JP2018507264A - 改質量子ドット及びその製造方法、着色剤、感光性樹脂組成物、カラーフィルタと表示装置 - Google Patents
改質量子ドット及びその製造方法、着色剤、感光性樹脂組成物、カラーフィルタと表示装置 Download PDFInfo
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- JP2018507264A JP2018507264A JP2016573480A JP2016573480A JP2018507264A JP 2018507264 A JP2018507264 A JP 2018507264A JP 2016573480 A JP2016573480 A JP 2016573480A JP 2016573480 A JP2016573480 A JP 2016573480A JP 2018507264 A JP2018507264 A JP 2018507264A
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Abstract
Description
前記アミンにおける一部又は全てのアミノ基と酸性染料を造塩結合し、
Y−は酸性染料のアニオンであり、R1、R2、R3、R4、R5、R6はそれぞれ独立にH又はC1〜C6の炭化水素基である。
C6〜C22炭化水素基を含むアミンを結合した量子ドットを製造し、
オニウム塩化試薬を用いて前記量子ドットをオニウム塩化して、アンモニウム塩基を含む量子ドットを形成し、
前記アンモニウム塩基を含む量子ドットを酸性染料と反応させて造塩し、前記改質量子ドットを得る、ことを含む。
前記アミンにおける一部又は全てのアミノ基と酸性染料を造塩結合し、
Y−は酸性染料のアニオンであり、R1、R2、R3、R4、R5、R6はそれぞれ独立にH又はC1〜C6の炭化水素基である。
S1、量子ドットで構成されるコアと、C6〜C22炭化水素基を含むアミンで構成されるシェルと、を有し、C6〜C22炭化水素基を含むアミンを結合した量子ドットを製造し、
S2、オニウム塩化試薬を用いて、量子ドットに結合したアミンをオニウム塩化し、アンモニウム塩基を含む量子ドットを形成し、
S3、アンモニウム塩基を含む量子ドットを酸性染料と造塩結合させ、改質量子ドットを得る。
[実施例a]
まず、以下のステップでアミノ基を含む量子ドットを合成する。
(1)CdOを0.177g、オレイン酸を1g、オクタデセンを2g秤量して、洗浄し乾燥させた3つ口フラスコに入れて、適切な大きさの磁子を加える。
(2)マグネットスターラが設けられた3つ口フラスコに窒素を注入してから、撹拌しつつ280℃まで昇温させ(250℃の時に、加えた原料が溶解し始める)、原料の溶融物が無色透明になるまで加熱する。
(3)50℃以下まで降温し、オクタデセンを8g加え、窒素の通気口を、真ん中の口に接続された凝縮パイプに切り換える。
(4)引き続き昇温し、温度が280℃に達したとき、予め混合しておいたSe 0.2607g、トリオクチルホスフィン(TOP)3g、オレイルアミン0.5gの混合溶液を針管で吸い上げ、吸い上げ前に窒素を2回吸入して空気を取り除き、必要があれば、適宜加熱して溶液が無色透明になるまでSeを溶解させ、さらに速やかに3つ口フラスコに注入し、反応10min後に溶液を抽出する。
(1)CdO粉末を1.284g(10mmol)秤量して三角フラスコに入れ、オレイン酸7.6mLと流動パラフィン17.4mLを加え、ゆるやかに150℃まで加熱し、暗赤色の前駆透明液体が形成されるまで維持する。
(2)Se粉末を0.079g(1.0mmol)秤量して4つ口フラスコに入れ、流動パラフィンを43mL加え、ゆるやかに220℃まで加熱し、鮮やかな黄色の前駆透明液体が形成するまで維持する。
(3)Cd前駆体溶液を5mL抽出し、速やかにSe前駆体溶液に注入し、オレイルアミンを2mL加えて高速攪拌する。溶液は急激にオレンジ色に変わる。
(4)温度を220℃に維持して量子ドットを徐々に成長させる。異なるタイミングで量子ドット溶液を2mL取り、冷トルエン3mLに加えることで、量子ドットの成長を阻止する。
