JP3797310B2 - Material for organic electroluminescence device and organic electroluminescence device using the same - Google Patents
Material for organic electroluminescence device and organic electroluminescence device using the same Download PDFInfo
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- JP3797310B2 JP3797310B2 JP2002305258A JP2002305258A JP3797310B2 JP 3797310 B2 JP3797310 B2 JP 3797310B2 JP 2002305258 A JP2002305258 A JP 2002305258A JP 2002305258 A JP2002305258 A JP 2002305258A JP 3797310 B2 JP3797310 B2 JP 3797310B2
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- 238000005401 electroluminescence Methods 0.000 title claims description 94
- 239000000463 material Substances 0.000 title claims description 86
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000002356 single layer Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
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- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical class C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 description 2
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- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- YERRTOUSFSZICJ-UHFFFAOYSA-N methyl 2-amino-2-(4-bromophenyl)acetate Chemical compound COC(=O)C(N)C1=CC=C(Br)C=C1 YERRTOUSFSZICJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YQVDNJJYNQAOER-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-4-methylaniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C=2C=CC(N)=CC=2)C=C1 YQVDNJJYNQAOER-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy 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])C([H])([H])O* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- NVCMFMPORSTMCN-UHFFFAOYSA-N perylene-1,2-diamine Chemical group C1=CC(C2=C(C(N)=CC=3C2=C2C=CC=3)N)=C3C2=CC=CC3=C1 NVCMFMPORSTMCN-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
- ARFWEVQMYYLLPJ-UHFFFAOYSA-N phenanthrene-1,2-diamine Chemical compound C1=CC=C2C3=CC=C(N)C(N)=C3C=CC2=C1 ARFWEVQMYYLLPJ-UHFFFAOYSA-N 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
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-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
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 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
- 150000003852 triazoles Chemical class 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
Landscapes
- Electroluminescent Light Sources (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【0001】
【発明の属する技術分野】
本発明は平面光源や表示に使用される有機エレクトロルミネッセンス(EL)素子用材料およびそれを用いた有機EL素子に関する。さらに詳しくは、長寿命を有し、黄色〜赤色の高輝度発光を得ることのできる有機EL素子用材料およびそれを用いた有機EL素子に関する。
【0002】
【従来の技術】
有機物質を使用したEL素子は、固体発光型の安価な大面積フルカラー表示素子としての用途が有望視され、多くの開発が行われている。一般にEL素子は、発光層および該層をはさんだ一対の対向電極から構成されている。発光は、両電極間に電界が印加されると、陰極側から電子が注入され、陽極側から正孔が注入され、この電子が発光層において正孔と再結合し、エネルギー準位が伝導帯から価電子帯に戻る際にエネルギーを光として放出する現象である。
【0003】
従来の有機EL素子は、無機EL素子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。近年、10V以下の低電圧で発光する高い蛍光量子効率を持った有機化合物を含有した薄膜を積層した有機EL素子が報告され、関心を集めている(Appl.Phys.Lett.,第51巻,913頁,1987年発行参照)。この方法は、金属キレート錯体を発光層、アミン系化合物を正孔注入層に使用して、高輝度の緑色発光を得ており、6〜10Vの直流電圧で輝度は数1000(cd/m2)、最大発光効率は1.5(lm/W)を達成して、実用領域に近い性能を持っている。
【0004】
有機EL素子の中でも、特に黄色から赤色の発光を得るための有機EL素子用発光材料については、C.H.Chenら著,Macromol.Symp.,第125号,34〜36頁および49〜58頁,1997年発行に記載されているDCM、DCJ、DCJT、DCJTBといった4H−ピラン誘導体が黄色から赤色の発光を得るための有機EL素子用発光材料として報告されているが、発光輝度が低いというという問題があった。
【0005】
一方、ペリレン構造を有する有機EL素子用発光材料については、例えば、特開平11−144869号公報、特開2001−11031号公報、特開2001−176664号公報に記載されているモノおよびジアミノペリレン化合物等が知られている。
【0006】
【発明が解決しようとする課題】
従来の技術に述べた黄色〜赤色の高輝度発光を得るための有機EL素子用発光材料は、いずれも充分な発光輝度を有しておらず、寿命が短いという欠点があった。一方、ペリレンは平面性の高い分子構造であるため、有機EL素子用発光材料として用いる場合、濃度消光等の好ましくない現象が発生し易い。そのため、従来の技術に述べたように、ペリレンに結合するアミノ基の数を増やしたり、立体的に嵩高い置換基を導入する等の改良が試みられているが、それに伴う分子量の増大によって、溶剤に対する溶解性の低下や、素子作成時の蒸着性が悪くなるといった作業性の悪化という懸念がある。そのため、より一層の高い発光輝度と長い寿命を持った有機EL素子用材料が求められていた。
【0007】
【課題を解決するための手段】
本発明者らは、以上の諸問題を考慮し解決すべく鋭意研究を重ねた結果、本発明に至った。
すなわち、本発明は、下記一般式[1]で表される化合物であることを特徴とする有機エレクトロルミネッセンス素子用材料に関する。
一般式[1]
【化3】
[式中、Ar1は、置換もしくは未置換の3−ペリレニル基、R1およびR2は、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、および、置換もしくは未置換の1価の芳香族複素環基より選ばれる1価の有機残基であって、R1およびR2の少なくとも一つは、下記一般式[2]で表される1価の有機残基である。]
一般式[2]
【化4】
[式中、Ar2は、置換もしくは未置換の2価の芳香族炭化水素基、または置換もしくは未置換の2価の芳香族複素環基、Ar3は、置換もしくは未置換の1価の芳香族炭化水素基、または置換もしくは未置換の1価の芳香族複素環基、X1は、直接結合、O、S、=C(R3)R4、=Si(R5)R6のいずれかである(ここに、R3〜R6は、水素原子、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基のいずれかである)。]
[ただし、一般式[1]および一般式[1]と一般式[2]でいう置換とは、1価の脂肪族炭化水素基、1価の芳香族炭化水素基、1価の脂肪族複素環基、1価の芳香族複素環基、ハロゲン原子、シアノ基、アルコキシル基、アリールオキシ基、アルキルチオ基、アリールチオ基、アシル基、アルコキシカルボニル基、アリールオキシカルボニル基、アルキルスルホニル基、アリールスルホニル基のいずれかで置換されることである。]
また、本発明は、Ar1が、未置換の3−ペリレニル基であることを特徴とする上記有機エレクトロルミネッセンス素子用材料に関する。
また、本発明は、R1およびR2が、いずれも一般式[2]で表される1価の有機残基であることを特徴とする上記有機エレクトロルミネッセンス素子用材料に関する。
また、本発明は、X1が、直接結合であることを特徴とする上記有機エレクトロルミネッセンス素子用材料に関する。
また、本発明は、陽極と陰極とからなる一対の電極間に一層または多層の有機層を形成してなる有機エレクトロルミネッセンス素子において、少なくとも一層が上記有機エレクトロルミネッセンス素子用材料を含有する層である有機エレクトロルミネッセンス素子に関する。
また、本発明は、陽極と陰極とからなる一対の電極間に少なくとも一層の発光層を形成してなる有機エレクトロルミネッセンス素子において、発光層が上記有機エレクトロルミネッセンス素子用材料を含有する層である有機エレクトロルミネッセンス素子に関する。
また、本発明は、さらに、発光層と陰極との間に少なくとも一層の電子注入層を形成してなる上記有機エレクトロルミネッセンス素子に関する。
【0008】
【発明の実施の形態】
以下、詳細にわたって本発明を説明する。まずはじめに、本発明の有機EL素子用材料である一般式[1]で表されるモノアミン化合物について説明する。
【0009】
まず、一般式[1]中のAr1は、置換もしくは未置換の3−ペリレニル基を表す。これらペリレニル基は、さらに他の置換基によって置換されていても良い。そのような置換基としては、1価の脂肪族炭化水素基、1価の芳香族炭化水素基、1価の脂肪族複素環基、1価の芳香族複素環基、ハロゲン原子、シアノ基、アルコキシル基、アリールオキシ基、アルキルチオ基、アリールチオ基、アシル基、アルコキシカルボニル基、アリールオキシカルボニル基、アルキルスルホニル基、アリールスルホニル基のいずれかがあげられる。
【0010】
ここで、1価の脂肪族炭化水素基としては、炭素数1〜18の1価の脂肪族炭化水素基を指し、そのようなものとしては、アルキル基、アルケニル基、アルキニル基、シクロアルキル基があげられる。
【0011】
したがって、アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ヘキシル基、ヘプチル基、オクチル基、デシル基、ドデシル基、ペンタデシル基、オクタデシル基といった炭素数1〜18のアルキル基があげられる。
【0012】
また、アルケニル基としては、ビニル基、1−プロペニル基、2−プロペニル基、イソプロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−オクテニル基、1−デセニル基、1−オクタデセニル基といった炭素数2〜18のアルケニル基があげられる。
【0013】
また、アルキニル基としては、エチニル基、1−プロピニル基、2−プロピニル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−オクチニル基、1−デシニル基、1−オクタデシニル基といった炭素数2〜18のアルキニル基があげられる。
【0014】
また、シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロオクタデシル基、2−ボルニル基、2−イソボルニル基、1−アダマンチル基といった炭素数3〜18のシクロアルキル基があげられる。
【0015】
さらに、1価の芳香族炭化水素基としては、炭素数6〜30の1価の単環、縮合環、環集合芳香族炭化水素基があげられる。ここで、炭素数6〜30の1価の単環芳香族炭化水素基としては、フェニル基、o−トリル基、m−トリル基、p−トリル基、2,4−キシリル基、p−クメニル基、メシチル基等の炭素数6〜30の1価の単環芳香族炭化水素基があげられる。
【0016】
また、1価の縮合環芳香族炭化水素基としては、1−ナフチル基、2−ナフチル基、1−アンスリル基、2−アンスリル基、5−アンスリル基、1−フェナンスリル基、9−フェナンスリル基、1−アセナフチル基、2−アズレニル基、1−ピレニル基、2−トリフェニレル基、1−ピレニル基、2−ピレニル基、1−ペリレニル基、2−ペリレニル基、3−ペリレニル基、2−トレフェニレニル基、2−インデニル基、1−アセナフチレニル基、2−ナフタセニル基、2−ペンタセニル基等の炭素数10〜30の1価の縮合環炭化水素基があげられる。
