CN109856910B - Photosensitive resin composition and application thereof - Google Patents
Photosensitive resin composition and application thereof Download PDFInfo
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Abstract
The present disclosure relates to a photosensitive resin composition and use thereof, the composition comprising: a colorant; an alkali-soluble resin; a polyfunctional monomer compound; a photopolymerization initiator; a nonionic surfactant; and a solvent; wherein the structure of the nonionic surfactant is shown as the formula (1):
in the formula (1), R 1 Is alkylene with carbon number of 1-5, Ar is substituted aryl with carbon number of 10-50, and n is integer of 4-20. The photosensitive resin composition provided by the present disclosure includes a nonionic surfactant, and has good developing performance and storage stability.
Description
Technical Field
The present disclosure relates to a photosensitive resin composition and applications thereof.
Background
The color filter is a key device for realizing colorization of the liquid crystal display, and the performance of the color photoresist used for preparing the color filter directly influences the display effect of the liquid crystal display. As the color purity of liquid crystal displays increases, the developing performance of the coating film inevitably decreases as the concentration of the colorant contained in the photosensitive resin composition (also referred to as a photoresist) increases, and thus the photosensitive resin composition is required to have good developing performance, and the pixel edge formed after exposure and development of the photosensitive resin composition is required to be uniform, and the photosensitive resin composition is required to have good storage stability.
The development property of the photosensitive resin composition is generally improved by improving the development property of the alkali-soluble resin. Generally, the acid value is increased from the structural point of view, which requires the introduction of a large amount of acidic groups during the polymerization. However, increasing the acid value tends to cause problems such as a low molecular weight of the resulting resin and the necessity of using a highly polar solvent during the polymerization, which easily results in poor compatibility between the alkali-soluble resin and the colorant, resulting in a decrease in the stability of the resin composition and even precipitation of precipitates in a short period of time. The acid value is also improved by adding small molecular acid into the photosensitive resin composition, but the amount of the added small molecular acid is not well controlled, the addition is too small, the developing performance cannot be improved, the addition is too much, the pixel edge line is irregular, and the storage stability of the photosensitive resin is reduced.
Disclosure of Invention
In order to solve the above problems, the present disclosure provides a photosensitive resin composition and applies it to a process of manufacturing a color filter. The photosensitive resin composition provided by the present disclosure includes a nonionic surfactant, so that it has good developing properties and storage stability.
The present disclosure provides a photosensitive resin composition, including:
a colorant;
an alkali-soluble resin;
a polyfunctional monomer compound;
a photopolymerization initiator;
a nonionic surfactant; and
a solvent;
wherein the structure of the nonionic surfactant is shown as the formula (1):
in the formula (1), R 1 Is alkylene with carbon number of 1-5, Ar is substituted aryl with carbon number of 10-50, and n is integer of 4-20.
Optionally, R 1 Is ethylene, propylene, butylene, pentylene, 2-methylpropylene or 2-methylbutylene, and n is an integer of 4 to 16.
Optionally, the structure of Ar is represented by formula (2):
in formula (2), the wavy line represents the bonding position of Ar to the O atom in formula (1); q 1 -Q 5 Each independently is a hydrogen atom or a group selected from those represented by the formula (3), and Q 1 -Q 5 Not being hydrogen atoms at the same time;
in formula (3), the triangle represents the bonding position of the group to the benzene ring in formula (2), Q 6 Is hydrogen atom or C1-5 alkyl.
Optionally, Ar contains 3-4 benzene rings.
Optionally, Ar is one of the following substituted aryl groups:
wherein the wavy line represents a bonding position of Ar and the O atom in the formula (1); r 2 -R 10 Each independently is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
Optionally, the content of the colorant is 15-300 parts by weight, the content of the polyfunctional monomer compound is 50-300 parts by weight, the content of the photopolymerization initiator is 0.5-40 parts by weight, the content of the nonionic surfactant is 0.5-40 parts by weight, and the content of the solvent is 800-3000 parts by weight, relative to 100 parts by weight of the alkali-soluble resin.
