JP6879481B2 - Kinoftalone compounds, photosensitive resin compositions containing them, photosensitive materials, color filters, and display devices. - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0039312 filed with the Korean Intellectual Property Office on April 4, 2018, the entire contents of which are incorporated herein by reference.

The present specification relates to a quinophthalone compound and a photosensitive resin composition containing the same. The present specification also relates to a photosensitive material, a color filter, and a display device including the photosensitive material produced by using the photosensitive resin composition.

Recently, color filters are required to have high brightness and high brightness / dark ratio. Further, one of the main purposes in the development of the display device is to differentiate the performance of the display element by improving the color purity and to improve the productivity in the manufacturing process.

Conventionally, the pigment type used for the color material of the color filter exists in the color photoresist in a particle-dispersed state, so that it is difficult to adjust the brightness and the light-dark ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, they aggregate in the color filter to reduce their solubility and dispersibility, and the large particles that are agglomerated cause multiple scattering of light. Such scattering of polarized light is considered to be the main cause of lowering the light-dark ratio. Efforts are being made to improve the brightness and contrast ratio by ultra-fine pigmenting and stabilizing the dispersion, but the degree of freedom in selecting a color material for realizing color coordinates for a high color purity display device is limited. In addition, the pigment dispersion method using a color material that has already been developed, particularly a pigment, has reached the limit of improving the color purity, brightness, and light-dark ratio of a color filter using the pigment dispersion method.

As a result, there is a need for the development of new color materials capable of increasing color purity to improve color reproduction, brightness and light-dark ratio.

The present inventors intend to provide a quinophthalone-based compound having a novel structure, a photosensitive resin composition containing the same, a photosensitive material produced using the same, a color filter, and a display device containing the same.

前記化学式１において、
Ｒ１およびＲ３のうちの少なくとも１つは、下記化学式２または化学式３で表され、
［化学式２］

［化学式３］

前記化学式２および化学式３において、

は、前記化学式１に連結される部位を示し、
Ｘは、Ｏ；またはＮＨであり、
Ｌは、置換もしくは非置換のアルキレン基；置換もしくは非置換のヘテロアルキレン基；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基であり、
Ｍは、直接結合；置換もしくは非置換のアルキレン基；置換もしくは非置換のヘテロアルキレン基；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基；または置換もしくは非置換の２価の窒素原子を含む二無水物基であり、
Ｒ１およびＲ３のうち前記化学式２または化学式３でないもの、Ｒ４、Ｒ４１およびＲ４２は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；−ＣＯＲ；−ＣＯＯＲ；イミド基；アミド基；陰イオン性基；スルホン酸基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシクロアルケニル基；置換もしくは非置換のスルホネート基；置換もしくは非置換のアミン基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基；および置換もしくは非置換の窒素原子を含む二無水物基からなる群より選択され、隣接する基は、互いに結合して環を形成してもよく、
前記Ｒは、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であり、
ｒ１およびｒ３は、１〜４の整数であり、ｒ１およびｒ２が２以上の場合、括弧（）内の構造は、同一または異なり、
ｒ４は、０〜４の整数であり、ｒ４が２以上の場合、Ｒ４は、同一または異なり、
ｒ２は、０〜２の整数であり、ｒ２が２の場合、Ｒ２は、同一または異なり、
ｒ４１およびｒ４２は、０〜３の整数であり、ｒ４１およびｒ４２が２以上の場合、括弧（）内の構造は、同一または異なる。 One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[Chemical formula 1]

In the chemical formula 1,
At least one of R1 and R3 is represented by the following chemical formula 2 or chemical formula 3.
[Chemical formula 2]

[Chemical formula 3]

In the chemical formulas 2 and 3,

Indicates a site linked to the above chemical formula 1.
X is O; or NH,
L is a substituted or unsubstituted alkylene group; a substituted or unsubstituted heteroalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.
M is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted heteroalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; or a substituted or unsubstituted divalent It is a dianhydride group containing a nitrogen atom and
Of R1 and R3, those which are not the chemical formula 2 or the chemical formula 3, R4, R41 and R42 are the same or different from each other, and independently, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; anionic group; sulfonic acid group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group Substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; and substituted or unsubstituted nitrogen Selected from the group consisting of dianhydride groups containing atoms, adjacent groups may be bonded to each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
r1 and r3 are integers of 1 to 4, and when r1 and r2 are 2 or more, the structures in parentheses () are the same or different.
r4 is an integer from 0 to 4, and when r4 is 2 or more, R4 is the same or different.
r2 is an integer from 0 to 2, and when r2 is 2, R2 is the same or different,
r41 and r42 are integers from 0 to 3, and when r41 and r42 are 2 or more, the structures in parentheses () are the same or different.

One embodiment of the present specification provides a photosensitive resin composition comprising the compound represented by the chemical formula 1, a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

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

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

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

The compound according to one embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, can reduce the dispersion step by having excellent solubility in an organic solvent, and when a conventional pigment is applied. The compound can be used as a colorant in an economical way, as opposed to having to go through a dispersion step.

In addition, the quinophthalone-based compound represented by Chemical Formula 1 according to one embodiment of the present specification can be used as a color material to improve color reproduction, brightness, and light-dark ratio.

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

As used herein, when one member is located "above" another member, this is not only when one member is in contact with another member, but also between the two members. Including the case where the member of is present.

In the present specification, when a component is referred to as "contains" a component, this means that the other component can be further included rather than excluding the other component unless otherwise specified. To do.

According to one embodiment of the present specification, the compound represented by the chemical formula 1 is provided.

One embodiment of the present specification has excellent solubility in an organic solvent by containing the compound represented by the chemical formula 1. Specifically, the solubility is increased when the chemical formula 1 contains a phthalimide linked with an ester group (-COOR).

Bulky substituents prevent intermolecular aggregation, and substituents that allow free rotation of the chromophore further increase the solubility in the solvent. In particular, substituents such as phthalimide are often used as synergists when dispersing pigments.

By increasing the solubility, it is possible to prevent agglomeration between the coloring materials, which can improve economic efficiency by reducing the amount of the material required for dispersing the coloring materials. In addition, the light-dark ratio (CR, Contrast Ratio) can be improved, and excellent heat resistance can be obtained.

Examples of the substituent of the compound represented by the chemical formula 1 will be described below, but the present invention is not limited thereto.

は、他の置換基または結合部に結合する部位を意味する。 In the present specification

Means a site that binds to another substituent or bond.

As used herein, the term "substituted or unsubstituted" refers to a heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; carboxy group; imide group; amide group; anionic group. Alkoxy group; alkyl group; cycloalkyl group; alkenyl group; cycloalkenyl group; sulfonate group; amine group; aryl group; heteroaryl group; silyl group; alkylsulfoxi group; arylsulfoxi group; boron group; acryloyl group; Acrylate group; ether group; substituted with one or more substituents selected from the group containing heterocyclic groups and anionic groups containing one or more of the N, O, S, or P atoms. Or it means that it does not have any substituent.

As used herein, an "adjacent" group is a substituent substituted with an atom in which the substituent is directly linked to an atom substituted, a substituent located sterically closest to the substituent, or the said group. It can mean another substituent in which the substituent is substituted with the substituted atom. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring are interpreted as "adjacent" groups to each other.

As used herein, the said ring means an aromatic or aliphatic ring, as adjacent groups may combine to form a "ring". Specifically, the ring may be an aromatic ring, or may be an aryl group or a heteroaryl group. The description below can be applied to the aryl group and the heteroaryl group. Further, the ring may be an aliphatic ring, and the aliphatic ring means a ring that is not an aromatic ring.

Examples of halogen groups herein include fluorine, chlorine, bromine, or iodine.

As used herein, the carbonyl group may be represented by -COR', where R'is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or It may be an unsubstituted aryl group. The carbon number of the carbonyl group is not particularly limited, but one having 1 to 30 carbon atoms is preferable. Specifically, the compound may have the following structure, but is not limited thereto.

As used herein, the ester group may be represented by −COOR'', where R'' is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or It may be a substituted or unsubstituted aryl group. In the ester group, the oxygen of the ester group may be substituted with a linear, branched or ring alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but those having 1 to 30 carbon atoms are preferable. Specifically, the compound may have the following structure, but is not limited thereto.

As used herein, the amide group may have the nitrogen of the amide group substituted with hydrogen, a linear, branched or ring-chain alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. .. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

In the present specification, the anionic group has a chemical bond with the structure of Chemical Formula 1, and the anionic group is not particularly limited, for example, US Pat. No. 7,939,644, Japan. Japanese Patent Application Laid-Open No. 2006-003080, Japanese Patent Application Laid-Open No. 2006-001917, Japanese Patent Application Laid-Open No. 2005-159926, Japanese Patent Application Laid-Open No. 2007-70288897, Japanese Patent Application Laid-Open No. 2005-071680, Korean Application The anions described in Japanese Patent Application Laid-Open No. 2007-7000393, Japanese Patent Application Laid-Open No. 2005-111696, Japanese Patent Application Laid-Open No. 2008-249663, and Japanese Patent Application Laid-Open No. 2014-199436 are applicable. Specific examples of the anionic group include trifluolmethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluolmethanesulfonimide anion, bisperfluoroethylsulfonimide anion, and tetra. Phenylborate anion, tetrax (4-fluorophenyl) borate, tetrax (pentafluorophenyl) borate, tristrifluoromethanesulfonylmethide, SO ₃ ⁻ , CO ₂ ⁻ , SO ₂ N ⁻ SO ₂ CF ₃ , SO ₂ N ⁻ SO ₂ CF ₂ CF ₃ There are, but are not limited to, halogen groups such as fluorine groups, iodine groups and chlorine groups.

