JP2006523740A - 発光可能な、マトリックス材料と有機半導体との混合物、その使用、ならびに前記混合物を含む電子部品 - Google Patents
発光可能な、マトリックス材料と有機半導体との混合物、その使用、ならびに前記混合物を含む電子部品 Download PDFInfo
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- JP2006523740A JP2006523740A JP2006505097A JP2006505097A JP2006523740A JP 2006523740 A JP2006523740 A JP 2006523740A JP 2006505097 A JP2006505097 A JP 2006505097A JP 2006505097 A JP2006505097 A JP 2006505097A JP 2006523740 A JP2006523740 A JP 2006523740A
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
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- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
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- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/798—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring containing rings other than six-membered aromatic rings
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
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Abstract
Description
1.単色またはマルチカラーのディスプレイ素子(例えば、小型電卓、携帯電話ならびに他の携帯用途用)の、白色または有彩色のバックライト、
2.大表面積のディスプレイ(例えば、信号機、掲示板および他の用途)、
3.全ての色および形態での照明素子、
4.携帯用途(例えば、携帯電話、PDA、カムコーダーおよび他の用途)用の、単色またはフルカラーのパッシブマトリックス型ディスプレイ、
5.広く多様な用途(例えば、携帯電話、PDA、ラップトップ、テレビおよび他の用途)用の、フルカラー、大表面積、高解像度のアクティブマトリックス型ディスプレイ
が挙げられる。
1.例えば、特にOLEDの作動寿命は依然として低く、それゆえに現在のところ単純な用途の商業的実現のみが可能となっている。
1.キャリアプレート=基板(典型的にガラスまたはプラスチックのフィルム)。
C=Qの形の構造単位(Qは少なくとも1つの非結合性の電子対を有し、元素O、S、SeまたはNを示す)を含み、さらにガラス状の層を形成する場合がある、少なくとも1種のマトリックス材料Aと、
発光可能であり、かつ適切な励起時に発光し、原子番号が20以上の少なくとも1種の元素を含む化合物である、少なくとも1種の発光材料Bと
を含む混合物を提供する。
Xは各例で同一または異なるものであり、O、SまたはSeである;
Yは各例でNである;
R1、R2、R3は各例で同一または異なるものであり、H、CN、または直鎖、分岐鎖、もしくは環式の、アルキル基、アルコキシ基もしくはアルキルアミノ基(1個から40個の炭素原子を有し、1つまたはそれ以上の非隣接CH2基が、-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR5-または-CONR6-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置き換わっていてもよい)、または
芳香族系もしくは複素芳香族系(1個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置き換わっていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは異なる2つの環のいずれかにある複数の置換基R1および/またはR1、R2がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい;ただしR1=R2=R3≠水素)である。;
R4、R5、R6は各例で同一または異なるものであり、H、または脂肪族炭化水素基もしくは芳香族炭化水素基(1個から20個の炭素原子を有する)である。
Zは各例で同一または異なるものであり、CR1またはNである。