Optionally, the colorant is pigment red R254, pigment green G58, or pigment blue B15: 6, the alkali soluble resin is acrylic ester alkali soluble resin containing carboxylic acid group; the multifunctional monomer compound is dipentaerythritol hexaacrylate and/or polybasic acid modified pentaerythritol triacrylate, and the photopolymerization initiator is at least one selected from oxime ester photoinitiators, acetophenone photoinitiators, diimidazole photoinitiators, benzophenone photoinitiators and anthraquinone photoinitiators.
Optionally, the solvent is at least one selected from the group consisting of 3-methoxybutyl acetate, diethylene glycol methyl ether acetate, diethylene glycol ethyl ether acetate, diethylene glycol butyl ether acetate, ethylene glycol butyl ether acetate, dipropylene glycol propyl ether, dipropylene glycol butyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol methyl ether, propylene glycol ethyl ether, ethyl 3-ethoxypropionate, ethyl acetate, propyl acetate, cyclohexanone, and ethylene glycol ethyl ether.
Optionally, the composition further comprises at least one of a leveling agent, a silane coupling agent and an ionic surfactant.
The disclosure also provides applications of the provided composition in color filter preparation.
The present disclosure can promote the development of unexposed parts and improve the developability and the liness of a photosensitive resin composition by adding a nonionic surfactant containing a hydrophilic group to the photosensitive resin composition, and at the same time, the storage stability of the photosensitive resin composition containing a small molecular acid or an acidic substance as a development aid is remarkably improved because the nonionic surfactant compound contains an aryl group.
Additional features and advantages of the disclosure will be set forth in the detailed description which follows.
Detailed Description
The following describes in detail specific embodiments of the present disclosure. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.
The present disclosure provides a photosensitive resin composition, comprising:
a colorant;
an alkali-soluble resin;
a polyfunctional monomer compound;
a photopolymerization initiator;
a nonionic surfactant; and
a solvent;
wherein the structure of the nonionic surfactant is shown as the formula (1):
in the formula (1), R 1 Is alkylene with carbon number of 1-5, Ar is substituted aryl with carbon number of 10-50, preferably 22-45, and n is integer of 4-20.
According to the disclosure, R 1 May be a linear or branched alkylene group, e.g. R 1 It may be ethylene, propylene, butylene, pentylene, 2-methylpropylene or 2-methylbutylene, preferably ethylene or propylene, more preferably ethylene.
According to the present disclosure, n is preferably an integer of 4 to 16 from the viewpoint of development speed and system compatibility with the photosensitive resin composition, and when n is less than 4, the hydrophilic group content is less, and improvement of development property of the photosensitive resin composition cannot be achieved, and n is more preferably 10 to 16; when n is greater than 20, a nonionic surfactant remains on the resist film, and the performance of the resist film is affected.
In one embodiment, the structure of Ar may be represented by formula (2):
in formula (2), the wavy line represents the bonding position of Ar to the O atom in formula (1); q 1 -Q 5 May each independently be a hydrogen atom or a group selected from those represented by the formula (3), and Q 1 -Q 5 Not being hydrogen atoms at the same time;
in formula (3), the triangle represents the bonding position of the group to the benzene ring in formula (2), Q 6 Is hydrogen atom or C1-5 alkyl.
According to the present disclosure, Ar preferably contains 3 to 4 benzene rings, further preferably Ar is one of the following substituted aryl groups:
wherein the wavy line represents a bonding position of Ar and the O atom in the formula (1); r 2 -R 10 Each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably a hydrogen atom. In addition, R is 2 -R 10 The substitution position of (a) is directed to the middle of the benzene ring, meaning that it may be linked to any substitutable position of the benzene ring. When Ar in the general formula (1) is any one of M-1 to M-4, the nonionic surfactant compound containing the general formula (1) contains a relatively large rigid group and is greatly sterically hindered or sterically hindered. The steric hindrance is advantageous for maintaining the dispersion state of the system, and plays a positive role in preventing pigment molecule aggregation and photosensitive resin viscosity change, thereby obtaining excellent dispersion storage stability.
