TW202022499A - Photosensitive resin composition, photoresist, color filter and display device - Google Patents

Abstract

This specification provides a photosensitive resin composition comprising a binder resin represented by chemical formula 1, a photoresist, a color filter and a display device.

Description

Photosensitive resin composition, photoresist, color filter and display device

This application claims priority from the filing date of Korean Patent Application No. 10-2018-0146358, which was filed with the Korean Intellectual Property Office on November 23, 2018, and its contents are all included in this specification.

This specification relates to a photosensitive resin composition, photoresist, color filter and display device.

Currently, in order to realize a color filter, a pigment dispersion method in which a pigment is used as a colorant is generally applied. However, in the case of a pigment dispersion, the pigment exists in the state of particles, which not only scatters light, but also increases the surface area of the pigment drastically due to the miniaturization of the pigment, resulting in the deterioration of the dispersion stability caused by this, resulting in uneven pigment particle. Therefore, in order to achieve the recently required high brightness, high contrast, and high resolution, it has recently been studied to use dyes instead of pigments as colorants.

Generally, dyes have the advantage of higher transmittance than pigments. However, it has the disadvantage of insufficient heat resistance compared with pigments. In addition, compared with existing pigments, it has better solubility in organic solvents, and therefore has the disadvantage of insufficient chemical resistance. [Prior Art Literature] [Patent Literature] [Patent Document 1] Japanese Open Document JP 9-87534

[Problems to be solved by the invention]

This specification provides a photosensitive resin composition, photoresist, color filter, and display device. [Means to solve the problem]

An embodiment of this specification provides a photosensitive resin composition, the photosensitive resin composition comprising: dibenzopyran dye; a binder resin comprising the following structure represented by Chemical Formula 1; a multifunctional monomer; Photoinitiator; and solvent.

在所述化學式1中，

是指與其他取代基或鍵結部連接的部分， X'為O或NH， L1及L2彼此相同或不同，分別獨立地為直接鍵、經取代或未經取代的伸烷基、-C(=O)-、或-L'-O(C=O)-， L'為經取代或未經取代的伸烷基， T1至T3彼此相同或不同，分別獨立地為氫、羥基、或者經取代或未經取代的烷基， t2為0至4的整數，在t2為2以上的情況下，T2彼此相同或不同， t3為0至5的整數，在t3為2以上的情況下，T3彼此相同或不同。[Chemical Formula 1]

In the chemical formula 1,

It refers to the part connected to other substituents or bonding parts, X'is O or NH, L1 and L2 are the same or different from each other, and 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 are the same or different from each other, and are independently hydrogen, hydroxyl, or A substituted or unsubstituted alkyl group, t2 is an integer from 0 to 4, when t2 is 2 or more, T2 is the same or different from each other, t3 is an integer from 0 to 5, and when t3 is 2 or more, T3 Same or different from each other.

One embodiment of this specification provides a photoresist manufactured using the photosensitive resin composition.

An embodiment of this specification provides a color filter including the photoresist.

An embodiment of this specification provides a display device including the color filter. [Effect of invention]

Since the photosensitive resin composition according to an embodiment of the present specification includes a binder resin containing a structure represented by Chemical Formula 2, it has the advantage of excellent chemical resistance to migration and elution.

Hereinafter, this specification will be described in more detail.

In this specification, when a component is described as being "on" another component, the case includes not only the case where a certain component is connected to another component, but also the case where another component exists between the two components.

In this specification, when a certain part "includes" a certain component, as long as there is no description to the contrary in particular, this means that other components are not excluded, and other components may be included.

是指與其他取代基或鍵結部鍵結的部位。In this manual,

It refers to the site of bonding with other substituents or bonding parts.

In this specification, "derivatized unit" refers to a unit molecule or a repeating structure forming a polymer.

An embodiment of this specification provides a photosensitive resin composition, the photosensitive resin composition comprising: dibenzopyran dye; a binder resin comprising the following structure represented by Chemical Formula 1; a multifunctional monomer; Photoinitiator; and solvent.

在所述化學式1中，

是指與其他取代基或鍵結部連接的部分， X'為O或NH， L1及L2彼此相同或不同，分別獨立地為直接鍵、經取代或未經取代的伸烷基、-C(=O)-、或-L'-O(C=O)-， L'為經取代或未經取代的伸烷基， T1至T3彼此相同或不同，分別獨立地為氫、羥基、或者經取代或未經取代的烷基， t2為0至4的整數，在t2為2以上的情況下，T2彼此相同或不同， t3為0至5的整數，在t3為2以上的情況下，T3彼此相同或不同。[Chemical Formula 1]

In the chemical formula 1,

It refers to the part connected to other substituents or bonding parts, X'is O or NH, L1 and L2 are the same or different from each other, and 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 are the same or different from each other, and are independently hydrogen, hydroxyl, or A substituted or unsubstituted alkyl group, t2 is an integer from 0 to 4, when t2 is 2 or more, T2 is the same or different from each other, t3 is an integer from 0 to 5, and when t3 is 2 or more, T3 Same or different from each other.

The photosensitive resin composition of an embodiment of the present specification includes a binder resin having a structure represented by the chemical formula 1, so that the structure represented by the chemical formula 1 promotes a radical reaction during the exposure process. Increasing the degree of polymerization of the binder resin and the polyfunctional monomer in the photosensitive resin composition can increase the degree of curing of the film. As the degree of curing of the film becomes higher, the heat resistance and chemical resistance of the color filter manufactured using the photosensitive resin composition of this specification are improved.

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

In this specification, the term "substituted or unsubstituted" means that it is selected from deuterium, halogen group, nitrile group, nitro group, -OH, carbonyl group, ester group, -COOH, amide group, amide Groups, anionic groups, alkoxy groups, alkyl groups, cycloalkyl groups, alkenyl groups, cycloalkenyl groups, aralkyl groups, phosphine groups, sulfonate groups, amine groups, aryl groups, heteroaryl groups, silyl groups, boron Group, (meth)acryloyl group, (meth)acrylate group, ether group, more than one heterocyclic group containing one or more of N, O, S, or P atoms and an anionic group The substituent is substituted or does not have any substituent.

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

In this specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but the carbon number of the alkyl group may be 1-30. According to another embodiment, the carbon number of the alkyl group is 1-20. According to another embodiment, the carbon number of the alkyl group is 1-10. As specific examples of alkyl groups, there are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl. Etc., but not limited to this.

In this specification, the cycloalkyl group is not particularly limited, but preferably has a carbon number of 3 to 30, and particularly preferably cyclopentyl and cyclohexyl, but it is not limited thereto.