【0017】
また、1価の環集合芳香族炭化水素基としては、o−ビフェニリル基、m−ビフェニリル基、p−ビフェニリル基、テルフェニリル基、7−(2−ナフチル)−2−ナフチル基等の炭素数12〜30の1価の環集合炭化水素基があげられる。
【0018】
また、1価の脂肪族複素環基としては、3−イソクロマニル基、7−クロマニル基、3−クマリニル等の炭素数3〜18の1価の脂肪族複素環基があげられる。
【0019】
また、1価の芳香族複素環基としては、2−フリル基、3−フリル基、2−チエニル基、3−チエニル基、2−ベンゾフリル基、2−ベンゾチエニル基、2−ピリジル基、3−ピリジル基、4−ピリジル基、2−キノリル基、3−キノリル基、4−キノリル基、5−キノリル基、6−キノリル基、7−キノリル基、8−キノリル基、1−イソキノリル基、3−イソキノリル基、4−イソキノリル基、5−イソキノリル基、6−イソキノリル基、7−イソキノリル基、8−イソキノリル基、2−ピリミジニル基、2−ピラジニル基、2−キナゾリニル基、2−キノキサリニル基、2−オキサゾリル基、2−チアゾリル基等の炭素数3〜30の1価の芳香族複素環基があげられる。
【0020】
また、ハロゲン原子としては、フッ素原子、塩素原子、臭素原子があげられる。
【0021】
また、アルコキシル基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基、tert−ブトキシ基、オクチルオキシ基、tert−オクチルオキシ基、2−ボルニルオキシ基、2−イソボルニルオキシ基、1−アダマンチルオキシ基等の炭素数1〜18のアルコキシル基があげられる。
【0022】
また、アリールオキシ基としては、フェノキシ基、4−tert−ブチルフェノキシ基、1−ナフチルオキシ基、2−ナフチルオキシ基、9−アンスリルオキシ基といった炭素数6〜30のアリールオキシ基があげられる。
【0023】
また、アルキルチオ基としては、メチルチオ基、エチルチオ基、tert−ブチルチオ基、ヘキシルチオ基、オクチルチオ基といった炭素数1〜18のアルキルチオ基があげられる。
【0024】
また、アリールチオ基としては、フェニルチオ基、2−メチルフェニルチオ基、4−tert−ブチルフェニルチオ基といった炭素数6〜30のアリールチオ基があげられる。
【0025】
また、アシル基としては、アセチル基、プロピオニル基、ピバロイル基、シクロヘキシルカルボニル基、ベンゾイル基、トルオイル基、アニソイル基、シンナモイル基等の炭素数2〜18のアシル基があげられる。
【0026】
また、アルコキシカルボニル基としては、メトキシカルボニル基、エトキシカルボニル基、ベンジルオキシカルボニル基等の炭素数2〜18のアルコキシカルボニル基があげられる。
【0027】
また、アリールオキシカルボニル基としては、フェノキシカルボニル基、ナフチルオキシカルボニル基等の炭素数2〜18のアリールオキシカルボニル基があげられる。
【0028】
また、アルキルスルホニル基としては、メシル基、エチルスルホニル基、プロピルスルホニル基等の炭素数2〜18のアルキルスルホニル基があげられる。
【0029】
また、アリールスルホニル基としては、ベンゼンスルホニル基、p−トルエンスルホニル基等の炭素数2〜18のアリールスルホニル基があげられる。
【0030】
上に述べた置換基は、さらに他の置換基によって置換されていても良い。
【0031】
以上述べた一般式[1]中のAr 1としては、未置換の3−ペリレニル基が特に好ましい。この理由として、ペリレンの3位にアミノ基が結合するような構造である場合、ペリレン環とアミノ基とのなす角が比較的同一平面に保たれるため蛍光性が強くなり、有機エレクトロルミネッセンス素子として用いた場合の発光輝度が向上するためと考えられるためである。
【0032】
また、置換3−ペリレニル基の中で好ましい置換基としては、アルキル基、1価の芳香族炭化水素基、1価の芳香族複素環基、アリールオキシ基、アリールチオ基があげられ、特に好ましい置換基としては、アルキル基、1価の単環芳香族炭化水素基、1価の縮合環芳香族炭化水素基、1価の環集合芳香族炭化水素基、1価の芳香族複素環基があげられる。
【0033】
また、上に述べた好ましい置換基の内、置換基の炭素数としては1〜18が好ましく、1〜12がさらに好ましい。この理由として、これら置換基の炭素数が多くなると、溶剤に対する溶解性が乏しくなるため、精製が困難になるだけでなく、素子作成時の作業性が悪くなる、また蒸着によって素子を作成しようとした場合の蒸着性が悪くなるといった懸念が考えられるためである。
【0034】
次に、一般式[1]中のR1およびR2について説明する。R1およびR2は、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基より選ばれる1価の有機残基であって、R1およびR2の少なくとも一つは、一般式[2]で表される1価の有機残基である。ここでいう置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基とは、Ar1の置換基で説明した置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基と同義である。
【0035】
ここで、一般式[2]について説明する。まず、一般式[2]中のAr2は、置換もしくは未置換の2価の芳香族炭化水素基または置換もしくは未置換の2価の芳香族複素環基を表す。ここでいう置換基とは、Ar1で説明した置換基と同義であり、また、2つ以上の置換基同士が互いに結合して環を形成していても構わない。
【0036】
ここで2価の芳香族炭化水素基とは、2価の単環もしくは縮合環、環集合芳香族炭化水素基を意味し、例えば、フェニレン基、ナフチレン基、アンスリレン基、ビフェニレン基、p−テルフェニル−4,4’’−ジイル基、m−テルフェニル−3,3’’−ジイル基、m−テルフェニル−4,4’−ジイル基、[1,2’−ビナフタレン]−4,5’−ジイル等の炭素数6〜30の2価の芳香族炭化水素基があげられる。
【0037】
また2価の芳香族複素環基とは、2価の単環もしくは縮合環、環集合芳香族複素環基を意味し、例えば、2,5−フリレン基、2,5−チエニレン基、2,5−ピリジレン基、2,4−ピリジレン基、2,3−ピリジレン基、2,5−ピラジニレン基、2,4−キノリレン基、2,6−キノリレン基、1,4−イソキノリレン基、2,3−キノキサリニレン基等の炭素数4〜30の2価の芳香族複素環基があげられる。
【0038】
以上述べたAr2における2価の芳香族炭化水素基または芳香族複素環基の内、好ましいものとしては、フェニレン基、ナフチレン基、ビフェニレン基等の炭素数6〜12の2価の芳香族炭化水素基があげられる。
【0039】
さらに、一般式[2]中のAr3は、置換もしくは未置換の1価の芳香族炭化水素基または置換もしくは未置換の1価の芳香族複素環基を表す。ここでいう置換基とは、Ar1で説明した置換基と同義であり、また、2つ以上の置換基同士が互いに結合して環を形成していても構わない。また、ここでいう置換もしく未置換の1価の芳香族炭化水素基、および置換もしくは未置換の1価の芳香族複素環基とはそれぞれ、Ar1で説明した置換もしくは未置換の1価の芳香族炭化水素基、および置換もしくは未置換の1価の芳香族複素環基と同義である。
【0040】
さらに、一般式[2]中のX1は、直接結合、O、S、=C(R3)R4、=Si(R5)R6のいずれかである(ここに、R3〜R6は、水素原子、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基のいずれかである)。ここで、R3〜R6における置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基とは、Ar1で説明した置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基と同義であり、2つ以上の置換基同士が互いに結合して環を形成していても構わない。
【0041】
一般式[1]中のR1およびR2としては、少なくとも一つが一般式[2]で表される1価の有機残基であれば良いが、いずれも一般式[2]で表される1価の有機残基であることが好ましい。この理由として、R1およびR2が、いずれも一般式[2]で表される1価の有機残基の場合、ペリレン環とアミノ基とのなす角が比較的同一平面に保たれつつも分子が立体的となるため、濃度消光等の好ましくない現象が抑えられるため、有機エレクトロルミネッセンス素子として用いた場合の発光輝度が向上するためと考えられるためである。さらに、一般式[2]中のX1が直接結合である場合、分子中の共役系が大きくなるため、発光輝度が向上すると考えられ特に好ましい。
【0042】
以上、本発明の一般式[1]で表されるモノアミン化合物について説明したが、本発明のモノアミン化合物の分子量としては、2000以下が好ましく、1500以下がさらに好ましく、1000以下が特に好ましい。この理由として、分子量が大きいと、溶剤に対する溶解性が乏しくなるため、精製が困難になるだけでなく、素子作成時の作業性が悪くなる、また蒸着によって素子を作成しようとした場合の蒸着性が悪くなるといった懸念が考えられるためである。
【0043】
本発明の有機EL素子用材料を単独で発光層に使用して作成した素子は、通常、黄色〜オレンジ色の高輝度発光を示すが、後述するように適当なドーピング材料と共に使用することで、高輝度を維持しつつ発光色を赤まで長波長化させることが可能となる。
【0044】
以下、表1に本発明の有機EL素子用材料として用いることができる化合物の代表例を示すが、本発明は、なんらこれらに限定されるものではない(ただし、表1中、t−Buは第3ブチル基を、Phはフェニル基を表す)。
【0045】
【表1】
【0046】
【0047】
【0048】
【0049】
【0050】
【0051】
【0052】
【0053】
【0054】
【0055】
【0056】
【0057】
【0058】
【0059】
【0060】
【0061】
【0062】
【0063】
【0064】
【0065】
【0066】
【0067】
【0072】
ところで、有機EL素子は、陽極と陰極間に一層または多層の有機層を形成した素子であるが、ここで、一層型有機EL素子は、陽極と陰極との間に発光材料からなる発光層を有する。一方、多層型有機EL素子は、(陽極/正孔注入層/発光層/陰極)、(陽極/発光層/電子注入層/陰極)、(陽極/正孔注入層/発光層/電子注入層/陰極)等の多層構成で積層した有機EL素子である。本発明の有機EL素子用材料は、前記いずれの層にも使用できるが、これら一層型ないし多層型有機EL素子の発光材料として好適に使用することができる。特に、本有機EL素子用発光材料を用いて一層型有機EL素子を作成する場合、陽極から注入した正孔または陰極から注入した電子を発光材料まで効率よく輸送させるための正孔注入材料または電子注入材料を含有させることができる。
【0073】
ここで、正孔注入材料とは、発光層または発光材料に対して優れた正孔注入効果を示し、発光層で生成した励起子の電子注入層または電子注入材料への移動を防止し、かつ薄膜形成性に優れた化合物を意味する。そのような正孔注入材料の例としては、フタロシアニン系化合物、ナフタロシアニン系化合物、ポルフィリン系化合物、オキサジアゾール、トリアゾール、イミダゾール、イミダゾロン、イミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒドロイミダゾール、オキサゾール、オキサジアゾール、ヒドラゾン、アシルヒドラゾン、ポリアリールアルカン、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミン等と、それらの誘導体、およびポリビニルカルバゾール、ポリシラン、導電性ポリマー等があげられるが、本発明はこれらに限定されるものではない。
【0074】
上記正孔注入材料の中でも特に効果的な正孔注入材料としては、芳香族三級アミン誘導体またはフタロシアニン誘導体があげられる。芳香族三級アミン誘導体としては、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、またはこれらの芳香族三級アミン骨格を有するオリゴマーまたはポリマーがあげられる。また、フタロシアニン(Pc)誘導体としては、H2Pc、CuPc、CoPc 、NiPc、ZnPc、PdPc、FePc、MnPc、ClAlPc、ClGaPc、ClInPc、ClSnPc、Cl2SiPc、(HO)AlPc、(HO)GaPc、VOPc、TiOPc、MoOPc、GaPc−O−GaPc等のフタロシアニン誘導体およびナフタロシアニン誘導体があげられる。以上述べた正孔注入材料は、更に電子受容材料を添加して増感させることもできる。
【0075】
一方、電子注入材料とは、発光層または発光材料に対して優れた電子注入効果を示し、発光層で生成した励起子の正孔注入層または正孔注入材料への移動を防止し、かつ薄膜形成性に優れた化合物を意味する。そのような電子注入材料の例としては、キノリン金属錯体、オキサジアゾール、ベンゾチアゾール金属錯体、ベンゾオキサゾール金属錯体、ベンゾイミダゾール金属錯体、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサジアゾール、チアジアゾール、テトラゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、アントロン等とそれらの誘導体があげられる。また、セシウム等の金属をバソフェナントロリンにドープした無機/有機複合材料(例えば、高分子学会予稿集,第50巻,4号,660頁,2001年発行)も電子注入材料の例としてあげられるが、本発明はこれらに限定されるものではない。
【0076】
上記電子注入材料の中でも特に効果的な電子注入材料としては、金属錯体化合物または含窒素五員環誘導体があげられる。ここで、金属錯体化合物の中でも、下記一般式[3]で示される化合物は好適に使用することができる。
一般式[3]
【化5】
