CN109856910A - A kind of Photosensitve resin composition and its application - Google Patents
A kind of Photosensitve resin composition and its application Download PDFInfo
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Abstract
This disclosure relates to a kind of Photosensitve resin composition and its application, the composition includes: colorant；Alkali soluble resins；Multi-functional monomeric compound；Photoepolymerizationinitiater initiater；Nonionic surfactant；And solvent；Wherein, shown in the structure of the nonionic surfactant such as formula (1):In formula (1), R1The alkylidene for being 1-5 for carbon number, Ar are the substituted aryl that carbon number is 10-50, and n is the integer of 4-20.The Photosensitve resin composition that the disclosure provides includes nonionic surfactant, has good developing performance and storage stability.
Description
Technical field
This disclosure relates to a kind of Photosensitve resin composition and its application.
Background technique
Colored filter is the Primary Component that liquid crystal display realizes colorization, and is used to prepare the colour of colour filter
Photoresist, performance directly influence the display effect of liquid crystal display.With the high color purity of liquid crystal display, photonasty tree
When the concentration for the colorant that oil/fat composition (being referred to as photoresist) contains is got higher, the developing performance of film necessarily declines, this
It requires photosensitive polymer combination that there is good developing performance, and requires the Photosensitve resin composition by exposure development
After to be formed by pixel sideline neat, and photosensitive polymer combination has good shelf-stability.
The general developing performance that photosensitive polymer combination is improved using the developing performance for improving alkali soluble resins.From knot
It is usually to improve acid value in terms of structure, this needs to introduce a large amount of acidic-group in the course of the polymerization process.But improve acid value often
Many problems can be brought, for example the molecular weight of gained resin is relatively low, highly polar solvent must be used in polymerization process, this is easily
Cause alkali soluble resins and colorant matching to be deteriorated, so as to cause the reduction of resin combination stability, or even has in a short time
Sediment is precipitated.Also have by the way that small molecule acid is added in photosensitive polymer combination and improve acid value, but be added small
The bad control of amount of molecule acid is added very little, cannot promote developing performance, the too many pixel sideline that will lead to again of addition is uneven, sense
Photosensitiveness resin storage stability reduces.
Summary of the invention
In order to solve problem above, the disclosure provides a kind of Photosensitve resin composition and applies it to colored filter
In preparation process.The Photosensitve resin composition that the disclosure provides includes nonionic surfactant, makes it have good development
Performance and storage stability.
The disclosure provides a kind of Photosensitve resin composition, and the composition includes:
Colorant；
Alkali soluble resins；
Multi-functional monomeric compound；
Photoepolymerizationinitiater initiater；
Nonionic surfactant；And
Solvent；
Wherein, shown in the structure of the nonionic surfactant such as formula (1):
In formula (1), R1The alkylidene for being 1-5 for carbon number, Ar are the substituted aryl that carbon number is 10-50, and n is the whole of 4-20
Number.
Optionally, R1It is for ethylidene, propylidene, butylidene, pentylidene, 2- methyl propylene or 2- methylbutylene, n
The integer of 4-16.
Optionally, shown in the structure of Ar such as formula (2):
In formula (2), wave represents the bonding position of O atom in Ar and formula (1)；Q1-Q5It is each independently hydrogen atom
Or it is selected from group shown in formula (3), and Q1-Q5It is not simultaneously hydrogen atom；
In formula (3), triangle represents the bonding position of phenyl ring in the group and formula (2), Q6It is for hydrogen atom or carbon number
The alkyl of 1-5.
Optionally, Ar contains 3-4 phenyl ring.
Optionally, Ar is selected from one of following substituted aryl:
Wherein, wave represents the bonding position of O atom in Ar and formula (1)；R2-R10It is each independently hydrogen atom or carbon
Number is the alkyl of 1-5.
Optionally, the alkali soluble resins relative to 100 parts by weight, the content of the colorant are 15-300 parts by weight, institute
The content for stating multi-functional monomeric compound is 50-300 parts by weight, and the content of the Photoepolymerizationinitiater initiater is 0.5-40 weight
Part, 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.
