JP5836934B2 - 置換インデノフルオレン誘導体を構造単位として含むポリマー、その調製方法およびその使用 - Google Patents
置換インデノフルオレン誘導体を構造単位として含むポリマー、その調製方法およびその使用 Download PDFInfo
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- JP5836934B2 JP5836934B2 JP2012512226A JP2012512226A JP5836934B2 JP 5836934 B2 JP5836934 B2 JP 5836934B2 JP 2012512226 A JP2012512226 A JP 2012512226A JP 2012512226 A JP2012512226 A JP 2012512226A JP 5836934 B2 JP5836934 B2 JP 5836934B2
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- 239000013307 optical fiber Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Description
破線は、互いに独立して、さらなるポリマーの構造単位への結合を表し、
L1およびL2は、互いに独立して、単共有結合またはC1-10アルキレン基、C2-10アルケニレン基、C2-10アルキニレン基およびSi1-10シリレン基から成る基より選択される基であって、1以上のCH2単位は、NR、OまたはSにより置き代えられてよく、1以上のSiH2単位は、Oにより置き代えられてよい。
EおよびJは、夫々、互いに独立して、CRおよびNから成る基より選択される単位であり、
nは、1、2または3であり、および
mは、0、1または2であり、ここで、
Rは、H、FおよびC1−6アルキルから成る基より選択される基であり、
但し、E、DおよびJからの唯一の代表はCRまたはCR2ではなく、
ここで、四価の単位Wが、式(II)または(III)の単位である場合には、C1およびC3は、単位Wの異なる原子と結合し、
U、VおよびV‘は、互いに独立して、単共有結合またはCR1R2、C=O、NR1、O、SiR1R2、P=O、SおよびGeR1R2から成る基より選択される二価単位であり、
ここで、R1およびR2は、互いに独立して、H、F、C1−40アルキル基、C2−40アルケニル基、C2−40アルキニル基、随意に置換されたC6−40アリール基および随意に置換された5〜25員環ヘテロアリール基から成る基より選択され、
C1〜C8は、夫々、C原子を表し、
Ar1およびAr2は、夫々、互いに独立して、5〜25員環の随意に置換された芳香族もしくは複素環式芳香族環構造を表し、
Ar3、Ar4およびAr5は、互いに独立して、随意に置換されたC6−40アリール基または随意に置換された5〜25員環ヘテロアリール基を表し、ここで、C原子C1およびC2は、Ar3の一部であり、C原子C3〜C6は、Ar4の一部であり、C原子C7およびC8はAr5の一部である。
群1:ポリマーの正孔注入および/または正孔輸送特性を向上する単位。
(B)ヤマモト重合;
(C)スチル(STILLE)重合;
(D)ヘック(HECK)重合;
(E)ネギシ(NEGISHI)重合;
(F)ソノガシラ(SONOGASHIRA)重合;
(G)ヒヤマ(HIYAMA)重合;および
(H)ハートウイッグ-ブーフバルト(HARTWIG-BUCHWALD)重合;
これらの方法により重合を行うことができる方法およびポリマーを反応媒体から分離し、純化することのできる方法は、当業者に知られ、文献、たとえば、WO 03/048225 A2、WO 2004/037887 A2およびWO 2004/037887 A2に記載されている。
ZおよびZ‘は、互いに独立して、ハロゲン、O-トシレート、O-トリフレート、O-SO2R3、B(OR3)2およびSn(R3)3から成る基より選択され、ここで、R3は、互いに独立して、出現毎に、H、1〜20個のC原子を有する脂肪族炭化水素基もしくは5〜20個の環原子を有する芳香族炭化水素基であり、二個以上の基R3は、互いに脂肪族環構造を形成してもよく、ここで、他の記号は、上記具体例と同じ意味を有する。式(I)の構造単位の好ましい具体例が、ここで、再度、好ましい具体例である。
Mは、出現毎に同一であるか異なり、原子番号>36を有する主族金属、遷移金属またはランタノイド金属であり、
DCyは、出現毎に同一であるか異なり、それを介して環状基が金属に結合し、一以上の置換基R4を担持してもよい、少なくとも一つのドナー原子、すなわち、自由電子対を有する原子、好ましくは、窒素または燐を含む環状基であり、基DCyおよびCCyは互いに共有結合により連結し、基R4および/またはR5を介して、互いに更なる連結を有してもよく、
CCyは、出現毎に同一であるか異なり、それを介して環状基が金属に結合し、一以上の置換基R4を担持してもよい、炭素原子を含む環状基であり、