[式中、Q1およびQ2は、それぞれ独立に、置換もしくは未置換のヒドロキシキノリン誘導体または置換もしくは未置換のヒドロキシベンゾキノリン誘導体を表し、Lは、ハロゲン原子、置換もしくは未置換のアルキル基、置換もしくは未置換のシクロアルキル基、置換もしくは未置換のアリール基、または、置換もしくは未置換の芳香族複素環基、−OR(Rは水素原子、置換もしくは未置換のアルキル基、置換もしくは未置換のシクロアルキル基、置換もしくは未置換のアリール基、または、置換もしくは未置換の芳香族複素環基を表す。)、−O−Ga−Q3(Q4)(Q3およびQ4は、Q1 およびQ2と同じ意味を表す。)で表される配位子を表す。]
【0077】
ここで一般式[3]について説明する。一般式[3]で示される化合物のQ1〜Q4は、置換もしくは未置換のヒドロキシキノリン誘導体または置換もしくは未置換のヒドロキシベンゾキノリン誘導体である。ここでいう置換基とは、一般式[1]中のR1およびR2における置換基と同義である。
【0078】
また、Lは、ハロゲン原子、置換もしくは未置換のアルキル基、置換もしくは未置換のシクロアルキル基、置換もしくは未置換のアリール基、置換もしくは未置換の芳香族複素環基を表す。ここでいう置換基とは、一般式[1]中のR1およびR2における置換基と同義である。また、置換もしくは未置換の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、シクロヘプチル基、シクロオクチル基、シクロノニル基、シクロデカニル基等をあげることができる。
【0079】
したがって、一般式[3]で示される化合物の具体例としては、ビス(2−メチル−8−ヒドロキシキノリナート)(1−ナフトラート)ガリウム錯体、ビス(2−メチル−8−ヒドロキシキノリナート)(2−ナフトラート)ガリウム錯体、ビス(2−メチル−8−ヒドロキシキノリナート)(フェノラート)ガリウム錯体、ビス(2−メチル−8−ヒドロキシキノリナート)(4−シアノ−1−ナフトラート)ガリウム錯体、ビス(2、4−ジメチル−8−ヒドロキシキノリナート)(1−ナフトラート)ガリウム錯体、ビス(2、5−ジメチル−8−ヒドロキシキノリナート)(2−ナフトラート)ガリウム錯体、ビス(2−メチル−5−フェニル−8−ヒドロキシキノリナート)(フェノラート)ガリウム錯体、ビス(2−メチル−5−シアノ−8−ヒドロキシキノリナート)(4−シアノ−1−ナフトラート)ガリウム錯体、ビス(2−メチル−8−ヒドロキシキノリナート)クロロガリウム錯体、ビス(2−メチル−8−ヒドロキシキノリナート)(o−クレゾラート)ガリウム錯体等があげられるが、本発明はこれらに限定されるものではない。尚、これら一般式[3]で示される化合物は、特開平10−88,121号公報記載の方法により合成することが可能である。
【0080】
その他、本発明に使用可能な電子注入材料の内、好ましい金属錯体化合物としては、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)亜鉛等があげられる。
【0081】
また、本発明に使用可能な電子注入材料の内、好ましい含窒素五員誘導体としては、オキサゾール、チアゾール、オキサジアゾール、チアジアゾールまたはトリアゾール誘導体があげられ、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’−tert−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−tert−ブチルベンゼン]、2−(4’−tert− 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’−tert−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)]ベンゼン等があげられる。以上述べた電子注入材料は、更に電子供与性材料を添加して増感させることもできる。
【0082】
また、本発明の有機EL素子用材料は、発光層中にドーピングして使用することも可能である。この場合、本有機EL素子用材料は、以下に説明するホスト材料に対して0.001〜50重量%の範囲で含有されることが好ましく、更には0.01〜10重量%の範囲で含有されることがより好ましい。
【0083】
本発明の有機EL素子用材料をドーピング材料として用いた時に共に使用できるホスト材料としては、キノリン金属錯体、ベンゾキノリン金属錯体、ベンゾオキサゾール金属錯体、ベンゾチアゾール金属錯体、ベンゾイミダゾール金属錯体、ベンゾトリアゾール金属錯体、イミダゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体等の電子輸送性材料。または、スチルベン誘導体、ブタジエン誘導体、ベンジジン型トリフェニルアミン誘導体、スチリルアミン型トリフェニルアミン誘導体、ジアミノアントラセン型トリフェニルアミン誘導体、ジアミノフェナントレン型トリフェニルアミン誘導体等の正孔輸送性材料、およびポリビニルカルバゾール、ポリシラン等の導電性高分子の高分子材料等があげられる。
【0084】
また、本有機EL素子における発光層中には、本発明の有機EL素子用材料の他に、他の発光材料やドーピング材料を二種類以上組み合わせて使用することもできる。この場合は本発明の有機EL素子用材料はホスト材料として機能する場合もある。本発明の有機EL素子用材料と共に使用できる他の発光材料やドーピング材料としては、アントラセン、ナフタレン、フェナントレン、ピレン、テトラセン、コロネン、クリセン、フルオレセイン、ペリレン、フタロペリレン、ナフタロペリレン、ペリノン、フタロペリノン、ナフタロペリノン、ジフェニルブタジエン、テトラフェニルブタジエン、クマリン、オキサジアゾール、アルダジン、ビスベンゾキサゾリン、ビススチリル、ピラジン、シクロペンタジエン、キノリン金属錯体、アミノキノリン金属錯体、イミン、ジフェニルエチレン、ビニルアントラセン、ジアミノカルバゾール、ピラン、チオピラン、ポリメチン、メロシアニン、イミダゾールキレート化オキシノイド化合物、キナクリドン、ルブレン等およびそれらの誘導体があげられる。
【0085】
本有機EL素子における発光層中には、本発明の有機EL素子用材料の他に、必要に応じて、他の発光材料やドーピング材料のみならず、先に述べた正孔注入材料や電子注入材料を二種類以上組み合わせて使用することもできる。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良い。
【0086】
さらに、本発明の有機EL素子の陽極に使用される導電性材料は、4eVより大きな仕事関数を持つものが適しており、そのようなものとしては、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、パラジウム等およびそれらの合金、ITO基板、NESA基板と称される酸化スズ、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ポリマーがあげられる。
【0087】
また、本発明の有機EL素子の陰極に使用される導電性材料は、4eVより小さな仕事関数を持つものが適しており、そのようなものとしては、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、フッ化リチウム、ルテニウム、マンガン等およびそれらの合金があげられる。ここで、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あげられるが、これらに限定されるものではない。合金の比率は、調製時の加熱温度、雰囲気、真空度により制御可能なため、適切な比率からなる合金が調製可能である。これら陽極および陰極は、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良い。
【0088】
本発明の有機EL素子を効率良く発光させるためには、素子を構成する材料は素子の発光波長領域において充分透明であることが望ましく、同時に基板も透明であることが望ましい。透明電極は、上記の導電性材料を使用して蒸着やスパッタリング等の方法で作成することができる。特に、発光面の電極は、光透過率が10%以上であることが望ましい。基板は、機械的、熱的強度を有し、透明であれば特に限定されるものではないが、例えば、ガラス基板、ポリエチレン、ポリエーテルサルフォン、ポリプロピレン等の透明性ポリマーが推奨される。
【0089】
また、本発明の有機EL素子の各層の形成方法としては、真空蒸着、スパッタリング、プラズマ、イオンプレーティング等の乾式成膜法、もしくはスピンコーティング、ディッピング、フローコーティング等の湿式成膜法のいずれかの方法を適用することができる。各層の膜厚は特に限定されるものではないが、適切な膜厚に設定する必要がある。膜厚が厚すぎると、一定の光出力を得るために大きな印加電圧が必要となり効率が悪くなる。逆に膜厚が薄すぎると、ピンホール等が発生し、電界を印加しても充分な発光輝度が得ら難くなる。したがって、通常の膜厚は、1nmから1μmの範囲が適しているが、10nmから0.2μmの範囲がより好ましい。
【0090】
湿式成膜法の場合、各層は、それを構成する材料をトルエン、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または分散して薄膜を形成する。ここで用いられる溶媒は単一あるいは混合したもののいずれでも構わない。また、いずれの湿式成膜法においても、成膜性向上、膜のピンホール防止等のため適切なポリマーや添加剤を使用しても良い。このようなポリマーとしては、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ポリマー、ポリ−N−ビニルカルバゾール、ポリシラン等の光導電性ポリマー、ポリチオフェン、ポリピロール等の導電性ポリマーを挙げることができる。また、添加剤としては、酸化防止剤、紫外線吸収剤、可塑剤等をあげることができる。本発明の材料を湿式で成膜する際には、各化合物の分子間の親和性が良いため、単独では凝集性が高く膜が不均一になりやすい化合物でも、凝集性の低い誘導体との混合材料にすることにより良好な膜を得ることができる。
【0091】
また、本発明により得られた有機EL素子の温度、湿度、雰囲気等に対する安定性向上のために、さらに素子の表面に保護層を設けたり、シリコンオイル、ポリマー等により素子全体を被覆しても良い。
【0092】
以上述べたように、本有機EL素子用材料を用いて作成した有機EL素子は、発光効率、最大発光輝度等の特性を向上させることが可能である。また、本有機EL素子は、低い駆動電圧で実用的に使用可能の発光輝度が得られるため、従来まで大きな問題であった劣化も低減させることが可能である。故に、本有機EL素子は、壁掛けテレビ等のフラットパネルディスプレイや平面発光体として、さらには、複写機やプリンター等の光源、液晶ディスプレイや計器類等の光源、表示板、標識灯等への応用が考えられる。
【0093】
【実施例】
以下、実施例にて本発明を具体的に説明するが、本発明は下記実施例に何ら限定されるものではない。はじめに、実施例に先立って本発明の有機EL素子用材料の合成例を述べる。
【0094】
合成例1
化合物(3)の合成方法
トルエン300ml中に、4−ブロモビフェニル30.8g、3−アミノペリレン16.0g、ナトリウム-t-ブトキシド13.8g、酢酸パラジウム0.67gおよびトリ-t-ブチルホスフィン2.43gを加え、窒素雰囲気下、攪拌しながら2時間加熱還流した。放冷後濾過し、濾液を濃縮してシリカゲルを用いたカラムクロマトグラフィーにより精製し、化合物(3)26.1gを得た。マススペクトル、NMRスペクトル、元素分析により構造を確認した。第1図にCDCl3溶液中で測定した化合物(3)の1H−NMRスペクトル(テトラメチルシランの吸収ピークを基準とする)を示す。
【0095】
合成例2
化合物(7)の合成方法
トルエン300ml中に、4−メチル−2’−ブロモビフェニル32.7g、3−アミノペリレン16.0g、ナトリウム-t-ブトキシド13.8g、酢酸パラジウム0.67gおよびトリ-t-ブチルホスフィン2.43gを加え、窒素雰囲気下、攪拌しながら2時間加熱還流した。放冷後濾過し、濾液を濃縮してシリカゲルを用いたカラムクロマトグラフィーにより精製し、化合物(7)22.1gを得た。マススペクトル、NMRスペクトル、元素分析により構造を確認した。
【0096】
合成例3
化合物(9)の合成方法
トルエン300ml中に、2−メチル−4’−ブロモビフェニル32.7g、3−アミノペリレン16.0g、ナトリウム-t-ブトキシド13.8g、酢酸パラジウム0.67gおよびトリ-t-ブチルホスフィン2.43gを加え、窒素雰囲気下、攪拌しながら2時間加熱還流した。放冷後濾過し、濾液を濃縮してシリカゲルを用いたカラムクロマトグラフィーにより精製し、化合物(9)27.1gを得た。マススペクトル、NMRスペクトル、元素分析により構造を確認した。
【0097】
以下に本発明の化合物を用いた実施例を示す。本例では、特に断りのない限り、混合比は全て重量比を示す。また、電極面積2mm×2mmの有機EL素子の特性を測定した。尚、実施にあたって下記に示す公知の材料を用いた。
(比較化合物A)
【0098】
【化6】
【0099】
(比較化合物B)
【0100】
【化7】
【0101】
(比較化合物C)
【0102】
【化8】
【0103】
(比較化合物D)
【0104】
【化9】
【0105】
(DCJTB)
【0106】
【化10】
【0107】
実施例1
洗浄したITO電極付きガラス板上に、発光材料として表1の化合物(1)、2,5−ビス(1−ナフチル)−1,3,4−オキサジアゾール、ポリカーボネート樹脂(帝人化成:パンライトK−1300)を1:2:10の重量比でテトラヒドロフランに溶解させ、スピンコーティング法により膜厚100nmの発光層を得た。その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚150nmの電極を形成して有機EL素子を得た。この素子の発光特性は、直流電圧10Vでの発光輝度600(cd/m2)、最大発光輝度750(cd/m2)、発光効率0.48(lm/W)の発光が得られた。
【0108】
実施例2
洗浄したITO電極付きガラス板上に、N,N’―(3―メチルフェニル)―N,N’―ジフェニル―1,1’―ビフェニル-4,4’―ジアミン(TPD)とポリビニルカルバゾール(PVK)を1:1の重量比で1,2−ジクロロエタンに溶解させ、スピンコーティング法により膜厚50nmの正孔注入層を得た。次いで、表1の化合物(8)を蒸着し膜厚60nmの電子注入型発光層を作成し、その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚100nmの電極を形成して有機EL素子を得た。この素子の発光特性は、直流電圧10Vでの発光輝度1200(cd/m2)、最大発光輝度1800(cd/m2)、発光効率0.69(lm/W)の発光が得られた。
