JP2009138198A - Alkali-soluble binder resin, production method for it, and photosensitive resin composition containing it - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an alkali-soluble binder resin, a production method for it, and a transparent photosensitive resin composition used in production of a color filter for a liquid crystal display. <P>SOLUTION: The alkali-soluble binder resin contains no carboxylic acid but contains an epoxy group. The photosensitive resin composition comprising the alkali-soluble binder resin has excellent storage stability, prevents a minute pattern from being washed away during a developing process, and reduces an undercut on pattern formation. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an alkali-soluble binder resin, a method for producing the same, and a transparent photosensitive resin composition used for producing a color filter of a liquid crystal display device including the same, and more particularly, a side chain. A photosensitive composition containing an alkali-soluble binder resin that does not contain an acid is excellent in storage stability, can prevent a small pattern from being lost during the development process, and can reduce undercutting during pattern formation.

  The structure of a liquid crystal cell used for a liquid crystal display element is roughly divided into a thin film transistor substrate for driving, a color filter for realizing color, and a liquid crystal between two substrates. The color filter forms a pattern by a photolithographic method using a photosensitive organic material in which pigments are dispersed, and then uses color inks having three or more transmission-absorption wavelengths in order to realize a color image. A substrate to be formed. In addition to the pixels, an overcoat is used on the color filter substrate to reduce the level difference of the pixels depending on the case, or column spacers are patterned to maintain a constant spacing inside the liquid crystal cell.

  When forming an overcoat or patterning a column spacer, a photosensitive resin composition capable of photolithography, in particular, a negative composition is generally used, and alkali solubility is imparted to such a composition. For this purpose, binders containing carboxylic acids, in particular carboxylic acids, have been used.

  However, when carboxylic acid is included, there is a problem that the viscosity of the solution increases with the passage of time because the binder polymer reacts with another binder polymer, a crosslinking agent, or an adhesive preparation to cause crosslinking.

  When the viscosity of the solution increases, a change in thickness occurs when the film is applied, so that it becomes difficult to adjust the process conditions. Therefore, there is a method of refrigerated storage of the solution at around 5 ° C., but this is not preferable because of incidental costs associated with the storage location and refrigeration facility.

  In addition, when the carboxylic acid is contained in the binder itself, the degree of dissolution with respect to alkali is excessively increased and undercut occurs during the development process, thereby causing a disadvantage that a small pattern of 10 microns or less is washed away. There is. In order to prevent such a phenomenon, there is a method of lowering the temperature of the alkaline aqueous solution used as the developer or lengthening the pre-heat treatment time, but this also costs the costs associated with changing and optimizing the process conditions. There is a drawback that it is bulky.

  The present invention was made in order to solve the above-described problems of the conventional alkali-soluble binder resin containing a carboxylic acid, and the object of the present invention is to provide a novel alkali-soluble binder contained in a photosensitive resin composition. It is in providing resin and its manufacturing method.

  Another object of the present invention is to provide a photosensitive resin composition containing the alkali-soluble binder resin as described above.

  In the present invention, in order to impart alkali solubility to the binder resin contained in the photosensitive resin composition, the structure containing carboxylic acid does not contain carboxylic acid and is designed to contain an epoxy group as described above. The problem can be solved.

  The photosensitive resin composition according to the present invention has an effect that the viscosity does not increase even when stored for a long time, and even in the case of a small pattern, it does not flow out during the developing process, and the occurrence of undercut is suppressed. In addition, the photosensitive resin composition according to the present invention improves the storage stability of the photosensitive resin composition by using a polymer resin compound containing no carboxylic acid as a binder resin, and has a small pattern during the development process. This is effective for curing column spacers, overcoats, passivation materials, etc. for liquid crystal display elements, as well as reducing the defective rate during the process. Can do.

The alkali-soluble binder resin of the present invention is represented by the following general formula 1.

In the above formula, R _{1 to} R ₃ are the same as or different from each other, each of which is a hydrogen atom or a methyl group, and the total of each repeating unit l, m, n is assumed to be 100 mol%. when the sum of l and m is 50 to 85 mol%, n is 15 to 50 mol%, Sp is _-C k H _{2k -} an alkylene group represented by, k = 2 to 5 within Has the value of

  The method for producing an alkali-soluble binder resin of the present invention includes a step of copolymerizing benzyl acrylate or benzyl methacrylate, an acrylic monomer containing an epoxy group, and an acrylic monomer containing a hydroxy group. .

