WO2019054707A1 - Novel triazine derivative and photosensitive composition comprising same - Google Patents

Abstract

The present invention relates to a compound represented by any one of the following formula A to formula C, and a photosensitive composition comprising the same, wherein the structure of the compound represented by any one of formula A to formula C is as described in the detailed description of the invention.

Description

Novel triazine derivatives and photosensitive compositions containing them

The present invention relates to a novel triazine derivative and a photosensitive composition containing the same, and more particularly to a novel triazine derivative having a high refractive index after a photo-crosslinking process, excellent curability in a process of producing an optical material, A novel triazine derivative having excellent properties and a photosensitive composition containing the novel triazine derivative.

A liquid crystal display (LCD) includes an optical sheet including an optical pattern formed on a base film and a base film, and a light guide plate is disposed under the optical sheet, or another optical sheet is provided between the optical sheet and the light guide plate .

Here, the types of optical sheets include a reflector sheet, a diffuser sheet, a prism sheet, These optical sheets are used for the purpose of improving the brightness of the backlight unit.

The optical sheet increases the brightness of light emitted in such a manner that light emitted from the light guide plate of the backlight is refracted and transmitted to the screen after passing through the liquid crystal. In order to increase the brightness of the liquid crystal display device, the refractive index of the optical sheet such as prism and DBEF It should be high.

In particular, with the development of LCD panel manufacturing technology, there has been a demand for a thin and bright LCD display, and accordingly, various attempts have been made to increase the brightness of the backlight unit.

However, the conventional high-refraction monomers have a low refractive index and thus have limitations in realizing brightness enhancement effects. Further, even when the refractive index of the optical sheet is increased, yellowing occurs in the optical sheet.

On the other hand, as a conventional technique relating to high refractive index monomers, Korean Patent Registration No. 10-1692343 (2016.12.28) and Korean Patent Laid-Open Publication No. 10-2017-0013674 (2017.02.07) propose an acrylic monomer as a high refractive index monomer have.

However, in spite of the prior art including the above-mentioned prior arts, there is a demand for a high-refraction monomer material having a high transmittance and an excellent yellowing resistance characteristic and a high high-refraction property in order to improve the brightness of a liquid crystal display. The need for the development of new technologies is constantly being sought.

Accordingly, a first technical object of the present invention is to provide a novel triazine derivative compound which has high transmittance, excellent light-crosslinking property and yellowing resistance, and which can be used as a monomer in a photosensitive composition having high refractive index .

A second technical object of the present invention is to provide a photosensitive composition comprising the triazine derivative compound and an optical article obtained by polymerizing the same.

To this end, the present invention provides a compound represented by any one of the following formulas (A) to (C).

(A)

In the above formula (A)

Ra is any substituent selected from hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₆ alkyl group,

Wherein L1 is a single bond, O, S, or -N (-R5) -,

L2 is a single bond, O, S, or -N (-R6) -,

X 1 to X 3 are the same or different and independently of each other are a single bond, O, S, -N (-R 7) - or -O ((CH ₂ ) _m O) _n - n is an integer selected from 1 to 4, and at least two of X1 to X3 each represent -N (-R7) -, or two or more of X1 to X3 each independently represent - _{O ((CH 2) m O} ) n - each -N (-R7) in the case of selecting - and _{-O ((CH 2) m O} ) n - may be identical to or different from each other, and

Wherein R4 to R7 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₃₀ an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted C ₆ -C ₅₀ ring, each ring of A C ₃ -C ₃₀ cycloalkyl group, and a substituted or unsubstituted C ₇ -C ₂₄ arylalkyl group,

Wherein W1 is any one selected from an alkylene group of a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or unsubstituted C ₁ -C ₁₂ a,

Wherein W2 and W3 are the same or different and each independently represent a single bond, a substituted or unsubstituted C ₁ a C ₆ aryl group, a substituted or unsubstituted ring of -C ₃₀ alkylene group, a substituted or unsubstituted -C ₃₀ unsubstituted C ₂ -C ₃₀ of alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group, the substituted or unsubstituted C ₂ -C ₅₀ hetero arylene group, and any one is selected from a substituted or unsubstituted heterocycloalkyl group of C ₂ -C ₃₀ a,

Wherein Y1 and Y2 are the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or non-substituted of unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ of each ring C, respectively of ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl of the group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group , A substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted A C ₆ -C ₃₀ arylsilyl group, and a substituent group represented by the following structural formula 1 or 2,

[Structural formula 1] [Structural formula 2]

In the above Structural Formula 1 and Structural Formula 2,

Wherein Rb and Rc are each the same or different, and independently are any one selected from the group consisting of hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C ₆ with each other,

"- *" in the structural formulas 1 and 2 means a bonding site in which X2 or X3 in the above formula (A) is bonded,

[Chemical Formula B]

≪ RTI ID = 0.0 &

In the above formula (B)

Wherein Ar 1 is a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or unsubstituted C ₂ -C ₃₀ heteroarylene group, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, and the one which is C ₂ -C ₃₀ alkenylene group, selected from substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group of the,

L6 is any one selected from a single bond, O, S, -N (-R11) -,

L7 is any of a single bond, O, S, -N (-R12) -,

In the above formula (C)

Substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkyl group, substituted Or an unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, or a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group,

In the above formulas (B) to (C)

Wherein Rd is a substituent of any one selected from hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C _6,

Each of L3 to L5 is the same or different and independently selected from a single bond, O, S, or -N (-R9) -,

When two or more of L3 to L5 each represent -N (-R9) -, each of -N (-R9) is the same or different,

Wherein X4 to X7 are the same or different and each, independently of one another a single bond, O, S, -N (-R10 ) -, -O ((CH 2) m O) n - are optionally replaced with one selected from said m and n are the same or different and are each independently an integer selected from 1 to 4,

The at least two of the X4 to X7 -N (-R10) respectively select, or at least two of the X4 to X7 is _{n -O ((CH 2) m} O) , respectively - if the select on each - N (-R 10) - and -O ((CH ₂ ) _m O) _n - are the same or different,

Wherein R8 to R12 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or unsubstituted of C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ ring, each ring of the A C ₃ -C ₃₀ cycloalkyl group, and a substituted or unsubstituted C ₇ -C ₂₄ arylalkyl group,

W4 is any one selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, and a substituted or unsubstituted C ₁ -C ₁₂ alkylene group,

The W5 to W7 are the same or different and each independently represent a single bond, a substituted or unsubstituted C ₁ -C ₃₀ an alkyl group, an arylene group, a substituted or unsubstituted substituted or unsubstituted C ₆ -C ₃₀ unsubstituted C ₂ -C ₃₀ of alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group, the substituted or unsubstituted C ₂ -C ₅₀ hetero arylene group, and any one is selected from a substituted or unsubstituted heterocycloalkyl group of C ₂ -C ₃₀ a,