各例でXはOまたはSである;
各例でYはNである;
各例でZはCR1である;
R1、R2、R3は各例で同一または異なるものであり、H、または、直鎖、分枝鎖もしくは環式のアルキル基(1個から40個の炭素原子を有し、ケト官能基もしくはイミン官能基に対してα-位には水素原子がないことが好ましく、1つまたはそれ以上の非隣接CH2基が-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR5-または-CONR6-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよい)、または
芳香族系もしくは複素芳香族系(1個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは別々の環のいずれかにある複数の置換基R1および/またはR1、R2がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
R4、R5、R6は化学式(1)から(3)のもとで説明したものと各々同様である。
Arは各例で同一または異なるものであり、芳香族系もしくは複素芳香族系(2個から40個の炭素原子、好ましくは4個から30個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは別々の環のいずれかにある複数の置換基R1がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
nは各例で同一または異なるものであり、0または1である。
Eは各例で同一または異なるものであり、CまたはNである;
R7は各例で同一または異なるものであり、アルキル基、アルコシキ基もしくはアルキルアミノ基(1個から40個の炭素原子を有し、1つまたはそれ以上のCH2基が、-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR4-または-CONR4-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよい;ただし、カルボニル基に対してα-位に結合している水素原子がない)、または
芳香族基(任意に、ハロゲン、アルキル、トリフルオロメチル、ヒドロキシル、-SH、-S-アルキル、アルコキシ、ニトロ、シアノ、-COOH、-COOアルキル、-NH2、-Nアルキル、ベンジルまたはベンゾイルによって任意に置換されていてもよい)、
またはより大きな芳香族系(2個から40個の炭素原子、好ましくは4個から30個の炭素原子を有し、例えば、9,9’-スピロビフルオレン、フルオレン、トリアリールアミン等であり、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、複数の置換基R1がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
各例でA1は、X=Cの場合はR8もしくはCO-R7であり、X=Nの場合は自由電子対である;
各例でA2は、X=Cの場合はR8もしくはCO-R7であり、X=Nの場合は自由電子対である;
各例でA3は、X=Cの場合はR8もしくはCO-R7であり、X=Nの場合は自由電子対である;
R8は各例で同一または異なるものであり、H、F、Cl、Br、I、CN、NO2、または、直鎖もしくは分枝鎖もしくは環式のアルキル基(1個から40個の炭素原子を有し、1つまたはそれ以上の非隣接CH2基が-R4C=CR4-、-C≡C-、C=S、C=Se、C=NR4、-O-、-S-、-NR4-もしくは-CONR4-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよい)、または
芳香族系または複素芳香族系(1個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは別々の環のいずれかにある複数の置換基R1および/またはR1/R4がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
ただし化学式(10)については、記載した記号配下の組合せのみが許容され;R8およびR4は前記定義に従って自由に選択できる:
R7がα-水素原子を持たないアルキル基である場合、記号Z、E、A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、少なくとも1つのZがNである場合、記号E、A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、少なくとも1つのZがCR1基である(ここでR1はH以外である)場合、記号E、A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、全てのZがCHであり、かつ少なくとも1つの記号EがNである場合、記号A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、全てのZがCHであり、かつ全てのEがCである場合、記号A1、A2および/またはA3の少なくとも1つはアルキル基以外のR8基でなくてはならず、一方他の2つの基は定義に従い自由に選択できる;