The content of each component in the composition is well known to those skilled in the art in light of the present disclosure, for example, the content of the colorant may be 15 to 300 parts by weight, preferably 100-150 parts by weight, the content of the polyfunctional monomer compound may be 50 to 300 parts by weight, preferably 100-200 parts by weight, the content of the photopolymerization initiator (also referred to simply as photoinitiator) may be 0.5 to 40 parts by weight, preferably 1 to 10 parts by weight, the content of the nonionic surfactant may be 0.5 to 40 parts by weight, preferably 1 to 10 parts by weight, and the content of the solvent may be 800-3000 parts by weight, preferably 1500-2800 parts by weight, relative to 100 parts by weight of the alkali soluble resin, which can also be adjusted by those skilled in the art as required.
In accordance with the present disclosure, the colorant, the alkali-soluble resin, the polyfunctional monomer compound, the photopolymerization initiator, and the solvent are well known to those skilled in the art, and for example, the colorant may be pigment red R254, pigment green G58, or pigment blue B15: 6; the alkali soluble resin can be acrylate alkali soluble resin containing a carboxylic acid group; the multifunctional monomer compound is a monomer containing multiple reactive functional groups such as unsaturated double bonds, hydroxyl groups, carboxyl groups, carbonyl groups and the like in a molecule, the addition of the multifunctional monomer compound can realize the formation of clear pixel patterns on an exposed part and prevent the problems of development and demolding and the like, multiple multifunctional monomer compounds which are known in the art and can participate in crosslinking reaction are usually used in a mixed manner, specifically dipentaerythritol hexaacrylate and/or polyacid modified pentaerythritol triacrylate, and the photopolymerization initiator can be at least one selected from oxime ester photoinitiators, acetophenone photoinitiators, diimidazole photoinitiators, benzophenone photoinitiators and anthraquinone photoinitiators; the solvent is used for improving the coating effect of the composition, and preferably comprises a high boiling point solvent with a boiling point of 150-200 ℃ and a low boiling point solvent with a boiling point lower than 150 ℃ from the aspects of environmental protection requirement, membrane surface smoothness and process operation handling property, and the high boiling point solvent and the low boiling point solvent are preferably contained in a weight ratio of (10:90) - (50: 50). The high boiling point solvent is well known to those skilled in the art, and may be, for example, 3-methoxybutyl acetate, diethylene glycol methyl ether acetate, diethylene glycol ethyl ether acetate, diethylene glycol butyl ether acetate, ethyl 3-ethoxypropionate, ethylene glycol butyl ether acetate, dipropylene glycol propyl ether, dipropylene glycol butyl ether, etc., and the low boiling point solvent is well known to those skilled in the art, and may be, for example, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol methyl ether, propylene glycol ethyl ether, ethyl acetate, propyl acetate, cyclohexanone, ethylene glycol ethyl ether, etc. A person skilled in the art may also use a colorant, an alkali-soluble resin, a polyfunctional monomer compound, a photopolymerization initiator, and a solvent other than those enumerated above, and the present disclosure will not be described in detail.
According to the present disclosure, the composition may further include other additives as needed, for example, at least one of a leveling agent, a silane coupling agent and an ionic surfactant, which are well known to those skilled in the art and will not be described in detail in the present disclosure. The composition of the present disclosure may be obtained by mixing the above components, and the mixing manner may be a conventional manner.
The disclosure also provides applications of the composition provided by the disclosure in preparation of color filters. The application can comprise coating, pre-baking, exposing, developing and post-baking the composition on a substrate to obtain a color filter with a pattern and pixels with a specific shape.
The present disclosure is further illustrated by the following examples, but is not limited thereby.
The viscosity in the examples and comparative examples was measured with a BROOKFIELD viscometer (model DV-2), and the film thickness was measured with a BRUKER step meter (model Dektak-XT).
The structural formulas of the nonionic surfactants E1-E4 used in examples 1-4 of the present disclosure are:
examples 1 to 4 and comparative examples 1 to 3
The examples and comparative examples of the present disclosure specifically include the following steps:
1) the components were uniformly mixed in a stirrer according to the formulation of table 1 to form a photosensitive resin composition; of these, examples 1-4 used nonionic surfactants E1-E4, and comparative examples 1-3 used small molecule acids, other types of nonionic surfactants, or no surfactant.
2) The photosensitive resin composition is coated on the surface of a glass substrate to form a film coating.
3) And (3) pre-baking the coated substrate in a dryer to remove the solvent, wherein the pre-baking temperature is 115 ℃ and the pre-baking time is 2 minutes.
