JPWO2007004380A1 - 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 - Google Patents
有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 Download PDFInfo
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- JPWO2007004380A1 JPWO2007004380A1 JP2007523378A JP2007523378A JPWO2007004380A1 JP WO2007004380 A1 JPWO2007004380 A1 JP WO2007004380A1 JP 2007523378 A JP2007523378 A JP 2007523378A JP 2007523378 A JP2007523378 A JP 2007523378A JP WO2007004380 A1 JPWO2007004380 A1 JP WO2007004380A1
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- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000767 polyaniline 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
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- VEPOUCHBIJXQFI-UHFFFAOYSA-N pyrazabole Chemical compound [B-]1N2C=CC=[N+]2[B-][N+]2=CC=CN12 VEPOUCHBIJXQFI-UHFFFAOYSA-N 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
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical group [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
Classifications
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- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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Abstract
Description
Youn.0g、Tetsuo Tsutsui等は、やはり、The 10th International Workshop on Inorganic and Organic Electroluminescence(EL’00、浜松)において、ドーパントとして、トリス(2−(p−トリル)ピリジン)イリジウム(Ir(ptpy)3),トリス(ベンゾ[h]キノリン)イリジウム(Ir(bzq)3)等を用いた検討を行っている(なおこれらの金属錯体は一般にオルトメタル化イリジウム錯体と呼ばれている。)。
(2) 下記一般式(1)を部分構造として有する金属錯体であることを特徴とする前記(1)に記載の有機エレクトロルミネッセンス素子材料。
(3) 下記一般式(2)を部分構造として有する金属錯体であることを特徴とする前記(1)に記載の有機エレクトロルミネッセンス素子材料。
(4) 下記一般式(3)を部分構造として有する金属錯体であることを特徴とする前記(1)に記載の有機エレクトロルミネッセンス素子材料。
(5) 下記一般式(4)を部分構造として有する金属錯体であることを特徴とする前記(1)に記載の有機エレクトロルミネッセンス素子材料。
(6) 前記一般式(A)のMaが、イリジウムまたは白金であることを特徴とする前記(1)に記載の有機エレクトロルミネッセンス素子材料。
3 画素
5 走査線
6 データ線
7 電源ライン
10 有機EL素子
11 スイッチングトランジスタ
12 駆動トランジスタ
13 コンデンサ
A 表示部
B 制御部
107 透明電極付きガラス基板
106 有機EL層
105 陰極
102 ガラスカバー
108 窒素ガス
109 捕水剤
本発明の有機EL素子材料に係る金属錯体について説明する。
本発明に係る金属錯体は、上記一般式(A)及び一般式(1)〜(4)で表される部分構造、または、該一般式(A)及び一般式(1)〜(4)の各々の互変異性体で表される部分構造の少なくともひとつを有する(具体的には、配位構造として有する)ことが特徴であり、該金属錯体全てが、前記一般式(A)及び一般式(1)〜(4)で表される部分構造、または、該一般式(A)及び一般式(1)〜(4)の各々の互変異性体で表される部分構造のみで構成されていてもよく、従来公知の金属錯体形成に用いられる、いわゆる、配位子として当該業者が周知の配位子(配位化合物ともいう)を必要に応じて配位子として有していてもよい。
