WO2010002129A2 - Composition de résine photosensible contenant plusieurs photoinitiateurs, et couche de film mince transparente et afficheur à cristaux liquides l'utilisant - Google Patents

Composition de résine photosensible contenant plusieurs photoinitiateurs, et couche de film mince transparente et afficheur à cristaux liquides l'utilisant Download PDF

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Publication number
WO2010002129A2
WO2010002129A2 PCT/KR2009/003324 KR2009003324W WO2010002129A2 WO 2010002129 A2 WO2010002129 A2 WO 2010002129A2 KR 2009003324 W KR2009003324 W KR 2009003324W WO 2010002129 A2 WO2010002129 A2 WO 2010002129A2
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WO
WIPO (PCT)
Prior art keywords
resin composition
photosensitive resin
weight
thin film
photoinitiator
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PCT/KR2009/003324
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English (en)
Korean (ko)
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WO2010002129A3 (fr
Inventor
이건우
김성현
곽상규
오동궁
이창순
조창호
민경훈
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020090054850A external-priority patent/KR101121038B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US12/674,408 priority Critical patent/US8409782B2/en
Priority to CN2009801083066A priority patent/CN101965541A/zh
Priority to JP2010526836A priority patent/JP2011501816A/ja
Publication of WO2010002129A2 publication Critical patent/WO2010002129A2/fr
Publication of WO2010002129A3 publication Critical patent/WO2010002129A3/fr

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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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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

