KR102636806B1 - Colorant composition, photosensitive resin composition, photo resist, color filter, and display device - Google Patents

Abstract

The present specification provides a colorant composition containing the compound represented by Formula 1, a photosensitive resin composition containing the same, a photosensitive material, a color filter, and a display device.

Description

Color material composition, photosensitive resin composition, photosensitive material, color filter, and display device {COLORANT COMPOSITION, PHOTOSENSITIVE RESIN COMPOSITION, PHOTO RESIST, COLOR FILTER, AND DISPLAY DEVICE}

This specification relates to colorant compositions and photosensitive resin compositions. Additionally, this specification relates to photosensitive materials, color filters, and display devices manufactured using the photosensitive resin composition.

Recently, performance featuring high brightness and high contrast ratio is required for color filters. Additionally, one of the main purposes of display device development is to differentiate display device performance by improving color purity and to improve productivity in the manufacturing process.

Since the type of pigment previously used as a coloring material in color filters exists in color photoresist in a dispersed particle state, it was difficult to control luminance and contrast ratio by controlling the size and distribution of pigment particles. In the case of pigment particles, they aggregate within the color filter, resulting in poor solubility and dispersibility, and multiple scattering of light occurs due to large aggregated particles. Scattering of such polarized light is pointed out as the main factor that reduces the contrast ratio. Efforts are continuing to improve luminance and contrast ratio through ultra-fine atomization and dispersion stabilization of pigments, but the degree of freedom in selecting color materials to implement color coordinates for high-color purity display devices is limited. In addition, pigment dispersion methods using already developed color materials, especially pigments, have reached their limits in improving the color purity, luminance, and contrast ratio of color filters using them.

Accordingly, there is a demand for the development of new color materials that can improve color reproduction, luminance, and contrast ratio by increasing color purity.

Korean Patent Publication No. 2001-0009058

The present inventors seek to provide a color material composition and a photosensitive resin composition, a photosensitive material manufactured using the same, a color filter, and a display device.

One embodiment of the present specification provides a colorant composition containing a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

M is a transition metal or post-transition metal,

X is a halogen group; Nitrile group; O(C=O)CH ₃ ; ONO ₂ ; or OSO ₂ ,

n is 0 or 1,

A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

a is an integer from 0 to 4, and when it is 2 or more, A1 is the same or different from each other,

b is an integer from 0 to 8, and when it is 2 or more, A2 is the same or different from each other,

c is an integer from 0 to 4, and when it is 2 or more, A3 is the same or different from each other,

R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

In the compound represented by Formula 1, the left and right substituents form an asymmetric structure with respect to the symmetry axis passing through M and X.

An exemplary embodiment of the present specification includes a colorant composition containing a compound represented by Formula 1; binder resin; multifunctional monomer; and a photoinitiator.

An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition or a cured product thereof.

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

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

A composition containing a compound according to an exemplary embodiment of the present specification can be used as a colorant for a display filter filter. The colorant composition of the present invention has excellent sensitivity, adhesion, solubility, and pattern formation, and is a new colorant for color filters.

1 is a diagram showing a fine pattern image of a comparative example.
Figures 2 to 5 are diagrams showing fine pattern images of Examples 1 to 4 including compounds A to D according to an exemplary embodiment of the present specification.

Hereinafter, this specification will be described in more detail.

According to an exemplary embodiment of the present specification, a colorant composition containing the compound represented by Chemical Formula 1 is provided. When the compound represented by Formula 1 is used as a colorant in a photosensitive resin composition, heat resistance and sensitivity can be improved, and a desired pattern can be formed.

The compound represented by Formula 1 is an organometallic compound, and the present inventor found that the photosensitive resin composition had excellent performance when applied to a color filter. Aromatic ring-C-N=C-C-N=C-Linkage of the aromatic ring can shift the bandgap and absorption spectrum through long conjugation.

In particular, the compound represented by the above formula (1) is characterized in that a metal element is introduced between polycyclic aromatic rings. In addition, the left and right substituents form an asymmetric structure based on the symmetry axis passing through the metal (M) of the parent core structure. In other words, the positions of the substituents connected to the left and right rings are different with respect to the line passing through M and Additionally, the left and right rings may be different.

According to one embodiment, the compound represented by the following formula (2) has strong asymmetry at the end of the polycyclic aromatic ring, which is the parent core structure, with a benzene ring and a naphthalene ring, and has excellent colorant performance.