本発明に係る、一般式(A)及び一般式(1)〜(4)で表される部分構造の少なくともひとつを有する(具体的には、配位構造として有することである)金属錯体の形成に用いられる金属としては、元素周期表の8族〜10族の遷移金属元素(単に遷移金属ともいう)が用いられるが、中でも、イリジウム、白金が好ましい遷移金属元素として挙げられる。
一般式(A)において、Xa、Xb、Xc、Xd、Xe、Xfは各々炭素原子、CRa、窒素原子、NRb、酸素原子、または、窒素原子を表し、少なくとも一つはCRaである。
一般式(1)において、X01、X02、X03、X04、X05、X06の少なくとも一つはCR01である。
一般式(2)において、X11、X12、X13、X14、X15、X16で各々表される、CR11またはNR12のR11、R12で各々表される置換基は、一般式(1)において、X01、X02、X03、X04、X05、X06で各々表される、CR01またはNR02のR01、R02で各々表される置換基と同義である。
一般式(3)において、X21、X22、X23、X24、X25、X26で各々表される、CR21またはNR22のR21、R22で各々表される置換基は、一般式(1)において、X01、X02、X03、X04、X05、X06で各々表される、CR01またはNR02のR01、R02で各々表される置換基と同義である。
一般式(4)において、X31、X32、X33、X34、X35、X36で各々表される、CR31または−NR32のR31、R32で各々表される置換基は、一般式(1)において、X01、X02、X03、X04、X05、X06で各々表される、CR01またはNR02のR01、R02で各々表される置換基と同義である。
化合物4−2の合成過程において、中間体として用いられる、化合物(A)、化合物(B)、化合物(C)及び化合物(D)を以下に示す。
Chemistry,第41巻,第12号,3055〜3066ページ(2002年)、New Journal of Chemistry.,第26巻,1171ページ(2002年)、European Journal of Organic Chemistry., 第4巻、695〜709(2004年)、さらに、これらの文献中に記載の参考文献等の方法を参照して合成可能である。
本発明の有機EL素子材料を用いて本発明の有機EL素子を作製する場合、有機EL素子の構成層(詳細は後述する)の中で、発光層または電子阻止層に本発明の有機EL素子材料を用いることが好ましい。また、発光層中では上記のように、発光ドーパントとして好ましく用いられる。
発光層中の主成分であるホスト化合物である発光ホストに対する発光ドーパントとの混合比は好ましくは質量で0.1質量%〜30質量%未満の範囲に調整することである。
本発明に用いられる発光ホスト(ホスト化合物)とは、発光層に含有される化合物のうちで室温(25℃)においてリン光発光のリン光量子収率が、0.01未満の化合物を表す。
本発明の有機EL素子の構成層について説明する。
(i)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極
(ii)陽極/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
(iii)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
(iv)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
(v)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vi)陽極/陽極バッファー層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vii)陽極/陽極バッファー層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
《阻止層(電子阻止層、正孔阻止層)》
本発明に係る阻止層(例えば、電子阻止層、正孔阻止層)について説明する。
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。
一方、電子阻止層とは広い意味では正孔輸送層の機能を有し、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料からなり、正孔を輸送しつつ電子を阻止することで電子と正孔の再結合確率を向上させることができる。また、後述する正孔輸送層の構成を必要に応じて電子阻止層として用いることができる。
正孔輸送層とは正孔を輸送する機能を有する材料を含み、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層もしくは複数層設けることができる。
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層、正孔阻止層も電子輸送層に含まれる。電子輸送層は、単層もしくは複数層を設けることができる。
注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記のごとく陽極と発光層または正孔輸送層の間、及び、陰極と発光層または電子輸送層との間に存在させてもよい。
