JP2020126822A - 感光性樹脂組成物、有機el素子隔壁、及び有機el素子 - Google Patents
感光性樹脂組成物、有機el素子隔壁、及び有機el素子 Download PDFInfo
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- JP2020126822A JP2020126822A JP2019098601A JP2019098601A JP2020126822A JP 2020126822 A JP2020126822 A JP 2020126822A JP 2019098601 A JP2019098601 A JP 2019098601A JP 2019098601 A JP2019098601 A JP 2019098601A JP 2020126822 A JP2020126822 A JP 2020126822A
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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Abstract
Description
[1]
バインダー樹脂(A)、
分子量が260〜5000であり、フェノール性水酸基当量が80〜155である、フェノール性水酸基を有する化合物(B)、
感放射線化合物(C)、及び
黒色染料及び黒色顔料からなる群より選択される着色剤(D)
を含む、有機EL素子隔壁用感光性樹脂組成物。
[2]
前記フェノール性水酸基を有する化合物(B)の分子量が、270〜4000である、[1]に記載の感光性樹脂組成物。
[3]
前記フェノール性水酸基を有する化合物(B)が、トリス(4−ヒドロキシフェニル)メタン、1,1,1−トリス(4−ヒドロキシフェニル)エタン、α,α,α’−トリス(4−ヒドロキシフェニル)−1−エチル−4−イソプロピルベンゼン、フェノールノボラック樹脂、クレゾールノボラック樹脂、ナフタレンジオール型フェノール樹脂、サリチルアルデヒド型フェノール樹脂、トリフェニルメタン型フェノール樹脂、及びビフェニルアラルキル型フェノール樹脂から選択される少なくとも1つである、[1]又は[2]のいずれかに記載の感光性樹脂組成物。
[4]
前記バインダー樹脂(A)、前記フェノール性水酸基を有する化合物(B)、前記感放射線化合物(C)及び前記着色剤(D)の合計100質量部を基準として、0.1質量部〜20質量部の前記フェノール性水酸基を有する化合物(B)を含む、[1]〜[3]のいずれかに記載の感光性樹脂組成物。
[5]
前記感放射線化合物(C)が、キノンジアジド化合物、スルホニウム塩、ホスホニウム塩、ジアゾニウム塩、及びヨードニウム塩からなる群より選択される少なくとも1種の光酸発生剤である、[1]〜[4]のいずれかに記載の感光性樹脂組成物。
[6]
前記バインダー樹脂(A)がアルカリ可溶性官能基を有する、[1]〜[5]のいずれかに記載の感光性樹脂組成物。
[7]
前記バインダー樹脂(A)、前記フェノール性水酸基を有する化合物(B)、前記感放射線化合物(C)及び前記着色剤(D)の合計100質量部を基準として、1質量部〜70質量部の前記着色剤(D)を含む、[1]〜[6]のいずれかに記載の感光性樹脂組成物。
[8]
前記バインダー樹脂(A)、前記フェノール性水酸基を有する化合物(B)、前記感放射線化合物(C)及び前記着色剤(D)の合計100質量部を基準として、5質量部〜50質量部の前記感放射線化合物(C)としての光酸発生剤を含む、[1]〜[7]のいずれかに記載の感光性樹脂組成物。
[9]
前記感光性樹脂組成物の硬化被膜の光学濃度(OD値)が膜厚1μmあたり0.5以上である、[1]〜[8]のいずれかに記載の感光性樹脂組成物。
[10]
前記バインダー樹脂(A)が、
(a)式(1)
の構造単位を有するポリアルケニルフェノール樹脂、
(b)式(3)
で表される構造単位を有するヒドロキシポリスチレン樹脂誘導体、
