JP5763059B2 - アルキルアルコキシ基を含む構造単位を含むポリマー、これらのポリマーを含むブレンド、これらのポリマーとブレンドを含む光電子素子 - Google Patents
アルキルアルコキシ基を含む構造単位を含むポリマー、これらのポリマーを含むブレンド、これらのポリマーとブレンドを含む光電子素子 Download PDFInfo
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- JP5763059B2 JP5763059B2 JP2012516541A JP2012516541A JP5763059B2 JP 5763059 B2 JP5763059 B2 JP 5763059B2 JP 2012516541 A JP2012516541 A JP 2012516541A JP 2012516541 A JP2012516541 A JP 2012516541A JP 5763059 B2 JP5763059 B2 JP 5763059B2
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- 229920000642 polymer Polymers 0.000 title claims description 185
- 239000000203 mixture Substances 0.000 title claims description 78
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 238000002347 injection Methods 0.000 claims description 31
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- -1 NR 2 Inorganic materials 0.000 claims description 25
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- 230000008901 benefit Effects 0.000 description 6
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008208 nanofoam Substances 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 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
- 238000007650 screen-printing Methods 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
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(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
- 238000001931 thermography Methods 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 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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Description
(2)電極、一般的には、金属もしくは無機物であるが、有機もしくはポリマー伝導性材料をも含む。
(5)随意に、さらなる電荷輸送層もしくは電荷注入層もしくは電荷障壁層
(6)対電極、(2)で言及されるとおりの材料
(7)被包
上記配置は、有機電子素子の一般的構造をあらわし、種々の層は結合されてもよく、その結果、最も単純な場合には、配置は、その間に有機層が位置する二個の電極となる。有機層は、この場合、発光を含むすべての機能を発揮する。この型の系は、たとえば、ポリ(p-フェニレン)系のWO 90/13148 A1に記載されている。
R2は、各場合に、互いに独立して、Hまたは1〜20個のC原子を有する脂肪族もしくは芳香族炭化水素基である。
群1:ポリマーの正孔注入および/または正孔輸送特性に作用する単位。
正孔注入単位を含むポリマーおよび/または
正孔輸送単位を含むポリマーおよび/または
正孔障壁単位を含むポリマーおよび/または
エミッター単位を含むポリマーおよび/または
電子注入単位を含むポリマーおよび/または
電子輸送単位を含むポリマーおよび/または
電子障壁単位を含むポリマーおよび/または
励起子生成単位を含むポリマー
したがって、本発明の好ましいものは、ブレンドがさらなるポリマーを含み、夫々は、互いに独立して、正孔注入、正孔輸送、正孔障壁、電子注入、電子輸送、電子障壁、エミッター、励起子生成単位を含む。
本発明は、さらに、一以上の有機層を含む有機電子素子に関し、少なくとも一つの層は、本発明によるポリマーまたは本発明によるブレンドを含む。
有機エレクトロルミネセンス素子は、一つの発光層もしくは複数の発光層を含んでもよい。複数の発光層が存在するならば、これらは、特に好ましくは、380nm〜750nm間に全体で複数の最大発光波長を有し、全体として、白色発光が生じ、換言すれば、蛍光もしくは燐光を発することができる種々の発光化合物が発光層に使用される。特に好ましいものは、3層構造であり、その3層は青色、緑色およびオレンジ色もしくは赤色発光するものである。(基本構造については、たとえば、WO 05/011013参照。)発光素子は、たとえば、表示装置(LCD)の照明もしくはバックライトのために適している。
例1〜4において、本発明にしたがう好ましいモノマーもしくはその前駆体が調製される。例5〜7において、本発明にしたがう好ましいポリマーと比較例のポリマーが調製される。例8〜11において、本発明にしたがう好ましいブレンドが調製される。
工程2:3-(4-ブロモフェニル)プロパン-1-オル2
工程3:p-ブロモ-tert-ブチルベンゼン(1-ブロモ-4-(3-エトキシプロピル)ベンゼン)3
例2:1-ブロモ-4-(ブチルベンジルアルコール)4の調製
例3:2,8-ジブロモ-6,6-ビス(4-(3-エトキシプロピル)フェニル)-12,12-ジオクチル-6,12-ジヒドロインデノ[1,2-b]フルオレン8の調製
工程2: 6,6-ビス(4-(3-エトキシプロピル)フェニル)-12,12-ジオクチル-6,12-ジヒドロインデノ[1,2-b]フルオレン7
工程3: 2,8-ジブロモ-6,6-ビス(4-(3-エトキシプロピル)フェニル)-12,12-ジオクチル-6,12-ジヒドロインデノ[1,2-b]フルオレン8の調製
例4:2,8-ジブロモ-6,6-ビス-(1-ブロモ-4-(ブチルベンジルアルコール)-12,12-ジオクチル-6,12-ジヒドロジベンゾインデノ[1,2-b]フルオレン12の調製