本発明の有機EL素子に係る陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極は、これらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また、陽極としてのシート抵抗は数百Ω/□以下が好ましい。さらに膜厚は材料にもよるが、通常10〜1000nm、好ましくは10〜200nmの範囲で選ばれる。
一方、本発明に係る陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えばマグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極は、これらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm〜1000nm、好ましくは50nm〜200nmの範囲で選ばれる。なお、発光を透過させるため、有機EL素子の陽極または陰極のいずれか一方が、透明または半透明であれば発光輝度が向上し好都合である。
本発明の有機EL素子に係る基体としては、ガラス、プラスチック等の種類には特に限定はなく、また、透明のものであれば特に制限はないが、好ましく用いられる基板としては例えばガラス、石英、光透過性樹脂フィルムを挙げることができる。特に好ましい基体は、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。
本発明の有機EL素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極からなる有機EL素子の作製法について説明する。
本発明の表示装置について説明する。本発明の表示装置は上記有機EL素子を有する。
本発明の照明装置について説明する。本発明の照明装置装置は上記有機EL素子を有する。
《有機EL素子1−1の作製》
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、5つのタンタル製抵抗加熱ボートに、α−NPD、CA−1、Ir−12、BCP、Alq3をそれぞれ入れ、真空蒸着装置(第1真空槽)に取付けた。
有機EL素子1−1の作製において、表1に記載のように発光ホスト及び発光ドーパントを変更した以外は同様にして、有機EL素子1−2〜1−16を作製した。
得られた有機EL素子1−1〜1−16を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図5、図6に示すような照明装置を形成して評価した。
有機EL素子を室温(約23〜25℃)、2.5mA/cm2の定電流条件下による点灯を行い、点灯開始直後の発光輝度(L)[cd/m2]を測定することにより、外部取り出し量子効率(η)を算出した。ここで、発光輝度の測定は、CS−1000(ミノルタ製)を用いた。外部取り出し量子効率は、有機EL素子1−1を100とする相対値で表した。
有機EL素子を室温下、2.5mA/cm2の定電流条件下による連続点灯を行い、初期輝度の半分の輝度になるのに要する時間(τ1/2)を測定した。発光寿命は、有機EL素子1−1を100と設定する相対値で表した。
《有機EL素子2−1の作製》
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
有機EL素子2−1の作製において、表2に記載のように発光ホスト及び発光ドーパントを変更した以外は同様にして、有機EL素子2−2〜2−15を作製した。
得られた有機EL素子2−1〜2−15を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図5、図6に示すような照明装置を形成して評価した。
有機EL素子2−1〜2−15を室温下、2.5mA/cm2の定電流条件下による連続点灯を行い、初期輝度の90%の輝度になるのに要する時間(τ1/9)を測定した。なお、発光寿命は、有機EL素子2−1を100とする相対値で表した。
《有機EL素子3−1の作製》
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
有機EL素子3−1の作製において、表3に記載のように発光ホスト、発光ドーパント及び正孔阻止材料を用いた以外は同様にして、有機EL素子3−2〜3−18を各々作製した。
得られた有機EL素子3−1〜3−18を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図5、図6に示すような照明装置を形成して評価した。
《有機EL素子4−1の作製》
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、タンタル製抵抗加熱ボートに、α−NPD、比較4、CA−1、Ir−1、BCP、Alq3をそれぞれ入れ、真空蒸着装置(第1真空槽)に取付けた。
有機EL素子1−1の作製において、表4に記載のように電子阻止材料を変更した以外は同様にして、有機EL素子4−2〜4−9を作製した。
得られた有機EL素子4−1〜4−9を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図5、図6に示すような照明装置を形成して評価した。