As used herein, anionic groups may have anions themselves or may be present in complex compound form with other cations. Therefore, the total charge of the entire compound molecule of the present invention can be changed according to the number of substituted anionic groups. Since one amine group of the compound of the present invention has a cation, the total charge of the entire molecule is from the anion to 0, which is the number of substituted anionic groups minus one. Can have a value of.

In this specification, the sulfonic acid group is -SO ₃ H.

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

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 1 to 60 are preferable. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. 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 methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group and n-heptyl group. There are, but are not limited to, n-octyl groups. In the present specification, the cycloalkyl group is not particularly limited, but one having 3 to 30 carbon atoms is preferable, and a cyclopentyl group and a cyclohexyl group are particularly preferable, but the cycloalkyl group is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but one having 3 to 60 carbon atoms is preferable, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and the like.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 2 to 60 are preferable. According to one embodiment, the alkyl group has 2 to 30 carbon atoms. According to another embodiment, the alkyl group has 2 to 20 carbon atoms. According to another embodiment, the alkyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group include, but are not limited to, an alkenyl group in which an aryl group such as a stylbenyl group or a styrenyl group is substituted.

In the present specification, the cycloalkenyl group is not particularly limited, but one having 3 to 60 carbon atoms is preferable, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group include, but are not limited to, a cyclopentenylene group and a cyclohexenylene group.

In the present specification, the aryl group is not particularly limited, but one having 6 to 60 carbon atoms is preferable, and a monocyclic aryl group or a polycyclic aryl group may be used. 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 phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a peryleneyl group, a triphenyl group, a chrysenyl group, a fluorenyl group or the like, but is limited thereto. is not it.

In the present specification, the fluorenyl group may be substituted, or the two substituents may be bonded to each other to form a spiro structure.

などのスピロフルオレニル基、

（９，９−ジメチルフルオレニル基）、
および

（９，９−ジフェニルフルオレニル基）などの置換されたフルオレニル基になってもよい。ただし、これに限定されるものではない。 If the fluorenyl group is substituted

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group),
and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited to this.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N, or S as a hetero atom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 30, specifically, the number of carbon atoms. 2 to 20. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxidazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acrizyl group, imidazole group and quinolinyl. Groups, isoquinoline groups, indol groups, carbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, benzofuranyl groups, dibenzofuran groups, etc., but are limited to these. It's not something.

In the present specification, the above-mentioned description of the heterocyclic group is applicable except that the heteroaryl group is aromatic.

In the present specification, the silyl group may be represented by the chemical formula of −SiY1Y2Y3, and Y1, Y2 and Y3 are hydrogen; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group, respectively. May be good. Specifically, the silyl group includes a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like. However, it is not limited to these.

In the present specification, the alkyl sulfoxy group includes, but is not limited to, a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, a butyl sulfoxy group and the like. As the alkyl group in the alkyl sulfoxy group, the above-mentioned description regarding the alkyl group can be applied.

In the present specification, the aryl sulfoxy group includes, but is not limited to, a benzene sulfoxy group, a p-toluene sulfoxy group, and the like. As the aryl group in the aryl sulfoxy group, the above-mentioned description regarding the aryl group can be applied.

In the present specification, the boron group may be represented by the chemical formula of −BY4Y5, and the Y4 and Y5 may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, respectively. .. Specific examples of the boron group include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the acryloyl group means a photopolymerizable unsaturated group, and examples thereof include, but are not limited to, a (meth) acryloyl group.

In the present specification, the acrylate group means a photopolymerizable unsaturated group, and examples thereof include, but are not limited to, a (meth) acrylate group.

As used herein, the term "(meth) acryloyl" refers to at least one selected from the group consisting of acryloyl and meta-acryloyl. The notation of "(meth) acrylate" has the same meaning.

As used herein, the ether group may be represented by −COR''. The R'''is a substituted or unsubstituted alkyl group. As for the alkyl group, the above-mentioned description of the alkyl group can be applied.

As used herein, the sulfonate group may be an alkyl sulfonate group, a cycloalkyl sulfonate group, or an aryl sulfonate group. The above-mentioned description regarding the alkyl group is applicable to the above-mentioned "alkyl", the above-mentioned description regarding the cycloalkyl group is applicable to the above-mentioned "cycloalkyl", and the above-mentioned "aryl" is the above-mentioned description regarding the aryl group. Is applicable.

前記化学式Ｓにおいて、Ａは、置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であってもよい。 In the present specification, the sulfonate group may be represented by the following chemical formula S, but is not limited thereto.
[Chemical formula S]

In the chemical formula S, A may be a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

As used herein, the amine group is from -NH ₂ ; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group, and heteroarylamine group. The group may be selected from the above groups, and the number of carbon atoms is not particularly limited, but those of 1 to 30 are preferable. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthrasenylamine group, a diphenylamine group, and the like. N-phenylnaphthylamine group, ditrilamine group, N-phenyltrilamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N- Phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group However, it is not limited to these.

In the present specification, the number of carbon atoms of the dianhydride group containing a nitrogen atom is not particularly limited, but may be 4 to 30, specifically 4 to 20, and more specifically 4 to 15.

［化学式Ｍ］

前記化学式Ｎおよび化学式Ｍにおいて、Ｂは、−Ｘ−Ｘ'−または−Ｘ＝Ｘ'−であり、ＸおよびＸ'は、ＣＲ_１１Ｒ_１２であり、Ｒ_１１、Ｒ_１２は、互いに同一または異なり、それぞれ独立に、水素；重水素；Ｎ；またはＳであるか、隣接する基は、互いに結合して環を形成し、Ｚ１〜Ｚ３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であるか、隣接する基は、互いに結合して環を形成してもよい。 In the present specification, the dianhydride group containing a nitrogen atom may be represented by the following chemical formula N or chemical formula M, but is not limited thereto.
[Chemical formula N]

[Chemical formula M]

In the chemical formula N and the chemical formula M, B is -X-X'-or -X = X'-, X and X'are CR ₁₁ R ₁₂ , and R ₁₁ and R ₁₂ are the same or the same as each other. Different, each independently is hydrogen; deuterium; N; or S, or adjacent groups are bonded to each other to form a ring, and Z1 to Z3 are the same or different from each other and are independently hydrogen; heavy. Hydrogen; halogen groups; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups, or adjacent groups may be bonded to each other to form a ring.

In the present specification, the above-mentioned description of the dianhydride group containing a nitrogen atom is applicable except that the substituted or unsubstituted divalent nitrogen atom-containing dianhydride group is a divalent group. Is.

As used herein, an alkylene group means an alkane having two bonding positions. The alkylene group may be a straight chain, a branched chain or a ring chain. The carbon number of the alkylene group is not particularly limited, but is, for example, 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

As used herein, a heteroalkylene group means an alkane containing O, N, or S as a hetero atom having two bond positions. The heteroalkylene group may be a straight chain, a branched chain or a ring chain. The number of carbon atoms of the heteroalkylene group is not particularly limited, but is, for example, 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.

As used herein, an arylene group means an aryl group having two bonding positions, that is, a divalent group. The above description of the aryl group is applicable, except that each of these is a divalent group.

As used herein, a heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the above-mentioned description of the heteroaryl group is applicable.

In one embodiment of the specification, X is O; or NH.

In one embodiment of the specification, X is O.

In one embodiment of the specification, X is NH.

Further, in one embodiment of the present specification, L in the chemical formula 1 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; a substituted or unsubstituted heteroalkylene group having 2 to 30 carbon atoms; substituted or unsubstituted. It may be a substituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the specification, the L of the chemical formula 1 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; a substituted or unsubstituted heteroalkylene group having 2 to 20 carbon atoms; a substituted or unsubstituted alkylene group. It may be an arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In one embodiment of the specification, L in Chemical Formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 30 carbon atoms.

In one embodiment of the specification, L in Chemical Formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms.

In one embodiment of the specification, L in Chemical Formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 10 carbon atoms.

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

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

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

In one embodiment of the specification, L in Chemical Formula 1 is a substituted or unsubstituted propylene group.

In one embodiment of the specification, L in Chemical Formula 1 is a propylene group.

Further, in one embodiment of the present specification, the M of the chemical formula 1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted heteroalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted alkylene group. A substituted heteroarylene group; or a dianhydride group containing a substituted or unsubstituted divalent nitrogen atom.

In one embodiment of the specification, M in Chemical Formula 1 is a dianhydride group containing a directly bonded; or substituted or unsubstituted divalent nitrogen atom.

In one embodiment of the specification, M in Chemical Formula 1 is a direct bond.

In one embodiment of the specification, M in Chemical Formula 1 is a dianhydride group containing a substituted or unsubstituted divalent nitrogen atom.