(c)エポキシ基及びフェノール性水酸基を有するアルカリ水溶液可溶性樹脂、及び
(d)アルカリ可溶性官能基を有する重合性単量体とその他の重合性単量体のアルカリ水溶液可溶性共重合体
からなる群より選択される少なくとも1種を含有する、[1]〜[9]のいずれかに記載の感光性樹脂組成物。
[11]
前記バインダー樹脂(A)が、
(c)エポキシ基及びフェノール性水酸基を有するアルカリ水溶液可溶性樹脂、及び
(d)アルカリ可溶性官能基を有する重合性単量体とその他の重合性単量体のアルカリ水溶液可溶性共重合体
からなる群より選択される少なくとも1種を含有する、[10]に記載の感光性樹脂組成物。
[12]
[1]〜[11]のいずれかに記載の感光性樹脂組成物の硬化物を含む有機EL素子隔壁。
[13]
[1]〜[11]のいずれかに記載の感光性樹脂組成物の硬化物を含む有機EL素子。
バインダー樹脂(A)は特に限定されないが、アルカリ可溶性官能基を有し、アルカリ可溶性であることが好ましい。アルカリ可溶性官能基としては、特に限定されないが、カルボキシ基、フェノール性水酸基、スルホ基、リン酸基、メルカプト基等が挙げられる。2種以上のアルカリ可溶性官能基を有するバインダー樹脂を使用してもよい。
(a)特定構造のポリアルケニルフェノール樹脂
(b)特定構造のヒドロキシポリスチレン樹脂誘導体
(c)エポキシ基及びフェノール性水酸基を有するアルカリ水溶液可溶性樹脂
(d)アルカリ可溶性官能基を有する重合性単量体とその他の重合性単量体のアルカリ水溶液可溶性共重合体
(e)ポリイミド樹脂
(f)ポリアミック酸樹脂
(g)ポリベンゾオキサゾール樹脂
(h)ポリベンゾオキサゾール樹脂前駆体
(i)シリコーン樹脂
(j)環状オレフィンポリマー
(k)カルド樹脂
ポリアルケニルフェノール樹脂(a)は、公知のフェノール樹脂の水酸基をアルケニルエーテル化し、さらにアルケニルエーテル基をクライゼン転位することにより得ることができる。中でも、式(1)
バインダー樹脂(A)として、式(3)
バインダー樹脂(A)として、エポキシ基及びフェノール性水酸基を有するアルカリ水溶液可溶性樹脂(c)を使用することもできる。このようなアルカリ水溶液可溶性樹脂は、例えば、1分子中に少なくとも2個のエポキシ基を有する化合物(以下、「エポキシ化合物」と表記することがある。)のエポキシ基と、ヒドロキシ安息香酸化合物のカルボキシ基を反応させることで得ることができる。アルカリ水溶液可溶性樹脂がエポキシ基を有することで、加熱時にフェノール性水酸基との反応により架橋を形成し、被膜の耐薬品性、耐熱性などを向上させることができる。フェノール性水酸基は現像時のアルカリ水溶液に対する可溶性に寄与する。
バインダー樹脂(A)として、アルカリ可溶性官能基を有する重合性単量体とその他の重合性単量体のアルカリ水溶液可溶性共重合体(d)を使用することができる。アルカリ可溶性官能基としては、カルボキシ基、アルコール性水酸基、フェノール性水酸基、スルホ基、リン酸基、酸無水物基等を挙げることができる。重合性単量体が有する重合性官能基としては、ラジカル重合性官能基を挙げることができ、例えば、CH2=CH−、CH2=C(CH3)−、CH2=CHCO−、CH2=C(CH3)CO−、−OC−CH=CH−CO−などが挙げられる。
で表される構造単位、及び式(11)
で表される構造単位を有する。
一実施態様では、バインダー樹脂(A)は、ポリイミド樹脂(e)、ポリアミック酸樹脂(f)、ポリベンゾオキサゾール樹脂(g)、及びポリベンゾオキサゾール樹脂前駆体(h)から選択される少なくとも一種である。ポリアミック酸樹脂(f)は、脱水閉環することによりポリイミド構造を有する樹脂となる。ポリベンゾオキサゾール樹脂前駆体(h)は、脱水閉環することによりポリベンゾオキサゾール樹脂(g)となる。
