CN112204465A

CN112204465A - Photosensitive resin composition, photosensitive material, color filter and display device

Info

Publication number: CN112204465A
Application number: CN201980036391.3A
Authority: CN
Inventors: 李多美; 金汉修; 金惠陈; 白京林; 梁承秦; 李在容; 金泳雄; 崔相雅
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-11-23
Filing date: 2019-11-22
Publication date: 2021-01-08
Anticipated expiration: 2039-11-22
Also published as: KR102216766B1; WO2020106095A1; CN112204465B; KR20200061035A; TWI725631B; TW202022499A

Abstract

The present specification provides a photosensitive resin composition, a photosensitive material, a color filter and a display device.

Description

Photosensitive resin composition, photosensitive material, color filter and display device

Technical Field

The present application claims priority of korean patent application No. 10-2018-0146358, which was filed on the korean patent office at 23.11.2018, the entire contents of which are incorporated herein by reference.

The present specification relates to a photosensitive resin composition, a photosensitive material, a color filter, and a display device.

Background

At present, in order to realize a color filter, a pigment dispersion method using a pigment as a colorant is generally applied. However, in the pigment dispersion liquid, not only the pigment exists in a particle state to scatter light, but also the pigment surface area is drastically increased due to the fine particle size of the pigment, and uneven pigment particles are generated due to the deterioration of dispersion stability caused thereby. Therefore, in order to achieve high brightness, high contrast, and high resolution, which have been required in recent years, a technique of using a dye instead of a pigment as a colorant has been studied in recent years.

In general, dyes have the advantage of higher transmittance than pigments. However, it has a disadvantage of insufficient heat resistance as compared with pigments. Further, compared with conventional pigments, the pigment has a disadvantage of insufficient chemical resistance because of good solubility in organic solvents.

Disclosure of Invention

Problems to be solved

Means for solving the problems

One embodiment of the present specification provides a photosensitive resin composition including a xanthene dye, a binder resin having a structure represented by the following chemical formula 1, a polyfunctional monomer, a photoinitiator, and a solvent.

[ chemical formula 1]

In the above-described chemical formula 1,

represents a moiety linked to another substituent or a binding moiety,

x' is O or NH,

l1 and L2, which are identical to or different from one another, are each, independently, a direct bond, a substituted or unsubstituted alkylene group, -C (═ O) -, or-L' -O (C ═ O) -,

l' is a substituted or unsubstituted alkylene group,

t1 to T3, which are identical to or different from one another, are each independently hydrogen, hydroxy, or substituted or unsubstituted alkyl,

t2 is an integer of 0 to 4, and when T2 is 2 or more, T2 are the same as or different from each other,

t3 is an integer of 0 to 5, and when T3 is 2 or more, T3 are the same as or different from each other.

One embodiment of the present specification provides a photosensitive material produced using the photosensitive resin composition.

One embodiment of the present specification provides a color filter including the photosensitive material.

One embodiment of the present specification provides a display device including the color filter.

Effects of the invention

Photosensitive resin set according to one embodiment of the present descriptionThe compound has a transfer dye since it includes a binder resin having a structure represented by chemical formula 2

And excellent chemical resistance of elution.

Detailed Description

The present specification will be described in more detail below.

In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.

In the present specification, when a part is referred to as "including" or "containing" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.

In the context of the present specification,

indicates a site to which another substituent or a binding moiety binds.

In the present specification, "derived unit" means a unit molecule or a repeating structure forming a macromolecule.

[ chemical formula 1]

In the above-described chemical formula 1,

represents a moiety linked to another substituent or a binding moiety,

x' is O or NH,

l' is a substituted or unsubstituted alkylene group,

In the photosensitive resin composition according to one embodiment of the present description, since the binder resin having the structure represented by chemical formula 1 is included, the structure represented by chemical formula 1 promotes a Radical (radial) reaction during an exposure process, and thus the degree of polymerization of the binder resin and the polyfunctional monomer in the photosensitive resin composition is increased, thereby increasing the hardness of a film. As the hardness of the film becomes higher, the heat resistance and chemical resistance of the color filter manufactured using the photosensitive resin composition according to the present specification are improved.

Examples of the structure represented by the chemical formula, the substituent of the dye or the compound in the present specification are described below, but the present invention is not limited thereto.

In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; -OH; a carbonyl group; an ester group; -COOH; an imide group; an amide group; an anionic group; an alkoxy group; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; an arylalkyl group; a phosphine group; sulfonate/salt groups; an amine group; an aryl group; a heteroaryl group; a silyl group; a boron group; a (meth) acryloyl group; a (meth) acrylate group; an ether group; containing N, O, S or 1 or more of heterocyclic groups and anionic groups among P atoms, or having no substituent.

In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but the number of carbon atoms of the alkyl group may be 1 to 30. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and particularly preferably a cyclopentyl group or a cyclohexyl group, but is not limited thereto.

In this specification, alkylene refers to a group having two binding sites on an alkane (alkane). The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, and for example, the number of carbon atoms may be 1 to 30. In addition, the number of carbon atoms may be 1 to 20, and the number of carbon atoms may be 1 to 10.

In the present specification, the alkylene group may be an alkanediyl (alkanediyl), and the description of the alkylene group may be applied to the alkanediyl.