In this specification, when a part “includes” a certain component, this means that it does not exclude other components but may further include other components, unless specifically stated to the contrary.

In this specification, means the connected part.

In this specification, the fact that the left and right substituents form a symmetrical structure with respect to the axis of symmetry means that the left and right substituents at the same distance from the axis of symmetry are all the same, and that the substituents on the left and right form an asymmetric structure with respect to the axis of symmetry means that the substituents on the left and right form an asymmetric structure based on the axis of symmetry. This means that even a pair of left and right substituents at the same distance are different.

Examples of substituents of the compound represented by Formula 1 are described below, but are not limited thereto.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; sulfonic acid group; sulfonate base; Nitrile group; nitro group; hydroxyl group; -COOH; Alkyl group; Cycloalkyl group; Haloalkyl group; alkenyl group; Amine group; Aryl group; heteroaryl group; Acryloyl group; Acrylate group; and a heterocyclic group containing at least one of N, O, or S atoms, or is substituted with one or more substituents selected from the group containing one or more of N, O, or S atoms, or does not have any substituent.

According to an exemplary embodiment of the present specification, the term “substituted or unsubstituted” means deuterium; halogen group; sulfonic acid group; sulfonate base; Nitrile group; nitro group; -COOH; Alkyl group; Cycloalkyl group; Haloalkyl group; Amine group; Aryl group; and is substituted or unsubstituted with one or more substituents selected from the group comprising a heteroaryl group.

According to an exemplary embodiment of the present specification, the term “substituted or unsubstituted” means deuterium; halogen group; nitro group; Alkyl group; Aryl group; and is substituted or unsubstituted with one or more substituents selected from the group comprising a heteroaryl group.

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In one embodiment of the present specification, the sulfonate group may be represented as -SO ₃ M, and M may be any one of the Group 1 elements of the periodic table, for example, Na, but is not limited thereto.

In an exemplary embodiment of the present specification, the amine group is -NH ₂ ; -ND ₂ ; -NDH; Alkylamine group; Cycloalkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but may be 1 to 30. Additionally, it may be 1 to 20, and may be 1 to 10. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, cycloalkylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl. -Anthracenylamine group, diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine 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, etc., but is not limited thereto.

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, and n-oxyl group. There is a til group, etc., but it is not limited to these.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25. Specific examples include alkenyl groups substituted with aryl groups such as stilbenyl and styrenyl, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20, and may also be 6 to 10. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may include a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, the heteroaryl group includes one or more atoms other than carbon, that is, heteroatoms. Specifically, the heteroaryl group may include one or more atoms selected from the group consisting of O, N, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene groups; furanyl group; pyrrole group; imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; pyridyl group; bipyridyl group; pyrimidyl group; Triazinyl group; triazolyl group; Acridyl group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyridopyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; indolyl group; carbazolyl group; Benzoxazolyl group; Benzimidazolyl group; benzothiazolyl group; benzocarbazolyl group; benzothiophene group; Dibenzothiophene group; Benzofuranyl group; phenanthrolinyl group; Isoxazolyl group; Thiadiazolyl group; Phenothiazinyl group; and dibenzofuranyl group, but are not limited thereto.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for those that are not monovalent.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from the examples of aryl groups above, excluding those that are not monovalent.

In the present specification, a heterocycle includes one or more atoms other than carbon and a heteroatom. Specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from among examples of the heteroaryl groups except for those that are not monovalent.

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

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

In this specification, '(meth)acryloyl' represents at least one type selected from the group consisting of acryloyl and methacryloyl. The notation ‘(meth)acrylate’ has the same meaning.

In this specification, OAc means -O(C=O)CH ₃ , and - is the position connected to the compound.

In this specification, NO ₃ means -ONO ₂ , and - is the position connected to the compound.

In this specification, SO ₃ means -OSO ₂ , and - is the position connected to the compound.

In this specification, a transition metal refers to a metal element in groups 3 to 12 of the periodic table, and a post-transition metal refers to a metal element among elements in groups 13 to 16 of the periodic table.

In an exemplary embodiment of the present specification, the right and left structures of Formula 1 are not the same based on the axis of symmetry of the parent core structure (the dotted line passing through metal M in the structure below).