  The photosensitive resin composition of the present invention comprises 1 to 20% by weight of an alkali-soluble binder resin represented by the general formula 1, 1 to 20% by weight of a polymerizable compound having an ethylenically unsaturated bond, and a photoinitiator 0. 0.05% to 10% by weight and 10% to 95% by weight of solvent.

  Hereinafter, the present invention will be described in more detail.

  The alkali-soluble binder resin according to the present invention is a compound represented by the general formula 1.

  In the binder resin represented by the general formula 1, l, m, and n represent repeating units, l is an acrylic monomer containing a benzene group selected from benzyl acrylate or benzyl methacrylate, and m is an acrylic containing an epoxy group. A monomer, glycidyl acrylate or glycidyl methacrylate, and n is an acrylic monomer containing a hydroxy group, which represents hydroxyethyl acrylate or methacrylate. Here, when the sum of l, m, and n is assumed to be 100 mol%, the sum of l and m is preferably 50 to 85 mol%, and n is preferably 15 to 50 mol%. In particular, n must have a value of 15 to 50 mol% of l + m + n. If it is less than 15 mol%, the developing characteristics deteriorate, and if it exceeds 50 mol%, the viscosity increases due to hydrogen bonding. Has the disadvantage of becoming difficult to handle.

  The alkali-soluble binder resin represented by the general formula 1 according to the present invention does not contain a carboxylic acid but contains an epoxy group and the like, and is soluble in an alkali developer without containing the carboxylic acid. It is characterized by having. However, other monomers can be further copolymerized and used as long as the effects of the present invention are not adversely affected. For example, the monomer is selected from the group consisting of styrene, methyl methacrylate, N-phenylmaleimide, and methyl acrylate. One or more reactive monomers in repeating units. The reactive monomer can be contained within 30 mol% in the alkali-soluble binder resin.

  Meanwhile, the method for producing the alkali-soluble binder resin includes a step of copolymerizing an acrylic monomer containing a benzene group, an acrylic monomer containing an epoxy group, and an acrylic monomer containing a hydroxy group.

  The copolymerization method can be carried out by a usual method, preferably a radical reaction among them. Specifically, after dissolving a polymerization initiator in a solvent, benzyl acrylate or benzyl methacrylate or hydroxyethyl acrylate is used here. Alternatively, hydroxyethyl methacrylate, and glycidyl acrylate or glycidyl methacrylate are added and maintained at 30 to 100 ° C. in a nitrogen atmosphere and reacted for 10 to 15 hours to obtain an alkali-soluble binder resin.

  Examples of the polymerization initiator used in the radical polymerization include benzoic peroxide (Benzoic-Peroxide, BPO), di-t-butyl-peroxide (Di-T-Butyl-Peroxide, DTBPO), cumene-hydroxide. Peroxide (Cumene-Hydroperoxide, CHPO), t-butyl-hydroperoxide (t-Butyl-Hydroperoxide), t-Butyl-Peroxy-2-ethylhexanoate (t-Butyl-Peroxy-2-Ethylhexanoate), t-Butyl -Peroxy-benzoate (t-Butyl-Peroxy-Benzoate), azobis-dimethyl-valeronitrile (Azobis-Dimethyl-valeronitile, V-65), azobis-isobutyronitrile (Azobis-isob) 1 or more selected from the group such as utilontriel AIBN), but is not particularly limited as long as the polymerization initiation effect is obtained.

  On the other hand, the alkali-soluble binder resin represented by the general formula 1 contains styrene, methyl methacrylate, N-phenylmaleimide, and methyl acrylate in order to improve heat resistance or chemical resistance without departing from the spirit of the present invention. It is also possible to add one or more reactive monomers selected from the group consisting of and further copolymerize them.

  The alkali-soluble binder resin according to the present invention obtained as described above preferably has a weight average molecular weight of 1,000 to 50,000, and when the molecular weight is less than 1,000, it is difficult to form a thin film. In the case where it exceeds 1, there is a drawback that it is difficult to handle because of its high viscosity.

  On the other hand, the present invention comprises 1 to 20% by weight of an alkali-soluble binder resin having the above properties, 1 to 20% by weight of a polymerizable compound having an ethylenically unsaturated bond, 0.05 to 10% by weight of a photoinitiator, And an alkali-soluble photosensitive resin composition containing 10 to 95% by weight of a solvent.