Lは、出現毎に同一であるか異なり、二座キレートリガンド、好ましくは、モノアニオン性二座キレートリガンドであり、
R4は、出現毎に同一であるか異なり、H、F、Cl、Br、I、NO2、CN、1〜40個のC原子を有する直鎖、分岐鎖または環状アルキルもしくはアルコキシ基(1以上の隣接しないCH2単位は、C=O、C=S、C=Se、C=NR5、R5C=CR5、-C≡C-、-O-、-S-、-NR5、Si(R5)またはCONR5により置き代えられてよく、ここで、一以上のH原子は、F、Cl、Br、I、CN、NO2により置き代えられてよい。)または一以上の非芳香族基R4により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、複数の置換基R4は、同一の環上または二個の異なる環上で、一緒になって、順に、さらなるモノ、ポリ、脂肪族あるいは芳香族環構造を形成してよく、
R5は、出現毎に同一であるか異なり、H、1〜20個のC原子を有する脂肪族炭化水素基または6〜20個のC原子を有する芳香族炭化水素基であり、
mは、1、2または3であり、好ましくは、2または3であり、特に、好ましくは、3であり、
nは、0、1または2であり、好ましくは、0または1であり、特に、好ましくは、0である。
1.2 化合物3
1.3 化合物4
例2
化合物9の調製
化合物9は、以下のとおり調製される。
2.2 化合物7
2.4 化合物9
例3〜10:ポリマーの調製
本発明によるポリマーP1およびP2と比較例のポリマーC1が、WO 03/048225 A2に従って、スズキカップリングにより、以下のモノマー(パーセンテージデータ=モル%)を使用して合成される。
ポリマーP1およびP2は、緑色三重項発光のためのマトリックにおける本発明の素子の基本的な適合性を示すために非常に高度に適切であるが、それらは、正孔もしくは電子輸送に貢献することができる更なる単位を全く含まない。したがって、三重項エミッターを既に含むさらなるポリマーが、この場合はコポリマーであるが、合成される。ポリマーP3は共役中断骨組を含み、比較例のポリマーC2は、共役骨組である。
本発明のポリマーP1およびP2の場合に既に説明したとおり、三重項素子は、三重項エミッターとマトリックスとの組み合わせにより製造することもできる。ポリマーP4〜P6は、追加的な機能単位(群1または2からの、詳細な説明参照。)を含むポリマーである。
ポリマー有機発光ダイオード(PLED)は、文献(たとえば、WO 2004/037887 A2)に何度も既に記載されるとおりに、製造される。本発明を実例で説明するために、PLEDが、スピンコーティングにより、ポリマーP3〜P6と比較例のポリマーC2で製造される。典型的素子は、図2に示される構造を有する。
Claims (22)
- 少なくとも一つの式(I)の構造単位を含むポリマー。
破線は、互いに独立して、さらなるポリマーの構造単位への結合を表し、
L1およびL2は、互いに独立して、単共有結合またはC1−10アルキレン基、C2−10アルケニレン基、C2−10アルキニレン基およびSi1-10シリレン基から成る基より選択される単位であって、1以上のCH2単位は、NR、OまたはSにより置き代えられてよく、1以上のSiH2単位は、Oにより置き代えられてよく;
Wは、C、Si、Ge並びに以下の式(II)および(III)の構造要素から成る群より選択される四価の単位を表し;
Dは、出現毎に同一であるか異なり、CR2、O、SおよびNRから成る基より選択される単位であり、
EおよびJは、互いに独立して、CRおよびNから成る基より選択される単位であり、
nは、1、2または3であり、および
mは、0、1または2であり、ここで、
Rは、H、FおよびC1−6アルキルから成る基より選択される基であり、
但し、E、DおよびJからの唯一のものはCRまたはCR2とは異なり、
ここで、四価の単位Wが式(II)または(III)の単位である場合には、C1およびC3は、単位Wの異なる原子と結合し、
V‘は、単共有結合であり、UとVからの一つが、単共有結合を表し、他方が、CR1R2単位を表し、
ここで、
R1およびR2は、互いに独立して、C 1−40アルキル基、C2−40アルケニル基、C2−40アルキニル基、随意に置換されたC6−40アリール基および随意に置換された5〜25員環ヘテロアリール基から成る基より選択され、
C1〜C8は、夫々、C原子を表し、
Ar1およびAr2は、夫々、互いに独立して、5〜25員環の随意に置換された芳香族もしくは複素環式芳香族環構造をそれぞれ表し、
Ar3、Ar4およびAr5は、互いに独立して、随意に置換されたC6−40アリール基または随意に置換された5〜25員環ヘテロアリール基を表し、ここで、C原子C1およびC2は、Ar3の一部であり、C原子C3〜C6は、Ar4の一部であり、C原子C7およびC8は、Ar5の一部である。) - L1およびL2は、単共有結合を表すことを特徴とする、請求項1記載のポリマー。
- Wは、C、SiまたはGeを表すことを特徴とする、請求項1または2記載のポリマー。