Optionally, the colorant is paratonere R254, naphthol green G58 or pigment blue B15:6, the alkali soluble resins are
Esters of acrylic acid alkali soluble resins containing carboxylic acid group；The multi-functional monomeric compound is dipentaerythritol hexaacrylate
And/or modified by polyacid pentaerythritol triacrylate, the Photoepolymerizationinitiater initiater are selected from oxime ester lightlike initiating agent, acetophenone
At least one of photoinitiator, diimidazole photoinitiator, Benzophenone-type light initiator and anthraquinone photoinitiator.
Optionally, the solvent is selected from acetic acid 3- methoxybutyl, diethylene glycol dimethyl ether acetate, diethylene glycol ether
Acetate, butyl acetate, 2-Butoxyethyl acetate, dipropylene glycol propyl ether, dipropylene, propylene glycol first
Ether acetate, propylene-glycol ethyl ether acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, 3- ethoxyl ethyl propionate, ethyl acetate, second
At least one of propyl propionate, cyclohexanone and ethylene glycol ethyl ether.
Optionally, the composition further includes at least one in levelling agent, silane coupling agent and ionic surfactant
Kind.
The disclosure also provides application of the provided composition in colored filter preparation.
The disclosure in photosensitive polymer combination by being added a kind of non-ionic surfactant containing hydrophilic radical
Agent can promote the development at unexposed position, improve the developability of photosensitive polymer combination, sideline uniformity, simultaneously as non-
Ionic surface active agent compound contains aryl, than typically containing the photonasty of small molecule acid or acidic materials as development promoter
The storage stability of resin combination is significantly increased.
Other feature and advantage of the disclosure will the following detailed description will be given in the detailed implementation section.
Specific embodiment
The specific embodiment of the disclosure is described in detail below.It should be understood that described herein specific
Embodiment is only used for describing and explaining the disclosure, is not limited to the disclosure.
The disclosure provides a kind of Photosensitve resin composition, and the composition includes:
Colorant；
Alkali soluble resins；
Multi-functional monomeric compound；
Photoepolymerizationinitiater initiater；
Nonionic surfactant；And
Solvent；
Wherein, shown in the structure of the nonionic surfactant such as formula (1):
In formula (1), R1The alkylidene for being 1-5 for carbon number, Ar are the substituted aryl that carbon number is 10-50, preferably 22-45
Substituted aryl, n be 4-20 integer.
According to the disclosure, R1It can be straight-chain alkyl-sub, or branched alkylidene, such as R1It can be ethylidene, Asia
Propyl, butylidene, pentylidene, 2- methyl propylene or 2- methylbutylene, preferably ethylidene or propylidene, it is more preferably sub-
Ethyl.
According to the disclosure, from the aspect of the Miscibility from developing powder and with Photosensitve resin composition, n is preferably
The integer of 4-16, when n is smaller than 4, hydrophilic radical content is less, cannot reach the developability for improving photosensitive polymer combination
Can, n is more preferably 10-16；When n is bigger than 20, the remaining nonionic surfactant of meeting, influences photoresistance film in photoresistance film
Performance.
The structure of a kind of embodiment, Ar can be as shown in formula (2):
In formula (2), wave represents the bonding position of O atom in Ar and formula (1)；Q1-Q5Hydrogen can be each independently
Atom is selected from group shown in formula (3), and Q1-Q5It is not simultaneously hydrogen atom；
In formula (3), triangle represents the bonding position of phenyl ring in the group and formula (2), Q6It is for hydrogen atom or carbon number
The alkyl of 1-5.
