WO2009084585A1 - 芳香族ジアミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
芳香族ジアミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2009084585A1 WO2009084585A1 PCT/JP2008/073593 JP2008073593W WO2009084585A1 WO 2009084585 A1 WO2009084585 A1 WO 2009084585A1 JP 2008073593 W JP2008073593 W JP 2008073593W WO 2009084585 A1 WO2009084585 A1 WO 2009084585A1
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- group
- substituted
- carbon atoms
- unsubstituted
- aromatic diamine
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- 150000004984 aromatic diamines Chemical class 0.000 title claims abstract description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 186
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 20
- 239000010409 thin film Substances 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 56
- 238000005401 electroluminescence Methods 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000005581 pyrene group Chemical group 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001721 carbon Chemical class 0.000 claims description 5
- 150000001454 anthracenes Chemical class 0.000 claims description 4
- 125000005567 fluorenylene group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 150000003220 pyrenes Chemical class 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 15
- 125000003277 amino group Chemical group 0.000 abstract description 5
- 125000005578 chrysene group Chemical group 0.000 abstract description 2
- -1 distyryl compound Chemical class 0.000 description 388
- 230000015572 biosynthetic process Effects 0.000 description 72
- 238000003786 synthesis reaction Methods 0.000 description 71
- 239000010410 layer Substances 0.000 description 70
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000000843 powder Substances 0.000 description 16
- 238000005259 measurement Methods 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 5
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 5
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 5
- 125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 description 5
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 5
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 5
- 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 description 5
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 5
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- 125000006481 2-iodobenzyl group Chemical group [H]C1=C([H])C(I)=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 3
- 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 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
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- 230000005611 electricity Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- RULVBMDEPWAFIN-UHFFFAOYSA-N 6,12-dibromochrysene Chemical compound C1=CC=C2C(Br)=CC3=C(C=CC=C4)C4=C(Br)C=C3C2=C1 RULVBMDEPWAFIN-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002078 anthracen-1-yl 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 2
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- ILSGDBURWYKYHE-UHFFFAOYSA-N chrysene-1,2-diamine Chemical class C1=CC=CC2=CC=C3C4=CC=C(N)C(N)=C4C=CC3=C21 ILSGDBURWYKYHE-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 239000004814 polyurethane Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 229910052709 silver Inorganic materials 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/78—Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/14—Perylene derivatives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/001—Pyrene dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/008—Dyes containing a substituent, which contains a silicium atom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
Definitions
- the present invention relates to an aromatic diamine derivative and an organic electroluminescence device using the same, and more particularly to an organic electroluminescence device having a long lifetime and high luminous efficiency, and an aromatic diamine derivative that realizes the organic luminescence device.
- an organic electroluminescence (EL) element using an organic substance is expected to be used as an inexpensive large-area full-color display element of a solid light emitting type and has been developed in many ways.
- an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Furthermore, this is a phenomenon in which electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
- Patent Document 4 a technique using a mono- or bisanthracene compound and a distyryl compound as an organic light-emitting medium layer is disclosed (see Patent Document 4). Furthermore, a blue light-emitting element using a diaminochrysene derivative is disclosed (see Patent Document 5).
- an invention using an aromatic amine derivative having an arylene group at the center as a hole transporting material (see Patent Document 6), a dibenzofuran ring, a dibenzothiophene ring, a benzofuran ring, a benzothiophene ring, and the like are attached to a nitrogen atom via an arylene group
- An invention using a bonded aromatic amine derivative as a hole transporting material (see Patent Document 7) is also disclosed.
- an invention is disclosed in which an aromatic diamine derivative in which a phenyl group having a substituted or unsubstituted silyl group is substituted with a nitrogen atom is used as a light emitting layer material.
- the organic light-emitting material described in Patent Document 1 for example, at a current density of 165 mA / cm 2 , only a luminance of 1650 cd / m 2 is obtained, and the efficiency is 1 cd / A, which is extremely low and not practical. Also, the organic light emitting material described in Patent Document 2 has a low efficiency of about 1 to 3 cd / A, and further improvement for practical use is necessary. Even with the method described in Patent Document 3, there is room for further improvement rather than a long life that can withstand practical use.
- the technique described in Patent Document 4 has a problem that the emission spectrum becomes longer due to the conjugated structure of the styryl compound and the color purity is poor.
- the present invention has been made to solve such a problem, and an object of the present invention is to provide an organic EL device having a long lifetime and high luminous efficiency and a compound for realizing the organic EL device.
- an aromatic diamine derivative having a chrysene structure has a phenyl group having a substituted or unsubstituted silyl group as a substituent of an amino group. It has been found that when the aromatic amine derivative is used as a light emitting material, it has high luminous efficiency and long life. The present invention has been completed based on such findings.
- the present invention is an aromatic diamine derivative represented by the following general formula (I).
- R 1 to R 10 each independently represents a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, an aralkyl group having 7 to 50 carbon atoms, or 6 carbon atoms
- R 11 represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted carbon group having 7 to 50 carbon atoms
- 50 represents an aralkyl group, a substituted or unsubstituted alkyloxy group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and at least one of A, B, and C is substituted.
- an unsubstituted silyl group the remainder being a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted carbon number 7-5
- B and C are trimethylsilyl groups and b and c are 1 and both are para-substituted, and A and R 11 are methyl groups, a and d are both 1 and both are para-substituted. except for.
- A is a trimethylsilyl group and a is 1 and is para-substituted
- R 11 is a methyl group and d is 2 and two R 11 are both meta-substituted
- B is a trimethylsilyl group and b is 1 and para-substituted
- a structure in which C is a methyl group, c is 2 and two C are both meta-substituted.
- the present invention provides an organic EL device in which an organic thin film layer comprising at least one light emitting layer or a plurality of light emitting layers is sandwiched between a cathode and an anode, and at least one of the organic thin film layers contains the aromatic diamine derivative.
- the organic EL element contained alone or as a component of a mixture is provided.
- an organic EL device using the aromatic diamine derivative has high luminous efficiency, maintains blue purity, hardly deteriorates even when used for a long time, and has a long life.
- the aromatic amine derivative of the present invention is an aromatic diamine derivative represented by the following general formula (I).
- R 1 to R 10 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, an aralkyl group having 7 to 50 carbon atoms, Represents an aryl group having 6 to 50 carbon atoms.
- the number of carbon atoms of each group in the general formula is a number that does not include the carbon number of the substituent.
- alkyl group having 1 to 50 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, various pentyl groups (“various "Represents any of straight chain, branched chain, and cyclic. The same shall apply hereinafter.), And an alkyl group having 1 to 10 carbon atoms is preferred.
- Examples of the cycloalkyl group having 3 to 50 carbon atoms include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a cyclooctyl group, and a cyclohexyl group having 5 to 8 carbon atoms is preferable.
- Examples of the aralkyl group having 7 to 50 carbon atoms include benzyl group, ⁇ , ⁇ -phenylmethylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenoxybenzyl group, ⁇ , ⁇ -methylphenylbenzyl group, ⁇ , ⁇ -ditrifluoromethylbenzyl group, triphenylmethyl group, ⁇ -benzyloxybenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group , ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthy
- aryl group having 6 to 50 carbon atoms examples include phenyl group, tolyl group, naphthyl group, acenaphthylenyl group, anthryl group, phenanthryl group, phenalenyl group, fluorenyl group, a-indacenyl group, and as-indacenyl group.
- An aryl group having a number of 6 to 14 is preferred.
