JP2015520166A - 縮合複素環式芳香族環を含む金属錯体 - Google Patents
縮合複素環式芳香族環を含む金属錯体 Download PDFInfo
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- JP2015520166A JP2015520166A JP2015513034A JP2015513034A JP2015520166A JP 2015520166 A JP2015520166 A JP 2015520166A JP 2015513034 A JP2015513034 A JP 2015513034A JP 2015513034 A JP2015513034 A JP 2015513034A JP 2015520166 A JP2015520166 A JP 2015520166A
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- UPNFMHMMXOKBOJ-UHFFFAOYSA-N zinc iridium(3+) oxygen(2-) Chemical compound [Ir+3].[O-2].[Zn+2] UPNFMHMMXOKBOJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
Aは、任意の芳香族もしくは複素環式芳香族構造か、または任意の芳香族もしくは複素環式芳香族ポリ環式構造であることができ;
Bは、任意のモノ環式複素環式芳香族構造であり;
Cは、式(2)中で記号#で示される位置を介して任意の位置で環Dに縮合する式(2)を有する化学構造であり;、
aは、0、1または2であり;
bは、0、1または2であり;
cは、0、1、2、3または4であり;
Mは、イリジウム、ロジウム、白金およびパラジウム、好ましくは、イリジウム、白金およびパラジウム、特に、好ましくは、イリジウムおよび白金、非常に、特に、好ましくは、イリジウムより成る群から選ばれ;
nは、イリジウムもしくはロジウムであるMに対して、2であり、nは、白金もしくはパラジウムであるMに対して、1であり;環A、B、CおよびDを含む二個のリガンドは、互いに同一であるか異なることができ、好ましくは、同一であり;
R1は、出現毎に互いに同一であるか異なり、H、D、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(R2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(夫々1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S、CONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族環構造もしくは複素環式芳香族環構造、1以上の基2で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基または1以上の基2で置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または2個以上のこれらの基の組み合わせから選ばれ、ここで、2個以上の基R1は、モノあるいはポリ環式の脂肪族、芳香族および/またはベンゾ縮合環構造をたがいに形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(R3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(夫々1以上の基R3により置換されてよく、1以上の隣接しないCH2基は、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S、CONR3で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R3により置換されてよい5〜60個の芳香族環原子を有する芳香族環構造もしくは複素環式芳香族環構造、1以上の基3で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基または1以上の基3で置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または2個以上のこれらの基の組み合わせから選ばれ;ここで、2個以上の隣接する基R2は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造をたがいに形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基から選ばれ、さらに、1以上のH原子は、Fで置き代えられてよく;ここで、2個以上の置換基R3は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造をたがいに形成してよく;
Qは、出現毎に同一であるか異なり、R1C=CR1、R1C=N、O、S、SO2、SiR1 2、SeまたはNR1、好ましくは、R1C=CR1、SまたはNR1、特に、好ましくは、R1C=CR1またはS、非常に、特に、好ましくは、R1C=CR1から選ばれ;
