JP2020526025A - フェノール系不純物の含有量が低い調合物 - Google Patents
フェノール系不純物の含有量が低い調合物 Download PDFInfo
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- JP2020526025A JP2020526025A JP2019571994A JP2019571994A JP2020526025A JP 2020526025 A JP2020526025 A JP 2020526025A JP 2019571994 A JP2019571994 A JP 2019571994A JP 2019571994 A JP2019571994 A JP 2019571994A JP 2020526025 A JP2020526025 A JP 2020526025A
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000005029 thianthrenes Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 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 Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E10/549—Organic PV cells
Abstract
Description
背景および先行技術
有機発光デバイス(OLED)は、長い間真空蒸着法によって作成されてきた。他の技法、例えばインクジェット印刷が、その利点、例えばコスト削減や規模拡大の可能性のために、最近は徹底的に検討されている。多層印刷における主な課題の1つは、基板上にインクの均一な堆積を得るための関連するパラメータを特定することである。これらのパラメータ、例えば表面張力、粘度または沸点を誘導するため、数種の添加剤を調合物に添加することができる。
技術的課題および本発明の目的
有機電子デバイスでは、インクジェット印刷用に多くの溶媒が提案されてきた。しかし、堆積および乾燥プロセス時に役割を果たす重要なパラメータの数が、溶媒の選択を非常に困難にしている。したがって、インクジェット印刷による堆積に使用される有機半導体を含有する調合物は、依然として改良の必要がある。本発明の1つの目的は、良好な層特性と効率的な性能を有する有機半導体層を形成するための制御された堆積を可能とする有機半導体の調合物を提供することである。本発明のさらなる目的は、例えばインクジェット印刷法を使用して基板上に堆積させ乾燥させたときに、優れた膜均一性を可能とし、それによって良好な層特性と効率的な性能をもたらす有機半導体の調合物を提供することである。
発明の概要
本発明は、1種以上の有機半導体材料と1種以上の有機溶媒を含む調合物であって、調合物が100ppm未満のフェノール系不純物を含有することを特徴とする調合物に関する。
R1、R2、R3、R4およびR5は、それぞれの出現において同一であるかまたは異なり、H、1〜20個の炭素原子を有する直鎖アルキル基または3〜20個の炭素原子を有する分枝もしくは環状アルキル基(ここで、1つ以上の隣接していないCH2基は、−O−、−S−、−NR6−、−CONR6−、−CO−O−、−C=O−、−CH=CH−または−C≡C−によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)、または2〜60個の炭素原子を有するアリールもしくはヘテロアリール基であり、前述の基は1つ以上のR6ラジカルによって置換されていてもよく、R3およびR4はまた、一緒になって単環または多環式の脂肪族、芳香族またはヘテロ芳香族環系を形成してもよく;
R6は、それぞれの場合において同一であるかまたは異なり、H、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基または3〜20個の炭素原子を有する分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1個以上の水素原子は、D、F、Cl、Br、I、CNまたはNO2によって置きかえられていてもよい)、または2〜14個の炭素原子を有するアリールもしくはヘテロアリール基である)
による化合物である。
DCyは、出現する毎に同一であるかまたは異なり、少なくとも1個の供与体原子、好ましくは、窒素、カルベンの形態の炭素、またはリンを含有する環状基であり、この供与体原子を介して環状基は金属に結合し、環状基はまた、1つ以上の置換基R1を有していてもよく;基DCyとCCyは、共有結合を介して互いに結合しており;