一実施態様では、バインダー樹脂(A)はシリコーン樹脂(i)を含む。シリコーン樹脂(i)は、式(15)で表されるオルガノシラン及び式(16)で表されるオルガノシランから選択される少なくとも1種の化合物を加水分解縮合することによって合成することができる。式(15)及び式(16)で表されるオルガノシランを用いることにより、感度及び解像度に優れた感光性樹脂組成物を得ることができる。
一実施態様では、バインダー樹脂(A)は、環状オレフィンポリマー(j)を含む。環状オレフィンポリマー(j)は、脂環構造とエチレン性不飽和二重結合とを有する環状オレフィン単量体の単独重合体又は共重合体である。環状オレフィンポリマー(j)は、環状オレフィン単量体以外の単量体に由来する構造単位を有してもよい。
一実施態様では、バインダー樹脂(A)は、カルド樹脂(k)を含む。カルド樹脂(k)は、カルド構造、すなわち、環状構造を構成する四級炭素原子に別の2つの環状構造が結合した骨格構造を有する。環状構造を構成する四級炭素原子に別の2つの環状構造が結合した骨格構造としては、例えば、フルオレン骨格、ビスフェノールフルオレン骨格、ビスアミノフェニルフルオレン骨格、エポキシ基を有するフルオレン骨格、アクリル基を有するフルオレン骨格などが挙げられる。カルド構造の例として、フルオレン環にベンゼン環が結合したものが挙げられる。
フェノール性水酸基を有する化合物(B)は、分子量が260〜5000であり、フェノール性水酸基当量が80〜155である。本開示において、フェノール性水酸基を有する化合物がオリゴマー又はポリマーである場合、それらの分子量とは、ゲルパーミエーションクロマトグラフィー(GPC:gel permeation chromatography)によって測定される、標準ポリスチレン換算値である重量平均分子量を意味する。フェノール性水酸基当量は、分子量又は重量平均分子量を1分子あたりのフェノール性水酸基の個数(オリゴマー又はポリマーの場合は平均個数)で割ったものである。フェノール性水酸基を有する化合物(B)は、1種類のみで用いることもでき、2種以上を組み合わせて用いてもよい。
感放射線化合物(C)として、光酸発生剤、光塩基発生剤又は光重合開始剤を用いることができる。光酸発生剤は可視光、紫外光、γ線、電子線などの放射線が照射されると酸を発生する化合物である。光酸発生剤は、放射線が照射された部分のアルカリ水溶液に対する溶解性を増大させることから、その部分が溶解するポジ型感光性樹脂組成物に使用することができる。光塩基発生剤は放射線が照射されると塩基を発生する化合物である。光塩基発生剤は、放射線が照射された部分のアルカリ水溶液に対する溶解性を低下させることから、その部分が不溶化するネガ型感光性樹脂組成物に使用することができる。光重合開始剤は放射線が照射されるとラジカルを発生する化合物である。光重合開始剤は、感光性樹脂組成物がラジカル重合性官能基を有するバインダー樹脂又はラジカル重合性化合物を含む場合に、放射線が照射された部分のバインダー樹脂のラジカル重合官能基又はラジカル重合性化合物のラジカル重合が進行して、その部分にアルカリ水溶液に対して不溶性の重合物が形成される、ネガ型感光性樹脂組成物に使用することができる。
着色剤(D)は黒色染料及び黒色顔料からなる群より選択される。黒色染料と黒色顔料とを併用してもよい。着色剤(D)を含む感光性樹脂組成物を用いて有機EL素子に黒色の隔壁を形成することにより、有機ELディスプレイ等の表示装置の視認性を向上させることができる。
感光性樹脂組成物は任意成分として、熱硬化剤、界面活性剤、(D)以外の着色剤等を含むことができる。任意成分(E)は(A)〜(D)のいずれにも当てはまらないものと定義する。
感光性樹脂組成物は、溶媒に溶解されて溶液状態(但し、黒色顔料を含むときは、顔料は分散状態である。)で用いることができる。例えば、バインダー樹脂(A)を溶媒(F)に溶解して得られた溶液に、フェノール性水酸基を有する化合物(B)、感放射線化合物(C)、着色剤(D)、必要に応じて熱硬化剤、界面活性剤等の任意成分(E)を所定の割合で混合することにより、溶液状態の感光性樹脂組成物を調製することができる。感光性樹脂組成物は、溶媒の量を変化させることにより使用する塗布方法に適した粘度に調整することができる。