X1およびX2は、出現毎に同一であるか異なり、CR1またはNから選ばれ、ここで、少なくとも一つのX1およびX2は、Nであり;
Vは、出現毎に同一であるか異なり、NR1、O、S、SO2、SiR1 2、BR1またはSe、好ましくは、NR1、O、S、特に、好ましくは、SまたはO、に、特に、好ましくは、Oから選ばれる。
リガンドL1〜L44の合成
例1による(dbfqH)の調製に類似して、スズキカップリング反応を、化合物L1〜L44のような種々の類似の化合物を調製するために使用することができる。通常の調製方法を以下に示す:
1,2-ジメトキシエタン(50mL)中のハロゲン化合物(10.5ミリモル;エダクト2)とPd(PPh3)4(0.35ミリモル、1/30当量)との混合物に対して、脱気エタノール(50mL)中のボロン酸の溶液(11ミリモル、エダクト1)を添加し、続いて、2.6Mの水酸化ナトリウム水溶液(50mL)を添加する。次いで、その混合物を不活性雰囲気下、20時間、還流下で加熱する。冷却後、酢酸エチル(50mL)と水(100mL)を添加し、不溶性材料を濾過により取り除く。濾過物を標準的な水性後処理で処理する。溶媒を取り除き、残留物をカラムクロマトグラフィーにより精製する。クロロホルム/ヘキサンからの再結晶化は、化合物の白色の結晶性固形物を約65〜90%の収率で生じる。
2-(3-(トリフルオロメチル)-1H-1,2,4-トリアゾール-5-イル)ピリジン(fptzH)と2-(3-(ペルフルオロブチル)-1H-1,2,4-トリアゾール-5-イル)ピリジン(hptzH)の合成
50mLのTHF中のエチルトリフルオロアセテート(3.52g、24.77ミリモル)とヒドラジン一水和物(1.14mL、23.50ミリモル)の溶液を1時間還流する。室温まで冷却したとき、この溶液に2-ピリジンカルボキシイミドアミドクロリド(3.99g、25.2ミリモル)とNaOH(1.01g,25.32ミリモル)とを添加する。混合物を6時間還流し、室温まで冷却する。その後、白色の固形物が酢酸エチルによる抽出で得られる。生成物をカラムクロマトグラフィーを介して精製し、56%の収率(2.82g、13.16ミリモル)で得られる。
50mLのTHF中のノナフルオロペンタン酸エチルエステル(4.35g、14.9ミリモル)とヒドラジン一水和物(0.73mL、15.8ミリモル)の溶液を1時間還流する。室温まで冷却したとき、溶液に2-ピリジンカルボキシイミドアミドヒドロクロリド(2.49g、15.7ミリモル)とNaOH(0.63g,15.8ミリモル)とを添加する。混合物を6時間還流し、室温まで冷却する。反応が終了した後、白色の固形物が酢酸エチルによる抽出で得られる。生成物をカラムクロマトグラフィーを介して精製し、62%の収率(3.36g、9.23ミリモル)で得られる。
さらなるクロロブリッジダイマーの合成
例7による(dbfq)2Ir(μ-Cl)2Ir(dbfq)2(I)の調製に類似して、さらなるダイマーを製造できる。通常の調製方法を以下に示す:
2-エトキシエタノール(15mL)中のリガンド(1ミリモル)とIrCl3・3H2O(180mg、0.513ミリモル)との溶液を24時間還流する。冷却後、水(50mL)を添加し、沈殿物を濾過により集める。固形物をエタノール(20mL)とヘキサン(20mL)で洗浄し、粉末としてクロロブリッジダイマーを得る。この材料を、さらに精製しないで使用する。
さらなる錯体の調製
例10による調製に類似して、さらに錯体を製造できる。通常の調製方法を以下に示す:
クロロブリッジダイマー(Ir(Lxx)2Cl)2(0.177ミリモル)(ここではLxxはリガンドL1〜L44のうちの1つであると規定する)と、第3のリガンド(fppz、fptz、mppz、bppz、hppz、hptz、pptz、mptz、tptz又はftmpi)(0.365ミリモル)と、Na2CO3(0.85ミリモル)との混合物をエトキシエタノール(10mL)中で溶解し、反応混合物を不活性雰囲気下で、130℃で5時間加熱する。冷却後、反応混合物を水(50mL)へ注ぎ、沈殿物を濾過により集める。溶出剤としてCH2Cl2を使用して、固形物をカラムクロマトグラフィーを介して精製する。CH2Cl2/メタノールからの再結晶化によってさらに精製が行われ、赤色粉末として化合物を得る。
さらなる錯体の調製
例12による調製に類似して、さらなる錯体を製造できる。通常の調製方法を以下に示す:
化合物(Ir(Lxx)ftmpi)(0.5ミリモル)をCH2Cl2とMeOHの混合物(2:1、30mL)中に溶解させ、MeOH中のKPF6(5mL)を添加し、ここでLxxはリガンドL1〜L44のうちの1つであると規定する。室温で12時間撹拌後、溶媒を真空で取り除き、残留物を脱イオン水(50mL)で洗浄する。再結晶化は、ヘキサフルオロフォスフェイト化合物(Ir(Lxx)ftmpp)の粉末を生じる。
エレクトロルミネッセンス素子
本発明による材料を含む有機発光ダイオード(OLED)は、当業者によく知られており、文献で多数回記載されているプロセスにより作製される(例えば溶液から作製のOLEDについてはWO 2004/037887 A2、熱蒸発により作成のOLEDについてはWO 2004/058911)。