前記式中、ｌ、ｍ、ｎおよびＳｐは前記一般式１で定義したことと同一である。

前記式中、ｌ、ｍ、ｎおよびＳｐは前記一般式１で定義したことと同一である。 In the photosensitive resin composition according to the present invention, the alkali-soluble binder resin does not contain a monomer containing an organic acid such as carboxylic acid, and can be specifically represented by the following general formulas 2 and 3. .

In the above formula, l, m, n and Sp are the same as defined in the general formula 1.

In the above formula, l, m, n and Sp are the same as defined in the general formula 1.

  The alkali-soluble binder resin as described above is preferably contained in an amount of 1 to 20% by weight based on the total weight of the photosensitive resin composition in order to form a thin film having a thickness of 1 to 100 microns. When the amount is less than 1% by weight, the thin film is not formed. When the amount exceeds 20% by weight, the viscosity increases and the thin film is formed very thick.

  Further, in the photosensitive resin composition according to the present invention, examples of the polymerizable compound having an ethylenically unsaturated bond include compounds represented by the following general formulas 4 to 7, which conform to the spirit of the present invention. As long as it does, it is not limited to these, What is known in the said technical field etc. can be used.

Since the polymerizable compound having an ethylenically unsaturated bond does not contain an epoxy group, it is possible to use a structure containing an organic acid as in the following general formulas 5 and 7, unlike the binder resin. It is.

  The polymerizable compound having an ethylenically unsaturated bond is preferably used in an amount of 1 to 20% by weight, and if it is less than 1% by weight, it is difficult to expect a sufficient polymerization effect, and if it exceeds 20% by weight, it is alkali-soluble. Since the relative amount of the binder resin is insufficient, there is a drawback that it is difficult to form a thin film.

  Specific examples of other polymerizable compounds in addition to the polymerizable compound having an ethylenically unsaturated bond represented by the above general formula include KAYARAD DPCA-20, KAYARAD DPCA- as the form introduced into dipentaerythritol. 30, KAYARAD DPCA-60, KAYARAD DPCA-120, and the like, KAYARAD TC-110S introduced into tetrahydrofurfuryl acrylate, KAYARAD HX-220, KAYARAD HK-620 introduced into neopentyl glycol hydroxypivalate, and the like. It is a functional monomer having an ethylenically unsaturated bond. Other functional monomers include bisphenol A derivative epoxy acrylate, novolac-epoxy acrylate, urethane-based polyfunctional acrylates such as U-324A, U15HA, U-4HA, etc. There is. The functional monomer having an ethylenically unsaturated double bond can be used alone or in admixture of two or more.

  In the photosensitive resin composition according to the present invention, as the photoactive radical initiator, one or two or more kinds can be mixed and used. As an example, 2,4-trichloromethyl- (4 ′ Triazine compounds such as 2-methoxyphenyl) -6-triazine, biimidazole compounds such as 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, Acetophenone compounds such as hydroxy-2-methyl-1-phenylpropan-1-one, benzophenone compounds such as 4,4′-bis (dimethylamino) benzophenone, thioxanthones such as 2,4-diethylthioxanthone Compounds, phosphine oxide compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 3,3′-carbonyl-7- Examples include coumarin compounds such as (diethylamino) coumarin, O-acyloxime compounds such as Irgacure OXE-01 and OXE-02 manufactured by Ciba Geigy, but are not particularly limited thereto. Those known in the field can be used. The content is preferably 0.05 to 10% by weight based on the total weight of the photosensitive resin composition.

  In the photosensitive resin composition according to the present invention, one or a mixture of two or more kinds of solvents can be used. Examples thereof include methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, propyl cellosolve, ethylene glycol dimethyl ether, ethylene. Glycol diethyl ether, ethylene glycol methyl ethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol methyl ethyl 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 One selected from the group consisting of propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, and dipropylene glycol monomethyl ether, but is not necessarily limited thereto, and is known in the art Etc. can be used.

  The photosensitive resin composition of the present invention may further contain 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. .

  Examples of such curing accelerators include 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, and 2-mercapto-4,6. -It is selected from the group consisting of dimethylaminopyridine, but is not necessarily limited thereto, and those known in the art can be used.

  Examples of the thermal polymerization inhibitor include p-anisole and hydroquinone, but are not necessarily limited thereto, and those known in the art can be used.

  As the plasticizer, adhesion promoter, filler, surfactant and the like, all compounds contained in the conventional photosensitive resin composition can be used.

