JP6891880B2 - 感光性樹脂組成物、硬化膜、硬化膜を具備する素子、硬化膜を具備する有機el表示装置、硬化膜の製造方法、および有機el表示装置の製造方法 - Google Patents
感光性樹脂組成物、硬化膜、硬化膜を具備する素子、硬化膜を具備する有機el表示装置、硬化膜の製造方法、および有機el表示装置の製造方法 Download PDFInfo
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- JP6891880B2 JP6891880B2 JP2018515696A JP2018515696A JP6891880B2 JP 6891880 B2 JP6891880 B2 JP 6891880B2 JP 2018515696 A JP2018515696 A JP 2018515696A JP 2018515696 A JP2018515696 A JP 2018515696A JP 6891880 B2 JP6891880 B2 JP 6891880B2
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- 239000001257 hydrogen Substances 0.000 claims description 4
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
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- 238000003848 UV Light-Curing Methods 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
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- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 4
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- UWGCNDBLFSEBDW-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]naphthalene-2,7-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 UWGCNDBLFSEBDW-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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Description
1/Tgp = Σ(Wn/Tgn)
ここで、各単量体の単独重合体としたときのガラス転移温度Tgn(K)は、文献またはメーカーのカタログ値が存在する場合にはその値を採用し、存在しない場合にはJIS K7121:2012「プラスチックの転移温度測定方法」に準拠して示差走査熱量測定(DSC)によって測定された値を採用する。
pは3または4の整数を表す。
硬化膜の製造方法は、
(1)上述した感光性樹脂組成物を基板に塗布し、感光性樹脂膜を形成する工程、
(2)該感光性樹脂膜を乾燥する工程、
(3)乾燥した感光性樹脂膜にフォトマスクを介して露光する工程、
(4)露光した感光性樹脂膜を現像する工程および
(5)現像した感光性樹脂膜を加熱処理する工程
とを含む。
1.0≦(TFT)≦5.0 (α)
0.2≦(THT)≦4.0 (β)
0.5≦(ΔTFT−HT)≦4.0 (γ)
厚膜部の膜厚(TFT)は、1.0μm以上が好ましく、1.2μm以上がより好ましく、1.5μm以上がさらに好ましく、1.7μm以上が特に好ましく、2.0μm以上が最も好ましい。厚膜部の膜厚(TFT)が上記範囲内であると、薄膜部との膜厚差を確保しやすい。一方、厚膜部の膜厚(TFT)は、5.0μm以下が好ましく、4.5μm以下がより好ましく、4.0μm以下がさらに好ましく、3.5μm以下が特に好ましく、3.0μm以下が最も好ましい。厚膜部の膜厚(TFT)が上記範囲内であると、感光性樹脂膜の膜厚を薄くできることから、露光量を低減でき、タクトタイム短縮が可能となる。
実施例で用いた樹脂(P1)〜(P4)の分子量は、GPC(ゲルパーミエーションクロマトグラフィー)装置Waters2690−996(日本ウォーターズ(株)製)を用い、展開溶媒をN−メチル−2−ピロリドン(以降NMPと呼ぶ)として測定し、ポリスチレン換算で数平均分子量(Mn)を算出した。