- At least one of A, B, and C represents a substituted or unsubstituted silyl group, and the remainder is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group.
- An unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted alkyloxy group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number 6 Represents up to 50 aryl groups.
- Examples of the substituent for the silyl group include an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 14 carbon atoms, and an alkoxyl group having 1 to 20 carbon atoms.
- Examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and various pentyl groups.
- an alkyl group having 1 to 5 carbon atoms is preferred.
- Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group, a tolyl group, a naphthyl group, and an anthryl group, and an aryl group having 6 to 10 carbon atoms is preferable.
- Examples of the alkoxyl group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, various propoxy groups, and various butoxy groups, and an alkoxyl group having 1 to 5 carbon atoms is preferable.
- the silyl group is more preferably a trialkylsilyl group, a dialkyl-monoarylsilyl group, a monoalkyl-diarylsilyl group, or a triarylsilyl group.
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by the remaining group other than silyl group among A, B and C include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n -Butyl group, isobutyl group, s-butyl group, t-butyl group and various pentyl groups are exemplified, and an alkyl group having 1 to 10 carbon atoms is preferable.
- Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a cyclooctyl group.
- a cyclohexyl group having 5 to 8 carbon atoms is exemplified. preferable.
- Examples of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms include benzyl group, ⁇ , ⁇ -phenylmethylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenoxybenzyl group, ⁇ , ⁇ -methylphenylbenzyl.
- the substituted or unsubstituted alkyloxy group having 1 to 50 carbon atoms is a group represented by —OY, and the Y is a group other than the above-mentioned “A, B, C, which is not a silyl group. And the same as the alkyl group represented by the “substituted or unsubstituted alkyl group having 1 to 50 carbon atoms”. Among these, an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 5 carbon atoms is more preferable, and a methyl group is further preferable.
- Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms include phenyl group, tolyl group, methoxyphenyl group, ethoxyphenyl group, butoxyphenyl group, naphthyl group, acenaphthylenyl group, anthryl group, phenanthryl group, phenalenyl group, Examples include a fluorenyl group, an a-indacenyl group, and an as-indacenyl group.
- R 11 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted
- a substituted alkyloxy group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms is represented.
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, Examples thereof include various pentyl groups, and alkyl groups having 1 to 10 carbon atoms are preferable.
- Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a cyclooctyl group.
- a cyclohexyl group having 5 to 8 carbon atoms is exemplified. preferable.
- Examples of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms include benzyl group, ⁇ , ⁇ -phenylmethylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenoxybenzyl group, ⁇ , ⁇ -methylphenyl Benzyl group, ⁇ , ⁇ -ditrifluoromethylbenzyl group, triphenylmethyl group, ⁇ -benzyloxybenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl -T-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group
- the substituted or unsubstituted alkyloxy group having 1 to 50 carbon atoms is a group represented by —OY ′, and as Y ′, among the above “A, B, and C, the remaining silyl group is not a silyl group.
- an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 5 carbon atoms is more preferable, and a methyl group is further preferable.
- Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms include phenyl group, tolyl group, naphthyl group, acenaphthylenyl group, anthryl group, phenanthryl group, phenalenyl group, fluorenyl group, a-indacenyl group, as-indacenyl group An aryl group having 6 to 14 carbon atoms is preferable.
- A is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms.
- An aromatic diamine derivative which is a 7 to 50 aralkyl group, a substituted or unsubstituted alkyloxy group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms is preferred. Arbitrariness. As the aromatic diamine derivative represented by the general formula (I), an aromatic diamine derivative in
- Examples of the aromatic diamine derivative represented by the general formula (I) include the following. Note that —SiMe 3 represents a trimethylsilyl group.
- A is a trimethylsilyl group and a is 1 and para-substituted
- R 11 is a methyl group and d is 2 and both are meta-substituted
- B is a trimethylsilyl group
- b is 1 and para-substituted
- C is a methyl group
- c is 2 and both are meta-substituted structures, that is, the following compounds are excluded.
- the method for producing the aromatic diamine derivative represented by the general formula (I) of the present invention is not particularly limited and may be produced by a known method.
- the aromatic diamine derivative of the present invention is suitable as a material for an organic EL device, particularly preferably a light emitting material, and suitably used as a blue light emitting material or a green light emitting material. Moreover, the aromatic diamine derivative of the present invention is more suitable as a doping material for organic EL devices.
- the organic EL device of the present invention is a device in which one or more organic thin film layers are formed between an anode and a cathode.
- a light emitting layer is provided between the anode and the cathode.
- the light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material.
- the aromatic diamine derivative of the present invention has high light emission characteristics and has excellent hole injection properties, hole transport properties and electron injection properties, and electron transport properties. Can be used.
- the light emitting layer preferably contains the aromatic diamine derivative of the present invention, and the content is usually preferably 0.1 to 20% by mass, more preferably 1 to 10% by mass, 3 to 7% by mass is more preferable.
- the aromatic diamine derivative of the present invention has extremely high fluorescence quantum efficiency, high hole transport ability and electron transport ability, and can form a uniform thin film. Therefore, the light emitting layer can be formed only with this aromatic diamine derivative. It is also possible to form.
- the organic EL device of the present invention is an organic EL device in which an organic thin film layer composed of at least two layers including at least a light emitting layer is sandwiched between a cathode and an anode. It is also preferable to have an organic layer mainly composed of an aromatic diamine derivative. Examples of the organic layer include a hole injection layer and a hole transport layer.
- aromatic diamine derivative of the present invention when used as a doping material, a known compound can be used as the host material, and there is no particular limitation.
- an anthracene derivative of the following general formula (i) and / or the following general formula (ii) It is more preferable to use a pyrene derivative of
- R 12 to R 19 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms, substituted or unsubstituted, An unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group (aryl)
- the moiety is 6 to 50 carbon atoms, the alkyl moiety is 1 to 50 carbon atoms), a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 carbon atoms, substituted or unsubstituted
- Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms of R 12 to R 19 in the general formula (i) include, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, and a 2-anthryl group.
- Examples of the substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms of R 12 to R 19 in the general formula (i) include, for example, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2- Pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1- Isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3- Benzofuranyl group, 4-
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R 12 to R 19 in the general formula (i) include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, and s-butyl group.
- Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms of R 12 to R 19 in the general formula (i) include, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, 1 -Adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group.
- the alkyl group part of the substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms of R 12 to R 19 in the general formula (i) is the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R 12 to R 19. Selected from the group.
- Examples of the substituted or unsubstituted aralkyl group (the aryl part has 6 to 50 carbon atoms and the alkyl part has 1 to 50 carbon atoms) as a substituent of R 12 to R 19 in the general formula (i) include, for example, a benzyl group, 1- Phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -n
- R 12 aryl group moiety of the substituted or unsubstituted aryloxy group and arylthio group having 6 to 50 carbon atoms ⁇ R 19 are carbon atoms each substituted or unsubstituted wherein R 12 ⁇ R 19 in the general formula (i) Selected from 6 to 50 aryl groups.
- Examples of the substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms of R 12 to R 19 in the general formula (i) include a methoxycarbonyl group, an ethoxycarbonyl group, various propoxycarbonyl groups, and various butoxycarbonyl groups.
- An alkoxycarbonyl group having 1 to 20 carbon atoms is preferable.
- Examples of the substituted silyl group of R 12 to R 19 in the general formula (i) include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group. It is done.
- Examples of the halogen atom represented by R 12 to R 19 in the general formula (i) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Examples of the substituent on the aromatic ring represented by R 12 to R 19 include a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 1 to 30 carbon atoms, and 3 to 3 carbon atoms.