In the present specification, the cycloalkyl group is not particularly limited, but according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthryl group, an indenyl group, a phenanthryl group, or a pyrenyl groupPerylene, triphenylene, perylene, and perylene,

And a fluorenyl group, but is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and may be aromatic or aliphatic. The number of carbon atoms of the heterocyclic group is not particularly limited, but is 2 to 30, specifically 2 to 20. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl, pyridazinyl, quinolyl, isoquinolyl, indolyl, carbazolyl, benzoquinoyl

Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuryl, dibenzofuryl and the like, but is not limited thereto.

In the present specification, the heteroaryl group is an aromatic group, and the above description of the heterocyclic group can be applied thereto.

In the present specification, the alkoxy group may be a linear or branched one, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

In the present specification, the anionic group has a chemical bond with the structure of chemical formula 1, and the chemical bond may be an ionic bond. The anionic group is not particularly limited, and for example, anions described in U.S. Pat. No. 7,939,644, Japanese patent application laid-open No. 2006-.

Specific examples of the anionic group include trifluoromethanesulfonate anion; bis (trifluoromethylsulfonyl) amide anion; bis (trifluoromethanesulfonyl) imide anion; bis-perfluoroethylsulfonimide anion; tetraphenyl borate anion; tetrakis (4-fluorophenyl) borate; tetrakis (pentafluorophenyl) borate; tris (trifluoromethanesulfonyl) methide; SO (SO)₃ ^-；CO₂ ^-；SO₂N^-SO₂CF₃；SO₂N^-SO₂CF₂CF₃(ii) a Halogen groups such as fluorine groups, iodine groups, chlorine groups, etc., but are not limited thereto.

In the present specification, the anionic group may have an anion itself, or may be present in the form of a complex together with other cations. Therefore, the sum of the overall charges of the molecules of the compound of the present invention may vary depending on the number of substituted anionic groups. Since the compound of the present invention has a cation in one amino group, the sum of the overall charges of the molecules may have a value of 0 or so, which is a value obtained by subtracting 1 from the number of substituted anionic groups.

In the present specification, "(meth) acrylic acid: (meth) acrylic acid

(meth) acrylic acid) "represents at least one selected from acrylic acid and methacrylic acid. "(meth) acrylic acid: (meth)

The expression (meth) acrylic acid) "also has the same meaning.

In one embodiment of the present specification, the binder resin having a structure represented by chemical formula 1 further includes a unit derived from an unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms.

The unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms may be any of the following structures, but is not limited thereto.

In the above structure, R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms,

x3 and X4 are the same as or different from each other and each represents a direct bond, -Rz-O-, -Rz-S-, or-Rz-NH-, wherein Rz represents a substituted or unsubstituted alkanediyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R may be an alkyl group having 1 to 4 carbon atoms and substituted with — OH.

In one embodiment of the present specification, the photosensitive resin composition may further include a binder resin containing a unit derived from an unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms.

The above description can be applied to the unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms.

In one embodiment of the present specification, the photosensitive resin composition may include a binder resin generally used in the art, in addition to the binder resin having the structure represented by chemical formula 1.

In one embodiment of the present specification, the xanthene dye is represented by the following chemical formula 2.

[ chemical formula 2]

In the above-described chemical formula 2,

r1 to R6, which are identical to or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group,

r7 to R11, equal to or different from each other, are each independently selected from hydrogen, deuterium, -OH, -SO₃ ^-、-SO₃H、-SO₃ ^-Z⁺、-COO^-、-COOH、-COO^-Z⁺、-COORa、-SO₃Rb、-SO₂NRcRd, -CONRe, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl,

Z⁺to represent⁺N(Rf)₄、Na⁺Or K⁺，

Ra to Re, equal to or different from each other, are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl,

rc and Rd may combine with each other to form a heterocyclic ring containing a nitrogen atom,

rf may be the same or different and may,

at least one of the above R7 to R11 is-SO₃ ^-、-SO₃H、-SO₃ ^-Z⁺、-COO^-、-COO^-Z⁺、-COORa、-SO₃Rb, or-SO₂NRcRd，

R12 to R15, which are the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group,

q1 and Q2, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted alkylene group,

rx is an anionic group or an ammonium structure,

a is 0 or 1.

In one embodiment of the present specification, R1 to R6, which are the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R6, which are the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, R1 to R6 are hydrogen, or substituted or unsubstituted methyl.

In one embodiment of the present specification, R1 to R6 are hydrogen, or methyl.

In one embodiment of the present specification, R7 to R11, which are the same or different from each other, are each independently selected from hydrogen, deuterium, -OH, -SO₃ ^-、-SO₃H、-SO₃ ^-Z⁺、-COO^-、-COOH、-COO^-Z⁺、-COORa、-SO₃Rb、-SO₂NRcRd, -CONRe, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R7 to R11, which are the same or different from each other, are each independently selected from hydrogen, deuterium, -OH, -SO₃ ^-、-SO₃H、-SO₃ ^-Z⁺、-COO^-、-COOH、-COO^-Z⁺、-COORa、-SO₃Rb、-SO₂NRcRd, -CONRe, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specificationWherein R7 to R11, which are the same or different from each other, are each independently selected from hydrogen, -SO₃ ^-、-SO₃H、-SO₃ ^-Z⁺、-COO^-、-COO^-Z⁺、-COORa、-SO₃Rb, and-SO₂NRcRd。

In one embodiment of the present specification, R7 to R11, which are the same or different from each other, are each independently selected from hydrogen, -SO₃ ^-、-SO₃H、-COO^-、-COO^-Z⁺and-COORa.