【0109】
実施例3
洗浄したITO電極付きガラス板上に、TPDとポリビニルカルバゾール(PVK)を1:1の重量比で1,2−ジクロロエタンに溶解させ、スピンコーティング法により膜厚50nmの正孔注入層を得た。次いで、表1の化合物(10)とトリス(8−ヒドロキシキノリナート)アルミニウム錯体(Alq3)との1:50の重量比からなる混合物を蒸着し、膜厚60nmの電子注入型発光層を作成し、その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚100nmの電極を形成して有機EL素子を得た。この素子の発光特性は、直流電圧10Vでの発光輝度2200(cd/m2)、最大発光輝度3200(cd/m2)、発光効率1.3(lm/W)の発光が得られた。
【0110】
実施例4
洗浄したITO電極付きガラス板上に、表1の化合物(20)を塩化メチレンに溶解させ、スピンコーティング法により膜厚50nmの正孔注入型発光層を得た。次いで、ビス(2−メチル−8−ヒドロキシキノリナート)(1−ナフトラート)ガリウム錯体を真空蒸着して膜厚40nmの電子注入層を作成し、その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚100nmの電極を形成して有機EL素子を得た。電子注入層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧6Vでの発光輝度3200(cd/m2) 、最大発光輝度12600(cd/m2)、発光効率2.3(lm/ W)の発光が得られた。
【0111】
実施例5
洗浄したITO電極付きガラス板上に、表1の化合物(29)を真空蒸着して膜厚50nmの正孔注入型発光層を得た。次いで、ビス(2−メチル−8−ヒドロキシキノリナート)(p−シアノフェノラート)ガリウム錯体を真空蒸着して膜厚30nmの電子注入層を作成し、その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚100nmの電極を形成して有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧6Vでの発光輝度4300(cd/m2)、最大発光輝度13400(cd /m2)、発光効率2.5(lm/W)の発光が得られた。
【0112】
実施例6
洗浄したITO電極付きガラス板上に、TPDを真空蒸着して膜厚20nmの正孔注入層を得た。次いで、表1の化合物(47)を蒸着し膜厚40nmの発光層を作成し、次いでAlq3を蒸着して膜厚30nmの電子注入層を得た。その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚200nmの電極を形成して有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧6Vで発光輝度7100(cd/m2)の発光が得られた。また、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は1000時間であった。
【0113】
比較例1
化合物(47)の代わりに前記比較化合物Aを成膜して用いる以外は、実施例6と同様の方法で有機EL素子を作製した。この素子は直流電圧6Vでの発光輝度は1600(cd/m2)であった。また、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は260時間であった。
【0114】
実施例7
洗浄したITO電極付きガラス板上に、TPDを真空蒸着して膜厚40nmの正孔注入層を得た。次いで、表1の化合物(53)とAlq3を1:50(重量比)の組成比で共蒸着して膜厚30nmの発光層を得た。さらにAlq3を蒸着して膜厚30nmの電子注入層を得た。その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚200nmの電極を形成して有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧6Vでの発光輝度が7000(cd/m2)、20Vでの発光輝度が46000(cd/m2)の発光が得られた。また、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は1000時間であった。
【0115】
比較例2
化合物(53)の代わりに前記比較化合物Cを成膜して用いる以外は、実施例15と同様の方法で有機EL素子を作製した。この素子は直流電圧20Vでの発光輝度は21000(cd/m2)であった。また、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は240時間であった。
【0116】
実施例8〜34および比較例3〜6
洗浄したITO電極付きガラス板上に、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(α−NPD)を真空蒸着して膜厚30nmの正孔注入層を形成した。次いで、表1の化合物を真空蒸着し、膜厚30nmの発光層を得た。さらに、ビス(2−メチル−8−ヒドロキシキノリナート)(フェノラート)ガリウム錯体を真空蒸着して膜厚30nmの電子注入層を作成し、その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚100nmの電極を形成して有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子の発光特性を表2に示す。本実施例の有機EL素子は全て、最大発光輝度35000(cd/m2)以上の高い輝度特性を示した。同様に比較例として、前記比較化合物A〜Dを成膜して用いる以外は、実施例8と同様の方法で有機EL素子を作製した。この素子の発光特性を表2に併せて示す。いずれの場合も、最大発光輝度、最大発光効率共に、本実施例で作成した素子よりも劣っていることは明らかである。
【0117】
【表2】
【0118】
実施例37
洗浄したITO電極付きガラス板上に、α−NPDを真空蒸着して膜厚20nmの正孔注入層を得た。次いで、表1の化合物(9)とAlq3を1:50の重量比で共蒸着して膜厚40nmの発光層を作成し、次いでAlq3を蒸着して膜厚30nmの電子注入層を得た。その上にまず、フッ化リチウム(LiF)を0.5nm、さらにアルミニウム(Al)を200nm真空蒸着によって電極を形成して有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧7Vでの発光輝度6700(cd/m2)、最大発光輝度42100(cd/m2)、発光効率3.9(lm/W)の発光が得られた。
【0119】
実施例38
発光層として、表1の化合物(1)と化合物(3)を1:1の重量比率で蒸着した膜厚30nmの薄膜を設ける以外は、実施例8と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度6300(cd/m2)、最大発光輝度36500(cd/m2)、発光効率3.8(lm/ W)の発光が得られた。
【0120】
実施例39
発光層として、表1の化合物(11)とビス(2−メチル−8−ヒドロキシキノリナート)(フェノラート)ガリウム錯体を1:50の重量比率で蒸着した膜厚30nmの薄膜を設ける以外は、実施例8と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度6500(cd/m2)、最大発光輝度38300(cd /m2)、発光効率3.9(lm/W)の発光が得られた。
【0121】
実施例40
発光層として、表1の化合物(16)とα−NPDを1:10の重量比率で蒸着した膜厚30nmの薄膜を設ける以外は、実施例8と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度7100(cd/m2)最大発光輝度41200(cd/m2)、発光効率4.0(lm/ W)の発光が得られた。
【0122】
実施例41
発光層として、表1の化合物(28)と2,3,6,7,10,11−ヘキサメトキシトリフェニレンを1:10の重量比率で蒸着した膜厚30nmの薄膜を設ける以外は、実施例8と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度7200(cd/m2)最大発光輝度42100(cd/m2)、発光効率4.1(lm/ W)の発光が得られた。
【0123】
実施例42
発光層として、表1の化合物(3)とDCJTBを100:5の重量比率で蒸着した膜厚30nmの薄膜を設ける以外は、実施例8と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度5400(cd/m2)最大発光輝度37800(cd/m2)、発光効率3.2(lm/ W)の発光が得られた。
【0124】
実施例43
洗浄したITO電極付きガラス板上に、α−NPDを真空蒸着して、膜厚40nmの正孔注入層を得た。次いで、表1の化合物(3)を真空蒸着して膜厚10nmの第一発光層を形成した後、表1の化合物(33)を真空蒸着して膜厚30nmの第二発光層を作成し、さらにビス(2−メチル−8−ヒドロキシキノリナート)(フェノラート)ガリウム錯体を真空蒸着して膜厚30nmの電子注入層を作成し、その上に、マグネシウムと銀を10:1(重量比)で混合した合金で膜厚100nmの電極を形成して有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧7Vでの発光輝度6500(cd/m2)、最大発光輝度38900(c d/m2)、発光効率3.8(lm/W)の発光が得られた。
【0125】
実施例44
洗浄したITO電極付きガラス板上に、4,4’,4”−トリス[N−(3−メチルフェニル)−N−フェニルアミノ]トリフェニルアミンを真空蒸着して、膜厚60nmの第一正孔注入層を得た。次いで、α−NPDを真空蒸着して、膜厚20nmの第二正孔注入層を得た。さらに、表1の化合物(14)を真空蒸着して、膜厚10nmの発光層を作成し、さらにAlq3を真空蒸着して膜厚30nmの電子注入層を作成した。その上に、LiFを0.2nm、次いでAlを150nm真空蒸着することで電極を形成して、有機EL素子を得た。各層は10-6Torrの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧7Vでの発光輝度8600(cd/m2)、最大発光輝度43500(c d/m2)、発光効率4.3(lm/W)の発光が得られた。
【0126】
実施例45
発光層として、表1の化合物(24)とAlq3を1:100の重量比率で蒸着した膜厚30nmの薄膜を設ける以外は、実施例44と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度32800(cd/m2)、発光効率3.6(cd/A)の発光が得られた。また、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は1200時間であった。
【0127】
比較例7
化合物(24)の代わりに前記比較化合物Bを用いる以外は、実施例45と同様の方法で有機EL素子を作製した。この素子は直流電圧7Vでの発光輝度は13000(cd/m2)であり、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は250時間であった。
【0128】
実施例46
4,4’,4”−トリス[N−(3−メチルフェニル)−N−フェニルアミノ]トリフェニルアミンの代わりに銅フタロシアニンの膜厚20nmの正孔注入層を設ける以外は、実施例45と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度30100(cd/m2)、発光効率3.9(cd/A)の発光が得られた。また、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は1500時間であった。
【0129】
比較例8
化合物(24)の代わりに前記比較化合物Dを用いる以外は、実施例46と同様の方法で有機EL素子を作製した。この素子は、直流電圧7Vでの発光輝度15300(cd/m2)であり、発光輝度500(cd/m2)で定電流駆動したときの半減寿命は270時間であった。
【0130】
以上述べた実施例から明らかなように、本発明の有機EL素子は発光効率、発光輝度の向上と長寿命化を達成するものであり、併せて使用される発光材料、ドーピング材料、正孔注入材料、電子注入材料、増感剤、樹脂、電極材料等および素子作製方法を限定するものではない。
【0131】
【発明の効果】
本発明の有機EL素子用材料に用いて作成した有機EL素子は、従来に比べて高輝度かつ長寿命であるため、壁掛けテレビ等のフラットパネルディスプレイや平面発光体として好適に使用することができ、複写機やプリンター等の光源、液晶ディスプレイや計器類等の光源、表示板、標識灯等への応用が可能である。
【図面の簡単な説明】
【図1】合成例1で得た化合物(3)のCDCl3溶液中での1H−NMRスペクトル(テトラメチルシランの吸収ピークを基準とする)を示す。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a material for an organic electroluminescence (EL) element used for a flat light source and display, and an organic EL element using the same. More specifically, the present invention relates to a material for an organic EL element having a long life and capable of obtaining yellow-red high luminance light emission and an organic EL element using the same.