In this specification, an alkylene group refers to a group having two bonding positions in an alkane. The alkylene group may be linear, branched or cyclic. The carbon number of the alkylene is not particularly limited, but the carbon number can be 1-30, for example. In addition, the carbon number may be 1-20, and the carbon number may be 1-10.

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

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

In this specification, the aryl group is not particularly limited, but preferably has a carbon number of 6 to 60, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6-30. According to an embodiment, the carbon number of the aryl group is 6-20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a triphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl, anthracenyl, indenyl, phenanthryl, pyrenyl, perylene, triphenyl, eryl, fluorenyl, etc., but is not limited thereto.

In this specification, the heterocyclic group is a heterocyclic group containing O, N, or S as a heteroatom, and may be aromatic or aliphatic. The carbon number of the heterocyclic group is not particularly limited, but the carbon number is 2-30, specifically, the carbon number is 2-20. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl (Acridyl), pyridazinyl, quinolinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene Group, dibenzothienyl, benzofuranyl, dibenzofuranyl, etc., but not limited to these.

In this specification, the explanation about the heterocyclic group can be applied except that the heteroaryl group is aromatic.

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

In this specification, the anionic group has a chemical bond with the structure of Chemical Formula 1, and the chemical bond may refer to an ionic bond. The anionic group is not particularly limited. For example, it can be applied to U.S. Patent No. 7,939,644, Japanese Patent Application Publication No. 2006-003080, Japanese Patent Application Publication No. 2006-001917, Japanese Patent Application Publication No. 2005-159926, and Japanese Patent Application Publication No. 2006-003080. Japanese Patent Application Publication No. 2007-7028897, Japanese Patent Application Publication No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Application Publication No. 2005-111696, Japanese Patent Application Publication No. 2008-249663, and Japanese Patent Application Publication No. 2014- The anion described in 199436.

As specific examples of the anionic group, there are trifluoromethanesulfonate anion, bis(trifluoromethylsulfonyl)amide anion, bistrifluoromethanesulfonamide anion, and bisperfluoroethylsulfonylimide anion. , tetraphenyl borate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethane sulfonic methide _{^{acyl, SO 3 -, CO 2 -}} , SO 2 N ^- SO ₂ CF ₃ , SO ₂ N ^- SO ₂ CF ₂ CF ₃ , and halogen groups such as fluoro, iodo, and chloro groups, but not limited to these.

In this specification, the anionic group itself may have an anion, or may exist in the form of a complex compound together with other cations. Therefore, depending on the number of substituted anionic groups, the sum of charges of the entire molecule of the compound of the present invention may be different. The compound of the present invention has a cation in one amine group, and therefore, the sum of the charges of the entire molecule can have an anion value obtained by subtracting 1 from the number of substituted anionic groups to 0.

In this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The expression "(meth)acrylic acid" also has the same meaning.

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

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

In the structure, R is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, X3 and X4 are the same or different from each other, and are respectively a direct bond, -Rz-, -Rz-O-, -Rz-S-, or -Rz-NH-, and the Rz is a substituted or a carbon number of 1 to 6 Unsubstituted alkanediyl group (alkanediyl group).

In an embodiment of the present specification, the R may be an alkyl group having 1 to 4 carbon atoms substituted by -OH.

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

For the unsaturated compound having a cyclic ether structure having a carbon number of 2 to 4, the above description can be applied.

In one embodiment of this specification, in addition to the binder resin including the structure represented by the chemical formula 1, the photosensitive resin composition may further include a binder resin commonly used in the corresponding technical field.

在所述化學式2中， R1至R6彼此相同或不同，分別獨立地選自由氫、氘、鹵素基、硝基、經取代或未經取代的烷基、經取代或未經取代的烷氧基、經取代或未經取代的芳基、及經取代或未經取代的雜芳基所組成的群組， R7至R11彼此相同或不同，分別獨立地選自由氫、氘、-OH、-SO₃ ^- 、-SO₃ H、-SO₃ ^- Z⁺ 、-COO^- 、-COOH、-COO^- Z⁺ 、-COORa、-SO₃ Rb、-SO₂ NRcRd、-CONRe、經取代或未經取代的烷基、經取代或未經取代的芳基、及經取代或未經取代的雜芳基所組成的群組， Z⁺ 表示⁺ N(Rf)₄ 、Na⁺ 、或K⁺ ， Ra至Re彼此相同或不同，分別獨立地選自由氫、經取代或未經取代的烷基、經取代或未經取代的芳基、及經取代或未經取代的雜芳基所組成的群組， Rc與Rd能夠彼此鍵結而形成包含氮原子的雜環， Rf能夠相同或不同， 所述R7至R11中的至少一者為-SO₃ ^- 、-SO₃ H、-SO₃ ^- Z⁺ 、-COO^- 、-COO^- Z⁺ 、-COORa、-SO₃ Rb、或-SO₂ NRcRd， R12至R15彼此相同或不同，分別獨立地選自由氫、氘、經取代或未經取代的烷基、經取代或未經取代的芳基、及經取代或未經取代的雜芳基所組成的群組， Q1及Q2彼此相同或不同，分別獨立地為直接鍵、或者經取代或未經取代的伸烷基， Rx為陰離子基團或銨結構， a為0或1。In one embodiment of the present specification, the dibenzopiperan dye is represented by the following chemical formula 2. [Chemical Formula 2]

In the chemical formula 2, R1 to R6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl, and substituted or unsubstituted alkoxy. , Substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups, R7 to R11 are the same or different from each other, and are independently selected from hydrogen, deuterium, -OH, -SO ^{_{3 -, -SO 3 H, -SO}} 3 - Z +, -COO -, -COOH, -COO - Z +, -COORa, -SO 3 Rb, -SO 2 NRcRd, -CONRe, a substituted or unsubstituted The group consisting of the alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group, Z ⁺ represents ⁺ N(Rf) ₄ , Na ⁺ , or K ⁺ , Ra to Res are the same or different from each other, and are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, Rc and Rd can be bonded to each other to form a heterocyclic ring containing a nitrogen atom, an Rf can be the same or different, R7 to R11 in the at least one of ^{_{-SO 3 -, -SO 3 H,}} -SO 3 - Z +, ^{-COO -, -COO - Z +,} -COORa, -SO 3 Rb, or -SO ₂ NRcRd, R12 to R15 are the same or different, each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl group , Substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, Q1 and Q2 are the same or different from each other, and are each independently a direct bond, or substituted or unsubstituted Rx is an anionic group or ammonium structure, and a is 0 or 1.