In one embodiment of the present specification, Z⁺Is composed of⁺N(Rf)₄、Na⁺Or K⁺。

In one embodiment of the present specification, Z⁺Is Na⁺。

In one embodiment of the present specification, Ra to Re, which are the same or different from each other, are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, Rc and Rd may be combined with each other to form a heterocyclic ring containing a nitrogen atom, and Rf may be the same or different.

In one embodiment of the present specification, Ra to Re, which are the same or different from each other, are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, Rc and Rd may be combined with each other to form a heterocyclic ring containing a nitrogen atom, and Rf may be the same or different.

In one embodiment of the present specification, Ra to Re, which are the same or different from each other, are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, Rc and Rd may be combined with each other to form a heterocyclic ring containing a nitrogen atom, and Rf may be the same or different.

In one embodiment of the present specification, Ra is a substituted or unsubstituted methyl group.

In one embodiment of the present specification, Ra is methyl.

In one embodiment of the present specification, Rc and Rd, which are the same or different from each other, are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, Rc and Rd, which are the same or different from each other, are each independently hydrogen or a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Rc and Rd, which are the same or different from each other, are each independently hydrogen or a linear or branched alkyl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Rc and Rd are the same or different from each other, and each independently hydrogen or a branched alkyl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Rc and Rd, which are the same or different from each other, are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Rc and Rd are the same or different from each other, and each independently represents hydrogen or a linear or branched alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Rc and Rd are the same or different from each other, and each independently hydrogen or a branched alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Rc and Rd, which are the same or different from each other, are each independently hydrogen, or a substituted or unsubstituted 2-ethylhexyl group.

In one embodiment of the present specification, Rc and Rd, which are the same or different from each other, are each independently hydrogen or 2-ethylhexyl.

In one embodiment of the present specification, -SO₂NRcRd can be prepared from-SO₂NY denotes that the above definitions of Rc and Rd can be applied to Y.

In one embodiment of the present specification, R12 to R15, which are the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R12 to R15, which are the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, R12 to R15, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, R12 and R14, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted propyl group.

In one embodiment of the present specification, R12 and R14, which are the same or different from each other, are each independently hydrogen, ethyl, n-propyl, or isopropyl.

In one embodiment of the present specification, R13 and R15, which are the same or different from each other, are each independently a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R13 and R15, equal to or different from each other, are each independently ethyl; or selected from methyl, -SO₂NHY、-SO₃ ^-and-SO₃In H, one or more substituted phenyl groups and Y have the same meanings as defined above.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each independently represents a direct bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, or a substituted or unsubstituted propylene group.

In one embodiment of the present specification, Q1 and Q2 are the same or different from each other and are each independently a direct bond, a methylene group, an ethylene group, or a propylene group.

In one embodiment of the present specification, Rx is an anionic group or an ammonium structure.

In one embodiment of the present specification, Rx is an anionic group, and the anionic group is a chlorine group (Cl)^-)。

In one embodiment of the present specification, Rx has an ammonium structure, and the ammonium structure may be represented by the following chemical formula a.

[ chemical formula A ]

In the above-mentioned chemical formula a,

a1 to a4, which are the same or different from each other, are each independently hydrogen or substituted or unsubstituted alkyl.

In one embodiment of the present specification, a1 to a4 are the same as or different from each other, and each independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, a1 to a4 are the same as or different from each other, and each independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, a1 to a4 are the same as or different from each other, and each independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.

In one embodiment of the present specification, a is 0 or 1.

In one embodiment of the present specification, a is 0.

In one embodiment of the present specification, a is 1.

In one embodiment of the present specification, the chemical formula 2 may have any one of the following structures.

In the above structure, Y is a branched alkyl group having 3 to 20 carbon atoms. Specifically, the above Y is a 2-ethylhexyl group.

In the above structure, the

The meaning of the structure is indicated in

Any one of carbon atoms other than the moiety substituted with a methyl group among carbon atoms contained in the phenyl group of (1) may be substituted with-SO₂NHY。

In the above structure, the

The meaning of the structure is indicated in

Any one of carbon atoms other than the moiety substituted with a methyl group among carbon atoms contained in the phenyl group of (1) may be substituted with-SO₃ ^-。

In one embodiment of the present specification, X' is O.

In one embodiment of the present specification, X' is NH.

In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene group, or — C (═ O) -.

In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, or — C (═ O) -.

In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, or — C (═ O) -.

In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or — C (═ O) -.

In one embodiment of the present description, L1 is a direct bond.

In one embodiment of the present specification, L1 is a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, or a substituted or unsubstituted propylene group.

In one embodiment of the present specification, L1 is methylene, ethylene, or propylene.

In one embodiment of the present specification, L1 is — C (═ O) -.

In one embodiment of the present description, L2 is a direct bond, -C (═ O) -, or-L' -O (C ═ O) -.

In one embodiment of the present description, L2 is a direct bond.

In one embodiment of the present specification, L2 is — C (═ O) -.

In one embodiment of the present specification, L2 is-L' -O (C ═ O) -.

In one embodiment of the present specification, L' is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L' is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L' is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L' is a substituted or unsubstituted methylene group.

In one embodiment of the present specification, L' is methylene.

In one embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently represents hydrogen, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently represents hydrogen, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently represents hydrogen, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, T1 to T3 are the same or different from each other, and are each independently hydrogen, hydroxy, substituted or unsubstituted methyl.

In one embodiment of the present specification, T1 is hydrogen or methyl.

In one embodiment of the present specification, T2 is hydrogen.

In one embodiment of the present specification, T3 is hydrogen, hydroxy, or methyl substituted with an amine group.

According to an embodiment of the present disclosure, chemical formula 1 may be represented by chemical formula 3 below.