- cycloalkyl groups C1-C10 alkoxyl groups, C5-C30 aromatic heterocyclic groups, C7-C30 aralkyl groups, C6-C30 aryloxy groups, C6-C6 It may be further substituted with a 30 arylthio group, an alkoxycarbonyl group having 2 to 10 carbon atoms, or a carboxyl group.
- D and E are each independently a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms.
- the aromatic ring may be substituted with one or more substituents.
- substituents of the aromatic ring include a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted cyclohexane having 3 to 50 carbon atoms.
- the substituents may be the same or different, and adjacent substituents are bonded to each other to form a saturated or unsaturated cyclic structure. It may be formed.
- at least one of D and E is preferably a substituent having a substituted or unsubstituted condensed ring group having 10 to 30 carbon atoms, more preferably a substituent having a substituted or unsubstituted naphthyl group. preferable. Note that D and E are preferably different.
- Examples of the group derived from a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms of D and E include, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p- Terphenyl-2-yl, m-terphenyl-4-y
- a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.
- the substituent on the aromatic ring of D and E include a halogen atom, hydroxyl group, nitro group, cyano group, alkyl group having 1 to 10 carbon atoms, aryl group having 1 to 30 carbon atoms, and 3 to 20 carbon atoms.
- Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- L 1 and L 2 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group.
- s is an integer from 0 to 2
- p is an integer from 1 to 4
- q is an integer from 0 to 2
- r is an integer from 0 to 4.
- L 1 or Ar 1 is bonded to any one of 1 to 5 positions of pyrene, and L 2 or Ar 2 is bonded to any of 6 to 10 positions of pyrene.
- Ar 1 , Ar 2 , L 1 and L 2 satisfy the following (1) or (2).
- Ar 1 ⁇ Ar 2 and / or L 1 ⁇ L 2 (where ⁇ indicates a group having a different structure)
- Examples of the aryl group having 6 to 50 carbon atoms represented by Ar 1 and Ar 2 include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, acenaphthylenyl group, anthryl group, phenanthryl group, phenenyl group, fluorenyl group, a -Indacenyl group, as-indacenyl group. Particularly preferred is an aryl group having 6 to 30 carbon atoms.
- Examples of the substituent which the phenylene group, naphthalenylene group, fluorenylene group and dibenzosilolylene group represented by L 1 and L 2 may have include, for example, an alkyl group having 1 to 50 carbon atoms and a cycloalkyl group having 3 to 50 carbon atoms.
- aralkyl group having 7 to 50 carbon atoms, alkoxyl group having 1 to 50 carbon atoms, aryl group having 6 to 50 carbon atoms, aryloxy group having 6 to 50 carbon atoms, arylthio group having 6 to 50 carbon atoms, carbon number 1 to 50 alkoxycarbonyl groups, amino groups, halogen atoms, nitro groups, hydroxyl groups, carboxyl groups or cyano groups are represented.
- alkyl group having 1 to 50 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and various pentyl groups.
- An alkyl group having 1 to 10 carbon atoms is preferable.
- Examples of the cycloalkyl group having 3 to 50 carbon atoms include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a cyclooctyl group, and a cyclohexyl group having 5 to 8 carbon atoms is preferable.
- Examples of the aralkyl group having 7 to 50 carbon atoms include benzyl group, ⁇ , ⁇ -phenylmethylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenoxybenzyl group, ⁇ , ⁇ -methylphenylbenzyl group, ⁇ , ⁇ -ditrifluoromethylbenzyl group, triphenylmethyl group, ⁇ -benzyloxybenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group , ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthy
- alkoxyl group having 1 to 50 carbon atoms examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, and t-butoxy group. 1 to 10 alkoxyl groups are preferred.
- aryl group having 6 to 50 carbon atoms include a phenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a phenanthryl group, a phenalenyl group, a fluorenyl group, an a-indacenyl group, and an as-indacenyl group.
- aryl groups are preferred.
- the aryloxy group having 6 to 50 carbon atoms include a phenoxy group and a naphthyloxy group, and an aryloxy group having 6 to 20 carbon atoms is preferable.
- the arylthio group having 6 to 50 carbon atoms include a phenylthio group and a naphthylthio group, and an arylthio group having 6 to 20 carbon atoms is preferable.
- Examples of the alkoxycarbonyl group having 1 to 50 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, various propoxycarbonyl groups, and various butoxycarbonyl groups, and an alkoxycarbonyl group having 1 to 20 carbon atoms is preferable.
- Examples of the amino group include an amino group substituted with an alkyl group having 1 to 50 carbon atoms such as a dimethylamino group, a diethylamino group, a diphenylamino group, and a dinaphthylamino group or an aryl group having 6 to 50 carbon atoms.
- Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- anthracene derivative represented by the general formula (i) used in the organic EL device of the present invention include those in the molecule shown in paragraphs [0043] to [0063] of JP-A No. 2004-356033.
- Examples include various anthracene derivatives known in the art such as those having two anthracene skeletons and compounds having one anthracene skeleton shown in pages 27 to 28 of WO 2005/061656. Typical specific examples are shown below, but are not particularly limited thereto.
- organic EL elements having a plurality of organic thin film layers are, for example, (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / positive). And a layer laminated with a structure such as hole injection layer / light emitting layer / electron injection layer / cathode).
- the organic EL element can prevent the brightness
- a known light emitting material, doping material, hole injecting material, and electron injecting material can also be used for the plurality of layers as necessary.
- the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers.
- the layer that injects holes from the electrode is a hole injection layer
- the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer.
- an electron injection layer a layer that injects electrons from an electrode
- a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
- Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
- Examples of host materials or doping materials other than the above general formulas (i) and (ii) that can be used in the light emitting layer together with the aromatic diamine derivative of the present invention include known materials such as naphthalene, phenanthrene, rubrene, anthracene, Tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis Condensed polycyclic aromatic compounds such as (9′-ethynylanthracenyl) benzene and their derivatives, tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinate) )
- the hole injection material has the ability to transport holes, has a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and excitons generated in the light emitting layer.
- a compound that prevents movement to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable.
- phthalocyanine derivatives naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl Examples include alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers. However, it is not limited to these.
- more effective hole injection materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
- aromatic tertiary amine derivatives include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4, 4′-diamine, N, N, N ′, N ′-(4-methylphenyl) -1,1′-phenyl-4,4′-diamine, N, N, N ′, N ′-(4-methyl Phenyl) -1,1'-biphenyl-4,4'-diamine, N, N'-diphenyl-N, N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N, N'- (Methylpheny
- phthalocyanine (Pc) derivative examples include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc—O—GaPc.
- the organic EL device of the present invention is a layer containing these aromatic tertiary amine derivatives and / or phthalocyanine derivatives, for example, the hole transport layer or the hole injection layer, between the light emitting layer and the anode. Is preferably formed.
- an electron injection material it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, and a hole injection layer of excitons generated in the light emitting layer
- the compound which prevents the movement to and is excellent in thin film forming ability is preferable.
- it is not limited to these.
- it can be sensitized by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.
- more effective electron injection materials are metal complex compounds and nitrogen-containing five-membered ring derivatives.
- the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, and tris.
- nitrogen-containing five-membered derivative for example, oxazole, thiazole, oxadiazole, thiadiazole, and triazole derivatives are preferable.
- the organic EL device of the present invention in the light emitting layer, in addition to the aromatic diamine derivative represented by the general formula (I), at least a known light emitting material, doping material, hole injecting material, and electron injecting material. One kind may be contained in the same layer.