4) Covering a mask on the dry film coating, and irradiating with ultraviolet rays to generate photopolymerization reaction with irradiation intensity of 60 MJ/cm 2 。
5) And selecting a developing mode of spraying a developing solution at the temperature of 23 +/-2 ℃, wherein the developing solution is 0.05 weight percent of KOH aqueous solution, spraying for 50 seconds, and washing off the unexposed soluble resin composition by using the developing solution to obtain the required image.
6) Heating and post-baking with a heating device such as a hot plate or an oven at 230 deg.C for 30 min.
7) The photosensitive resin composition is used for measuring viscosity and developing rate, the film thickness of the color filter is measured, and the performance of the color filter and the film thickness are evaluated, wherein the specific evaluation mode is as follows:
a. evaluation of storage stability of photosensitive resin composition
Storage stability includes dispersion stability and viscosity stability.
Dispersion stability: after the photosensitive resin composition was stored at normal temperature of 40 ℃ for one week, the presence or absence of sedimentation was observed, and the evaluation criteria were as follows:
o: no sedimentation;
x: there was a sedimentation.
Viscosity stability: the photosensitive resin composition was stored at room temperature of 40 ℃ for one week, and then the viscosity change was measured, and the evaluation criteria were as follows:
o: no viscosity change or viscosity change less than 0.1 mPa.s;
and (delta): the viscosity became high, but was not significantly changed within 0.1 to 0.5 mPas;
x: a sharp viscosity change above 0.5 mpa · s.
b. Evaluation of development-related Properties
Further evaluating the image formed by the developing method of step 5), the evaluating method comprising:
b1 edge line regularity
Observing the regularity of image lines on the glass substrate by using an optical microscope and a field emission scanning electron microscope:
o: the lines of the image are neat;
and (delta): the lines of the image are irregular and have burrs.
b2 developability
The integrity of the image formation on the glass substrate was observed using an optical microscope, a field emission scanning electron microscope:
o: developing to be clean;
and (delta): a small amount of residual film is arranged at the edge of the graph;
x: the film is not developed completely and has a large amount of residual films;
the specific evaluation results are shown in Table 2.
As can be seen from table 2, the photosensitive resin compositions of examples 1 to 4, which contain the nonionic surfactant of the present disclosure, have a high development rate, good dispersion stability and viscosity stability, and good image development after development, and have clean patterns and regular side lines, and thus can form color filters having excellent image forming effects. From the above results, it is also known that not all nonionic surfactants are suitable for addition to the photosensitive resin composition.
TABLE 1
The specific components in table 1 are as follows:
a: green pigment G58 (produced by DIC chemical Co., Ltd.);
b: methacrylic acid and benzyl methacrylate copolymers; (ii) a
C1: dipentaerythritol hexaacrylate (manufactured by sartomer, analytically pure);
c2: polybasic acid-modified pentaerythritol triacrylate (analytically pure, manufactured by east asian synthesis corporation);
d: OXE-02 (manufactured by BASF corporation);
E1-E4: a nonionic surfactant (manufactured by Kao corporation);
e5: nonionic surfactant octylphenol polyoxyethylene ether (manufactured by dow chemical);
h: 3-bromopropionic acid (manufactured by acros);
f1: AFKA-3600 (leveling agent, manufactured by BASF corporation);
f2: KH570 (silane coupling agent, gamma-methacryloxypropyltrimethoxysilane, carbofuran, analytically pure);
s1: PGMEA (propylene glycol methyl ether acetate, carbofuran, analytical grade);
s2: EEP (ethyl 3-ethoxypropionate, national pharmaceutical group, analytically pure). TABLE 2
Claims (8)
1. A photosensitive resin composition, comprising:
a colorant;
an alkali-soluble resin;
a polyfunctional monomer compound;
a photopolymerization initiator;
a nonionic surfactant; and
a solvent;
wherein the structure of the nonionic surfactant is shown as the formula (1):
in the formula (1), R 1 Is alkylene with carbon number of 1-5, Ar is substituted aryl with carbon number of 10-50, and n is an integer of 4-20;
wherein, the structure of Ar is shown as formula (2):
in formula (2), the wavy line represents the bonding position of Ar to the O atom in formula (1); q 1 -Q 5 Each independently is a hydrogen atom or a group selected from those represented by the formula (3), and Q 1 -Q 5 Not being hydrogen atoms at the same time;
in formula (3), the triangle represents the bonding position of the group to the benzene ring in formula (2), Q 6 Is hydrogen atom or C1-C5 alkyl;
wherein Ar contains 3-4 benzene rings.