CCyは、出現する毎に同一であるかまたは異なり、炭素原子を含有する環状基であり、この炭素原子を介して環状基は金属に結合し、環状基はまた、1つ以上の置換基R1を有していてもよく;
Aは、出現する毎に同一であるかまたは異なり、モノアニオン性二座キレート配位子、好ましくはジケトネート配位子であり;
R1は、それぞれの場合において同一であるかまたは異なり、F、Cl、Br、I、NO2、CN、1〜20個の炭素原子を有する直鎖、分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1つ以上の隣接していないCH2基は、−O−、−S−、−NR2−、−CONR2−、−CO−O−、−C=O−、−CH=CH−または−C≡C−によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)、または4〜14個の炭素原子を有し、1つ以上の非芳香族R1ラジカルによって置換されていてもよいアリールもしくはヘテロアリール基であり、複数の置換基R1はまた、同じ環上または2つの異なる環上の何れかで、一緒になって単環または多環式の脂肪族または芳香族環系を形成してもよく;
R2は、それぞれの場合において同一であるかまたは異なり、1〜20個の炭素原子を有する直鎖、分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1つ以上の隣接していないCH2基は、−O−、−S−、−CO−O−、−C=O−、−CH=CH−または−C≡C−によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)、または4〜14個の炭素原子を有し、1つ以上の非芳香族R1ラジカルによって置換されていてもよいアリールもしくはヘテロアリール基である)
の化合物である。
群1:ポリマーの正孔注入および/または正孔輸送特性に影響を与える、好ましくは特性を強化する単位;
群2:ポリマーの電子注入および/または電子輸送特性に影響を与える、好ましくは特性を強化する単位;
群3:群1および群2からの個々の単位の組合せを有する単位;
群4:電気蛍光ではなく電気リン光が得られる程度に発光特性を変更する単位;
群5:一重項状態から三重項状態への遷移を改善する単位;
群6:結果として得られるポリマーの発光色に影響を与える単位;
群7:典型的には骨格として使用される単位;
群8:結果として得られるポリマーの膜形態学的および/または流動学的特性に影響を与える単位。
Hdは、分散寄与度を指し、
Hpは、極性寄与度を指し、
Hhは、水素結合寄与度を指し、
MVolは、モル体積を指す)。
作成方法の説明
事前に構造化したITOとバンク材料で被覆したガラス基板をイソプロパノール中とそれに続く脱イオン水中での超音波処理を使用して清浄化し、次いで、エアガンを使用して乾燥させ、その後ホットプレート上で、230℃で2時間アニーリングした。
表2は、1000cd/m2での発光効率と外部量子効率(EQE)、および6000cd/m2でのデバイス寿命(LT80)を要約したものである。例におけるデバイスは、参考と同様の効率を示す。ただし、例の寿命は、参考よりも低い値を示した。これは、フェノール系不純物が、デバイス操作寿命を約30%短縮したことを意味する。したがって、OLEDインクでは、フェノール系不純物を除去するか、できる限り低く保つべきである。
Claims (18)
- 1種以上の有機半導体材料と1種以上の有機溶媒を含む調合物であって、前記調合物が100ppm未満のフェノール系不純物を含有することを特徴とする、調合物。
- 前記フェノール系不純物が、下記一般式(I)
R1、R2、R3、R4およびR5は、それぞれの出現において同一であるかまたは異なり、H、1〜20個の炭素原子を有する直鎖アルキル基または3〜20個の炭素原子を有する分枝もしくは環状アルキル基(ここで、1つ以上の隣接していないCH2基は、−O−、−S−、−NR6−、−CONR6−、−CO−O−、−C=O−、−CH=CH−または−C≡C−によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)、または2〜60個の炭素原子を有するアリールもしくはヘテロアリール基であり、前述の基は1つ以上のR6ラジカルによって置換されていてもよく、R3およびR4は、一緒になって単環または多環式の脂肪族、芳香族またはヘテロ芳香族環系を形成してもよく;
