JP6903854B2 - 着色剤化合物およびこれを含む着色組成物 - Google Patents
着色剤化合物およびこれを含む着色組成物 Download PDFInfo
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- JP6903854B2 JP6903854B2 JP2019548924A JP2019548924A JP6903854B2 JP 6903854 B2 JP6903854 B2 JP 6903854B2 JP 2019548924 A JP2019548924 A JP 2019548924A JP 2019548924 A JP2019548924 A JP 2019548924A JP 6903854 B2 JP6903854 B2 JP 6903854B2
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- 125000003118 aryl group Chemical group 0.000 claims description 13
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- 125000006267 biphenyl group Chemical group 0.000 description 3
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 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 compound 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 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012719 thermal polymerization Methods 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
- 238000001291 vacuum drying Methods 0.000 description 1
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- 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
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- Spectroscopy & Molecular Physics (AREA)
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- Materials For Photolithography (AREA)
Description
本出願は、2017年9月4日付の韓国特許出願第10−2017−0112691号および2018年8月22日付の韓国特許出願第10−2018−0098142号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
[化学式1]
R1〜R5は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数6〜20の芳香族環が1以上結合したN−アルキレン−ピペリジンジオン(piperidine dione)、またはN−アルキレン−ピロリジンジオン(pyrrolidine dione)であり;
R6は、下記化学式2または3であり;
R7〜R10は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり;
[化学式2]
R11〜R20は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり、
R7〜R20のうちの1つ以上は、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基である。
本発明の一実施形態による着色剤化合物は、下記化学式1で表される。
[化学式1]
R1〜R5は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数6〜20の芳香族環が1以上結合したN−アルキレン−ピペリジンジオン(piperidine dione)、またはN−アルキレン−ピロリジンジオン(pyrrolidine dione)であり;
R6は、下記化学式2または3であり;
R7〜R10は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり;
[化学式2]
R11〜R20は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり、
R7〜R20のうちの1つ以上は、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基である。
[化学式4]
[化学式10]
[化学式6]
本発明の一実施形態によれば、前記着色剤化合物を含む着色組成物を提供する。
[発明を実施するための形態]
前記製造例1〜11および比較製造例による化合物を用意し、これをジメチルホルムアミド(DMF)100gに対する溶解度を測定し、その結果を下記表1に示す。具体的には、溶解度が1%以上の場合はO、1%未満の場合はXと表示した。
前記製造例1により合成された化合物1を5.554g、バインダー樹脂としてはベンジルメタクリレートとメタクリル酸の共重合体(モル比70:30、酸価は113 KOH mg/g、GPCで測定した重量平均分子量20,000)、分子量分布(PDI)2.0g、固形分(S.C)25%、溶媒PGMEA含み)10.376g、光開始剤としてはI−369(BASF社製)2.018g、光重合性化合物としてDPHA(日本化薬社製)12.443g、溶剤PGMEA(ポリプロピレングリコールモノメチルエーテルアセテート)68.593g、および添加剤としてF−475(DIC社製)1.016gを混合して、感光性樹脂組成物を製造した。
前記製造例2により合成された化合物2を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例3により合成された化合物3を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例4により合成された化合物4を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例5により合成された化合物5を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例6により合成された化合物6を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例7により合成された化合物7を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例8により合成された化合物8を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例9により合成された化合物9を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例10により合成された化合物10を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記製造例11により合成された化合物11を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記比較製造例の化合物を使用したことを除いては、前記実施例1と同様の方法で、感光性樹脂組成物を製造した。
