JP6770196B2 - 黄色硬化性樹脂組成物、これを利用して製造されたカラーフィルターおよび画像表示装置 - Google Patents
黄色硬化性樹脂組成物、これを利用して製造されたカラーフィルターおよび画像表示装置 Download PDFInfo
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- JP6770196B2 JP6770196B2 JP2019531730A JP2019531730A JP6770196B2 JP 6770196 B2 JP6770196 B2 JP 6770196B2 JP 2019531730 A JP2019531730 A JP 2019531730A JP 2019531730 A JP2019531730 A JP 2019531730A JP 6770196 B2 JP6770196 B2 JP 6770196B2
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001062 red colorant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229910052950 sphalerite Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OCGWQDWYSQAFTO-UHFFFAOYSA-N tellanylidenelead Chemical compound [Pb]=[Te] OCGWQDWYSQAFTO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000007704 wet chemistry method Methods 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
- Optical Filters (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
Tは、透過率(%)であり、λは、560〜620nmから選ばれる波長である)。
本発明の一様態による黄色硬化性樹脂組成物は、黄色着色剤;および最大吸収波長が560〜620nmであり、下記数式1の透過特性を満たす波長吸収剤;を含むことによって、これを利用してカラーフィルターおよび画像表示装置の製造時に色再現性および光効率が向上するという利点がある。
Tは、透過率(%)であり、λは、560〜620nmから選ばれる波長である)。
本発明の一様態による黄色硬化性樹脂組成物は、黄色着色剤を含む。
モノアゾ系顔料:C.I.ピグメントイエロー1、2、5、8、105、120、150、168、182、183、190;
ピラゾロンアゾ系顔料:C.I.ピグメントイエロー10;
ジアゾ系顔料:C.I.ピグメントイエロー12、16、63、83、126、127、128、152、170、188;
アゾメチン系顔料:C.I.ピグメントイエロー101、129;
アントラキノン系顔料:C.I.ピグメントイエロー108、147、193、197、199、202;
イソインドリノン系顔料:C.I.ピグメントイエロー109、110、139、173、185;
キノリン系顔料:C.I.ピグメントイエロー115;
キノフタロン系顔料:C.I.ピグメントイエロー138;
ポリサイクリック系顔料:C.I.ピグメントイエロー148;
ジオキシム系顔料:C.I.ピグメントイエロー153;
ベンゾイミダゾロン系顔料:C.I.ピグメントイエロー154、175、180、181;
ヘテロサイクリック系顔料:C.I.ピグメントイエロー192;
ペリオン系(perinone)顔料:C.I.ピグメントイエロー196;
無機顔料:C.I.ピグメント31、32、30、119、157、162、184;
シアニン(Cyanine)系顔料;キサンテン(Xanthene)系顔料;メロシアニン(Merocyanine)系顔料;ジピリン(Dipyrrin)系顔料;アリルメチン(Arylmethine)系顔料;アクリジン(Acridine)系顔料;クマリン(Coumarin)系顔料;オキサジン(Oxazine)系顔料;テトラピロール(Tetrapyrrole)系顔料などを使用することができるが、これらに限定されるものではない。
本発明の一様態による黄色硬化性樹脂組成物は、最大吸収波長の範囲が560〜620nmであり、下記数式1の透過特性を満たす波長吸収剤を含む。
Tは、透過率(%)であり、λは、560〜620nmから選ばれる波長である)。
Mは、CuまたはZnであり、
X1は、それぞれ独立して、ハロゲン元素としてF、ClおよびBrよりなる群から選ばれ、nは、それぞれ独立して、0〜5の整数であり、
R1〜R4は、それぞれ独立して、メチル、エチル、プロピル、イソプロピルおよびtert−ブチルよりなる群から選ばれる。)