The Y3 to Y5 are the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or non-substituted of unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ of each ring C, respectively of ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl of the group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group , A substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted A C ₆ -C ₃₀ arylsilyl group, and a substituent group represented by the following structural formula 1 or 2:

[Structural formula 1] [Structural formula 2]

In the above Structural Formula 1 and Structural Formula 2,

Wherein Rb and Rc are each the same or different, and independently are any one selected from the group consisting of hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C ₆ with each other,

"- *" in the structural formulas 1 and 2 means a binding site in which X5 to X7 in the above-mentioned formula (B) or (C) are bonded,

Here, the above-mentioned [Chemical Formula A] to [Chemical Formula C] "substituted" in the "substituted or unsubstituted" in the heavy hydrogen, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group of C ₁ -C _24, C ₁ -C ₂₄ halogenated alkyl group, C ₂ -C ₂₄ alkenyl, C ₂ -C ₂₄ alkynyl group of, C ₁ - ₂₄ heterocyclic group in the alkyl group, C ₆ -C ₂₄ aryl, C ₇ -C ₂₄ aryl An alkyl group, a C ₂ -C ₂₄ heteroaryl group, a C ₂ -C ₂₄ heteroarylalkyl group, a C ₁ -C ₂₄ alkoxy group, a C ₁ -C ₂₄ alkylthioyl group , a C ₁ -C ₂₄ alkylamino group , A C ₆ -C ₂₄ arylamino group, a C ₁ -C ₂₄ heteroarylamino group, a C ₁ -C ₂₄ alkylsilyl group, a C ₆ -C ₂₄ arylsilyl group, a C ₆ -C ₂₄ aryloxy group, And an arylthionyl group having _{6 to 24} carbon atoms.

The present invention also provides a photosensitive composition comprising a compound represented by any one of the above-mentioned formulas (A) to (C) and an optical material or an optical article obtained by polymerizing the same.

The novel triazine derivative compounds represented by any one of the formulas (A) to (C) according to the present invention can be used in a photosensitive composition to provide a property of high refractive index after the photo-crosslinking step.

In particular, it is possible to provide a photosensitive composition having a high transmittance and an excellent yellowing resistance characteristic, and has a limit in realizing a luminance improvement effect due to a low refractive index according to the prior art, and can solve the problem of color change of the optical sheet due to yellowing (DBEF) film, a coating material for an organic light emitting device (OLED), an optical lens, and a multifocal lens, which can be applied to a prism sheet, a microlens, a coating material for an LCD, a DBEF (Dual Brightness Enhancement Film) There are advantages.

Hereinafter, the present invention will be described in more detail. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is well known and commonly used in the art.

Throughout this specification, when an element is referred to as " including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise.

The compound represented by any one of the above-mentioned formulas (A) to (C) according to the present invention contains 1 to 3 triazine structures and may contain N, O, S or a single bond to each carbon atom of the triazine A first connecting portion; A second connecting portion comprising a single bond, an alkylene group or an arylene group; And a third connecting portion having N, O, S, alkylene oxide, or a single bond, and having a double bond such as at least one acrylic acid derivative at the terminal, wherein, among three carbon atoms of triazine, A technical feature is that a nitrogen atom is bonded to at least one carbon atom and a terminal thereof has a double bond such as an acrylic acid derivative.

Here, when a photosensitive composition comprising a triazine compound represented by any one of the above-mentioned formulas (A) to (C) is used as a monomer, a high refractive index and high transmittance can be exhibited and excellent yellowing resistance can be exhibited.

In consideration of the range of the alkyl group or the aryl group in the "substituted or unsubstituted C ₁ -C ₂₀ alkyl group" or the "substituted or unsubstituted C ₆ -C ₅₀ aryl group" in the present invention , The carbon numbers of the C ₁ -C ₂₀ alkyl group and the C ₆ -C ₅₀ aryl group are each an alkyl moiety or an aryl moiety constituting the alkyl moiety or the aryl moiety when considered to be unsubstituted, Means the number of carbon atoms. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to a C ₆ aryl group substituted with a C ₄ butyl group.

The aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aromatic group such as a pyridyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle, a crycenyl, a naphthacenyl, a fluoranthene and the like, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH (R), -N (R ') (R''),R' and R "are independently from each other C ₁ -C ₁₀ an alkyl group, in which case the "alkyl group" hereinafter), an amidino group, a hydrazine group, a hydrazone jongi, a carboxyl group, a sulfonic acid group, phosphoric acid group, an alkyl group, a halogenated alkyl group of C ₁ -C ₂₄ in C ₁ -C _24, C ₂ -C ₂₄ alkenyl group, an arylalkyl group of C ₂ -C ₂₄ alkynyl group of, C ₁ -C ₂₄ heterocyclic group, C ₆ -C ₂₄ aryl group, C ₇ -C ₂₄ a, C ₂ -C ₂₄ A heteroaryl group of a heteroaryl group or C ₂ -C ₂₄ which may be substituted.

The heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 1, 2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Se and Te in the aryl group, Means a C ₂ -C ₂₄ ring aromatic system, which rings can be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl and hexyl. The hydrogen atoms of the above hydrogen atoms can be substituted with the same substituents as those in the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkylaryl group used as the substituent in the compound of the present invention include methylphenyl, dimethylphenyl, n -propylphenyl, t -butylphenyl, methylnaphthyl and the like, May be substituted with the same substituents as those in the aryl group.

Specific examples of the cycloalkyl group as the substituent used in the compound of the present invention include cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl and ethylcyclohexyl, and one of the cycloalkyl groups The above hydrogen atoms may be substituted with substituents similar to those in the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl. At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

On the other hand, to within the substituent R4 of the formula (A) in the present invention, R6 is preferably the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C of each other, respectively _And an aryl group having _{6 to 20} carbon atoms, and Ra, Rb and Rc are preferably the same or different, and independently of each other may be any substituent selected from hydrogen and a deuterated methyl group.

At least one of Y1 and Y2 in formula (A) may be a structural formula (1) or a structural formula (2). By having such a structure, both ends of a monomer have a double bond, and the photocatalytic rate can be controlled during photopolymerization.

L 1 in the formula (A) may be -N (-R 5) - or S, L 2 may be -N (-R 6) - or S, more preferably L 1 is -N (-R 5) L2 is a -N (-R6) -, and wherein R5 and R6 are either same or different and are each, independently represent hydrogen, deuterium, aryl selected from the group of C ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ of Lt; / RTI >

That is, in the formula (A), L 1 and L 2 may each contain a nitrogen atom or a sulfur atom, and when they contain a nitrogen atom or a sulfur atom, they are more preferable since they have a high transparency and a high refractive index.

