ナフタレン環、ピラジン環、ピリジン環、フラン環等が挙げられる。
尚、本明細書において、アリール基は、単環の芳香族炭化水素環基及び複数の炭化水素環が縮合した縮合芳香族炭化水素環基を含み、ヘテロアリール基は、単環のヘテロ芳香族環基、並びに複数のヘテロ芳香族環が縮合したヘテロ縮合芳香族環基、及び芳香族炭化水素環とヘテロ芳香族環とが縮合したヘテロ縮合芳香族環基を含む。
「置換もしくは無置換の・・・」の「無置換」とは、水素原子が置換していることを意味し、本発明の一形態に係る化合物における水素原子とは、中性子数が異なる同位体、すなわち、軽水素(protium)、重水素(deuterium)、三重水素(trium)を包含する。
環形成炭素(核炭素)とは、芳香環を構成する炭素原子を意味し、環形成原子(核原子)とは複素環(飽和環、不飽和環及び芳香族複素環を含む)を構成する炭素原子及びヘテロ原子を意味する。
Ar1a及びAr1bが示す芳香族基としては、上述したアリール基及びアリール基から水素原子を除くことにより導かれる二価以上の基が挙げられる。
式(I)及び(II)におけるR1a~R7a及びR1b~R7bとしては、水素、フェニル、ナフチルが好ましい。
アルケニル基としては、上述したアルキル基の分子内に不飽和結合を有する置換基が挙げられる。
アリール基を有するシリル基としては、トリアリールシリル基、アルキルアリールシリル基、トリアルキルシリル基がある。
好適な置換基の例としては、メチル、エチル、プロピル、イソプロピル、ブチル、sec-ブチル、tert-ブチル、シクロヘキシル、フェニル、1-ナフチル、2-ナフチル、トリメチルシリル、トリフェニルシリルが挙げられる。
具体的には、アルカリ金属、アルカリ金属化合物、アルカリ金属を含む有機金属錯体、アルカリ土類金属、アルカリ土類金属化合物、アルカリ土類金属を含む有機金属錯体、希土類金属、希土類金属化合物及び希土類金属を含む有機金属錯体のうち、少なくとも1つを含有する層が好ましい。なかでも、アルカリ金属、アルカリ土類金属、希土類金属の単体、希土類金属の化合物及び希土類金属の錯体のうち、少なくとも1つを含有することが好ましい。
アルカリ土類金属としては、カルシウム(Ca)、マグネシウム(Mg)ストロンチウム(Sr)、バリウム(Ba)等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
希土類金属としては、スカンジウム(Sc)、イットリウム(Y)、セリウム(Ce)、テルビウム(Tb)、イッテルビウム(Yb)等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
以上の金属のうち好ましい金属は、特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子における発光輝度の向上や長寿命化が可能である。
アルカリ土類金属化合物としては、酸化バリウム(BaO)、酸化ストロンチウム(SrO)、酸化カルシウム(CaO)及びこれらを混合したストロンチウム酸バリウム(BaxSr1-xO)(0<x<1)、カルシウム酸バリウム(BaxCa1-xO)(0<x<1)等が挙げられ、BaO、SrO、CaOが好ましい。
希土類金属化合物としては、フッ化イッテルビウム(YbF3)、フッ化スカンジウム(ScF3)、酸化スカンジウム(ScO3)、酸化イットリウム(Y2O3)、酸化セリウム(Ce2O3)、フッ化ガドリニウム(GdF3)、フッ化テルビウム(TbF3)等が挙げられ、YbF3、ScF3、TbF3が好ましい。
尚、本発明の一形態に係る有機発光素子は図1に示す構成に限定されない。例えば、正孔輸送層、正孔注入層は任意の層であるため省略することが可能であり、また、発光層とドナー含有層の間に電子輸送層等を設けることができる。正孔輸送層、正孔注入層、発光層、電子輸送層等が本発明の一形態に係る有機薄膜層に相当する。
また、陰極とアクセプター含有層の間にバッファー層を形成してもよい。バッファー層については、特許第4392050号を参照できる。
また、陽極と陰極との間に、少なくとも発光層を有する有機層からなる複数の発光ユニットを、電荷発生層を介して重ねて配置した構成を有する有機EL素子(MPE素子)にも使用できる。
