JP2018131612A - 硬化性樹脂組成物、硬化膜及び表示装置 - Google Patents
硬化性樹脂組成物、硬化膜及び表示装置 Download PDFInfo
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- JP2018131612A JP2018131612A JP2018021623A JP2018021623A JP2018131612A JP 2018131612 A JP2018131612 A JP 2018131612A JP 2018021623 A JP2018021623 A JP 2018021623A JP 2018021623 A JP2018021623 A JP 2018021623A JP 2018131612 A JP2018131612 A JP 2018131612A
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- 150000004053 quinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- OCGWQDWYSQAFTO-UHFFFAOYSA-N tellanylidenelead Chemical compound [Pb]=[Te] OCGWQDWYSQAFTO-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000010409 thin film Substances 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Classifications
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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Abstract
Description
[1] 有機配位子が配位した半導体粒子である配位子含有半導体粒子(A)、樹脂(B)及び重合性化合物(C)を含み、
前記配位子含有半導体粒子(A)における前記半導体粒子に対する前記有機配位子の含有量比が、質量比で0.1以上5.0未満である、硬化性樹脂組成物。
〔i〕連結基を介して分子主鎖に結合するカルボキシル基及び/又はカルボン酸無水物基と、分子主鎖に直接結合するカルボキシル基及び/又はカルボン酸無水物基とを有する樹脂(B−1a)を含む、
〔ii〕すべてのカルボキシル基及び/又はカルボン酸無水物基が、連結基を介して分子主鎖に結合している樹脂(B−1b)と、すべてのカルボキシル基及び/又はカルボン酸無水物基が、分子主鎖に直接結合している樹脂(B−2)とを含む、
のいずれかを満たす、[1]又は[2]に記載の硬化性樹脂組成物。
本発明に係る硬化性樹脂組成物は、有機配位子が配位した半導体粒子である配位子含有半導体粒子(A)、樹脂(B)及び重合性化合物(C)を含む。該硬化性樹脂組成物は、良好なパターニング性を示すことができる。例えば、該硬化性樹脂組成物によれば、所望の線幅を有するパターニングされた硬化膜を精度良く形成することが可能である。該硬化性樹脂組成物によれば、上記線幅が比較的細い場合であっても、パターニングされた硬化膜を精度良く形成することが可能である。
硬化性樹脂組成物は、有機配位子が配位した半導体粒子である配位子含有半導体粒子(A)を含む。上記有機配位子が配位される半導体粒子は、好ましくは発光性(蛍光発光性)の半導体粒子である。発光性の半導体粒子を含む硬化性樹脂組成物から形成される波長変換膜等の硬化膜は、所望の波長域の蛍光発光を示す色再現性に優れたものであり得る。
有機配位子は、例えば半導体粒子の表面に配位することができる。
Y−Z
で表される有機化合物であることができる。式中、Yは上記の極性基であり、Zはヘテロ原子(N、O、S、ハロゲン原子等)を含んでいてもよい1価の炭化水素基である。該炭化水素基は、炭素−炭素二重結合等の不飽和結合を1個又は2個以上有していてもよい。該炭化水素基は、直鎖状、分岐鎖状又は環状構造を有していてもよい。該炭化水素基の炭素数は、例えば1以上40以下であり、1以上30以下であってもよい。該炭化水素基に含まれるメチレン基は、−O−、−S−、−C(=O)−、−C(=O)−O−、−O−C(=O)−、−C(=O)−NH−、−NH−等で置換されていてもよい。該炭化水素基は、配位子含有半導体粒子(A)の調製の簡便さから、通常、ヘテロ原子を含まない場合が多い。