80nmのEMLをPEDOTへ直接的にスピンコートさせる。エミッターの濃度はポリマーマトリックスP1に基づいて7重量%である。全体の濃度は10g/L、即ち9.3g/LのP1、0.7g/Lのエミッターであり、スピン速度は〜1200rpmである。これらの簡略素子の最適なマトリックスはP1であり、モノマーの重合をWO 2005/040302にしたがって行う:
80nmのEMLをHIL−012へスピンコートさせる。エミッターの濃度はポリマーマトリックスP2に基づいて7重量%である。全体の濃度は10g/L、即ち9.3g/LのP2、0.7g/Lのエミッターであり、スピン速度は〜1200rpmである。これらの素子の最適なマトリックスはP2であり、モノマーの重合をWO 2005/040302にしたがって行う:
80nmのEMLをHIL−012へスピンコートさせる。可溶性小分子マトリックスは30重量%のSSM1、42重量%のSSM2、22重量%のSSM3(=組成物1)からなる。エミッターの濃度は6重量%である。全体の濃度は18g/Lであり、スピン速度は650〜1300rpmである。結果を表3にまとめる。
組成物1中の60nmのEMLをHIL−012へスピンコートさせる。エミッターの濃度は6重量%である。全体の濃度は18g/Lであり、スピン速度を(EML層の薄さにより)〜1900rpmまで増加する。50重量%のET1と50重量%のET2からなる50nmのETLをスピンコートされた層の上部に気相堆積させ、100nmのAlをかぶせる。結果を表4にまとめる。
Claims (17)
- 式(1)の化合物:
Aは、任意の芳香族もしくは複素環式芳香族構造か、または任意の芳香族もしくは複素環式芳香族ポリ環式構造であることができ;
Bは、任意のモノ環式複素環式芳香族環であり;
Cは、式(2)中で記号#で示される位置を介して任意の位置で環Dに縮合する式(2)を有する化学構造であり;、
aは、0、1または2であり;
bは、0、1または2であり;
cは、0、1、2、3または4であり;
Mは、イリジウム、ロジウム、白金およびパラジウム、好ましくは、イリジウム、白金およびパラジウム、特に、好ましくは、イリジウムおよび白金、非常に、特に、好ましくは、イリジウムより成る群から選ばれる金属であり;
nは、イリジウムもしくはロジウムであるMに対して、2であり;nは、白金もしくはパラジウムであるMに対して、1であり;環A、B、CおよびDを含む二個のリガンドは、互いに同一であるか異なることができ、好ましくは、同一であり;
R1は、出現毎に互いに同一であるか異なり、H、D、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(R2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(夫々1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族環構造もしくは複素環式芳香族環構造、1以上の基2で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基または1以上の基2で置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または2個以上のこれらの基の組み合わせから選ばれ;ここで、2個以上の基R1は、モノあるいはポリ環式の脂肪族、芳香族および/またはベンゾ縮合環構造をたがいに形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(R3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(夫々1以上の基R3により置換されてよく、1以上の隣接しないCH2基は、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、SもしくはCONR3で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R3により置換されてよい5〜60個の芳香族環原子を有する芳香族環構造もしくは複素環式芳香族環構造、1以上の基3で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基または1以上の基3で置換されてよい10〜40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または2個以上のこれらの基の組み合わせから選ばれ;ここで、2個以上の隣接する基R2は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造をたがいに形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、1〜20個のC原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基から選ばれ、さらに、1以上のH原子は、Fで置き代えられてよく;ここで、2個以上の置換基R3は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造をたがいに形成してよく;