化合物の還元しやすさは、還元電位で測定することができる。本発明では飽和カロメル(SCE)電極を参照電極とした還元電位において、好ましくは-0.8V以上、より好ましくは-0.3V以上であり、特に好ましくはテトラシアノキノジメタン(TCNQ)の還元電位(約0V)より大きな値を持つ化合物が好ましい。
式(III)の化合物の具体例を以下に示す。
シクロアルキル基としてはシクロペンチル基、シクロヘキシル基等が挙げられる。
アルケニル基としてはビニル基、プロペニル基(二重結合の位置異性体を含む)、ブテニル基(二重結合の位置異性体を含む)、ペンテニル基(二重結合の位置異性体を含む)等があげられる。
(置換)アリール基としては、フェニル基、ビフェニル基、ナフチル基、フルオロフェニル基、トリフルオロメチルフェニル基、(トリフルオロメチル)フルオロフェニル基、トリフルオロフェニル基、ビス(トリフルオロメチル)フェニル基、(トリフルオロメチル)ジフルオロフェニル基、トリフルオロメトキシフェニル基、トリフルオロメトキシフルオロフェニル基等が挙げられる。
複素環基としては、ピリジン、ピラジン、フラン、イミダゾール、ベンズイミダゾール、チオフェン等の残基が挙げられる。
フルオロアルキル基としては、トリフルオロメチル基、ペンタフルオロエチル基、パーフルオロシクロヘキシル基、パーフルオロアダマンチル基等が挙げられる。
アルコキシ基としては、メトキシ基、エトキシ基等が挙げられる。
フルオロアルコキシ基としては、トリフルオロメトキシ基、ペンタフルオロエトキシ基、2,2,2-トリフルオロエトキシ基、2,2,3,3,3-ペンタフルオロプロポキシ基、2,2,3,3-テトラフルオロプロポキシ基、1,1,1,3,3,3-ヘキサフルオロプロパン‐2-イルオキシ基等が挙げられる。
(置換)アリールオキシ基の例としては、フェニルオキシ基、ペンタフルオロフェニルオキシ基、4-トリフルオロフェニルオキシ基等が挙げられる。
(置換)アラルキルオキシ基の例としては、ベンジルオキシ基、ペンタフルオロベンジルオキシ基、4-トリフルオロメチルベンジルオキシ基等が挙げられる。
(置換)アミノ基の例としては、アミノ基、モノもしくはジメチルアミノ基、モノもしくはジエチルアミノ基、モノもしくはジフェニルアミノ基等が挙げられる。
(置換)シリル基の例としては、シリル基、モノ、ジもしくはトリメチルシリル基、モノ、ジもしくはトリエチルシリル基、モノ、ジもしくはトリフェニルシリル基等が挙げられる。
尚、以下、特筆しない限り“置換もしくは無置換”というときの任意の置換基の例としては、上記で挙げたハロゲン原子、シアノ基、アルキル基、アリール基、フルオロアルキル基、フルオロアルコキシ基及び複素環基が挙げられる。
さらに、R1~R4の少なくとも一つは、フッ素原子、フルオロアルキル基、フルオロアルコキシ基、シアノ基、又は、フッ素、フルオロアルキル基、フルオロアルコキシ基、シアノ基から選ばれる少なくとも1種の基を有するアリール基もしくは複素環基であることが好ましい。これらを置換基にすることで電子受容性を高めたり、適度な昇華温度を得られたり、あるいは結晶化を抑制したりすることができる。
また、Y1~Y4のうち少なくとも1つは窒素原子であることが好ましい(後述のY21~Y26及びY31~Y38についても同様)。少なくとも1つは窒素原子であることで、電子受容性を高めたり、耐熱性を高めたり、あるいは結晶化を抑制したりすることができる。
アクセプター含有層における、式(IV)で表される化合物の含有率は、0.1重量%~100重量%であることが好ましく、特に、10重量%~70重量%であることが好ましい。
本実施形態の有機EL素子2は、基板10上に、陽極20、第1の発光ユニット81、電荷発生層82、第2の発光ユニット83、ドナー含有層50、アクセプター含有層60及び光透過性陰極70を、この順に備える。
2つの発光ユニットはそれぞれ、少なくとも発光層を有する単層又は積層構造を有する。例えば、発光ユニットは陽極側から、正孔輸送層、発光層及び電子輸送層を積層した多層膜構造が好ましい。
本実施形態では、例えば、各発光ユニットの発光色を異ならせること、即ち発光層の材料を変えることにより、白色発光する有機EL素子が得られる。
30mm×30mmのガラス板からなる基板上に、陽極としてITOを240nmの膜厚で形成した。次に、SiO2蒸着により2mm×2mmの発光領域以外を絶縁膜でマスクした有機EL素子用のセルを作製した。