装置名:Shodex(登録商標)GPC−101
カラム:Shodex(登録商標)LF−804
移動相:テトラヒドロフラン
流速:1.0mL/分
検出器:Shodex(登録商標)RI−71
温度:40℃
300mLの3つ口型フラスコに溶媒としてγ−ブチロラクトン(三菱ケミカル株式会社製)75.2g、1分子中に少なくとも2個のエポキシ基を有する化合物としてEPICLON(登録商標)N−770(DIC株式会社製フェノールノボラック型エポキシ樹脂、エポキシ当量188)を37.6g仕込み、窒素ガス雰囲気下、60℃で溶解させた。そこへヒドロキシ安息香酸化合物として3,5−ジヒドロキシ安息香酸(富士フイルム和光純薬株式会社製)を20.1g(エポキシ1当量に対して0.65当量)、反応触媒としてトリフェニルホスフィン(東京化成工業株式会社製)を0.173g(0.660mmol)追加し、110℃で21時間反応させた。反応溶液を室温に戻し、γ−ブチロラクトンで固形分20質量%に希釈し、溶液をろ過して197.7gの樹脂液cを得た。得られた反応物の数平均分子量は2400、重量平均分子量は8300であった。
4−ヒドロキシフェニルメタクリレート(昭和電工株式会社製「PQMA」)28.0g、及びN−シクロヘキシルマレイミド(株式会社日本触媒製)7.89gを、1−メトキシ−2−プロピルアセテート(株式会社ダイセル製)77.1gに、重合開始剤としてV−601(富士フイルム和光純薬株式会社製)3.66gを、1−メトキシ−2−プロピルアセテート(株式会社ダイセル製)14.6gにそれぞれ完全に溶解させた。得られた2つの溶液を、300mLの3つ口型フラスコ中、窒素ガス雰囲気下で85℃に加熱した1−メトキシ−2−プロピルアセテート(株式会社ダイセル製)61.2gに同時に2時間かけて滴下し、その後85℃で3時間反応させた。室温まで冷却した反応溶液を815gのトルエン中に滴下し、共重合体を沈殿させた。沈殿した共重合体をろ過により回収し、90℃で4時間真空乾燥し白色の粉体を32.4g回収した。これをγ−ブチロラクトンに溶解し、固形分20質量%の樹脂液dを得た。得られた反応物の数平均分子量は6100、重量平均分子量は11800であった。
バインダー樹脂(A)
バインダー樹脂(A)として表1に示す樹脂を使用した。
フェノール性水酸基を有する化合物(B)又は比較例の化合物として表2に示す化合物を使用した。フェノール性水酸基当量は、分子量又は重量平均分子量を1分子あたりのフェノール性水酸基の個数(オリゴマー又はポリマーの場合は平均個数)で割ったものである。
ポジ型については、光酸発生剤であるキノンジアジド化合物TPPA(4)−150DF(α,α,α’−トリス(4−ヒドロキシフェニル)−1−エチル−4−イソプロピルベンゼンの1,2−ナフトキノンジアジド−4−スルホン酸エステル、東洋合成工業株式会社製)、又はキノンジアジド化合物TS−150A(α,α,α’−トリス(4−ヒドロキシフェニル)−1−エチル−4−イソプロピルベンゼンの1,2−ナフトキノンジアジド−5−スルホン酸エステル(東洋合成工業株式会社製)を使用した。ネガ型については、光カチオン重合開始剤であるCPI−200K(トリアリールスルホニウム・特殊リン系アニオン塩のプロピレンカーボネート溶液、サンアプロ株式会社製)を使用した。TS−150Aの構造を以下に示す。TS−150Aのスルホン酸エステル化率は約50%であった。
着色剤として、黒色染料であるVALIFAST(登録商標)BLACK 3804(ソルベントブラック34のC.I.で規定される黒色染料、オリエント化学工業株式会社製)又は黒色顔料であるチタンブラック13M(三菱マテリアル電子化成株式会社製)を使用した。
界面活性剤(レベリング剤)としてメガファック(登録商標)F−559(フッ素系界面活性剤、DIC株式会社製)を使用した。