In addition, at least one of the formula (A) in W1 to W3 in the present invention is substituted or unsubstituted C ₆ arylene group may be the date -C ₃₀ ring, preferably, W1 to two are a substituted or unsubstituted C of W3 ₆ or an aryl group of ₃₀ or -C W1 to W3 can all arylene date of substituted or unsubstituted C ₆ -C _30.

In this case, it is presumed that the plate structure is formed due to the aromatic plane structure of the C ₆ -C ₃₀ arylene group and the plane structure of the triazine, and thus high high-refraction characteristics can be obtained.

For example, at least one of the formula (A) in W1 to W3 is a substituted or Examples of the unsubstituted aryl group of C ₆ -C _30, wherein the formula (A) in W1 is a substituted or unsubstituted phenylene group ring, wherein W2 and W3 May be the same or different and independently of each other, a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₁ -C ₁₂ alkylene group.

As a specific example of the case where two or more of W1 to W3 are substituted or unsubstituted C ₆ -C ₃₀ arylene groups, W 1 is a substituted or unsubstituted phenylene group, W 2 and W 3 are the same At least one of them is a substituted or unsubstituted C ₆ -C ₃₀ arylene group, and W 1 to W 3 are the same or different, and at least two of them are a substituted or unsubstituted phenylene group Or W1 to W3 are the same or different and each is a substituted or unsubstituted phenylene group.

On the other hand, the above-mentioned [Chemical Formula B] and [Chemical Formula C] within substituents R8 to R12 are preferably identical or different and, independently from each other hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C ₂₀ respectively according to the present invention , substituted or unsubstituted and which is selected from aryl groups unsubstituted C ₆ -C ₂₀ a, Ra, Rb and Rc is preferably any of the substituents, the same or different and independently selected from hydrogen, deuterium, a methyl group from each other, respectively Lt; / RTI >

At least one of Y 3 and Y 5 in the above formulas (B) and (C) may be a structural formula 1 or a structural formula 2. By having such a structure, both ends of the monomer have a double bond, Can be adjusted.

In the formula (B), L 3 to L 7 are the same or different and independently of each other, a single bond, -N (-R 9) - or S, and two or more of L 3 to L 7 are each -N ) each in the case of selecting -N (-R9) - are either the same or different, independently represent hydrogen, deuterium, aryl selected from the group of C ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ of Lt; / RTI >

In the above formula (C), L3 to L5 are the same or different and independently of each other, a single bond, -N (-R9) - or S, and two or more of L3 to L5 are each -N ) each in the case of selecting -N (-R9) - are either the same or different, independently represent hydrogen, deuterium, aryl selected from the group of C ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ of Lt; / RTI >

Herein, L3 to L7 in the above formulas (B) and (C) may contain a nitrogen atom or a sulfur atom, and when they contain a nitrogen atom or a sulfur atom, they have a high transparency and a high refractive index, Do.

The one selected from Formula B] and [Chemical Formula C] within R9, R11 to R12 are the same or different and each independently represent hydrogen, deuterium, aryl group of C ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ of each other It can be one.

Further, the above-mentioned [Chemical Formula B] and [Chemical Formula C] within a W4 or to two of the aryl group a substituted or unsubstituted C ₆ -C ₃₀ or of W7, W4 to more than two of W7 is a substituted or unsubstituted according to the present invention hwandoen or C ₆ -C ₃₀ arylene group, or W4 through W7 may both be an arylene group substituted or unsubstituted C ₆ -C _30.

In this case, it is presumed that the plate structure is formed due to the aromatic plane structure of the C ₆ -C ₃₀ arylene group and the plane structure of the triazine, and thus high high-refraction characteristics can be obtained.

For example, in the case where at least two of W4 to W7 in the above formulas (B) and (C) are substituted or unsubstituted C ₆ -C ₃₀ arylene groups, at least two of W 4 to W 7 Or a substituted or unsubstituted phenylene group.

In this case, the W4 to the remaining one or two phenylene groups, not of W7 are the same or different and independently of each other a single bond, an arylene group, a substituted or unsubstituted substituted or unsubstituted C ₆ -C ₃₀ ring And may be a C ₁ -C ₁₂ alkylene group.

In the present invention, as a specific example of the case where at least three of W4 to W7 in the above formulas (B) and (C) are substituted or unsubstituted C ₆ -C ₃₀ arylene groups, And all or four of them may be a substituted or unsubstituted phenylene group. Wherein the W4 through W7 3 dogs substituted or unsubstituted on the remaining unsubstituted phenylene group is not phenylene group one is a single bond, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C of Or an alkylene group of _{1 to 12} carbon atoms.

Specific examples of the compounds represented by any one of the above-mentioned formulas (A) to (C) in the present invention may be compounds represented by any one of the compounds 1 to 134 described in the following Table 1, but are not limited thereto.

[Compound 1] [Compound 2]

[Compound 3] [Compound 4]

[Compound 5] [Compound 6]

[Compound 7] [Compound 8]

[Compound 9] [Compound 10]

[Compound 11] [Compound 12]

[Compound 13] [Compound 14]

[Compound 15] [Compound 16]

[Compound 17] [Compound 18]

[Compound 19] [Compound 20]

[Compound 21] [Compound 22]

[Compound 23] [Compound 24]

[Compound 25] [Compound 26]

[Compound 27] [Compound 28]

[Compound 29] [Compound 30]

[Compound 31] [Compound 32]

[Compound 33] [Compound 34]

[Compound 35] [Compound 36]

[Compound 37] [Compound 38]

[Compound 39] [Compound 40]

[Compound 41] [Compound 42]

[Compound 43] [Compound 44]

[Compound 45] [Compound 46]

[Compound 47] [Compound 48]

[Compound 49] [Compound 50]

[Compound 51] [Compound 52]

[Compound 53] [Compound 54]

[Compound 55] [Compound 56]

[Compound 57] [Compound 58]

[Compound 59] [Compound 60]

[Compound 61] [Compound 62]

[Compound 63] [Compound 64]

[Compound 65] [Compound 66]

[Compound 67] [Compound 68]

[Compound 69] [Compound 70]

[Compound 71] [Compound 72]

[Compound 73] [Compound 74]

[Compound 75] [Compound 76]

[Compound 77] [Compound 78]

[Compound 79] [Compound 80]

[Compound 81] [Compound 82]

[Compound 83] [Compound 84]

[Compound 85] [Compound 86]

[Compound 87] [Compound 88]

[Compound 89] [Compound 90]

[Compound 91] [Compound 92]

[Compound 93] [Compound 94]

[Compound 95] [Compound 96]

[Compound 97] [Compound 98]

[Compound 99] [Compound 100]

[Compound 101] [Compound 102]

[Compound 103] [Compound 104]

[Compound 105] [Compound 106]

[Compound 107] [Compound 108]

[Compound 109] [Compound 110]

[Compound 111] [Compound 112]

[Compound 113] [Compound 114]

[Compound 115] [Compound 116]

[Compound 117] [Compound 118]

[Compound 119] [Compound 120]

[Compound 121] [Compound 122]

[Compound 123] [Compound 124]

[Compound 125] [Compound 126]

[Compound 127] [Compound 128]

[Compound 129] [Compound 130]

[Compound 131] [Compound 132]

[Compound 133] [Compound 134]

On the other hand, the present invention provides a photosensitive composition comprising a compound represented by any one of the above-mentioned formulas (A) to (C).