R7が芳香族基であり、全てのZがCHであり、かつ全てのEがCであり、2つの記号A1およびA2を定義に従い自由に選択する(2つの記号の少なくとも1つはH以外の基である)場合、記号A3はCO-R7基(ここでR7は定義に従い自由に選択できる)である;
R7がより大きな芳香族系(例えば、フルオレン、スピロビフルオレン、トリアリールアミン等)である場合、記号Z、E、A1、A2およびA3を定義に従い自由に選択できる。
DCyは各例で同一または異なるものであり、環状基(少なくとも1つのドナー原子、好ましくは窒素または燐[それを介して環状基が金属原子と結合する]を含み、さらに1つまたはそれ以上の置換基R9を有してもよい;DCy基とCCy基は共有結合を介して互いに結合している)である;
CCyは各例で同一または異なるものであり、環状基(炭素原子[それを介して環状基が金属と結合する]を含み、1つまたはそれ以上の置換基R9をさらに有してもよい)である;
R9は各例で同一または異なるものであり、H、F、Cl、Br、I、NO2、CN、または直鎖、分枝鎖、もしくは環式の、アルキル基もしくはアルコキシ基(1個から40個の炭素原子を有し、1つまたはそれ以上の非隣接CH2基が-CR4=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR5-または-CONR6-で置換されていてもよく、1個またはそれ以上の水素原子がFで置き換わっていてもよい)、または芳香族系もしくは複素芳香族系(4個から40個の炭素原子を有し、1つまたはそれ以上の非芳香族R9基で置換されていてもよく、同一の環もしくは異なる2つの環のいずれかにある複数のR9がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
Lは各例で同一または異なるものであり、二座キレート配位子、好ましくはジケトナート配位子である;
R4、R5、R6は各例で同一または異なるものであり、H、または脂肪族もしくは芳香族の炭化水素基(1個から20個の炭素原子を有する)である。
1.マトリックス材料Aの合成:
以下の合成は、別段に述べた場合を除き、保護ガス雰囲気下、乾燥溶媒中で行った。反応物[シアン化銅(I)、塩化アセチル、N-メチルピロリジノン(NMP)]をALDRICHから購入した。2-ブロモ-9,9’-スピロビフルオレン、2,7-ジブロモ-9,9’-スピロビフルオレン(J. Peiら、J. Org. Chem. 2002, 67(14), 4924-4936)および9,9’-スピロビフルオレン-2,2’-ジカルボニル塩化物(V.A. Monteroら、Tetrahedron Lett. 1991, 32(39), 5309-5312)を文献の方法で調製した。
2-ブロモ-9,9’-スピロビフルオレン158.1g(0.4mol)とシアン化銅(I)89.6g(1mol)とのNMP1100ml懸濁液を160℃まで16時間加熱した。30℃まで冷却した後、その混合物を飽和アンモニア溶液1000mlと混合させ、さらに30分攪拌した。析出物を吸引濾過により分離し、飽和アンモニア溶液300mlで3回、水300mlで3回洗浄し、減圧乾燥した。固体をジクロロメタン1000mlに溶かした後、溶液を硫酸ナトリウムで乾燥し、シリカゲルを通して濾過し、乾ききるまで濃縮した。このようにして得られた粗生成物をジオキサン:エタノール(400ml:750ml)から一度再結晶した。減圧下80℃で結晶を乾燥させた後、81.0g(237mmol)、理論値の59.3%に相当、を得た。
2-ブロモ-9,9’-スピロビフルオレン98.8g(250ml)と1,2-ジクロロエタン6mlとのTHF1000ml溶液と、マグネシウム7.1g(290mmol)から、沸騰した状態で対応するGrignard試薬を調製した。THF300mlとトルエン1000mlとの混合物中の2-シアノ-9,9’-スピロビフルオレン85.4g(250mmol)の溶液を0−5℃でこのGrignard試薬に15分以上かけて滴下した。次に、混合物を還流しながら6時間加熱した。冷却後、10NのHCl35mlと水400mlとエタノール600mlとの混合物をゆっくりと滴下した。室温で16時間攪拌した後、固体を吸引濾過により分離し、エタノール200mlで3回洗浄した。固体をNMP(5ml/g)から4回再結晶し、続いて高真空下で昇華させた(T=385℃、p=5×10−5mbar)。HPLCによる99.9以上の純度での収量は52.1g(79mmol)であった。これは理論値の31.6%に相当する。