[0002]
[Prior art]
An EL element using an organic substance is considered to be promising for use as an inexpensive large-area full-color display element of a solid light emitting type, and many developments have been made. In general, an 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, holes are injected from the anode side, these electrons recombine with holes in the light emitting layer, and the energy level is in the conduction band. This is a phenomenon in which energy is released as light when returning from the valence band to the valence band.
[0003]
Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic EL elements. Further, the characteristic deterioration has been remarkably not put into practical use. In recent years, an organic EL device in which a thin film containing an organic compound having a high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less has been reported and attracted attention (Appl. Phys. Lett., Vol. 51, (See page 913, published in 1987). This method uses a metal chelate complex as a light emitting layer and an amine compound as a hole injection layer to obtain high luminance green light emission. The luminance is several thousand (cd / m) at a DC voltage of 6 to 10V.2), The maximum luminous efficiency is 1.5 (lm / W), and the performance is close to the practical range.
[0004]
Among organic EL elements, the light-emitting material for organic EL elements for obtaining yellow to red light emission is particularly described in C.I. H. Chen et al., Macromol. Symp. 125, 34-36 and 49-58, published in 1997, 4H-pyran derivatives such as DCM, DCJ, DCJT, and DCJTB emit light from yellow to red light for organic EL devices. Although reported as a material, there was a problem of low emission luminance.
[0005]
On the other hand, as for the light-emitting material for organic EL elements having a perylene structure, for example, mono- and diaminoperylene compounds described in JP-A Nos. 11-144869, 2001-11031, and 2001-176664 Etc. are known.
[0006]
[Problems to be solved by the invention]
None of the light-emitting materials for organic EL devices for obtaining yellow to red high-luminance emission described in the prior art has a drawback that it does not have sufficient emission luminance and has a short lifetime. On the other hand, since perylene has a highly planar molecular structure, undesirable phenomena such as concentration quenching tend to occur when it is used as a light emitting material for organic EL elements. Therefore, as described in the prior art, improvements such as increasing the number of amino groups bonded to perylene or introducing a sterically bulky substituent have been attempted, but with the accompanying increase in molecular weight, There is a concern that workability deteriorates, such as a decrease in solubility in a solvent and poor vapor deposition at the time of device preparation. Therefore, there has been a demand for a material for an organic EL element having a much higher light emission luminance and a longer lifetime.
[0007]
[Means for Solving the Problems]
As a result of intensive studies to solve the above problems, the present inventors have arrived at the present invention.
That is, this invention relates to the material for organic electroluminescent elements characterized by being a compound represented by the following general formula [1].
General formula [1]
[Chemical Formula 3]
[Wherein Ar1Is a substituted or unsubstituted 3-perylenyl group, R1And R2Is a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aliphatic heterocyclic group, and a substituted or unsubstituted A monovalent organic residue selected from the monovalent aromatic heterocyclic groups of: R1And R2Is at least one monovalent organic residue represented by the following general formula [2].]
General formula [2]
[Formula 4]
[Wherein Ar2Is a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group, ArThreeIs a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group, X1Is a direct bond, O, S, ═C (RThree) RFour, = Si (RFive) R6(Where R isThree~ R6Is a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic hydrocarbon group). ]
[However, the substitution in the general formula [1] and the general formula [1] and the general formula [2] is a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aliphatic complex. Ring group, monovalent aromatic heterocyclic group, halogen atom, cyano group, alkoxyl group, aryloxy group, alkylthio group, arylthio group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group Is to be replaced with one of ]
The present invention also provides Ar1Is an unsubstituted 3-perylenyl group. The present invention relates to the material for an organic electroluminescence element.
The present invention also provides R1And R2These are all the monovalent organic residues represented by the general formula [2].
In addition, the present invention relates to X1Is a direct bond, and relates to the material for an organic electroluminescence element.
Further, the present invention provides an organic electroluminescence device in which a single layer or a multilayer organic layer is formed between a pair of electrodes composed of an anode and a cathode, and at least one layer is a layer containing the organic electroluminescence device material. The present invention relates to an organic electroluminescence element.
Further, the present invention provides an organic electroluminescent device in which at least one light emitting layer is formed between a pair of electrodes composed of an anode and a cathode, wherein the light emitting layer is a layer containing the material for an organic electroluminescent device. The present invention relates to an electroluminescence element.
The present invention further relates to the above-mentioned organic electroluminescence device, wherein at least one electron injection layer is formed between the light emitting layer and the cathode.
[0008]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail. First, the monoamine compound represented by the general formula [1], which is a material for an organic EL device of the present invention, will be described.
[0009]
First, Ar in the general formula [1]1Represents a substituted or unsubstituted 3-perylenyl group. These perylenyl groups may be further substituted with other substituents. Examples of such a substituent include a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aliphatic heterocyclic group, a monovalent aromatic heterocyclic group, a halogen atom, a cyano group, Alkoxyl group, aryloxy group, alkylthio group, arylthio group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl groupOne ofIs given.
[0010]
Here, the monovalent aliphatic hydrocarbon group refers to a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, such as an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group. Can be given.
[0011]
Therefore, as the alkyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, C1-C18 alkyl groups, such as a decyl group, a dodecyl group, a pentadecyl group, and an octadecyl group, are mentioned.
[0012]
Examples of the alkenyl group include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-octenyl group, 1-decenyl group, 1 -An alkenyl group having 2 to 18 carbon atoms such as an octadecenyl group.
[0013]
Examples of the alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-octynyl group, 1-decynyl group and 1-octadecynyl group. Examples thereof include alkynyl groups having 2 to 18 carbon atoms.
[0014]
In addition, the cycloalkyl group has a carbon number such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-bornyl group, 2-isobornyl group, 1-adamantyl group. Examples thereof include 3 to 18 cycloalkyl groups.
[0015]
Furthermore, examples of the monovalent aromatic hydrocarbon group include monovalent monocyclic, condensed ring, and ring-aggregated aromatic hydrocarbon groups having 6 to 30 carbon atoms. Here, as a monovalent monocyclic aromatic hydrocarbon group having 6 to 30 carbon atoms, phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl And monovalent monocyclic aromatic hydrocarbon groups having 6 to 30 carbon atoms such as a group and a mesityl group.
[0016]
Examples of the monovalent condensed ring aromatic hydrocarbon group include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, 1-acenaphthyl group, 2-azurenyl group, 1-pyrenyl group, 2-triphenylyl group, 1-pyrenyl group, 2-pyrenyl group, 1-perylenyl group, 2-perylenyl group, 3-perenylenyl group, 2-trephenylenyl group, Examples thereof include monovalent condensed ring hydrocarbon groups having 10 to 30 carbon atoms such as 2-indenyl group, 1-acenaphthylenyl group, 2-naphthacenyl group, and 2-pentacenyl group.
[0017]
The monovalent ring-aggregated aromatic hydrocarbon group has 12 carbon atoms such as o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, terphenylyl group, 7- (2-naphthyl) -2-naphthyl group and the like. To 30 monovalent ring-assembled hydrocarbon groups.
[0018]
Examples of the monovalent aliphatic heterocyclic group include monovalent aliphatic heterocyclic groups having 3 to 18 carbon atoms such as 3-isochromanyl group, 7-chromanyl group, and 3-coumarinyl.
[0019]
Examples of the monovalent aromatic heterocyclic group include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-benzofuryl group, 2-benzothienyl group, 2-pyridyl group, 3 -Pyridyl group, 4-pyridyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3 -Isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-pyrimidinyl group, 2-pyrazinyl group, 2-quinazolinyl group, 2-quinoxalinyl group, 2 -C3-C30 monovalent | monohydric aromatic heterocyclic groups, such as oxazolyl group and 2-thiazolyl group, are mention | raise | lifted.
[0020]
In addition, examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
[0021]
The alkoxyl group includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a tert-butoxy group, an octyloxy group, a tert-octyloxy group, a 2-bornyloxy group, a 2-isobornyloxy group, and a 1-adamantyl group. C1-C18 alkoxyl groups, such as an oxy group, are mention | raise | lifted.
[0022]
Examples of the aryloxy group include aryloxy groups having 6 to 30 carbon atoms such as a phenoxy group, a 4-tert-butylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and a 9-anthryloxy group. .
[0023]
Examples of the alkylthio group include C1-C18 alkylthio groups such as a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group.
[0024]
Examples of the arylthio group include arylthio groups having 6 to 30 carbon atoms such as a phenylthio group, a 2-methylphenylthio group, and a 4-tert-butylphenylthio group.
[0025]
Examples of the acyl group include C2-C18 acyl groups such as an acetyl group, a propionyl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a toluoyl group, an anisoyl group, and a cinnamoyl group.
[0026]
Moreover, as an alkoxycarbonyl group, C2-C18 alkoxycarbonyl groups, such as a methoxycarbonyl group, an ethoxycarbonyl group, a benzyloxycarbonyl group, are mention | raise | lifted.
[0027]
Examples of the aryloxycarbonyl group include C2-C18 aryloxycarbonyl groups such as a phenoxycarbonyl group and a naphthyloxycarbonyl group.
[0028]
Moreover, as an alkylsulfonyl group, C2-C18 alkylsulfonyl groups, such as a mesyl group, an ethylsulfonyl group, a propylsulfonyl group, are mention | raise | lifted.
[0029]
Examples of the arylsulfonyl group include C2-C18 arylsulfonyl groups such as a benzenesulfonyl group and a p-toluenesulfonyl group.