Y−Zで表される有機配位子は、好ましくは炭素数が5以上12以下である飽和脂肪酸又は炭素数が5以上12以下である不飽和脂肪酸である。
硬化性樹脂組成物は、樹脂(B)を含有する。硬化性樹脂組成物は、樹脂(B)として1種又は2種以上の樹脂を含有することができる。樹脂(B)は、アルカリ可溶性樹脂であることが好ましい。アルカリ可溶性とは、アルカリ化合物の水溶液である現像液に溶解する性質のことをいう。樹脂(B)としては、以下の樹脂[K1]〜[K6]等が挙げられる。
樹脂[K2]:(a)と(b)と、(a)と共重合可能な単量体(c)(ただし、(a)及び(b)とは異なる。)〔以下、「(c)」ともいう。〕との共重合体、
樹脂[K3]:(a)と(c)との共重合体、
樹脂[K4]:(a)と(c)との共重合体に(b)を反応させて得られる樹脂、
樹脂[K5]:(b)と(c)との共重合体に(a)を反応させて得られる樹脂、
樹脂[K6]:(b)と(c)との共重合体に(a)を反応させ、さらにカルボン酸無水物を反応させて得られる樹脂。
(メタ)アクリル酸、クロトン酸、o−、m−、p−ビニル安息香酸、コハク酸モノ〔2−(メタ)アクリロイルオキシエチル〕、フタル酸モノ〔2−(メタ)アクリロイルオキシエチル〕等の不飽和モノカルボン酸類;
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3−ビニルフタル酸、4−ビニルフタル酸、3,4,5,6−テトラヒドロフタル酸、1,2,3,6−テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸、1、4−シクロヘキセンジカルボン酸等の不飽和ジカルボン酸類;
メチル−5−ノルボルネン−2,3−ジカルボン酸、5−カルボキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−エチルビシクロ[2.2.1]ヘプト−2−エン等のカルボキシ基を含有するビシクロ不飽和化合物類;
無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3−ビニルフタル酸無水物、4−ビニルフタル酸無水物、3,4,5,6−テトラヒドロフタル酸無水物、1,2,3,6−テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン無水物(ハイミック酸無水物)等の不飽和ジカルボン酸類無水物;
α−(ヒドロキシメチル)(メタ)アクリル酸のような、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和(メタ)アクリル酸類等が挙げられる。
メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−ブチル(メタ)アクリレート、sec−ブチル(メタ)アクリレート、tert−ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ドデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、シクロペンチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−メチルシクロヘキシル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン−8−イル(メタ)アクリレート〔当該技術分野では、慣用名として「ジシクロペンタニル(メタ)アクリレート」と呼ばれている。また、「トリシクロデシル(メタ)アクリレート」と呼ばれることもある。〕、トリシクロ[5.2.1.02,6]デセン−8−イル(メタ)アクリレート〔当該技術分野では、慣用名として「ジシクロペンテニル(メタ)アクリレート」と呼ばれている。〕、ジシクロペンタニルオキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、アダマンチル(メタ)アクリレート、アリル(メタ)アクリレート、プロパルギル(メタ)アクリレート、フェニル(メタ)アクリレート、ナフチル(メタ)アクリレート、ベンジル(メタ)アクリレート等の(メタ)アクリル酸エステル類;