  The photosensitive resin composition according to the present invention uses a method such as a roll coating method, a curtain coating method, a spin coating method, a slot-die coating method, various printing methods, a deposition method, and the like. It can be applied to a support such as glass or plastic substrate.

  In addition, after coating on the support, it may be transferred to another support, or may be transferred to the first support, and then transferred to a blanket or the like and then transferred to the second support again. The application method is not particularly limited.

  Examples of the light source for curing the photosensitive resin composition according to the present invention include mercury vapor arc, carbon arc, xenon arc, and halogen arc that emit light having a wavelength of 250 to 450 nm. However, it is not particularly limited to this, and those known in the art can be used.

  The photosensitive resin composition according to the present invention is a photocurable coating, a photocurable ink, a transparent photosensitive composition for producing an LCD color filter, a pigment-dispersed photosensitive resin composition, a light-shielding film for an LCD or an organic light-emitting diode. There is no restriction | limiting in particular for the use.

  In addition, this invention provides the transparent thin film layer for liquid crystal display devices manufactured using the photosensitive resin composition which concerns on this invention. The transparent thin film layer for the liquid crystal display device can be manufactured by a general manufacturing method known in the technical field except that the photosensitive resin composition according to the present invention is used.

In addition, this invention provides the liquid crystal display device characterized by including the said transparent thin film layer for liquid crystal display devices. The liquid crystal display device is a general manufacture known in the art except that it includes a transparent thin film layer for a liquid crystal display device manufactured using the photosensitive resin composition according to the present invention. It can be manufactured by a method.
(Embodiment)

The following examples illustrate the invention in more detail. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited by these examples.
(Synthesis Example 1)

Azobis-dimethyl-valeronitrile (V-65) as a polymerization initiator was dissolved in diethylene glycol methyl ethyl ether, and then benzyl methacrylate, glycidyl methacrylate, and hydroxyethyl methacrylate were added in a molar ratio of 35:40:25 to form nitrogen. The alkali-soluble binder resin was obtained by maintaining 50 to 70 ° C. in the atmosphere and reacting for 10 to 14 hours. The produced alkali-soluble binder resin had a weight average molecular weight of 19,500.
(Synthesis Example 2)

This was prepared in the same manner as in Synthesis Example 1 except that the molar ratio of benzyl methacrylate, glycidyl methacrylate and hydroxyethyl methacrylate was 29:43:28 and the reaction temperature was 40 to 50 ° C. The average molecular weight was 13,100.
(Synthesis Example 3)

Azobis-dimethyl-valeronitrile (V-65) as a polymerization initiator was dissolved in diethylene glycol methyl ethyl ether, and then benzyl methacrylate, glycidyl methacrylate, and hydroxyethyl acrylate were added at a molar ratio of 35:40:25 to form nitrogen. The alkali-soluble binder resin was obtained by maintaining 50 to 70 ° C. in the atmosphere and reacting for 10 to 14 hours. The produced alkali-soluble binder resin had a weight average molecular weight of 19,800.
(Synthesis Example 4)

The alkali-soluble resin produced by the same method as in Synthesis Example 3 except that the reaction temperature was 40 to 50 ° C. was 13,300.
(Synthesis Example 5)

Alkali-soluble resin produced in the same manner as in Synthesis Example 1 except that benzyl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, and styrene were added in a molar ratio of 30: 35: 25: 10 as monomers. The weight average molecular weight of this product was 19,100.
(Synthesis Example 6)

Alkali-soluble resin produced in the same manner as in Synthesis Example 3 except that benzyl methacrylate, glycidyl methacrylate, hydroxyethyl acrylate, and styrene are added in a molar ratio of 30: 35: 25: 10 as monomers. The weight average molecular weight of was 19,300.
(Example 1)

  8 parts by weight of the alkali-soluble binder resin according to Synthesis Example 1, 16 parts by weight of the polymerizable compound of the general formula 4, 1 part by weight of Irgacure OXE-02 from Ciba Geigy as a photopolymerization initiator and 75 parts by weight of cyclohexanone as an organic solvent. Mix for 3 hours using a shaker. The mixed photosensitive solution is filtered using a 5 micron filter, spin-coated on glass, and pre-heated at about 100 ° C. for 2 minutes to form a uniform film having a thickness of about 4 microns. I let you.