In one embodiment of the specification, M in Chemical Formula 1 is a dianhydride group containing a divalent nitrogen atom.

In one embodiment of the present specification, M of the chemical formula 1 may be represented by the following chemical formula.

In one embodiment of the present specification, M of the chemical formula 1 may be represented by the following chemical formula.

Further, in one embodiment of the present specification, at least one of R1 and R3 of the chemical formula 1 is represented by the chemical formula 2 or the chemical formula 3.

In one embodiment of the present specification, R1 of the chemical formula 1 is represented by the chemical formula 2 or the chemical formula 3.

In one embodiment of the present specification, R1 of the chemical formula 1 is represented by the chemical formula 2.

In one embodiment of the present specification, R1 of the chemical formula 1 is represented by the chemical formula 3.

Further, in one embodiment of the present specification, the R1 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; −COR; −. COOR; imide group; amide group; anionic group; sulfonic acid group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; Substituent or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; and substituted or unsubstituted nitrogen atom Selected from the group consisting of dianhydride groups comprising, adjacent R1s may be bonded to each other to form a ring, wherein the R is hydrogen; heavy hydrogen; substituted or unsubstituted alkyl group; substituted or unsubstituted. Substituted cycloalkyl group; or substituted or unsubstituted aryl group.

In one embodiment of the present specification, R1 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is a hydrogen; halogen group; nitro group; hydroxy group; -COOR; or a substituted or unsubstituted alkyl group. The R1s present or adjacent to each other may be bonded to each other to form a ring, wherein the R is a hydrogen; or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the R1 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is hydrogen; halogen group; nitro group; hydroxy group; -COOR; or substituted or unsubstituted carbon number 1 Alkyl groups of ~ 30 or adjacent R1s may be bonded to each other to form an aromatic ring, said R being a hydrogen; or substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. ..

In one embodiment of the present specification, the R1 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is hydrogen; halogen group; nitro group; hydroxy group; -COOR; or substituted or unsubstituted carbon number 1 Alkyl groups of ~ 20 or adjacent R1s may be bonded to each other to form an aromatic ring, said R being a hydrogen; or substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. ..

In one embodiment of the present specification, the R1 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is hydrogen; halogen group; nitro group; hydroxy group; -COOR; or substituted or unsubstituted carbon number 1 The alkyl groups of 10 to 10 or adjacent R1s may be bonded to each other to form an aromatic ring, wherein the R is a hydrogen; or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. ..

In one embodiment of the present specification, R1 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is hydrogen; F; Cl; Br; nitro group; hydroxy group; -COOR; or substituted or unsubstituted. The tert-butyl group or adjacent R1 may be bonded to each other to form a substituted or unsubstituted benzene ring, wherein the R is a hydrogen; or a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R1 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is a hydrogen; F; Cl; Br; nitro group; hydroxy group; -COOR; or tert-butyl group. The R1s present or adjacent to each other may be bonded to each other to form a benzene ring substituted or unsubstituted with a halogen group; a nitro group; or a sulfonic acid group, and the R1 is a hydrogen; or a methyl group.

In one embodiment of the present specification, R1 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is a hydrogen; F; Cl; Br; nitro group; hydroxy group; -COOR; or tert-butyl group. Or adjacent R1s may be bonded to each other to form a Br; nitro group; or sulfonic acid group substituted or unsubstituted benzene ring, wherein the R is a hydrogen; or a methyl group.

Further, in one embodiment of the present specification, the R2 is hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; anionic group; sulfone. Acid group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted Selected from the group consisting of a sulfonate group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a dianhydride group containing a substituted or unsubstituted nitrogen atom, and adjacent to each other. The R1s may be bonded to each other to form a ring, wherein the R is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group. Is.

In one embodiment of the specification, the R2 is hydrogen; or deuterium.

In one embodiment of the specification, the R2 is hydrogen.

Further, in one embodiment of the present specification, R3 of the chemical formula 1 is represented by the chemical formula 2 or the chemical formula 3.

In one embodiment of the specification, R3 of Chemical Formula 1 is represented by Chemical Formula 2.

In one embodiment of the specification, R3 of Chemical Formula 1 is represented by Chemical Formula 3.

Further, in one embodiment of the present specification, the R3 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; −COR; −. COOR; imide group; amide group; anionic group; sulfonic acid group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; Substituent or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; and substituted or unsubstituted nitrogen atom Selected from the group consisting of dianhydride groups containing, adjacent R1s may combine with each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, the R3 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 contains hydrogen; a substituted or unsubstituted sulfonate group; a substituted or unsubstituted aryl group; a nitrogen atom. Anhydrous groups; or adjacent R3s may combine with each other to form a ring.

In one embodiment of the present specification, the R3 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 contains hydrogen; a substituted or unsubstituted sulfonate group; a substituted or unsubstituted aryl group; a nitrogen atom. Anhydrous groups; or adjacent R3s may combine with each other to form a ring.

In one embodiment of the present specification, the R3 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is hydrogen; an arylsulfonate group having 6 to 30 substituted or unsubstituted carbon atoms; a substituted or unsubstituted carbon. Aryl groups of number 6-30; or dianhydride groups containing a nitrogen atom, or adjacent R3s may combine with each other to form an aromatic ring.

In one embodiment of the present specification, the R3 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is hydrogen; an arylsulfonate group having 6 to 20 substituted or unsubstituted carbon atoms; a substituted or unsubstituted carbon. Aryl groups of number 6-20; or dianhydride groups containing a nitrogen atom, or adjacent R3s may combine with each other to form an aromatic ring.

In one embodiment of the present specification, the R3 of the chemical formula 1 which is not the chemical formula 2 or the chemical formula 3 is hydrogen; an arylsulfonate group having 6 to 10 carbon atoms substituted or unsubstituted; a phenyl group; or a nitrogen atom. R3s containing, or adjacent to each other, may be bonded to each other to form a benzene ring; or a pyridine ring.

In one embodiment of the present specification, the R3 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is hydrogen.

前記化学式Ｓにおいて、Ａは、置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基である。 In one embodiment of the present specification, among R3 of the chemical formula 1, those which are not the chemical formula 2 or the chemical formula 3 are substituted or unsubstituted aryl sulfonate groups, and the substituted or unsubstituted aryl sulfonate groups are as follows. It may be represented by the chemical formula S.
[Chemical formula S]

In the chemical formula S, A is a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the specification, A in Chemical Formula S is a substituted or unsubstituted aryl group.

In one embodiment of the specification, A in Chemical Formula S is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the specification, A in Chemical Formula S is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the specification, A in Chemical Formula S is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

In one embodiment of the specification, A of the chemical formula S is a phenyl group; or a naphthyl group.

In one embodiment of the present specification, the chemical formula S may be represented by any one of the following chemical formulas.

In one embodiment of the present specification, the R3 of the chemical formula 1 that is not the chemical formula 2 or the chemical formula 3 is a phenyl group.

［化学式Ｍ］

前記化学式Ｎおよび化学式Ｍにおいて、Ｂは、−Ｘ−Ｘ'−または−Ｘ＝Ｘ'−であり、ＸおよびＸ'は、ＣＲ_１１Ｒ_１２であり、Ｒ_１１、Ｒ_１２は、互いに同一または異なり、それぞれ独立に、水素；重水素；Ｎ；またはＳであるか、隣接する基は、互いに結合して環を形成し、Ｚ１〜Ｚ３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であるか、隣接する基は、互いに結合して環を形成してもよい。 In one embodiment of the present specification, among R3 of the chemical formula 1, the one not the chemical formula 2 or the chemical formula 3 is a dianhydride group containing a nitrogen atom, and the dianhydride group containing a nitrogen atom is described below. It may be represented by the chemical formula N or the following chemical formula M.
[Chemical formula N]

[Chemical formula M]

In the chemical formula N and the chemical formula M, B is -X-X'-or -X = X'-, X and X'are CR ₁₁ R ₁₂ , and R ₁₁ and R ₁₂ are the same or the same as each other. Different, each independently is hydrogen; deuterium; N; or S, or adjacent groups are bonded to each other to form a ring, and Z1 to Z3 are the same or different from each other and are independently hydrogen; heavy. Hydrogen; halogen groups; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups, or adjacent groups may be bonded to each other to form a ring.

In one embodiment of the present specification, B of the chemical formula N is -X-X'-or -X = X'-, and X and X'are CR ₁₁ R ₁₂ and R ₁₁ , R ₁₂ Are the same or different from each other and are independently hydrogen; deuterium; N; or S, or adjacent groups may combine with each other to form an aliphatic or aromatic ring.

In one embodiment of the present specification, Z1 to Z3 of the chemical formula M are the same or different from each other, and independently, hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or Substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 to Z3 of the chemical formula M are the same or different from each other, and independently, hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or Substituted or unsubstituted aryl groups having 6 to 20 carbon atoms or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 to Z3 of the chemical formula M may independently bond with adjacent groups to form an aromatic ring.

In one embodiment of the present specification, Z1 and Z2 of the above chemical formula M may be bonded to each other to form an aromatic ring, and Z2 and Z3 may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 and Z2 of the above chemical formula M are bonded to each other to form a substituted or unsubstituted benzene ring, and Z2 and Z3 are bonded to each other to form a substituted or unsubstituted benzene ring. It may be formed.