重量パーセンテージが20%の酢酸溶液2000部に、上記アンモニウムイオンを有するCdSe量子ドットを65部加え、充分に攪拌混合した後、60℃まで加熱する。その後、予め調製されたC.I.アシッドレッド52の水溶液(10部のC.I.アシッドレッド52を90部の水に溶解する)を少量ずつ複数回に分けて上記量子ドット溶液に滴下する。滴下後に、60℃で120分間を攪拌し、十分に反応させる。反応液を濾紙に滴下し、浸透消失した時点を反応の終点とし、これにより、改質量子ドットを得たと判定できる。攪拌しながら室温まで放冷した後、吸引濾過して水洗し、その後、濾紙に残った改質量子ドットを乾燥機で乾燥して水分を除去し、改質量子ドットaを得る。
(1)まず、分光光度計を20分間予熱した後、試験ソフトで予備測定する。
(2)その後、2つのキュベットにn−ヘキサンを入れ、分光光度計に載置し、リミット検知を行う。試験スペクトルを380nm〜780nmに設置してから、測定する。
(3)測定終了後に、n−ヘキサンを入れたキュベットを改質量子ドット溶液を入れたキュベットに置き換え、試験を行う。試験終了後、試験結果を保存する。
(1)好ましくは、暗室の条件において、濃度が約0.01mg/mlの改質量子ドット溶液をキュベットに入れてから、このキュベットを機器に載置する。
(2)ソフトの試験スペクトルを380nm〜780nmに設置してから、試験を行い、結果を保存する。
具体的な合成方法及び合成ステップは実施例aと同一であり、相違点はオレイルアミンをドデシルアミンに置き換え、改質量子ドットbを得るという点である。
具体的な合成方法及び合成ステップは実施例aと同一であり、相違点はC.I.アシッドレッド52をC.I.アシッドレッド92に置き換え、改質量子ドットcを得るという点である。
1)顔料分散体の製造
表1に示す成分と用量に基づき、以下の方法を用いて顔料分散体PM−1〜PM−6をそれぞれ製造する。
実施例a、b、cで製造された改質量子ドットと上記で製造された顔料分散体を用いて、実施例1〜6の感光性樹脂組成物を製造する。
表2に示す着色剤、アルカリ可溶性樹脂、重合性モノマー、光重合開始剤、溶剤を混合して、感光性樹脂組成物を得る。このうち、アルカリ可溶性樹脂B1は新日鐵化学(株)製で、商品名V259MEとV301MEとの重量比が52.9:47.1の混合物であり、重合性モノマーは台湾長興化学製、光重合開始剤はBASF製、溶剤はダウケミカル製である。
表3に示す着色剤、アルカリ可溶性樹脂、重合性モノマー、光重合開始剤、溶剤を混合して、感光性樹脂組成物を得る。このうち、アルカリ可溶性樹脂B1は新日鐵化学(株)製で、商品名V259MEとV301MEとの重量比が52.9:47.1の混合物であり、重合性モノマーは台湾長興化学製、光重合開始剤はBASF製、溶剤はダウケミカル製である。
上記実施例と比較例において得た感光性樹脂組成物を10cm×10cmのガラス基板に塗布して約3μmの塗膜を得て、90℃で100sプリベークしてから、露光機(canon製 PLA−501F)を用いて50mj/cm2照度の紫外線をこの塗膜に照射し、その後、23℃で0.042重量%のKOH水溶液に浸漬して2min現像してから純水で洗浄し、再び230℃で30minベークすることで、ガラス基板に感光性樹脂層を形成し、カラーフィルタを得る。
1)感度
波長が365nm、強度が10mW/cm2の紫外線を、最小精度が3μmのパターン膜に照射してから、0.042重量%のKOH水溶液を用いて23℃で40s現像し、その後純水で1min洗浄する。
2)解像度
上記感度測定時に形成されたパターン膜の最小サイズを測定する
3)透過率
透過率の評価は分光光度計を用いてパターン膜の400nmでの透過率を測定する。
4)塗膜耐熱性試験
透明基板にレジスト材料を塗布し、塗膜の乾燥膜厚を約2.5μmにし、所定のパターンを有するマスクを用いて紫外線露光を行ってから現像し、未硬化部分を除去し、所望のパターンを形成する。その後、オーブンにて230℃で20分間加熱し、冷却後、顕微色度測定機(LCF−100M、大塚電子株式会社製)を用いて、得られた色度1(L*(1),a*(1),b*(1))を測定する。このほか、耐熱試験として、これをオーブンに置いて再度250℃で1時間加熱し、C光源下での色度2(L*(2),a*(2),b*(2))を測定する。
以下の式によって、測定された色差値で色差ΔEab*を算出し、以下の評価基準に沿って塗膜の耐熱性を評価する。
塗膜耐熱性試験と同一の方法で試験用基板を製造し、顕微色度測定機(CFT−02)を用いて色度1(L*(1),a*(1),b*(1))を測定する。その後、基板を自然光下に500時間放置する。基板を取り出した後、C光源下での色度2(L*(2),a*(2),b*(2))を測定し、塗膜耐熱性試験と同様に色差ΔEab*を算出し、耐熱性と同一の基準に沿って塗膜の耐光性を評価する。