《有機EL素子5−1の作製》
25mm×25mm×0.5mmのガラス支持基板上に直流電源を用い、スパッタ法にてインジウム錫酸化物(ITO、インジウム/錫=95/5モル比)の陽極を形成した(厚み200nm)。この陽極の表面抵抗は10Ω/□であった。これにポリビニルカルバゾ−ル(正孔輸送性バインダーポリマー)/Ir−13(青発光性オルトメタル化錯体)/2−(4−ビフェニリル)−5−(4−t−ブチルフェニル)−1,3,4−オキサジアゾ−ル(電子輸送材)=200/2/50質量比を溶解したジクロロエタン溶液をスピンコ−タ−で塗布し、100nmの発光層を得た。この有機化合物層の上にパタ−ニングしたマスク(発光面積が5mm×5mmとなるマスク)を設置し、蒸着装置内で陰極バッファー層としてフッ化リチウム0.5nm及び陰極としてアルミニウム150nmを蒸着して陰極を設けて、青色発光の有機EL素子5−1を作製した。
有機EL素子5−1の作製において、表5に記載のように発光ドーパントを変更した以外は同様にして、有機EL素子5−2〜5−5を作製した。
得られた有機EL素子5−1〜5−5を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図5、図6に示すような照明装置を形成して評価した。
東洋テクニカ製ソ−スメジャ−ユニット2400型を用いて、直流電圧を有機EL素子に印加して発光させ、10Vの直流電圧を印加した時の発光輝度(cd/m2)と2.5mA/cm2の電流を通じた時の発光効率(lm/W)を測定した。
《フルカラー表示装置の作製》
(青色発光素子の作製)
実施例1の有機EL素子1−5を青色発光素子として用いた。
実施例4の有機EL素子4−7を緑色発光素子として用いた。
実施例2の有機EL素子2−1において、Ir−13をIr−9に変更した以外は同様にして、赤色発光素子を作製し、これを赤色発光素子として用いた。
《白色発光素子及び白色照明装置の作製》
実施例1の透明電極基板の電極を20mm×20mmにパターニングし、その上に実施例1と同様に正孔注入/輸送層としてα−NPDを25nmの厚さで成膜し、さらに、CA−1の入った前記加熱ボートと本発明に係る化合物1−11の入ったボート及びIr−9の入ったボートをそれぞれ独立に通電して、発光ホストであるCA−1と発光ドーパントである本発明に係る化合物1−11及びIr−9の蒸着速度が100:5:0.6になるように調節し膜厚30nmの厚さになるように蒸着し、発光層を設けた。
Claims (17)
- 下記一般式(A)を部分構造として有する金属錯体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材料。
〔式中、Xa、Xb、Xc、Xd、Xe、Xfは各々炭素原子、CRa、窒素原子、NRb、酸素原子、硫黄原子を表すが、その少なくとも一つはCRaである。Ya、Yb、Ycは各々炭素原子、または、窒素原子を表し、Ydは窒素原子を表すが、YaとYbが同じ原子である場合には、Ycは窒素原子になることはない。Ra、Rbは水素原子、または、置換基を表すが、Raの少なくとも一つは芳香族炭化水素環基、または、芳香族複素環基を表す。Maは元素周期表における8族〜10族の金属を表す。環Z1、環Z2は各々5員単環を表し、環Z1、環Z2を各々形成する結合は、各々単結合、または、二重結合を表し、各々単環である。〕 - 下記一般式(1)を部分構造として有する金属錯体であることを特徴とする請求の範囲第1項に記載の有機エレクトロルミネッセンス素子材料。
〔式中、X01、X02、X03、X04、X05、X06は、各々CR01、窒素原子、NR02、酸素原子または硫黄原子を表すが、少なくとも一つはCR01である。Y01、Y02は、各々炭素原子または窒素原子を表す。R01、R02は、各々水素原子または置換基を表すが、R01の少なくとも一つは芳香族炭化水素環基または芳香族複素環基を表す。M01は、元素周期表における8族〜10族の遷移金属元素を表す。環A、環Bは、各々5員単環を表し、該環A、該環Bを各々形成する結合は、単結合または二重結合を表す。〕 - 下記一般式(2)を部分構造として有する金属錯体であることを特徴とする請求の範囲第1項に記載の有機エレクトロルミネッセンス素子材料。
〔式中、X11、X12、X13、X14、X15、X16は、各々CR11、窒素原子、NR12、酸素原子または硫黄原子を表すが、少なくとも一つはCR11である。R11、R12は、各々水素原子または置換基を表すが、R11の少なくとも一つは芳香族炭化水素環基または芳香族複素環基を表す。M11は、元素周期表における8族〜10族の遷移金属元素を表す。環C、環Dは、各々5員単環を表し、該環C、該環Dを形成する結合は、各々単結合または二重結合を表す。〕 - 下記一般式(3)を部分構造として有する金属錯体であることを特徴とする請求の範囲第1項に記載の有機エレクトロルミネッセンス素子材料。