陽極上に、正孔注入層として、ヘキサニトリルアザトリフェニレン(下記式(HAT))を10nmの膜厚で形成した。
正孔注入層上に、正孔輸送層、青色発光層及び電子輸送層をこの順に形成した。
具体的に、正孔輸送層として下記式(α-NPD)を真空蒸着法により90nm(蒸着速度0.2~0.4nm/sec)の膜厚で形成した。
続いて、正孔輸送層上に、青色発光層を形成した。発光層のホストには下記式(1)の化合物を、ドーパントには下記式(2)の化合物を使用した。ドーパントの添加量が膜厚比で5%となるように真空蒸着し膜厚30nmの発光層とした。
次いで、青色発光層上に、電子輸送層として、下記式(Alq3)を30nmの膜厚で形成した。
次いで、電子輸送層上に、ドナー含有層及びアクセプター含有層を表1に示す化合物を用いてこの順に形成した。ドナー含有層は表1の化合物とLiの混合層である(表1の「%」は、膜厚比に対する値である。)。
アクセプター含有層上に、表1に示す陰極(ITO又はIZO:膜厚200nm)をスパッタリングにて形成し、有機EL素子を作製した。
結果を表1に示す。
電子輸送層(Alq3層)までは、実施例1と同様に形成した。その後、ドナー含有層として、Alq3とMgの混合層(Mg:2%)を膜厚40nmで形成した。
ドナー含有層上に陰極(ITO:200nm)を形成し、有機EL素子を作製した。実施例と同様に評価した結果を表1に示す。
電子輸送層(Alq3層)までは、実施例1と同様に形成した。その後、ドナー含有層及びアクセプター含有層を形成せずに、電子注入層としてLiFを1nmの厚さで形成した。その後、LiF上に陰極(ITO:200nm)を形成し、有機EL素子を作製した。実施例と同様に評価した結果を表1に示す。
陰極をITOに変えてMg-Ag合金にし、膜厚を10nmとした他は、比較例2と同様にして有機EL素子を作製し評価した。結果を表1に示す。
LiF層に変えて、銅フタロシアニン錯体(CuPc)10nmとLi1nmの積層体とした他は、比較例2と同様にして有機EL素子を作製し評価した。結果を表1に示す。
電子輸送層(Alq3層)までは、実施例1と同様に形成した。その後、Alq3とMgの混合層(Mg:2%)を膜厚20nmで形成した。次いで、Al層を膜厚2nmで形成し、さらに、その上に、MoO3層を10nmで形成した。その後、MoO3層上に陰極(ITO:200nm)を形成し、有機EL素子を作製した。実施例と同様に評価した結果を表1に示す。
ドナー含有層を下記のBphenとLiの混合層(Li:2%)とし、アクセプター含有層をHATとし、陰極をIZOに変えた他は、実施例1と同様にして有機EL素子を作製し評価した。結果を表1に示す。
一方、比較例1、2、4に関しては、本発明の一形態に係るドナー含有層及びアクセプター含有層がないため、電子供給不足と陰極形成時のダメージが生じ、素子の高電圧化、低効率化、短寿命化が生じた。比較例3では、MgAg陰極による発光吸収に起因した素子の低効率化が生じた。
比較例5では、Al金属層を挿入したため発光吸収が生じたことから素子が低効率化し、また、アクセプター含有層による電子供給不足による高電圧化、短寿命化が生じた。
比較例6、7では、ドナー含有層の化合物が不安定であるため短寿命化し、また、電子引き抜き性の不足により高電圧化が生じた。
この明細書に記載の文献及び本願のパリ優先の基礎となる日本出願明細書の内容を全てここに援用する。
Claims (9)
- 陽極、発光層を含む1層以上の有機薄膜層、ドナー含有層、アクセプター含有層及び光透過性陰極をこの順に有し、
前記ドナー含有層が、下記式(I)又は(II)で表される化合物を含有する、有機エレクトロルミネッセンス素子。
L1a及びL1bは、それぞれ、単結合又は連結基である。
Ar1a及びAr1bは、それぞれ、置換もしくは無置換の炭素数6~60の芳香族基である。
nは、1~4であり、nが2以上の場合、括弧の内のフェナントロリン骨格を有する基は、同一でも異なっていてもよい。] - 前記式(I)又は(II)で表される化合物が、下記式(I-a)、(I-b)、(II-a)又は(II-b)で表される化合物である、請求項1に記載の有機エレクトロルミネッセンス素子。