In one embodiment of the present specification, Z1 and Z2 of the above chemical formula M may be bonded to each other to form a benzene ring, and Z2 and Z3 may be bonded to each other to form a benzene ring.

前記化学式において、Ｎ１〜Ｎ１８は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；−ＣＯＲ；−ＣＯＯＲ；イミド基；アミド基；陰イオン性基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシクロアルケニル基；置換もしくは非置換のスルホネート基；置換もしくは非置換のアミン基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基；および置換もしくは非置換の窒素原子を含む二無水物基からなる群より選択され、隣接する基は、互いに結合して環を形成してもよく、
前記Ｒは、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であり、
ｎ１は０〜４の整数、ｎ２は０〜２の整数、ｎ３は０〜４の整数、ｎ８は０〜８の整数、ｎ９は０〜４の整数、ｎ１０は０〜４の整数、ｎ１１は０〜２の整数、ｎ１２は０〜５の整数、ｎ１３は０〜２の整数、ｎ１４は０〜２の整数、ｎ１５は０〜４の整数、ｎ１６は０〜４の整数、ｎ１７は０〜３の整数、ｎ１８は０〜３の整数であり、
ｎ１〜ｎ１８が２以上の場合、括弧（）内の構造は、同一または異なる。 In one embodiment of the present specification, the chemical formula N may be represented by any one of the following chemical formulas.

In the above chemical formula, N1 to N18 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; anionic. Group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate Selected from the group consisting of a group consisting of a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a dianhydride group containing a substituted or unsubstituted nitrogen atom, and adjacent to each other. The groups may combine with each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
n1 is an integer from 0 to 4, n2 is an integer from 0 to 2, n3 is an integer from 0 to 4, n8 is an integer from 0 to 8, n9 is an integer from 0 to 4, n10 is an integer from 0 to 4, and n11 is. 0-2 integer, n12 is 0-5 integer, n13 is 0-2 integer, n14 is 0-2 integer, n15 is 0-4 integer, n16 is 0-4 integer, n17 is 0- An integer of 3 and n18 are integers of 0 to 3.
When n1 to n18 are 2 or more, the structures in parentheses () are the same or different.

In one embodiment of the specification, the N1 to N18 are hydrogen.

前記化学式Ｍ−１において、Ｎ１９およびＮ２０は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；−ＣＯＲ；−ＣＯＯＲ；イミド基；アミド基；陰イオン性基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシクロアルケニル基；置換もしくは非置換のスルホネート基；置換もしくは非置換のアミン基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基；および置換もしくは非置換の窒素原子を含む二無水物基からなる群より選択され、隣接する基は、互いに結合して環を形成してもよく、
前記Ｒは、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であり、
ｎ１９およびｎ２０は、互いに同一または異なり、それぞれ独立に、０〜３の整数であり、ｎ１９およびｎ２０が２以上の場合、括弧（）内の構造は、同一または異なる。 In one embodiment of the present specification, the chemical formula M may be represented by the following chemical formula M-1.
[Chemical formula M-1]

In the chemical formula M-1, N19 and N20 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; Anionic group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted Selected from the group consisting of a substituted sulfonate group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a dianhydride group containing a substituted or unsubstituted nitrogen atom. , Adjacent groups may combine with each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
n19 and n20 are the same or different from each other and are independently integers of 0 to 3, and when n19 and n20 are 2 or more, the structures in parentheses () are the same or different.

In one embodiment of the specification, N19 and N20 of the chemical formula M-1 are hydrogen.

Further, in one embodiment of the present specification, the R4 is hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; anionic group; substitution. Alternatively, an unsubstituted alkoxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted cycloalkenyl group; a substituted or unsubstituted sulfonate group; a substituted Alternatively, the group is selected from the group consisting of an unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a dianhydride group containing a substituted or unsubstituted nitrogen atom, and the adjacent group is selected from the group. They may be combined with each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the specification, the R4 may be hydrogen or adjacent groups may bond to each other to form a ring.

In one embodiment of the specification, the R4 may be hydrogen or adjacent groups may be attached to each other to form an aromatic ring.

In one embodiment of the specification, the R4 may be hydrogen or adjacent groups may be bonded to each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the specification, the R4 may be hydrogen or adjacent groups may bond to each other to form a benzene ring.

Further, in one embodiment of the present specification, the R41 and R42 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide. Group; amide group; anionic group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl From a dianhydride group containing a substituted or unsubstituted sulfonate group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a substituted or unsubstituted nitrogen atom. Adjacent groups selected from the group may combine with each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the specification, the R41 and R42 are hydrogen.

Further, in one embodiment of the present specification, r1 is an integer of 1 to 4.

Further, in one embodiment of the present specification, r2 is an integer of 0 to 2.

Further, in one embodiment of the present specification, r3 is an integer of 1 to 4.

Further, in one embodiment of the present specification, r4 is an integer of 0 to 4.

前記構造において、Ｒ１〜Ｒ３およびｒ１〜ｒ３は、前述したところによる。 In one embodiment of the present specification, the chemical formula 1 may be represented by the following structure, the following structure represents an isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. .. An isomer means a molecule having the same molecular formula but having different physical / chemical properties from each other.

In the structure, R1 to R3 and r1 to r3 are as described above.

The description of the isomer is applicable to all of the chemical formulas described herein.

［化学式５］

前記化学式４および化学式５において、
Ｒ２〜Ｒ４、Ｒ４１、Ｒ４２、Ｌ、Ｍ、ｒ２〜ｒ４、ｒ４１およびｒ４２は、前記化学式１で定義した通りであり、
Ｒ５は、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；−ＣＯＲ；−ＣＯＯＲ；イミド基；アミド基；陰イオン性基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシクロアルケニル基；置換もしくは非置換のスルホネート基；置換もしくは非置換のアミン基；置換もしくは非置換のアリール基；および置換もしくは非置換のヘテロアリール基からなる群より選択され、
前記Ｒは、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であり、
ｒ５は、０〜３の整数であり、ｒ５が２以上の場合、Ｒ５は、互いに同一または異なる。 According to another embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 4 or chemical formula 5.
[Chemical formula 4]

[Chemical formula 5]

In the chemical formulas 4 and 5,
R2 to R4, R41, R42, L, M, r2 to r4, r41 and r42 are as defined in Chemical Formula 1 above.
R5 is hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; anionic group; substituted or unsubstituted alkoxy group; substituted or unsubstituted Alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate group; substituted or unsubstituted amine group; substituted or unsubstituted alkenyl group Selected from the group consisting of aryl groups; and substituted or unsubstituted heteroaryl groups,
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
r5 is an integer from 0 to 3, and when r5 is 2 or more, R5 is the same as or different from each other.

As used herein, the R5 is hydrogen; or deuterium.

In the present specification, the R5 is hydrogen.

［化学式７］

前記化学式６および化学式７において、
Ｒ１、Ｒ２、Ｒ４、Ｒ４１、Ｒ４２、Ｌ、Ｍ、ｒ１、ｒ２、ｒ４、ｒ４１およびｒ４２は、前記化学式１で定義した通りであり、
Ｒ６は、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；−ＣＯＲ；−ＣＯＯＲ；イミド基；アミド基；陰イオン性基；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のシクロアルケニル基；置換もしくは非置換のスルホネート基；置換もしくは非置換のアミン基；置換もしくは非置換のアリール基；および置換もしくは非置換のヘテロアリール基からなる群より選択され、
前記Ｒは、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であり、
ｒ６は、０〜３の整数であり、ｒ６が２以上の場合、Ｒ６は、互いに同一または異なる。 According to another embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 6 or chemical formula 7.
[Chemical formula 6]

[Chemical formula 7]

In the chemical formulas 6 and 7,
R1, R2, R4, R41, R42, L, M, r1, r2, r4, r41 and r42 are as defined in Chemical Formula 1.
R6 is hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; imide group; amide group; anionic group; substituted or unsubstituted alkoxy group; substituted or unsubstituted Alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate group; substituted or unsubstituted amine group; substituted or unsubstituted alkenyl group Selected from the group consisting of aryl groups; and substituted or unsubstituted heteroaryl groups,
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
r6 is an integer from 0 to 3, and when r6 is 2 or more, R6 is the same as or different from each other.

Further, in the present specification, the R6 is hydrogen; or deuterium.

In the present specification, the R6 is hydrogen.

［化学式５−１］

前記化学式４−１および化学式５−１において、
Ｒ２〜Ｒ５、Ｒ４１、Ｒ４２、Ｌ、Ｍ、ｒ２〜ｒ５、ｒ４１およびｒ４２は、前記化学式４および化学式５で定義した通りである。 In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 4-1 or chemical formula 5-1.
[Chemical formula 4-1]

[Chemical formula 5-1]

In the chemical formulas 4-1 and 5-1.
R2 to R5, R41, R42, L, M, r2 to r5, r41 and r42 are as defined in the above chemical formulas 4 and 5.