[ chemical formula 3]

In the above-mentioned chemical formula 3,

represents a moiety linked to another substituent or a binding moiety,

x', L1, L2, T1 to T3, T2 and T3 are the same as defined in the above chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following structures, but is not limited thereto. The above chemical formula 1 forms a part polymerized from any one of the following structures.

In one embodiment of the present specification, the binder resin may further include one or more structures represented by any one of the following chemical formulas 4 to 7.

[ chemical formula 4]

[ chemical formula 5]

[ chemical formula 6]

[ chemical formula 7]

In the above-mentioned chemical formulas 4 to 7,

represents a moiety linked to another substituent or a binding moiety,

l41, L51, L52 and L61, equal to or different from each other, are each independently a substituted or unsubstituted alkylene group,

x1, X2, Y1, Y2, Z1 and Z2, which are the same as or different from each other, are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, X2 is an integer of 0 to 5, and when X2 is 2 or more, X2 are the same as or different from each other.

In one embodiment of the present specification, L41, L51, L52 and L61 are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L41, L51, L52 and L61 are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L41, L51, L52 and L61 are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L41, L51, L52 and L61, which are the same or different from each other, are each independently a substituted or unsubstituted methylene group.

In one embodiment of the present specification, L41, L51, L52 and L61, which are the same or different from each other, are each independently a methylene group.

In one embodiment of the present specification, X1, X2, Y1, Y2, Z1, and Z2, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, X1, X2, Y1, Y2, Z1, and Z2, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, X1, X2, Y1, Y2, Z1, and Z2, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present description, X1 and Y1 are substituted or unsubstituted methyl groups.

In one embodiment of the present description, X1 and Y1 are methyl.

In one embodiment of the present specification, X2 is hydrogen.

In one embodiment of the present specification, Y2 is a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Y2 is cyclohexyl or phenyl.

In one embodiment of the present specification, Z1 is substituted or unsubstituted phenyl.

In one embodiment of the present specification, Z1 is phenyl.

In one embodiment of the present specification, Z2 is a substituted or unsubstituted methyl group.

In one embodiment of the present specification, Z2 is methyl.

In one embodiment of the present specification, the chemical formula 4 may be represented by the following structure, but is not limited thereto.

In one embodiment of the present specification, the chemical formula 5 may be represented by the following structure, but is not limited thereto.

In one embodiment of the present specification, chemical formula 6 may be represented by the following structure, but is not limited thereto.

In one embodiment of the present specification, chemical formula 7 may be represented by the following structure, but is not limited thereto.

In one embodiment of the present specification, the binder resin may be a copolymer including at least one structure selected from the group consisting of the structures represented by the chemical formula 1 and the chemical formulae 4 to 7.

One embodiment of the present disclosure provides a photosensitive resin composition, including, based on the total weight of the photosensitive resin composition: 0.1 to 30% by weight of the above xanthene dye, 1 to 40% by weight of a binder resin containing a structure represented by the above chemical formula 1,1 to 40% by weight of the above polyfunctional monomer, 0.1 to 10% by weight of the above photoinitiator, and the balance of a solvent.

By allowing each component of the photosensitive resin composition to satisfy the above ranges, a photosensitive resin composition for a color filter having excellent heat resistance and chemical resistance can be obtained.

In one embodiment of the present specification, the weight average molecular weight of the binder resin is 5000 to 30000 g/mol. Preferably, it may be from 5000 to 20000 g/mol.

When the binder resin satisfies the above weight average molecular weight range, a color filter film having excellent heat resistance and chemical resistance can be obtained.

The weight average molecular weight is one of average molecular weights used based on the molecular weight of a certain polymer substance and having a molecular weight distribution, and is a value obtained by averaging the molecular weights of component molecular species of a polymer compound having a molecular weight distribution in terms of weight fractions.

The above weight average molecular weight can be determined by Gel Permeation Chromatography (GPC) analysis.

In one embodiment of the present specification, the photosensitive resin composition may further include one selected from a pigment and a dye.

That is, the photosensitive resin composition may further include at least 1 of a dye and a pigment in addition to the compound of chemical formula 1. For example, the photosensitive resin composition may contain only the compound of the chemical formula 1, or contain the compound of the chemical formula 1 and 1 or more kinds of dyes, or contain the compound of the chemical formula 1 and 1 or more kinds of pigments, or may contain the compound of the chemical formula 1,1 or more kinds of dyes, and 1 or more kinds of pigments.

The dye may be anthraquinone, azaporphyrin, azo, triarylmethane, phthalocyanine or dipyrrolopyrrole, but is not limited thereto.

The Pigment may be a ketone phthalocyanine-based blue Pigment or a violet Pigment (Pigment violet 23), but is not limited thereto. Specifically, the c.i pigment blue of the above pigment may be 15: 6.

The binder resin may be a copolymer resin of a polyfunctional monomer for imparting mechanical strength to the film and a monomer for imparting alkali solubility, and may contain a binder generally used in the art.

The polyfunctional monomer for imparting mechanical strength to the film may be any one or more of unsaturated carboxylic acid esters, aromatic vinyl compounds, unsaturated ethers, unsaturated imides, and acid anhydrides.

Specific examples of the unsaturated carboxylic acid ester include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, and mixtures thereof, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiglycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiglycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3, 3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, alpha-hydroxymethylmethacrylate, alpha-hydroxydecylalkyl (meth) acrylate, and mixtures thereof, But are not limited to, ethyl alpha-hydroxymethylmethacrylate, propyl alpha-hydroxymethylmethacrylate, and butyl alpha-hydroxymethylmethacrylate.

