KR100377642B1 - Triazine-based photoinitators comprising heteroaromatic groups - Google Patents

Abstract

The present invention relates to a photosensitive composition. In particular, the present invention relates to a triazine-based compound containing a novel heteroaromatic group which is contained in the photosensitive composition and has excellent long-term storage at room temperature and excellent effect as a photopolymerization initiator.

The present invention provides a triazine compound represented by the following formula (1), a photoinitiator using the compound as an active ingredient, and a photosensitive composition using the same.

[Formula 1]

In the above formula,

R ₁ , R ₂ , R ₃ are each independently hydrogen, halogen, alkyl of 1 to 6 carbon atoms,

Or an alkoxyl group having 1 to 6 carbon atoms,

X is S or NR ₄ ,

Where R ₄ is

C _n H _{2n + 1} (n is an integer from 0 to 12),

C _n H _2n COOC _m H _{2m + 1} (n, m are each independently an integer of 1 to 12),

(CH ₂ ) _n COOC _m H _{2 m} OC _L H _{2L + 1} (n, m, L are each independently an integer of 1 to 12),

(CH ₂ ) _n COO-cyclo-C _m H _2m-1 (n is an integer from 1 to 12, m is an integer from 3 to 12),

(CH ₂ ) _n O (C ₂ H ₄ O) _m C _ℓ H _{2ℓ + 1} (n, ℓ are each independently an integer of 1-12, m is

Integer from 0 to 4),

C _n H _2n OR _f (n is an integer from 1 to 12, R _f is phenyl, thiophenyl, furanyl,

benzyl, ο-cresolyl, m-cresolyl or p-cresolyl)

It is selected from the group consisting of.

Description

Triazine compound and photoinitiator including heteroaromatic group {TRIAZINE-BASED PHOTOINITATORS COMPRISING HETEROAROMATIC GROUPS}

[Industrial use]

The present invention relates to a photosensitive composition. In particular, it is related with the triazine type compound containing the novel hetero aromatic group which is contained in the photosensitive composition, is excellent in long-term storage at room temperature, and excellent in an effect as a photoinitiator.

[Prior art]

The photosensitive composition includes a photopolymerization initiator in a polymerizable compound having an ethylenically unsaturated bond, and the photosensitive composition can be polymerized and cured by being irradiated with light, so that photocurable inks, photosensitive printing plates, various photoresists and LCDs are provided. It is used for color filters.

Acetophenone derivatives, benzophenone derivatives, acyl phosphine oxide derivatives, and triazine derivatives are known as photopolymerization initiators used in such photosensitive compositions. Halomethyl triazine compounds which are decomposed by irradiation to generate halogen radicals are frequently used. Among the halomethyl triazine compounds, 2-aryl-4,6-bis (trihalomethyl) -s-triazine (2-aryl-4,6-bis (tri halomethyl) -s-triazine) has relatively high sensitivity. It is known to be excellent.

For example, Japanese Patent Application Laid-open No. 53-133428 proposes to use a compound using a bicyclic or polycyclic aromatic group or a heterocyclic aromatic group as an aryl group in 2-position, and among them, naphtha as aryl group. It is described that good results are obtained when a naphthyl group is used. However, the sensitivity of this compound is not satisfactory in practical use, it must be used in large quantities or requires long-term light irradiation, and its solubility in a polymerizable compound having an ethylenically unsaturated bond is insufficient, resulting in low stability over time of the photosensitive composition. There are disadvantages.

In addition, Japanese Patent Application Laid-Open No. 63-70243 discloses a method of improving stability over time of a photosensitive composition by introducing a substituent having an amide bond or an ester bond to a 2-position naphthyl group in the compound. Is proposed. However, this case is also not satisfactory in the sensitivity as a photoinitiator, and the photoinitiator having a small molecular weight and high crystallinity has a disadvantage in that the photoinitiator is released after coating or crystallized in the film to decrease the photoinitiation efficiency.

As a method for solving the problems of the compounds, a method of using an initiator having a strong interaction with a binder, a method of using a photoinitiator having a large molecular weight, and a multi-functional or polyfunctional triazine system Methods of using photoinitiators are known.

In connection with this process, US Pat. No. 5,298,361 describes photoinitiators having two or more photoactive triazine groups. Triazine groups here are linked by aliphatic ethers, urethanes, esters, amide bonds.