工程2: 6,6-ビス-(4-(ベンジルエチルエーテル)-12,12-ジオクチル-6,12-ジヒドロジベンゾインデノ[1,2-b]フルオレン11
工程3:2,8-ジブロモ-6,6-ビス-(4-ベンジルブチルエーテル)-12,12-ジオクチル-6,12-ジヒドロジベンゾインデノ[1,2-b]フルオレン12
B)例5〜7:ポリマーの合成
以下の組成のモノマーを含むポリマーP1〜P3が、WO 03/048225にしたがってスズキカップリングにより合成される。ポリマー中のモノマーのパーセント割合は、無視できる偏差でモノマーの規格量で与えられ、ここで、臭素とボロン酸置換基は、次いで、さらなる構造単位への結合を表す。
以下の、ポリマーP9〜P13が、WO 03/048225にしたがって、対応するモノマーのスズキカップリングにより合成される。パーセントデータは、夫々のポリマー中の構造単位の割合に関する。
(a)すべての四個の個々のポリマーより、実質的にすべての特性において、明らかに優れており、
(b)同じ全体組成を有するランダムコポリマー(P13)より、寿命において、明らかに優れていることが、驚くべきことに、見出された。
本発明によるブレンドは、以下の一般的プロセスにより調製される。
Claims (23)
- 構造単位Zとして、置換あるいは非置換トランス-インデノフルオレン、ベンゾ-トランス-インデノフルオレン、ジベンゾトランス-インデノフルオレン、シス-インデノフルオレン、ベンゾ-シス-インデノフルオレン、ジベンゾ-シス-インデノフルオレン、スピロビフルオレン、ジヒドロフェナントレン、フェナントレン、フルオレン、ジベンゾフラン、ベンゾフルオレン、ベンゾクロメン、ジベンゾオキセピンおよびアントラセンから選ばれる芳香族もしくは複素環式芳香族環構造を含むポリマーであって、ここで、アルキルアルコキシ基Aは、芳香族もしくは複素環式芳香族基Arを介して、芳香族もしくは複素環式芳香族環構造に結合し、また、ここで、芳香族もしくは複素環式芳香族環構造は、一以上の置換基R1により置換される、ポリマー:
R1は、各場合に、互いに独立して、さらなる構造単位への結合であるか、または、H、D、F、Cl、Br、I、N(R2)2、N(Ar)2、C(=O)Ar、P(=O)Ar2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、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、または3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々は、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、また、1以上のH原子は、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5〜40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、または、1以上の基R2により置換されてよい5〜40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、またはこれらの構造の組み合わせであり;ここで、さらに、2個以上の置換基Rは、モノ-あるいはポリ環状、脂肪族もしくは芳香族環構造を互いに形成してもよく、
R2は、各場合に、互いに独立して、Hまたは1〜20個のC原子を有する脂肪族もしくは芳香族炭化水素基である。 - アルキルアルコキシ基Aは、式-Ark-(CR2)m-O-(CR2)o-Ox-(CR2)p-CR3にしたがい、ここで、Rは、互いに独立して、同一であるか異なり、R1に対して示された意味の一つをとることができ、CR2基は、アルケニル、アルキニル、アリールもしくはヘテロアリール基で置き代えられてよく、k≧1、m>0、o≧0であり、xは0または1であり、p≧0であり、ここで、oおよびpが0であるならば、xが0であることを特徴とする、請求項1記載のポリマー。
- 構造単位Zが、一般式IIIにしたがい、アルキルアルコキシ基Aは、芳香族もしくは複素環式芳香族基Arを介して、芳香族もしくは複素環式芳香族環構造に結合することを特徴とする、請求項1または2記載のポリマー。
- 構造単位Zおよび/または構造単位Zとは異なる一以上のさらなる構造単位の組み合わせを含むことを特徴とする、請求項1〜10何れか1項記載のポリマー。
- さらなる構造単位が、正孔注入、正孔輸送、正孔障壁、電子注入、電子輸送、電子障壁、エミッター、励起子生成単位または骨格単位から選ばれることを特徴とする、請求項11記載のポリマー。
- さらなる構造単位が、一般式Va、Vb、Vc、Vd、Ve、Vf、VgおよびVhか
ら選ばれることを特徴とする、請求項11または12記載のポリマー。
- ポリマーが共役または部分共役ポリマーおよび/またはブロックコポリマーである、請求項1〜13何れか1項記載のポリマー。
- 請求項1〜14何れか1項記載のポリマーと少なくとも一つの更なる有機、有機金属またはポリマー化合物を含むブレンド。
- さらなるポリマー化合物が、正孔注入、正孔輸送、正孔障壁、電子注入、電子輸送、電子障壁、エミッター、励起子生成単位または骨組単位および前記構造単位の組み合わせか
ら選ばれる構造単位を含むことを特徴とする、請求項15記載のブレンド。 - さらなるポリマー化合物が、構造単位Va、Vb、Vc、Vd、Ve、Vf、VgおよびVhを含むことを特徴とする、請求項15または16記載のブレンド。
- 請求項1〜14何れか1項記載のポリマー、エミッター単位を含むポリマー化合物およ
び正孔障壁単位を含むポリマー化合物を含む、請求項15〜17何れか1項記載のブレン
ド。 - さらなるポリマーを含み、夫々が、互いに独立して、正孔注入、正孔輸送、正孔障壁、電子注入、電子輸送、電子障壁、エミッターもしくは励起子生成単位を含むことを特徴とする、請求項15〜18何れか1項記載のブレンド。
- 請求項1〜14何れか1項記載のポリマーまたは請求項15〜19何れか1項記載のブレンドの、有機電子素子での使用。
- 請求項1〜14何れか1項記載のポリマーまたは請求項15〜19何れか1項記載のブ
レンドと一以上の溶媒を含む調合物。 - 有機電子素子であって一以上の層を含み、少なくとも一つの層は、請求項1〜14何れか1項記載のポリマーまたは請求項15〜19何れか1項記載のブレンドを含む、有機電
子素子。 - 有機電子素子は、有機エレクトロルミネッセンス素子(OLED)、ポリマーエレクトロルミネッセンス素子(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)、有機発光トランジスタ(OLET)、有機太陽電池(O-SC)、有機光学検査素子、有機光受容器、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)もしく有機レーザーダイオード(O-laser)であることを特徴とする、請求項22記載の有機電子素子。
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