[0030]
The substituents described above may be further substituted with other substituents.Yes.
[0031]
A in general formula [1] described abover 1as,An unsubstituted 3-perylenyl group is particularly preferred. The reason for this is that when the amino group is bonded to the 3-position of perylene, the angle between the perylene ring and the amino group is kept relatively on the same plane, so that the fluorescence becomes strong and the organic electroluminescence device This is because it is considered that the light emission luminance when used as is improved.
[0032]
Among the substituted 3-perylenyl groups, preferred substituents include alkyl groups, monovalent aromatic hydrocarbon groups, monovalent aromatic heterocyclic groups, aryloxy groups, and arylthio groups, and particularly preferred substitutions. Examples of the group include an alkyl group, a monovalent monocyclic aromatic hydrocarbon group, a monovalent condensed ring aromatic hydrocarbon group, a monovalent ring assembly aromatic hydrocarbon group, and a monovalent aromatic heterocyclic group. It is done.
[0033]
Moreover, 1-18 are preferable as a carbon number of a substituent among the preferable substituents described above, and 1-12 are more preferable. The reason for this is that if the carbon number of these substituents increases, the solubility in the solvent becomes poor, so that not only purification becomes difficult, but also the workability at the time of device creation deteriorates, and an attempt is made to create a device by vapor deposition. This is because there may be a concern that the vapor deposition property is deteriorated.
[0034]
Next, R in the general formula [1]1And R2Will be described. R1And R2Is a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aliphatic heterocyclic group, a substituted or unsubstituted 1 A monovalent organic residue selected from valent aromatic heterocyclic groups, R1And R2Is at least one monovalent organic residue represented by the general formula [2]. The substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, the substituted or unsubstituted monovalent aliphatic heterocyclic group, the substituted or unsubstituted The monovalent aromatic heterocyclic group is Ar1A substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aliphatic heterocyclic group, substituted or It is synonymous with an unsubstituted monovalent aromatic heterocyclic group.
[0035]
Here, the general formula [2] will be described. First, Ar in the general formula [2]2Represents a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent aromatic heterocyclic group. The substituent here is Ar.1It is synonymous with the substituent demonstrated in (2), and two or more substituents may combine with each other to form a ring.
[0036]
Here, the divalent aromatic hydrocarbon group means a divalent monocyclic or condensed ring or ring-aggregated aromatic hydrocarbon group. For example, a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a p-tell. Phenyl-4,4 ″ -diyl group, m-terphenyl-3,3 ″ -diyl group, m-terphenyl-4,4′-diyl group, [1,2′-binaphthalene] -4,5 Examples thereof include divalent aromatic hydrocarbon groups having 6 to 30 carbon atoms such as' -diyl.
[0037]
The divalent aromatic heterocyclic group means a divalent monocyclic ring, condensed ring, or ring assembly aromatic heterocyclic group. For example, 2,5-furylene group, 2,5-thienylene group, 2, 5-pyridylene group, 2,4-pyridylene group, 2,3-pyridylene group, 2,5-pyrazinylene group, 2,4-quinolylene group, 2,6-quinolylene group, 1,4-isoquinolylene group, 2,3 -A C4-C30 bivalent aromatic heterocyclic group, such as a quinoxalinylene group.
[0038]
Ar described above2Among the divalent aromatic hydrocarbon groups or aromatic heterocyclic groups in the formula, preferred are C6-C12 divalent aromatic hydrocarbon groups such as a phenylene group, a naphthylene group, and a biphenylene group. .
[0039]
Further, Ar in the general formula [2]ThreeRepresents a substituted or unsubstituted monovalent aromatic hydrocarbon group or a substituted or unsubstituted monovalent aromatic heterocyclic group. The substituent here is Ar.1It is synonymous with the substituent demonstrated in (2), and two or more substituents may combine with each other to form a ring. Further, the substituted or unsubstituted monovalent aromatic hydrocarbon group and the substituted or unsubstituted monovalent aromatic heterocyclic group referred to here are respectively Ar1These are synonymous with the substituted or unsubstituted monovalent aromatic hydrocarbon group and the substituted or unsubstituted monovalent aromatic heterocyclic group described in the above.
[0040]
Furthermore, X in the general formula [2]1Is a direct bond, O, S, ═C (RThree) RFour, = Si (RFive) R6(Where R isThree~ R6Is a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic hydrocarbon group). Where RThree~ R6The substituted or unsubstituted monovalent aliphatic hydrocarbon group in FIG. 5 is a substituted or unsubstituted monovalent aromatic hydrocarbon group.1Synonymous with the substituted or unsubstituted monovalent aliphatic hydrocarbon group and the substituted or unsubstituted monovalent aromatic hydrocarbon group described in the above, and two or more substituents are bonded to each other to form a ring. It does not matter.
[0041]
R in general formula [1]1And R2For example, at least one monovalent organic residue represented by the general formula [2] may be used, but any monovalent organic residue represented by the general formula [2] is preferable. This is because R1And R2However, in the case of a monovalent organic residue represented by the general formula [2], the molecule becomes three-dimensional while the angle between the perylene ring and the amino group is kept relatively on the same plane. This is because an undesirable phenomenon such as quenching is suppressed, and it is considered that the light emission luminance when used as an organic electroluminescence element is improved. Furthermore, X in the general formula [2]1When is a direct bond, the conjugated system in the molecule becomes large, and it is considered that the emission luminance is improved, which is particularly preferable.
[0042]
The monoamine compound represented by the general formula [1] of the present invention has been described above. The molecular weight of the monoamine compound of the present invention is preferably 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. The reason for this is that, if the molecular weight is large, the solubility in the solvent becomes poor, so not only purification becomes difficult, but the workability at the time of device creation is deteriorated, and the vapor deposition property when the device is created by vapor deposition This is because there is a concern that it will worsen.
[0043]
The element created by using the organic EL element material of the present invention alone in the light emitting layer usually exhibits yellow to orange high-intensity light emission, but when used with an appropriate doping material as described later, It is possible to extend the emission color to red while maintaining high luminance.
[0044]
Hereinafter, representative examples of compounds that can be used as the material for the organic EL device of the present invention are shown in Table 1, but the present invention is not limited to these (however, in Table 1, t-Bu is A tertiary butyl group, and Ph represents a phenyl group).
[0045]
[Table 1]
[0046]
[0047]
[0048]
[0049]
[0050]
[0051]
[0052]
[0053]
[0054]
[0055]
[0056]
[0057]
[0058]
[0059]
[0060]
[0061]
[0062]
[0063]
[0064]
[0065]
[0066]
[0067]
[0072]
By the way, an organic EL element is an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode. Here, a single layer type organic EL element has a light emitting layer made of a light emitting material between an anode and a cathode. Have. On the other hand, the multilayer organic EL device has (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole injection layer / light emitting layer / electron injection layer). / Cathode) is an organic EL element laminated in a multilayer structure. The organic EL device material of the present invention can be used in any of the above-mentioned layers, but can be suitably used as a light-emitting material for these single-layer or multilayer organic EL devices. In particular, when a single-layer organic EL device is prepared using the light emitting material for the organic EL device, a hole injection material or an electron for efficiently transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. An injection material can be included.
[0073]
Here, the hole injection material indicates an excellent hole injection effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and It means a compound excellent in thin film forming property. Examples of such hole injection materials include phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazoles, triazoles, imidazoles, imidazolones, imidazolethiones, pyrazolines, pyrazolones, tetrahydroimidazoles, oxazoles, oxadiazoles Hydrazone, acyl hydrazone, polyarylalkane, stilbene, butadiene, benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and their derivatives, and polyvinylcarbazole, polysilane, conductive polymer, etc. The present invention is not limited to these examples.
[0074]
Among the above hole injection materials, particularly effective hole injection materials include aromatic tertiary amine derivatives or phthalocyanine derivatives. Examples of 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-methylphenyl)- 1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-(methylphenyl) ) -N, N ′-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, or these Aromatic tertiary amine skeleton Oligomers or polymers having, and the like. Moreover, as a phthalocyanine (Pc) derivative, H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2Examples thereof include phthalocyanine derivatives and naphthalocyanine derivatives such as SiPc, (HO) AlPc, (HO) GaPc, VOPc, TiOPc, MoOPc, and GaPc-O-GaPc. The hole injection material described above can be further sensitized by adding an electron accepting material.
[0075]
On the other hand, the electron injection material shows an excellent electron injection effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the hole injection layer or the hole injection material, and is a thin film. It means a compound excellent in formability. Examples of such electron injection materials include quinoline metal complexes, oxadiazoles, benzothiazole metal complexes, benzoxazole metal complexes, benzimidazole metal complexes, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadioxide. Examples thereof include azole, thiadiazole, tetrazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone and the like. An inorganic / organic composite material doped with a metal such as cesium in bathophenanthroline (for example, Proceedings of the Society of Polymer Science, Vol. 50, No. 4, page 660, issued in 2001) is an example of an electron injection material. However, the present invention is not limited to these.
[0076]
Among the electron injection materials, particularly effective electron injection materials include metal complex compounds and nitrogen-containing five-membered ring derivatives. Here, among the metal complex compounds, the compound represented by the following general formula [3] can be preferably used.
General formula [3]
[Chemical formula 5]
[Where Q1And Q2Each independently represents a substituted or unsubstituted hydroxyquinoline derivative or a substituted or unsubstituted hydroxybenzoquinoline derivative, and L represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, A substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group, -OR (where R is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted group, A substituted or unsubstituted aromatic heterocyclic group), -O-Ga-Q.Three(QFour(QThreeAnd QFourQ1 And Q2Means the same. Represents a ligand represented by ]
[0077]
Here, the general formula [3] will be described. Q of the compound represented by the general formula [3]1~ QFourIs a substituted or unsubstituted hydroxyquinoline derivative or a substituted or unsubstituted hydroxybenzoquinoline derivative. The substituent here is R in the general formula [1].1And R2It is synonymous with the substituent in.
[0078]
L represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. The substituent here is R in the general formula [1].1And R2It is synonymous with the substituent in. Examples of the substituted or unsubstituted cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecanyl group.
[0079]
Therefore, specific examples of the compound represented by the general formula [3] include bis (2-methyl-8-hydroxyquinolinate) (1-naphtholate) gallium complex, bis (2-methyl-8-hydroxyquinolinate). ) (2-Naphtholate) gallium complex, bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex, bis (2-methyl-8-hydroxyquinolinate) (4-cyano-1-naphtholate) Gallium complex, bis (2,4-dimethyl-8-hydroxyquinolinato) (1-naphtholato) gallium complex, bis (2,5-dimethyl-8-hydroxyquinolinato) (2-naphtholato) gallium complex, bis (2-Methyl-5-phenyl-8-hydroxyquinolinate) (phenolate) gallium complex, bis (2-methyl- -Cyano-8-hydroxyquinolinate) (4-cyano-1-naphtholate) gallium complex, bis (2-methyl-8-hydroxyquinolinato) chlorogallium complex, bis (2-methyl-8-hydroxyquinolinate) (Nato) (o-cresolate) gallium complex and the like, but the present invention is not limited thereto. The compound represented by the general formula [3] can be synthesized by the method described in JP-A-10-88,121.