- a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.
- a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
- Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like.
- alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto.
- the ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.
- the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device.
- the substrate is also preferably transparent.
- the transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering.
- the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
- the substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
- Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone.
- each layer of the organic EL device For the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to.
- the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
- the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
- the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like to form a thin film, and any solvent may be used.
- an appropriate resin or additive may be used for improving film formability and preventing pinholes in the film.
- Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl.
- Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole.
- the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
- the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
- the material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.
- Synthesis Example 4 Synthesis of Compound (D-4)
- Synthesis Example 7 Synthesis of Compound (D-7)
- Synthesis Example 15 Synthesis of Compound (D-15)
- N- [4- (trimethylsilyl) phenyl)]-Np-tolylamine N- [4- (trimethylsilyl) phenyl)] Synthesis was performed in the same manner as in Synthesis Example 1 except that -N-5- (2,3-dihydro-1H-indenyl) amine was used.
- Example 1 A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a size of 25 ⁇ 75 ⁇ 1.1 mm. After cleaning the glass substrate by irradiating with ultraviolet rays and ozone, the substrate was placed in a vacuum deposition apparatus.
- N ′, N ′′ -bis [4- (diphenylamino) phenyl] -N ′, N ′′ -diphenylbiphenyl-4,4′-diamine was deposited to a thickness of 60 nm
- N, N, N ′, N′-tetrakis (4-biphenyl) -4,4′-benzidine was deposited to a thickness of 20 nm as a hole transport layer.
- Example 2 An organic EL device was produced in the same manner as in Example 1 except that the compound (D-2) was used instead of the compound (D-1) as a doping material.
- the obtained organic EL element was subjected to a current test, pure blue light emission (emission wavelength: 457 nm) of 500 cd / m 2 was obtained at a voltage of 6.5 V and a current density of 10 mA / m 2 .
- the continuous electricity test was done like Example 1, the half life was 2200 hours.
- Example 3 an organic EL device was produced in the same manner as in Example 1 except that the compound (D-3) was used instead of the compound (D-1) as a doping material.
- the obtained organic EL element was subjected to a current test, pure blue light emission (emission wavelength: 457 nm) of 500 cd / m 2 was obtained at a voltage of 6.5 V and a current density of 10 mA / m 2 .
- the continuous electricity test was done like Example 1, the half life was 2300 hours.
- Example 1 ⁇ Comparative Example 1> In Example 1, except that 6,12-N, N ′-[tetrakis (4-trimethylsilylphenyl)] diaminochrysene was used as the doping material instead of the compound (D-1), Similarly, an organic EL device was produced. When the obtained organic EL element was subjected to an energization test, 300 cd / m 2 of pure blue light emission (emission wavelength: 452 nm) was obtained at a voltage of 6.5 V and a current density of 10 mA / m 2 . Moreover, when the continuous electricity test was done like Example 1, the half life was 1500 hours.
- the organic EL device using the aromatic diamine derivative of the present invention has high luminous efficiency, is hardly deteriorated even when used for a long time, and has a long life. For this reason, it is useful as a light source such as a flat light emitter of a wall-mounted television and a backlight of a display.