Therefore, in view of the problems of the conventional photoinitiator triazine in which a hetero aromatic group (hetero aromatic group) is introduced at the 2-aryl position in the 2-aryl-4,6-bis (trihalomethyl) -s-triazine-based compound ( It is an object to provide a triazine) photoinitiator.

Another object of the present invention is to provide a compound which is included in the photosensitive composition and has excellent long-term storage at room temperature, excellent effect of a photopolymerization initiator, excellent control of development time, and excellent coating property.

1 is a UV spectrum showing the UV-vis spectrum and photobleaching effect of the compound represented by Formula 1 prepared in Example 1.

FIG. 2 is a UV spectrum showing a UV-vis spectrum and a photobleaching effect of the compound represented by Chemical Formula 1b prepared in Example 2. FIG.

[Means for solving the problem]

The present invention provides a triazine compound having a heteroaromatic group introduced at the 2-position represented by the following formula (1) and a photopolymerization initiator containing the compound as an active ingredient in order to achieve the above object.

[Formula 1]

In the above formula,

R ₁ , R ₂ , R ₃ are each independently hydrogen, halogen, alkyl of 1 to 6 carbon atoms,

Or an alkoxyl group having 1 to 6 carbon atoms,

X is S or NR ₄ ,

Where R ₄ is

C _n H _{2n + 1} (n is an integer from 0 to 12),

C _n H _2n COOC _m H _{2m + 1} (n, m are each independently an integer of 1 to 12),

(CH ₂ ) _n COOC _m H _{2 m} OC _L H _{2L + 1} (n, m, L are each independently an integer of 1 to 12),

(CH ₂ ) _n COO-cyclo-C _m H _2m-1 (n is an integer from 1 to 12, m is an integer from 3 to 12),

(CH ₂ ) _n O (C ₂ H ₄ O) _m C _ℓ H _{2ℓ + 1} (n, ℓ are each independently an integer of 1-12, m is

Integer from 0 to 4),

C _n H _2n OR _f (n is an integer from 1 to 12, R _f is phenyl, thiophenyl, furanyl,

benzyl, ο-cresolyl, m-cresolyl or p-cresolyl)

It is selected from the group consisting of.

In order to achieve the above object, difunctional halomethyl triazine compounds having a heteroaromatic group introduced at 2-position have excellent long-term storage at room temperature, and can adjust the absorption wavelength region according to the introduced heteroaromatic group. There is a photobleaching effect, and the effect as a photopolymerization initiator is great without affecting the color of the color filter photoresist for LCD.

The present invention for the above purpose is described in more detail below.

In the compound represented by Formula 1,

When X is NR ₄ , when R ₄ is C _n H _{2n + 1} , hydrogen is an alkyl group having 1 to 12 carbon atoms as methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, hexyl, heptyl, octyl , 2-ethylhexyl, isooctyl, nonyl, decanyl, undecanyl, dodecanyl.

When R ₄ is C _n H _2n COOC _m H _{2m + 1} , C _n H _2n is an alkyl group having 1 to 12 carbon atoms and is methylene, ethylene, 1,2-propylene, 1,3-propylene, 1,4-butyl Ethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, and C _m H _{2m + 1} is methyl as an alkyl group having 1 to 12 carbon atoms. , Ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, decanyl, undecanyl, dodecanyl.

When R ₄ is (CH ₂ ) _n COOC _m H _{2 m} OC _L H _{2L + 1} , (CH ₂ ) _n is an alkyl group having 1 to 12 carbon atoms, and is methylene, ethylene, 1,2-propylene, 1,3-propylene. , 1,4-butylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, C _m H _2m has 1 to 12 carbon atoms As alkyl groups of methylene, ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodeca It is selected from the group consisting of methylene, C ₁ H _{2 L + 1} is an alkyl group having 1 to 12 carbon atoms, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl, heptyl, octyl, 2- Ethylhexyl, isooctyl, nonyl, decanyl, undecanyl, dodecanyl.

When R ₄ is (CH ₂ ) _n COO-cyclo-C _m H _2m-1 , (CH ₂ ) _n is an alkyl group having 1 to 12 carbon atoms and is methylene, ethylene, 1,2-propylene, 1,3-propylene , 1,4-butylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, cyclo-C _m H _2m-1 is cyclo It is a C3-C12 alicyclic group containing a group.

When R ₄ is (CH ₂ ) _n O (C ₂ H ₄ O) _m C _L H _{2L + 1} , (CH ₂ ) _n is an alkyl group having 1 to 12 carbon atoms, such as methylene, ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, m is 0-4 C ₁ H _{2 L + 1} is an alkyl group having 1 to 12 carbon atoms and is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, iso Octyl, nonyl, decanyl, undecanyl, dodecanyl.