In one embodiment of the present specification, M is a transition metal or a post-transition metal.

In one embodiment of the present specification, M is a transition metal.

In one embodiment of the present specification, M is a metal after transfer.

In one embodiment of the present specification, M is Zn, Co, Ni, Cu, Fe, Mn, Cr, Al, In, Sn, or Ga.

In one embodiment of the present specification, M is Zn, Co, Ni, Cu, Fe, Mn, or Cr.

In an exemplary embodiment of the present specification, M is Al, In, Sn, or Ga.

In one embodiment of the present specification, the M is Zn, Co, Cu, Fe, Mn, Cr, Al, In, or Ga.

In one embodiment of the present specification, X is a halogen group; Nitrile group; O(C=O)CH ₃ ; ONO ₂ ; Or OSO ₂ .

In one embodiment of the present specification, X is a halogen group; O(C=O)CH ₃ ; Or ONO ₂ .

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

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

In an exemplary embodiment of the present specification, M is Zn, Co, Ni, Cu, Fe, Mn, or Cr, and n is 0.

In an exemplary embodiment of the present specification, M is Al, In, Sn, or Ga, and n is 1.

In an exemplary embodiment of the present specification, M is Zn, and n is 0.

In an exemplary embodiment of the present specification, M is Al, In, or Ga, and n is 1.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring. In another embodiment, “substituted or unsubstituted” refers to a halogen group; an alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; and a heteroaryl group having 2 to 20 carbon atoms or having no substituent.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; halogen group; An alkyl group having 1 to 5 carbon atoms; An aryl group with 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 13 carbon atoms; A heteroaryl group having 6 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 13 carbon atoms; or an amine group substituted or unsubstituted with an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 13 carbon atoms, or a ring in which adjacent substituents are combined with each other to form a substituted or unsubstituted ring with an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 13 carbon atoms. forms.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; nitro group; halogen group; methyl group; ethyl group; profiler; isopropyl group; butyl group; sec-butyl group; tert-butyl group; phenyl group; Biphenyl group; naphthyl group; fluorenyl group; carbazole group; phenylcarbazole group; Dibenzofuran group; Dibenzothiophene group; dimethylamine group; diethylamine group; di-tert-butylamine group; Or it is a diphenylamine group.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently hydrogen; halogen group; tert-butyl group; Or it is a diethylamine group.

In one embodiment of the present specification, A1 is a halogen group.

In one embodiment of the present specification, A2 is hydrogen.

In one embodiment of the present specification, A3 is a tert-butyl group; Or it is a diethylamine group.

In one embodiment of the present specification, A1 to A3 are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, A1 to A3 are combined with each other to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, A1 to A3 are combined with each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, the two A1 are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the two A1 are combined with each other to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, the two A1 are combined with each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, the two A2 are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the two A2 are combined with each other to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, the two A2 are combined with each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, the two A3 are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the two A3 are combined with each other to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, the two A3 are combined with each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, R and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 8 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

In an exemplary embodiment of the present specification, R and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; profiler; t-butyl group; phenyl group; naphthyl group; Biphenyl group; fluorenyl group; Or it is a dimethylfluorenyl group.

In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and are each independently an ethyl group; Or it is a phenyl group.

In an exemplary embodiment of the present specification, R and R' are ethyl groups.

In one embodiment of the present specification, R and R' are the same.

In one embodiment of the present specification, a is an integer from 0 to 4, and when it is 2 or more, A1 is the same as or different from each other.

In one embodiment of the present specification, b is an integer from 0 to 8, and when it is 2 or more, A2 is the same or different from each other.

In one embodiment of the present specification, c is an integer from 0 to 4, and when it is 2 or more, A3 is the same or different from each other.

In one embodiment of the present specification, a is 0, 1, or 2.

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

In one embodiment of the present specification, b is 0, 1, or 2.

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

In one embodiment of the present specification, c is 0, 1, or 2.

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

According to another embodiment of the present specification, Formula 1 may be expressed as Formula 2 below.

[Formula 2]

In Formula 2,

The definitions of M, X, n, A2, A3, b and c are as defined in Formula 1,

A11 is hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a11 is an integer from 0 to 6, and when it is 2 or more, A11 is the same as or different from each other.