  The film was exposed under a high-pressure mercury lamp using a circular independent pattern type photomask having a diameter of 1 micron interval from 1 to 20 microns, and then the pattern was developed with an aqueous KOH solution between pH 11-12. After washing with deionized water, the pattern on the substrate was observed. In order to examine the extent to which small patterns are washed away, the minimum size pattern (minimum residual pattern) remaining on the glass substrate is judged based on the mask size, and whether an undercut occurs is determined using an electron scanning microscope. By observing the cross section, the degree of undercut generated from a pattern having a diameter of 20 microns was determined as a reference.

In order to measure the storage stability of the transparent photosensitive composition, 20 g of the mixed photosensitive solution was sealed in a 50 mL transparent polyethylene bottle, and then stored in an oven maintained at 45 ° C. for 24 hours. The degree of increase (%) was observed.
(Example 2)

A photosensitive resin composition was produced in the same manner as in Example 1 except that 8 parts by weight of the binder resin produced in Synthesis Example 2 was used as the alkali-soluble binder resin.
Example 3

A photosensitive resin composition was produced in the same manner as in Example 1 except that 8 parts by weight of the binder resin produced in Synthesis Example 3 was used as the alkali-soluble binder resin.
Example 4

A photosensitive resin composition was produced in the same manner as in Example 1 except that 8 parts by weight of the binder resin produced in Synthesis Example 4 was used as the alkali-soluble binder resin.
(Example 5)

A photosensitive resin composition was produced in the same manner as in Example 1 except that 8 parts by weight of the binder resin produced in Synthesis Example 5 was used as the alkali-soluble binder resin.
Example 6

A photosensitive resin composition was produced in the same manner as in Example 1 except that 8 parts by weight of the binder resin produced in Synthesis Example 6 was used as the alkali-soluble binder resin.
(Example 7)

A photosensitive resin composition was prepared in the same manner as in Example 1 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 8)

A photosensitive resin composition was produced in the same manner as in Example 2 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
Example 9

A photosensitive resin composition was produced in the same manner as in Example 3 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
Example 10

A photosensitive resin composition was produced in the same manner as in Example 4 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
Example 11

A photosensitive resin composition was produced in the same manner as in Example 5 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 12)

A photosensitive resin composition was produced in the same manner as in Example 6 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 13)

A photosensitive resin composition was prepared in the same manner as in Example 1 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 14)

A photosensitive resin composition was produced in the same manner as in Example 2 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 15)

A photosensitive resin composition was produced in the same manner as in Example 3 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
Example 16

A photosensitive resin composition was produced in the same manner as in Example 4 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 17)

A photosensitive resin composition was produced in the same manner as in Example 5 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 18)

A photosensitive resin composition was produced in the same manner as in Example 6 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 19)

A photosensitive resin composition was produced in the same manner as in Example 1 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 20)

A photosensitive resin composition was produced in the same manner as in Example 2 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 21)

A photosensitive resin composition was produced in the same manner as in Example 3 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 22)

A photosensitive resin composition was produced in the same manner as in Example 4 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 23)

A photosensitive resin composition was produced in the same manner as in Example 5 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Example 24)

A photosensitive resin composition was produced in the same manner as in Example 6 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Comparative Example 1)

(比較例２) Except that 8 parts by weight of a compound represented by the following general formula 8 (l: m: n = 35: 40: 25, weight average molecular weight 20,500) was used as the alkali-soluble binder resin, A photosensitive resin composition was produced in the same manner as in Example 1.

(Comparative Example 2)

A photosensitive resin composition was produced in the same manner as in Comparative Example 1 except that 16 parts by weight of the compound of the general formula 5 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Comparative Example 3)

A photosensitive resin composition was produced in the same manner as in Comparative Example 1 except that 16 parts by weight of the compound of the general formula 6 was used as the polymerizable compound having an ethylenically unsaturated bond.
(Comparative Example 4)

  A photosensitive resin composition was produced in the same manner as in Comparative Example 1 except that 16 parts by weight of the compound of the general formula 7 was used as the polymerizable compound having an ethylenically unsaturated bond.

The results obtained by the examples and comparative examples are shown in Table 1 below.

  As can be seen from the results in Table 1, in the case of Examples 1 to 24, the change in viscosity due to storage is small as compared with Comparative Examples 1 to 4. This is evidence that stability is excellent because there are few side reactions during storage. Moreover, it is excellent in the adhesive force of a pattern that the magnitude | size of the minimum residual pattern observed from Examples 1-24 is smaller than the case of Comparative Examples 1-4, and it can peel between a pattern and a board | substrate. This is because the possible undercut phenomenon is suppressed. When the phenomenon of undercut becomes serious, the area between the pattern and the substrate decreases, so that the adhesive force of the pattern generally decreases. Therefore, when Examples 1-24 are applied, the pattern loss at the time of a process can be suppressed effectively.