In one embodiment of this specification, R1 to R6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl having 1 to 30 carbons, and carbon A substituted or unsubstituted alkoxy group having a number of 1 to 30, a substituted or unsubstituted aryl group having a carbon number of 6 to 30, and a substituted or unsubstituted heterocyclic group having a carbon number of 2 to 30 A group of aryl groups. In an embodiment of the present specification, R1 to R6 are the same or different from each other, and are independently selected from hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl with 1 to 20 carbons, carbon A substituted or unsubstituted alkoxy group having a number of 1 to 20, a substituted or unsubstituted aryl group having a carbon number of 6 to 20, and a substituted or unsubstituted heterocyclic group having a carbon number of 2 to 20 A group of aryl groups. In an embodiment of the present specification, R1 to R6 are the same or different from each other, and are independently selected from hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl with 1 to 20 carbons, carbon A substituted or unsubstituted alkoxy group having a number of 1 to 20, a substituted or unsubstituted aryl group having a carbon number of 6 to 20, and a substituted or unsubstituted heterocyclic group having a carbon number of 2 to 20 A group of aryl groups. In one embodiment of this specification, R1 to R6 are hydrogen, or substituted or unsubstituted methyl. In one embodiment of this specification, R1 to R6 are hydrogen or methyl.

In an embodiment of the present specification, R7 to R11 are the same or different and each independently selected from the group consisting of hydrogen, ^{_{deuterium, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -COO -, -COOH, -COO ^- Z ⁺ , -COORa, -SO ₃ Rb, -SO ₂ NRcRd, -CONRe, substituted or unsubstituted alkyl with 1 to 30 carbons, and 6 to 30 carbons A group consisting of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms. In an embodiment of the present specification, R7 to R11 are the same or different and each independently selected from the group consisting of hydrogen, ^{_{deuterium, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -COO -, -COOH, -COO ^- Z ⁺ , -COORa, -SO ₃ Rb, -SO ₂ NRcRd, -CONRe, substituted or unsubstituted alkyl with 1 to 20 carbons, and 6 to 20 carbons A group consisting of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms. In an embodiment of the present specification, R7 to R11 are the same or different, each independently selected from the group consisting of _{^{hydrogen, -SO 3 -, -SO 3 H}} , -SO 3 - Z +, -COO -, -COO - Z + , -COORa, -SO ₃ Rb, and -SO ₂ NRcRd. In an embodiment of the present specification, R7 to R11 are the same or different, each independently selected from the group consisting of hydrogen, -SO ₃ ^- consisting of Z ^+, and the -COORa _{^{-, -SO 3 H, -COO -}} , -COO Group.

In one embodiment of this specification, Z ⁺ is ⁺ N(Rf) ₄ , Na ⁺ , or K ⁺ . In one embodiment of this specification, Z ⁺ is Na ⁺ .

In one embodiment of the present specification, Ra to Re are the same or different from each other, and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 30 carbons, and substituted 6 to 30 carbons. Or an unsubstituted aryl group and a substituted or unsubstituted heteroaryl group with a carbon number of 2 to 30. Rc and Rd can bond with each other to form a heterocyclic ring containing a nitrogen atom, and Rf can Same or different. In an embodiment of the present specification, Ra to Re are the same or different from each other, and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbons, and substituted 6 to 20 carbons. Or an unsubstituted aryl group and a substituted or unsubstituted heteroaryl group with a carbon number of 2 to 20. Rc and Rd can bond with each other to form a heterocyclic ring containing a nitrogen atom, and Rf can Same or different. In one embodiment of the present specification, Ra to Re are the same or different from each other, and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 10 carbons, and substituted 6 to 20 carbons. Or an unsubstituted aryl group and a substituted or unsubstituted heteroaryl group with a carbon number of 2 to 20. Rc and Rd can bond with each other to form a heterocyclic ring containing a nitrogen atom, and Rf can Same or different. In one embodiment of this specification, Ra is a substituted or unsubstituted methyl group. In one embodiment of this specification, Ra is a methyl group. In one embodiment of the present specification, Rc and Rd are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. In an embodiment of the present specification, Rc and Rd are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms. In one embodiment of this specification, Rc and Rd are the same or different from each other, and each independently is hydrogen or a linear or branched alkyl group having 3 to 20 carbon atoms. In one embodiment of this specification, Rc and Rd are the same or different from each other, and are each independently hydrogen or a 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 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. In an embodiment of the present specification, Rc and Rd are the same or different from each other, and are each independently hydrogen or a linear or branched alkyl group having 1 to 10 carbon atoms. In an embodiment of the present specification, Rc and Rd are the same or different from each other, and are each independently hydrogen or a branched alkyl group having 1 to 10 carbon atoms. In one embodiment of this specification, Rc and Rd are the same or different from each other, and are each independently hydrogen, or substituted or unsubstituted 2-ethylhexyl. In one embodiment of this specification, Rc and Rd are the same or different from each other, and each independently is hydrogen or 2-ethylhexyl.

In one embodiment of this specification, -SO ₂ NRcRd can be represented by -SO ₂ NY, and the definitions of Rc and Rd can be applied to the Y.

In one embodiment of the present specification, R12 to R15 are the same or different from each other, and are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, and those having 6 to 30 carbon atoms. A group consisting of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms. In an embodiment of the present specification, R12 to R15 are the same or different from each other, and are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbons, and 6 to 20 carbons. A group consisting of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms. In one embodiment of the present specification, R12 to R15 are the same or different from each other, and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 10 carbons, and alkyl having 6 to 12 carbons. A group of substituted or unsubstituted aryl groups. In an embodiment of the present specification, R12 and R14 are the same or different from each other, and are each independently hydrogen, substituted or unsubstituted ethyl, or substituted or unsubstituted propyl. In one embodiment of this specification, R12 and R14 are the same or different from each other, and are each independently hydrogen, ethyl, n-propyl, or isopropyl. In one embodiment of the present specification, R13 and R15 are the same or different from each other, and are each independently a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group. In one embodiment of this specification, R13 and R15 are the same or different from each other, and are each independently an ethyl group, or are selected from the group consisting of methyl, -SO ₂ NHY, -SO ₃ ^- and -SO ₃ H For the phenyl group substituted by more than one substituent in the group, Y is the same as described above.

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 or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms. In an embodiment of the present specification, Q1 and Q2 are the same or different from each other, and are each independently a direct bond or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. In an embodiment of the present specification, Q1 and Q2 are the same or different from each other, and are each independently a direct bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms. In one embodiment of this specification, Q1 and Q2 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, or a substituted or Unsubstituted propylene. In one embodiment of this 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 this specification, Rx is an anionic group or an ammonium structure. In an embodiment of this specification, Rx is an anionic group, and the anionic group is a chlorine group (Cl ⁻ ).