［化学式７−１］

前記化学式６−１および化学式７−１において、
Ｒ１、Ｒ２、Ｒ４、Ｒ６、Ｒ４１、Ｒ４２、Ｌ、Ｍ、ｒ１、ｒ２、ｒ４、ｒ６、ｒ４１およびｒ４２は、前記化学式６および化学式７で定義した通りである。 In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 6-1 or chemical formula 7-1.
[Chemical formula 6-1]

[Chemical formula 7-1]

In the chemical formulas 6-1 and 7-1,
R1, R2, R4, R6, R41, R42, L, M, r1, r2, r4, r6, r41 and r42 are as defined in Chemical Formula 6 and Chemical Formula 7.

前記化学式１−１において、
Ｒ１〜Ｒ３、ｒ１およびｒ２は、前記化学式１で定義した通りであり、
Ｒ３１は、水素；重水素；置換もしくは非置換のスルホネート基；または置換もしくは非置換の窒素原子を含む二無水物基であり、
ｒ３−１は、０〜３の整数であり、ｒ３−１が２以上の場合、Ｒ３は、同一または異なる。 In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-1.
[Chemical formula 1-1]

In the chemical formula 1-1
R1 to R3, r1 and r2 are as defined in Chemical Formula 1 above.
R31 is a dianhydride group containing hydrogen; deuterium; a substituted or unsubstituted sulfonate group; or a substituted or unsubstituted nitrogen atom.
r3-1 is an integer of 0 to 3, and when r3-1 is 2 or more, R3 is the same or different.

In R31 of Chemical Formula 1-1, the substituted or unsubstituted sulfonate group and the substituted or unsubstituted nitrogen atom-containing dianhydride group are as described above.

［化学式Ｎ］

［化学式Ｍ］

前記化学式Ｓ、化学式Ｎ、および化学式Ｍにおいて、

は、前記化学式１に連結される部位を示し、
Ａは、置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；または置換もしくは非置換のアリール基であり、
Ｂは、−Ｘ−Ｘ'−または−Ｘ＝Ｘ'−であり、
ＸおよびＸ'は、ＣＲ_１１Ｒ_１２であり、
Ｒ_１１、Ｒ_１２は、互いに同一または異なり、それぞれ独立に、水素；重水素；Ｎ；またはＳであるか、隣接する基は、互いに結合して環を形成し、
Ｚ１〜Ｚ３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であるか、隣接する基は、互いに結合して環を形成してもよい。 In one embodiment of the specification, at least one of the R3s may be represented by hydrogen; the following chemical formula S, chemical formula N, or chemical formula M.
[Chemical formula S]

[Chemical formula N]

[Chemical formula M]

In the chemical formula S, the chemical formula N, and the chemical formula M,

Indicates a site linked to the above chemical formula 1.
A is a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
B is -X-X'-or -X = X'-,
X and X'are CR ₁₁ R ₁₂ and
R ₁₁ and R ₁₂ are the same or different from each other and are independently hydrogen; deuterium; N; or S, or adjacent groups are bonded to each other to form a ring.
Z1 to Z3 are the same or different from each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group, or adjacent groups are bonded to each other. May form a ring.

In the chemical formula S, the chemical formula N, and the chemical formula M, A, B and Z1 to Z3 are as described above.

According to another embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas, but is not necessarily limited thereto.

In addition, one embodiment of the present specification provides a coloring material composition containing the compound represented by the chemical formula 1.

The color material composition may further contain at least one of a dye and a pigment in addition to the compound of the chemical formula 1. For example, the coloring material composition may contain only the compound of the chemical formula 1, but may contain 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. It may contain the compound of Chemical Formula 1, one or more dyes, and one or more pigments.

One embodiment of the present specification provides a photosensitive resin composition containing the colorant composition.

One embodiment of the present specification provides a photosensitive resin composition comprising the compound represented by the chemical formula 1, a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of the film produced by the photosensitive resin composition.

As the binder resin, a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility can be used, and a binder generally used in the art may be further contained. ..

The polyfunctional monomer that imparts mechanical strength to the film is any one or more of unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. There may be.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and 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 , 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl Ether (meth) acrylate, phenoxydiethylene glycol (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, methyl α-hydroxymethyl acrylate , Ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate, and butyl α-hydroxymethyl acrylate may be selected from the group, but is not limited thereto.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p) -chloro. It may be selected from the group consisting of styrene, but is not limited to these.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

Specific examples of the unsaturated imides may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. , Not limited to these.

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

The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group, and for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2- Selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethylphthalate, mono-2-((meth) acryloyloxy) ethylsuccinate, ω-carboxypolycaprolactone mono (meth) acrylate. It is preferable to use one or more, but the present invention is not limited to these.

According to one embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOHmg / g, and the weight average molecular weight is 1,000 to 50,000 g / mol.

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

In one embodiment of the present specification, the binder resin may be a copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30).

The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6 -Hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, penta It may be one or a mixture of two or more selected from the group consisting of erythritol tetramethacrylate and dipentaerythritol hexamethacrylate.

In one embodiment of the present specification, the polyfunctional monomer may be DPHA (Dipentaerythritol hexacrylate).

The photoinitiator is not particularly limited as long as it is an initiator that promotes cross-linking by generating radicals with light, but is selected from the group consisting of, for example, an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound. It may be one or more kinds to be processed.

The acetphenone compounds are 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) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-Methyl- (4-methylthio) Phenyl-2-morpholino-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, 2-( 4-Bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one And are not limited to these.

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

The triazine compounds are 3-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, cyclohexyl-2-{4- [ 2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} Acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s -Triazine-6-yl] phenylthio} propionamide, 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 not limited to these.

The oxime compounds are 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigy, CGI124), etanone, -1- (9-ethyl) -6. -(2-Methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGI242), N-1919 (Adeca), and the like, and are not limited thereto.

In one embodiment of the specification, the photoinitiator may be I-369 (BASF).

The solvents used are 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, and diethylene glycol diethyl ether. , Diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, propylene glycol ethyl One or more selected from the group consisting of ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether. There may be, but it is not limited to this.

In one embodiment of the specification, the solvent may be propylene glycol monomethyl ether acetate.

In one embodiment of the present specification, the content of the compound represented by the chemical formula 1 is 5% by weight to 60% by weight, and the content of the binder resin is based on the total weight of the photosensitive resin composition. Is 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is 0.1% by weight to 50% by weight. Provided is a photosensitive resin composition in which the content of the additive is 0.1% by weight to 10% by weight and the content of the solvent is 10% by weight to 80% by weight.

According to one embodiment of the present specification, the content of the compound represented by the chemical formula 1 is 5% by weight to 60% by weight based on the total weight of the solid content in the photosensitive resin composition. The content of the binder resin is 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is 0.1% by weight. % To 50% by weight.

The total weight of the solid content means the total weight of the components excluding the solvent from the photosensitive resin composition. The weight% reference based on the solid content and the solid content of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.

According to one embodiment of the present specification, the photosensitive resin composition may further contain an additive.

According to one embodiment of the present specification, the photosensitive resin composition comprises a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a dispersant. It may additionally contain one or more additives selected from the group consisting of leveling agents.

According to one 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.

In one embodiment of the specification, the additive may be a surfactant.

According to one embodiment of the present specification, the content of the surfactant is 0.1% by weight to 10% by weight based on the total weight of the photosensitive resin composition.

According to one embodiment of the present specification, the content of the surfactant is 0.1% by weight to 10% by weight based on the total weight of the solid content in the photosensitive resin composition.

The photocrosslinking sensitizers include benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3, Benzophenone compounds such as 3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 -Fluolenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; xanthone, 2-methylxanthone, etc. Xanthone compounds; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylaclydin, 1,7-bis ( Acrydin compounds such as 9-acrydinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7,7-trimethyl-bicyclo [2] , 2,1] Dicarbonyl compounds such as heptane-2,3-dione, 9,10-phenanthrenquinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4 , 4-trimethylpentylphosphine oxide and other phosphine oxide compounds; methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate and the like. Benzophenone compounds; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl -Amino synergists such as cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-Benzoyl-7-methoxy-coumarin, 10,10-carboni Rubis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolidine-11-one, etc. One or more selected from the group consisting of chalcone compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthiazoline; can be used. ..

The curing accelerator is used to enhance curing and mechanical strength, and specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-Thiazazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2) -Selected from the group consisting of pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) 1 More than seeds can be used.

Adhesion promoters used herein include metaacryloylsilane coupling agents such as metaacryloyloxypropyltrimethoxysilane, metaacryloyloxypropyldimethoxysilane, metaacryloyloxypropyltriethoxysilane, and metaacryloyloxypropyldimethoxysilane. One or more of them can be selected and used, and as the alkyltrimethoxysilane, one or more can be selected and used from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like. ..

The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK of BYK-Chemie. -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 and the like can be used, and as the fluorine-based surfactant, F-114, F-177, F-410, F-411, F-450, F-493, F of DIC (Dai Nippon Inc & Chemicals) can be used. -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-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. can be used, but are limited thereto. is not it.

In one embodiment of the present specification, the surfactant may be F-475 of DIC Corporation.

The antioxidant is one or more selected from the group consisting of a hidden phenolic antioxidant, an amine-based antioxidant, a thio-based antioxidant, and a phosphine-based antioxidant. It may be, but it is not limited to this.