Definitions

  • the present invention relates to a photosensitive resin composition which is excellent in sensitivity by using two or more kinds of photoinitiators having different activation wavelengths and which is easily changed in thickness according to exposure illumination, a transparent thin film layer manufactured therefrom, and a liquid crystal display device including the transparent thin film layer.
  • a photosensitive resin composition which is excellent in sensitivity by using two or more kinds of photoinitiators having different activation wavelengths and which is easily changed in thickness according to exposure illumination, a transparent thin film layer manufactured therefrom, and a liquid crystal display device including the transparent thin film layer.
  • the liquid crystal cell used in the liquid crystal display device is largely composed of a thin film transistor substrate for driving, a color filter for implementing color, and a liquid crystal between the two substrates.
  • the color filter is a substrate which forms a pixel by using a photoetch method using a photosensitive organic material in which pigments are dispersed, and then uses a color ink having three or more transmission-absorption wavelengths to form a color image.
  • an overcoat may be used in the color filter substrate to reduce the step difference of the pixel in some cases, or the column spacer is patterned to maintain a constant gap inside the liquid crystal cell.
  • the photosensitive resin composition in which photoetching is possible the negative composition among them is generally used.
  • the negative composition is a polyfunctional monomer containing two or more polymers and acrylates easily soluble in alkali, and a mixture of a solvent, a surfactant, and an adhesion aid based on a photoinitiator.
  • the photoinitiator is decomposed to generate activating radicals. The activating radical again activates the acrylate contained in the polyfunctional monomer, and the photopolymerization reaction is performed.
  • the solubility in alkali decreases due to the increase in the molecular weight, and thus remains after the development process, thereby enabling the production of a fine pattern using the photoetching method.
  • the sensitivity of the photosensitive composition means the minimum exposure amount (light energy) in which the pattern is stably formed. The lower the value, the shorter the process time and the better the productivity. In particular, in the case of the column spacer maintaining the gap of the liquid crystal cell, it is determined based on the point where the change in the thickness of the pattern greatly decreases according to the exposure amount.
  • the present invention is to solve the above problems of the transparent thin film prepared from the conventional photosensitive resin composition, the sensitivity is increased, but the thickness is easily changed according to the exposure roughness to easily adjust the thickness when using a slit or semi-transmissive mask
  • the objective is to provide the photosensitive resin composition which can be obtained.
  • an object of the present invention is to provide a transparent thin film prepared from the photosensitive resin composition.
  • Another object of the present invention is to provide a liquid crystal display device including the transparent thin film.
  • the present invention by using two or more photoinitiators having a difference in active wave wavelength of 20 nm or more in the photosensitive resin composition, it is excellent in sensitivity and easy to change in thickness according to exposure illumination, and thus can be usefully used as a transparent thin film layer such as a liquid crystal display device. Therefore, the above problems can be solved.
  • the photosensitive resin composition according to the present invention it is easy to change the thickness of the thin film pattern according to the exposure illuminance while excellent in sensitivity, it is easy to control the thickness when using a slit or a semi-transmissive mask, using such a photosensitive resin composition It is advantageous to form column spacers, overcoats, passivation materials and the like of display elements.
  • Fig. 2 is a graph of the results of comparative examples and examples of the present invention observed as a correlation between sensitivity and (pattern saturation thickness-semi-transmissive pattern thickness).
  • the present invention relates to a photosensitive resin composition
  • a photosensitive resin composition comprising two or more kinds of photoinitiators at the same time having a difference of 20 nm or more of active wave wavelengths of the photoinitiator.
  • the present invention comprises at least two photoinitiators, including an alkali-soluble resin, an ethylenically unsaturated compound and a solvent, the content of the component is 1 to 20% by weight alkali-soluble resin, 1 to 20% by weight ethylenically unsaturated compound , 0.05-10% by weight of photoinitiator and 50-95% by weight of solvent.
  • the photoinitiator in the composition according to the present invention includes two or more kinds of photoinitiators having a difference in activation wavelength of 20 nm or more.
  • one embodiment of the present invention is a method using a mixture of Irgacure 369 (Ciba Geigy) having an activation wavelength of 325 nm and Hexa-aryl-bis-imidazole having an activation wavelength of 270 nm.
  • Irgacure OXE-02 (Ciba Geigy) having an activation wavelength of 333 nm and Irgacure 907 (Ciba Geigy) having an activation wavelength of 305 nm may be mixed and used.
  • the photoinitiator is not limited to the above embodiment as long as the activation wavelength meets the object of the present invention, and those known in the art may be used.
  • the photoinitiator is a material having an activation wavelength of 250 to 450 nm, and those having an activation wavelength in the above range can effectively use the wavelengths of mercury vapor arc, carbon arc, xenon arc, and halogen arc which are commonly used in the industry. Preferred at