When R ₄ is C _n H _2n OR _f , C _n H _2n is an alkyl group having 1 to 12 carbon atoms and is methylene, ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, pentamethylene , Hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, R _f is phenyl, thiophenyl, furanyl, benzyl, ο-cresolyl, m-cresolyl, p -cresolyl is selected from the group consisting of.

Method for producing a triazine compound containing a heteroaromatic represented by the formula (1) of the present invention is a step of reacting a heteroaromatic compound containing a cyano group represented by the formula (2) with trichloroacetonitrile in the presence of aluminum bromide (AlBr ₃ ) It will be prepared to include.

[Formula 2]

In the above formula,

R ₁ , R ₂ , R ₃ are each independently hydrogen, halogen, alkyl of 1 to 6 carbon atoms,

Or an alkoxyl group having 1 to 6 carbon atoms,

X is S or NR ₄ ,

Where R ₄ is

C _n H _{2n + 1} (n is an integer from 0 to 12),

C _n H _2n COOC _m H _{2m + 1} (n, m are each independently an integer of 1 to 12),

(CH ₂ ) _n COOC _m H _{2 m} OC _L H _{2L + 1} (n, m, L are each independently an integer of 1 to 12),

(CH ₂ ) _n COO-cyclo-C _m H _2m-1 (n is an integer from 1 to 12, m is an integer from 3 to 12),

(CH ₂ ) _n O (C ₂ H ₄ O) _m C _ℓ H _{2ℓ + 1} (n, ℓ are each independently an integer of 1-12, m is

Integer from 0 to 4),

C _n H _2n OR _f (n is an integer from 1 to 12, R _f is phenyl, thiophenyl, furanyl,

benzyl, ο-cresolyl, m-cresolyl or p-cresolyl)

It is selected from the group consisting of.

The compound of the present invention is useful as a photopolymerization initiator of a polymerizable compound having an ethylenically unsaturated bond as described above, and a polymerizable compound having such an ethylenically unsaturated bond can be used in conventional photosensitive compositions.

Examples of the polymerizable compound having an ethylenically unsaturated bond include ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate having 2 to 14 ethylene groups, trimethylolpropanedi (meth) acrylate, and trimethyl All-propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, propylene glycol di (meth) acrylate and dipentaerythritol penta with 2 to 14 propylene groups Compounds obtained by esterifying polyhydric alcohols such as (meth) acrylate and dipentaerythritol hexa (meth) acrylate with α, β-unsaturated carboxylic acid; Compounds obtained by adding (meth) acrylic acid to glycidyl-containing compounds such as trimethylolpropane triglycidyl ether acrylic acid adduct and bisphenol A diglycidyl ether acrylic acid adduct; ester compounds of a compound having a hydroxyl group and an ethylenically unsaturated bond, such as a phthalic acid diester of β-hydroxyether (meth) acrylate, a toluene diisocyanate adduct of β-hydroxyethyl (meth) acrylate, or a polyhydric carboxylic acid, or Adducts with polyisocyanates; (Meth) acrylic acid alkyl esters, such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.

In addition, when the thermoplastic organic polymer is used together with the polymerizable compound having an ethylenically unsaturated bond, the properties of the cured product can be improved. Examples of this thermoplastic organic polymer include a copolymer of (meth) acrylic acid ester compound and (meth) acrylic acid, a (meth) acrylic acid ester compound, a copolymer of (meth) acrylic acid and other vinyl monomers copolymerizable with these, and the like. have.

As said (meth) acrylic acid ester compound, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, tetrahydro perfill (meth) acrylate, agent 3butyl (tachery) (meth) acrylate, glycidyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth ) Acrylate, benzyl (meth) acrylate). In addition, the vinyl monomers include styrene and vinyl toluene.