[0080]
In addition, among the electron injection materials that can be used in the present invention, preferred metal complex compounds include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, Bis (8-hydroxyquinolinate) manganese, Tris (8-hydroxyquinolinato) aluminum, Tris (2-methyl-8-hydroxyquinolinato) aluminum, Tris (8-hydroxyquinolinato) gallium, Bis ( 10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc and the like.
[0081]
Among the electron injecting materials that can be used in the present invention, preferable nitrogen-containing five-membered derivatives include oxazole, thiazole, oxadiazole, thiadiazole, and triazole derivatives. Specifically, 2,5-bis ( 1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) -1,3, 4-oxadiazole, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1,3 , 4-oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene] 2 -(4'-tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) -1,3,4-thiadiazole, 1,4 -Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene, etc. The electron injecting material described above further includes an electron donating material. Can be sensitized.
[0082]
Moreover, the organic EL device material of the present invention can be used by doping into the light emitting layer. In this case, the organic EL device material is preferably contained in the range of 0.001 to 50% by weight, and more preferably in the range of 0.01 to 10% by weight with respect to the host material described below. More preferably.
[0083]
Host materials that can be used together with the organic EL device material of the present invention as a doping material include quinoline metal complexes, benzoquinoline metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, benzimidazole metal complexes, and benzotriazole metals. Electron transport materials such as complexes, imidazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and triazole derivatives. Or hole transporting materials such as stilbene derivatives, butadiene derivatives, benzidine type triphenylamine derivatives, styrylamine type triphenylamine derivatives, diaminoanthracene type triphenylamine derivatives, diaminophenanthrene type triphenylamine derivatives, and polyvinylcarbazole, Examples thereof include polymer materials of conductive polymers such as polysilane.
[0084]
Moreover, in the light emitting layer in this organic EL element, in addition to the material for organic EL elements of the present invention, two or more kinds of other light emitting materials and doping materials can be used in combination. In this case, the organic EL element material of the present invention may function as a host material. Other light-emitting materials and doping materials that can be used with the organic EL device material of the present invention include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenyl Butadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, Polymethine, merocyanine, imidazole chelating oxinoid compounds, quinacridone, rubrene, etc. and their derivatives It is below.
[0085]
In the light emitting layer of the present organic EL device, in addition to the organic EL device material of the present invention, not only other light emitting materials and doping materials, but also the above-described hole injection materials and electron injection materials are used. Two or more kinds of materials can be used in combination. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed with a layer configuration of two or more layers.
[0086]
Furthermore, the conductive material used for the anode of the organic EL element of the present invention is suitably one having a work function larger than 4 eV, such as carbon, aluminum, vanadium, iron, cobalt, nickel. , Tungsten, silver, gold, platinum, palladium and the like and alloys thereof, ITO substrates, metal oxides such as tin oxide and indium oxide called NESA substrates, and organic conductive polymers such as polythiophene and polypyrrole.
[0087]
Further, the conductive material used for the cathode of the organic EL device of the present invention is suitably one having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium. Lithium, lithium fluoride, ruthenium, manganese and the like and alloys thereof. Here, examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. Since the ratio of the alloy can be controlled by the heating temperature, atmosphere, and degree of vacuum at the time of preparation, an alloy having an appropriate ratio can be prepared. These anodes and cathodes may be formed with a layer structure of two or more layers if necessary.
[0088]
In order for the organic EL device of the present invention to emit light efficiently, the material constituting the device is preferably sufficiently transparent in the light emission wavelength region of the device, and at the same time, the substrate is preferably transparent. The transparent electrode can be prepared by a method such as vapor deposition or sputtering using the above conductive material. In particular, it is desirable that the light transmission surface electrode has a light transmittance of 10% or more. The substrate is not particularly limited as long as it has mechanical and thermal strength and is transparent. For example, a transparent polymer such as a glass substrate, polyethylene, polyethersulfone, and polypropylene is recommended.
[0089]
In addition, as a method for forming each layer of the organic EL element of the present invention, any one of a dry film forming method such as vacuum deposition, sputtering, plasma, and ion plating, or a wet film forming method such as spin coating, dipping, and flow coating is used. The method can be applied. The thickness of each layer is not particularly limited, but must be set to an appropriate thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. On the other hand, if the film thickness is too thin, pinholes and the like are generated, and it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied. Accordingly, the normal film thickness is suitably in the range of 1 nm to 1 μm, but more preferably in the range of 10 nm to 0.2 μm.
[0090]
In the case of a wet film forming method, each layer forms a thin film by dissolving or dispersing the material constituting it in an appropriate solvent such as toluene, chloroform, tetrahydrofuran, dioxane or the like. The solvent used here may be either a single solvent or a mixed solvent. In any wet film forming method, an appropriate polymer or additive may be used for improving the film forming property and preventing pinholes in the film. Examples of such polymers include insulating polymers such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and photoconductive materials such as poly-N-vinylcarbazole and polysilane. And conductive polymers such as conductive polymer, polythiophene, and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer. When the material of the present invention is wet-formed, the affinity between the molecules of each compound is good, so even if the compound alone is highly cohesive and the film tends to be non-uniform, it is mixed with a derivative with low cohesiveness. A good film can be obtained by using the material.
[0091]
In addition, in order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., a protective layer may be further provided on the surface of the device, or the entire device may be covered with silicon oil, polymer, etc. good.
[0092]
As described above, an organic EL element produced using the material for an organic EL element can improve characteristics such as light emission efficiency and maximum light emission luminance. In addition, since the organic EL element can emit light that can be practically used at a low driving voltage, it is possible to reduce deterioration that has been a major problem until now. Therefore, this organic EL device can be applied to flat panel displays such as wall-mounted televisions and flat light emitters, as well as light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. Can be considered.
[0093]
【Example】
EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example at all. First, prior to examples, a synthesis example of the organic EL element material of the present invention will be described.
[0094]
Synthesis example 1
Method for synthesizing compound (3)
In 300 ml of toluene, 30.8 g of 4-bromobiphenyl, 16.0 g of 3-aminoperylene, 13.8 g of sodium-t-butoxide, 0.67 g of palladium acetate and 2.43 g of tri-t-butylphosphine were added, and a nitrogen atmosphere The mixture was refluxed for 2 hours with stirring. The mixture was allowed to cool and then filtered. The filtrate was concentrated and purified by column chromatography using silica gel to obtain 26.1 g of compound (3). The structure was confirmed by mass spectrum, NMR spectrum and elemental analysis. Fig. 1 shows CDCl.ThreeOf compound (3) measured in solution11 shows an H-NMR spectrum (based on the absorption peak of tetramethylsilane).
[0095]
Synthesis example 2
Method for synthesizing compound (7)
In 300 ml of toluene, 32.7 g of 4-methyl-2'-bromobiphenyl, 16.0 g of 3-aminoperylene, 13.8 g of sodium-t-butoxide, 0.67 g of palladium acetate and 2.43 g of tri-t-butylphosphine And heated to reflux for 2 hours with stirring under a nitrogen atmosphere. The mixture was allowed to cool and then filtered, and the filtrate was concentrated and purified by column chromatography using silica gel to obtain 22.1 g of Compound (7). The structure was confirmed by mass spectrum, NMR spectrum and elemental analysis.
[0096]
Synthesis example 3
Method for synthesizing compound (9)
In 300 ml of toluene, 32.7 g of 2-methyl-4'-bromobiphenyl, 16.0 g of 3-aminoperylene, 13.8 g of sodium-t-butoxide, 0.67 g of palladium acetate and 2.43 g of tri-t-butylphosphine And heated to reflux for 2 hours with stirring under a nitrogen atmosphere. The mixture was allowed to cool and then filtered, and the filtrate was concentrated and purified by column chromatography using silica gel to obtain 27.1 g of Compound (9). The structure was confirmed by mass spectrum, NMR spectrum and elemental analysis.
[0097]
Examples using the compounds of the present invention are shown below. In this example, all mixing ratios indicate weight ratios unless otherwise specified. Moreover, the characteristic of the organic EL element with an electrode area of 2 mm × 2 mm was measured. In the implementation, the following known materials were used.
(Comparative Compound A)
[0098]
[Chemical 6]
[0099]
(Comparative Compound B)
[0100]
[Chemical 7]
[0101]
(Comparative Compound C)
[0102]
[Chemical 8]
[0103]
(Comparative Compound D)
[0104]
[Chemical 9]
[0105]
(DCJTB)
[0106]
[Chemical Formula 10]
[0107]
Example 1
On the washed glass plate with an ITO electrode, the compound (1) in Table 1 as a luminescent material, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, polycarbonate resin (Teijin Chemicals: Panlite) K-1300) was dissolved in tetrahydrofuran at a weight ratio of 1: 2: 10, and a light emitting layer having a thickness of 100 nm was obtained by a spin coating method. On top of this, an electrode having a thickness of 150 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 (weight ratio) to obtain an organic EL device. The light emission characteristics of this element are as follows: emission luminance at a DC voltage of 10 V (cd / m2), Maximum luminance 750 (cd / m)2), A light emission efficiency of 0.48 (lm / W) was obtained.
[0108]
Example 2
N, N '-(3-Methylphenyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine (TPD) and polyvinylcarbazole (PVK) on a cleaned glass plate with an ITO electrode ) Was dissolved in 1,2-dichloroethane at a weight ratio of 1: 1, and a hole injection layer having a thickness of 50 nm was obtained by spin coating. Next, the compound (8) in Table 1 is deposited to prepare a 60 nm-thickness electron-injection-type light-emitting layer, on which an electrode having a thickness of 100 nm is formed of an alloy in which magnesium and silver are mixed at a weight ratio of 10: 1. To obtain an organic EL device. The light emission characteristics of this element are as follows: light emission luminance at a DC voltage of 10 V (cd / m2), Maximum luminance 1800 (cd / m)2), A light emission efficiency of 0.69 (lm / W) was obtained.
[0109]
Example 3
On the washed glass plate with an ITO electrode, TPD and polyvinylcarbazole (PVK) were dissolved in 1,2-dichloroethane at a weight ratio of 1: 1, and a hole injection layer having a thickness of 50 nm was obtained by a spin coating method. Subsequently, the mixture which consists of a 1:50 weight ratio of the compound (10) of Table 1 and a tris (8-hydroxyquinolinate) aluminum complex (Alq3) was vapor-deposited, and the electron injection type light emitting layer with a film thickness of 60 nm was created. Then, an electrode having a thickness of 100 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 (weight ratio) to obtain an organic EL device. The light emission characteristics of this element are as follows: light emission luminance at a DC voltage of 10 V (cd / m 2)2), Maximum luminance of 3200 (cd / m)2), Emission with a luminous efficiency of 1.3 (lm / W) was obtained.
[0110]
Example 4
On the washed glass plate with an ITO electrode, the compound (20) in Table 1 was dissolved in methylene chloride, and a hole injection type light emitting layer having a film thickness of 50 nm was obtained by a spin coating method. Next, a bis (2-methyl-8-hydroxyquinolinate) (1-naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 40 nm, and then magnesium and silver are added 10: 1 ( An electrode having a film thickness of 100 nm was formed from an alloy mixed at a weight ratio to obtain an organic EL device. The electron injection layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element has an emission luminance of 3200 (cd / m at a DC voltage of 6 V).2), Maximum emission brightness 12600 (cd / m)2), A light emission efficiency of 2.3 (lm / W) was obtained.