表面粗さ・輪郭形状測定機(SURFCOM1400D;(株)東京精密)を用いて、測定倍率を10,000倍、測定長さを1.0mm、測定速度を0.30mm/sとして、プリベーク後、現像後およびキュア後の膜厚を測定した。
各実施例の感光性樹脂組成物をOA−10ガラス板(日本電気硝子(株)製)上にスピンコート法により任意の回転数で塗布し感光性樹脂膜を得て、乾燥工程として100℃のホットプレート上で2分間プリベークし、膜厚3.5μmの感光性樹脂膜を得た。次に両面アライメント片面露光装置(マスクアライナー PEM−6M;ユニオン光学(株)製)を用い、感度測定用のグレースケールマスク(フォトマスク)を介し、超高圧水銀灯のi線(波長365nm)、h線(波長405nm)及びg線(波長436nm)でパターン露光した。その後、露光した感光性樹脂膜を自動現像装置(滝沢産業(株)製AD−2000)を用いて2.38質量%水酸化テトラメチルアンモニウム水溶液で90秒間シャワー現像し、次いで純水で30秒間リンスした。前記の方法で得た現像した感光性樹脂膜のパターンを、FDP顕微鏡MX61(オリンパス(株)社製)を用いて倍率50倍で観察し、20μmのライン・アンド・スペースパターンを1対1の幅に形成する露光量(これを最適露光量という)を求め、これを感度とした。
(3)感度評価で得られた現像した感光性樹脂膜付き基板を窒素雰囲気下250℃のオーブン中で60分間キュア(加熱処理)して硬化膜を得た。得られた硬化膜の20μmパターンラインについて、断面形状を走査型電子顕微鏡(日立製作所(株)製、「S−4800型」)を用いて観察し、図4における基板17と絶縁層18の斜面部分のなす角度のうち最大の角度をテーパー角θとして、θ値を計測した。
各実施例の感光性樹脂組成物をOA−10ガラス板(日本電気硝子(株)製)上にスピンコート法により任意の回転数で塗布し、100℃のホットプレート上で2分間プリベークし、膜厚3.5μmの膜を得た。次に両面アライメント片面露光装置(マスクアライナー PEM−6M;ユニオン光学(株)製)を用い、図3に示す透光部16及び遮光部15を有し、半透光部14の透過率が30%のハーフトーンフォトマスクを介し、超高圧水銀灯のi線(波長365nm)、h線(波長405nm)及びg線(波長436nm)で(3)感度評価で得られた最適露光量でパターン露光した。用いたハーフトーンフォトマスクの線幅は、半透光部14、遮光部15、透光部16がそれぞれ12μmである。その後、自動現像装置(滝沢産業(株)製AD−2000)を用いて2.38質量%水酸化テトラメチルアンモニウム水溶液で90秒間シャワー現像し、次いで純水で30秒間リンスした。次に、得られた現像した感光性樹脂膜付き基板を窒素雰囲気下のオーブンで以下の3条件でそれぞれキュアした。
条件1:250℃/60分間
条件2:270℃/60分間
条件3:300℃/60分間
得られた硬化膜の断面形状を走査型電子顕微鏡(日立製作所(株)製、「S−4800型」)を用いて観察し、段差形状が得られ、薄膜部において基板に対する傾斜角が3°以下の領域が含まれているものを「良好」、キュア時のパターン流動により段差形状が失われ、薄膜部において基板に対する傾斜角が3°以下の領域が含まれていないものを「不良」と判断した。段差形状が得られた「良好」な例を図5に、段差形状が失われた「不良」な例を図6に示す。条件1〜3のすべてで「良好」なものをA、条件1,2のみ「良好」なものをB、条件1のみ「良好」なものをC、全条件で「不良」なものをDとして判定した。
(5)硬化膜の段差形状評価で条件1のキュアで得られた硬化膜において、厚膜部の膜厚(TFT)、薄膜部の膜厚(THT)および厚膜部と薄膜部との膜厚差(ΔTFT−HT)を(2)膜厚測定に記載の方法で測定した。ただし、(5)硬化膜の段差形状評価で「良好」な段差形状が得られた場合に限り、そうでない場合は測定不能とした。
(5)硬化膜の段差形状評価の硬化膜作製工程において、現像後の開口部のパターン寸法を(CDDEV)、条件1のキュア後の同一部分のパターン寸法を(CDCURE)とした場合、現像後とキュア後のパターン寸法変化量(CDDEV−CDCURE)を、FDP顕微鏡MX61(オリンパス(株)社製)を用いて倍率50倍で測定した。
(4)硬化膜の断面形状評価で得られた硬化膜の押込み弾性率を、超微小押し込み硬さ試験機ENT−2100((株)エリオニクス製)を用いて、以下の条件で測定数n=5で測定し、その平均値を算出した。
圧子形状:バーコビッチ
荷重速度:0.02mN/秒
最大試験荷重:0.1mN
最大試験荷重保持時間:10秒
除荷速度:0.02mN/秒
測定温度:25℃。