Synergistic effects can be expected when the compound of the present invention is used in combination with a conventional photopolymerization initiator. Examples of conventional photopolymerization initiators that can be used in combination with the compound of the present invention include benzophenone, phenylbiphenyl ketone, and 1-hydroxy-. 1-benzoylcyclohexane, benzyl, benzyldimethyl ketal, 1-benzyl-1-dimethylamino-1- (4'-morpholino-benzoyl) propane, 2-morpholinyl-2- (4'-methylmercapto) Benzoylpropane, thioxanthone, 1-chloro-4- hydroxy thioxanthone, isopropyl thioxanthone, diethyl thioxanthone, ethyl anthraquinone, 4-benzoyl-4'-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4'-isopropyl) benzoylpropane, 4-butylbenzoyltrichloromethane, 4-phenoxybenzoyldichloromethane, methyl benzoyl formate, 1,7 -Bis (9'-acridinyl) heptane, 9-n-butyl-3,6-bis (2'-morpholino-isobutyloyl) carbazole, 2-methyl-4,6-bis (trichloro Methyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6-bis (trichloromethyl) -s-triazine, 2 , 4,6-trimethylbenzoyldiphenylphosphine and the like.

The photosensitive composition containing the compound of the present invention may contain a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butyl catecol, phenothiazine, or the like as necessary. ; Plasticizers; Adhesion promoters; General additives such as fillers can be used.

The photosensitive composition containing the compound of this invention is used as a solution composition which added the polymerization initiator of the said compound of this invention, the polymeric compound which has an ethylenically unsaturated bond, and the solvent which melt | dissolves or disperse | distributes each component of a thermoplastic organic polymer as needed. .

Examples of the solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cersolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl Ether, propylene glycol diethyl 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, tert-butanol, cyclohexanone, propylene glycol methyl ether acetate, ethyl-3-ethoxypropionate, ethyl Cellosolve acetate, methyl cellosolve acetate, butyl acetate and the like.

The photosensitive composition containing the compound of the present invention is used by a method such as a roll coater, curtain coater, spin coater, various printing, deposition, etc., and supports such as metal, paper, and glass. Is applied to the phase. Moreover, it is also possible to apply | coat on a support body, such as a film, and to transfer on another support body, There is no restriction | limiting in the application method.

The photosensitive composition containing the compound of the present invention is a photocurable paint, a photocurable ink, a photocurable adhesive, a printing plate, a photoresist for a printed wiring board, a pigment dispersed photoresist for manufacturing a TFT LCD color filter, a black matrix, a PDP It can be used for the purpose and the like, there is no limitation on its use.

The light source used to cure the photosensitive composition containing the compound of the present invention may use light having a wavelength of 250 to 450 nm, and examples thereof include mercury vapor arc, carbon arc, xen arc, and the like. have.

The present invention will be described in more detail with reference to the following Examples and Comparative Examples, which are intended to illustrate the present invention, but the present invention is not limited thereto.

EXAMPLE

Example 1

Preparation of 5-methyl-2- (2,4-bis (trichloromethyl) -s-triazin-6-yl) thiophene represented by Formula 1a

[Formula 1a]

[Step 1: Preparation of 5-methyl-2-thiophenecabonitrile]

15 g (0.12 mol) of 5-methyl-2-thiophenecarboxaldehyde was dissolved in methanol, and a solution of 10 g of hydroxylamine hydrochloride in 13 ml of distilled water was slowly added thereto. Fever was observed here.

14 g of sodium hydroxide was dissolved in 10 ml of water, and slowly added to the reaction vessel, and left for several hours. Then, 50 g of crushed ice was added and the solution was saturated with dry ice to produce a pale yellow powder. More water saturated with carbon dioxide is added here to produce more powder.

The resulting powder was filtered, washed with distilled water and dried in vacuo to give an oxime of at least 95% yield.

The compound synthesized above was placed in a 250 ml flask, 80 ml of acetic anhydride was added, the reaction was carried out at a bath temperature of 140 ° C. for 5 hours, and poured into 250 g of crushed ice. The extracted organic layer was washed with distilled water to remove the dark red (dark red color) significantly.

The light brown oil component obtained after the removal of volatiles was structurally analyzed by NMR to obtain a pure product. Yield was 93% or higher.

[Step 2: Preparation of 5-methyl-2- (2,4-bis (trichloromethyl) -s-triazin-6-yl) thiophene]

7 g (73.1 mmol) of 5-methyl-2-thiophenecabonitrile prepared above, 0.6 g of ArBr _{3 and} 35 g of trichloroacetonitrile solution were bubbled with dry HCl at room temperature.

The reaction was confirmed by TLC over time, the reaction was terminated after 24 hours, extracted with 500 ml of chloroform, washed with ion-exchanged water (DI water) and dried over anhydrous magnesium sulfate.

The dried extract removed residual evaporation material in vacuo, and induced crystals in methanol to obtain a compound having a yield of 87% or more.

This compound is NMR, FT-IR, UV-vis. Analysis by spectrophotometer (spectrophotometer) confirmed the structure as shown in Table 1.