前記実施例1〜11および比較例1による感光性樹脂組成物を、基板製作にそれぞれ使用した。具体的には、前記実施例および比較例による感光性樹脂組成物をガラス(5x5cm)上にスピンコート(spincoating)し、100℃で100秒間前熱処理(prebake)を施してフィルムを形成した。
前記基板製作方法により製作された基板を分光器(MCPD−大塚電子社製)を用いて、380nm〜780nm範囲の可視光領域の透過率スペクトルを得た。また、前熱処理(prebake)基板を追加的に230℃で20分間後熱処理(postbake)を施して、同じ装備と測定範囲で透過率スペクトルを得た。
ΔE(L*、a*、b*)={(ΔL*)2+(Δa*)2+(Δb*)2}1/2
上記式において、ΔE値が小さいということは、色耐熱性に優れていることを意味し、一般的にΔEab<3の値を有すると、耐熱性に優れた色材であると言われる。
下記表3に示す構成成分および組成比率(単位:g)で混合して、実施例12〜22および、比較例2の感光性樹脂組成物を製造した。前記製造した感光性樹脂組成物を用いて、上述した基板製作方法により基板を製作した。
Claims (15)
- 下記化学式1で表される、着色剤化合物:
[化学式1]
R1 、R 2 、R 4 およびR5は、それぞれ、水素またはハロゲンであり;
R 3 は、下記化学式4の官能基または下記化学式5の官能基であり;
R6は、下記化学式2または3であり;
R7〜R10は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり;
[化学式2]
R11〜R20は、それぞれ、水素、ハロゲン、炭素数1〜10の脂肪族基、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり、
R7〜R20のうちの1つ以上は、炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、炭素数1〜30のアリールチオ基(aryl thio group)、または炭素数1〜30のアルコキシ基であり、
[化学式4]
R 21 、R 22 およびR 23 は、それぞれ独立して、水素、置換または非置換の炭素数1〜20のアルキル基;置換または非置換の炭素数1〜20のアルコキシ基;置換または非置換の炭素数1〜20のヒドロキシアルキル基;置換または非置換の炭素数6〜30のアリール基;置換または非置換の炭素数7〜30のアリールアルキル基;置換または非置換の炭素数7〜30のアルキルアリール基であり;
前記n、n 1 およびn 2 は、整数であり、0≦n≦4、0≦n 1 ≦3、0≦n 2 ≦3である。 - R7〜R10のうちの1つ以上が炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、または炭素数1〜30のアリールチオ基(aryl thio group)であり、
前記R11〜R20は、それぞれ、水素、ハロゲン、または炭素数1〜10の脂肪族基である、請求項1に記載の着色剤化合物。 - R7〜R10は、それぞれ、水素、ハロゲン、または炭素数1〜10の脂肪族基であり、
前記R11〜R14のうちの1つ以上、またはR15〜R20のうちの1つ以上が炭素数1〜30の環または直鎖状のアルキルチオ基(alkyl thio group)、または炭素数1〜30のアリールチオ基(aryl thio group)である、請求項1または2に記載の着色剤化合物。 - 前記R7〜R20のうちの1つ以上は、炭素数3〜6の環または直鎖状のアルキルチオ基(alkyl thio group)である、請求項1から3のいずれか一項に記載の着色剤化合物。
- 上記化学式1で表される化合物は、下記化学式6〜47で表される化合物からなる群から選択される、請求項1に記載の着色剤化合物:
[化学式6]
- 請求項1〜5のいずれか1項に記載の着色剤化合物を含む、着色組成物。
- 染料(Dye)と顔料(Pigment)のうちの少なくとも1つをさらに含む、請求項6に記載の着色組成物。
- 前記染料(Dye)および前記顔料(Pigment)は、それぞれ、黄色、赤色および緑色の中から選択されるいずれか1つの色を示す化合物を1種以上含む、請求項7に記載の着色組成物。
- 前記黄色を示す化合物は、金属−複合体(metal−complex)系化合物、アゾ(azo)系化合物、キノフタロン(quinophthalone)系化合物、イソインドリン(isoindoline)系化合物、およびスチリル(Styryl)系化合物を含む群から選択される1種以上の化合物を含む、請求項8に記載の着色組成物。
- 前記赤色を示す化合物は、金属−複合体(metal−complex)系化合物、アゾ(azo)系化合物、キサンテン(xanthene)系化合物、ジケトピロロピロール(diketopyrrolopyrrole)系化合物、アントラキノン(anthraquinone)系化合物、およびペリレン(Perylene)系化合物を含む群から選択される1種以上の化合物を含む、請求項8に記載の着色組成物。
- 前記緑色を示す化合物は、金属−複合体(metal−complex)系化合物、トリアリールメタン(triarylmethane)系化合物、アントラキノン(anthraquinone)系化合物を含む群から選択される1種以上の化合物を含む、請求項8に記載の着色組成物。
- 前記顔料は、PY129、PY138、PY139、PY150、およびPY185を含む黄色顔料群;PR48、PR48:1、PR48:2、PR48:3、PR48:4、PR177、PR179、PR207、PR254、PR255、PR264およびPR269を含む赤色顔料群;およびPG7、PG36、PG58、およびPG59を含む緑色顔料群;の中から選択される少なくとも1種を含む、請求項8に記載の着色組成物。
- バインダー樹脂、多官能性モノマー、光開始剤、および溶媒をさらに含む、請求項6から12のいずれか一項に記載の着色組成物。
- 請求項6から12のいずれか一項に記載の着色組成物を含む、カラーフィルター。
- 請求項14に記載のカラーフィルターを含む、ディスプレイ装置。
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KR102241994B1 (ko) | 2013-04-18 | 2021-04-19 | 삼성전자주식회사 | 전자 펜을 이용한 기능 제어 방법 및 그 방법을 처리하는 전자 장치 |
KR101711922B1 (ko) * | 2014-04-04 | 2017-03-03 | 제일모직 주식회사 | 신규한 화합물, 상기 화합물을 포함하는 감광성 수지 조성물, 및 컬러 필터 |
WO2015199485A1 (ko) * | 2014-06-27 | 2015-12-30 | 주식회사 엘지화학 | 감광성 수지 조성물 및 이를 이용한 컬러필터 |
KR101711921B1 (ko) * | 2014-09-30 | 2017-03-03 | 삼성에스디아이 주식회사 | 감광성 수지 조성물 및 이를 이용한 컬러필터 |
JP6458522B2 (ja) * | 2015-02-06 | 2019-01-30 | 東洋インキScホールディングス株式会社 | 顔料、カラーフィルタ用着色組成物、およびカラーフィルタ |
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