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Abstract
Description
従来の有機EL素子は、無機発光ダイオードに比べて駆動電圧が高く、発光輝度や発光効率も低かった。また、特性劣化も著しく実用化には至っていなかった。最近の有機EL素子は徐々に改良されているものの、引き続き、さらなる高発光効率、長寿命が要求されているのが実情である。
従来の有機発光材料としては、例えば、単一のモノアントラセン化合物(特許文献1参照)や単一のビスアントラセン化合物(特許文献2参照)が開示されている。また、有機発光材料としてジスチリル化合物を用い、これにスチリルアミンなどを添加したものを用いることによる、有機EL素子の長寿命化も提案されている(特許文献3参照)。
他に、モノ又はビスアントラセン化合物とジスチリル化合物を有機発光媒体層として用いた技術が開示されている(特許文献4参照)。
さらに、ジアミノクリセン誘導体を用いた青色発光素子が開示されている(特許文献5参照)。また、中心にアリーレン基を有する芳香族アミン誘導体を正孔輸送材料として用いる発明(特許文献6参照)、ジベンゾフラン環、ジベンゾチオフェン環、ベンゾフラン環、ベンゾチオフェン環等がアリーレン基を介して窒素原子に結合した芳香族アミン誘導体を正孔輸送材料として用いる発明(特許文献7参照)なども開示されている。また、置換又は無置換のシリル基を有するフェニル基が窒素原子に置換した芳香族ジアミン誘導体を発光層材料として用いる発明(特許文献8参照)が開示されている。
本発明は、かかる課題を解決するためになされたもので、寿命が長く、高発光効率な有機EL素子及びそれを実現する化合物を提供することを目的とするものである。
但し、B及びCがトリメチルシリル基且つbとcが1であり、いずれもパラ置換である場合、A及びR11がメチル基ならば、aとdが同時に1で、いずれもパラ置換となる構造を除く。また、Aがトリメチルシリル基及びaが1且つパラ置換である場合、R11がメチル基及びdが2且つ2つのR11がいずれもメタ置換ならば、Bがトリメチルシリル基及びbが1且つパラ置換並びにCがメチル基及びcが2且つ2つのCがいずれもメタ置換となる構造を除く。)
炭素数1~50のアルキル基としては、例えばメチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、s-ブチル基、t-ブチル基、各種ペンチル基(「各種」とは、直鎖、分岐鎖、環状のいずれをも含むことを示す。以下同様。)が挙げられ、炭素数1~10のアルキル基が好ましい。
炭素数3~50のシクロアルキル基としては、例えばシクロプロピル基、シクロペンチル基、シクロヘキシル基、4-メチルシクロヘキシル基、シクロオクチル基が挙げられ、炭素数5~8のシクロヘキシル基が好ましい。
炭素数7~50のアラルキル基としては、例えば、ベンジル基、α,α-フェニルメチルベンジル基、α,α-ジメチルベンジル基、α-フェノキシベンジル基、α,α-メチルフェニルベンジル基、α,α-ジトリフルオロメチルベンジル基、トリフェニルメチル基、α-ベンジルオキシベンジル基、1-フェニルエチル基、2-フェニルエチル基、1-フェニルイソプロピル基、2-フェニルイソプロピル基、フェニル-t-ブチル基、α-ナフチルメチル基、1-α-ナフチルエチル基、2-α-ナフチルエチル基、1-α-ナフチルイソプロピル基、2-α-ナフチルイソプロピル基、β-ナフチルメチル基、1-β-ナフチルエチル基、2-β-ナフチルエチル基、1-β-ナフチルイソプロピル基、2-β-ナフチルイソプロピル基、1-ピロリルメチル基、2-(1-ピロリル)エチル基、p-メチルベンジル基、m-メチルベンジル基、o-メチルベンジル基、p-クロロベンジル基、m-クロロベンジル基、o-クロロベンジル基、p-ブロモベンジル基、m-ブロモベンジル基、o-ブロモベンジル基、p-ヨードベンジル基、m-ヨードベンジル基、o-ヨードベンジル基、p-ヒドロキシベンジル基、m-ヒドロキシベンジル基、o-ヒドロキシベンジル基、p-アミノベンジル基、m-アミノベンジル基、o-アミノベンジル基、p-ニトロベンジル基、m-ニトロベンジル基、o-ニトロベンジル基、p-シアノベンジル基、m-シアノベンジル基、o-シアノベンジル基、1-ヒドロキシ-2-フェニルイソプロピル基、1-クロロ-2-フェニルイソプロピル基が挙げられ、炭素数7~20のアラルキル基が好ましい。
炭素数6~50のアリール基としては、例えばフェニル基、トリル基、ナフチル基、アセナフチレニル基、アントリル基、フェナントリル基、フェナレニル基、フルオレニル基、a-インダセニル基、as-インダセニル基が挙げられ、炭素数6~14のアリール基が好ましい。
特にシリル基としては、トリアルキルシリル基、ジアルキル-モノアリールシリル基、モノアルキル-ジアリールシリル基、トリアリールシリル基がより好ましい。
置換もしくは無置換の炭素数3~50のシクロアルキル基としては、例えばシクロプロピル基、シクロペンチル基、シクロヘキシル基、4-メチルシクロヘキシル基、シクロオクチル基が挙げられ、炭素数5~8のシクロヘキシル基が好ましい。
置換もしくは無置換の炭素数7~50のアラルキル基としては、例えばベンジル基、α,α-フェニルメチルベンジル基、α,α-ジメチルベンジル基、α-フェノキシベンジル基、α,α-メチルフェニルベンジル基、α,α-ジトリフルオロメチルベンジル基、トリフェニルメチル基、α-ベンジルオキシベンジル基、1-フェニルエチル基、2-フェニルエチル基、1-フェニルイソプロピル基、2-フェニルイソプロピル基、フェニル-t-ブチル基、α-ナフチルメチル基、1-α-ナフチルエチル基、2-α-ナフチルエチル基、1-α-ナフチルイソプロピル基、2-α-ナフチルイソプロピル基、β-ナフチルメチル基、1-β-ナフチルエチル基、2-β-ナフチルエチル基、1-β-ナフチルイソプロピル基、2-β-ナフチルイソプロピル基、1-ピロリルメチル基、2-(1-ピロリル)エチル基、p-メチルベンジル基、m-メチルベンジル基、o-メチルベンジル基、p-クロロベンジル基、m-クロロベンジル基、o-クロロベンジル基、p-ブロモベンジル基、m-ブロモベンジル基、o-ブロモベンジル基、p-ヨードベンジル基、m-ヨードベンジル基、o-ヨードベンジル基、p-ヒドロキシベンジル基、m-ヒドロキシベンジル基、o-ヒドロキシベンジル基、p-アミノベンジル基、m-アミノベンジル基、o-アミノベンジル基、p-ニトロベンジル基、m-ニトロベンジル基、o-ニトロベンジル基、p-シアノベンジル基、m-シアノベンジル基、o-シアノベンジル基、1-ヒドロキシ-2-フェニルイソプロピル基、1-クロロ-2-フェニルイソプロピル基が挙げられ、炭素数7~20のアラルキル基が好ましい。
置換もしくは無置換の炭素数1~50のアルキルオキシ基としては、-OYで表される基であり、該Yとしては、上記「A、B、Cの内、シリル基ではない残りの基が表す、置換もしくは無置換の炭素数1~50のアルキル基」で示したアルキル基と同様のものが挙げられる。それらの中でも、炭素数1~10のアルキル基が好ましく、炭素数1~5のアルキル基がより好ましく、メチル基がさらに好ましい。
置換もしくは無置換の炭素数6~50のアリール基としては、例えばフェニル基、トリル基、メトキシフェニル基、エトキシフェニル基、ブトキシフェニル基、ナフチル基、アセナフチレニル基、アントリル基、フェナントリル基、フェナレニル基、フルオレニル基、a-インダセニル基、as-インダセニル基が挙げられる。
かかる置換もしくは無置換の炭素数1~50のアルキル基としては、例えばメチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、s-ブチル基、t-ブチル基、各種ペンチル基が挙げられ、炭素数1~10のアルキル基が好ましい。
置換もしくは無置換の炭素数3~50のシクロアルキル基としては、例えばシクロプロピル基、シクロペンチル基、シクロヘキシル基、4-メチルシクロヘキシル基、シクロオクチル基が挙げられ、炭素数5~8のシクロヘキシル基が好ましい。
置換もしくは無置換の炭素数7~50のアラルキル基としては、例えば、ベンジル基、α,α-フェニルメチルベンジル基、α,α-ジメチルベンジル基、α-フェノキシベンジル基、α,α-メチルフェニルベンジル基、α,α-ジトリフルオロメチルベンジル基、トリフェニルメチル基、α-ベンジルオキシベンジル基、1-フェニルエチル基、2-フェニルエチル基、1-フェニルイソプロピル基、2-フェニルイソプロピル基、フェニル-t-ブチル基、α-ナフチルメチル基、1-α-ナフチルエチル基、2-α-ナフチルエチル基、1-α-ナフチルイソプロピル基、2-α-ナフチルイソプロピル基、β-ナフチルメチル基、1-β-ナフチルエチル基、2-β-ナフチルエチル基、1-β-ナフチルイソプロピル基、2-β-ナフチルイソプロピル基、1-ピロリルメチル基、2-(1-ピロリル)エチル基、p-メチルベンジル基、m-メチルベンジル基、o-メチルベンジル基、p-クロロベンジル基、m-クロロベンジル基、o-クロロベンジル基、p-ブロモベンジル基、m-ブロモベンジル基、o-ブロモベンジル基、p-ヨードベンジル基、m-ヨードベンジル基、o-ヨードベンジル基、p-ヒドロキシベンジル基、m-ヒドロキシベンジル基、o-ヒドロキシベンジル基、p-アミノベンジル基、m-アミノベンジル基、o-アミノベンジル基、p-ニトロベンジル基、m-ニトロベンジル基、o-ニトロベンジル基、p-シアノベンジル基、m-シアノベンジル基、o-シアノベンジル基、1-ヒドロキシ-2-フェニルイソプロピル基、1-クロロ-2-フェニルイソプロピル基が挙げられ、炭素数7~20のアラルキル基が好ましい。