重量W0をあらかじめ測定した6インチシリコンウェハー上に、各実施例の感光性樹脂組成物をスピンコート法により任意の回転数で塗布し感光性樹脂膜付き基板を得て、乾燥工程として100℃のホットプレート上で2分間プリベークし、膜厚3.5μmの感光性樹脂膜付き基板を得た。次に得られた感光性樹脂膜付き基板を、両面アライメント片面露光装置(マスクアライナー PEM−6M;ユニオン光学(株)製)を用い、感度測定用のグレースケールマスク(フォトマスク)を介し、超高圧水銀灯のi線(波長365nm)、h線(波長405nm)及びg線(波長436nm)で(3)感度評価で得られた最適露光量で全面露光した。その後、露光した感光性樹脂膜付き基板を自動現像装置(滝沢産業(株)製AD−2000)を用いて2.38質量%水酸化テトラメチルアンモニウム水溶液で90秒間シャワー現像し、次いで純水で30秒間リンスした。次に、現像した感光性樹脂膜付き基板を窒素雰囲気下250℃のオーブン中で60分間キュア(加熱処理)して硬化膜付き基板を得た。得られた硬化膜付き基板の重量W1を測定した後、超純水中に23℃条件下で24時間浸漬させた。超純水中から取り出した後、硬化膜付き基板に付着した水分を十分に拭き取った後、重量W2を測定した。そして、以下の式(X)により吸水率(%)を求めた。
吸水率 = (W2−W1)/(W1−W0)×100 ・・・ 式(X)。
光学濃度計(361TVisual;X−Rite社製)を用いて、(5)硬化膜の段差形状評価の条件1(250℃/60分間)で得られた硬化膜の入射光及び透過光の強度をそれぞれ測定し、以下の式(Y)より遮光性OD値を算出した。
OD値 = log10(I0/I) ・・・ 式(Y)
I0:入射光強度
I:透過光強度。
<有機EL表示装置の作製方法>
図7に使用した有機EL表示装置の概略図を示す。まず、38×46mmの無アルカリガラス基板19に、スパッタ法によりITO透明導電膜10nmを基板全面に形成し、エッチングして、第一電極20を形成すると同時に、第二電極を取り出すための補助電極21も形成した。得られた基板を“セミコクリーン56”(商品名、フルウチ化学(株)製)で10分間超音波洗浄してから、超純水で洗浄した。次にこの基板全面に、各実施例に即した感光性樹脂組成物をスピンコート法により塗布し、100℃のホットプレート上で2分間プリベークして膜を形成した。この膜にフォトマスクを介してUV露光した後、2.38%TMAH水溶液で現像し、露光部分のみを溶解させた後、純水でリンスし、パターンを得た。得られたパターンを、窒素雰囲気下250℃のオーブン中で60分間キュアした。このようにして、幅70μm、長さ260μmの開口部が幅方向にピッチ155μm、長さ方向にピッチ465μmで配置され、それぞれの開口部が第一電極を露出せしめる形状の画素分割層22を、基板有効エリアに限定して形成した。なお、この開口部が最終的に発光画素となる。また、基板有効エリアは16mm四方、画素分割層の厚さは約1.0μmであった。
上述の方法で作製した有機EL表示装置を、10mA/cm2で直流駆動にて発光させ、非発光、輝度ムラ、発光面積の縮小などの発光特性異常がないか確認した。
上述の方法で作製した有機EL表示装置を、80℃で500時間保持する耐久性試験を実施した後、10mA/cm2で直流駆動にて発光させ、非発光、輝度ムラ、発光面積の縮小などの発光特性異常がないか確認した。
合成例1 ヒドロキシル基含有ジアミン化合物の合成
2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(以降BAHFと呼ぶ)18.3g(0.05モル)をアセトン100mL、プロピレンオキシド17.4g(0.3モル)に溶解させ、−15℃に冷却した。ここに3−ニトロベンゾイルクロリド20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、−15℃で4時間反応させ、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、BAHF58.6g(0.16モル)、末端封止剤として3−アミノフェノール8.7g(0.08モル)をN−メチル−2−ピロリドン(NMP)300gに溶解した。ここにODPA62.0g(0.20モル)をNMP100gとともに加えて、20℃で1時間撹拌し、次いで50℃で4時間撹拌した。その後、キシレンを15g添加し、水をキシレンとともに共沸しながら、150℃で5時間撹拌した。撹拌終了後、溶液を水5Lに投入して白色沈殿を集めた。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリイミド(P1)を得た。ポリイミド(P1)の数平均分子量は8200であった。