Specific examples of the antioxidants include phosphate-based heat stabilizers such as phosphoric acid, trimethyl phosphate, or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-). Hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [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, 3,5-di-t-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4) -Methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- 6-t-butylphenol) or bis [3,3-bis- (4'-hydroxy-3'-tart-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-) Hindered phenolic primary antioxidants such as 3'-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylene. Diamines, or amine-based secondary antioxidants such as N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole , Or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Thio-based secondary antioxidants such as methane; or triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-Dibutylphenyl) Pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Phenaerythritol Diphosphite, or (1,1'-biphenyl) -4,4'-diylbisphosphonoate tetrakis [2,4] -Bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphonous acid Examples include phosphite-based secondary antioxidants such as tetrakis [2,4-bis (1,1-dimethyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone and the like can be used, but the ultraviolet absorber is not limited thereto. Anything commonly used in the industry can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine aluminum salt. , P-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2-methylenebis (4-methyl-6-t) It can include, but is not limited to, one or more selected from the group consisting of −butylphenol), 2-mercaptoimidazole, and phenothiazine, but is generally known in the art. May include those that are.

The dispersant can be used by internally adding the pigment to the pigment in the form of surface treatment in advance, or by externally adding the pigment to the pigment. As the dispersant, a compound type, nonionic, anionic, or cationic dispersant can be used, and a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric interface can be used. Activators and the like can be mentioned. These can be used individually or in combination of two or more.

Specifically, the dispersant includes polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, and carboxylic acid. There is, but is not limited to, one or more selected from the group consisting of salts, alkylamide alkylene oxide adducts, and alkylamines.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymer-based leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-. All commonly used in the art can be used, including but not limited to containing and non-polymeric nitrogen-containing compounds.

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

More specifically, the photosensitive resin composition of the present specification can be applied onto a substrate by an appropriate method and cured to produce a thin film or patterned photosensitive material.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and the spin coating method is generally widely used. Further, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.

Light sources for curing the photosensitive resin composition according to the present specification include, for example, mercury vapor arc (arc), carbon arc, Xe arc, etc. that emit light having a wavelength of 250 nm to 450 nm, but these are not necessarily the same. Not limited to.

The photosensitive resin composition according to the present specification includes a pigment dispersion type photosensitive material for manufacturing a thin film liquid crystal display device (TFT LCD) color filter, a light film thin film display device (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode. For overcoat layer forming photosensitive material, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printing wiring board, photosensitive material for plasma display panel (PDP), etc. It can be used, and there are no particular restrictions on its use.

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

The color filter can be produced by using a photosensitive resin composition containing the compound represented by the chemical formula 1. A photosensitive material can be produced by applying the photosensitive resin composition onto a substrate to form a coating film, and exposing, developing and curing the coating film, and a color filter containing the same can be provided.

The photosensitive resin composition according to one embodiment of the present specification is excellent in heat resistance, has little color change due to heat treatment, has a high color reproduction rate even during the manufacturing and curing process of a color filter, and has a brightness and a light-dark ratio. Can provide a high color filter.

The substrate may be a glass plate, a silicon wafer, and a plate of a plastic base material such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited. Absent.

Specifically, the photosensitive resin composition according to one embodiment of the present specification ^{is spin-coated on glass (5 × 5 cm 2} ) and preheated (prebake) at 100 ° C. for 100 seconds to form a film. Can be formed. The distance between the substrate on which the film is formed and the photomask (photomask) is set to 250 um, and the entire surface of the substrate is irradiated with an exposure amount ^{of 40 mJ / cm 2 using an exposure device.} After that, the exposed substrate can be developed in a developing solution (potassium hydroxide (KOH), 0.05%) for 60 seconds and then heat-treated (postbake) at 230 ° C. for 20 minutes to prepare a substrate.

The heat resistance evaluation is measured by a method described later. The substrate produced by the above embodiment is used with a spectroscope to obtain a transmittance spectrum in the visible light region in the range of 380 nm to 780 nm. Further, the preheat treatment (prebake) substrate is additionally subjected to postheat treatment (postbake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum in the same equipment and measurement range.

The spectroscope may be of MCPD-Otsuka, but is not limited thereto.

Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter referred to as ΔEab) is calculated using the obtained values E (L *, a *, b *). A small ΔEab value means that the color heat resistance is excellent. When it has a value of ΔEab <3, it can be used as a dye for a color filter, and it can be said that it is a coloring material having excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.
[Calculation formula 1]
ΔEab (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2

The color filter can 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.

A grid-like black pattern called a black matrix can be arranged between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material for the black matrix. In this case, a method may be used in which chromium is vapor-deposited on the entire glass substrate and a pattern is formed by an etching process. However, in consideration of high cost in the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, a resin black matrix obtained by a pigment dispersion method capable of fine processing can be used.

The black matrix can use a black pigment or a black dye as a coloring material. For example, carbon black can be used alone or a mixture of carbon black and a coloring pigment can be used. At this time, since the coloring pigment having insufficient light-shielding property is mixed, the amount of the coloring material is relatively large. There is an advantage that the strength of the film or the adhesion to the substrate does not decrease even if the amount is increased.

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

The display device includes a plasma display panel (Plasma Display Panel, PDP), a light emitting diode (Light Emitting Device, LED), an organic light emitting element (Organic Light Emitting Device, OLED), a liquid crystal display device (Liquid Crystal Disk), and a liquid crystal display device (Liquid Crystal Display). It may be any one of a liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (Cathode Ray Tube, CRT).

Hereinafter, in order to specifically explain the present specification, examples will be given and described in detail. However, the embodiments according to the present specification can be transformed into various different forms, and the scope of the present specification is not construed as being limited to the examples described below. The examples herein are provided to provide a more complete description of the specification to those with average knowledge in the art.

<Example>

<Example of Synthesis of Colorant Compound>

Synthesis Example 1: Synthesis of Compound 1

In a 100 ml 2-neck-round bottom flask (RBF, Round Bottom Flask), 25 g of methylbenzoate, A-12 g (12.642 mmol), and B-1 1.873 g (12.642 mmol) are placed and stirred. I let you. Specifically, the reaction was carried out at 180 ° C. for 12 hours.

After this, 2.429 g (12.642 mmol) of D-1 was added, and the mixture was additionally reacted at 180 ° C. for 12 hours. The reaction was cooled to room temperature and precipitated in 250 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and then dried in a vacuum oven at 80 ° C. to give compound 1 and the next reaction proceeded without additional separation.

In a 250 ml 2-neck-round bottom flask (RBF, Round Bottom Flash), 80 g of dimethylformamide (DMF, Dimethylformamide) was placed, and 15 g (10.83 mmol) of the intermediate and 2.725 g of sodium hydrogen carbonate (NaHCO ₃ ) were placed. (30.439 mmol) was added, the temperature was raised to 50 ° C., and the mixture was stirred to prepare a reaction solution.

Then, 2.899 g (10.813 mmol) of E-1 was gradually added to the reaction solution, and the mixture was stirred at 120 ° C. for 4 hours. After that, the reaction solution was cooled to room temperature and precipitated in 1800 ml of distilled water (DI-Water). After precipitation, the precipitate was filtered under reduced pressure and washed with water. The precipitate was dried under reduced pressure. Compound 1 5.2 g (8.010 mmol) was obtained.

Ionization mode APCI +: m / z = 650 [M + H], Exact Mass: 649

Synthesis example 2: Synthesis of compound 2

In a 250 ml 2-neck-round bottom flask (RBF, Round Bottom Flash), 100 ml of 6M hydrochloric acid (HCl) is added, and then 9.135 g (66.61 mmol) of A-2 is further added to raise the temperature to 100 ° C. Then, the mixture was stirred for 30 minutes to prepare the reaction solution 1. Then, 9.34 g (133.21 mmol) of A-3 was gradually added to the reaction solution 1.

After that, the mixture was further stirred at 100 ° C. for 2 hours. Next, the reaction solution was cooled to room temperature, and the precipitate was filtered under reduced pressure. The precipitate was recrystallized from 250 ml of ethanol (EtOH). Then, it was filtered under reduced pressure to obtain 7.3 g (38.995 mmol) of A-4.

Next, 25 g of methylbenzoate, A-4 2.366 (12.642 mmol) and B-1 1.873 g (12.642 mmol) were added and stirred. Specifically, the reaction solution 2 was produced by reacting at 180 ° C. for 12 hours.

After that, the reaction solution 2 was cooled to room temperature and precipitated in 250 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and then dried in a vacuum oven at 80 ° C. to give Intermediate 2 and the next reaction proceeded without additional separation.

In a 250 ml 2-neck-round bottom flask (RBF, Round Bottom Flash), 80 g of dimethylformamide (DMF, Dimethylformamide) was placed, and intermediate 23.431 g (10.831 mmol) and sodium hydrogen carbonate (NaHCO ₃ ) 2 were placed. .725 g (30.439 mmol) was added, the temperature was raised to 50 ° C., and the mixture was stirred to prepare a reaction solution 3.

Then, 2.899 g (10.813 mmol) of E-1 was gradually added to the reaction solution 3, and the mixture was stirred at 120 ° C. for 4 hours. The stirred solution was cooled to room temperature and precipitated in 1800 ml of distilled water (DI-Water). The precipitate was filtered under reduced pressure and washed with water, and then the precipitate was dried under reduced pressure to obtain 3.577 g (7.090 mmol) of Compound 2.