In one embodiment of the present specification, A11 is hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, A11 is hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, A11 is hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, A11 is hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring. In another embodiment, “substituted or unsubstituted” refers to a halogen group; an alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; and a heteroaryl group having 2 to 20 carbon atoms or having no substituent.

In one embodiment of the present specification, A11 is hydrogen; heavy hydrogen; nitro group; halogen group; An alkyl group having 1 to 5 carbon atoms; An aryl group with 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 13 carbon atoms; A heteroaryl group having 6 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 13 carbon atoms; or an amine group substituted or unsubstituted with an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 13 carbon atoms, or a ring in which adjacent substituents are combined with each other to form a substituted or unsubstituted ring with an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 13 carbon atoms. forms.

In one embodiment of the present specification, A11 is hydrogen; nitro group; halogen group; methyl group; ethyl group; profiler; isopropyl group; butyl group; sec-butyl group; tert-butyl group; phenyl group; Biphenyl group; naphthyl group; fluorenyl group; carbazole group; phenylcarbazole group; Dibenzofuran group; Dibenzothiophene group; dimethylamine group; diethylamine group; di-tert-butylamine group; Or it is a diphenylamine group.

In one embodiment of the present specification, A11 is hydrogen; halogen group; tert-butyl group; Or it is a diethylamine group.

In one embodiment of the present specification, A11 is a halogen group.

According to another embodiment of the present specification, Formula 2 may be represented by any one of the following Formulas 2-1 to 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3,

The definitions of M, X, n, A11, A3, a11 and c are as defined in Formula 2,

A5 to A8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, A5 to A8 are the same as the definition of A2.

According to another embodiment of the present specification, Formula 2 may be represented by the following Formulas 3-1 to 3-3.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Formulas 3-1 to 3-3,

The definitions of M, X, n, A11, A2, A3, a11, b and c are as defined in Formula 2.

According to another embodiment of the present specification, Formula 2 may be represented by any one of the following Formulas 4-1 to 4-4.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

In Formulas 4-1 to 4-4,

The definitions of M, X, n, A11, A2, a11 and b are as defined in Formula 2,

B1 to B5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, B1 to B5 are the same as the definition of A3.

According to another embodiment of the present specification, Formula 1 may be represented by any one of the following Formulas 5-1 to 5-4.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

In Formulas 5-1 to 5-4,

The definitions of M, A2, X, n and b are as defined in Formula 1,

B11 to B14 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

In Formula 5-3, B11 and B13 are different from each other.

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

Additionally, according to an exemplary embodiment of the present specification, a colorant composition containing the above compound is provided.

The colorant composition may further include at least one type of dye and pigment in addition to the compound of Formula 1. For example, the colorant composition may include only the compound of Formula 1, but may also include the compound of Formula 1 and one or more dyes, the compound of Formula 1 and one or more pigments, or the compound of Formula 1 , it may contain one or more dyes and one or more pigments.

According to an exemplary embodiment of the present specification, a photosensitive resin composition containing the colorant composition can be provided.

According to an exemplary embodiment of the present specification, the photosensitive resin composition includes a colorant composition containing a compound represented by Formula 1; binder resin; multifunctional monomer; and a photoinitiator.

According to an exemplary embodiment of the present specification, the photosensitive resin composition includes a colorant composition containing a compound represented by Formula 1; binder resin; multifunctional monomer; photoinitiator; and a solvent.

According to an exemplary embodiment of the present specification, the photosensitive resin composition further includes a solvent.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film manufactured from the resin composition.

The binder resin may be a copolymer resin of a multifunctional monomer that provides mechanical strength and a monomer that provides alkali solubility, and may further include a binder commonly used in the art.

Polyfunctional monomers that provide mechanical strength to the membrane include unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, isobutyl ( Meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydroperpril (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, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth)acrylate ) 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 ) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only these It is not limited.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, 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 to these.

Specific examples of the unsaturated imides include N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It may be possible, but it is not limited to these.

The acid anhydrides include maleic anhydride, methyl maleic anhydride, and tetrahydrophthalic anhydride, but are not limited to these.

The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group, for example, (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, and ω-carboxy polycaprolactone mono(meth)acrylate. It is preferable to use more than one type, but it is not limited to these.

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

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

The weight average molecular weight is one of the average molecular weights used as a standard for the molecular weight of certain polymer materials whose molecular weight is not uniform, and is a value obtained by averaging the molecular weights of the component molecular species of a polymer compound with a molecular weight distribution by weight fraction.