アンモニア溶液(エタノール中、2N)220mlを十分に攪拌しながら、ジオキサン200mlに溶解した9,9’-スピロビフルオレン-2,2’-ジカルボニル塩化物44.1g(100mmol)に滴下することで混合した。発熱反応が落ち着いた後に、この混合物をさらに2時間攪拌し、析出した固体を濾過によって分離し、水100mlとEtOH100mlとの混合物で一度、エタノール200mlで一度洗浄し、減圧下で乾燥させた。1H HMRによる99.0%以上の純度での収量は37.4g(93mmol)であった。これは理論値の93.0%に相当する。
−10℃まで冷却した、9,9’-スピロビフルオレン-2,2’-ジカルボキサミド36.2g(90mmol)のDMF800ml懸濁液を塩化チオニル52.5ml(720mmol)と温度が−5℃を超えないような速度で滴下することにより混合した。反応混合物を−10℃でさらに3時間攪拌し、その後氷2kgと水500mlとの混合物に注いだ。水解物を毎回ジクロロメタン500ml用いて2回抽出した。混合した有機相を水500mlおよび飽和塩化ナトリウム溶液で洗浄し、硫酸マグネシウムで乾燥させた。有機相の濃縮後に得られた油分は、エタノールを300ml添加した後に白色針状晶で晶析した。1H HMRによる99.0%以上の純度での収量は29.4g(80mmol)であった。これは理論値の89.3%に相当する。
実施例1Bと同様の手順。2-ブロモ-9,9’-スピロビフルオレン59.3g(150mmol)および2,2’-ジシアノスピロ-9,9’-ビフルオレン27.5g(75mmol)を使用。T=440℃で昇華。収量41.2g(41mmol)、理論値の54.8%に相当。
OLEDを以下で概要を述べる通常の方法で製造した。もちろん、個々の場合での特別な状況に応じてこれを適応させる(例えば、最適な効率および色彩を得るための層厚さの変化)必要がある。
1.ITO-被覆基板:使用する基板は好ましくは、最小水準のイオン不純物を含むか、もしくはそれを含まないITO-被覆ガラスである(例えば、Merck-BalzersもしくはAkaii製のフラットガラスが挙げられる)。しかし、他のITO-被覆透明基板(例えば、フレキシブルプラスティックフィルムもしくはラミネートが挙げられる)を使用することも可能である。ITOは最大限の導電性と高透明性とを兼ね備える必要がある。50から200nmの間のITO層の厚さが特に適切なものであるということがわかっている。ITO被覆は最大の平坦性、好ましくは2nm以下の粗さを有する必要がある。基板を最初に4%のDekonexの脱イオン水溶液で前洗浄する。その後、ITO-被覆基板を、オゾンを用いて10分間処理するか、もしくは酸素プラズマを用いて数分間処理するか、またはエキシマーランプを短時間照射するかのいずれかを行った。
ここで、様々なOLEDの結果を比較する。使用する材料、ドープの程度およびそれらの層厚さのような基本的構成は、比較をよりよくするため、これら実施例の実験で同一であった。発光層のホスト材料のみを変化させ、様々な三重項発光体を用いて実施例を行った。
PEDOT 60nm(水からスピンコートした;H.C. Starckから購入したPEDOT;ポリ[3,4-エチレンジオキシ-2,5-チオフェン])
NaphDATA 20nm(蒸着で塗布した;SynTecから購入したNaphDATA;4,4’,4’’-トリス(N-1-ナフチル-N-フェニルアミノ)-トリフェニルアミン)
S-TAD 20nm(蒸着で塗布した;WO 99/12888に従って調製したS-TAD;2,2’,7,7’-テトラキス(ビフェニルアミノ)スピロ-ビフルオレン)
発光層:
CBP 20nm(蒸着で塗布した;ALDRICHから購入したCBPであり、さらに精製し、最終的に2回以上昇華させた;4,4’-ビス(N-カルバゾルイル)ビフェニル)(比較基準)
または:
ビス(9,9’-スピロビフルオレン-2-イル)ケトン 20nm(蒸着で塗布した;実施例1に従って合成および精製した)、各場合で10%三重項発光体がドープされている
Ir(PPy)3 (蒸着で塗布した)
または:
Ir(BTP)3 (蒸着で塗布した)
または:
Ir(pig)3 (蒸着で塗布した)
または:
Ir(FMepig)3 (蒸着で塗布した)
バソクプロイン(BCP) 10nm(蒸着で塗布した;ABCRから購入したBCP、入手したまま使用した;2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン);全ての例で使用したわけではない
AlQ3 10nm(蒸着で塗布した;SynTecから購入したAlQ3;トリス(キノリノラート)アルミニウム(III))、全ての例で使用したわけではない
Ba-Al 陰極として、3nmのBa、その上に150nmのAl。
電界発光スペクトル:
OLED(ホスト材料としてCBPを有する比較基準のOLEDと、ホスト材料としてビス(9,9’-スピロビフルオレン-2-イル)ケトンを有するOLEDとの両方)はIr(PPy)3ドーパント由来の緑色発光を呈する。