R11a~R20a及びR11b~R20bは、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数6~60のアリール基、置換もしくは無置換のピリジル基、置換もしくは無置換のキノリル基、置換もしくは無置換の炭素数1~50のアルキル基、置換もしくは無置換の環形成炭素数3~50のシクロアルキル基、置換もしくは無置換の環形成炭素数7~50のアラルキル基、置換もしくは無置換の炭素数1~50のアルコキシ基、置換もしくは無置換の環形成炭素数6~50のアリールオキシ基、置換もしくは無置換の環形成炭素数5~50のアリールチオ基、置換もしくは無置換の炭素数2~50のアルコキシカルボニル基、置換もしくは無置換の環形成炭素数6~50のアリール基で置換されたアミノ基、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシル基又はカルボキシル基であるか、R11a~R20a又はR11b~R20bのうち、隣接するものは互いに結合して環を形成する。
L1a及びL1bは、それぞれ単結合又は連結基である。] - 前記ドナー含有層が、電子供与性金属、金属化合物及び金属錯体の少なくとも1つを含有する、請求項1又は2に記載の有機エレクトロルミネッセンス素子。
- 前記ドナー含有層が、アルカリ金属、アルカリ土類金属、希土類金属の単体、希土類金属の化合物及び希土類金属の錯体のうち、少なくとも1つを含有する、請求項3に記載の有機エレクトロルミネッセンス素子。
- 前記アクセプター含有層が、下記式(III)で表される化合物を含有する、請求項1~4のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記アクセプター含有層が、下記式(IV)で表される化合物を含有する、請求項1~4のいずれかに有機エレクトロルミネッセンス素子。
Rg1及びRg2は、それぞれ互いに同一でも異なっていてもよく、下記式(i)もしくは(ii)である。
R1~R4は、それぞれ互いに同一でも異なっていてもよく、水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のシクロアルキル基、置換もしくは無置換のアルケニル基、置換もしくは無置換のアリール基、置換もしくは無置換の複素環基、ハロゲン原子、置換もしくは無置換のフルオロアルキル基、置換もしくは無置換のアルコキシ基、置換もしくは無置換のフルオロアルコキシ基、置換もしくは無置換のアリーロキシ基、置換もしくは無置換のアラルキルオキシ基、置換もしくは無置換のアミノ基、置換もしくは無置換のシリル基又は、シアノ基であるか、R1とR2及びR3とR4は互いに結合して環を形成する。
Y1~Y4は互いに同一でも異なっていてもよく、それぞれはN、CH、又はC(R5)であり、R5は前記R1~R4と同義である。] - 前記発光層を含む1層以上の有機薄膜層が、電荷発生層を介して積層された2以上の発光ユニットを構成している、請求項1~6のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記発光ユニットの発光層を構成する少なくとも1つの材料が、他の発光ユニットの発光層を構成する材料と異なっている、請求項7に記載の有機エレクトロルミネッセンス素子。
- 白色発光する、請求項1~8のいずれかに記載の有機エレクトロルミネッセンス素子。
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Also Published As
Publication number | Publication date |
---|---|
US9978975B2 (en) | 2018-05-22 |
US20150069351A1 (en) | 2015-03-12 |
EP2833429A1 (en) | 2015-02-04 |
JPWO2013145667A1 (ja) | 2015-12-10 |
EP2833429B1 (en) | 2019-09-18 |
EP2833429A4 (en) | 2016-01-06 |
JP6480730B2 (ja) | 2019-03-13 |
TW201403904A (zh) | 2014-01-16 |
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