Specific examples of the aromatic vinyl monomers include, but are not limited to, styrene, α -methylstyrene, (o, m, p) -vinyltoluenes, (o, m, p) -methoxystyrenes, and (o, m, p) -chlorostyrenes.

Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

Specific examples of the unsaturated imides include, but are not limited to, N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide.

Examples of the acid anhydride include, but are not limited to, maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride.

The monomer for imparting alkali solubility is not particularly limited as long as it contains an acid group, and for example, 1 or more selected from (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2-carboxylic acid, mono-2- ((meth) acryloyloxy) ethyl phthalate, mono-2- ((meth) acryloyloxy) ethyl succinate and ω -carboxy polycaprolactone mono (meth) acrylate are preferably used, but not limited thereto.

In one embodiment of the present specification, the polyfunctional monomer may be dipentaerythritol pentaacrylate.

According to an embodiment of the present disclosure, the acid value of the binder resin may be 70 to 120 KOHmg/g.

The acid value of the binder resin can be measured by titration with a 0.1N potassium hydroxide (KOH) methanol solution.

The photoinitiator is not particularly limited as long as it is an initiator that generates a radical by light to trigger crosslinking, and may be, for example, 1 or more selected from acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds.

The acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) one, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one Ketones, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, and the like, but is not limited thereto.

Examples of the biimidazole compound include, but are not limited to, 2-bis (2-chlorophenyl) -4,4',5,5' -tetraphenylbiimidazole, 2 '-bis (o-chlorophenyl) -4,4',5,5 '-tetrakis (3,4, 5-trimethoxyphenyl) -1,2' -biimidazole, 2 '-bis (2, 3-dichlorophenyl) -4,4',5,5 '-tetraphenylbiimidazole, and 2,2' -bis (o-chlorophenyl) -4,4,5,5 '-tetraphenyl-1, 2' -biimidazole.

The triazine compound includes 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 1,1,1,3,3, 3-hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, ethyl 2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } ethanoic acid ester, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } ethanoic, Benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate, 3- { chloro-4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto.

Examples of the oxime compounds include, but are not limited to, 1- (4-phenylthio) phenyl-1, 2-octanedione-2- (O-benzoyloxime) (CIBA-GEIGY Co., Ltd., CGI 124), 1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -ethanone-1- (O-acetyloxime) (CGI 242), and N-1919(ADECA Co., Ltd.).

The photoinitiator may be SPI-03 from Santana.

The solvent is selected from acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, and 1, 4-bis

Alkane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1, 2-dichloroethane, 1,1, 1-trichloroethane, 1,1, 2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl cellosolve, 1 or more of propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but not limited thereto.

In one embodiment of the present specification, the solvent may be propylene glycol monomethyl ether acetate and/or 3-methoxybutyl acetate.

In one embodiment of the present specification, the content of the xanthene dye is 0.1 to 30% by weight, the content of the binder resin having a structure represented by the following chemical formula 1 is 1 to 40% by weight, and the content of the photoinitiator is 0.1 to 10% by weight, based on the total weight of solid components in the photosensitive resin composition.

When each constituent element contained in the photosensitive resin composition satisfies the above range based on the total weight of the solid content in the photosensitive resin composition, the photosensitive resin composition has an effect of excellent heat resistance and chemical resistance.

The total weight of the solid components is the sum of the total weight of the components other than the solvent in the photosensitive resin composition. The content of the solid content and the weight% of the solid content of each component can be measured by a conventional analytical means used in the art, such as liquid chromatography or gas chromatography.

According to one embodiment of the present disclosure, the photosensitive resin composition further includes 1 or 2 or more additives selected from the group consisting of an antioxidant, an adhesion promoter, a photo-crosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, an adhesion promoter, a dispersant, and a leveling agent.

In one embodiment of the present specification, the additive may be specifically selected from an antioxidant, a surfactant, and a bonding aid.

In addition, the photosensitive resin composition may further include polythiol (multi-thiol).

According to an embodiment of the present disclosure, the content of the additive is 0.1 to 20% by weight based on the total weight of the solid content in the photosensitive resin composition.

As the photo-crosslinking sensitizer, benzophenone-based compounds selected from benzophenone, 4, 4-bis (dimethylamino) benzophenone, 4, 4-bis (diethylamino) benzophenone, 2,4, 6-trimethylaminobenzophenone, methyl o-benzoylbenzoate, 3-dimethyl-4-methoxybenzophenone, 3,4, 4-tetrakis (t-butylperoxycarbonyl) benzophenone, and the like; fluorenone compounds such as 9-fluorenone, 2-chloro-9-fluorenone, and 2-methyl-9-fluorenone; thioxanthone compounds such as thioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; xanthone-based compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone, and 2, 6-dichloro-9, 10-anthraquinone; acridine compounds such as 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 5-bis (9-acridinylpentane), 1, 3-bis (9-acridinyl) propane and the like; dicarbonyl compounds such as benzil, 1,7, 7-trimethyl-bicyclo [2,2,1] heptane-2, 3-dione, and 9, 10-phenanthrenequinone; phosphine oxide compounds such as 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide; benzoate compounds such as methyl 4- (dimethylamino) benzoate, ethyl 4- (dimethylamino) benzoate, and 2-n-butoxyethyl 4- (dimethylamino) benzoate; amino synergists such as 2, 5-bis (4-diethylaminobenzylidene) cyclopentanone, 2, 6-bis (4-diethylaminobenzylidene) cyclohexanone, and 2, 6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone; coumarin-based compounds such as 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, and 10, 10-carbonylbis [1,1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H,11H-C1] -benzopyrano [6,7,8-ij ] -quinolizin-11-one; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene; more than 1 of 3-methyl-b-naphthothiazoline.