That is, the compound represented by any one of the above-mentioned formulas (A) to (C) according to the present invention may be contained in the photoreactive composition as a photocrosslinkable monomer to form a thin film or a prism by light such as UV, When the composition is used in a composition for a display or an electronic material, it has an excellent compatibility with a solvent or an acrylic monomer.

The compounds represented by any one of the above-mentioned formulas (A) to (C) are excellent in refractive index, transmittance and yellowing resistance and can improve brightness and performance when used as a high refractive index monomer for TFT-LCD and OLED.

Meanwhile, the photosensitive composition may further include a photoinitiator or a photopolymerizable monomer, and may include, but not limited to, a substance used in other known photosensitive compositions.

The present invention also provides an optical article obtained by polymerizing the photosensitive composition.

In one embodiment of the photosensitive composition of the present invention, 1 to 95 parts by weight of a compound represented by any one of the above formulas (A) to (C), 0 to 90 parts by weight of a photopolymerizable compound and 0.1 to 20 parts by weight of a photoinitiator.

Here, the photopolymerizable compound means a compound containing one or two or more acryl groups, methacrylic groups or vinyl groups, and the photoinitiator according to the present invention is a compound which is formed by radicals generated by UV and crosslinked by the generated radicals. The photopolymerizable compound may be an alkyl acrylate such as hexyl (meth) acrylate, cyclohexyl (meth) acrylate, tetradecyl (meth) acrylate and hexadecyl (meth) acrylate; (Meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, (Meth) acrylate, trimethylol propane di (meth) acrylate, trimethylol propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, acrylic acid, methacrylic acid, glycidyl acrylate, .

Examples of the photoinitiator include ketones, ketoacetals, thioguanthones, phosphine oxides, anthraquinones, trichloromethyl triazine, and oxime esters. Specific examples of such photo initiators include phenylbiphenyl ketone, 1-benzyl-1-dimethylamino-1- (4-morpholino-benzoyl) propane, 1-hydroxy-1-benzoylcyclopentane, Benzoyl-4-methylphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoyl propane, 2-methyl- Butylbenzoyl trichloromethane, 4-phenoxybenzoyl dichloromethane, diphenyl-2,4,6-trimethylbenzoylphosphine oxide, methyl benzoylformate, methyl benzoate, (Trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) Naphthyl-4,6-bis (trichloromethyl) -s-triazine, 1- [9-ethyl-6- (2 -Methylbenzoyl) -9H-carbazol-3-yl] -ethanone- 1- (O-acetyloxime), 1- ) -9H-carbazol-3-yl] ethanone, and 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] .

Such a photoinitiator is more preferably used in an amount of 0.1 to 20 parts by weight, preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive composition, in order to control exposure sensitivity and pattern characteristics.

In addition, an organic solvent may optionally be used to dissolve the photosensitive composition, Is used for improving the coating property, and it is preferable to use an organic solvent as such solvent.

As the organic solvent, preferably ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethyl ethyl ether, methyl methoxy propionate, ethyl ethoxypropionate (EEP), ethyl lactate, propylene glycol Methyl ether acetate (PGMEA), propylene glycol methyl ether, propylene glycol propyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol methyl acetate, diethylene glycol ethyl acetate, acetone, methyl isobutyl ketone, (NMP), gamma -butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol dimethyl ether The reaction conditions are as follows: Diglyme, tetrahydrofuran (THF), methanol, ethanol, propanol, iso-propanol, methyl cellosolve, ethyl cellosolve, The solvent may be used in an amount of from 0 to 90% by weight, based on 100 parts by weight of the photosensitive composition, of at least one member selected from the group consisting of methyl ethyl ketone, diethyleneglycol ethyl ether, dipropylene glycol methyl ether, toluene, xylene, hexane, By weight.

Further, the photosensitive composition according to the present invention can be used for producing any one selected from a prism sheet, a microlens, a coating material for LCD, a DBEF film, a coating material for an organic light emitting diode (OLED) have.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

Representative methods for synthesizing the compound having an acrylic group represented by any one of the above-mentioned [Chemical Formulas A], [Chemical Formula B] and [Chemical Formula C] are shown in the following Reaction Scheme 1.

[Reaction Scheme 1]

The reaction scheme 1 shows a synthetic mechanism for a part of the compounds having an acryl group and may be appropriately substituted with a substituent such that the substituent is appropriately substituted with a substituent selected from the group consisting of a variety of acrylic groups represented by any one of the formulas (A), (B) Compounds can be synthesized.

Synthesis Example 1: Preparation of Compound 2

Synthesis Example 1-1. Preparation of 3,3 ', 3' '- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl)) triphenol

300 ml of THF is added to a 1 L reactor, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 35.5 g (325.4 mmol) of 3-aminophenol is added slowly with stirring for 30 minutes, then 20.0 g (244.0 mmol) of sodium acetate Molecular Weight: 82.03 is added. The reaction vessel is heated to 80 ^° C and stirred for 10 hours. After completion of the reaction, 300 ml of distilled water was added and stirred to obtain 40.1 g (yield: 92%) of a solid white 3,3 ', 3''- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl) %).

Synthesis Example 1-2. Preparation of Compound 2

A 250 ml reactor was charged with 100 ml of THF, 30 ml of triethylamine and 10.0 g (24.9 mmol) of 3,3 ', 3''- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl) And cooled to 0 ^° C under nitrogen. 4.5 g (49.7 mmol) of acryloyl chloride is slowly added to the above reaction vessel for 30 minutes, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . After concentration under reduced pressure, column purification was carried out with ethyl acetate: hexane = 1: 3 to obtain 11.5 g (yield 91%) of [Compound 2].

Synthesis Example 2: Preparation of Compound 4

Synthesis Example 2-1. Preparation of 4,4 ', 4' '- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl)) triphenol

In a 1 L reactor, 250 ml of THF is added, and 15.0 g (81.3 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 26.6 g (244.0 mmol) of 4-aminophenol is added slowly with stirring for 30 minutes, then 20.0 g (244.0 mmol) of sodium acetate is added. The reaction vessel is heated to 80 ^° C and stirred for 10 hours. After completion of the reaction, 250 ml of distilled water was added and stirred to obtain 30.8 g of white solid 4,4 ', 4''- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl) %).