  • the photoinitiator according to the present invention uses two or more kinds of photoinitiators having a difference in the activation wavelength of 20 nm or more, and the difference in the activation wavelength of the two photoinitiators used is preferably 20 to 100 nm, more preferably 20 to 70 nm.
  • the difference between the activation wavelengths of the two photoinitiators is less than 20 nm, the value of the pattern saturation thickness-slit pattern or the pattern saturation thickness-semi-transmissive pattern thickness, which is an important effect of the present invention, is not sufficiently formed, and when the light source exceeds 100 nm, It is not desirable because there may be a problem that cannot be used efficiently.
  • the content in 0.05 to 10 weight% of the whole photosensitive resin composition.
  • the content of the photoinitiator is less than 0.05% by weight, sufficient photoactive reaction may not be obtained, resulting in uneven pattern formation, and when the content is more than 10% by weight, solubility may be exceeded.
  • the content of the two types of photoinitiator is preferably included in the range of 1: 3 to 3: 1 with respect to each other photoinitiator. If either photoinitiator is included in less than 1/3, it is not preferable because it is difficult to obtain the desired effect in the present invention, and only the properties of the relatively large amount of photoinitiator itself become superior.
  • Alkali-soluble resin in the photosensitive resin composition which concerns on this invention means the polymeric resin which contains a carboxylic acid and shows solubility in alkali, and is not limited to a structure in particular as long as it shows the same effect.
  • a polymethacrylate may be used as a main component, but a copolymer containing methacrylic acid or a polyamic acid may be used.
  • the content of the alkali-soluble resin is preferably used in 1 to 20% by weight of the total photosensitive resin composition. If the content of the alkali-soluble resin is less than 1% by weight, it is difficult and undesirable to form a pattern due to the lack of solubility in a developing solution. When the content of the alkali-soluble resin exceeds 20% by weight, the viscosity of the entire solution becomes too high, which is not preferable because of difficulty in coating.
  • the ethylenically unsaturated compound in the photosensitive resin composition according to the present invention may be a representative example of the following formulas (1) to (4), but is not limited to these as long as it is in accordance with the spirit of the present invention, and those known in the art may be used. have.
  • the ethylenically unsaturated compound is preferably used in an amount of 0.7 to 3 times the weight of the alkali-soluble resin, and less than 0.7 times, it is difficult to expect a sufficient polymerization effect, and if it exceeds 3 times, the relative amount of the polymer resin is insufficient to thin the thin film. It is difficult to form.
  • the content of the ethylenically unsaturated compound is preferably used in 1 to 20% by weight of the total photosensitive resin composition. If the content of the ethylenically unsaturated compound is less than 1% by weight is not preferable because the cross-linking reaction by the light does not proceed, if it exceeds 20% by weight is not preferable because there is a disadvantage that the pattern is difficult to form a poor solubility in alkali.
  • ethylenically unsaturated compounds may be used in the photosensitive resin composition of the present invention.
  • Other functional monomers having ethylenically unsaturated bonds include epoxy acrylates of bisphenol A derivatives, novolak-epoxy acrylates, and urethane-based polyfunctional acrylates, such as U-324A, U15HA, and U-4HA. have.
  • the functional monomer which has the said ethylenically unsaturated double bond can be used individually or in mixture of 2 or more types.
  • one or more solvents may be used as the solvent.
  • solvents include methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, propyl cellosolve, ethylene glycol dimethyl ether, Ethylene glycol diethyl ether, ethylene glycol methylethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol methylethyl ether, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclopentanone , Cyclohexanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl
  • the photosensitive resin composition of the present invention may further include one or more additives such as a curing accelerator, a thermal polymerization inhibitor, a plasticizer, an adhesion promoter, a filler, or a surfactant as necessary.
  • additives such as a curing accelerator, a thermal polymerization inhibitor, a plasticizer, an adhesion promoter, a filler, or a surfactant as necessary.
  • cure accelerators examples include 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, and 2- One selected from the group consisting of mercapto-4,6-dimethylaminopyridine, but is not limited thereto, and curing accelerators known in the art may be used.
  • thermal polymerization inhibitor examples include p-anisole, hydroquinone, and the like, but are not limited thereto, and thermal polymerization inhibitors known in the art may be used.
  • plasticizers adhesion promoters, fillers, surfactants and the like can also be used for all compounds that can be included in conventional photosensitive resin compositions.
  • the photosensitive resin composition according to the present invention may be applied to a support such as a metal, paper, glass, or plastic base by using a roll coater, a curtain coater, a spin coater, a slot die coater, various printing methods, or a deposition method. It is also possible to transfer onto another support after being applied on the support, or to the second support after being applied to the first support and then to a blanket or the like, and the application method is not particularly limited. .