In one embodiment of this specification, Rx is an ammonium structure, and the ammonium structure can be represented by the following chemical formula A.

在所述化學式A中， A1至A4彼此相同或不同，分別獨立地為氫、或者經取代或未經取代的烷基。 在本說明書的一實施形態中，A1至A4彼此相同或不同，分別獨立地為氫、或碳數為1至30的經取代或未經取代的烷基。 在本說明書的一實施形態中，A1至A4彼此相同或不同，分別獨立地為氫、或碳數為1至20的經取代或未經取代的烷基。 在本說明書的一實施形態中，A1至A4彼此相同或不同，分別獨立地為氫、或碳數為1至12的經取代或未經取代的烷基。[Chemical formula A]

In the chemical formula A, A1 to A4 are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group. In an embodiment of the present specification, A1 to A4 are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. In one embodiment of this specification, A1 to A4 are the same or different from each other, and are each independently hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. In an embodiment of the present specification, A1 to A4 are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.

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

In an embodiment of this specification, the chemical formula 2 may be any of the following structures.

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

表示的含義是指在

的苯基所包含的碳中，在除由甲基取代的部分以外的碳中的任一者可經-SO₂ NHY取代。In the structure, by

The meaning refers to

Among the carbons contained in the phenyl group, any one of the carbons other than the part substituted by the methyl group may be substituted by -SO ₂ NHY.

表示的含義是指在

的苯基所包含的碳中，在除由甲基取代的部分以外的碳中的任一者可經-SO₃ ^- 取代。In the structure, by

The meaning refers to

Among the carbons contained in the phenyl group, any one of the carbons other than the part substituted with a methyl group may be substituted with -SO ₃ ^- .

In one embodiment of this specification, X'is O. In one embodiment of this specification, X'is NH.

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

In one embodiment of this specification, L2 is a direct bond, -C(=O)-, or -L'-O(C=O)-. In one embodiment of this specification, L2 is a direct bond. In one embodiment of this specification, L2 is -C(=O)-. In one embodiment of this 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 this specification, L'is a substituted or unsubstituted methylene group. In one embodiment of this specification, L'is a methylene group.

In one embodiment of this specification, T1 to T3 are the same or different from each other, and are each independently hydrogen, a hydroxyl group, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. In one embodiment of this specification, T1 to T3 are the same or different from each other, and are each independently hydrogen, a hydroxyl group, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. In an embodiment of the present specification, T1 to T3 are the same or different from each other, and are each independently hydrogen, a hydroxyl group, and 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, hydroxyl, and substituted or unsubstituted methyl. In one embodiment of this specification, T1 is hydrogen or methyl. In one embodiment of this specification, T2 is hydrogen. In one embodiment of this specification, T3 is hydrogen, a hydroxyl group, or a methyl group substituted with an amino group.

According to an embodiment of this specification, the chemical formula 1 can be represented by the following chemical formula 3.

在所述化學式3中，

是指與其他取代基或鍵結部連接的部分， X'、L1、L2、T1至T3、t2及t3與在所述化學式1中定義的內容相同。[Chemical formula 3]

In the chemical formula 3,

It refers to a part connected to other substituents or bonding parts, and X', L1, L2, T1 to T3, t2, and t3 are the same as those defined in the chemical formula 1.

In one embodiment of this specification, the chemical formula 1 can be represented by any of the following structures, but it is not limited to this. The chemical formula 1 is a polymerized part formed by any of the following structures.

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

[化學式5]

[化學式6]

[化學式7]

在所述化學式4至化學式7中，

是指與其他取代基或鍵結部連接的部分， L41、L51、L52、及L61彼此相同或不同，分別獨立地為經取代或未經取代的伸烷基， X1、X2、Y1、Y2、Z1及Z2彼此相同或不同，分別獨立地為氫、經取代或未經取代的烷基、經取代或未經取代的環烷基、或者經取代或未經取代的芳基， x2為0至5的整數，在x2為2以上的情況下，X2彼此相同或不同。[Chemical formula 4]

[Chemical formula 5]

[Chemical formula 6]

[Chemical formula 7]

In the chemical formula 4 to chemical formula 7,

It refers to the part connected to other substituents or bonding parts, L41, L51, L52, and L61 are the same or different from each other, and are each independently a substituted or unsubstituted alkylene group, X1, X2, Y1, Y2, Z1 and Z2 are the same or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl, x2 is 0 to An integer of 5, and when x2 is 2 or more, X2 is the same or different from each other.

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

In one embodiment of this specification, X1, X2, Y1, Y2, Z1, and Z2 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a carbon number It is a substituted or unsubstituted cycloalkyl group of 3 to 30, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms. In one embodiment of this specification, X1, X2, Y1, Y2, Z1, and Z2 are the same or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a carbon number It is a substituted or unsubstituted cycloalkyl group having 3 to 20, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In one embodiment of this specification, X1, X2, Y1, Z1, and Z2 are the same or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a carbon number of 3. A substituted or unsubstituted cycloalkyl group having to 10 or a substituted or unsubstituted aryl group having 6 to 12 carbons. In one embodiment of this specification, X1 and Y1 are substituted or unsubstituted methyl groups. In one embodiment of this specification, X1 and Y1 are methyl groups. In one embodiment of this specification, X2 is hydrogen. In one embodiment of this specification, Y2 is a substituted or unsubstituted cyclohexyl group, or a substituted or unsubstituted phenyl group. In one embodiment of this specification, Y2 is cyclohexyl or phenyl. In one embodiment of this specification, Z1 is a substituted or unsubstituted phenyl group. In one embodiment of this specification, Z1 is a phenyl group. In one embodiment of this specification, Z2 is a substituted or unsubstituted methyl group. In one embodiment of this specification, Z2 is a methyl group.

In one embodiment of this specification, the chemical formula 4 can be represented by the following structure, but it is not limited to this.

In one embodiment of this specification, the chemical formula 5 can be represented by the following structure, but it is not limited to this.

In one embodiment of this specification, the chemical formula 6 can be represented by the following structure, but it is not limited to this.

In one embodiment of this specification, the chemical formula 7 can be represented by the following structure, but it is not limited to this.

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

An embodiment of this specification provides a photosensitive resin composition, based on the total weight of the photosensitive resin composition, containing: 0.1% to 30% by weight of the dibenzopiperan dye; 1% by weight To 40% by weight of the binder resin including the structure represented by Chemical Formula 1; 1% to 40% by weight of the polyfunctional monomer; 0.1% to 10% by weight of the photoinitiator; And the balance is solvent.