TABLE 1

¹ H NMR (CDCl ₃ , ppm) 8.22 (1H, d, Ar-H), 6.96 (1H, d, Ar-H), 2.60 (3H, s, -CH ₃ ) UV-vis. (Nm) λ _max = 346

Example 2

1,5-dimethyl-2- {2,4-bis (trichloromethyl) -s-triazin-6-yl} pyrrole prepared by Chemical Formula 1b

[Formula 1b]

7 g (58.3 mmol) of 1,5-dimethyl-2-pyrrolecarbonitrile, 0.7 g of ArBr _{3 and} 40 g of trichloroacetonitrile solution were bubbled with dry HCl at room temperature.

The reaction was confirmed by the TLC product over time, and when a solid precipitate was produced, the reaction was terminated, extracted with 400 ml of chloroform, washed with ion-exchanged water (DI water), and dried over anhydrous magnesium sulfate.

The dried extract removed residual evaporation material under vacuum, and induced crystals in methanol to obtain a compound having a yield of 63% or more.

This compound is NMR, FT-IR, UV-vis. Analysis by spectrophotometer (spectrophotometer) confirmed the structure as shown in Table 2.

TABLE 2

¹ H NMR (CDCl ₃ , ppm) 7.60 (1H, d, Ar-H), 6.11 (1H, d, Ar-H), 4.06 (3H, s, N-CH ₃ ), 2.34 (3H, s, -CH ₃ ) UV-vis. (Nm) λ _max = 357

Example 3

As shown in Table 3, the composition containing the compound represented by Formula 1a of Example 1 was placed in a bead mill and mixed and dispersed for 20 hours to prepare a photosensitive composition. Here, the size of the beads was 0.3 mm in diameter, and after milling, they were filtered through a 10 μm filter and stored in a UV-blocked room for about 10 days. .

This photosensitive composition solution was spin coated onto glass and prebaked at a temperature of 80-90 ° C. for 2 minutes to form a uniform film having a thickness of about 2 μm.

The film was exposed to an energy of 300 mJ / cm 2 under a high pressure mercury lamp using a photomask, the pattern was developed with an alkaline solution, washed with ion-exchanged water, followed by 60 minutes at 200 ° C. It was postbaked.

A clear pattern was formed when the film state of the glass surface was observed with the optical microscope.

TABLE 3

Raw material Raw material type Composition (part by weight) Fee C.I. pigment red 177 90 bookbinder BzMA: MAA: HEMA = 65: 25: 10 Mw: 40,000 50 Polymerizable compound dipentaerythritol hexaacrylate 40 Photopolymerization initiator 5-methyl-2- (2,4-bis (trichloromethyl) -s-triazin-6-yl) thiophene 30 Organic solvent PGMEA (b.p .: 146 ° C.) 790

Example 4

As shown in Table 4, after the compositions containing the compound represented by Formula 1a of Example 1 were prepared in the same manner as in Example 1, a clear pattern was formed by observing the film state of the glass surface with an optical microscope. there was.

TABLE 4

Raw material Raw material type Composition (part by weight) Fee C.I. pigment red 177 90 bookbinder BzMA: MAA = 75: 25Mw: 35,000 50 Polymerizable compound dipentaerythritol hexaacrylate 40 Photopolymerization initiator 5-methyl-2- (2,4-bis (trichloromethyl) -s-triazin-6-yl) thiophene 30 Organic solvent PGMEA (b.p .: 146 ° C.) 790

Example 5

To prepare a composition comprising the compound represented by the formula 1b of Example 2, as shown in Table 5 in the same manner as in Example 1 after observing the film state of the glass surface with an optical microscope it can be seen that a clear pattern was formed there was.

TABLE 5

Raw material Raw material type Composition (part by weight) Fee C.I. pigment red 177 90 bookbinder BzMA: MAA: HEMA = 65: 25: 10 Mw: 40,000 50 Polymerizable compound dipentaerythritol hexaacrylate 40 Photopolymerization initiator 1,5-dimethyl-2- {2,4-bis (trichloromethyl) -s-triazin-6-yl} pyrrole 30 Organic solvent PGMEA (b.p .: 146 ° C.) 790

Example 6

To prepare a composition comprising the compound represented by Formula 1a of Example 1, as shown in Table 6 in the same manner as in Example 1 and observed the film state of the glass surface with an optical microscope to see that a clear pattern was formed there was.