  • mercury vapor arc, carbon arc, xenon arc, halogen arc, etc. which emit light having a wavelength of 250 to 450 nm may be used, but are not particularly limited thereto. Any known in the art can be used.
  • the photosensitive resin composition according to the present invention can be used for the production of a photocurable paint, a photocurable ink, a transparent photosensitive composition for preparing an LCD color filter, a pigment dispersion photosensitive resin composition, a photosensitive resin composition for forming a light shielding film of an LCD or an organic light emitting diode, There is no restriction in particular in the use.
  • this invention provides the transparent thin film layer for liquid crystal display devices manufactured using said photosensitive resin composition.
  • the transparent thin film layer for the liquid crystal display device may be manufactured through a general manufacturing method known in the art, except for using the photosensitive resin composition according to the present invention.
  • the present invention provides a liquid crystal display device including the transparent thin film layer for the liquid crystal display device.
  • the liquid crystal display device may be manufactured by a general manufacturing method known in the art, except that the liquid crystal display device is manufactured by including a transparent thin film layer for a liquid crystal display device manufactured using the photosensitive resin composition according to the present invention.
  • the following photosensitive resin composition was used to form the column spacer. 8 parts by weight of BzMA / MAA (molar ratio: 70/30, Mw: 24,000) as the alkali-soluble resin binder, 16 parts by weight of dipentaerythritol hexaacrylate as a polymerizable compound, 2-benzyl-2-dimethylamino-1- as a photoinitiator 1 part by weight of (4-morpholinophenyl) -butan-1-one (trade name Irgacure-369, Ciba Geigy) and 1 part by weight of hexa-aryl-bis-imidazole (Aldrich), and PGMEA 79 weight with an organic solvent.
  • the portions were mixed for 3 hours using a shaker.
  • the mixed photosensitive solution was filtered using a 5 micron filter, spin-coated to glass, and subjected to electrothermal treatment at about 100 ° C. for 2 minutes to form a uniform film having a thickness of about 3.0 ⁇ m.
  • the film has a 100% transmittance and a 15 ⁇ m circular isolated pattern photomask and a 15 ⁇ m circular independent pattern with a chromium evaporated thin film adjusted to 10% transmittance.
  • the pattern was developed with an aqueous KOH alkali solution of pH 11.3 to 11.7 and washed with deionized water. This was followed by post-heat treatment at 200 ° C. for about 50 minutes to form a spacer pattern.
  • the thickness of the pattern thus formed is measured to define the starting point of the region where the thickness no longer increases in accordance with the exposure amount. Therefore, since a lower value is obtained, it means that the pattern is stably formed even with a small amount of light energy.
  • photoinitiator 1.5 parts by weight of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (trade name Irgacure-369, Ciba Geigy) and hexa-aryl-bis-imidazole (Aldrich ) was used in the same manner as in Example 1 except that 1.5 parts by weight of the mixture was used to form a spacer pattern.
  • Example 2 The same method as in Example 1 except that 1 part by weight of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (trade name Irgacure-369, manufactured by Ciba Geigy) was used as the photoinitiator.
  • the spacer pattern was formed.
  • Example 2 The same method as in Example 1 except that 1.5 parts by weight of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (trade name Irgacure-369, manufactured by Ciba Geigy) was used as the photoinitiator.
  • the spacer pattern was formed.
  • a spacer pattern was formed in the same manner as in Example 1, except that 1 part by weight of hexa-aryl-bis-imidazole (Aldrich) was used as a photoinitiator.
  • a spacer pattern was formed in the same manner as in Example 1, except that 1.5 parts by weight of hexa-aryl-bis-imidazole (Aldrich) was used as the photoinitiator.
  • a spacer pattern was formed in the same manner as in Example 1, except that 1 part by weight of 2-Methyl 1- [4- (methylthio) phenyl] 2-morpholinopropan-1-one (trade name Irgacure 907, Ciba Geigy) was used as the photoinitiator. .
  • a spacer pattern was formed in the same manner as in Example 1, except that 1.5 parts by weight of 2-Methyl 1- [4- (methylthio) phenyl] 2-morpholinopropan-1-one (trade name Irgacure 907, manufactured by Ciba Geigy) was used as the photoinitiator. .
  • ethanone 1- [9-ethyl-6- (2-methylbenzyl) -9H-carbazol-3-yl] -1- (0-acetyloxime) (trade name Irgacure OXE-02, Ciba Geigy) as a photoinitiator and 2 Spacer pattern in the same manner as in Example 1, except that 1 part by weight of -benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (trade name Irgacure-369, manufactured by Ciba Geigy) Formed.
  • the pattern saturation is improved as the sensitivity is improved.
  • Thickness-slit pattern thickness or pattern saturation thickness-value of semi-transmissive pattern thickness decreases, but in the case of using two or more photoinitiators in which the difference in active wave wavelengths is 20 nm or more according to an embodiment of the present invention, the sensitivity is maintained. It can be seen that the value of the pattern saturation thickness-slit pattern thickness or the pattern saturation thickness-semi-transmissive pattern thickness is high.
  • the thickness of the thin film pattern according to the exposure illuminance is easy while the sensitivity of the photosensitive resin composition is easy, so that when the slit or the semi-transmissive mask is used, the thickness can be easily adjusted. It is advantageous to form column spacers, overcoats, passivation materials and the like of display elements.