乾燥窒素気流下、3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物(以降ODPAと呼ぶ)62.0g(0.20モル)をN−メチル−2−ピロリドン(以降NMPと呼ぶ)500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物96.7g(0.16モル)をNMP100gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。次に末端封止剤として3−アミノフェノール8.7g(0.08モル)をNMP50gとともに加え、50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール47.7g(0.40モル)をNMP100gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水5Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリイミド前駆体(P2)を得た。ポリイミド前駆体(P2)の数平均分子量は11000であった。
乾燥窒素気流下、ジフェニルエーテル−4,4'−ジカルボン酸41.3g(0.16モル)、と1−ヒドロキシ−1,2,3−ベンゾトリアゾール43.2g(0.32モル)とを反応させて得られたジカルボン酸誘導体の混合物0.16モルとBAHF73.3g(0.20モル)をNMP570gに溶解させ、その後75℃で12時間反応させた。次にNMP70gに溶解させた5−ノルボルネン−2,3−ジカルボン酸無水物13.1g(0.08モル)を加え、更に12時間攪拌して反応を終了した。反応混合物を濾過した後、反応混合物を水/メタノール=3/1(容積比)の溶液に投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリベンゾオキサゾール(PBO)前駆体(P3)を得た。PBO前駆体(P3)の数平均分子量は8500であった。
公知の方法(特許第3120476号;実施例1)により、メチルメタクリレート/メタクリル酸/スチレン共重合体(質量比30/40/30)を合成した。該共重合体100質量部に対し、グリシジルメタクリレート40質量部を付加させ、精製水で再沈、濾過及び乾燥することにより、重量平均分子量(Mw)15000、酸価110(mgKOH/g)のラジカル重合性モノマーを含む重合体であるアクリル樹脂(P4)を得た。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)21.22g(0.05モル)と5−ナフトキノンジアジドスルホニル酸クロリド36.27g(0.135モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合したトリエチルアミン15.18gを、系内が35℃以上にならないように滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩を濾過し、ろ液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表される光酸発生剤を得た。
V259ME;カルド樹脂のPGMEA溶液(固形分濃度56.5質量%、新日鐵化学(株)製)。
ADDM;1,3−アダマンタンジメタクリレート(三菱ガス化学(株)製)単独重合体のTgは245[℃]、官能基数は2
DCP−A;“ライトアクリレート”(登録商標)DCP−A(ジメチロールトリシクロデカンジアクリレート、共栄社化学(株)製)単独重合体のTgは190[℃] 、官能基数は2
DCP−M;ライトエステルDCP−M(ジメチロールトリシクロデカンジメタクリレート、共栄社化学(株)製)、単独重合体のTgは214[℃] 、官能基数は2
DPCA−60;“KAYARAD”(登録商標)DPCA−60(ペンチレンカルボニル構造を分子内に6個有する、カプロラクトン変性ジペンタエリスリトールヘキサアクリレート、日本化薬(株)製)、単独重合体のTgは60[℃] 、官能基数は6
DPHA;“KAYARAD”(登録商標)DPHA(ジペンタエリスリトールヘキサアクリレート、日本化薬(株)製)、単独重合体のTgは80[℃] 、官能基数は6
M−315;“アロニックス”(登録商標)M−315(イソシアヌル酸エチレンオキシド変性トリアクリレート、東亞合成(株)製)、単独重合体のTgは272[℃] 、官能基数は3
PE−4A;“ライトアクリレート”(登録商標)PE−4A(ペンタエリスリトールテトラアクリレート、共栄社化学(株)製)、単独重合体のTgは103[℃] 、官能基数は4。
NCI−831:“アデカアークルズ”(登録商標)NCI−831(オキシムエステル系光重合開始剤、(株)ADEKA製)。
BLACK S0084;“IRGAPHOR”(登録商標) BLACK S0084(ペリレン系黒色顔料、BASF製)