The above-mentioned curing accelerator is used for curing and improving mechanical strength, and specifically, it is possible to use a curing accelerator selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and 2-mercaptobenzothiazole

Of oxazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate)More than 1.

The bonding aid may be a material generally used in the art, and in one embodiment, the bonding aid may be KBM-503.

The polythiol agent may be a material generally used in the art, and in one embodiment, the polythiol agent may be PE-01.

The adhesion promoter may be at least 1 member selected from the group consisting of methacryloxy-propyl-trimethoxysilane, methacryloxy-propyl-dimethoxysilane, methacryloxy-propyl-triethoxysilane, methacryloxy-propyl-dimethoxysilane and other methacryloxy-silane coupling agents, and the alkyl-trimethoxysilane may be at least 1 member selected from the group consisting of octyl-trimethoxysilane, dodecyl-trimethoxysilane, octadecyl-trimethoxysilane and the like.

The surfactant is a silicone surfactant or a fluorine surfactant, and specifically, BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. of BYK-Chemicals, Inc. BYK-114, BYK-390, etc. of DIC (DaiNippon & Ink) can be used as the fluorine surfactant F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-554, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, 1126, TF-1130, TF-1116-SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like, but is not limited thereto.

In one embodiment of the present specification, the surfactant may be a fluorine-based surfactant, specifically, F-554 by DIC corporation.

The antioxidant may be at least 1 selected from Hindered phenol (Hindered phenol) antioxidants, amine antioxidants, sulfur antioxidants, and phosphine antioxidants, but is not limited thereto. Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; 2, 6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3, 5-di-t-butylphenyl) propionate, tetrakis [ methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] methane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-t-butyl-4-hydroxybenzyl) benzene, diethyl 3, 5-di-t-butyl-4-hydroxybenzylphosphite, 2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4 '-butylidene-bis (3-methyl-6-t-butylphenol), 4' -thiobis (3-methyl-6-t-butylphenol) or bis [3 ", hindered phenol (Hindered phenol) primary antioxidants such as 3-Bis- (4'-hydroxy-3' -t-butylphenyl) butanoic acid ethylene glycol ester (Bis [3,3-Bis- (4'-hydroxy-3' -tert-butyl-phenyl) butanoic acid ] glycol ester); amine-based auxiliary antioxidants such as phenyl- α -naphthylamine, phenyl- β -naphthylamine, N '-diphenyl-p-phenylenediamine or N, N' -di- β -naphthyl-p-phenylenediamine; a sulfur-based auxiliary antioxidant such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethylthiuram disulfide tetrakis [ methylene-3- (laurylthio) propionate ] methane; or phosphite-based auxiliary antioxidants such as triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, Bis (2, 4-dibutylphenyl) Pentaerythritol diphosphite (Bis (2, 4-dittouylphenyl) Pentaerythritol diphosphite) or tetrakis [2,4-Bis (1, 1-dimethylethyl) phenyl ] 1,1' -diphosphonate ((1,1' -Biphenyl) -4,4' -diamylbisphenous acid tetrakis [2,4-Bis (1, 1-dimethyethyl) phenyl ] ester).

In one embodiment of the present specification, the antioxidant may be a hindered phenol antioxidant, specifically, Songnox-1010, which is available from Songron industry.

Examples of the ultraviolet absorber include, but are not limited to, 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone, and any ultraviolet absorber commonly used in the art may be used.

The thermal polymerization inhibitor may include, for example, 1 or more selected from the group consisting of p-anisole, hydroquinone, catechol (pyrocathol), t-butylcatechol (t-butyl cathol), N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4-thiobis (3-methyl-6-t-butylphenol), 2-methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine (phenothiazine), but is not limited thereto, and may include a thermal polymerization inhibitor generally known in the art.

The dispersant may be used by a method of internally adding the dispersant to the pigment in a form in which the pigment is surface-treated in advance, or a method of externally adding the dispersant to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant can be used, and examples thereof include fluorine type, ester type, cationic type, anionic type, nonionic type, amphoteric surfactant and the like. These may be used individually or in combination of 2 or more.

Specifically, the dispersant includes at least 1 kind selected from the group consisting of polyalkylene glycol and esters thereof, polyoxyalkylene polyol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonate, carboxylate, alkylamide alkylene oxide adduct, and alkylamine, but is not limited thereto.

The leveling agent may be polymerizable or non-polymerizable. Specific examples of the polymerizable leveling agent include polyethyleneimine, polyamidoamine, and a reaction product of an amine and an epoxide, and specific examples of the non-polymerizable leveling agent include a non-polymeric sulfur-containing compound and a non-polymeric nitrogen-containing compound, but are not limited thereto, and any leveling agent commonly used in the art can be used.

More specifically, the photosensitive resin composition of the present specification is applied to a substrate by an appropriate method and cured to form a photosensitive material in the form of a film or a pattern.

The coating method is not particularly limited, and a spray coating method, a roll coating method, a spin coating method, and the like can be used, and a spin coating method is generally widely used. Further, after the coating film is formed, the residual solvent may be partially removed under reduced pressure according to circumstances.