According to the disclosure, Ar preferably comprises 3-4 phenyl ring, it is further preferred that Ar is selected from one of following substituted aryl:
Wherein, wave represents the bonding position of O atom in Ar and formula (1)；R2-R10It is each independently hydrogen atom or carbon
Number is the alkyl of 1-5, preferably hydrogen atom.It should be noted that R2-R10The position of substitution be directed toward phenyl ring among, indicate that it can
With with the phenyl ring arbitrarily can substituted position be connected.When the Ar in general formula (1) is any group in M-1~M-4
When, the non-ionic surfactant compound comprising general formula (1) contains larger rigid radical, there are very large space steric hindrance or stands
Body obstacle.The steric hindrance is conducive to the dispersity of maintenance system, for preventing pigment molecule aggregation and photoresist viscous
Positive effect is played in degree variation, to obtain excellent dispersion storage stability.
According to the disclosure, the content of each component is well-known to those skilled in the art in composition, for example, relative to
The content of the alkali soluble resins of 100 parts by weight, the colorant can be 15-300 parts by weight, preferably 100-150 parts by weight,
The content of the multi-functional monomeric compound can be 50-300 parts by weight, preferably 100-200 parts by weight, the photopolymerization
The content of initiator (can also be referred to as photoinitiator) can be 0.5-40 parts by weight, preferably 1-10 parts by weight, described non-
The content of ionic surface active agent can be 0.5-40 parts by weight, and preferably 1-10 parts by weight, the content of the solvent can be
800-3000 parts by weight, preferably 1500-2800 parts by weight, those skilled in the art can also be adjusted as needed.
According to the disclosure, colorant, alkali soluble resins, multi-functional monomeric compound, Photoepolymerizationinitiater initiater and solvent are equal
It is well known to those skilled in the art, for example, the colorant can be paratonere R254, naphthol green G58 or pigment blue
B15:6；The alkali soluble resins can be the esters of acrylic acid alkali soluble resins containing carboxylic acid group；The multi-functional monomer chemical combination
Object refers in molecule comprising multiple monomers with reactive functional groups such as unsaturated double-bond, hydroxyl, carboxyl, carbonyls, adds more
Functional monomer's compound can be realized exposed portion formed clearly pattern of pixels, prevent development demould the problems such as, usually
It is used in mixed way using a variety of multi-functional monomeric compounds well known in the art that may participate in cross-linking reaction, was specifically as follows for two seasons
Penta tetrol, six acrylate and/or modified by polyacid pentaerythritol triacrylate, the Photoepolymerizationinitiater initiater can for selected from
Oxime ester lightlike initiating agent, acetophenones light trigger, diimidazole photoinitiator, Benzophenone-type light initiator and Anthraquinones light
At least one of initiator；The solvent is used to improve the Painting effect of composition, from environmental requirement, film surface planarization,
From the aspect of technological operation treatability, the solvent preferably includes the high boiling solvent that boiling point is 150-200 DEG C and boiling point is lower than
150 DEG C of low boiling point solvent preferably includes the high boiling solvent and the low boiling point with the weight ratio of (10:90)-(50:50)
Solvent.Wherein the high boiling solvent is well-known to those skilled in the art, such as can be acetic acid 3- methoxybutyl, two
Glycol methyl ether acetate, diethylene glycol ether acetate, butyl acetate, 3- ethoxyl ethyl propionate, second two
Alcohol monobutyl ether acetate, dipropylene glycol propyl ether and dipropylene etc., the low boiling point solvent are also those skilled in the art institute
It is well known, such as can be propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, acetic acid
Ethyl ester, propyl acetate, cyclohexanone and ethylene glycol ethyl ether etc..The coloring other than above-mentioned enumerate also can be used in those skilled in the art
Agent, alkali soluble resins, multi-functional monomeric compound, Photoepolymerizationinitiater initiater and solvent, the disclosure repeat no more.
According to the disclosure, other auxiliary agents can also be added as needed in the composition, such as may include levelling agent, silicon
At least one of alkane coupling agent and ionic surfactant, above-mentioned auxiliary agent are well known to the skilled person, this public affairs
It opens and repeats no more.The composition of the disclosure will can obtain after the above components are mixed, and mixed mode can be using conventional side
Formula.
The disclosure also provides application of the composition provided by the disclosure in colored filter preparation.The application can wrap
Include the composition is coated on substrate, preliminary drying, exposure, development and it is rear dry and etc. rear obtain there is specific shape
The colored filter of pattern and pixel.