By making each component of the photosensitive resin composition satisfy the above-mentioned range, a photosensitive resin composition for color filters having excellent heat resistance and chemical resistance can be obtained.

In an embodiment of this specification, the weight average molecular weight of the binder resin is 5,000 g/mol to 30,000 g/mol. Preferably, it may be 5,000 g/mol to 20,000 g/mol.

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

The weight average molecular weight is one of the average molecular weights used based on the molecular weight of a certain polymer substance with uneven molecular weight, and is determined by using the weight fraction to determine the molecular weight of the component molecular species of the polymer compound having a molecular weight distribution. The value obtained by averaging.

The weight average molecular weight can be determined by gel permeation chromatography (Gel Permeation Chromatography, GPC) analysis.

In one embodiment of this specification, the photosensitive resin composition may further include one selected from the group consisting of pigments and dyes.

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

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

The pigment may be a copper phthalocyanine blue pigment or a purple pigment (Pigment violet 23), but is not limited to this. Specifically, the pigment may be C.I pigment blue (pigment blue) 15:6.

The binder resin may use a copolymer resin of a polyfunctional monomer that imparts mechanical strength to the film and a monomer that imparts alkali solubility, and may further include a binder commonly used in the corresponding technical field.

The polyfunctional monomer that provides the mechanical strength of the film may be any one or more of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated imines, and acid anhydrides. As specific examples of the unsaturated carboxylic acid esters, benzyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, Base) dimethylaminoethyl acrylate, isobutyl (meth)acrylate, tertiary butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, (meth)acrylate Base) ethylhexyl 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, octyloxy-2-hydroxypropyl (meth)acrylate, glycerol (meth) Base) acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, methoxytriethyl Glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, P-nonylphenoxy polyethylene glycol (meth)acrylate, p-nonylphenoxy polypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate , 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptafluorodecyl (meth)acrylate, (meth)acrylic acid Tribromophenyl ester, α-hydroxy methyl methacrylate, α-hydroxy ethyl methacrylate, α-hydroxy propyl methacrylate, and α-hydroxy butyl methacrylate, but not only Limited to these. As specific examples of the aromatic vinyl monomers, styrene, α-methylstyrene, (ortho, m, p)-vinyl toluene, (ortho, m, and p)-methoxy But it is not limited to the group consisting of styrene and (ortho, meta, p)-chlorostyrene. As specific examples of the unsaturated ethers, it can be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but it is not limited to these. As specific examples of the unsaturated amides, N-phenylmaleimines, N-(4-chlorophenyl)maleimines, N-(4-hydroxyphenyl) Maleimines and N-cyclohexylmaleimines are in the group, but they are not limited to these. As the acid anhydride, there are maleic anhydride, methylmaleic anhydride, tetrahydrophthalic anhydride, etc., but it is not limited to these.

The monomer imparting alkali solubility is not particularly limited if it contains an acid group. For example, it is preferably selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, Monomethylmaleic acid, 5-norbornene-2-carboxylic acid, phthalic acid mono-2-((meth)acryloxy) ethyl ester, succinic acid mono-2-((methyl) One or more of the group consisting of acryloxy) ethyl and ω-carboxy polycaprolactone mono(meth)acrylate, but it is not limited to these.

In an embodiment of this specification, the multifunctional monomer may be dipentaerythritol pentaacrylate.

According to an embodiment of the present specification, the acid value of the binder resin may be 70 KOH mg/g to 120 KOH mg/g.

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

The photoinitiator is not particularly limited as long as it is an initiator that generates free radicals by light to initiate crosslinking. For example, it may be selected from acetophenone-based compounds, biimidazole-based compounds, and triazine-based compounds. And one or more of the group consisting of oxime-based compounds.

The acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1 -Ketone, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholin-1-propane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butane-1-one, 2-(4-bromo-benzyl-2-dimethylamino- 1-(4-morpholinophenyl)-butane-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, etc., It is not limited to this.

As the biimidazole compound, there are 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl) -4,4',5,5'-Tetra(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl) -4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole It is not limited to this.

The triazine compounds include 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4- Bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid 1,1,1,3,3,3-hexafluoroisopropyl ester, 2-{4-[2,4- Bis(trichloromethyl)-s-triazin-6-yl]phenylthio) ethyl acetate, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl] Phenylthio}2-epoxyethyl acetate, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}cyclohexyl acetate, 2- {4-[2,4-Bis(trichloromethyl)-s-triazin-6-yl]phenylthio}benzyl acetate, 3-{chloro-4-[2,4-bis(trichloromethyl) )-S-triazin-6-yl]phenylthio}propionic 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-dimethylamino) (Phenyl)-1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, etc., and not limited to these .

The oxime compounds include 1,2-octanedione-1-(4-phenylthio)phenyl-2-(phthaloyl oxime) (Ciba-Geigy Company, CGI -124), ethyl ketone-1-(9-ethyl)-6-(2-methylbenzyl-3-yl)-1-(O-acetoxime) (CGI-242), N -1919 (Adeka), etc., are not limited to this.

The photoinitiator may be SPI-03 of Samyang Corporation.

The solvent can be selected from acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, 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, dichloromethane, 1,2 -Dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, hexane, heptane, octane, cyclohexane , Benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tertiary 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 B One or more of the group consisting of acid ester, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but it is not limited thereto.

In an embodiment of this 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 dibenzopyran dye is 0.1% by weight to 30% by weight based on the total weight of the solid content in the photosensitive resin composition, including the formula represented by chemical formula 1. The content of the binder resin of the structure is 1% to 40% by weight, and the content of the photoinitiator is 0.1% to 10% by weight.

On the basis of the total weight of the solid content in the photosensitive resin composition, when each component contained in the photosensitive resin composition satisfies the above range, it has an effect of excellent heat resistance and chemical resistance.

The total weight of the solid content refers to the total weight of the components other than the solvent in the photosensitive resin composition. The solid content and the weight% standard based on the solid content of each component can be measured by a common analysis method used in the art such as liquid chromatography or gas chromatography.

According to an embodiment of the present specification, the photosensitive resin composition further includes an antioxidant, an adhesive agent, a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, and a thermal polymerization inhibitor. One or two or more additives in the group consisting of ultraviolet absorbers, adhesives, dispersants and leveling agents.

In an embodiment of the present specification, the additives can be specifically selected from the group consisting of antioxidants, surfactants, and adjuvants.

In addition, the photosensitive resin composition may further contain a multi-thiol agent.