- ポリマーが部分共役ポリマーであり、共役は式(I)の構造単位により中断されることを特徴とする、請求項1〜5何れか1項記載のポリマー。
- 式(I)の構造単位に加えて、少なくとも一つのさらなる構造単位を含むことを特徴とする、請求項1〜6何れか1項記載のポリマー。
- 少なくとも一つのさらなる構造単位が三重項エミッター単位であることを特徴とする、請求項7記載のポリマー。
- トリアリールアミン、ベンジジン、テトラアリール-パラ-フェニレンジアミン、トリアリールホスフィン、フェノチアジン、フェノキサジン、ジヒドロフェナジン、チアントレン、ジベンゾ-パラ-ジオキシン、フェノキサチン、カルバゾール、アズレン、チオフェン、ピロールおよびフラン誘導体ならびにポリマー中で−5.8eVを超えるHOMOを有する更なるO-、S-もしくはN-含有ヘテロ環の基から選択される少なくとも一つのさらなる構造単位を含むことを特徴とする、請求項7または8記載のポリマー。
- ピリジン、ピリミジン、ピリダジン、ピラジン、オキサジアゾール、キノリン、キノキサリン、アントラセン、ベンズアントラセン、ピレン、ペリレン、ベンズイミダゾール、トリアジン、ケトン、ホスフインオキシドおよびフェナジン誘導体のみならずトリアリールボランならびに−1.9eV未満のLUMOを有する更なるO-、S-もしくはN-含有ヘテロ環の基から選択される少なくとも一つのさらなる構造単位を含むことを特徴とする、請求項7〜9何れか1項記載のポリマー。
- 4,5-ジヒドロピレン、4,5,9,10-テトラヒドロピレン、フルオレン、9,9’-スピロビフルオレン、フェナントレン、9,10-ジヒドロフェナントレン、5,7-ジヒドロジベンゾオキセピンならびにシス-およびトランス-インデノフルオレン誘導体から選択される少なくとも一つのさらなる構造単位を含むことを特徴とする、請求項7〜10何れか1項記載のポリマー。
- スズキ重合、ヤマモト重合、スチル重合またはハートウイッグ-ブーフバルト重合によって調製されることを特徴とする、請求項1〜11何れか1項記載のポリマーの調製方法。
- ZおよびZ‘は、互いに独立して、Br、IおよびB(OR3)2から選択されることを特徴とする、請求項13記載の化合物。
- 請求項1〜11何れか1項記載のポリマーと、更なるポリマー状、オリゴマー状、樹状および/または低分子量物質を含む混合物。
- 低分子量物質が三重項エミッターである、請求項15記載の混合物。
- 1以上の溶媒中に、請求項1〜11何れか1項記載のポリマーを含む、または請求項15もしくは16記載の混合物を含む溶液。
- 請求項1〜11何れか1項記載のポリマー、または請求項15または16記載の混合物または請求項17記載の溶液の、有機電子素子における使用。
- 請求項1〜11何れか1項記載のポリマー、または請求項15または16記載の混合物または請求項17記載の溶液の、有機エレクトロルミネッセンス素子における使用。
- 少なくとも一つの活性層が、請求項1〜11何れか1項記載のポリマーまたは請求項15または16記載の混合物を含むことを特徴とする、一以上の活性層を有する有機電子素子。
- 有機もしくはポリマー有機エレクトロルミネッセンス素子(OLED、PLED)、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)、有機太陽電池(O-SC)、有機レーザーダイオード(O-laser)、有機光電池(OPV)要素あるいは素子もしくは有機光受容器(OPC)であることを特徴とする、請求項20記載の有機電子素子。
- ポリマー有機エレクトロルミネッセンス素子(PLED)であることを特徴とする、請求項21記載の有機電子素子。
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PCT/EP2010/002684 WO2010136110A2 (de) | 2009-05-29 | 2010-05-03 | Polymere, die substituierte indenofluorenderivate als struktureinheit enthalten, verfahren zu deren herstellung sowie deren verwendung |
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DE112010002181A5 (de) | 2012-05-16 |
US20120061617A1 (en) | 2012-03-15 |
US9349960B2 (en) | 2016-05-24 |
WO2010136110A3 (de) | 2011-05-26 |
TW201114797A (en) | 2011-05-01 |
WO2010136110A2 (de) | 2010-12-02 |
JP2012528208A (ja) | 2012-11-12 |
DE102009023156A1 (de) | 2010-12-02 |
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