Synthesis Example 2-2. Preparation of compound 4

A 250 ml reactor was charged with 100 ml of THF, 30 ml of triethylamine and 10.0 g (24.9 mmol) of 4,4 ', 4''- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl) And cooled to 0 ^° C under nitrogen. 7.4 g (82.2 mmol) of acryloyl chloride is slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure, and then subjected to column purification with ethyl acetate: hexane = 1: 3 to obtain 12.5 g (yield 89%) of [Compound 4].

Synthesis Example 3: Preparation of Compound 12

Synthesis Example 3-1. Preparation of 4,4 ', 4' '- ((1,3,5-triazine-2,4,6-triyl) tris (methylazanediyl) triphenol

In a 500 mL reactor, 150 mL of THF is added, and 10.0 g (54.2 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 20.0 g (162.6 mmol) of 4- (methylamino) phenol is added slowly with stirring for 30 minutes, then 13.3 g (244.0 mmol) of sodium acetate are added. The reaction vessel is heated to 80 ^° C and stirred for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain 21.7 g of white solid 4,4 ', 4''- ((1,3,5-triazine-2,4,6-triyl) tris (methylazanediyl) %).

Synthesis Example 3-2. Preparation of Compound 12

120 ml of THF, 20 ml of triethylamine and 12.0 g (27.0 mmol) of 4,4 ', 4''- ((1,3,5-triazine-2,4,6-triyl) tris (methylazanediyl) And cooled to 0 ^° C under nitrogen. 2.4 g (27.0 mmol) of acryloyl chloride is slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . After concentration under reduced pressure, column purification was carried out with ethyl acetate: hexane = 1: 3 to obtain 10.4 g (yield 93%) of [Compound 12].

Synthesis Example 4: Preparation of Compound 25

Synthesis Example 4-1. Preparation of 3,3 ', 3' '- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl)) triphenol

Was prepared in the same manner as in Synthesis Example 1-1.

Synthesis Example 4-2. 2,2 ', 2' - (((1,3,5-triazine-2,4,6-triyl) tris (azaneediyl) tris (benzene-3,1- Preparation of triethanol

To a 250 mL reactor was added 100 mL of DMF and 10 g (24.9 mmol) of 3,3 ', 3''- ((1,3,5-triazine-2,4,6-triyl) tris (azanediyl)) triphenol ) And 10.3 g (74.7 mmol) of K ₂ CO ₃ are added. 11.2 g (89.5 mmol) of 2-bromoethanol was slowly added to the reactor for 30 minutes, followed by stirring at 80 ^° C for 10 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was separated. The ethyl acetate layer was washed twice with distilled water. The organic layer was dried over MgSO ₄ and concentrated under reduced pressure to obtain a white solids 2,2 ', 2 "- ((((1,3,5-triazine-2,4,6-triyl) tris (azanediyl) ) tris (benzene-3,1-diyl)) tris (oxy)) triethanol (yield: 96%).

Synthesis Example 4-3. Preparation of Compound 25

To a 500 ml reactor were added 200 ml of THF, 20 ml of triethylamine and 20 ml of 2,2 ', 2''- (((1,3,5-triazine-2,4,6-triyl) tris (azene) -diyl)) tris (oxy)) triethanol (20.0 g, 37.4 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 10.2 g (112.2 mmol) of acryloyl chloride is slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 15 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . After concentration under reduced pressure, the residue was subjected to column purification with ethyl acetate: hexane = 1: 4 to obtain 22.2 g (yield 85%) of [Compound 25].

Synthesis Example 5: Preparation of Compound 40

Synthesis Example 5-1. Preparation of 3,3 '- ((6- (phenylamino) -1,3,5-triazine-2,4-diyl) bis (azanediyl) diphenol

120 mL of THF is added to a 500 mL reactor, and 12.0 g (65.1 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 14.2 g (130.2 mmol) of 3-aminophenol and 8.0 g (65.1 mmol) of 4-methoxyaniline were slowly added in succession for 30 minutes each with stirring. 16.0 g (195.3 mmol) . The reaction vessel is heated to 80 ^° C and stirred for 10 hours. After completion of the reaction, 120 ml of distilled water was added and stirred to obtain white solid 3,3 '- ((6 - ((4-methoxyphenyl) amino) -1,3,5-triazine-2,4-diyl) bis (azanediyl) (Yield: 84%).

Synthesis Example 5-2. Preparation of Compound 40

To a 250 ml reactor were added 100 ml of THF, 20 ml of triethylamine and 8.0 g of 3,3 '- ((6 - ((4-methoxyphenyl) amino) -1,3,5-triazine-2,4-diyl bis azanediyl) diphenol 19.2 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 4.0 g (38.4 mmol) of methacryloyl chloride is slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure and then subjected to column purification with ethyl acetate: hexane = 1: 5 to obtain 10.4 g (yield 90%) of [Compound 40].

Synthesis Example 6: Preparation of Compound 81

Synthesis Example 6-1. Preparation of 2,2 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4-diyl) bis (sulfanediyl)) diethanol

150 mL of THF is added to a 500 mL reactor, and 15.0 g (81.3 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 5.0 g (81.3 mmol) of 2-aminoethanol and 12.7 g (162.6 mmol) of 2-mercaptoethanol were slowly added in succession for 30 min each time with stirring, and 20.0 g (243.9 mmol) . The reaction vessel is heated to 80 ^° C and stirred for 15 hours. After the completion of the reaction, distilled water and ethyl acetate are added and removed. After the organic layer is washed with distilled water, MgSO ₄ is added to remove moisture, and then the solvent is removed. Diethanol was obtained by separating the column from EA and hexane 1: 3 to obtain 18.6 g of 2,2 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine- (Yield: 78%).

Synthesis Example 6-2. Preparation of Compound 81

To a 250 ml reactor were added 120 ml of THF, 30 ml of triethylamine and 12.0 g of (2 - ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4-diyl bis (sulfanediyl) 41.0 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. Add 11.1 g (123.1 mmol) of acryloyl chloride to the above reaction vessel slowly for 30 minutes, and then stir at room temperature for 10 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure, and then subjected to column purification using ethyl acetate: hexane = 1: 5 to obtain 17.2 g (yield 92%) of [Compound 81].