2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート等のヒドロキシ基含有(メタ)アクリル酸エステル類;
マレイン酸ジエチル、フマル酸ジエチル、イタコン酸ジエチル等のジカルボン酸ジエステル;
ビシクロ[2.2.1]ヘプト−2−エン、5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシメチルビシクロ[2.2.1]ヘプト−2−エン、5−(2’−ヒドロキシエチル)ビシクロ[2.2.1]ヘプト−2−エン、5−メトキシビシクロ[2.2.1]ヘプト−2−エン、5−エトキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジヒドロキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジ(ヒドロキシメチル)ビシクロ[2.2.1]ヘプト−2−エン、5,6−ジ(2’−ヒドロキシエチル)ビシクロ[2.2.1]ヘプト−2−エン、5,6−ジメトキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジエトキシビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシ−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシ−5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシメチル−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−tert−ブトキシカルボニルビシクロ[2.2.1]ヘプト−2−エン、5−シクロヘキシルオキシカルボニルビシクロ[2.2.1]ヘプト−2−エン、5−フェノキシカルボニルビシクロ[2.2.1]ヘプト−2−エン、5,6−ビス(tert−ブトキシカルボニル)ビシクロ[2.2.1]ヘプト−2−エン、5,6−ビス(シクロヘキシルオキシカルボニル)ビシクロ[2.2.1]ヘプト−2−エン等のビシクロ不飽和化合物類;
N−フェニルマレイミド、N−シクロヘキシルマレイミド、N−ベンジルマレイミド、N−スクシンイミジル−3−マレイミドベンゾエート、N−スクシンイミジル−4−マレイミドブチレート、N−スクシンイミジル−6−マレイミドカプロエート、N−スクシンイミジル−3−マレイミドプロピオネート、N−(9−アクリジニル)マレイミド等のジカルボニルイミド誘導体類;
スチレン、α−メチルスチレン、m−メチルスチレン、p−メチルスチレン、ビニルトルエン、p−メトキシスチレン、アクリロニトリル、メタクリロニトリル、塩化ビニル、塩化ビニリデン、アクリルアミド、メタクリルアミド、酢酸ビニル、1,3−ブタジエン、イソプレン、2,3−ジメチル−1,3−ブタジエン等
が挙げられる。
(a)に由来する構造単位;2モル%以上50モル%以下(より好ましくは10モル%以上45モル%以下)、
(b)に由来する構造単位、特に(b1)に由来する構造単位;50モル%以上98モル%以下(より好ましくは55モル%以上90モル%以下)。
(a)に由来する構造単位;4モル%以上45モル%以下(より好ましくは10モル%以上30モル%以下)、
(b)に由来する構造単位、特に(b1)に由来する構造単位;2モル%以上95モル%以下(より好ましくは5モル%以上80モル%以下)、
(c)に由来する構造単位;1モル%以上65モル%以下(より好ましくは5モル%以上60モル%以下)。
(a)に由来する構造単位;2モル%以上55モル%以下(より好ましくは10モル%以上50モル%以下)、
(c)に由来する構造単位;45モル%以上98モル%以下(より好ましくは50モル%以上90モル%以下)。