The disclosure is further illustrated below by embodiment, but does not therefore limit the disclosure.
Embodiment and comparative example medium viscosity is measured using BROOKFIELD viscosimeter (DV-2 type), and film thickness uses
BRUKER step instrument (Dektak-XT type) is measured.
The structural formula of nonionic surfactant E1-E4 used in embodiment of the present disclosure 1-4 are as follows:
Embodiment 1-4 and comparative example 1-3
Specifically comprise the following steps: in the embodiment of the present disclosure and comparative example
1) by according to the formula in table 1 uniformly mixing each component in blender, photosensitive polymer combination is formed；Wherein,
Embodiment 1-4 uses nonionic surfactant E1-E4, and comparative example 1-3 is using small molecule acid, other types of non-ionic surface
Activating agent does not add surfactant.
2) photosensitive polymer combination is coated on glass substrate surface, to form film coating.
3) the coated substrate is sent into dryer prebake conditions to remove solvent, 115 DEG C of prebake conditions temperature, the time
It is 2 minutes.
4) mask film covering on dry film coating uses ultraviolet light to be irradiated so that photopolymerization reaction occurs, and irradiation is strong
Degree for it is 60,000,000 burnt/centimetre2。
5) visualization way of spray developing liquid is selected at a temperature of 23 ± 2 DEG C, developer solution is that the KOH of 0.05 weight % is water-soluble
Liquid sprays 50 seconds, washes away unexposed soluble resin composition using developer solution, required image can be obtained.
6) baking is handled after being heated with heating devices such as hot plate or baking ovens, and temperature is 230 DEG C, and the time is 30 minutes.
7) Photosensitve resin composition is measured into viscosity and developing rate, film thickness is measured to colored filter, and to the two into
Row performance evaluation, specific evaluation method are as follows:
A, the storage stability of photosensitive polymer combination is evaluated
Storage stability includes dispersion stabilization and viscosity stability.
Dispersion stabilization: photosensitive polymer combination being stored under 40 DEG C of room temperature after a week, and whether there is or not sedimentations for observation, is commented
Price card is quasi- as follows:
Zero: without sedimentation；
×: there is sedimentation.
Viscosity stability: photosensitive polymer combination is stored under 40 DEG C of room temperature and measures viscosity change after a week, is commented
Price card is quasi- as follows:
Zero: no viscosity change or viscosity change are lower than 0.1 mpas；
△: viscosity is got higher, but is the non-significant change in 0.1-0.5 mpas；
×: higher than the sharply viscosity change of 0.5 mpas.
B, development correlated performance evaluation
It is formed by image to the visualization way of step 5) further to be evaluated, evaluation method includes:
The sideline b1 uniformity
Using optical microscopy, field emission microscopy observation in the uniformity of image lines on glass substrate:
Zero: image lines are neat；
△: image lines are irregular, there is flash.
B2 is resulting visualization
The integrality formed using optical microscopy, field emission microscopy observation in image on glass substrate:
Zero: development is clean；
△: there is a small amount of residual film at graphic edge；
×: do not develop clean, there are a large amount of residual films；
Specific evaluation result is shown in Table 2.
As shown in Table 2, the photosensitive polymer combination of embodiment 1-4 is because of the nonionic surfactant containing the disclosure,
Developing rate is very fast, and Photosensitve resin composition dispersion stabilization and viscosity stability are preferable, and figure development is clean after development,
Sideline is neat, therefore can form the excellent colour filter of imaging effect.It is also learnt by the above results, and not all non-ionic surface
Activating agent is suitable for being added in Photosensitve resin composition.