Synthesis Example 7: Preparation of Compound 83

Synthesis Example 7-1. Preparation of 2,2 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4-diyl) bis (oxy)) diethanol

150 mL of THF is added to a 500 mL reactor, and 15.0 g (81.3 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 5.0 g (81.3 mmol) of 2-aminoethanol and 10.0 g (162.6 mmol) of ethane-1,2-diol were slowly added for 30 min each time with stirring. 244.0 mmol) is added. The reaction vessel is heated to 80 ^° C and stirred for 15 hours. After the completion of the reaction, distilled water and ethyl acetate are added and removed. After the organic layer is washed with distilled water, MgSO ₄ is added to remove moisture, and then the solvent is removed. The reaction mixture was separated by column chromatography with EA and hexane 1: 3 to obtain 16 g of 2,2 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4- Yield: 76%).

Synthesis Example 7-2. Preparation of Compound 83

To a 250 ml reactor were added 100 ml of THF, 30 ml of triethylamine and 10.0 g of 2,2 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine- 38.4 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 10.4 g (115.2 mmol) of acryloyl chloride is slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography with ethyl acetate: hexane = 1: 5 to obtain 15.2 g (yield 94%) of [Compound 83].

Synthesis Example 8: Preparation of Compound 85

Synthesis Example 8-1. Preparation of 2,2 '- ((6 - ((2-hydroxyethyl) thio) -1,3,5-triazine-2,4-diyl) bis (methylazanediyl)) diethanol

150 mL of THF is added to a 500 mL reactor, and 15.0 g (81.3 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 6.3 g (81.3 mmol) of 2-mercaptoethanol and 12.2 g (162.6 mmol) of 2- (methylamino) ethanol were slowly added sequentially with stirring for 30 minutes each. mmol). The reaction vessel is heated to 80 ^° C and stirred for 15 hours. After the completion of the reaction, distilled water and ethyl acetate are added and removed. After the organic layer is washed with distilled water, MgSO ₄ is added to remove moisture, and then the solvent is removed. Diethanol was obtained by separating the column from EA and hexane 1: 3 to obtain 19.0 g of 2,2 '- ((6 - ((2-hydroxyethyl) thio) -1,3,5-triazine-2,4-diyl) bis (methylazanediyl) (Yield: 77%).

Synthesis Example 8-2. Preparation of Compound 85

A 250 ml reactor was charged with 100 ml of THF, 20 ml of triethylamine and 10.0 g of 2,2 '- ((6 - ((2-hydroxyethyl) thio) -1,3,5-triazine-2,4-diyl) bis (methylazanediyl) 32.9 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 10.3 g (98.8 mmol) of methacryloyl chloride was slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The reaction mixture was concentrated under reduced pressure, and then subjected to column purification with ethyl acetate: hexane = 1: 5 to obtain 15.0 g (yield: 90%) of [Compound 85].

Synthesis Example 9: Preparation of Compound 99

Synthesis Example 9-1. Preparation of 3,3 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4-diyl) bis (sulfanediyl) diphenol

150 mL of THF is added to a 500 mL reactor, and 15.0 g (81.3 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 4.9 g (81.3 mmol) of 2-aminoethanol and 20.5 g (162.6 mmol) of 3-mercaptophenol were slowly added in succession for 30 minutes each time with stirring. 20.0 g (244.0 mmol) . The reaction vessel is heated to 80 ^° C and stirred for 15 hours. After the completion of the reaction, distilled water and ethyl acetate are added and removed. After the organic layer is washed with distilled water, MgSO ₄ is added to remove moisture, and then the solvent is removed. Diacetyl) diphenol) 23.0 g of 3,3 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine- (Yield: 73%).

Synthesis Example 9-2. Bis (3,1-phenylene)) bis ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4-diyl bis (sulfanediyl) oxy)) diethanol

To a 250 mL reactor, 100 mL of DMF was added, and 3,3 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine-2,4-diyl) bis (sulfanediyl) diphenol 10.0 g (25.7 mmol) of K ₂ CO _{3 and} 7.1 g (51.4 mmol) of K ₂ CO ₃ are added. 6.4 g (51.4 mmol) of 2-bromoethanol is slowly added to the reactor for 30 minutes and then stirred at 80 ^° C for 10 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was separated. The ethyl acetate layer was washed twice with distilled water. The organic layer was dried over MgSO ₄ , and concentrated under reduced pressure to give a white solid. 2 - ((((6- (2-hydroxyethyl) amino) -1,3,5-triazine- ) bis (sulfanediyl)) bis (3,1-phenylene)) bis (oxy)) diethanol.

Synthesis Example 9-3. Preparation of Compound 99

To a 250 ml reactor were added 100 ml of THF, 20 ml of triethylamine and 20 ml of 2,2 '- (((6- (2-hydroxyethyl) amino) -1,3,5-triazine- 3,1-phenylene)) bis (oxy)) diethanol (10.0 g, 20.9 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 5.7 g (62.9 mmol) of acryloyl chloride was slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure and then subjected to column purification with ethyl acetate: hexane = 1: 4 to obtain 12.6 g (yield 94%) of [Compound 99].

Synthesis Example 10: Preparation of Compound 109

Synthesis Example 10-1. Preparation of 4,6-dichloro-N- (4,6-dichloro-1,3,5-triazin-2-yl) -N-phenyl-1,3,5-triazin-2-

200 mL of THF is added to a 500 mL reactor, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 5.0 g (54.2 mmol) of aniline was added slowly with stirring for 30 minutes, then 17.8 g (216.9 mmol) of sodium acetate was added. Stir at room temperature for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain a white solid 4,6-dichloro-N- (4,6-dichloro-1,3,5-triazin- triazin-2-amine (yield: 83%).

Synthesis Example 10-2. Bis (1,3,5-triazine-6,4,2-triyl) tetrakis (azanediyl)) tetraphenol of the formula: 4,4 ', 4 ", 4" Produce

200 ml of THF was added to a 500 ml reactor and 4,6-dichloro-1,3,5-triazin-2-yl) -N-phenyl-1,3,5- triazin-2-amine (17.5 g, 45.0 mmol). After cooling the reaction flask to 0 ^° C, 19.7 g (180.0 mmol) of 4-aminophenol was slowly added for 30 minutes while stirring, and 14.8 g (180.0 mmol) of sodium acetate was added thereto. The reaction vessel is heated to 80 < 0 > C and stirred for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain white solids 4,4 ', 4 ", 4"' - ((6,6 '- (phenylazanediyl) bis 2-triyl)) tetrakis (azanediyl)) tetraphenol (yield: 91%).

Synthesis Example 10-3. Preparation of Compound 109

A 500 ml reactor was charged with 200 ml of THF, 4,4 ', 4'',4''' - ((6,6 '- (phenylazanediyl) bis (1,3,5-triazine-6,4,2- (azanediyl)) tetraphenol (27.8 g, 41.0 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 14.8 g (163.8 mmol) of acryloyl chloride is slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure, and then subjected to column purification with ethyl acetate: hexane = 1: 3 to obtain 30.8 g (yield: 84%) of [Compound 109].