置換もしくは無置換の炭素数1~50のアルキルオキシ基としては、-OY'で表される基であり、該Y'としては、上記「A、B、Cの内、シリル基ではない残りの基が表す、置換もしくは無置換の炭素数1~50のアルキル基」で示したアルキル基と同様のものが挙げられる。それらの中でも、炭素数1~10のアルキル基が好ましく、炭素数1~5のアルキル基がより好ましく、メチル基がさらに好ましい。
置換もしくは無置換の炭素数6~50のアリール基としては、例えばフェニル基、トリル基、ナフチル基、アセナフチレニル基、アントリル基、フェナントリル基、フェナレニル基、フルオレニル基、a-インダセニル基、as-インダセニル基が挙げられ、炭素数6~14のアリール基が好ましい。
また、一般式(I)で表わされる芳香族ジアミン誘導体としては、A及びCのみが置換又は無置換のシリル基である芳香族ジアミン誘導体が好ましい。
また、本発明の芳香族ジアミン誘導体は、有機EL素子用ドーピング材料として、より好適である。
本発明の有機EL素子においては、発光層が、本発明の芳香族ジアミン誘導体を含有すると好ましく、含有量としては、通常0.1~20質量%が好ましく、1~10質量%がより好ましく、3~7質量%がさらに好ましい。また、本発明の芳香族ジアミン誘導体は、極めて高い蛍光量子効率、高い正孔輸送能力及び電子輸送能力を併せ持ち、均一な薄膜を形成することができるので、この芳香族ジアミン誘導体のみで発光層を形成することも可能である。
また、本発明の有機EL素子は、陰極と陽極間に少なくとも発光層を含む二層以上からなる有機薄膜層が挟持されている有機EL素子において、陽極と発光層との間に本発明の芳香族ジアミン誘導体を主成分とする有機層を有しても好ましい。該有機層としては、正孔注入層、正孔輸送層等が挙げられる。
前記R12~R19の芳香族環の置換基は、例えばハロゲン原子、ヒドロキシル基、ニトロ基、シアノ基、炭素数1~10のアルキル基、炭素数1~30のアリール基、炭素数3~20のシクロアルキル基、炭素数1~10のアルコキシル基、炭素数5~30の芳香族複素環基、炭素数7~30のアラルキル基、炭素数6~30のアリールオキシ基、炭素数6~30のアリールチオ基、炭素数2~10のアルコキシカルボニル基、カルボキシル基でさらに置換されていてもよい。
また、DとEの少なくとも一方は、置換もしくは無置換の炭素数10~30の縮合環基を有する置換基であることが好ましく、置換もしくは無置換のナフチル基を有する置換基であることがより好ましい。
なお、DとEは異なることが好ましい。
かかるD及びEの芳香族環の置換基は、例えばハロゲン原子、ヒドロキシル基、ニトロ基、シアノ基、炭素数1~10のアルキル基、炭素数1~30のアリール基、炭素数3~20のシクロアルキル基、炭素数1~10のアルコキシル基、炭素数5~30の芳香族複素環基、炭素数7~30のアラルキル基、炭素数6~30のアリールオキシ基、炭素数6~30のアリールチオ基、炭素数2~10のアルコキシカルボニル基、カルボキシル基でさらに置換されていてもよい。
L1及びL2は、それぞれ独立して、置換もしくは無置換のフェニレン基、置換もしくは無置換のナフタレニレン基、置換もしくは無置換のフルオレニレン基又は置換もしくは無置換のジベンゾシロリレン基である。
sは0~2の整数、pは1~4の整数、qは0~2の整数、rは0~4の整数である。
また、L1又はAr1は、ピレンの1~5位のいずれかに結合し、L2又はAr2は、ピレンの6~10位のいずれかに結合する。
ただし、p+rが偶数の時、Ar1、Ar2、L1、L2は下記(1)又は(2) を満たす。
(1)Ar1≠Ar2及び/又はL1≠L2(ここで≠は、異なる構造の基であることを示す。)
(2)Ar1=Ar2かつL1=L2の時
(2-1) s≠q及び/又はp≠r、又は
(2-2) s=qかつp=rの時、
(2-2-1) L1及びL2、又はピレンが、それぞれAr1及びAr2上の異なる結合位置に結合しているか、(2-2-2) L1及びL2、又はピレンが、Ar1及びAr2上の同じ結合位置で結合している場合、L1及びL2又はAr1及びAr2のピレンにおける置換位置が1位と6位、又は2位と7位である場合はない。
炭素数1~50のアルキル基としては、例えばメチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、s-ブチル基、t-ブチル基、各種ペンチル基が挙げられ、炭素数1~10のアルキル基が好ましい。
炭素数3~50のシクロアルキル基としては、例えばシクロプロピル基、シクロペンチル基、シクロヘキシル基、4-メチルシクロヘキシル基、シクロオクチル基が挙げられ、炭素数5~8のシクロヘキシル基が好ましい。
炭素数7~50のアラルキル基としては、例えば、ベンジル基、α,α-フェニルメチルベンジル基、α,α-ジメチルベンジル基、α-フェノキシベンジル基、α,α-メチルフェニルベンジル基、α,α-ジトリフルオロメチルベンジル基、トリフェニルメチル基、α-ベンジルオキシベンジル基、1-フェニルエチル基、2-フェニルエチル基、1-フェニルイソプロピル基、2-フェニルイソプロピル基、フェニル-t-ブチル基、α-ナフチルメチル基、1-α-ナフチルエチル基、2-α-ナフチルエチル基、1-α-ナフチルイソプロピル基、2-α-ナフチルイソプロピル基、β-ナフチルメチル基、1-β-ナフチルエチル基、2-β-ナフチルエチル基、1-β-ナフチルイソプロピル基、2-β-ナフチルイソプロピル基、1-ピロリルメチル基、2-(1-ピロリル)エチル基、p-メチルベンジル基、m-メチルベンジル基、o-メチルベンジル基、p-クロロベンジル基、m-クロロベンジル基、o-クロロベンジル基、p-ブロモベンジル基、m-ブロモベンジル基、o-ブロモベンジル基、p-ヨードベンジル基、m-ヨードベンジル基、o-ヨードベンジル基、p-ヒドロキシベンジル基、m-ヒドロキシベンジル基、o-ヒドロキシベンジル基、p-アミノベンジル基、m-アミノベンジル基、o-アミノベンジル基、p-ニトロベンジル基、m-ニトロベンジル基、o-ニトロベンジル基、p-シアノベンジル基、m-シアノベンジル基、o-シアノベンジル基、1-ヒドロキシ-2-フェニルイソプロピル基、1-クロロ-2-フェニルイソプロピル基が挙げられ、炭素数7~20のアラルキル基が好ましい。
炭素数1~50のアルコキシル基としては、例えばメトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、n-ブトキシ基、イソブトキシ基、s-ブトキシ基、t-ブトキシ基が挙げられ、炭素数1~10のアルコキシル基が好ましい。
炭素数6~50のアリール基としては、例えばフェニル基、ナフチル基、アセナフチレニル基、アントリル基、フェナントリル基、フェナレニル基、フルオレニル基、a-インダセニル基、as-インダセニル基が挙げられ、炭素数6~14のアリール基が好ましい。
炭素数6~50のアリールオキシ基としては、例えばフェノキシ基、ナフチルオキシ基が挙げられ、炭素数6~20のアリールオキシ基が好ましい。
炭素数6~50のアリールチオ基としては、例えば、フェニルチオ基、ナフチルチオ基が挙げられ、炭素数6~20のアリールチオ基が好ましい。
炭素数1~50のアルコキシカルボニル基としては、例えばメトキシカルボニル基、エトキシカルボニル基、各種プロポキシカルボニル基、各種ブトキシカルボニル基が挙げられ、炭素数1~20のアルコキシカルボニル基が好ましい。
アミノ基としては、例えばジメチルアミノ基、ジエチルアミノ基、ジフェニルアミノ基、ジナフチルアミノ基などの炭素数1~50のアルキル基や炭素数6~50のアリール基が置換したアミノ基が挙げられる。
ハロゲン原子としては、例えばフッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
また、正孔注入層、発光層、電子注入層は、それぞれ二層以上の層構成により形成されてもよい。その際には、正孔注入層の場合、電極から正孔を注入する層を正孔注入層、正孔注入層から正孔を受け取り発光層まで正孔を輸送する層を正孔輸送層と呼ぶ。同様に、電子注入層の場合、電極から電子を注入する層を電子注入層、電子注入層から電子を受け取り発光層まで電子を輸送する層を電子輸送層と呼ぶ。これらの各層は、材料のエネルギー準位、耐熱性、有機層又は金属電極との密着性等の各要因により選択されて使用される。