(a)に由来する構造単位;5モル%以上50モル%以下(より好ましくは10モル%以上45モル%以下)、
(c)に由来する構造単位;50モル%以上95モル%以下(より好ましくは55モル%以上90モル%以下)。
(b)に由来する構造単位、特に(b1)に由来する構造単位;5モル%以上95モル%以下(より好ましくは10モル%以上90モル%以下)、
(c)に由来する構造単位;5モル%以上95モル%以下(より好ましくは10モル%以上90モル%以下)。
[式(a1)中、
R1は、水素原子又はメチル基を表す。
R2は、炭素数2〜6のアルカンジイル基若しくは炭素数5〜12のシクロアルカンジイル基を表すか、又はYが水素原子でない場合には該アルカンジイル基から1個の水素原子を引き抜いた3価の基を表す。
R3は、炭素数2〜6のアルカンジイル基、炭素数5〜12のシクロアルカンジイル基若しくは炭素数5〜12のシクロアルケンジイル基を表すか、又は2価の芳香族基を表す。
Yは、水素原子又は炭素数1〜8のアルキル基であり、該アルキル基に含まれるメチレン基は、−O−、−S−、−C(=O)−、−C(=O)−O−、−O−C(=O)−、−C(=O)−NH−又は−NH−で置換されていてもよい。
〔i〕連結基を介して分子主鎖に結合するカルボキシル基及び/又はカルボン酸無水物基と、分子主鎖に直接結合するカルボキシル基及び/又はカルボン酸無水物基とを有する樹脂(B−1a)を含む、
〔ii〕すべてのカルボキシル基及び/又はカルボン酸無水物基が、連結基を介して分子主鎖に結合している樹脂(B−1b)と、すべてのカルボキシル基及び/又はカルボン酸無水物基が、分子主鎖に直接結合している樹脂(B−2)とを含む、
のいずれかを満たすことが好ましい。
酸価は、樹脂1gを中和するのに必要な水酸化カリウムの量(mg)として測定される値であり、例えば水酸化カリウム水溶液を用いた滴定により求めることができる。
溶液酸価は、樹脂(B)を所定の溶媒に溶解させて測定した値であり、その溶液の樹脂濃度は例えば10質量%以上50質量%以下である。
樹脂(B)の溶液酸価が前述の範囲にあることで、配位子含有半導体粒子及び樹脂(B)のいずれもが凝集することなくこれらを混合することができる。
重合性化合物(C)は、光照射等より重合開始剤(D)から発生する活性ラジカル等によって重合し得る化合物であれば、特に限定されず、重合性のエチレン性不飽和結合を有する化合物等が挙げられる。重合性化合物(C)の重量平均分子量は、3000以下であることが好ましい。
硬化性樹脂組成物は、重合開始剤(D)を含むことができる。重合開始剤(D)は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始し得る化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。
硬化性樹脂組成物は、重合開始助剤(D1)を含むことができる。重合開始助剤(D1)は、重合開始剤(D)によって重合が開始された重合性化合物(C)の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤(D1)を含む場合、重合開始剤(D)と組み合わせて用いられる。
硬化性樹脂組成物は、1種又は2種以上の溶剤(E)を含むことが好ましい。溶剤(E)としては、エステル溶剤(−C(=O)−O−を含む溶剤)、エステル溶剤以外のエーテル溶剤(−O−を含む溶剤)、エーテルエステル溶剤(−C(=O)−O−と−O−とを含む溶剤)、エステル溶剤以外のケトン溶剤(−C(=O)−を含む溶剤)、アルコール溶剤、芳香族炭化水素溶剤、アミド溶剤及びジメチルスルホキシド等が挙げられる。
硬化性樹脂組成物は、1種又は2種以上のレベリング剤(F)を含むことができる。レベリング剤(F)としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。
硬化性樹脂組成物の耐熱性及び耐光性を向上させる観点から、硬化性樹脂組成物は、酸化防止剤(G)を含有することができる。酸化防止剤(G)としては、工業的に一般に使用される酸化防止剤であれば特に限定はなく、フェノール系酸化防止剤、リン系酸化防止剤及び硫黄系酸化防止剤等を用いることができる。酸化防止剤(G)は、2種以上を併用してもよい。