The weight average molecular weight can be measured through Gel Permeation Chromatography (GPC) analysis.

According to an exemplary embodiment of the present specification, the binder resin is a copolymer of an unsaturated carboxylic acid ester and a monomer containing an acid group.

According to an exemplary embodiment of the present specification, the binder resin is a copolymer of benzyl methacrylate and methacrylic acid.

The multifunctional monomer is a monomer that serves to form a photoresist image by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, and neopentyl glycol di. Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate It may be a species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that triggers crosslinking by generating radicals with light, but for example, it is selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. There may be one or more types.

The acetophenone-based compound is 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, benzoinmethyl ether, benzoinethyl ether, benzoinisobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, etc., but is not limited thereto.

The biimidazole-based compounds include 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 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, etc. , but is not limited to this.

The triazine-based compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionate, ethyl-2-{4-[2,4 -bis(trichloromethyl)-s-triazin-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-triazin-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazin-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-triazin-6-yl]phenylthio}propionamide, 2,4-bis(trichloromethyl) Methyl)-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, etc., but is not limited thereto.

The oxime-based compounds include 1,2-octadione, -1-(4-phenylthio)phenyl, -2-(o-benzoyloxime) (CibaGeigy, SI 124), ethanone, -1-(9) -Ethyl)-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime) (CGI 242), N-1919 (Adeka), etc., but are not limited thereto.

The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether. , Propylene glycol diethyl ether, Diethylene glycol dimethyl ether, Diethylene glycol diethyl ether, Diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy It may be one or more selected from the group consisting of propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is not limited thereto.

According to an exemplary embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the compound represented by Formula 1 is 1% by weight to 60% by weight, and the content of the binder resin is 1% by weight. to 80 wt%, the photoinitiator content is 0.1 wt% to 20 wt%, and the polyfunctional monomer content is 0.1 wt% to 50 wt%.

According to an exemplary embodiment of the present specification, based on 100 parts by weight of the total weight of solids in the photosensitive resin composition, the content of the compound represented by Formula 1 is 1% by weight to 60% by weight; 3% to 30% by weight; 5% to 20% by weight; or 6% to 10% by weight.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. Solid content and weight percent based on the solid content of each component can be measured by general analysis methods used in the industry, such as liquid chromatography or gas chromatography.

According to one embodiment of the present specification. The photosensitive resin composition may further include a surfactant.

According to an exemplary embodiment of the present specification, the photosensitive resin composition is 1 or 2 selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an antioxidant, an ultraviolet absorber, a dispersant, and a leveling agent. It additionally contains the above additives.

According to an exemplary 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 solids in the photosensitive resin composition.

The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, and methyl-o-benzoyl. Benzophenone-based compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; florenone-based compounds such as 9-florenone, 2-chloro-9-florenone, and 2-methyl-9-florenone; Thioxanthone series such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; xanthone-based compounds such as xanthone and 2-methylxanthone; Anthraquinone-based compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. acridine-based compounds; dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; Benzoate-based compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- Amino synergists such as methyl-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-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo Coumarin-based compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidbenzalacetophenone; One or more types selected from the group consisting of 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, may be used.

The curing accelerator is used to increase curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2,5-dimercapto-1,3. , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), penta Erythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate), and trimethylolpropane-tris(3-mercaptopropio nate) can be used.

Adhesion accelerators used in this specification include methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, and methacryloyloxy propyldimethoxy silane. One or more types of methacryloyl silane coupling agents may be selected and used, and as alkyl trimethoxy silane, one or more types from octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. You can select and use it.

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-301, BYK-302, BYK-306, BYK-307 manufactured by BYK-Chemie. , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used, and the fluorine-based surfactant is DIC. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-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 not limited to these.

The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio-based antioxidants, and phosphine-based antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid-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-hydroxy Benzyl) 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'-tert-butylphenyl)butanoic acid] glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol Hindered phenol-based primary antioxidants such as ester); Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine. Systemic secondary antioxidants; Thio acids such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane. Systemic secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-Biphenyl)-4,4'-diylbisphosphonoic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl]ester ((1,1'-Biphenyl)-4,4' -Phosphite secondary antioxidants such as diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester) can be mentioned.