As a light source for curing the colorant composition according to the present specification, for example, a mercury vapor arc (arc), a carbon arc, a Xe arc, or the like that emits light having a wavelength of 250nm to 450nm is exemplified, but not limited thereto.

The photosensitive resin composition according to the present specification can be used for a pigment dispersion type photosensitive material for manufacturing a color filter of a thin film transistor liquid crystal display device (TFT LCD), a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, a photosensitive material for forming an overcoat layer, a photosensitive material for a column spacer, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printed wiring board, a photosensitive material for a Plasma Display Panel (PDP), and the like, but the use thereof is not particularly limited.

According to one embodiment of the present specification, a color filter including the photosensitive material is provided.

The color filter can be manufactured using a photosensitive resin composition containing a binder resin having a structure represented by the chemical formula 1. The color filter can be formed by applying the photosensitive resin composition on a substrate to form a coating film, and exposing, developing and curing the coating film.

The substrate may be a glass plate, a silicon wafer, a plastic-based plate such as Polyethersulfone (PES) or Polycarbonate (PC), and the like, and the type thereof is not particularly limited.

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

According to another embodiment, the color filter may further include an overcoat layer.

For the purpose of improving contrast, a lattice-like black pattern called a black matrix may be arranged between the color pixels of the color filter. As a material of the black matrix, chromium may be used. In this case, a method of forming a pattern by depositing chromium on the entire glass substrate and performing etching treatment may be used. However, a resin black matrix obtained by a microfabricatable pigment dispersion method may be used in consideration of high process costs, high reflectance of chromium, and environmental pollution caused by chromium waste liquid.

The black matrix may use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or carbon black and a coloring pigment may be used in combination, and in this case, since a coloring pigment which is poor in light-shielding property is mixed, there is an advantage that the strength of the film and the adhesion to the substrate are not lowered even when the amount of the coloring material is relatively increased.

The Display device may be any one of a Plasma Display Panel (PDP), a Light Emitting Diode (LED), an Organic Light Emitting Diode (OLED), a Liquid Crystal Display (LCD), a Thin FIlm Transistor-Liquid Crystal Display (LCD-TFT), and a Cathode Ray Tube (CRT).

Modes for carrying out the invention

Hereinafter, the present specification will be described in detail with reference to examples. However, the embodiments according to the present description may be modified into various forms, and the scope of the present description is not to be construed as being limited to the embodiments described below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

< example >

1. Synthetic examples of xanthene dyes

[ Synthesis example 1]

To 25g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone) were added 5g (12.34mmol, 1 equiv.) of [ A ] and 7.48g (61.692mmol, 5 equiv.) of 2,6-dimethylaniline (2, 6-dimethyllaniline), and the mixture was stirred while being heated to 150 ℃. After 4 hours of reaction at 150 ℃, cool to ambient temperature and then slowly add 500mL of 1M aqueous HCl. After the addition, the mixture was stirred for 1 hour, and then the precipitate was filtered under reduced pressure. The filtrate was added to MeOH solvent and filtered under reduced pressure after 1 hour at 60 ℃ under reflux (reflux). Drying in a Vacuum oven (Vacuum oven) gave 3.07g (yield 43.0%) of [ A-1 ].

Ionization mode: APCI +: m/z 574[ M + H ] +, Exact Mass (Exact Mass): 574

2. Adhesive Synthesis examples

[ Synthesis example 2]

In a reaction vessel, 51.75 mol% of benzyl methacrylate, 8.63 mol% of N-phenylmaleimide, 10.35 mol% of styrene, 29.28 mol% of methacrylic acid were added, mixed with a solvent, mixed under a nitrogen atmosphere and heated to 60 ℃. Then, 10 parts by weight of thermal polymerization initiator V65(2, 2-azobis (2, 4-dimethylvaleronitrile)) was added based on the total weight of the solid content of the binder resin and reacted for 16 hours, thereby producing binder resin a.

The acid value of the produced binder resin A was 125mgKOH/g, and the weight-average molecular weight was 8200.

The produced binder resin a had a structural unit represented below.

[ Synthesis example 3]

17.7 mol% of methacrylic acid, 42.9 mol% of glycidyl methacrylate, and 39.4 mol% of styrene were charged into a reaction vessel, mixed under a nitrogen atmosphere, and heated to 60 ℃. A binder resin B was produced by the same method as in synthesis example 2.

The acid value of the produced adhesive resin B was 85mgKOH/g, and the weight-average molecular weight was 10700.

The produced binder resin B has a structural unit represented below.

[ Synthesis example 4]

A binder resin C was produced in the same manner as in synthesis example 2, except that 36.49 mol% of styrene, 39.62 mol% of glycidyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of benzophenone methacrylate were added.

The adhesive resin C thus produced had an acid value of 88mgKOH/g and a weight-average molecular weight of 8300.

The produced binder resin C has a structural unit represented below.

[ Synthesis example 5]

A binder resin D was prepared in the same manner as in synthesis example 2, except that 29.87 mol% of styrene, 40.00 mol% of glycidyl methacrylate, 20.02 mol% of methacrylate, and 10.12 mol% of benzophenone methacrylate were added.

The adhesive resin D thus produced had an acid value of 88mgKOH/g and a weight-average molecular weight of 9200.

The binder resin D was produced to have the same structural unit as the binder resin C.

[ Synthesis example 6]

A binder resin E was prepared in the same manner as in Synthesis example 2, except that 36.49 mol% of styrene, 36.92 mol% of glycidyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of N- (4-benzoylphenyl) methacrylamide (N- (4-benzoylphenyl) methacrylamide) were added.