硬化性樹脂組成物には、必要に応じて、充填剤、樹脂(B)以外の高分子化合物、密着促進剤、紫外線吸収剤、凝集防止剤、有機酸、有機アミン化合物、チオール化合物、硬化剤、光散乱剤等の添加剤を1種又は2種以上含有することができる。
硬化性樹脂組成物は、配位子含有半導体粒子(A)、樹脂(B)、重合性化合物(C)、並びに必要に応じて使用される他の成分を混合することにより調製することができる。
硬化性樹脂組成物からなる膜(層)を硬化させることによって硬化膜を得ることができる。この際、フォトリソグラフ法、インクジェット法、印刷法等の方法によってパターニングすることによりパターニングされた硬化膜を得ることができる。硬化膜又はパターニングされた硬化膜は、入射する光の波長とは異なる波長の光を出射する波長変換膜(波長変換フィルタ)として好適に用いることができる。波長変換膜は、液晶表示装置、有機EL装置等の表示装置に好適に用いることができる。パターニング方法は、フォトリソグラフィ法であることが好ましい。フォトリソグラフィ法は、硬化性樹脂組成物を基板に塗布し、乾燥させて硬化性樹脂組成物層を形成し、フォトマスクを介して該硬化性樹脂組成物層を露光して、現像する方法である。
(1)半導体量子ドットの準備
半導体量子ドットとして、InP(コア)/ZnS(第1シェル)/ZnS(第2シェル)の構造を有するコアシェル型半導体量子ドットINP530〔NN−LABS社製〕を使用した。この半導体量子ドットの表面にはオレイルアミンが配位している。
次に、上記の半導体量子ドット(QD)について、次の手順で配位子低減処理を行った。まず、上記(1)で得られたQDを含む分散液1容量部にヘキサン2容量部を加えて希釈した。その後、エタノール30容量部を添加してQDを沈殿させ、遠心分離処理を行った。上澄み液を除去し、ヘキサン3容量部を加えてQDを再分散させた。このような処理(エタノール添加による沈殿→遠心分離→上澄み液除去→ヘキサン添加による再分散)を合計3回行った。ただし、3回目の再分散時には、ヘキサンではなくシクロヘキサンカルボン酸イソプロピル(CHCI)をQD(オレイルアミン配位子を含む)の濃度が20質量%となるように添加し、QD分散液−Aを得た。
得られたQD分散液−Aについて、L/P質量比〔半導体量子ドット(半導体粒子)に対する有機配位子(オレイルアミン)の質量比〕を次の手順で測定した。アルミパンに30μLのQD分散液を測りとり、熱重量分析装置「TGDTA6200」(Seiko Instrument社製)を用いて、窒素気流下において、5℃/minの昇温速度で45℃から550℃までの温度範囲について熱重量測定を行った。CHCIの揮発終了温度である170℃から550℃までの変化重量を有機配位子の重量(質量)とし、測定終了後の残渣物の重量を半導体量子ドット(半導体粒子)の重量(質量)とし、有機配位子の質量を半導体量子ドットの質量で除することでL/P質量比を求めた。
製造例1−1で得られたQD分散液−A 100部にオレイン酸14.5部を加え、QD(オレイルアミン及びオレイン酸配位子を含む)の濃度が20質量%となるようにCHCIを添加した後、80℃で3時間撹拌することによりQD分散液−Bを得た。製造例1−1の(3)と同様にして、得られたQD分散液−Bについて、L/P質量比を測定した。
製造例1−1で得られたQD分散液−A 100部にオレイン酸49.0部を加え、QD(オレイルアミン及びオレイン酸配位子を含む)の濃度が20質量%となるようにCHCIを添加した後、80℃で3時間撹拌することによりQD分散液−Cを得た。製造例1−1の(3)と同様にして、得られたQD分散液−Cについて、L/P質量比を測定した。