Qは、出現毎に同一であるか異なり、R1C=CR1、R1C=N、O、S、SO2、SiR1 2、SeまたはNR1、好ましくは、R1C=CR1、SまたはNR1、特に、好ましくは、R1C=CR1またはS、非常に、特に、好ましくは、R1C=CR1から選ばれ;
X1およびX2は、出現毎に同一であるか異なり、CR1またはNから選ばれ、ここで、X1およびX2の少なくとも一つは、Nであり;
Vは、出現毎に同一であるか異なり、NR1、O、S、SO2、SiR1 2、BR1またはSe、好ましくは、NR1、O、S、特に、好ましくは、SまたはO、非常に、特に、好ましくは、Oから選ばれる。 - 縮合が、位置#1から*1もしくは*3および#2から*2を介して生じることを特徴とする請求項4項記載の化合物。
- 縮合が、位置#1から*1および#2から*2を介して生じることを特徴とする請求項4または5記載の化合物。
- X1が、Nであり、X2が、CR1であることを特徴とする請求項1乃至6何れか1項記載の化合物。
- X1およびX2の両者が、Nであることを特徴とする請求項1乃至6何れか1項記載の化合物。
- 置換基R1は、モノもしくはポリ環式の脂肪族および/または芳香族および/またはベンゾ縮合環構造を互いに形成しないことを特徴とする請求項1乃至8何れか1項記載の化合物。
- 請求項1乃至9何れか1項記載の少なくとも一つの化合物と、正孔輸送材料(HTM)、正孔注入材料(HIM)、電子輸送材料(ETM)、電子注入材料(EIM)、正孔ブロック材料(HBM)、励起子ブロック材料(ExBM)、ホストもしくはマトリックス材料、蛍光エミッター、燐光エミッター、好ましくは、ホストもしくはマトリックス材料、蛍光エミッター、燐光エミッター、特に、好ましくは、ホストもしくはマトリックス材料から選ばれる少なくとも一つのさらなる有機機能性材料とを含む組成物。
- 少なくとも一つの有機機能性材料が、好ましくは、ケトン、ホスフィンオキシド、スルホキシド、スルホン、トリアリールアミン、カルバゾール、インドロカルバゾール、インデノカルバゾール、アザカルバゾール、バイポーラーマトリックス材料、シラン、アザボロレン、ボロンエステル、トリアジン、亜鉛錯体、ジアザシあるいはテトラアザシロールもしくはジアザホスホールまたはそれらの混合物から選ばれるマトリックス材料であることを特徴とする請求項15記載の組成物。
- 請求項1乃至9何れか1項記載の少なくとも一つの化合物または請求項10もしくは11記載の少なくとも一つの組成物と少なくとも一つの溶媒とを含む調合物。
- 請求項1乃至9何れか1項記載の少なくとも一つの化合物または請求項10もしくは11記載の組成物を含み、好ましくは、有機エレクトロルミッセンス素子(OLED-有機発光ダイオード、PLED-ポリマー発光ダイオード)、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(O-TFT)、有機発光ランジスタ(O-LET)、有機太陽電池(O-SC)、有機光検査機、有機光受容体、有機電場消光素子(O-FQD)、発光電子化学電池(LEC、OLEC、LEEC)または有機レーザーダイオード(O-Laser)、特に、好ましくは、OLEDもしくは有機光発光電池(OLEC)の群より選択される電子素子。
- 一以上の発光層中に請求項16記載の組成物を含むことを特徴とする請求項13記載の素子。
- 好ましくは、OLEDもしくはOLECである、請求項1乃至9何れか1項記載の少なくとも一つの化合物または請求項10もしくは11記載の組成物を含むエレクトロルミッセンス素子の、医療における光治療のための使用。
- 好ましくは、OLEDもしくはOLECである、請求項1乃至9何れか1項記載の少なくとも一つの化合物または請求項10もしくは11記載の組成物を含むエレクトロルミッセンス素子の美容用の使用。
- 好ましくは、OLEDもしくはOLECである、請求項1乃至9何れか1項記載の少なくとも一つの化合物または請求項10もしくは11記載の組成物を含むエレクトロルミッセンス素子を使用することによる光治療による医療処置方法。
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CN104335377B (zh) | 2017-12-15 |
EP2856528A1 (en) | 2015-04-08 |
US9879177B2 (en) | 2018-01-30 |
CN104335377A (zh) | 2015-02-04 |
EP2856528B1 (en) | 2019-07-03 |
JP6324948B2 (ja) | 2018-05-16 |
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US20150105843A1 (en) | 2015-04-16 |
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