Ionization mode APCI +: m / z = 505 [M + H], Exact Mass: 504

Synthesis Example 3: Synthesis of Compound 3

Methylbenzoate (25 g), A-5 2.366 g (12.642 mmol) and B-1 1.873 g (12.642 mmol) were added and stirred. The reaction solution 1 was produced by reacting at 180 ° C. for 12 hours.

After that, the reaction solution 1 was cooled to room temperature and precipitated in 250 g of methanol (MeOH). The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and then dried in a vacuum oven at 80 ° C. to give Intermediate 2 and the next reaction proceeded without additional separation.

In a 250 ml 2-neck-round bottom flask (RBF, Round Bottom Flash), 80 g of dimethylformamide (DMF, Dimethylformamide) was placed, and the intermediate 33.431 g (10.831 mmol) and sodium hydrogen carbonate (NaHCO ₃ ) 2 were placed. .725 g (30.439 mmol) was added, the temperature was raised to 50 ° C., and the mixture was stirred to prepare a reaction solution 2.

Then, 2.899 g (10.813 mmol) of E-1 was gradually added to the reaction solution 2, and the mixture was stirred at 120 ° C. for 4 hours. After stirring, the mixture was cooled to room temperature (25 ° C.) and precipitated in 1800 ml of distilled water (DI-Water). The precipitate was filtered under reduced pressure and washed with water. The precipitate was dried under reduced pressure to give 3.592 g (7.12 mmol) of compound 3.

Ionization mode APCI +: m / z = 505 [M + H], Exact Mass: 504

Synthesis Example 4: Synthesis of Compound 4

In a 100 ml 2-neck-Round Bottom Flask (RBF, Round Bottom Flask), 25 g of Methylbenzoate, 2.443 g (12.642 mmol) of A-6, and 2.429 g (12.642 mmol) of D-1 are placed. Then, the reaction was carried out at 180 ° C. for 12 hours.

The reaction was cooled to room temperature and precipitated in 250 g of MeOH. The mixture was stirred for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. to give compound 4 and the next reaction proceeded without additional separation.

In a 250 ml 2-neck-round bottom flask (RBF, Round Bottom Flask), 80 g of dimethylformamide (DMF, Dimethylformamide) was placed, and intermediate 43.972 g (10.83 mmol), sodium hydrogen carbonate (NaHCO ₃ ) 2 .725 g (30.439 mmol) was added, the temperature was raised to 50 ° C., and the mixture was stirred.

Then, 2.899 g (10.813 mmol) of E-1 was gradually added to the reaction solution, and the mixture was stirred at 120 ° C. for 4 hours. The reaction solution was cooled to room temperature and precipitated in 1800 ml of distilled water (DI-Water). The precipitate was filtered under reduced pressure, washed with water and dried under reduced pressure to give 5.127 g (9.245 mmol) of compound 4.

Ionization mode APCI +: m / z = 555 [M + H], Exact Mass: 554

Synthesis Example 5: Synthesis of Compound 5

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 5, and Compound 5 was synthesized by the same method.

Ionization mode APCI +: m / z = 700 [M + H], Exact Mass: 699

Synthesis Example 6: Synthesis of Compound 6

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 6, and Compound 6 was synthesized by the same method.

Ionization mode APCI +: m / z = 600 [M + H], Exact Mass: 599

Synthesis Example 7: Synthesis of Compound 7

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 7, and Compound 7 was synthesized by the same method.

Ionization mode APCI +: m / z = 556 [M + H], Exact Mass: 555

Synthesis Example 8: Synthesis of Compound 8

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 8 and Compound 8 was synthesized by the same method.

Ionization mode APCI +: m / z = 654 [M + H], Exact Mass: 653

Synthesis Example 9: Synthesis of Compound 9

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 9, and Compound 9 was synthesized by the same method.

Ionization mode APCI +: m / z = 654 [M + H], Exact Mass: 653

Synthesis Example 10: Synthesis of Compound 10

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 10, and Compound 10 was synthesized by the same method.

Ionization mode APCI +: m / z = 700 [M + H], Exact Mass: 699

Synthesis Example 11: Synthesis of Compound 11

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 11, and Compound 11 was synthesized by the same method.

Ionization mode APCI +: m / z = 651 [M + H], Exact Mass: 650

Synthesis Example 12: Synthesis of Compound 12

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 12, and Compound 12 was synthesized by the same method.

Ionization mode APCI +: m / z = 711 [M + H], Exact Mass: 710

に変更し、同様の方法により化合物１３〜２４を合成した。

Synthesis Examples 13 to 24: Synthesis of Compounds 13 to 24 Intermediates 1 to 12 are used in place of E-1.

Compounds 13 to 24 were synthesized by the same method.

Compound 13: Ionization mode APCI +: m / z = 700 [M + H], Exact Mass: 699
Compound 14: Ionization mode APCI +: m / z = 555 [M + H], Exact Mass: 554
Compound 15: Ionization mode APCI +: m / z = 555 [M + H], Exact Mass: 554
Compound 16: Ionization mode APCI +: m / z = 605 [M + H], Exact Mass: 604
Compound 17: Ionization mode APCI +: m / z = 750 [M + H], Exact Mass: 749
Compound 18: Ionization mode APCI +: m / z = 650 [M + H], Exact Mass: 649
Compound 19: Ionization mode APCI +: m / z = 606 [M + H], Exact Mass: 605
Compound 20: Ionization mode APCI +: m / z = 704 [M + H], Exact Mass: 703
Compound 21: Ionization mode APCI +: m / z = 704 [M + H], Exact Mass: 703
Compound 22: Ionization mode APCI +: m / z = 750 [M + H], Exact Mass: 749
Compound 23: Ionization mode APCI +: m / z = 701 [M + H], Exact Mass: 700
Compound 24: Ionization mode APCI +: m / z = 761 [M + H], Exact Mass: 760

Compound of Comparative Example A colorant (PY138) having the following structural formula was obtained from BASF and used as a compound of Comparative Example.

<Production Example of Photosensitive Resin Composition>

Example 1
5.554 g of compound 1, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 g measured by gel permeation chromatography (GPC)). / Mol), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent propylene glycol monomethyl ether acetate (including PGMEA, Propyrene glycol monomer ether acetate) 10.376 g, as a photoinitiator 2.018 g of I-369 (BASF), 12.443 g of DPHA (Nippon Kayaku) as a photopolymerizable compound of polyfunctional monomer, 68.593 g of solvent PGMEA (propylene glycol monomethyl ether acetate), and surface activity of additives. 1.016 g of F-475 manufactured by DIC was mixed as an agent to produce the photosensitive resin composition of Example 1.

Examples 2-24
The photosensitive resin compositions of Examples 2 to 24 were produced with the same composition as the photosensitive resin composition of Example 1 except that Compound 1 in Example 1 was changed to Compounds 2 to 24.

Comparative Example Compound PY138 5.554 g of Comparative Example, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average measured by gel permeation chromatography (GPC)). Molecular weight 20,000 g / mol), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent propylene glycol monomethyl ether acetate (including PGMEA, Compound glycol monomer ether acetate) 10.376 g, light 2.018 g of I-369 (BASF) as an initiator, 12.443 g of DPHA (Nippon Kayaku) as a photopolymerizable compound of polyfunctional monomer, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and addition. 1.016 g of F-475 manufactured by DIC was mixed as an agent to produce a photosensitive resin composition of Comparative Example.

<Experimental example>

Evaluation of solubility Compounds 1 to 24 and a compound of Comparative Example (PY138) were prepared, and the solubility in 100 g of dimethylformamide (DMF, Dimethylformamide) was measured at 25 ° C. and 1 atm, and the results are shown in Table 1 below. When the solubility was 1% or more, it was displayed as O, and when it was less than 1%, it was displayed as X.

With reference to Table 1 above, it was found that the coloring materials of Compounds 1 to 24 of the present invention had better solubility in an organic solvent (dimethylformamide) than the compound of Comparative Example (PY138).

Generally, in the case of a pigment, it is insoluble in an organic solvent and needs to be dispersed with a derivative, a dispersant or the like. However, when it is dissolved in an organic solvent as in Examples 1 to 24 according to the present specification, a derivative or a dispersant is not required, the amount used can be reduced, and it is commercially applicable.

Preparation of Substrate The photosensitive resin compositions of Examples 1 to 24 were used for preparing a substrate, respectively. Specifically, the photosensitive resin compositions of Examples 1 to 24 ^{are spin-coated on glass (5 × 5 cm 2} ) and preheat-treated (prebake) at 100 ° C. for 100 seconds to form a film. It was formed.

The distance between the substrate on which the film was formed and the photomask (photomask) was set to 250 um, and the entire surface of the substrate was irradiated with an exposure amount ^{of 40 mJ / cm 2 using an exposure device.}

Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and then heat-treated (postbake) at 230 ° C. for 20 minutes to prepare a substrate.