[0111]
Example 5
On the washed glass plate with an ITO electrode, the compound (29) shown in Table 1 was vacuum-deposited to obtain a 50 nm-thick hole injection type light emitting layer. Next, a bis (2-methyl-8-hydroxyquinolinate) (p-cyanophenolate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 30 nm. An electrode having a thickness of 100 nm was formed from an alloy mixed at 1 (weight ratio) to obtain an organic EL element. Each layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element has an emission luminance of 4300 (cd / m) at a DC voltage of 6V.2), Maximum emission luminance 13400 (cd / m)2), Emission with a luminous efficiency of 2.5 (lm / W) was obtained.
[0112]
Example 6
TPD was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 20 nm. Subsequently, the compound (47) of Table 1 was vapor-deposited, the light emitting layer with a film thickness of 40 nm was created, then Alq3 was vapor-deposited, and the electron injection layer with a film thickness of 30 nm was obtained. On top of this, an electrode having a film thickness of 200 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 (weight ratio) to obtain an organic EL device. Each layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element has a direct-current voltage of 6 V and an emission luminance of 7100 (cd / m2) Was obtained. In addition, emission luminance of 500 (cd / m2) Had a half life of 1000 hours when driven at a constant current.
[0113]
Comparative Example 1
An organic EL device was produced in the same manner as in Example 6 except that the comparative compound A was used in place of the compound (47). This device has a luminance of 1600 (cd / m) at a DC voltage of 6V.2)Met. In addition, emission luminance of 500 (cd / m2) Was 260 hours when driven at a constant current.
[0114]
Example 7
TPD was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 40 nm. Next, the compound (53) in Table 1 and Alq3 were co-evaporated at a composition ratio of 1:50 (weight ratio) to obtain a light emitting layer having a thickness of 30 nm. Further, Alq3 was deposited to obtain an electron injection layer having a thickness of 30 nm. On top of this, an electrode having a film thickness of 200 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 (weight ratio) to obtain an organic EL device. Each layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This device has an emission luminance of 7000 (cd / m) at a DC voltage of 6V.2), Emission luminance at 20 V is 46000 (cd / m)2) Was obtained. In addition, emission luminance of 500 (cd / m2) Had a half life of 1000 hours when driven at a constant current.
[0115]
Comparative Example 2
An organic EL device was produced in the same manner as in Example 15 except that the comparative compound C was used in place of the compound (53). This device has a luminance of 21000 (cd / m) at a DC voltage of 20V.2)Met. In addition, emission luminance of 500 (cd / m2), The half-life when driven at a constant current was 240 hours.
[0116]
Examples 8-34And Comparative Examples 3-6
4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NPD) is vacuum-deposited on the cleaned glass plate with an ITO electrode to form a 30 nm-thick hole injection layer. Formed. Subsequently, the compound of Table 1 was vacuum-deposited and the light emitting layer with a film thickness of 30 nm was obtained. Further, a bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex was vacuum-deposited to prepare an electron injection layer having a film thickness of 30 nm, and magnesium and silver were further added at a ratio of 10: 1 (weight ratio). An electrode having a film thickness of 100 nm was formed from the alloy mixed in step 1) to obtain an organic EL device. Each layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. The light emission characteristics of this element are shown in Table 2. All of the organic EL elements of this example have a maximum light emission luminance of 35000 (cd / m2) The above high luminance characteristics were exhibited. Similarly, as a comparative example, an organic EL device was produced in the same manner as in Example 8 except that the comparative compounds A to D were formed and used. The light emission characteristics of this element are also shown in Table 2. In any case, it is clear that both the maximum light emission luminance and the maximum light emission efficiency are inferior to those of the device prepared in this example.
[0117]
[Table 2]
[0118]
Example 37
Α-NPD was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a 20 nm-thick hole injection layer. Next, the compound (9) in Table 1 and Alq3 were co-deposited at a weight ratio of 1:50 to prepare a light emitting layer having a thickness of 40 nm, and then Alq3 was evaporated to obtain an electron injection layer having a thickness of 30 nm. First, an electrode was formed by vacuum deposition of lithium fluoride (LiF) at 0.5 nm and aluminum (Al) at 200 nm to obtain an organic EL device. Each layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This device has an emission luminance of 6700 (cd / m) at a DC voltage of 7V.2), Maximum emission luminance 42100 (cd / m)2), A light emission efficiency of 3.9 (lm / W) was obtained.
[0119]
Example 38
An organic EL device was produced in the same manner as in Example 8, except that a thin film having a thickness of 30 nm was formed by depositing the compound (1) and the compound (3) in Table 1 at a weight ratio of 1: 1 as the light emitting layer. . This device has an emission luminance of 6300 (cd / m at a DC voltage of 7 V).2), Maximum emission luminance 36500 (cd / m)2), A light emission efficiency of 3.8 (lm / W) was obtained.
[0120]
Example 39
As the light emitting layer, except that a thin film having a film thickness of 30 nm obtained by depositing the compound (11) of Table 1 and bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex at a weight ratio of 1:50 is provided An organic EL device was produced in the same manner as in Example 8. This element has an emission luminance of 6500 (cd / m at a DC voltage of 7 V).2), Maximum emission luminance 38300 (cd / m)2), A light emission efficiency of 3.9 (lm / W) was obtained.
[0121]
Example 40
An organic EL device was produced in the same manner as in Example 8, except that a thin film having a thickness of 30 nm obtained by depositing the compound (16) in Table 1 and α-NPD at a weight ratio of 1:10 was provided as the light emitting layer. This element has an emission luminance of 7100 (cd / m at a DC voltage of 7 V).2) Maximum emission brightness 41200 (cd / m)2), A light emission efficiency of 4.0 (lm / W) was obtained.
[0122]
Example 41
Example 8 is provided except that a thin film having a film thickness of 30 nm obtained by depositing the compound (28) of Table 1 and 2,3,6,7,10,11-hexamethoxytriphenylene at a weight ratio of 1:10 is provided as the light emitting layer. An organic EL device was produced in the same manner as described above. This element has an emission luminance of 7200 (cd / m at a DC voltage of 7 V).2) Maximum emission brightness 42100 (cd / m)2), A light emission efficiency of 4.1 (lm / W) was obtained.
[0123]
Example 42
An organic EL device was produced in the same manner as in Example 8 except that a thin film having a thickness of 30 nm was deposited as the light emitting layer by depositing the compound (3) in Table 1 and DCJTB at a weight ratio of 100: 5. This element has an emission luminance of 5400 (cd / m at a DC voltage of 7 V).2) Maximum emission brightness 37800 (cd / m)2), A light emission efficiency of 3.2 (lm / W) was obtained.
[0124]
Example 43
Α-NPD was vacuum-deposited on the washed glass plate with the ITO electrode to obtain a hole injection layer having a thickness of 40 nm. Next, after the compound (3) in Table 1 was vacuum-deposited to form a first light-emitting layer having a thickness of 10 nm, the compound (33) in Table 1 was vacuum-deposited to form a second light-emitting layer having a thickness of 30 nm. Further, a bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex was vacuum-deposited to prepare an electron injection layer having a film thickness of 30 nm, and then magnesium and silver were added at a ratio of 10: 1 (weight ratio). An electrode having a film thickness of 100 nm was formed from the alloy mixed in step 1) to obtain an organic EL device. Each layer is 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element has an emission luminance of 6500 (cd / m at a DC voltage of 7 V).2), Maximum emission luminance 38900 (cd / m)2), A light emission efficiency of 3.8 (lm / W) was obtained.
[0125]
Example 44
4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine is vacuum-deposited on the cleaned glass plate with the ITO electrode to form a first positive electrode having a thickness of 60 nm. Next, α-NPD was vacuum-deposited to obtain a second hole injection layer having a thickness of 20 nm, and the compound (14) in Table 1 was vacuum-deposited to obtain a thickness of 10 nm. A light emitting layer was prepared, and Alq3 was vacuum deposited to form an electron injection layer having a thickness of 30 nm, on which LiF was 0.2 nm and then Al was vacuum deposited to form an electrode, An organic EL element was obtained.-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element has an emission luminance of 8600 (cd / m at a DC voltage of 7 V).2), Maximum emission luminance 43500 (cd / m)2), A light emission efficiency of 4.3 (lm / W) was obtained.
[0126]
Example 45
An organic EL device was produced in the same manner as in Example 44, except that a 30 nm-thick thin film in which the compound (24) in Table 1 and Alq3 were deposited at a weight ratio of 1: 100 was provided as the light-emitting layer. This element has an emission luminance of 32800 (cd / m) at a DC voltage of 7V.2), Emission with a luminous efficiency of 3.6 (cd / A) was obtained. In addition, emission luminance of 500 (cd / m2) Had a half life of 1200 hours when driven at a constant current.
[0127]
Comparative Example 7
An organic EL device was produced in the same manner as in Example 45 except that the comparative compound B was used instead of the compound (24). This device has an emission luminance of 13000 (cd / m at a DC voltage of 7 V).2) And emission luminance of 500 (cd / m)2), The half-life when driven at a constant current was 250 hours.
[0128]
Example 46
Example 45 except that a hole injection layer having a thickness of 20 nm of copper phthalocyanine is provided instead of 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine An organic EL device was manufactured in the same manner, and this device had an emission luminance of 30100 (cd / m at a DC voltage of 7 V).2), Light emission with a light emission efficiency of 3.9 (cd / A) was obtained. In addition, emission luminance of 500 (cd / m2), The half-life when driven at a constant current was 1500 hours.
[0129]
Comparative Example 8
An organic EL device was produced in the same manner as in Example 46 except that the comparative compound D was used instead of the compound (24). This element has an emission luminance of 15300 (cd / m at a DC voltage of 7 V).2) And emission luminance of 500 (cd / m)2), The half-life when driven at a constant current was 270 hours.
[0130]
As is clear from the above-described embodiments, the organic EL device of the present invention achieves improvement in luminous efficiency, luminous luminance, and long life, and the luminescent material, doping material, and hole injection used together. The material, the electron injection material, the sensitizer, the resin, the electrode material, and the like and the device manufacturing method are not limited.
[0131]
【The invention's effect】
Since the organic EL element produced using the material for the organic EL element of the present invention has higher luminance and longer life than conventional ones, it can be suitably used as a flat panel display such as a wall-mounted television or a flat light emitter. It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights.
[Brief description of the drawings]
1 is a CDCl of compound (3) obtained in Synthesis Example 1. FIG.ThreeIn solution11 shows an H-NMR spectrum (based on the absorption peak of tetramethylsilane).
Claims (7)
一般式[1]
一般式[2]
[ただし、一般式[1]および一般式[2]でいう置換とは、1価の脂肪族炭化水素基、1価の芳香族炭化水素基、1価の脂肪族複素環基、1価の芳香族複素環基、ハロゲン原子、シアノ基、アルコキシル基、アリールオキシ基、アルキルチオ基、アリールチオ基、アシル基、アルコキシカルボニル基、アリールオキシカルボニル基、アルキルスルホニル基、アリールスルホニル基のいずれかで置換されることである。] A material for an organic electroluminescence device, which is a monoamine compound represented by the following general formula [1].
General formula [1]
General formula [2]
[However, the substitution in the general formula [1] and the general formula [2] is a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aliphatic heterocyclic group, a monovalent Substituted with any of aromatic heterocyclic group, halogen atom, cyano group, alkoxyl group, aryloxy group, alkylthio group, arylthio group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group Is Rukoto. ]
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