Claims (18)
- 前記量子ドットは赤色の光を発生させる量子ドットであり、前記酸性染料は赤色の酸性染料であることを特徴とする、請求項1に記載の改質量子ドット。
- 前記赤色の光を発生させる量子ドットはCdSeであることを特徴とする、請求項2に記載の改質量子ドット。
- 前記C6〜C22炭化水素基を含むアミンはオレイルアミンであることを特徴とする、請求項1に記載の改質量子ドット。
- 請求項1〜3のいずれか一項に記載の改質量子ドットを含むことを特徴とする着色剤。
- 改質量子ドットと、
顔料、分散剤、分散樹脂及び溶剤を含む顔料分散体と、
を混合してなることを特徴とする、請求項5に記載の着色剤。 - 前記顔料、分散剤、分散樹脂及び溶剤がそれぞれ顔料分散体に占める重量パーセンテージは順に5〜30%、1%〜10%、1%〜10%、60〜90%であることを特徴とする、請求項6に記載の着色剤。
- 前記改質量子ドットにおける量子ドットは赤色の光を発生させる量子ドットであり、前記酸性染料は赤色の酸性染料であることを特徴とする、請求項5に記載の着色剤。
- 赤色の光を発生させる量子ドットはCdSeであることを特徴とする、請求項6に記載の着色剤。
- 請求項5〜9のいずれか一項に記載の着色剤を含むことを特徴とする感光性樹脂組成物。
- アルカリ可溶性樹脂、モノマー、開始剤、溶剤をさらに含み、
前記着色剤、アルカリ可溶性樹脂、モノマー及び開始剤の総和が前記感光性樹脂組成物に占める重量パーセンテージは10〜40%であり、溶剤が前記感光性樹脂組成物に占める重量パーセンテージは60〜90%であることを特徴とする、請求項10に記載の感光性樹脂組成物。 - 着色剤、アルカリ可溶性樹脂、モノマー及び開始剤がこれらの総量に占める重量パーセンテージは順に10〜80%、5〜60%、5〜60%、0.1〜20%であることを特徴とする、請求項11に記載の感光性樹脂組成物。
- 着色剤、アルカリ可溶性樹脂、モノマー及び開始剤がこれらの総量に占める重量パーセンテージは順に30〜60%、10〜30%、10〜30%、1〜10%であることを特徴とする、請求項12に記載の感光性樹脂組成物。
- 請求項10〜13のいずれか一項に記載の感光性樹脂組成物で製造されるカラーフィルタ。
- 請求項14に記載のカラーフィルタを含む表示装置。
- C6〜C22炭化水素基を含むアミンを結合した量子ドットを製造し、
オニウム塩化試薬を用いて前記量子ドットをオニウム塩化して、アンモニウム塩基を含む量子ドットを形成し、
前記アンモニウム塩基を含む量子ドットを酸性染料と反応させて造塩し、改質量子ドットを得ることを含むことを特徴とする改質量子ドットの製造方法。 - アンモニウム塩基を含む量子ドットのアミン値は10〜200mgKOH/gであることを特徴とする、請求項16に記載の改質量子ドットの製造方法。
- アンモニウム塩基を含む量子ドットのアミン値は20〜130mgKOH/gであることを特徴とする、請求項17に記載の改質量子ドットの製造方法。
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WO2020148912A1 (ja) * | 2019-01-18 | 2020-07-23 | シャープ株式会社 | 発光素子および電界発光装置並びに発光素子の製造方法 |
WO2022044761A1 (ja) * | 2020-08-31 | 2022-03-03 | 三菱ケミカル株式会社 | 半導体ナノ粒子含有組成物、カラーフィルタ、及び画像表示装置 |
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CN104479680B (zh) | 2016-09-28 |
WO2016095657A1 (zh) | 2016-06-23 |
US20160362602A1 (en) | 2016-12-15 |
EP3235893A1 (en) | 2017-10-25 |
KR20170008257A (ko) | 2017-01-23 |
KR101886948B1 (ko) | 2018-08-08 |
JP6671307B2 (ja) | 2020-03-25 |
EP3235893A4 (en) | 2018-07-25 |
CN104479680A (zh) | 2015-04-01 |
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