Heat resistance evaluation A transmittance spectrum in the visible light region in the range of 380 nm to 780 nm was obtained using a spectroscope (MCPD-Otsuka Co., Ltd.) on the substrate prepared by the method for producing the substrate. Further, the preheat-treated (prebake) substrate was additionally post-heat-treated (postbake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum with the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter, ΔEab) was calculated by the following formula 1 using the obtained values E (L *, a *, b *), and the following Table 2 It was shown to.

A small ΔEab value means that the color heat resistance is excellent.

When it has a value of ΔEab <3, it can be used as a dye for a color filter, and it can be said that it is a coloring material having excellent heat resistance.
[Equation 1]
ΔEab (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2

Referring to Table 2 above, the color pattern substrate formed by using the photosensitive resin compositions of Examples 1 to 24 of the present invention has a transmittance spectrum difference (ΔEab) of less than 3 after the pre-heat treatment and the post-heat treatment. Therefore, it was confirmed that the color stability was high, the amount was very small, and the heat resistance was excellent.

Claims (14)

Compound represented by the following chemical formula 1:
[Chemical formula 1]

In the chemical formula 1,
At least one of R1 and R3 is represented by the following chemical formula 2 or chemical formula 3.
R2 is hydrogen; deuterium; halogen group; a nitrile group; a nitro group; a hydroxyl group; -COR; -COOR; preparative Riffle ol methanesulfonate anion, bis (trifluoromethylsulfonyl) amide anion, bis trifluoromethane sulfonimide anion, bis par fluoroalkyl sulfone imide anions, tetraphenylborate anion; tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethanesulfonyl methide; SO 3 ^_-; CO _{^{2 -; SO 2 N - SO}} 2 CF 3; SO 2 N - SO 2 CF 2 CF 3; a halogen group; a sulfonic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted Cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted sulfonate group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; substituted or unsubstituted Heteroaryl group; and selected from the group consisting of dianhydride groups containing substituted or unsubstituted nitrogen atoms.
[Chemical formula 2]

[Chemical formula 3]

In the chemical formulas 2 and 3,

Indicates a site linked to the above chemical formula 1.
X is O; or NH,
L is a substituted or unsubstituted alkylene group; a substituted or unsubstituted heteroalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.
M is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted heteroalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; or a substituted or unsubstituted divalent It is a dianhydride group containing a nitrogen atom and
Of R1 and R3, those which are not the chemical formula 2 or the chemical formula 3, R4, R41 and R42 are the same or different from each other, and independently, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; -COR; -COOR; scan sulfonic acid group; trifluoromethanesulfonic acid anions, bis (trifluoromethylsulfonyl) amide anion, bis trifluoromethane sulfonimide anion, bis par fluoroalkyl sulfone imide anions, tetraphenylborate anion ion; tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethanesulfonyl ^{_{methide; SO 3 -; CO 2 -}} ; SO 2 N - SO 2 CF 3; SO 2 N - SO 2 CF ₂ CF ₃ ; halogen group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted Alternatively, from the group consisting of an unsubstituted sulfonate group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a dianhydride group containing a substituted or unsubstituted nitrogen atom. Selected and adjacent groups may combine with each other to form a ring.
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
The dianhydride group containing a nitrogen atom is represented by the following chemical formula N or chemical formula M.
[Chemical formula N]

[Chemical formula M]

In the chemical formula N and the chemical formula M, B is -X-X'-, X and X'are CR ₁₁ R ₁₂ , and R ₁₁ and R ₁₂ are the same or different from each other and are independently hydrogen. Deuterium; N; or S or adjacent groups are bonded to each other to form a ring, and Z1 to Z3 are the same or different from each other and are independent of each other, hydrogen; deuterium; halogen group; substituted or An unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring.
r1 and r3 are integers of 1 to 4, and when r1 and r3 are 2 or more, R1 and R3 are the same or different, respectively.
r4 is an integer from 0 to 4, and when r4 is 2 or more, R4 is the same or different.
r2 is an integer from 0 to 2, and when r2 is 2, R2 is the same or different,
r41 and r42 are integers from 0 to 3, and when r41 and r42 are 2 or more, R41 and R42 are the same or different, respectively. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4 or chemical formula 5.
[Chemical formula 4]

[Chemical formula 5]

In the chemical formulas 4 and 5,
R2 to R4, R41, R42, L, M, r2 to r4, r41 and r42 are as defined in Chemical Formula 1 above.
R5 is hydrogen; deuterium; halogen group; a nitrile group; a nitro group; a hydroxyl group; -COR; -COOR; preparative Riffle ol methanesulfonate anion, bis (trifluoromethylsulfonyl) amide anion, bis trifluoromethane sulfonimide anion, bis par fluoroalkyl sulfone imide anions, tetraphenylborate anion; tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethanesulfonyl methide; SO 3 ^_-; CO _{^{2 -; SO 2 N - SO}} 2 CF 3; SO 2 N - SO 2 CF 2 CF 3; a halogen group; a sulfonic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted Cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted cycloalkenyl groups; substituted or unsubstituted sulfonate groups; substituted or unsubstituted amine groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted Selected from the group consisting of substituted heteroaryl groups
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
r5 is an integer from 0 to 3, and when r5 is 2 or more, R5 is the same as or different from each other. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 6 or chemical formula 7.
[Chemical formula 6]

[Chemical formula 7]

In the chemical formulas 6 and 7,
R1, R2, R4, R41, R42, L, M, r1, r2, r4, r41 and r42 are as defined in Chemical Formula 1.
R6 is hydrogen; deuterium; halogen group; a nitrile group; a nitro group; a hydroxyl group; -COR; -COOR; preparative Riffle ol methanesulfonate anion, bis (trifluoromethylsulfonyl) amide anion, bis trifluoromethane sulfonimide anion, bis par fluoroalkyl sulfone imide anions, tetraphenylborate anion; tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethanesulfonyl methide; SO 3 ^_-; CO _{^{2 -; SO 2 N - SO}} 2 CF 3; SO 2 N - SO 2 CF 2 CF 3; a halogen group; a sulfonic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted Cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted cycloalkenyl groups; substituted or unsubstituted sulfonate groups; substituted or unsubstituted amine groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted Selected from the group consisting of substituted heteroaryl groups
The R is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
r6 is an integer from 0 to 3, and when r6 is 2 or more, R6 is the same as or different from each other. The compound according to claim 2, wherein the chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 5-1.
[Chemical formula 4-1]

[Chemical formula 5-1]

In the chemical formulas 4-1 and 5-1.
R2 to R5, R41, R42, L, M, r2 to r5, r41 and r42 are as defined in the above chemical formulas 4 and 5. The compound according to claim 3, wherein the chemical formula 1 is represented by the following chemical formula 6-1 or chemical formula 7-1.
[Chemical formula 6-1]

[Chemical formula 7-1]

In the chemical formulas 6-1 and 7-1,
R1, R2, R4, R6, R41, R42, L, M, r1, r2, r4, r6, r41 and r42 are as defined in Chemical Formula 6 and Chemical Formula 7. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1.
[Chemical formula 1-1]

In the chemical formula 1-1
R1 to R3, r1 and r2 are as defined in Chemical Formula 1 above.
R31 is a dianhydride group containing hydrogen; deuterium; a substituted or unsubstituted sulfonate group; or a substituted or unsubstituted nitrogen atom.
The dianhydride group containing a nitrogen atom is represented by the following chemical formula N or chemical formula M.
[Chemical formula N]

[Chemical formula M]

In the chemical formula N and the chemical formula M, B is -X-X'-, X and X'are CR ₁₁ R ₁₂ , and R ₁₁ and R ₁₂ are the same or different from each other and are independently hydrogen. Deuterium; N; or S or adjacent groups are bonded to each other to form a ring, and Z1 to Z3 are the same or different from each other and are independent of each other, hydrogen; deuterium; halogen group; substituted or An unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring.
r3-1 is an integer of 0 to 3, and when r3-1 is 2 or more, R3 is the same or different. At least one of the R3 is hydrogen; the compound according to any one of claims 1 to 6, represented by the following chemical formula S, chemical formula N, or chemical formula M:
[Chemical formula S]

[Chemical formula N]

[Chemical formula M]

In the chemical formula S, the chemical formula N, and the chemical formula M,

Indicates a site linked to the above chemical formula 1.
A is a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.
B is -X-X'-
X and X'are CR ₁₁ R ₁₂ and
R ₁₁ and R ₁₂ are the same or different from each other and are independently hydrogen; deuterium; N; or S, or adjacent groups are bonded to each other to form a ring.
Z1 to Z3 are the same or different from each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group, or adjacent groups are bonded to each other. May form a ring. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas:

A photosensitive resin composition comprising the compound according to any one of claims 1 to 8, a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent. Based on the total weight of the solid content in the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 5% by weight to 60% by weight.
The content of the binder resin is 1% by weight to 60% by weight.
The content of the photoinitiator is 0.1% by weight to 20% by weight.
The photosensitive resin composition according to claim 9, wherein the content of the polyfunctional monomer is 0.1% by weight to 50% by weight. The photosensitive resin composition according to claim 9 or 10, further comprising an additive. A photosensitive material containing the compound according to any one of claims 1 to 8. A color filter containing the photosensitive material according to claim 12. A display device including the color filter according to claim 13.