本発明の一実施形態による黄色硬化性樹脂組成物は、アルカリ可溶性樹脂をさらに含むことができる。
本発明の一実施形態による黄色硬化性樹脂組成物は、光重合性化合物をさらに含むことができる。
本発明の一実施形態による黄色硬化性樹脂組成物は、光重合開始剤をさらに含むことができる。
本発明の一実施形態による黄色硬化性樹脂組成物は、溶剤をさらに含むことができる。
本発明の一実施形態による黄色硬化性樹脂組成物は、本発明の目的を害しない範囲で当業者の必要に応じて充填剤、他の高分子化合物、界面活性剤、密着促進剤、酸化防止剤、紫外線吸収剤、凝集防止剤、硬化剤などの添加剤をさらに含むことができる。
本発明の他の様態は、前述した黄色硬化性樹脂組成物の硬化物を含むカラーフィルターである。
(S2)前記黄色コーティング層13上に赤色および緑色画素領域15a、15bを定義する隔壁51a、51b、51cを形成する段階;および
(S3)前記画素領域に自発光画素層15を形成する段階を経て製造する。
また、本発明のさらに他の様態は、前記カラーフィルターを含む画像表示装置である。
製造例1:CdSe/ZnSコアシェル構造の光ルミネセンス緑色量子ドット粒子の合成
CdO 0.4mmolと亜鉛アセテート(Zinc acetate)4mmol、オレイン酸(Oleic acid)5.5mLを1−オクタデセン(1−Octadecene)20mLとともに反応器に入れ、150℃に加熱して反応させた。その後、亜鉛にオレイン酸が置換されることによって生成された酢酸(acetic acid)を除去するために、前記反応物を100mTorrの真空下に20分間放置した。
その後、310℃の熱を加えて透明な混合物を得た後、これを20分間310℃を維持した後、0.4mmolのSe粉末と2.3mmolのS粉末を3mLのトリオクチルホスフィン(trioctylphosphine)に溶解させたSeおよびS溶液をCd(OA)2およびZn(OA)2溶液が入っている反応器に迅速に注入した。
撹拌器、温度計、還流冷却管、滴下漏斗および窒素導入管を具備したフラスコを準備し、一方、N−ベンジルマレイミド45重量部、メタクリル酸45重量部、トリシクロデシルメタクリレート10重量部、t−ブチルペルオキシ−2−エチルヘキサノアート4重量部、プロピレングリコールモノメチルエーテルアセテート40重量部を投入した後、撹拌混合して、モノマー滴下漏斗を準備し、n−ドデカンジオール6重量部、プロピレングリコールモノメチルエーテルアセテート24重量部を入れて撹拌混合して、連鎖移動剤滴下漏斗を準備した。
下記表1に記載されたように、それぞれ成分を混合した後、全体固形分が20重量%になるように、プロピレングリコールモノメチルエーテルアセテートで希釈した後、十分に撹拌して、自発光感光性樹脂組成物を得た。
下記表2に記載されたように、それぞれ成分を混合した後、全体固形分が20重量%になるように、プロピレングリコールモノメチルエーテルアセテートで希釈した後、十分に撹拌して、黄色硬化性樹脂組成物を得た。
前記実施例1〜6および比較例1〜2で製造した黄色硬化性樹脂組成物の透過特性を確認するために、下記のように行った。
製造例4−1〜4−6および製造例4−13〜4−14
(1)黄色コーティング層の形成
まず、前記実施例1〜6および比較例1〜2の黄色硬化性樹脂組成物をスピンコーティング法で100×100mmのサイズのガラス基板(Corning(登録商標)EAGLE XG(登録商標)Slim、コーニング社製)の上に塗布した後、加熱板の上に載置し、100℃の温度で3分間維持して、薄膜を形成させた。
前記製造例3−1で製造された自発光感光性樹脂組成物を利用して、前記(1)と同じ方法で、前記(1)で製造されたそれぞれの黄色コーティング層上に厚さ5μmの自発光画素層を形成して、製造例4−1〜4−6および製造例4−13〜4−14を製造した。
前記製造例4−1〜4−6および製造例4−13〜4−14と同じ方法でカラーフィルターを製造し、自発光画素層の形成のための自発光感光性樹脂組成物を前記製造例3−2にして製造例4−7〜製造例4−12および製造例4−15〜4−16を製造した。
前記製造例4で製作されたカラーフィルターの発光強度を下記のように測定した。
13 黄色コーティング層
15 自発光層
15a 赤色画素領域
15b 緑色画素領域
51a、51b、51c 隔壁
101 光源
Claims (8)
- 青色光源を含む装置に利用される黄色コーティング層を形成するための組成物であって、
黄色着色剤;および最大吸収波長が560〜620nmであり、下記数式1の透過特性を満たす波長吸収剤;を含み、
前記黄色着色剤は、これを含む黄色硬化性樹脂組成物のうち固形分全体100重量%に対して、5〜80重量%で含まれることを特徴とする黄色硬化性樹脂組成物:
[数式1]
(前記数式1で、