冷却管と攪拌機を備えたフラスコに、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)100部を仕込んで窒素置換した。70℃で撹拌しながら、同温度でメチルメタクリレート(東京化成工業株式会社製)7.6部、ジシクロペンタニルメタクリレート(日立化成株式会社製「ファンクリル FA−513M」)5.6部、メタクリル酸(東京化成工業株式会社製)2.7部、コハク酸1−[2−(メタクリロイルオキシ)エチル](シグマアルドリッチジャパン合同会社製)6.4部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)(和光純薬工業株式会社製)2.1部、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)〔PEMP〕(SC有機化学株式会社製)1.4質量部及びPGMEA100部の混合溶液を30分かけて滴下し、同温度で2時間重合反応を行った。反応溶液を室温まで徐冷後、エタノールに滴下し、沈殿物をろ過回収し、40℃の真空乾燥機で乾燥させた。得られた白色粉末20部を、PGMEA40部及びCHCI40部の混合溶媒に溶解して、樹脂溶液−aを得た(樹脂濃度:20質量%)。得られた樹脂の重量平均分子量は17000であった(ゲルパーミエーションクロマトグラフィによる標準ポリスチレン換算値)。仕込み量に基づいて、得られた樹脂固形分の酸価はX/Y=80/70(mg−KOH/g)と算出された。
製造例2−1における上記混合溶液に含まれる単量体として、メチルメタクリレート(東京化成社製)14.3部及びメタクリル酸(東京化成工業株式会社製)2.4部とし、コハク酸1−[2−(メタクリロイルオキシ)エチル](シグマアルドリッチジャパン合同会社製)を用いなかったこと以外は製造例2−1と同様にして、樹脂溶液−bを得た(樹脂濃度:20質量%)。得られた樹脂の重量平均分子量は17000であった(ゲルパーミエーションクロマトグラフィによる標準ポリスチレン換算値)。仕込み量に基づいて、得られた樹脂固形分の酸価はX/Y=70/0(mg−KOH/g)と算出された。
製造例2−1における上記混合溶液に含まれる単量体として、メチルメタクリレート(東京化成工業株式会社製)10.3部とし、メタクリル酸(東京化成工業株式会社製)を用いなかったこと以外は製造例2−1と同様にして、樹脂溶液−cを得た(樹脂濃度:20質量%)。得られた樹脂の重量平均分子量は16000であった(ゲルパーミエーションクロマトグラフィによる標準ポリスチレン換算値)。仕込み量に基づいて、得られた樹脂固形分の酸価はX/Y=0/70(mg−KOH/g)と算出された。
上記特許文献1の[0191]の記載に従って樹脂溶液を調製した後、PGMEAを添加して、樹脂濃度20質量%の樹脂溶液−dを得た。仕込み量に基づいて、得られた樹脂固形分の酸価はX/Y=49/0(mg−KOH/g)と算出された。
製造例1−1で得られたQD分散液−A 25部、製造例2−1で得られた樹脂溶液−a 14.0部、製造例2−2で得られた樹脂溶液−b 42.0部、及び酸化防止剤(G−1)を20質量%濃度で含むPGMEA溶液1.85部をフラスコに入れ、80℃で12時間加熱撹拌した。その後、室温まで放冷して、QD及び樹脂を含有する液を得た。
使用したQD分散液、樹脂溶液及びその他の配合成分の種類及びそれらの使用量を表2に示されるとおりとしたこと以外は実施例1と同様にして硬化性樹脂組成物を調製した。実施例2〜4及び比較例1〜2で得られた硬化性樹脂組成物の固形分濃度はいずれも25質量%である。実施例2〜4及び比較例1〜2で得られた硬化性樹脂組成物において、樹脂は均一溶解され、QDは均一分散されていることが目視観察により確認された。
製造例1−1で得られたQD分散液−A 25部、製造例2−1で得られた樹脂溶液−a 11.4部、製造例2−2で得られた樹脂溶液−b 34.1部、及び酸化防止剤(G−1)を20質量%濃度で含むPGMEA溶液1.50部をフラスコに入れ、80℃で12時間加熱撹拌した。その後、室温まで放冷して、QD及び樹脂を含有する液を得た。
〔1〕重合性化合物(C−1):プロポキシ化ペンタエリスリトールトリアクリレート(新中村化学工業株式会社製「NKエステル ATM−4PL」)、
〔2〕重合性化合物(C−2):ペンタエリスリトールトリアクリレート(新中村化学工業株式会社製「NKエステル A−TMM−3LM−N」)、
〔3〕重合開始剤(D−1):株式会社ADEKA製のO−アシルオキシム系重合開始剤「NCI−930」、
〔4〕溶剤(E−1):PGMEA、
〔5〕レベリング剤(F−1):東レ・ダウコーニング株式会社製のポリエーテル変性シリコーンオイル系レベリング剤「トーレシリコーンSH8400」、