BLACK S0100CF;“IRGAPHOR”(登録商標) BLACK S0100CF(ベンゾフラノン系黒色顔料、BASF製)
D.Y.201;C.I.ディスパースイエロー201(黄色染料)
P.B.15:6;C.I.ピグメントブルー15:6(青色顔料)
P.R.254;C.I.ピグメントレッド254(赤色顔料)
P.Y.139;C.I.ピグメントイエロー139(黄色顔料)
S.B.63;C.I.ソルベントブルー63(青色染料)
S.R.18;C.I.ソルベントレッド18(赤色染料)
TPK−1227;スルホン酸基を導入する表面処理がされたカーボンブラック(CABOT製)。
HMOM−TPHAP;(メトキシメチル基を6個有する化合物、本州化学工業(株)製)
MW−100−LM;“ニカラック”(登録商標)MW−100−LM(メトキシメチル基を6個有する化合物、日本カーバイド工業(株)製)
MX−270;“ニカラック”(登録商標)MX−270(メトキシメチル基を4個有する化合物、日本カーバイド工業(株)製)
VG3101L;“テクモア”(登録商標)VG3101L(エポキシ基を3個有する化合物、(株)プリンテック製)。
S−20000;“SOLSPERSE”(登録商標)20000(ポリエーテル系分散剤、Lubrizol製)。
GBL;γ−ブチロラクトン
MBA;3−メトキシブチルアセテート。
調製例1
アルカリ可溶性樹樹脂として、合成例2で得られた(P1)を33.3gに溶剤としてMBAを117g秤量して混合し、樹脂溶液を得た。この樹脂溶液に分散剤としてSOLSPERSE 20000を33.3g、溶剤としてMBAを828g、着色剤として、Irgaphor Black S0100CFを100g秤量して混合し、高速分散機(ホモディスパー 2.5型;プライミクス(株)製)を用いて20分攪拌し、予備分散液を得た。顔料分散用のセラミックビーズとして、直径0.30mmのジルコニア粉砕ボール(YTZ;東ソー(株)製)が75%充填された遠心分離セパレーターを具備する、ウルトラアペックスミル(UAM−015;寿工業(株)製)に、得られた予備分散液を供給し、ローター周速7.0m/sで3時間処理して、固形分濃度15質量%、着色剤/樹脂=60/40(質量比)の顔料分散液(Dsp−1)を得た。
調製例1と同様の方法で、化合物の種類と量は表1記載の通りで分散液Dsp−2〜8を得た。
黄色灯下、(A)アルカリ可溶性樹脂として合成例2で得られた(P1)を8.0g、(B)ラジカル重合性化合物としてDCP−Mを3.0gとDPCA−60を3.0g、(C)光重合開始剤としてNCI−831を1.5g、(E)熱架橋剤としてMW−100−LMを2.0g秤量し、これにMBA99.1g添加し、攪拌、溶解させて予備調合液を得た。次に、調製例1で得られた顔料分散液(Dsp−1)を66.7g秤量し、ここに、上記で得られた予備調合液を添加して攪拌し、均一溶液とした。ここで、秤量した顔料分散液(Dsp−1)に含まれる(A)アルカリ可溶性樹脂の(P1)は2.0g、(D)着色剤のBLACK S0100CFは6.0g、(F)分散剤のS−20000は2.0g、MBAは56.7gである。その後、得られた溶液を孔径1μmのフィルターでろ過し、感光性樹脂組成物Aを得た。得られた感光性樹脂組成物を用い、上述(3)〜(10)の評価を実施した。
実施例1と同様の方法で、化合物の種類と量は表2〜4に記載の通りで感光性樹脂組成物B〜P、R〜U、感光性樹脂組成物a〜dを得た。得られた感光性樹脂組成物を用い、上述(3)〜(10)の評価を実施した。
黄色灯下、(A)アルカリ可溶性樹脂として合成例2で得られた(P1)を10.0g、(B)ラジカル重合性化合物としてDCP−Mを3.0gとDPCA−60を3.0g、(C)光重合開始剤としてNCI−831を1.5g、(D)着色剤として染料のS.B.63を3.0g、S.R.18を2.0g、D.Y.201を1.0g、(E)熱架橋剤としてMW−100−LMを2.0g秤量し、これにGBL144.5gを添加し、攪拌、溶解させた。その後、得られた溶液を孔径1μmのフィルターでろ過し、感光性樹脂組成物Qを得た。得られた感光性樹脂組成物を用い、上述(3)〜(10)の評価を実施した。
黄色灯下、(A)アルカリ可溶性樹脂として合成例2で得られた(P1)を10.0g、(D)着色剤として染料のS.B.63を3.0g、S.R.18を2.0g、D.Y.201を1.0g、(E)熱架橋剤としてMW−100−LMを2.0g、さらに合成例6で得られた光酸発生剤を1.5g秤量し、これにGBL102.0gを添加し、攪拌、溶解させた。その後、得られた溶液を孔径1μmのフィルターでろ過し、感光性樹脂組成物eを得た。得られた感光性樹脂組成物を用い、上述(3)〜(10)の評価を実施した。