TABLE 6

Raw material Raw material type Composition (part by weight) Fee C.I. pigment red 177 90 bookbinder BzMA: MAA: HEMA = 65: 25: 10 Mw: 40,000 50 Polymerizable compound dipentaerythritol hexaacrylate 40 Photopolymerization initiator 5-methyl-2- (2,4-bis (trichloromethyl) -s-triazin-6-yl) thiophene 15 (±) 2-benzyl-2- (dimethylamino) -4'morpholinobutyrophenone (Aldrich) 15 Organic solvent PGMEA (b.p .: 146 ° C.) 790

Example 7

To prepare a composition comprising the compound represented by Formula 1b of Example 2, as shown in Table 7 in the same manner as in Example 1 and observed the film state of the glass surface with an optical microscope to see that a clear pattern was formed there was.

TABLE 7

Raw material Raw material type Composition (part by weight) Fee C.I. pigment red 177 90 Binda BzMA: MAA: HEMA = 65: 25: 10 Mw: 40,000 50 Polymerizable compound dipentaerythritol hexaacrylate 40 Photopolymerization initiator 1,5-dimethyl-2- {2,4-bis (trichloromethyl) -s-triazin-6-yl} pyrrole 15 (±) 2-benzyl-2- (dimethylamino) -4'morpholinobutyrophenone (Aldrich) 15 Organic solvent PGMEA (b.p .: 146 ° C.) 790

The halomethyl triazine compound containing the heteroaromatic group of the present invention has excellent long-term storage at room temperature, can adjust the absorption wavelength range according to the atoms to be bonded, and has a photobleaching effect. When used in the manufacture of color filters for LCD (color filter) is effective as a photopolymerization initiator without affecting the color of the color filter photoresist (color filter photoresist).

Claims (6)

Triazine compound containing a hetero aromatic represented by the formula (1): [Formula 1] In the above formula, R ₁ , R ₂ and R ₃ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, X is NR ₄ , Wherein R ₄ is C _n H _{2n + 1} (n is an integer from 1 to 6). delete The method of claim 1, Compound represented by the following formula (1b): [Formula 1b] In the method for producing a triazine compound containing a hetero aromatic represented by the formula (1), [Formula 1] In the above formula, R ₁ , R ₂ and R ₃ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, X is NR ₄ , Wherein R ₄ is C _n H _{2n + 1} (n is an integer from 1 to 6); A method comprising reacting a heteroaromatic compound comprising a cyano group represented by Formula 2 with trichloroacetonitrile in the presence of aluminum bromide (AlBr ₃ ): [Formula 2] In the above formula, R ₁ , R ₂ and R ₃ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms. X is NR ₄ , Wherein R ₄ is C _n H _{2n + 1} (n is an integer from 1 to 6). Benzophenone, phenylbiphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzyl, benzyldimethyl ketal, 1-benzyl-1-dimethylamino-1- (4'-morpholino-benzoyl) propane, 2- Morpholyl-2- (4'-methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4- hydroxythioxanthone, isopropyl thioxanthone, diethyl thioxanthone, ethyl anthraquinone, 4-benzoyl- 4'-methyldiphenylsulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4'-isopropyl) benzoylpropane, 4-butylbenzoyltrichloromethane, 4- Phenoxybenzoyldichloromethane, methyl benzoyl formate, 1,7-bis (9'-acridinyl) heptane, 9-n-butyl-3,6-bis (2'-morpholino-isobutyloyl) cover Sol, 2-Methyl-4,6-bis (trichloromethyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6 -Bis (trichloromethyl) -s-triazine and 2,4,6-trimethylbenzoyldiphenylphosphine To the photo-initiator is selected from the mixture containing the compound represented by the general formula (1) photo-polymerization initiator: [Formula 1] In the above formula, R ₁ , R ₂ and R ₃ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, X is NR ₄ , Wherein R ₄ is C _n H _{2n + 1} (n is an integer from 1 to 6). A photocurable coating composition comprising a triazine compound containing a heteroaromatic represented by Formula 1, a photocurable ink composition, a photocurable adhesive, a photosensitive printing plate, a photoresist composition for a printed circuit board, and a pigment dispersion type photo for manufacturing a TFT LCD color filter. Resist composition, photopolymerization composition for plasma display panel or photoresist composition for semiconductor manufacturing: [Formula 1] In the above formula, R ₁ , R ₂ and R ₃ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, X is NR ₄ , Wherein R ₄ is C _n H _{2n + 1} (n is an integer from 1 to 6).