〔6〕酸化防止剤(G−1):株式会社ADEKA製のヒンダードフェノール系酸化防止剤「アデカスタブ(登録商標)AO−60」、
〔7〕酸化防止剤(G−2):住友化学株式会社製のフェノールリン系酸化防止剤「スミライザー(登録商標)GP」、
〔8〕光拡散剤:山陽色素株式会社製の酸化チタン粒子分散液「SF WHITE GC4134」(酸化チタン粒子濃度:73質量%)。
(1)パターニング性
ガラス基板に0.45mLの硬化性樹脂組成物を滴下し、150rpm、20秒の条件でスピンコートを行った後、100℃、3分間の条件で乾燥(プリベーク)させて硬化性樹脂組成物層を形成した。次いで、線幅が50μmであるラインアンドスペースパターンを有するフォトマスクを用いて、大気雰囲気下、40mJ/cm2の露光量(365nm基準)でパターン露光を行った。基板とフォトマスクとの距離は120μmとした。パターン露光後の硬化性樹脂組成物層を、水酸化カリウムの濃度が0.04質量%である水系現像液に23℃で70秒間浸漬し、水洗後、オーブン中、230℃で20分間ポストベークを行い、パターニングされた硬化膜を得た。硬化膜の膜厚はいずれも5μm以上6μm以下であった。
B:ライン幅が、[マスク幅(50μm)−6μm]以上[マスク幅(50μm)−2μm]未満の範囲内であるか、又は[マスク幅(50μm)+3μm]超[マスク幅(50μm)+10μm]以下の範囲内である、
C:ライン幅が、[マスク幅(50μm)−6μm]未満であるか、又は[マスク幅(50μm)+10μm]超である、
D:現像が不十分な箇所、すなわち、隣り合うライン同士が繋がっている箇所が存在する、又は現像密着性が不十分でラインが剥離している。
フォトマスクを用いないこと以外は、上記「パターニング性」の評価試験と同様にしてガラス基板上に硬化膜を形成した。この硬化膜付ガラス基板を青色バックライト上に配置し、オーシャンフォトニクス株式会社製の全光束測定装置「CSTM−OP−RADIANT−FLUX」を用いて発光強度を測定した。実施例5の硬化膜の発光強度は、実施例1の硬化膜の発光強度の9倍であった。
Claims (6)
- 有機配位子が配位した半導体粒子である配位子含有半導体粒子(A)、樹脂(B)及び重合性化合物(C)を含み、
前記配位子含有半導体粒子(A)における前記半導体粒子に対する前記有機配位子の含有量比が、質量比で0.1以上5.0未満である、硬化性樹脂組成物。 - 前記樹脂(B)は、連結基を介して分子主鎖に結合するカルボキシル基及び/又はカルボン酸無水物基を有する樹脂(B−1)を含む、請求項1に記載の硬化性樹脂組成物。
- 前記樹脂(B)は、下記〔i〕及び〔ii〕:
〔i〕連結基を介して分子主鎖に結合するカルボキシル基及び/又はカルボン酸無水物基と、分子主鎖に直接結合するカルボキシル基及び/又はカルボン酸無水物基とを有する樹脂(B−1a)を含む、
〔ii〕すべてのカルボキシル基及び/又はカルボン酸無水物基が、連結基を介して分子主鎖に結合している樹脂(B−1b)と、すべてのカルボキシル基及び/又はカルボン酸無水物基が、分子主鎖に直接結合している樹脂(B−2)とを含む、
のいずれかを満たす、請求項1又は2に記載の硬化性樹脂組成物。 - 光散乱剤をさらに含む、請求項1〜3のいずれか1項に記載の硬化性樹脂組成物。
- 請求項1〜4のいずれか1項に記載の硬化性樹脂組成物から形成される、硬化膜。
- 請求項5に記載の硬化膜を含む、表示装置。
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WO2021200276A1 (ja) * | 2020-03-31 | 2021-10-07 | 住友化学株式会社 | 硬化性樹脂組成物及び表示装置 |
WO2021200277A1 (ja) * | 2020-03-31 | 2021-10-07 | 住友化学株式会社 | 硬化性樹脂組成物及び表示装置 |
WO2022044822A1 (ja) * | 2020-08-31 | 2022-03-03 | 住友化学株式会社 | 樹脂組成物、樹脂膜及び表示装置 |
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