The adhesive resin E thus produced had an acid value of 78mgKOH/g and a weight-average molecular weight of 7900.

The produced binder resin E has a structural unit represented below.

[ Synthesis example 7]

A binder resin F was prepared in the same manner as in synthesis example 2, except that 36.49 mol% of styrene, 36.92 mol% of cyclohexyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of benzophenone methacrylate were added.

The adhesive resin F thus produced had an acid value of 82mgKOH/g and a weight-average molecular weight of 8500.

The produced binder resin F has a structural unit represented below.

[ production of photosensitive resin composition ]

Comparative example 1

The photosensitive resin composition of comparative example 1 was produced by mixing the compositions shown in table 1 below.

[ Table 1]

[ production of photosensitive resin composition comparative examples 2 to 4 and examples 1 to 4]

Photosensitive resin compositions of comparative examples 2 to 4 and examples 1 to 4 were produced with the same components and contents as those described in table 1, except that the kinds and contents of the binder resin and the photoinitiator were applied according to the contents described in table 2 below.

[ Table 2]

< Experimental example >

[ production of substrate ]

The photosensitive resin compositions manufactured according to the above examples 1 to 4 and comparative examples 1 to 4 were spin-coated on glass (5cm × 5cm), and were subjected to a pre-bake treatment at 110 ℃ for 70 seconds to form a film. The above film was exposed to a high-pressure mercury lamp at 40mJ/cm using a photomask²The pattern is then developed with an aqueous alkali KOH solution and washed with distilled water. After removal of the distilled water, a post-baking treatment was performed at 230 ℃ for 20 minutes, thereby obtaining a color pattern.

[ evaluation of Heat resistance ]

The post-bake treated substrate produced under the conditions described above was subjected to an absorption spectrum in a wavelength range of 380 to 780nm by a spectrometer (MCPD, tsukamur corporation).

The post-baked substrate was further treated at 230 ℃ for 120 minutes, thereby obtaining a transmittance spectrum at the same equipment and the same measurement range.

Using the values L, a, and b obtained from the absorption spectrum obtained using the light source C as a backlight, Δ Eab (heat resistance) was calculated by the following calculation formula 1 and is shown in table 3 below.

[ calculation formula 1]

ΔEab(L*，a*，b*)＝{(ΔL*)²+(Δa*)²+(Δb*)²}^1/2

A small Δ Eab value means a small color change, indicating excellent heat resistance.

[ evaluation of chemical resistance ]

After the substrate subjected to the post-baking treatment 1 time was cut into 1cm × 5cm, an absorption spectrum in a wavelength range of 380 to 780nm was measured by a spectrometer (MCPD, tsukamur corporation).

After obtaining the spectrum, the sample was immersed in 16g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone) solvent, and then left at room temperature for 10 minutes, followed by washing with distilled water. The transmittance spectra were obtained in the same apparatus and in the same measurement range.

Calculated from the spectra before and after immersion using the above [ calculation formula 1], Δ Eab (chemical resistance) is shown in table 3 below.

A small value of Δ Eab means a small color change, indicating excellent chemical resistance.

[ Table 3]

	Delta Eab (Heat resistance)	Delta Eab (chemical resistance)
			Comparative example 1	3.86	4.65
Comparative example 2	3.05	2.05
			Comparative example 3	3.54	3.97
Comparative example 4	2.98	3.87
			Example 1	1.78	0.97
Example 2	1.54	1.18
			Example 3	1.35	0.85
Example 4	1.95	1.58

From table 3 above, it was confirmed that the Δ Eab values of examples 1 to 4 were small as compared with comparative examples 1 to 4, and a color filter could be obtained using the photosensitive resin composition according to an embodiment of the present specification, which is excellent in heat resistance and chemical resistance.

Claims

1. A photosensitive resin composition comprising a xanthene dye, a binder resin having a structure represented by the following chemical formula 1, a polyfunctional monomer, a photoinitiator, and a solvent:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

represents a moiety linked to another substituent or a binding moiety,

x' is O or NH,

l' is a substituted or unsubstituted alkylene group,

2. The photosensitive resin composition according to claim 1, wherein the binder resin having the structure represented by chemical formula 1 further has a unit derived from an unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms.

3. The photosensitive resin composition according to claim 1, wherein the xanthene dye is represented by the following chemical formula 2:

chemical formula 2

In the chemical formula 2,

Z⁺to represent⁺N(Rf)₄、Na⁺Or K⁺，

rf may be the same or different and may,

at least one of the R7-R11 is-SO₃ ^-、-SO₃H、-SO₃ ^-Z⁺、-COO^-、-COO^-Z⁺、-COORa、-SO₃Rb, or-SO₂NRcRd，

rx is an anionic group or an ammonium structure,

a is 0 or 1.

4. The photosensitive resin composition according to claim 1, comprising, based on the total weight of the photosensitive resin composition:

0.1 to 30 weight percent of the xanthene dye;

1 to 40% by weight of a binder resin containing the structure represented by the chemical formula 1;

1 to 40 wt% of the polyfunctional monomer;

0.1 to 10 weight percent of the photoinitiator; and

the balance of solvent.

5. The photosensitive resin composition according to claim 1, wherein the weight average molecular weight of the binder resin is 5000 to 30000 g/mol.

6. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition further comprises one selected from a pigment and a dye.

7. A photosensitive material produced by using the photosensitive resin composition according to any one of claims 1 to 6.

8. A color filter comprising the photosensitive material of claim 7.

9. A display device comprising the color filter of claim 8.