芳香族第三級アミン誘導体としては、例えば、トリフェニルアミン、トリトリルアミン、トリルジフェニルアミン、N,N’-ジフェニル-N,N’-(3-メチルフェニル)-1,1’-ビフェニル-4,4’-ジアミン、N,N,N’,N’-(4-メチルフェニル)-1,1’-フェニル-4,4’-ジアミン、N,N,N’,N’-(4-メチルフェニル)-1,1’-ビフェニル-4,4’-ジアミン、N,N’-ジフェニル-N,N’-ジナフチル-1,1’-ビフェニル-4,4’-ジアミン、N,N’-(メチルフェニル)-N,N’-(4-n-ブチルフェニル)-フェナントレン-9,10-ジアミン、N,N-ビス(4-ジ-4-トリルアミノフェニル)-4-フェニル-シクロヘキサン等、又はこれらの芳香族第三級アミン骨格を有したオリゴマーもしくはポリマーが挙げられるが、これらに限定されるものではない。
また、本発明の有機EL素子は、発光層と陽極との間に、これらの芳香族第三級アミン誘導体及び/又はフタロシアニン誘導体を含有する層、例えば、前記正孔輸送層又は正孔注入層を形成してなると好ましい。
前記金属錯体化合物としては、例えば、8-ヒドロキシキノリナートリチウム、ビス(8-ヒドロキシキノリナート)亜鉛、ビス(8-ヒドロキシキノリナート)銅、ビス(8-ヒドロキシキノリナート)マンガン、トリス(8-ヒドロキシキノリナート)アルミニウム、トリス(2-メチル-8-ヒドロキシキノリナート)アルミニウム、トリス(8-ヒドロキシキノリナート)ガリウム、ビス(10-ヒドロキシベンゾ[h]キノリナート)ベリリウム、ビス(10-ヒドロキシベンゾ[h]キノリナート)亜鉛、ビス(2-メチル-8-キノリナート)クロロガリウム、ビス(2-メチル-8-キノリナート)(o-クレゾラート)ガリウム、ビス(2-メチル-8-キノリナート)(1-ナフトラート)アルミニウム、ビス(2-メチル-8-キノリナート)(2-ナフトラート)ガリウム等が挙げられるが、これらに限定されるものではない。
前記含窒素五員誘導体としては、例えば、オキサゾール、チアゾール、オキサジアゾール、チアジアゾール、トリアゾール誘導体が好ましい。具体的には、2,5-ビス(1-フェニル)-1,3,4-オキサゾール、ジメチルPOPOP、2,5-ビス(1-フェニル)-1,3,4-チアゾール、2,5-ビス(1-フェニル)-1,3,4-オキサジアゾール、2-(4’-t-ブチルフェニル)-5-(4”-ビフェニル)-1,3,4-オキサジアゾール、2,5-ビス(1-ナフチル)-1,3,4-オキサジアゾール、1,4-ビス[2-(5-フェニルオキサジアゾリル)]ベンゼン、1,4-ビス[2-(5-フェニルオキサジアゾリル)-4-t-ブチルベンゼン]、2-(4’-t-ブチルフェニル)-5-(4”-ビフェニル)-1,3,4-チアジアゾール、2,5-ビス(1-ナフチル)-1,3,4-チアジアゾール、1,4-ビス[2-(5-フェニルチアジアゾリル)]ベンゼン、2-(4’-t-ブチルフェニル)-5-(4”-ビフェニル)-1,3,4-トリアゾール、2,5-ビス(1-ナフチル)-1,3,4-トリアゾール、1,4-ビス[2-(5-フェニルトリアゾリル)]ベンゼン等が挙げられるが、これらに限定されるものではない。
本発明の有機EL素子の陽極に使用される導電性材料としては、4eVより大きな仕事関数を持つものが適しており、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウム等及びそれらの合金、ITO基板、NESA基板に使用される酸化スズ、酸化インジウム等の酸化金属、さらにはポリチオフェンやポリピロール等の有機導電性樹脂が用いられる。陰極に使用される導電性物質としては、4eVより小さな仕事関数を持つものが適しており、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガン、アルミニウム、フッ化リチウム等及びそれらの合金が用いられるが、これらに限定されるものではない。合金としては、マグネシウム/銀、マグネシウム/インジウム、リチウム/アルミニウム等が代表例として挙げられるが、これらに限定されるものではない。合金の比率は、蒸着源の温度、雰囲気、真空度等により制御され、適切な比率に選択される。陽極及び陰極は、必要があれば二層以上の層構成により形成されていてもよい。
湿式成膜法の場合、各層を形成する材料を、エタノール、クロロホルム、テトラヒドロフラン、ジオキサン等の適切な溶媒に溶解又は分散させて薄膜を形成するが、その溶媒はいずれであっても良い。また、いずれの有機薄膜層においても、成膜性向上、膜のピンホール防止等のため適切な樹脂や添加剤を使用しても良い。使用の可能な樹脂としては、ポリスチレン、ポリカーボネート、ポリアリレート、ポリエステル、ポリアミド、ポリウレタン、ポリスルフォン、ポリメチルメタクリレート、ポリメチルアクリレート、セルロース等の絶縁性樹脂及びそれらの共重合体、ポリ-N-ビニルカルバゾール、ポリシラン等の光導電性樹脂、ポリチオフェン、ポリピロール等の導電性樹脂を挙げられる。また、添加剤としては、酸化防止剤、紫外線吸収剤、可塑剤等を挙げられる。
アルゴン気流下、冷却管付き300mL三口フラスコ中に、6,12-ジブロモクリセン3.8g(10mmol)、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミン6.4g(25mmol)、酢酸パラジウム0.03g(1.5mol%)、トリ-t-ブチルホスフィン0.06g(3mol%)、ナトリウムt-ブトキシド2.4g(25mmol)及び乾燥トルエン100mLを仕込み、100℃にて一晩加熱撹拌した。反応終了後、析出した結晶を濾取し、トルエン50mL、メタノール100mLにて洗浄し、淡黄色粉末6.0gを得た。得られた粉末は、FD-MS(フィールドディソープションマススペクトル)測定にてm/e=734が確認され、前記化合物(D-1)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-4-エチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=762が確認され、前記化合物(D-2)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-4-イソプロピルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=790が確認され、前記化合物(D-3)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-4-t-ブチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=818が確認され、前記化合物(D-4)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-2,4-ジメチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=762が確認され、前記化合物(D-5)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-3,4-ジメチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=762が確認され、前記化合物(D-6)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-3,5-ジエチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=818が確認され、前記化合物(D-7)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-3,4,5-トリメチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=790が確認され、前記化合物(D-8)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-m-トリルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=734が確認され、前記化合物(D-9)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-3-t-ブチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=818が確認され、前記化合物(D-10)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-o-トリルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=734が確認され、前記化合物(D-11)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-4-メトキシフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=766が確認され、前記化合物(D-12)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-4-シクロヘキシルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=870が確認され、前記化合物(D-13)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-4-シクロペンチルフェニルアミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=842が確認され、前記化合物(D-14)と同定した。
