JP2012519215A - 架橋性ポリマー、架橋ポリマー、これらの調製方法及びこれらの使用 - Google Patents
架橋性ポリマー、架橋ポリマー、これらの調製方法及びこれらの使用 Download PDFInfo
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- JP2012519215A JP2012519215A JP2011551426A JP2011551426A JP2012519215A JP 2012519215 A JP2012519215 A JP 2012519215A JP 2011551426 A JP2011551426 A JP 2011551426A JP 2011551426 A JP2011551426 A JP 2011551426A JP 2012519215 A JP2012519215 A JP 2012519215A
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- 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 150000001608 tolans Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 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
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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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Abstract
【選択図】なし
Description
(1) 基板、
(2) 電極、しばしば金属又は無機の電極であるだけでなく、有機又は高分子の導電材料を含み、
(3) 例えば電極(平坦化層)のばらつきを水平にするために導電性のドープポリマーをしばしば含む電荷注入層あるいは中間層、
(4) 有機半導体、
(5) 任意的にさらに電荷輸送、電荷注入あるいは電荷障壁層、
(6) 対極、下記(2)で述べた材料
(7) カプセル封入。
SMOLEDsにおける層は、通常、真空チャンバー内で蒸着によって利用される。しかしながら、この方法は複雑で、それゆえに高価で、特に、例えばポリマーのような大きな分子に不適当である。
A)モノマーの調製
実施例1
モノマー1の調製
モノマー1の調製は、下記に表現されたスキーム1に従う。個々の工程における反応は、当業者に知られた有機化学の一般的な方法に従って実施される。ここでの反応条件は、最大生産収率が個々の工程で達成されるように、反応継続時間、温度、圧力等について、それぞれの反応に従って選択される。反応の工程は、例えば、薄層クロマトグラフィーによってモニタすることができる。
B)ポリマーの調製
実施例3〜6
発明に係るポリマーP1〜P3及び比較ポリマーC1の調製
発明に係るポリマーP1〜P3及び比較ポリマーC1は、WO03/048225に従ったSUZUKIカップリングにより合成される。モノマー単位は、百分率の記載と共に下記に示されたモノマーと対応するポリマーP1〜P3及び比較ポリマーC1の合成のために使用され、対応するポリマー中に本質的に未変化のまま回収されることが可能である。
実施例7〜10
高分子発光ダイオード(PLED)の生産は、既に、特許文献(例えばWO04/037887)に多数回に亘って記載されている。実施例の方法によって本発明を説明するため、PLEDsは、ポリマーP1〜P3及び比較ポリマーC1を用い、予めPEDOTが塗布されたITO基板上及び正孔注入中間層(PEDOTはポリチオフェン誘導体(Baytron P,from H.C.Starck,Goslar))上にスピンコートすることによって生産される。ポリマー層の層厚さは、約65nmである。ポリマーP1〜P3は、架橋させるため、スピンコーティング後、180℃でさらに1時間加熱される。Ba/Alカソード(metals from Aldrich)は、その後、蒸着によって塗布され、PLEDsは内部に封じ込められ、電気光学的に特徴付けられる。
ポリマーP1〜P3は、PEDOT及びITOが塗布された基板に、スピンコーティングによって塗布される。層厚さは測定される。ポリマー膜は、架橋のため、180℃で1時間加熱される。膜は、その後、トルエンで“洗浄”され(スピンコータ上)、180℃で10分間再度加熱される。そして、ポリマーが洗い落とされているか、すなわち架橋が成功したか否かを確認するため、層厚さは再び測定される。
Claims (16)
- 一般式Iの構造単位を少なくも一つ含むポリマー。
- Qはビニル又はアルケニル基であることを特徴とする請求項1記載のポリマー。
- Xは、直接結合、直鎖もしくは枝分かれで炭素数1〜20のアルキレン基であり、ここで一又はそれ以上の隣り合わないCH2基は、−O−,−S−,−NH−,N(CH3)−,−N−CO−,−N−CO−O−,−N−CO−N,−CO−,−O−CO−,−S−CO−,−O−COO−,−CO−S−,−CO−O−,−CH(halogen)−,−CH(CN)−,−CH=CH−あるいは−C≡C−,あるいは環状アルキル基出会って良いことを特徴とする請求項1または2記載のポリマー。
- Zは、環の原子数が5〜60の芳香族あるいは複素芳香族の環系であり、あらゆる所望の種類の一またはそれ以上のラジカルRによって置換されて良いことを特徴とする請求項1〜3いずれか1項記載のポリマー。