〔式中、X21、X22、X23、X24、X25、X26は、各々CR21、窒素原子、NR22、酸素原子または硫黄原子を表すが、その少なくとも一つはCR21である。R21、R22は、各々水素原子または置換基を表すが、R21の少なくとも一つは芳香族炭化水素環基または芳香族複素環基を表す。M21は、元素周期表における8族〜10族の遷移金属元素を表す。環E、環Fは、各々5員単環を表し、該環E、該環Fを形成する結合は、各々単結合または二重結合を表す。〕 - 下記一般式(4)を部分構造として有する金属錯体であることを特徴とする請求の範囲第1項に記載の有機エレクトロルミネッセンス素子材料。
〔式中、X31、X32、X33、X34、X35、X36は、各々CR31、窒素原子、NR32、酸素原子または硫黄原子を表すが、少なくとも一つはCR31である。X37、X38は、各々炭素原子または窒素原子を表す。R31、R32は、各々水素原子または置換基を表すが、R31の少なくとも一つは芳香族炭化水素環基または芳香族複素環基を表す。M31は、元素周期表における8族〜10族の遷移金属元素を表す。環G、環Hは、各々5員単環を表し、該環G、該環Hを形成する結合は、各々単結合または二重結合を表す。〕 - 前記一般式(A)のMaが、イリジウムまたは白金であることを特徴とする請求の範囲第1項に記載の有機エレクトロルミネッセンス素子材料。
- 前記一般式(1)のM01が、イリジウムまたは白金であることを特徴とする請求の範囲第2項に記載の有機エレクトロルミネッセンス素子材料。
- 前記一般式(2)のM11が、イリジウムまたは白金であることを特徴とする請求の範囲第3項に記載の有機エレクトロルミネッセンス素子材料。
- 前記一般式(3)のM21が、イリジウムまたは白金であることを特徴とする請求の範囲第4項に記載の有機エレクトロルミネッセンス素子材料。
- 前記一般式(4)のM31が、イリジウムまたは白金であることを特徴とする請求の範囲第5項に記載の有機エレクトロルミネッセンス素子材料。
- 請求の範囲第1項〜10項のいずれか1項に記載の有機エレクトロルミネッセンス素子材料を含有す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。
- 構成層として発光層を有し、該発光層が請求の範囲第1項〜10項のいずれか1項に記載の有機エレクトロルミネッセンス素子材料を含有す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。
- 構成層として電子阻止層を有し、該電子阻止層が請求の範囲第1項〜10項のいずれか1項に記載の有機エレクトロルミネッセンス素子材料を含有す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。
- 構成層として発光層を有し、該発光層が、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素原子で置換されている環構造を有する誘導体を含有することを特徴とする請求の範囲第11項〜13項のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 構成層として正孔阻止層を有し、該正孔阻止層が、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素原子で置換されている環構造を有する誘導体を含有することを特徴とする請求の範囲第11項〜14項のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 請求の範囲第11項〜15項のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする表示装置。
- 請求の範囲第11項〜15項のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする照明装置。
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- 2006-06-06 US US11/994,046 patent/US20090039771A1/en not_active Abandoned
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CN113185557A (zh) * | 2021-05-12 | 2021-07-30 | 南京工业大学 | 一类铱配合物有机光伏材料及其制备方法与应用 |
CN113185557B (zh) * | 2021-05-12 | 2022-08-30 | 南京工业大学 | 一类铱配合物有机光伏材料及其制备方法与应用 |
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US9379337B2 (en) | 2016-06-28 |
US20150295191A1 (en) | 2015-10-15 |
US20090039771A1 (en) | 2009-02-12 |
US20130338362A1 (en) | 2013-12-19 |
WO2007004380A1 (ja) | 2007-01-11 |
US9099659B2 (en) | 2015-08-04 |
JP5076891B2 (ja) | 2012-11-21 |
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