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  • General Physics & Mathematics (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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Abstract

L'invention concerne une composition de résine photosensible contenant: plusieurs photoinitiateurs avec différentes longueurs d'onde d'activation, une couche de film mince transparente pour afficheur à cristaux liquides préparé à l'aide de la composition de résine photosensible, et un afficheur à cristaux liquides préparé à l'aide de la couche fine transparente. Du fait de l'utilisation de la composition de résine photosensible contenant au moins deux types de photoinitiateurs, la différence des longueurs d'onde d'activation des photoinitiateurs étant d'au moins 20nm, la sensibilité augmente et l'épaisseur est facilement régulée en fonction de l'éclairage d'exposition. En conséquence, l'invention concerne la composition de résine photosensible susceptible de facilement réguler l'épaisseur lorsque des fentes ou des masques semi-transparents sont utilisés.
PCT/KR2009/003324 2008-07-01 2009-06-22 Composition de résine photosensible contenant plusieurs photoinitiateurs, et couche de film mince transparente et afficheur à cristaux liquides l'utilisant WO2010002129A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US12/674,408 US8409782B2 (en) 2008-07-01 2009-06-22 Photoresist composition comprising photoinitiators, and transparent thin film and liquid crystal display device using the composition
CN2009801083066A CN101965541A (zh) 2008-07-01 2009-06-22 含有多种光敏引发剂的光敏树脂组合物和使用该光敏树脂组合物的透明薄膜层和液晶显示器
JP2010526836A JP2011501816A (ja) 2008-07-01 2009-06-22 複数の光開始剤を含む感光性樹脂組成物、これを用いた透明薄膜層及び液晶表示装置

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2008-0063313 2008-07-01
KR20080063313 2008-07-01
KR1020090054850A KR101121038B1 (ko) 2008-07-01 2009-06-19 복수의 광개시제를 포함한 감광성 수지 조성물, 이를 이용한 투명 박막층 및 액정 표시 장치
KR10-2009-0054850 2009-06-19

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WO2010002129A2 true WO2010002129A2 (fr) 2010-01-07
WO2010002129A3 WO2010002129A3 (fr) 2010-03-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4849197B1 (ja) * 2010-07-30 2012-01-11 日立化成工業株式会社 感光性樹脂組成物、並びに、これを用いた感光性エレメント、レジストパターン製造方法、リードフレームの製造方法、プリント配線板、及びプリント配線板の製造方法
KR20160002040A (ko) 2014-06-30 2016-01-07 주식회사 엘지화학 감광성 수지 조성물

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KR20040007700A (ko) * 2001-06-11 2004-01-24 시바 스페셜티 케미칼스 홀딩 인크. 결합된 구조를 가지는 옥심 에스테르 광개시제
KR20050059584A (ko) * 2003-12-15 2005-06-21 주식회사 코오롱 액정 표시 소자의 칼럼 스페이서용 감광성 수지 조성물
KR100736295B1 (ko) * 2005-02-09 2007-07-06 다이요 잉키 세이조 가부시키가이샤 표시 패널용 감광성 수지 조성물, 및 그의 경화물 및 표시패널용 스페이서
KR100793946B1 (ko) * 2006-11-17 2008-01-16 제일모직주식회사 액정표시소자　칼럼 스페이서용 감광성　수지 조성물, 이를이용한 액정표시소자 칼럼 스페이서의 제조방법,액정표시소자용 칼럼 스페이서 및 이를 포함하는디스플레이 장치

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4849197B1 (ja) * 2010-07-30 2012-01-11 日立化成工業株式会社 感光性樹脂組成物、並びに、これを用いた感光性エレメント、レジストパターン製造方法、リードフレームの製造方法、プリント配線板、及びプリント配線板の製造方法
WO2012014580A1 (fr) * 2010-07-30 2012-02-02 日立化成工業株式会社 Composition de résine photosensible, élément photosensible l'utilisant, procédé de formation d'un motif de réserve, procédé de production d'une grille de connexion, carte de câblage imprimé et procédé de production de carte de câblage imprimé
KR20160002040A (ko) 2014-06-30 2016-01-07 주식회사 엘지화학 감광성 수지 조성물

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