CBPホスト材料を用いて製造したOLEDに対して、約25cd/Aの最大効率が典型的に得られ、かつ100cd/m2の基準照度密度には、4.8Vが必要となる。対照的に、ビス(9,9’-スピロビフルオレン-2-イル)ケトンのホスト材料を用いて製造したOLEDは30cd/A以上の最大効率を呈し、同時に100cd/m2の基準照度密度に必要な電圧は4.6Vまで落ちる。効率は、正孔障壁層(HBL)も電子輸送層(ETL)も使用せず、ドープされた発光層(EML)が陰極まで伸びる場合に特にかなり高い。35cd/A以上の最大効率が得られると、同時に100cd/m2の基準照度密度に必要な電圧は3V以下まで落ちる。特に電力効率は、ホスト材料としてビス(9,9’-スピロビフルオレン-2-イル)ケトンを使用すること(π)により、ホスト材料としてCBPを使用する場合(黒の菱形)と比べて、20%から100%増加する(図1)。正孔障壁層(HBL)も電子輸送層(ELT)もどちらも使用せず、発光層(EML)のドーピングが陰極まで及ぶ場合には、50lm/Wに至る特にかなり高い電力が得られる(□)。
ホスト材料としてCBPとビス(9,9’-スピロビフルオレン-2-イル)ケトンを用いた2つの寿命曲線(図2)(使用した両者は共に正孔障壁層と電子輸送層とを有する)をよりよい比較のために同じ図に示した。この図はcd/m2で測定した照度密度の時間に対するプロファイルを示す。寿命とは、典型的には最初の照度密度の単に50%になった後の時間のことを言う。
同様の実験を赤色の三重項発光体Ir(BTP)3を用いて行った。
OLED(ホスト材料としてCBPを有する比較標準OLEDと、ホスト材料としてビス(9,9’-スピロビフルオレン-2-イル)ケトンを有するOLEDとの両方)はIr(BTP)3に由来する赤色発光を呈する。2つのスペクトルを図3に示す。
CBPのホスト材料を用いて製造したOLEDに対して、典型的に最大効率は約8cd/Aであり、100cd/m2の基準照度密度には、6.2Vが必要である。対照的に、ホスト材料ビス(9,9’-スピロビフルオレン-2-イル)ケトンを用いて製造したOLEDは11cd/Aを上回る最大効率を呈し、同時に100cd/m2の基準照度密度に必要な電圧は5.2Vまで落ちる(図4)。
よりよい比較のために、2つの寿命曲線(図5)を同じ図に示した。この図はcd/m2の単位で測定した照度密度の時間に対するプロファイルを示す。
同様に、ビス(9,9’-スピロビフルオレン-2-イル)ケトンと共に深い赤色の三重項発光体Ir(pig)3を用いる実験、ならびにビス(9,9’-スピロビフルオレン-2-イル)ケトンと共に赤色の三重項発光体Ir(FMepig)3を用いる実験を行うことができた。
これらのOLEDは深い赤色発光と赤色発光を呈する。これらはドーパントIr(pig)3(π)およびIr(FMepig)3(黒の菱形)に由来する。2つのスペクトルを図6に示す。スペクトルから、ビス(9,9’-スピロビフルオレン-2-イル)ケトン中のIr(pig)3(π)について見積もったCIE色度座標はx=0.69;y=0.31であり、ビス(9,9’-スピロビフルオレン-2-イル)ケトン中のIr(FMpig)3(黒の菱形)について見積もったものはx=0.66;y=0.34であった。
ビス(9,9’-スピロビフルオレン-2-イル)ケトン中のIr(pig)3(π)とビス(9,9’-スピロビフルオレン-2-イル)ケトン中のIr(pig)3との両方共が、最大8cd/A(CIE色度座標x=0.69、y=0.31のIr(pig)3(π)について)および最大14cd/A(CIE色度座標x=0.66、y=0.34のIr(FMpig)3(黒の菱形)について)という非常に高い効率を呈する(図7)。両方の場合で、100cd/m2に必要な電圧は6V以下に下がった。
図8はビス(9,9’-スピロビフルオレン-2-イル)ケトンを有するIr(pig)3の、10mA/cm2の一定電流、初期輝度約800cd/m2での寿命、ならびに5mA/cm2の一定電流、初期輝度約400cd/m2での寿命を示す。この場合、初期輝度約800cd/m2では1680時間後に約10%輝度が減衰し、ならびに初期輝度約400cd/m2では1680時間後に約5%輝度が減衰した。初期輝度約800cd/m2では約500時間の寿命、ならびに初期輝度約400cd/m2では約20000時間の寿命が推定される。200cd/m2の初期輝度では、80000の寿命が見積もられる。ビス(9,9’-スピロビフルオレン-2-イル)ケトン中のIr(FMpig)3はそれに匹敵する寿命を示す。
Claims (21)
- C=Qの形の構造単位(Qは少なくとも1つの非結合性電子対を有し、元素O、S、SeもしくはNを表す)を含む、少なくとも1種のマトリックス材料Aと、
発光可能であり、かつ適切な励起時に発光し、原子番号が20以上の少なくとも1種の元素を含む化合物である、少なくとも1種の発光材料Bと