- Ar1,Ar2は、それぞれ、互いに独立して、環の原子数が5〜60のアリール又はヘテロアリール基であり、あらゆる所望の種類の一またはそれ以上のラジカルRによって置換されて良いことを特徴とする請求項1〜4いずれか1項記載のポリマー。
- Ar1は、1,4位に結合されたアリール又はヘテロアリール基であり、あらゆる所望の種類の一またはそれ以上のラジカルRによって置換されて良いことを特徴とする請求項1〜5いずれか1項記載のポリマー。
- Rは、出現毎に、互いに独立して、F,Cl,Br,I,N(Ar)2,N(R2)2,CN,NO2,Si(R2)3,B(OR2)2,C(=O)Ar,C(=O)R2,P(=O)(Ar)2,P(=O)(R2)2,S(=O)Ar,S(=O)R2,S(=O)2Ar,S(=O)2R2,−CR2=CR2Ar,OSO2R2,C原子数1〜40で、直鎖の、アルキル、アルコキシ又はチオアルコキシ基;C原子数3〜40で、枝分かれまたは環状の、アルキル、アルコキシ又はチオアルコキシ基、それぞれ一またはそれ以上のラジカルR2によって置換されていて良く、ここで一又はそれ以上の隣り合わない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又はCONR2によって置換されて良く、ここにおいて一またはそれ以上のH原子は、F,Cl,Br,I,CNまたはNO2によって置換されていて良い;それぞれの場合において一またはそれ以上のラジカルR2によって置換されていて良い、芳香族環の原子数が5〜60の芳香族又は複素芳香族の環系;一またはそれ以上のラジカルR2によって置換されていて良い、芳香族環の原子数が5〜60のアリールオキシ又はヘテロアリールオキシ基;、又は、これらの系の組み合わせ;から選択され、ここで、二又はそれ以上の置換基Rは、単環式又は多環式の、脂肪族又は芳香族の環系を互いに形成しても良く、ここで、R2は、それぞれの場合において互いに独立に、Hか、1〜20のC原子数の、脂肪族又は芳香族の炭化水素ラジカルであることを特徴とする請求項1〜6いずれか1項記載のポリマー。
- 一般式Iとは異なる構造単位をさらに含むことを特徴とする請求項1〜7いずれか1項記載のポリマー。
- Y1,Y2は、それぞれ、互いに独立に、ハロゲン化合物、ホウ酸、ホウ酸エステル、ボラン、メシル酸(mesitylate)及びトリフラートから選択されることを特徴とする請求項9記載の化合物。
- 架橋性及び/または架橋ポリマーの調製のための、請求項9または10の化合物の使用。
- 一またはそれ以上の溶媒中での請求項1〜8いずれか1項記載のポリマーを含む形成。
- 請求項1〜8いずれか1項記載のポリマーを含む電子素子。
- 前記ポリマーが架橋されていることを特徴とする請求項13記載の電子素子。
- 前記ポリマーは、正孔輸送、正孔注入、エミッタ、電子輸送、電子注入、電荷障壁及び/または電荷発生の層として前記素子中に存在することを特徴とする請求項13又は14記載の電子素子。
- 有機エレクトロルミネセンスデバイス(OLED)、高分子エレクトロルミネセンスデバイス(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(O−LET)、有機太陽電池(O−SC)、有機光学検波器、有機光受容体、有機電場消光デバイス(O−FQD)、発光電気化学セル(LEC)または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13〜15いずれか1項記載の電子素子。
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WO2019059331A1 (ja) * | 2017-09-22 | 2019-03-28 | 三菱ケミカル株式会社 | 電荷輸送性化合物、電荷輸送性化合物を含む組成物及び該組成物を用いた有機電界発光素子 |
JPWO2019059331A1 (ja) * | 2017-09-22 | 2020-11-05 | 三菱ケミカル株式会社 | 電荷輸送性化合物、電荷輸送性化合物を含む組成物及び該組成物を用いた有機電界発光素子 |
JP7310605B2 (ja) | 2017-09-22 | 2023-07-19 | 三菱ケミカル株式会社 | 電荷輸送性化合物、電荷輸送性化合物を含む組成物及び該組成物を用いた有機電界発光素子 |
Also Published As
Publication number | Publication date |
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EP2401315B1 (de) | 2018-08-22 |
CN102307926A (zh) | 2012-01-04 |
US20110303877A1 (en) | 2011-12-15 |
KR20110129929A (ko) | 2011-12-02 |
WO2010097156A1 (de) | 2010-09-02 |
EP2401315A1 (de) | 2012-01-04 |
CN102307926B (zh) | 2014-11-26 |
DE102009010714A1 (de) | 2010-09-02 |
KR101676510B1 (ko) | 2016-11-15 |
US9315617B2 (en) | 2016-04-19 |
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