合成例1において、N-[4-(トリメチルシリル)フェニル)]-N-p-トリルアミンの代わりに、N-[4-(トリメチルシリル)フェニル)]-N-5-(2,3-ジヒドロ-1H-インデニル)アミンを用いた以外は、合成例1と同様の方法で合成した。得られた粉末は、FD-MS測定にてm/e=786が確認され、前記化合物(D-15)と同定した。
25×75×1.1mmサイズのガラス基板上に、膜厚120nmのインジウムスズ酸化物からなる透明電極を設けた。このガラス基板に紫外線及びオゾンを照射して洗浄したのち、真空蒸着装置にこの基板を設置した。
まず、正孔注入層として、N’,N”-ビス[4-(ジフェニルアミノ)フェニル]-N’,N”-ジフェニルビフェニル-4,4’-ジアミンを60nmの厚さに蒸着したのち、その上に正孔輸送層として、N,N,N’,N’-テトラキス(4-ビフェニル)-4,4’-ベンジジンを20nmの厚さに蒸着した。次いで、10-(4-(ナフタレン-1-イル)フェニル)-9-(ナフタレン-2-イル)アントラセンと上記化合物(D-1)とを、質量比40:2で同時蒸着し、厚さ40nmの発光層を形成した。
次に、電子注入層として、トリス(8-ヒドロキシキノリナト)アルミニウムを20nmの厚さに蒸着した。次に弗化リチウムを1nmの厚さに蒸着し、次いでアルミニウムを150nmの厚さに蒸着した。このアルミニウム/弗化リチウムは陰極として働く。このようにして有機EL素子を作製した。
次にこの素子に通電試験を行なったところ、電圧6.5V、電流密度10mA/m2にて、発光効率3.0cd/A、490cd/m2の純青色発光(発光極大波長:457nm)が得られた。初期輝度500cd/m2で直流の連続通電試験を行なったところ、半減寿命は2500時間であった。
実施例1において、ドーピング材料として化合物(D-1)の代わりに、化合物(D-2)を用いたこと以外は、実施例1と同様にして有機EL素子を作製した。
得られた有機EL素子に通電試験を行なったところ、電圧6.5V及び電流密度10mA/m2にて、500cd/m2の純青色発光(発光波長:457nm)が得られた。また、実施例1と同様にして連続通電試験を行なったところ、半減寿命は2200時間であった。
実施例1において、ドーピング材料として化合物(D-1)の代わりに、化合物(D-3)を用いたこと以外は、実施例1と同様にして有機EL素子を作製した。
得られた有機EL素子に通電試験を行なったところ、電圧6.5V及び電流密度10mA/m2にて、500cd/m2の純青色発光(発光波長:457nm)が得られた。また、実施例1と同様にして連続通電試験を行なったところ、半減寿命は2300時間であった。
実施例1において、ドーピング材料として、化合物(D-1)の代わりに、6,12-N,N’-[テトラキス(4-トリメチルシリルフェニル)]ジアミノクリセンを用いたこと以外は、実施例1と同様にして有機EL素子を作製した。
得られた有機EL素子に通電試験を行なったところ、電圧6.5V及び電流密度10mA/m2にて300cd/m2の純青色発光(発光波長:452nm)が得られた。また、実施例1と同様にして連続通電試験を行なったところ、半減寿命は1500時間であった。
Claims (13)
- 下記一般式(I)で表わされる芳香族ジアミン誘導体。
また、A、B、Cは、少なくとも1つが置換又は無置換のシリル基を表し、残りは水素原子、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炭素数3~50のシクロアルキル基、置換もしくは無置換の炭素数7~50のアラルキル基、置換もしくは無置換の炭素数1~50のアルキルオキシ基又は置換もしくは無置換の炭素数6~50のアリール基を表し、a、b、c、dはそれぞれ独立して1~5の整数を表す。なお、a、b、c、dが2~5の整数の場合、各A、B、C、R11は、それぞれ同一ベンゼン環上で同じ基でも異なる基となっていてもよい。
但し、B及びCがトリメチルシリル基且つbとcが1であり、いずれもパラ置換である場合、A及びR11がメチル基ならば、aとdが同時に1で、いずれもパラ置換となる構造を除く。また、Aがトリメチルシリル基及びaが1且つパラ置換である場合、R11がメチル基及びdが2且つ2つのR11がいずれもメタ置換ならば、Bがトリメチルシリル基及びbが1且つパラ置換並びにCがメチル基及びcが2且つ2つのCがいずれもメタ置換となる構造を除く。) - 前記式中、aが1のとき、Aが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炭素数3~50のシクロアルキル基、置換もしくは無置換の炭素数7~50のアラルキル基、置換もしくは無置換の炭素数1~50のアルキルオキシ基、又は置換もしくは無置換の炭素数6~50のアリール基であり、aが2~5のとき、複数のAの内、少なくとも一つが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炭素数3~50のシクロアルキル基、置換もしくは無置換の炭素数7~50のアラルキル基、置換もしくは無置換の炭素数1~50のアルキルオキシ基又は置換もしくは無置換の炭素数6~50のアリール基である、請求項1に記載の芳香族ジアミン誘導体。
- 前記式中、シリル基がトリアルキルシリル基、ジアルキル-モノアリールシリル基、モノアルキル-ジアリールシリル基又はトリアリールシリル基である、請求項1に記載の芳香族ジアミン誘導体。
- 前記式中、シリル基がトリメチルシリル基である、請求項1に記載の芳香族ジアミン誘導体。
- 有機エレクトロルミネッセンス素子用発光材料である請求項1に記載の芳香族ジアミン誘導体。
- 有機エレクトロルミネッセンス素子用青色系発光材料である請求項1に記載の芳香族ジアミン誘導体。
- 有機エレクトロルミネッセンス素子用ドーピング材料である請求項1に記載の芳香族ジアミン誘導体。
- 陰極と陽極の間に少なくとも発光層を含む一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミレッセンス素子において、該有機薄膜層の少なくとも一層が、請求項1に記載の芳香族ジアミン誘導体を単独もしくは混合物の一成分として含有する有機エレクトロルミネッセンス素子。
- 陰極と陽極の間に少なくとも発光層を含む一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミレッセンス素子において、発光層と陽極との間の一層が、請求項1に記載の芳香族ジアミン誘導体を単独もしくは混合物の一成分として含有する有機エレクトロルミネッセンス素子。
- 陰極と陽極の間に少なくとも発光層を含む一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミレッセンス素子において、該発光層が、請求項1に記載の芳香族ジアミン誘導体を単独もしくは混合物の一成分として含有する有機エレクトロルミネッセンス素子。
- 前記発光層が、請求項1に記載の芳香族ジアミン誘導体をドーピング材料として含有し、下記一般式(i)で表されるアントラセン誘導体をホスト材料として含有する請求項11に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、請求項1~5のいずれかに記載の芳香族ジアミン誘導体をドーピング材料として含有し、下記一般式(ii)で表されるピレン誘導体をホスト材料として含有する請求項11に記載の有機エレクトロルミネッセンス素子。
L1及びL2は、それぞれ独立して、置換もしくは無置換のフェニレン基、置換もしくは無置換のナフタレニレン基、置換もしくは無置換のフルオレニレン基又は置換もしくは無置換のジベンゾシロリレン基である。
sは0~2の整数、pは1~4の整数、qは0~2の整数、rは0~4の整数である。
また、L1又はAr1は、ピレンの1~5位のいずれかに結合し、L2又はAr2は、ピレンの6~10位のいずれかに結合する。
ただし、p+rが偶数の時、Ar1、Ar2、L1、L2は下記(1)又は(2) を満たす。
(1)Ar1≠Ar2及び/又はL1≠L2(ここで≠は、異なる構造の基であることを示す。)
(2)Ar1=Ar2かつL1=L2の時
(2-1) s≠q及び/又はp≠r、又は
(2-2) s=qかつp=rの時、
(2-2-1) L1及びL2、又はピレンが、それぞれAr1及びAr2上の異なる結合位置に結合しているか、(2-2-2) L1及びL2、又はピレンが、Ar1及びAr2上の同じ結合位置で結合している場合、L1及びL2又はAr1及びAr2のピレンにおける置換位置が1位と6位、又は2位と7位である場合はない。)
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