2. The composition of claim 1, wherein R 1 Is ethylene, propylene, butylene, pentylene, 2-methylpropylene or 2-methylbutylene, and n is an integer of 4 to 16.
3. The composition of claim 1, wherein Ar is one selected from the following substituted aryl groups:
wherein the wavy line represents a bonding position of Ar and the O atom in the formula (1); r is 2 -R 10 Each independently is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
4. The composition as claimed in claim 1, wherein the colorant is contained in an amount of 15 to 300 parts by weight, the polyfunctional monomer compound is contained in an amount of 50 to 300 parts by weight, the photopolymerization initiator is contained in an amount of 0.5 to 40 parts by weight, the nonionic surfactant is contained in an amount of 0.5 to 40 parts by weight, and the solvent is contained in an amount of 800-3000 parts by weight, with respect to 100 parts by weight of the alkali-soluble resin.
5. The composition of claim 1, wherein the colorant is pigment red R254, pigment green G58, or pigment blue B15: 6, the alkali soluble resin is acrylic ester alkali soluble resin containing carboxylic acid group; the multifunctional monomer compound is dipentaerythritol hexaacrylate and/or polybasic acid modified pentaerythritol triacrylate, and the photopolymerization initiator is at least one selected from oxime ester photoinitiators, acetophenone photoinitiators, diimidazole photoinitiators, benzophenone photoinitiators and anthraquinone photoinitiators.
6. The composition according to claim 1, wherein the solvent is at least one selected from the group consisting of 3-methoxybutyl acetate, diethylene glycol methyl ether acetate, diethylene glycol ethyl ether acetate, diethylene glycol butyl ether acetate, ethylene glycol butyl ether acetate, dipropylene glycol propyl ether, dipropylene glycol butyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol methyl ether, propylene glycol ethyl ether, ethyl 3-ethoxypropionate, ethyl acetate, propyl acetate, cyclohexanone, and ethylene glycol ethyl ether.
7. The composition of claim 1, wherein the composition further comprises at least one of a leveling agent, a silane coupling agent, and an ionic surfactant.
8. Use of a composition according to any one of claims 1 to 7 in the preparation of a color filter.
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| JP2004245906A (en) * | 2003-02-12 | 2004-09-02 | Konica Minolta Holdings Inc | Developing solution for planographic printing plate material and method for processing planographic printing plate material |
| CN1928724A (en) * | 2005-09-05 | 2007-03-14 | 比亚迪股份有限公司 | Photoresistance developer |
| CN101359189A (en) * | 2008-09-17 | 2009-02-04 | 电子科技大学 | Developing solution for positive photosensitive polyimide photoresist |
| CN104231150A (en) * | 2014-08-25 | 2014-12-24 | 北京鼎材科技有限公司 | Alkali-soluble resin polymer and preparation method thereof |
| CN106227003A (en) * | 2016-09-29 | 2016-12-14 | 杭州格林达化学有限公司 | A kind of developer composition and preparation method thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004245906A (en) * | 2003-02-12 | 2004-09-02 | Konica Minolta Holdings Inc | Developing solution for planographic printing plate material and method for processing planographic printing plate material |
| CN1928724A (en) * | 2005-09-05 | 2007-03-14 | 比亚迪股份有限公司 | Photoresistance developer |
| CN101359189A (en) * | 2008-09-17 | 2009-02-04 | 电子科技大学 | Developing solution for positive photosensitive polyimide photoresist |
| CN104231150A (en) * | 2014-08-25 | 2014-12-24 | 北京鼎材科技有限公司 | Alkali-soluble resin polymer and preparation method thereof |
| CN106227003A (en) * | 2016-09-29 | 2016-12-14 | 杭州格林达化学有限公司 | A kind of developer composition and preparation method thereof |
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