を含む混合物。 - 前記マトリックス材料Aがガラス状の層を形成できることを特徴とする請求項1記載の混合物。
- 前記マトリックス材料Aは70℃以上のガラス転移温度Tg(純粋物として測定)を持つことを特徴とする請求項1または2記載の混合物。
- 使用する前記マトリックス材料Aは、化学式(1)、化学式(2)および/または化学式(3)の少なくとも1種の化合物であることを特徴とする請求項1から3のいずれか1項もしくはそれ以上の項記載の混合物。
Xは各例で同一または異なるものであり、O、SまたはSeである;
Yは各例でNである;
R1、R2、R3は各例で同一または異なるものであり、H、CN、または直鎖、分枝鎖、もしくは環式の、アルキル基、アルコキシ基もしくはアルキルアミノ基(1個から40個の炭素原子を有し、1つまたはそれ以上の非隣接CH2基が-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR5-または-CONR6-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置き換わっていてもよい)、または
芳香族系もしくは複素芳香族系(1個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置き換わっていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは異なる2つの環のいずれかにある複数の置換基R1および/またはR1、R2がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい;ただしR1=R2=R3≠水素)である。;
R4、R5、R6は各例で同一または異なるものであり、H、または脂肪族炭化水素基もしくは芳香族炭化水素基(1個から20個の炭素原子を有する)である。 - 使用する前記マトリックス材料Aは、化学式(1)から(9)の少なくとも1種の化合物であることを特徴とする請求項4または請求項5記載の混合物。
ここで、使用する記号は:
Xは各例で同一または異なるものであり、OまたはSである、
各例でYはNである;
各例でZはCR1である;
R1、R2、R3は各例で同一または異なるものであり、H、または、直鎖、分枝鎖もしくは環式のアルキル基(1個から40個の炭素原子を有し、ケト官能基もしくはイミン官能基に対してα-位には水素原子がなく、1つまたはそれ以上の非隣接CH2基が-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR5-または-CONR6-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよい)、または
芳香族系もしくは複素芳香族系(1個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは別々の環のいずれかにある複数の置換基R1および/またはR1、R2がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
R4、R5、R6は請求項4のもとで説明したものと各々同様である。 - 使用する前記マトリックス材料Aが化学式(10)から(15)の少なくとも1種の化合物を含むことを特徴とする請求項1から3のいずれか1項もしくはそれ以上の項記載の混合物。
Arは各例で同一または異なるものであり、芳香族系もしくは複素芳香族系(2個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは別々の環のいずれかにある複数の置換基R1がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
nは各例で同一または異なるものであり、0または1である。 - 使用する前記発光体Bは、適切な励起時に発光し、原子番号が38以上84以下の少なくとも1種の原子を含む少なくとも1種の化合物であることを特徴とする請求項1から7のいずれか1項もしくはそれ以上の項記載の混合物。
- 使用する前記発光体Bは、適切な励起時に発光し、原子番号が56以上80以下の少なくとも1種の原子を含む少なくとも1種の化合物であることを特徴とする請求項8記載の混合物。
- 使用する前記発光体Bは、適切な励起時に発光し、モリブデン、タングステン、レニウム、ルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金、銀、金またはユーロピウムの群からの少なくとも1種の原子を含む少なくとも1種の化合物であることを特徴とする請求項9記載の混合物。
- 使用する前記発光体Bは化学式(16)から(19)の少なくとも1種の化合物であることを特徴とする請求項1から10のいずれか1項もしくはそれ以上の項記載の混合物。