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

The photo-crosslinking sensitizer can use one or more selected from the group consisting of the following compounds: benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4- Bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl phthalate, 3,3-dimethyl-4-methyl Benzophenone compounds such as oxybenzophenone, 3,3,4,4-tetra(tert-butylperoxycarbonyl)benzophenone; 9-fluorenone, 2-chloro-9-fluorenone , 2-methyl-9-fluorenone and other fluorenone compounds; thioxanthone, 2,4-diethyl thioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyl oxygen Thioxanthone compounds such as thioxanthone, isopropyl thioxanthone, diisopropyl thioxanthone; xanthone compounds such as xanthone, 2-methylxanthone ; Anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tertiary butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenyl acridine , 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane and other acridine compounds; Benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, 9,10-phenanthrenequinone and other dicarbonyl compounds; 2,4,6-trimethyl Phosphine oxide compounds such as benzoyl diphenyl phosphine oxide, bis(2,6-dimethoxybenzyl)-2,4,4-trimethylpentyl phosphine oxide; 4-(bis Benzoic acid such as methylamino) benzoate, ethyl 4-(dimethylamino) benzoate, 2-n-butoxyethyl-4-(dimethylamino) benzoate Ester compounds; 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone, 2,6- Amino synergists such as bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzyl-7-(diethylamino)coumarin, 3-benzyl -7-Methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]- Benzopyrano[6,7,8-ij]-quinazine-11-one and other coumarin compounds; 4-diethylaminochalcone, 4-azidobenzylidene acetophenone Other chalcone compounds; 2-benzyl methylene, 3-methyl-b-naphththiazoline.

The curing accelerator is used to improve curing and mechanical strength. Specifically, it can be selected from 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto- 1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetra(3-mercaptopropionate), pentaerythritol-tris(3-mercaptopropionate), pentaerythritol -Tetra(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate) and trimethylolpropane-tris(3-mercapto) One or more of the group consisting of propionate).

The bonding agent can be commonly used in the art. In one embodiment, the bonding agent may be KBM-503.

The polythiol agent can be commonly used in the art. In one embodiment, the polythiol agent can be PE-01.

As the adhesion promoter, a group selected from the group consisting of methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxy One or more of methacryloyl silane coupling agents such as methacryloyl silane, methacryloyloxypropyl dimethoxy silane, etc. As the alkyl trimethoxy silane, a group selected from octyl trimethoxy silane, ten One or more of dialkyltrimethoxysilane, octadecyltrimethoxysilane, etc.

The surfactant is a silicon-based surfactant or a fluorine-based surfactant. Specifically, the silicon-based surfactant can be BYK-077 and BYK-Chemie (BYK-Chemie). 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 BYK -355, BYK -356, BYK -358, BYK -361, BYK -370, BYK -371, BYK (BYK) BYK-375, BYK-380, BYK-390, etc. As a fluorine-based surfactant, you can use DIC (DaiNippon Ink & Chemicals) )) The company's F-114, 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, TF-1126, TF-1130, TF- 1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc., but not limited to these.

In one embodiment of this specification, the surfactant may be a fluorine-based surfactant, and specifically, may be F-554 of DIC Corporation.

The antioxidant may be one or more selected from the group consisting of hindered phenol-based antioxidants, amine-based antioxidants, sulfur-based antioxidants, and phosphine-based antioxidants, but it is not limited to these . Specific examples of the antioxidant include: phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, or triethyl phosphate; such as 2,6-di-tert-butyl-p-cresol, octadecane 3-(4-hydroxy-3,5-di-tert-butylphenyl) propionate, tetrabis[methylene-3-(3,5-di-tert-butyl-4-hydroxy (Phenyl) propionate) methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,5- Di-tert-butyl-4-hydroxybenzyl diethyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g,t-butyl Phenol 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or bis[ 3,3-bis-(4'-hydroxy-3'-tert-butylphenyl) butyric acid] glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol ester and other Hindered phenols are primary antioxidants; such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-bis-β-naphthyl-p-phenylenediamine and other amine-based secondary antioxidants; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, Thio-based secondary antioxidants such as mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane; or such as triphenyl Phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite, bis(2,4-dibutylphenyl) pentaerythritol diphosphite (Bis(2,4-ditbutylphenyl)Pentaerythritol Diphosphite) or (1,1'-biphenyl)-4,4'-diylbisphosphonite tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester ((1 ,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl]ester) and other phosphite-based secondary antioxidants.

In one embodiment of this specification, the antioxidant may be a hindered phenol-based antioxidant, and specifically may be Songnox-1010 from Songyuan Industry.

As the ultraviolet absorber, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc. can be used, but It is not limited to this, and it can be used by any user in the field.

As the thermal polymerization inhibitor, for example, it may be selected from the group consisting of p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, and N-nitroso Phenyl phenyl hydroxylamine ammonium salt, N-nitrosophenyl hydroxylamine aluminum salt, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-sulfur Bis(3-methyl-6-tert-butylphenol), 2,2-methylene bis(4-methyl-6-tert-butylphenol), 2-mercaptoimidazole and phenothiazine One or more of the group consisting of ), but not limited to these, and may include those generally known in the technical field.

The dispersant can be used by a method of internally adding to the pigment in a form in which the pigment is surface-treated in advance, or a method of externally adding to the pigment. As the dispersant, compound-type, nonionic, anionic, or cationic dispersants can be used, and examples include fluorine-based, ester-based, cationic, anionic, nonionic, and amphoteric surfactants. These can be used individually or in combination of two or more types. Specifically, the dispersant may be selected from polyalkylene glycols and their esters, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonates, sulfonic acids One or more of the group consisting of salt, carboxylate, carboxylate, alkyl amine alkylene oxide adduct, and alkyl amine, but it is not limited to this.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymer leveling agents include polyethyleneimine, polyamide amines, reaction products of amines and epoxides, and specific examples of non-polymer leveling agents include non-polymer sulfur-containing Compounds and non-polymer nitrogen-containing compounds, but not limited to these, can be used by users generally in the field.

One embodiment of this specification provides a photoresist manufactured using the photosensitive resin composition.

In more detail, it provides a photoresist which can form a film or pattern form by applying the photosensitive resin composition of this specification to a base material and hardening by a suitable method.

Although the coating method is not particularly limited, a spray method, a roll coating method, a spin coating method, etc. can be used, and the spin coating method is generally widely used. In addition, after the coating film is formed, as appropriate, a part of the residual solvent may be removed under reduced pressure.

As a light source for curing the photosensitive resin composition of this specification, there are, for example, mercury vapor arc (arc), carbon arc, and xenon (Xe) arc that emit light with a wavelength of 250 nm to 450 nm, but it is not necessarily limited. Here.