Table 1
Concrete component in table 1 is as follows:
A: viridine green G58 (manufacture of DIC chemical industry Co., Ltd.)；
B: methacrylic acid and benzylmethacrylate copolymers；；
C1: dipentaerythritol hexaacrylate (Sartomer's manufacture, analyze pure)；
C2: modified by polyacid pentaerythritol triacrylate (Toagosei Co., Ltd's manufacture, analyze pure)；
D:OXE-02 (BASF AG's manufacture)；
E1-E4: nonionic surfactant (manufacture of Kao company)；
E5: nonionic surfactant octyl phenol polyoxyethylene ether (DOW Chemical manufacture)；
H:3- bromo-propionic acid (manufacture of acros company)；
F1:AFKA-3600 (levelling agent, BASF AG's manufacture)；
F2:KH570 (silane coupling agent, γ-methacryloxypropyl trimethoxy silane, lark prestige are analyzed pure)；
S1:PGMEA (propylene glycol methyl ether acetate, lark prestige are analyzed pure)；
S2:EEP (3- ethoxyl ethyl propionate, Chinese medicines group are analyzed pure).Table 2
Claims (10)
1. a kind of Photosensitve resin composition, the composition include:
Colorant；
Alkali soluble resins；
Multi-functional monomeric compound；
Photoepolymerizationinitiater initiater；
Nonionic surfactant；And
Solvent；
Wherein, shown in the structure of the nonionic surfactant such as formula (1):
In formula (1), R1The alkylidene for being 1-5 for carbon number, Ar are the substituted aryl that carbon number is 10-50, and n is the integer of 4-20.
2. composition according to claim 1, wherein R1It is sub- for ethylidene, propylidene, butylidene, pentylidene, 2- methyl
Propyl or 2- methylbutylene, n are the integer of 4-16.
3. composition according to claim 1, wherein shown in the structure of Ar such as formula (2):
In formula (2), wave represents the bonding position of O atom in Ar and formula (1)；Q1-Q5Be each independently hydrogen atom or
The group shown in formula (3), and Q1-Q5It is not simultaneously hydrogen atom；
In formula (3), triangle represents the bonding position of phenyl ring in the group and formula (2), Q6It is 1-5's for hydrogen atom or carbon number
Alkyl.
4. composition according to claim 1 or 3, wherein Ar contains 3-4 phenyl ring.
5. composition according to claim 1, wherein Ar is selected from one of following substituted aryl:
Wherein, wave represents the bonding position of O atom in Ar and formula (1)；R2-R10It is each independently hydrogen atom or carbon number is
The alkyl of 1-5.
6. composition according to claim 1, wherein relative to the alkali soluble resins of 100 parts by weight, the colorant
Content is 15-300 parts by weight, and the content of the multi-functional monomeric compound is 50-300 parts by weight, and the photopolymerization causes
The content of agent is 0.5-40 parts by weight, and the content of the nonionic surfactant is 0.5-40 parts by weight, and the solvent contains
Amount is 800-3000 parts by weight.
7. composition according to claim 1, wherein the colorant is paratonere R254, naphthol green G58 or pigment blue
B15:6, the alkali soluble resins are the esters of acrylic acid alkali soluble resins containing carboxylic acid group；The multi-functional monomeric compound is
Dipentaerythritol hexaacrylate and/or modified by polyacid pentaerythritol triacrylate, the Photoepolymerizationinitiater initiater be selected from
Oxime ester lightlike initiating agent, acetophenones light trigger, diimidazole photoinitiator, Benzophenone-type light initiator and Anthraquinones light
At least one of initiator.
8. composition according to claim 1, wherein the solvent is selected from acetic acid 3- methoxybutyl, diethylene glycol
Methyl ether acetate, diethylene glycol ether acetate, butyl acetate, 2-Butoxyethyl acetate, dipropylene glycol third
Ether, dipropylene, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, 3- second
At least one of oxygroup ethyl propionate, ethyl acetate, propyl acetate, cyclohexanone and ethylene glycol ethyl ether.
9. composition according to claim 1, wherein the composition further includes levelling agent, silane coupling agent and ion
At least one of type surfactant.
10. application of the composition described in any one of claim 1-9 in colored filter preparation.
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| WO2021200815A1 (en) * | 2020-03-30 | 2021-10-07 | 株式会社Adeka | Radical polymerization initiator, composition, cured product, and cured product manufacturing method |
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