The ultraviolet absorber may be 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc., but is not limited thereto and may be used in the art. All commonly used ones can be used.

The thermal polymerization inhibitors include, for example, p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine. Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- It may include, but is not limited to, one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, and is not limited to these. It may include things that are generally known in the field.

The dispersant can be used by adding it internally to the pigment in the form of surface treatment of the pigment in advance, or by externally adding it to the pigment. The dispersant may be a compound type, nonionic, anionic, or cationic dispersant, and includes fluorine-based, ester-based, cationic, anionic, nonionic, and amphoteric surfactants. These may be used individually or in combination of two or more types.

Specifically, the dispersant is polyalkylene glycol and its esters, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, carboxylic acid salt, There is at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but it is not limited thereto.

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

According to an exemplary embodiment of the present specification, a photosensitive material manufactured including the photosensitive resin composition or a cured product thereof is provided.

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

The application method is not particularly limited, but spray method, roll coating method, spin coating method, etc. can be used, and spin coating method is generally widely used. Additionally, after forming the coating film, in some cases, some residual solvent may be removed under reduced pressure.

Light sources for curing the resin composition according to the present specification include, for example, a mercury vapor arc, carbon arc, and Xe arc that emit light with a wavelength of 250 nm to 450 nm, but are not necessarily limited thereto.

The resin composition according to the present specification is a pigment-dispersed photoresist for manufacturing a color filter for a thin film transistor liquid crystal display (TFT LCD), a photoresist for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode, It can be used in photosensitive materials for overcoat layer formation, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, photosensitive materials for printed wiring boards, and photosensitive materials for plasma display panels (PDP), etc., but its uses are limited. There is no special mention.

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

The color filter may be manufactured using a resin composition containing the compound represented by Chemical Formula 1. A color filter can be formed by applying the photosensitive resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.

The resin composition according to an exemplary embodiment of the present specification has excellent heat resistance, has little color change due to heat treatment, and can provide a color filter with high color gamut and excellent sensitivity even through a curing process when manufacturing the color filter.

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

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

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

A grid-like black pattern called a black matrix may be placed between the color pixels of the color filter for the purpose of improving contrast. Chrome can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching can be used. However, considering the high cost of the process, the high reflectivity of chrome, and environmental pollution caused by chrome waste liquid, a resin black matrix using a pigment dispersion method that allows microprocessing can be used.

The black matrix according to an exemplary embodiment of the present specification may use black pigment or black dye as a colorant. For example, carbon black can be used alone or a mixture of carbon black and a coloring pigment can be used. In this case, since a coloring pigment with poor light blocking properties is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of coloring material is relatively increased. There is an advantage to not doing this.

According to an exemplary embodiment of the present specification, a display device including the color filter is provided.

The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be either a liquid crystal display (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) or a cathode ray tube (CRT).

Hereinafter, in order to explain the present specification in detail, examples will be given in detail. However, the embodiments according to the present specification may be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present specification to those with average knowledge in the art.

<Manufacturing example>

Preparation Example 1: Synthesis of Compound A

1. Synthesis of Compound A-1

Cyclohexane-1,2-diamine (5.0 g, 43.8 mmol) was dissolved in ethanol (30 ml) and stirred at room temperature for 10 minutes. 2-Hydroxy-1-naphtaldehyde (7.5 g, 43.8 mmol) was dissolved in ethanol (50 ml), then slowly added dropwise and stirred at room temperature for 4 hours. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, added to distilled water (30 ml), stirred at room temperature for 30 minutes, and then filtered. The filtrate was dried to obtain compound A-1 (10.1g, 86%): MS [M]=268.16

2. Synthesis of Compound A

Compound A-1 (5 g, 18.65 mmol) was dissolved in ethanol (100 ml), then zinc acetate dihydrate (4.5 g, 20.5 mmol) and salicylaldehyde (2.5 g, 20.5 mmol) were added and incubated at about 60°C for 6 hours. It was stirred. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was added to distilled water (40ml) and stirred for 30 minutes. This was filtered again and dried to obtain Compound A (7.04 g, 87%): MS [M] = 434.1