2:硬化膜
3:厚膜部
4:薄膜部
5:薄膜部
6:基板
7:TFT
8:TFT絶縁膜
9:配線
10:コンタクトホール
11:平坦化層
12:電極
13:画素分割層
14:半透光部
15:遮光部
16:透光部
17:基板
18:絶縁層
19:無アルカリガラス基板
20:第一電極
21:補助電極
22:画素分割層
23:有機EL層
24:第二電極
Claims (19)
- (A)アルカリ可溶性樹脂、(B)ラジカル重合性化合物、(C)光重合開始剤および(D)着色剤を含有する感光性樹脂組成物であって、前記(A)アルカリ可溶性樹脂が、ポリイミド、ポリイミド前駆体、ポリベンゾオキサゾール前駆体および/またはそれらの共重合体を含有し、前記(B)ラジカル重合性化合物が、(B−1)単独重合体としたときのガラス転移温度が150℃以上となる2官能以上の(メタ)アクリル化合物および(B−2)(B−1)以外の4官能以上の(メタ)アクリル化合物とを含有し、前記(D)着色剤が、ベンゾフラノン構造を有する黒色顔料および/またはペリレン系黒色顔料を含有する、感光性樹脂組成物。
- 前記(B−1)単独重合体としたときのガラス転移温度が150℃以上となる2官能以上の(メタ)アクリル化合物が、脂環式構造を含有する、請求項1に記載の感光性樹脂組成物。
- 前記脂環式構造が、トリシクロデカニル基、アダマンチル基、ヒドロキシアダマンチル基、ペンタシクロペンタデカニル基およびイソシアヌレート基からなる群のいずれかである、請求項2に記載の感光性樹脂組成物。
- 有機EL表示装置における画素分割層の段差形状を一括形成するために用いられる、請求項1〜3のいずれかに記載の感光性樹脂組成物。
- 前記(B−2)(B−1)以外の4官能以上の(メタ)アクリル化合物が、ラクトン変性鎖および/またはラクタム変性鎖を有する(メタ)アクリル化合物を含有する、請求項5に記載の感光性樹脂組成物。
- 前記(B−1)単独重合体としたときのガラス転移温度が150℃以上となる2官能以上の(メタ)アクリル化合物がメタクリル基を含む、請求項1〜6のいずれかに記載の感光性樹脂組成物。
- 前記(B)ラジカル重合性化合物100質量部に占める前記(B−1)単独重合体としたときのガラス転移温度が150℃以上となる2官能以上の(メタ)アクリル化合物の含有量が20〜80質量部、かつ前記(B−2)(B−1)以外の4官能以上の(メタ)アクリル化合物の含有量が20〜80質量部である、請求項1〜7のいずれかに記載の感光性樹脂組成物。
- さらに(E)熱架橋剤を含有する、請求項1〜8のいずれかに記載の感光性樹脂組成物。
- 前記(E)熱架橋剤が、(E−1)メチロール基および/またはアルコキシメチル基を合計6以上20以下有する化合物を含有する、請求項9に記載の感光性樹脂組成物。
- 請求項1〜10のいずれかに記載の感光性樹脂組成物の硬化物からなる硬化膜。
- 前記硬化膜が段差形状を有する、請求項11に記載の硬化膜。
- 前記硬化膜の押込み弾性率が7.0GPa以上12.0GPa以下の範囲である、請求項11または12に記載の硬化膜。
- 前記段差形状を有する硬化膜において、厚膜部の膜厚を(TFT)、薄膜部の膜厚を(THT)μmおよび前記厚膜部の膜厚(TFT)と薄膜部の膜厚(THT)との膜厚差を(ΔTFT−HT)μmとするとき、前記厚膜部の膜厚(TFT)、前記薄膜部の膜厚(THT)および前記厚膜部の膜厚と薄膜部の膜厚との膜厚差(ΔTFT−HT)が、式(α)〜(γ)で表される関係を満たす、請求項12または13に記載の硬化膜。
1.0≦(TFT)≦5.0 (α)
0.2≦(THT)≦4.0 (β)
0.5≦(ΔTFT−HT)≦4.0 (γ) - 請求項11〜14のいずれかに記載の硬化膜を具備する素子。
- 請求項11〜15のいずれかに記載の硬化膜を具備する有機EL表示装置。
- (1)請求項1〜10のいずれかに記載の感光性樹脂組成物を基板に塗布し、感光性樹脂膜を形成する工程、
(2)該感光性樹脂膜を乾燥する工程、
(3)乾燥した感光性樹脂膜にフォトマスクを介して露光する工程、
(4)露光した感光性樹脂膜を現像する工程および
(5)現像した感光性樹脂膜を加熱処理する工程
とを含む硬化膜の製造方法。 - 前記フォトマスクが、透光部及び遮光部を含むパターンを有するフォトマスクであって、前記透光部と遮光部の間に、透過率が透光部の値より低く、かつ透過率が遮光部の値より高い、半透光部を有するハーフトーンフォトマスクである、請求項17に記載の硬化膜の製造方法。
- 請求項17または18に記載の方法により硬化膜を形成する工程を含む、有機EL表示装置の製造方法。
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