The photosensitive resin composition of this specification can be used for pigment dispersion type photoresist, thin film transistor liquid crystal display (TFT LCD) or thin film transistor liquid crystal display (TFT LCD) color filter manufacturing Photoresist for black matrix formation of organic light-emitting diodes, photoresist for overcoat formation, photoresist for colomn spacer, photocurable paint, photocurable ink, photocurable adhesive, printing plate , The use of photoresist for printed wiring boards, plasma display panels (Plasma Display Panel, PDP), etc., is not particularly limited.

According to an embodiment of this specification, a color filter including the photoresist is provided.

The color filter can be manufactured using a photosensitive resin composition containing a binder resin containing the structure represented by the chemical formula 1. The photosensitive resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured, thereby forming a color filter.

The substrate can be a glass plate, a silicon wafer, a polyethersulfone (PES), polycarbonate (Polycarbonate, PC) and other plastic substrate plates, etc., and the type 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 outer coating.

In order to increase the contrast between the color pixels of the color filter, a grid-like black pattern called a black matrix can be arranged. As the material of the black matrix, chromium can be used. In this case, the following method can be used: chromium is vapor-deposited on the entire glass substrate, and a pattern is formed by etching. However, considering the high cost of the manufacturing process, the high reflectivity of chromium, and the environmental pollution caused by the waste liquid of chromium, a resin black matrix using a pigment dispersion method capable of fine processing can also be used.

The black matrix can use black pigments or black dyes as color materials. For example, carbon black can be used alone, or carbon black can be mixed with coloring pigments. In this case, since coloring pigments with insufficient light-shielding properties are mixed, it has the following advantages : Even if the amount of color material is relatively increased, the strength of the film or the adhesion to the substrate will not decrease.

An embodiment of this specification provides a display device including the color filter.

The display device may be a plasma display panel (Plasma Display Panel, PDP), a light emitting diode (Light Emitting Diode, LED), an organic light emitting element (Organic Light Emitting Diode, OLED), a liquid crystal display device (Liquid Crystal Display, LCD), Thin Film Transistor-Liquid Crystal Display (LCD-TFT), and Cathode Ray Tube (CRT).

Hereinafter, in order to specifically explain this specification, examples are given for detailed description. However, the embodiments of this specification can be modified into various other forms, and the scope of this specification is not construed as being limited to the embodiments described below. The examples of this specification are provided for more complete description of this specification for those with average knowledge in the field.

>Examples>

向25 g的N-甲基-2-吡咯啶酮（N-methyl-2-pyrrolidone）加入5 g的[A]（12.34 mmol，1 eq）、7.48 g的2,6-二甲基苯胺（2,6-dimethylaniline）（61.692 mmol，5 eq），升溫至150℃並攪拌。在150℃下在4小時的持續時間內進行反應後，使其冷卻至常溫後，慢慢地添加至500 mL的1 M鹽酸（HCl）水溶液中。添加後在1小時的持續時間內攪拌後，對析出物進行減壓過濾。將過濾物加入至甲醇（MeOH）溶劑，在60℃下在1小時的持續時間內回流（reflux）後，進行減壓過濾。在真空烘箱（Vacuum oven）中進行乾燥得到3.07 g的[A-1]（產率43.0%）。 離子化模式：大氣壓化學遊離（Atmospheric Pressure Chemical Ionization，APCI）+：m/z=574[M+H]+，準確質量（Exact Mass）：5741. Synthesis Examples of Dibenzopyran Dyes [Synthesis Example 1]

To 25 g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone) was added 5 g of [A] (12.34 mmol, 1 eq), 7.48 g of 2,6-dimethylaniline ( 2,6-dimethylaniline) (61.692 mmol, 5 eq), heated to 150°C and stirred. After the reaction was carried out at 150°C for a duration of 4 hours, it was allowed to cool to normal temperature and then slowly added to 500 mL of 1 M hydrochloric acid (HCl) aqueous solution. After the addition was stirred for a duration of 1 hour, the precipitate was filtered under reduced pressure. The filtrate was added to a methanol (MeOH) solvent, refluxed (reflux) for a duration of 1 hour at 60°C, and filtered under reduced pressure. It was dried in a vacuum oven to obtain 3.07 g of [A-1] (yield 43.0%). Ionization mode: Atmospheric Pressure Chemical Ionization (APCI)+: m/z=574[M+H]+, Exact Mass: 574

2. Binder synthesis example

[Synthesis Example 2] Add 51.75 mol% of benzyl methacrylate, 8.63 mol% of N-phenylmaleimide, 10.35 mol% of styrene, and 29.28 mol% of methacrylic acid to the reaction vessel and mix them with a solvent. Mix and warm to 60°C. After that, 10 parts by weight of the thermal polymerization initiator V65 (2,2-azobis(2,4-dimethylvaleronitrile) (2,2-Azobis()) was added based on the total weight of the solid content of the binder resin. 2,4-dimethylvaleronitrile))) and react for 16 hours to produce adhesive resin A. The acid value of the produced adhesive resin A was 125 mg KOH/g, and the weight average molecular weight was 8,200. The produced adhesive resin A has the structural unit shown below.

[Synthesis Example 3] 17.7 mol% of methacrylic acid, 42.9 mol% of glycidyl methacrylate, and 39.4 mol% of styrene were added to a reaction vessel, mixed in a nitrogen atmosphere, and heated to 60°C. The production was carried out in the same manner as in Synthesis Example 2 to produce the binder resin B. The acid value of the produced adhesive resin B was 85 mg KOH/g, and the weight average molecular weight was 10,700. The produced adhesive resin B has the structural unit shown below.

[Synthesis Example 4] 36.49 mol% of styrene, 39.62 mol% of glycidyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of benzophenone methacrylate were charged in the same method as in Synthesis Example 2. Manufacture to manufacture binder resin C. The acid value of the produced adhesive resin C was 88 mg KOH/g, and the weight average molecular weight was 8,300. The produced adhesive resin C has the structural unit shown below.

[Synthesis Example 5] Add 29.87 mol% of styrene, 40.00 mol% of glycidyl methacrylate, 20.02 mol% of methacrylate, and 10.12 mol% of benzophenone methacrylate, and manufacture the adhesive in the same manner as in Synthesis Example 2. Agent resin D. The acid value of the produced adhesive resin D was 88 mg KOH/g, and the weight average molecular weight was 9,200. The manufactured adhesive resin D has the same structural unit as the adhesive resin C.

[Synthesis Example 6] 36.49 mol% of styrene, 36.92 mol% of glycidyl methacrylate, 18.80 mol% of methacrylate, and N-(4-benzylphenyl)methacrylamide (N- (4-benzoylphenyl)methacrylamide) 5.10 mol%, produced in the same manner as in Synthesis Example 2 to produce the adhesive resin E. The acid value of the produced adhesive resin E was 78 mg KOH/g, and the weight average molecular weight was 7,900. The produced adhesive resin E has the structural unit shown below.