溶媒としてγ−ブチロラクトン(GBL)及びプロピレングリコールモノメチルエーテルアセテート(PGMEA)の混合溶媒(GBL:PGMEA=40:60(質量比))を使用した。
実施例及び比較例で使用した評価方法は以下のとおりである。
ガラス基板(大きさ100mm×100mm×1mm)に感光性樹脂組成物を乾燥膜厚が約1.5μmになるようにバーコートし、ホットプレート上120℃で80秒加熱し溶媒を乾燥した。超高圧水銀ランプを組み込んだ露光装置(商品名マルチライトML−251A/B、ウシオ電機株式会社製)で水銀露光用バンドパスフィルター(商品名HB0365、朝日分光株式会社製)と石英製のフォトマスク(5μm、10μm、20μm、50μm、100μm、200μm、500μmのライン&スペース(L/S)パターンを有するもの)を介して100mJ/cm2で露光した。露光量は紫外線積算光量計(商品名UIT−150 受光部 UVD−S365、ウシオ電機株式会社製)を用いて測定した。露光した被膜は、スピン現像装置(AD−1200、滝沢産業株式会社製)を用い2.38質量%水酸化テトラメチルアンモニウム水溶液で60秒間アルカリ現像を行なった。その後、窒素ガス雰囲気下250℃で60分硬化させることによりパターンサンプルを得た。
ガラス基板(大きさ100mm×100mm×1mm)に感光性樹脂組成物を乾燥膜厚が約1.5μmになるようにバーコートし、ホットプレート上120℃で80秒加熱し溶媒を乾燥した。乾燥膜厚を光学式膜厚測定装置(F20−NIR、フィルメトリクス株式会社製)を用いて測定後、スピン現像装置(AD−1200、滝沢産業株式会社製)を用い2.38質量%水酸化テトラメチルアンモニウム水溶液で60秒間アルカリ現像を行なった。アルカリ現像後の膜厚を再び光学式膜厚測定装置(F20−NIR、フィルメトリクス株式会社製)を用いて測定し、現像前後で溶解した膜厚(μm)を未露光部溶解性として算出した。
ガラス基板(大きさ100mm×100mm×1mm)に感光性樹脂組成物を乾燥膜厚が約1.5μmになるようにスピンコートし、ホットプレート上120℃で80秒加熱し溶媒を乾燥した。その後、窒素ガス雰囲気下250℃で60分硬化させることにより被膜を得た。硬化後の被膜のOD値を透過濃度計(BMT−1、サカタインクスエンジニアリング株式会社製)で測定し、ガラスのみのOD値で補正を行って、被膜の厚さ1μm当たりのOD値に換算した。被膜の厚みは光学式膜厚測定装置(F20−NIR、フィルメトリクス株式会社製)を用いて測定した。
[実施例1〜6、比較例1〜7]
樹脂液c 24質量部(固形分換算)及び樹脂液d 21質量部(固形分換算)を混合して溶解し、得られた溶液に、表2に記載のフェノール性水酸基を有する化合物(B) 5質量部、キノンジアジド化合物TPPA(4)−150DF 21質量部、VALIFAST(登録商標)BLACK 3804 29質量部、メガファック(登録商標)F−559 0.14質量部、及びGBL/PGMEA混合溶媒を加えて、さらに混合した。成分が溶解したことを目視で確認した後、孔径0.22μmのミリポアフィルターで濾過し、固形分濃度12質量%の感光性樹脂組成物を調製した。
表4に示す組成で実施例1と同様に感光性樹脂組成物を調製した。実施例1及び調製した感光性樹脂組成物について、加熱後OD値、残渣、パターンクリア膜厚、未露光部溶解性、及びクラックの評価を行った。結果を表4に示す。表4における組成の質量部は固形分換算値である。
Claims (13)
- バインダー樹脂(A)、
分子量が260〜5000であり、フェノール性水酸基当量が80〜155である、フェノール性水酸基を有する化合物(B)、
感放射線化合物(C)、及び
黒色染料及び黒色顔料からなる群より選択される着色剤(D)
を含む、有機EL素子隔壁用感光性樹脂組成物。 - 前記フェノール性水酸基を有する化合物(B)の分子量が、270〜4000である、請求項1に記載の感光性樹脂組成物。