Preparation Example 2: Synthesis of Compound B

1. Synthesis of Compound B-1

5-Bromo-2-hydroxybenzaldehyde (10 g, 50.0 mmol), phenylboronic acid (7.33 g, 60.0 mmol) and Pd(t-Bu ₃ P) ₂ (0.102 g, 0.2 mmol) were dissolved in 2M K ₂ It was added to CO ₃ aqueous solution (60 mL) and tetrahydrofuran (THF) (200 mL), and refluxed and stirred for about 4 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried with magnesium sulfate, distilled under reduced pressure, and recrystallized from ethyl acetate/hexane to obtain compound B-1 (7.03 g, 71%).: MS [ M] = 198.07

2. Synthesis of Compound B

Compound B-1 (5 g, 25.24 mmol) and Compound A-1 (7.1 g, 26.5 mmol) were dissolved in ethanol (100 ml), then gallium(III) nitrate hydrate (6.78 g, 26.5 mmol) was added and the mixture was stirred for about 60 minutes. It was stirred at ℃ for 6 hours. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was added to distilled water (40ml) and stirred for 30 minutes. This was filtered again and dried to obtain compound B (11.2 g, 77%): MS [M] = 577.1

Preparation Example 3: Synthesis of Compound C

Compound A-1 (5.0 g, 18.6 mmol) with 3,5-di-tert-butyl-2-hydroxybenzaldehyde (4.8 g, 20.5 mmol) and cobalt(II) acetate tetrahydrate (5.1 g, 20.5 mmol) was dissolved in ethanol (100 ml) and stirred at about 60°C for 6 hours. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, added to distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered. The filtrate was dried to obtain compound C (8.5 g, 84%): MS [M]=541.23

Preparation Example 4: Synthesis of Compound D

Compound A-1 (5.0 g, 18.6 mmol), 4-diethylamino-2-hydroxybenzaldehyde (3.96 g, 20.5 mmol) and manganese(II) acetate tetrahydrate (5.0 g, 20.5 mmol) were dissolved in ethanol (100 g). ml) and stirred at about 60°C for 6 hours. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, added to distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered. The filtrate was dried to obtain compound D (7.3 g, 79%): MS [M]=496.2

<Preparation of composition>

Example 1

Color material composition containing 3.000g of Compound A, 29.480g of binder resin, 2.000g of photoinitiator (Igacure-369), 7.370g of multifunctional monomer (photopolymerizable compound, DPHA (Japanese Explosives)), solvent (propylene glycol monomethyl ether acetate) A photosensitive resin composition was prepared by mixing 17.650 g of (PGMEA), 40.000 g of DMF (dimethylformamide), and 1.016 g of an additive (surfactant, DIC F-475).

The binder resin is a copolymer of benzyl methacrylate and methacrylic acid, the molar ratio of benzyl methacrylate and methacrylic acid is 70:30, and the acid value is 80 KOH mg/g. The weight average molecular weight measured by GPC is 12,000 g/mol, and the molecular weight distribution (PDI) is 2.0g. The solvent propylene glycol monomethyl ether acetate (PGMEA) was used at a solid content (S.C) of 25 parts by weight.

Examples 2 to 4

A photosensitive resin composition was prepared in the same manner as Example 1, except that Compounds B to D were used instead of Compound A in Example 1.

Comparative example

A photosensitive resin composition was prepared in the same manner as Example 1, except that Compound K1 below was used instead of Compound A in Example 1.

<Experimental example>

Substrate fabrication

The photosensitive resin compositions of Examples 1 to 4 and Comparative Examples were used to manufacture substrates, respectively. Specifically, the photosensitive resin compositions of Examples 1 to 4 and Comparative Examples were spin coated on glass (5 .

The distance between the substrate on which the film was formed and the photo mask was set to 300 μm, and an exposure dose of 40 mJ/cm ² was irradiated to the entire surface of the substrate using an exposure machine. The photomask is made of Quartz material.

Afterwards, the exposed substrate was developed in a developer (KOH, 0.05%) for 60 seconds, and the exposed substrate was postbake (PB) at 230°C for 20 minutes.

Minimum pattern length evaluation

The fine patterns formed in Comparative Examples and Examples 1 to 4 were measured using an optical microscope (X20) and are shown in Figures 1 to 5. Figure 1 shows fine pattern images of Comparative Examples, and Figures 2 to 5 show fine pattern images of Examples 1 to 4.

The minimum lengths of the fine patterns formed in Comparative Examples and Examples 1 to 4 were measured and shown in Table 1 below. The smaller the minimum length of the fine pattern, the better the sensitivity and adhesion.