Tは、透過率(%)であり、λは、560〜620nmから選ばれる最大吸収波長である)。 - 前記黄色硬化性樹脂組成物は、アルカリ可溶性樹脂、光重合性化合物、光重合開始剤、溶剤および添加剤よりなる群から選ばれる一つ以上をさらに含むものである、請求項1に記載の黄色硬化性樹脂組成物。
- 前記波長吸収剤は、下記化学式1で表される化合物を含むものである、請求項1に記載の黄色硬化性樹脂組成物。
[化学式1]
(前記化学式1で、
Mは、CuまたはZnであり、
X1は、それぞれ独立して、ハロゲン元素としてF、ClおよびBrよりなる群から選ばれ、nは、それぞれ独立して、0〜5の整数であり、
R1〜R4は、それぞれ独立して、メチル、エチル、プロピル、イソプロピルおよびtert−ブチルよりなる群から選ばれる)。 - 前記波長吸収剤は、前記黄色硬化性樹脂組成物のうち固形分全体100重量%に対して、1〜30重量%で含まれるものである、請求項1に記載の黄色硬化性樹脂組成物。
- 請求項1〜4のいずれかに記載の黄色硬化性樹脂組成物の硬化物を含む黄色コーティング層;および前記黄色コーティング層上に形成され、量子ドットを含有する自発光画素層;を含むカラーフィルター。
- 前記黄色コーティング層は、赤色画素層乃至緑色画素層上に形成されたものである、請求項5に記載のカラーフィルター。
- 請求項5に記載のカラーフィルターを含む画像表示装置。
- 前記カラーフィルターは、黄色コーティング層が光源と向かい合う方向に配置されたものである、請求項7に記載の画像表示装置。
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US6140019A (en) * | 1997-07-24 | 2000-10-31 | Jsr Corporation | Radiation sensitive composition |
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US8947619B2 (en) * | 2006-07-06 | 2015-02-03 | Intematix Corporation | Photoluminescence color display comprising quantum dots material and a wavelength selective filter that allows passage of excitation radiation and prevents passage of light generated by photoluminescence materials |
US20080074583A1 (en) * | 2006-07-06 | 2008-03-27 | Intematix Corporation | Photo-luminescence color liquid crystal display |
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JP5292651B2 (ja) * | 2008-12-11 | 2013-09-18 | 山田化学工業株式会社 | 合わせガラス用中間膜及び合わせガラス |
JP4650578B2 (ja) * | 2009-03-26 | 2011-03-16 | カシオ計算機株式会社 | 液晶表示装置 |
JP5707105B2 (ja) | 2010-11-19 | 2015-04-22 | 東洋インキScホールディングス株式会社 | カラーフィルタ用黄色着色組成物及びカラーフィルタ |
TWI633342B (zh) * | 2012-03-22 | 2018-08-21 | 日本觸媒股份有限公司 | Light selective transmission filter, resin sheet and solid-state imaging element |
KR101531616B1 (ko) * | 2012-12-05 | 2015-06-25 | 제일모직 주식회사 | 코어-쉘 염료, 이를 포함하는 컬러필터용 감광성 수지 조성물 및 이를 이용한 컬러필터 |
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JP2016034994A (ja) | 2014-08-01 | 2016-03-17 | クラリアント・インターナシヨナル・リミテツド | 彩度と色相が改良されたイエロー着色剤組成物、そのための顔料組成物およびそれらの使用 |
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KR102433073B1 (ko) | 2022-08-16 |
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TWI725261B (zh) | 2021-04-21 |
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