R6は、それぞれの場合において同一であるかまたは異なり、H、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基または3〜20個の炭素原子を有する分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1個以上の水素原子は、D、F、Cl、Br、I、CNまたはNO2によって置きかえられていてもよい)、または2〜14個の炭素原子を有するアリールもしくはヘテロアリール基である)
による化合物であることを特徴とする、請求項1に記載の調合物。 - 前記調合物が、10ppm未満のフェノール系不純物を含有することを特徴とする、請求項1または2に記載の調合物。
- 前記有機半導体材料が、5,000g/molを超える分子量Mwを有するポリマーであることを特徴とする、請求項1〜3の何れか1項に記載の調合物。
- 前記有機半導体材料が、5,000g/mol以下の分子量を有する低分子量材料であることを特徴とする、請求項1〜4の何れか1項に記載の調合物。
- 前記有機半導体材料が、正孔注入、正孔輸送、電子阻止、発光、正孔阻止、電子輸送、電子注入および誘電吸収体材料から選択されることを特徴とする、請求項1〜5の何れか1項に記載の調合物。
- 前記調合物が1種の溶媒を含有することを特徴とする、請求項1〜6の何れか1項に記載の調合物。
- 前記溶媒が、90℃以上、好ましくは150℃以上、より好ましくは200℃以上の沸点を有することを特徴とする、請求項7に記載の調合物。
- 前記調合物が、少なくとも2種の異なる溶媒を含有し、前記少なくとも2種の異なる溶媒のうちの2種の溶媒の沸点の差が10℃以上であることを特徴とする、請求項1〜8の何れか1項に記載の調合物。
- 前記調合物が少なくとも2種の異なる溶媒を含有し、前記少なくとも2種の異なる溶媒のうちの2種の溶媒の蒸気圧の差が2倍以上、好ましくは10倍以上であることを特徴とする、請求項1〜9の何れか1項に記載の調合物。
- 前記調合物が、1.5〜100mPasの範囲、好ましくは2.0〜40mPasの範囲、より好ましくは2.1〜20mPasの範囲の粘度を有することを特徴とする、請求項1〜10の何れか1項に記載の調合物。
- 前記調合物が、添加剤および/または助剤を含有することを特徴とする、請求項1〜11の何れか1項に記載の調合物。
- 前記調合物が、少なくとも1種のポリマーバインダーを添加剤として含有することを特徴とする、請求項12に記載の調合物。
- 請求項1〜13の何れか1項に記載の調合物を調製するための方法であって、前記1種以上の有機半導体材料を1種以上の有機溶媒に溶解させ、その後調合物をろ過することを特徴とする、方法。
- 電子デバイスの少なくとも1つの層を調製するための方法であって、前記少なくとも1つの層が、請求項1〜13の何れか1項に記載の調合物を使用したディップコーティング、スピンコーティング、インクジェット印刷、ノズル印刷、活版印刷、スクリーン印刷、グラビア印刷、ドクターブレードコーティング、ローラー印刷、逆ローラー印刷、オフセットリソグラフィ印刷、フレキソ印刷、ウェブ印刷、スプレーコーティング、カーテンコーティング、ブラシコーティング、エアブラシコーティング、スロットダイコーティングまたはパッド印刷によって調製される、方法。
- 前記電子デバイスが、OLED、OTFT、OFET、ソーラーセル、センサ、有機ダイオード、およびRFIDからなる群から選択される、請求項15に記載の方法。
- 電子デバイスの少なくとも1つ層の調製のための請求項1〜13の何れか1項に記載の調合物の使用。
- 前記電子デバイスが、OLED、OTFT、OFET、ソーラーセル、センサ、有機ダイオード、およびRFIDからなる群から選択されることを特徴とする、請求項17に記載の使用。
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US20210151679A1 (en) | 2021-05-20 |
EP3649202A1 (en) | 2020-05-13 |
KR20200024267A (ko) | 2020-03-06 |
JP7282694B2 (ja) | 2023-05-29 |
TW201906939A (zh) | 2019-02-16 |
TWI813576B (zh) | 2023-09-01 |
WO2019007823A1 (en) | 2019-01-10 |
CN110809612A (zh) | 2020-02-18 |
US11211557B2 (en) | 2021-12-28 |
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