Claims (17)

An alkali-soluble binder resin represented by the following general formula 1.

In the above formula, R _{1 to} R ₃ are the same as or different from each other, each of which is a hydrogen atom or a methyl group, and the total of each repeating unit l, m, n is assumed to be 100 mol%. when the sum of l and m is 50 to 85 mol%, n is 15 to 50 mol%, Sp is _-C k H _{2k -} an alkylene group represented by, k = 2 to 5 within Has the value of   The alkali-soluble binder resin according to claim 1, wherein the alkali-soluble binder resin has a weight average molecular weight of 1,000 to 50,000.   2. The alkali-soluble binder resin further includes one or more reactive monomers selected from the group consisting of styrene, methyl methacrylate, N-phenylmaleimide, and methyl acrylate as repeating units. Or alkali-soluble binder resin of Claim 2.   The alkali-soluble binder resin according to claim 3, wherein the reactive monomer is contained within 30 mol% with respect to the total alkali-soluble binder resin.   A method for producing an alkali-soluble binder resin comprising a step of copolymerizing an acrylic monomer containing a benzene group, an acrylic monomer containing an epoxy group, and an acrylic monomer containing a hydroxy group.   6. The method for producing an alkali-soluble binder resin according to claim 5, wherein the acrylic monomer containing a benzene group is selected from the group consisting of benzyl methacrylate and benzyl acrylate.   The method for producing an alkali-soluble binder resin according to claim 5 or 7, wherein the acrylic monomer containing an epoxy group is selected from the group consisting of glycidyl methacrylate and glycidyl acrylate.   The method for producing an alkali-soluble binder resin according to any one of claims 5 to 7, wherein the acrylic monomer containing a hydroxy group is selected from the group consisting of hydroxyethyl methacrylate and hydroxyethyl acrylate. .   9. The resin according to claim 5, further comprising at least one reactive monomer selected from the group consisting of styrene, methyl methacrylate, N-phenylmaleimide, and methyl acrylate as a repeating unit. The manufacturing method of alkali-soluble binder resin in any one of. 1 to 20% by weight of an alkali-soluble binder resin represented by the following general formula 1, 1 to 20% by weight of a polymerizable compound having an ethylenically unsaturated bond, 0.05 to 10% by weight of a photoinitiator, and 10 to 10% of a solvent An alkali-soluble photosensitive resin composition containing 95% by weight.

In the above formula, R _{1 to} R ₃ are the same as or different from each other, each of which is a hydrogen atom or a methyl group, and the total of each repeating unit l, m, n is assumed to be 100 mol%. when the sum of l and m is 50 to 85 mol%, n is 15 to 50 mol%, Sp is _-C k H _{2k -} an alkylene group represented by, k = 2 to 5 within Has the value of 11. The alkali-soluble photosensitive resin composition according to claim 10, wherein the polymerizable compound having an ethylenically unsaturated bond is one or more selected from the group consisting of the following general formulas 4 to 7. object.

  The photoinitiator is one selected from the group consisting of triazine compounds, biimidazole compounds, acetophenone compounds, benzophenone compounds, thioxanthone compounds, thioxanthone compounds, coumarin compounds, and O-acyloxime compounds. It is the above, The alkali-soluble photosensitive resin composition of Claim 10 or Claim 11 characterized by the above-mentioned.   The solvent is methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, propyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol methyl ethyl ether, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclopentanone, cyclohexanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl-3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate , Butyl acetate, and dipro The photosensitive resin composition of the alkali-soluble according to any one of claims 12 to claim 10, wherein the glycol is monomethyl least one member selected from the group consisting of ether.   The composition further comprises at least one additive selected from the group consisting of a curing accelerator, a thermal polymerization inhibitor, a plasticizer, an adhesion promoter, a filler, and a surfactant. The alkali-soluble photosensitive resin composition according to any one of claims 10 to 13.   The result obtained from the alkali-soluble photosensitive resin composition of any one of Claims 10-14.   The result according to claim 15, wherein the resultant product is at least one selected from the group consisting of a photocurable paint, a photocurable ink, a color filter, a pigment dispersion composition, and a light shielding film. object.   A liquid crystal display device comprising the color filter according to claim 16.