Minimum pattern length (μm) Comparative example 8 Example 1 5 Example 2 6 Example 3 7 Example 4 6

Compound K1 used in the comparative example has a symmetrical ring structure with respect to the center line passing through cobalt in the parent core structure. On the other hand, in Examples 1 to 4 containing the compound of Formula 1, the ring structure is not symmetrical with respect to the center line passing through the metal of the parent core structure. In particular, the polycyclic aromatic ring terminals are a benzene ring and a naphthalene ring. Examples 1 to 4 have a smaller minimum pattern length than the comparative example.

Therefore, it can be seen that the colorant composition of the present invention has good sensitivity and adhesion when used as a colorant for a color filter.

Solubility evaluation

The solubility of the compositions prepared in Comparative Examples and Examples 1 to 4 was measured based on propylene glycol methyl ether acetate (PGMEA), and the results are shown in Table 2 below.

Solubility (%) Comparative example 0.7 Example 1 2.1 Example 2 1.1 Example 3 4.7 Example 4 3.9

Looking at Table 2, the solubility values of Examples 1 to 4, in which the compound represented by Chemical Formula 1 was applied to the coloring material for a color filter, are greater than or equal to the solubility values of the comparative examples used in the art. In particular, the solubility values of Examples 3 and 4 using colorant compositions containing compounds C and D were very high.

Therefore, it can be seen that the colorant composition of the present invention has excellent solubility in solvents. The colorant composition of the present invention can be used as a soluble colorant, that is, a dye, and can be used with an insoluble colorant, allowing various colors to be expressed as a display colorant.

Claims (14)

A colorant composition comprising a compound represented by the following formula (1):
[Formula 1]

In Formula 1,
M is a transition metal or post-transition metal,
X is Cl; Br; Nitrile group; O(C=O)CH ₃ ; ONO ₂ ; or OSO ₂ ,
n is 0 or 1,
A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
a is an integer from 0 to 4, and when it is 2 or more, A1 is the same or different from each other,
b is an integer from 0 to 8, and when it is 2 or more, A2 is the same or different from each other,
c is an integer from 0 to 4, and when it is 2 or more, A3 is the same or different from each other,
R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
In the compound represented by Formula 1, the left and right substituents form an asymmetric structure with respect to the symmetry axis passing through M and X. The colorant composition according to claim 1, wherein Formula 1 is represented by Formula 2:
[Formula 2]

In Formula 2,
The definitions of M, X, n, A2, A3, b and c are as defined in Formula 1,
A11 is hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a11 is an integer from 0 to 6, and when it is 2 or more, A11 is the same as or different from each other. The colorant composition according to claim 2, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 3-1 to 3-3:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Formulas 3-1 to 3-3,
The definitions of M, X, n, A11, A2, A3, a11, b and c are as defined in Formula 2. The colorant composition according to claim 2, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 4-1 to 4-4:
[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

In Formulas 4-1 to 4-4,
The definitions of M, X, n, A11, A2, a11 and b are as defined in Formula 2,
B1 to B5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted haloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. In claim 1,
A1 to A3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; nitro group; Nitrile group; halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or NRR', or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
R and R' are the same or different from each other and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a colorant composition that is a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms. In claim 1,
X is Cl; Br; O(C=O)CH ₃ ; Or a colorant composition that is ONO ₂ . In claim 1,
A colorant composition where M is Zn, Co, Cu, Fe, Mn, Cr, Al, In or Ga. The colorant composition according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following compounds:



. The colorant composition of any one of claims 1 to 8; binder resin; multifunctional monomer; And a photosensitive resin composition comprising a photoinitiator. The method of claim 9, wherein the content of the compound represented by Formula 1 is 1% by weight to 60% by weight based on the total weight of solids in the photosensitive resin composition,
The content of the binder resin is 1% by weight to 80% by weight,
The content of the photoinitiator is 0.1% by weight to 20% by weight,
A photosensitive resin composition wherein the content of the multifunctional monomer is 0.1% by weight to 50% by weight. The photosensitive resin composition of claim 9, further comprising a solvent. A photosensitive material comprising the photosensitive resin composition or a cured product thereof according to claim 9. A color filter comprising the photosensitive material according to claim 12. A display device including a color filter according to claim 13.