- 前記フェノール性水酸基を有する化合物(B)が、トリス(4−ヒドロキシフェニル)メタン、1,1,1−トリス(4−ヒドロキシフェニル)エタン、α,α,α’−トリス(4−ヒドロキシフェニル)−1−エチル−4−イソプロピルベンゼン、フェノールノボラック樹脂、クレゾールノボラック樹脂、ナフタレンジオール型フェノール樹脂、サリチルアルデヒド型フェノール樹脂、トリフェニルメタン型フェノール樹脂、及びビフェニルアラルキル型フェノール樹脂から選択される少なくとも1つである、請求項1又は2のいずれかに記載の感光性樹脂組成物。
- 前記バインダー樹脂(A)、前記フェノール性水酸基を有する化合物(B)、前記感放射線化合物(C)及び前記着色剤(D)の合計100質量部を基準として、0.1質量部〜20質量部の前記フェノール性水酸基を有する化合物(B)を含む、請求項1〜3のいずれか一項に記載の感光性樹脂組成物。
- 前記感放射線化合物(C)が、キノンジアジド化合物、スルホニウム塩、ホスホニウム塩、ジアゾニウム塩、及びヨードニウム塩からなる群より選択される少なくとも1種の光酸発生剤である、請求項1〜4のいずれか一項に記載の感光性樹脂組成物。
- 前記バインダー樹脂(A)がアルカリ可溶性官能基を有する、請求項1〜5のいずれか一項に記載の感光性樹脂組成物。
- 前記バインダー樹脂(A)、前記フェノール性水酸基を有する化合物(B)、前記感放射線化合物(C)及び前記着色剤(D)の合計100質量部を基準として、1質量部〜70質量部の前記着色剤(D)を含む、請求項1〜6のいずれか一項に記載の感光性樹脂組成物。
- 前記バインダー樹脂(A)、前記フェノール性水酸基を有する化合物(B)、前記感放射線化合物(C)及び前記着色剤(D)の合計100質量部を基準として、5質量部〜50質量部の前記感放射線化合物(C)としての光酸発生剤を含む、請求項1〜7のいずれか一項に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物の硬化被膜の光学濃度(OD値)が膜厚1μmあたり0.5以上である、請求項1〜8のいずれか一項に記載の感光性樹脂組成物。
- 前記バインダー樹脂(A)が、
(a)式(1)
の構造単位を有するポリアルケニルフェノール樹脂、
(b)式(3)
で表される構造単位を有するヒドロキシポリスチレン樹脂誘導体、
(c)エポキシ基及びフェノール性水酸基を有するアルカリ水溶液可溶性樹脂、及び
(d)アルカリ可溶性官能基を有する重合性単量体とその他の重合性単量体のアルカリ水溶液可溶性共重合体
からなる群より選択される少なくとも1種を含有する、請求項1〜9のいずれか一項に記載の感光性樹脂組成物。 - 前記バインダー樹脂(A)が、
(c)エポキシ基及びフェノール性水酸基を有するアルカリ水溶液可溶性樹脂、及び
(d)アルカリ可溶性官能基を有する重合性単量体とその他の重合性単量体のアルカリ水溶液可溶性共重合体
からなる群より選択される少なくとも1種を含有する、請求項10に記載の感光性樹脂組成物。 - 請求項1〜11のいずれか一項に記載の感光性樹脂組成物の硬化物を含む有機EL素子隔壁。
- 請求項1〜11のいずれか一項に記載の感光性樹脂組成物の硬化物を含む有機EL素子。
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US11650499B2 (en) | 2023-05-16 |
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JP6689434B1 (ja) | 2020-04-28 |
US20200249572A1 (en) | 2020-08-06 |
CN111538209B (zh) | 2024-05-14 |
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TW202030901A (zh) | 2020-08-16 |
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