DCyは各例で同一または異なるものであり、環状基(少なくとも1つのドナー原子[それを介して前記環状基が金属原子と結合する]を含み、さらに1つまたはそれ以上の置換基R9を有してもよい;前記DCy基とCCy基は共有結合を介して互いに結合している)である;
CCyは各例で同一または異なるものであり、環状基(炭素原子[それを介して前記環状基が金属と結合している]を含み、さらに1つまたはそれ以上の置換基R9を有してもよい)である;
R9は各例で同一または異なるものであり、H、F、Cl、Br、I、NO2、CN、または直鎖、分枝鎖、もしくは環式の、アルキル基もしくはアルコキシ基(1個から40個の炭素原子を有し、1つまたはそれ以上の非隣接CH2基が-CR4=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR5-または-CONR6-で置換されていてもよく、1個またはそれ以上の水素原子がFで置き換わっていてもよい)、または芳香族系もしくは複素芳香族系(4個から40個の炭素原子を有し、1つまたはそれ以上の非芳香族R9基で置換されていてもよく;同一の環もしくは異なる2つの環のいずれかにある複数のR9がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
Lは各例で同一または異なるものであり、二座キレート配位子である;
R4、R5、R6は各例で同一または異なるものであり、H、または脂肪族もしくは芳香族の炭化水素基(1個から20個の炭素原子を有する)である。 - 前記マトリックス材料は1種もしくはそれ以上のポリマーもしくはデンドリマーを含むことを特徴とする請求項1から11のいずれか1項もしくはそれ以上の項記載の混合物。
- 前記ポリマーは共役系、半共役系もしくは非共役系であることを特徴とする請求項12記載の混合物。
- 前記ポリマーは、ポリフルオレン、ポリ-スピロ-ビフルオレン、ポリ-パラ-フェニレン、ポリカルバゾール、ポリビニルカルバゾール、ポリ-チオフェンの群から、もしくは複数のこれらの単位を有するコポリマーから選択されることを特徴とする請求項12および/または13記載の混合物。
- 発光体Bとマトリックス材料Aとの前記混合物全体に対して、発光体Bを1から99重量%の間で含むことを特徴とする請求項1から14のいずれか1項もしくはそれ以上の項記載の混合物。
- 化学式(10a)から(15)の化合物。
Eは各例で同一または異なるものであり、CまたはNである;
R7は各例で同一または異なるものであり、アルキル基、アルコシキ基もしくはアルキルアミノ基(1個から40個の炭素原子を有し、1つまたはそれ以上のCH2基が-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-O-、-S-、-NR4-または-CONR4-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、ただしカルボニル基についてのα-位に結合している水素原子がない)、または
芳香族基(任意に、ハロゲン、アルキル、トリフルオロメチル、ヒドロキシル、-SH、-S-アルキル、アルコキシ、ニトロ、シアノ、-COOH、-COOアルキル、-NH2、-Nアルキル、ベンジルまたはベンゾイルによって任意に置換されていてもよい)、または
より大きな芳香族系(2個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、複数の置換基R1がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
各例でA1は、X=Cの場合はR8もしくはCO-R7であり、X=Nの場合は自由電子対である;
各例でA2は、X=Cの場合はR8もしくはCO-R7であり、X=Nの場合は自由電子対である;
各例でA3は、X=Cの場合はR8もしくはCO-R7であり、X=Nの場合は自由電子対である;
R8は各例で同一または異なるものであり、H、F、Cl、Br、I、CN、NO2、または、直鎖もしくは分枝鎖もしくは環式のアルキル基(1個から40個の炭素原子を有し、1つまたはそれ以上の非隣接CH2基が-R4C=CR4-、-C≡C-、C=S、C=Se、C=NR4、-O-、-S-、-NR4-もしくは-CONR4-で置換されていてもよく、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよい)、または
芳香族系または複素芳香族系(1個から40個の炭素原子を有し、1個またはそれ以上の水素原子がF、Cl、Br、Iで置換されていてもよく、1つまたはそれ以上の非芳香族R1基で置換されていてもよく、同一の環もしくは別々の環のいずれかにある複数の置換基R1および/またはR1/R4がともに結合し、別の、単環式もしくは多環式の、脂肪族環構造もしくは芳香族環構造をさらに形成してもよい)である;
ただし化学式(10)については、記載した記号については以下の組合せのみが許容され;R8およびR4は前記定義に従って自由に選択できる:
R7がα-水素原子を持たないアルキル基である場合、記号Z、E、A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、少なくとも1つのZがNである場合、記号E、A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、少なくとも1つのZがCR1基である(ここでR1はH以外である)場合、記号E、A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、全てのZがCHであり、かつ少なくとも1つの記号EがNである場合、記号A1、A2およびA3を定義に従い自由に選択できる;
R7が芳香族基であり、全てのZがCHであり、かつ全てのEがCである場合、記号A1、A2および/またはA3の少なくとも1つはアルキル基以外のR8基でなくてはならず、一方他の2つの基は定義に従い自由に選択できる;
R7が芳香族基であり、全てのZがCHであり、かつ全てのEがCであり、2つの記号A1およびA2を定義に従い自由に選択する(2つの記号の少なくとも1つはH以外の基である)場合、記号A3はCO-R7基(ここでR7は定義に従い自由に選択できる)である;
R7がより大きな芳香族系(例えば、フルオレン、スピロビフルオレン、トリアリールアミン等)である場合、記号Z、E、A1、A2およびA3を定義に従い自由に選択できる。 - 請求項1から15のいずれか1項またはそれ以上の項記載の少なくとも1種の混合物および/または請求項16記載の少なくとも1種の化合物を含む電子部品。
- 有機発光ダイオード(OLED)、有機集積回路(O-IC)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(OTFT)、有機太陽電池(O-SC)または有機レーザーダイオード(O-レーザー)であることを特徴とする請求項17記載の電子部品。
- 前記電気部品は、少なくとも1層の正孔注入層および/または少なくとも1層の正孔輸送層および/または少なくとも1層の正孔障壁層および/または少なくとも1層の電子輸送層および/または少なくとも1層の電子注入層および/または他の層を有し、かつ発光層に請求項1から15のいずれか1項またはそれ以上の項記載の少なくとも1種の本発明の混合物を含む有機発光ダイオード(OLED)であることを特徴とする請求項17および/または18記載の電気部品。
- 別の正孔障壁層を使用せずに、請求項1から15のいずれか1項またはそれ以上の項記載の混合物が電子輸送層に直接隣接することを特徴とする請求項19記載の電子部品。
- 別の正孔障壁層および別の電子輸送層を使用せずに、請求項1から15のいずれか1項またはそれ以上の項記載の混合物が電子輸送層または陰極に直接隣接することを特徴とする請求項19記載の電子部品。
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PCT/EP2004/003861 WO2004093207A2 (de) | 2003-04-15 | 2004-04-13 | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien, deren verwendung und elektronikbauteile enthaltend diese mischungen |
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Also Published As
Publication number | Publication date |
---|---|
US7345301B2 (en) | 2008-03-18 |
EP1717291A3 (de) | 2007-03-21 |
US20060208221A1 (en) | 2006-09-21 |
EP1618170A2 (de) | 2006-01-25 |
WO2004093207A3 (de) | 2005-06-09 |
KR101162933B1 (ko) | 2012-07-05 |
JP2011201878A (ja) | 2011-10-13 |
JP5318347B2 (ja) | 2013-10-16 |
JP5362759B2 (ja) | 2013-12-11 |
KR20060003020A (ko) | 2006-01-09 |
EP2281861A2 (de) | 2011-02-09 |
EP2281861A3 (de) | 2012-03-28 |
WO2004093207A2 (de) | 2004-10-28 |
EP1717291A2 (de) | 2006-11-02 |
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