[Synthesis Example 7] 36.49 mol% of styrene, 36.92 mol% of cyclohexyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of benzophenone methacrylate were charged in the same method as in Synthesis Example 2. Manufacture to manufacture the adhesive resin F. The acid value of the produced adhesive resin F was 82 mg KOH/g, and the weight average molecular weight was 8,500. The produced adhesive resin F has the structural unit shown below.

[Manufacturing of photosensitive resin composition]

[Comparative Example 1] The composition shown in Table 1 below was mixed to produce a photosensitive resin composition of Comparative Example 1. [Table 1]

[Production of photosensitive resin composition Comparative Example 2 to Comparative Example 4 and Example 1 to Example 4] Except for the types and contents of the applied binder resin and photoinitiator described in Table 2 below, the same The photosensitive resin compositions of Comparative Examples 2 to 4 and Examples 1 to 4 were manufactured with the same components and contents as those described in Table 1. [Table 2]

>Experimental example>

[Substrate production] The photosensitive resin composition manufactured by the above-mentioned Example 1 to Example 4 and Comparative Example 1 to Comparative Example 4 was spincoated on glass (5 cm×5 cm) at 110°C The heat treatment before 70 seconds is performed to form a film. After exposing the film with a photo mask under a high-pressure mercury lamp with an energy of 40 mJ/cm ² , the pattern was developed with an alkaline aqueous solution of potassium hydroxide (KOH) and washed with distilled water. After removing distilled water, post-heat treatment was performed at 230°C for 20 minutes to obtain a color pattern.

[Evaluation of heat resistance] For the post-heat-treated substrates manufactured under the conditions described above, a spectrophotometer (MCPD, Otsuka Co., Ltd) was used to obtain absorption in the wavelength range of 380 nm to 780 nm spectrum. The post-heat-treated substrate was additionally processed at 230°C for 120 minutes, and the transmittance spectrum was obtained under the same equipment and the same measurement range. Using the values L*, a*, and b* obtained from the absorption spectrum obtained by using the C light source as a backlight, ΔEab (heat resistance) was calculated by the following formula 1 and shown in Table 3 below. [Equation 1] ΔEab(L*, a*, b*) = {(ΔL*) ² ＋(Δa*) ² ＋(Δb*) ² } ^1/2 ΔEab value means small color change, which means heat resistance Excellent performance.

[Evaluation of Chemical Resistance] After cutting the substrate subjected to post-heat treatment to 1 cm×5 cm, the wavelength range from 380 nm to 780 nm was measured with a spectrophotometer (MCPD, Otsuka Co., Ltd) Absorption spectrum. After obtaining the spectrum, it was immersed in 16 g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone) solvent, and then left at room temperature for 10 minutes, and then cleaned with distilled water. The transmittance spectrum was obtained under the same equipment and the same measuring range. The above-mentioned [Equation 1] was used for calculation using the spectrum before and after immersion, and ΔEab (chemical resistance) is shown in Table 3 below. A small ΔEab value means a small color change, which means that the chemical resistance is excellent. [table 3]

According to Table 3, it is confirmed that the ΔEab values of Examples 1 to 4 are smaller than those of Comparative Examples 1 to 4, and the photosensitivity that is excellent in heat resistance and chemical resistance by using one embodiment of this specification The resin composition can obtain a color filter.

no

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Claims (9)

A photosensitive resin composition comprising: a dibenzopiperan dye; a binder resin comprising the following structure represented by Chemical Formula 1; a multifunctional monomer; a photoinitiator; and a solvent, [Chemical Formula 1]

In chemical formula 1,

It refers to the part connected to other substituents or bonding parts, X'is O or NH, L1 and L2 are the same or different from each other, and 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 are the same or different from each other, and are independently hydrogen, hydroxyl, or A substituted or unsubstituted alkyl group, t2 is an integer from 0 to 4, when t2 is 2 or more, T2 is the same or different from each other, t3 is an integer from 0 to 5, and when t3 is 2 or more, T3 Same or different from each other. The photosensitive resin composition according to the first item of the patent application, wherein the binder resin containing the structure represented by the chemical formula 1 further contains a cyclic ether structure derived from a carbon number of 2 to 4 Saturated compound unit. The photosensitive resin composition described in item 1 of the scope of patent application, wherein the dibenzopyran dye is represented by the following chemical formula 2: [Chemical formula 2]

In Chemical Formula 2, R1 to R6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, halogen, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, and the group consisting of a substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R7 to R11 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, -OH, -SO ₃ ^{- _{, -SO 3 H, -SO 3 -}} Z +, -COO -, -COOH, -COO - Z +, -COORa, -SO 3 Rb, -SO 2 NRcRd, -CONRe, a substituted or unsubstituted alkyl Group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group, Z ⁺ represents ⁺ N(Rf) ₄ , Na ⁺ , or K ⁺ , Ra to Re each other Same or different, each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, Rc and Rd can be bonded to each other to form a heterocyclic ring containing a nitrogen atom, Rf can be the same or different, R7 to R11, at least one of ^{_{-SO 3 -, -SO 3 H,}} -SO 3 - Z +, -COO -, -COO ^- Z ⁺ , -COORa, -SO ₃ Rb, or -SO ₂ NRcRd, R12 to R15 are the same or different from each other, and are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or A group consisting of an unsubstituted aryl group and a substituted or unsubstituted heteroaryl group, Q1 and Q2 are the same or different from each other, and are each independently a direct bond, or a substituted or unsubstituted alkylene group , Rx is an anionic group or ammonium structure, and a is 0 or 1. The photosensitive resin composition as described in item 1 of the scope of patent application, wherein based on the total weight of the photosensitive resin composition, it comprises: 0.1% to 30% by weight of the dibenzopyran dye; 1% to 40% by weight of the binder resin including the structure represented by Chemical Formula 1; 1% to 40% by weight of the polyfunctional monomer; 0.1% to 10% by weight of the photoinitiator; and The balance is the solvent. The photosensitive resin composition according to claim 1, wherein the weight average molecular weight of the binder resin is 5,000 g/mol to 30,000 g/mol. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition further includes one selected from the group consisting of pigments and dyes. A photoresist manufactured using the photosensitive resin composition described in any one of items 1 to 6 of the scope of patent application. A color filter comprising the photoresist as described in item 7 of the scope of patent application. A display device includes the color filter as described in item 8 of the scope of patent application.