Synthesis Example 11: Preparation of Compound 110

Synthesis Example 11-1. Preparation of 4,6-dichloro-N- (4,6-dichloro-1,3,5-triazin-2-yl) -N-phenyl-1,3,5-triazin-2-

200 mL of THF is added to a 500 mL reactor, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 5.0 g (54.2 mmol) of aniline was added slowly with stirring for 30 minutes, then 17.8 g (216.9 mmol) of sodium acetate was added. Stir at room temperature for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain a white solid 4,6-dichloro-N- (4,6-dichloro-1,3,5-triazin- triazin-2-amine (yield 81%).

Synthesis Example 11-2. 3,3 ', 3 ", 3' '- ((6,6' - (phenylazanediyl) bis (1,3,5-triazine-6,4,2-triyl) tetrakis (azanediyl) Produce

200 ml of THF was added to a 500 ml reactor and 4,6-dichloro-1,3,5-triazin-2-yl) -N-phenyl-1,3,5- triazin-2-amine (17.1 g, 43.9 mmol). After cooling the reaction flask to 0 ^° C, 19.2 g (175.7 mmol) of 3-aminophenol was slowly added over 30 minutes with stirring and 14.4 g (175.7 mmol) of sodium acetate was added. The reaction vessel is heated to 80 < 0 > C and stirred for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain white solid 3,3 ', 3'',3''' - ((6,6 '- (phenylazanediyl) bis 2-triyl)) tetrakis (azanediyl)) tetraphenol (yield 90%).

Synthesis Example 11-3. Preparation of Compound 110

To a 500 ml reactor were added 200 ml of THF, 3,3 ', 3'',3''' - ((6,6 '- (phenylazanediyl) bis (1,3,5-triazine-6,4,2- (azanediyl)) tetraphenol (26.9 g, 39.5 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 16.5 g (158.13 mmol) of methacryloyl chloride was slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure, and then subjected to column purification with ethyl acetate: hexane = 1: 3 to obtain 30.9 g (yield: 82%) of [Compound 110].

Synthesis Example 12: Preparation of Compound 122

Synthesis Example 12-1. Preparation of N1, N3-bis (4,6-dichloro-1,3,5-triazin-2-yl) benzene-1,3-diamine

200 mL of THF is added to a 500 mL reactor, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 5.9 g (54.2 mmol) of benzene-1,3-diamine is added slowly with stirring for 30 minutes and then 17.8 g (216.9 mmol) of sodium acetate are added. Stir at room temperature for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain 15.5 g (yield: 71%) of white solid N1 and N3-bis (4,6-dichloro-1,3,5-triazin- .

Synthesis Example 12-2.

Bis (1,3,5-triazine-6,4,2-triyl)) -, (4,6 ' tetrakis (azanediyl)) tetraphenol

200 mL of THF was charged into a 500 mL reactor and 15.5 g (38.5 mmol) of N1, N3-bis (4,6-dichloro-1,3,5-triazin- . After cooling the reaction flask to 0 ^° C, 16.8 g (154.0 mmol) of 4-aminophenol was slowly added for 30 minutes while stirring, and 12.6 g (154.0 mmol) of sodium acetate was added thereto. The reaction vessel is heated to 80 < 0 > C and stirred for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain white solid 4,4 ', 4'',4''' - ((6,6 '- (1,3-phenylenebis (azanediyl) -triazine-6,4,2-triyl)) tetrakis (azanediyl)) tetraphenol (yield 89%).

Synthesis Example 12-3. Preparation of Compound 122

To a 500 ml reactor were added 200 ml of THF, 4,4 ', 4'', 4 "' - ((6,6 '- (1,3-phenylenebis (azanediyl) , 2-triyl)) tetrakis (azanediyl)) tetraphenol (23.8 g, 34.3 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. Add 12.4 g (137.0 mmol) of acryloyl chloride to the above reaction vessel slowly for 30 minutes and then stir at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure, and then subjected to column purification with ethyl acetate: hexane = 1: 3 to obtain 26.5 g (yield: 85%) of [Compound 122].

Synthesis Example 13: Preparation of Compound 123

Synthesis Example 13-1. Preparation of N1, N3-bis (4,6-dichloro-1,3,5-triazin-2-yl) benzene-1,3-diamine

200 mL of THF is added to a 500 mL reactor, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ^° C, 5.9 g (54.2 mmol) of benzene-1,3-diamine is added slowly with stirring for 30 minutes and then 17.8 g (216.9 mmol) of sodium acetate are added. Stir at room temperature for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain 16.4 g (yield 75%) of white solid N1 and N3-bis (4,6-dichloro-1,3,5-triazin- .

Synthesis Example 13-2.

3,3 ', 3' ', 3' '- ((6,6' - (1,3-phenylenebis (azanediyl) bis (1,3,5-triazine-6,4,2- tetrakis (azanediyl)) tetraphenol

200 mL of THF was charged into a 500 mL reactor and 16.4 g (40.7 mmol) of N1, N3-bis (4,6-dichloro-1,3,5-triazin- . After cooling the reaction flask to 0 ^° C, 17.8 g (162.7.0 mmol) of 3-aminophenol was slowly added over 30 minutes while stirring, and 13.3 g (162.7.0 mmol) of sodium acetate was added thereto. The reaction vessel is heated to 80 < 0 > C and stirred for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to obtain white solid 3,3 ', 3'',3''-((6,6' - (1,3-phenylenebis (azanediyl) -triazine-6,4,2-triyl)) tetrakis (azanediyl)) tetraphenol (yield 90%).

Synthesis Example 13-3. Preparation of Compound 123

To a 500 ml reactor were added 200 ml of THF, 3,3 ', 3'',3''-((6,6' - (1,3,6-phenylenebis (azanediyl) , 2-triyl)) tetrakis (azanediyl) tetraphenol (25.4 g, 36.6 mmol) were successively added thereto, followed by cooling to 0 ^° C under nitrogen. 15.3 g (146.4 mmol) of methacryloyl chloride is slowly added to the above reaction vessel for 30 minutes, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and the organic layer was dried using MgSO ₄ . The mixture was concentrated under reduced pressure, and then subjected to column purification with ethyl acetate: hexane = 1: 3 to obtain 30.1 g (yield: 85%) of [Compound 123].

Examples 1 to 16

(B) a photopolymerizable monomer, (C) a photoinitiator D) a release agent, and (E) a UV stabilizer in a composition ratio shown in Table 2, Followed by stirring to prepare a photosensitive composition.

The types of additives used in Examples 1 to 16 and Comparative Examples 1 to 2 are as described below.

(A) an acrylic group-containing monomer

Compound 2 (M2): ((6 - ((3-hydroxyphenyl) amino) -1,3,5-triazine-2,4-diyl) bis Nylene) diacrylate

Compound 4 (M4): ((1,3,5-triazine-2,4,6-triyl) tris (acafil)) tris (benzene-4,1-diyl) triacrylate

Compound 12 (M12): 4 - ((4,6-bis ((4-hydroxyphenyl) (methyl) amino) -1,3,5-triazin-

Compound 25 (M25): ((((1,3,5-triazine-2,4,6-triyl) tris (azaneil)) tris (benzene- ) Tris (ethane-2,1-diyl) triacrylate

Compound 40 (M40): ((6 - ((4-methoxyphenyl) amino) -1,3,5-triazine-2,4- Bis (2-methyl acrylate)

Compound 81 (M81): ((6- ((2- (acryloyloxy) ethyl) amino) -1,3,5-triazine-2,4-diyl) bis (sulfanediyl) 2,1-diyl) diacrylate

Compound 83 (M83): ((6- ((2- (acryloyloxy) ethyl) amino) -1,3,5-triazine-2,4-diyl) bis (oxy) , 1-diyl) diacrylate

Compound 85 (M85): ((6 - ((2- (methacryloxy) ethyl) thio) -1,3,5-triazine-2,4- -2,1-diyl) bis (2-methyl acrylate)

Compound 99 (M99): ((((6- ((2- (acryloxy) ethyl) amino) -1,3,5-triazine-2,4-diyl) bis (sulfanediyl) 1-phenylene)) bis (oxy)) bis (ethane-2,1-diyl) diacrylate

Compound 109 (M109): ((6,6 '- (Phenyllaurel) bis (1,3,5-triazine-6,4,2-triyl)) tetrakis (Benzene-4,1-diyl) tetraacrylate

Compound 110 (M110): ((6,6 '- (Phenyllaurel) bis (1,3,5-triazine-6,4,2-triyl)) tetrakis (Benzene-3,1-diyl) tetrakis (2-methylacrylate)

Compound 122 (M122): ((6,6 '- (1,3-phenylenebis (acryle)) bis (1,3,5-triazine-6,4,2-triyl)) tetrakis (Aramyl)) tetrakis (benzene-4,1-diyl) tetraacrylate

Synthesis of Compound 123 (M123): ((6,6 '- (1,3-phenylenebis (aspartyl)) bis (1,3,5-triazine-6,4,2-triyl) (Arampai)) tetrakis (benzene-3,1-diyl) tetrakis (2-methylacrylate)

(B) Photopolymerizable compound:

B1: 2 - ([1,1'-biphenyl] -2-yloxy) ethyl acrylate

     B2: dipentaerythritol pentaacrylate

(C) Photopolymerization initiator:

C1: Diphenyl-2,4,6-trimethylbenzoylphosphine oxide

C2: (1-hydroxycyclohexyl) (phenyl) methanone

       (D) Releasing agent

       D1: Silicone-based release agent

       (E) UV stabilizer

       E1: Amine-based UV stabilizer

Comparative Examples 1 to 2

In Example 1 and Example 2, the high-refraction monomers were prepared by using the following R1 (((9H-fluorene-9,9-diyl) bis (4,1- phenylene)) bis (Ethane-2, 1 -dine) diacrylate.

R1)

[Table 2]

Experimental Example 1: Evaluation of refractive index

The synthesized high-refractive-index acrylic monomer was dissolved in the same weight ratio to 2 - ([1,1'-biphenyl] -2-yloxy) ethyl acrylate and then measured by ABBE refractometer at 25 ^° C.

Experimental Example 2: Evaluation of viscosity

The high-refractive-index acrylic monomers thus synthesized were dissolved in the same weight ratio to 2 - ([1,1'-biphenyl] -2-yloxy) ethyl acrylate, and the viscosity was measured with a Brookfield viscometer at 25 ^° C.

Experimental Example 3: Evaluation of permeability

A crosslinked prism sheet specimen was prepared by UV irradiation at 500 mJ / cm ² on an optical PET substrate. The crosslinked prism sheet was measured for UV transmittance at 400 nm using a UV-vis.

EXPERIMENTAL EXAMPLE 4: Evaluation of the Probe Index (DELTA YI)

The crosslinked prism sheet was subjected to a UVA lamp 1J for 8 hours at 95 ° C for 8 hours at 60 ° C using a reliability evaluation system (QUV tester) for 120 hours and then the value of change ΔYI Respectively.

The evaluation results are shown in Table 3 below.

[Table 3]

As shown in Table 3, the photosensitive compositions of Examples 1 to 16 of the present invention exhibited remarkably high refractive index and similar viscosities to those of the compositions of Comparative Examples 1 and 2. As a result of evaluating with a prism sheet, the light transmittance was excellent as compared with the compositions of Comparative Examples 1 and 2, and it was confirmed that the yellowing property after the reliability evaluation was excellent.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

The triazine derivative compound according to the present invention is used in a photosensitive composition and exhibits a high refractive index after the photo-crosslinking process, and solves the problem of color change of the optical sheet due to yellowing phenomenon according to the prior art, (DBEF) film, a coating material for an organic light emitting device (OLED), an optical lens, a multifocal lens, and the like can be provided. It is possible to apply it as a material for industrial application.

Claims (24)

1. A compound represented by any one of the following formulas (A) to (C).

   (A)

   

   In the above formula (A)

   Ra is any substituent selected from hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₆ alkyl group,

   Wherein L1 is a single bond, O, S, or -N (-R5) -,

   L2 is a single bond, O, S, or -N (-R6) -,

   X 1 to X 3 are the same or different and independently of each other are a single bond, O, S, -N (-R 7) - or -O ((CH ₂ ) _m O) _n - n is an integer selected from 1 to 4, and at least two of X1 to X3 each represent -N (-R7) -, or two or more of X1 to X3 each independently represent - _{O ((CH 2) m O} ) n - each -N (-R7) in the case of selecting - and _{-O ((CH 2) m O} ) n - may be identical to or different from each other, and

   Wherein R4 to R7 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₃₀ an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted C ₆ -C ₅₀ ring, each ring of A C ₃ -C ₃₀ cycloalkyl group, and a substituted or unsubstituted C ₇ -C ₂₄ arylalkyl group,

   Wherein W1 is any one selected from an alkylene group of a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or unsubstituted C ₁ -C ₁₂ a,

   Wherein W2 and W3 are the same or different and each independently represent a single bond, a substituted or unsubstituted C ₁ a C ₆ aryl group, a substituted or unsubstituted ring of -C ₃₀ alkylene group, a substituted or unsubstituted -C ₃₀ unsubstituted C ₂ -C ₃₀ of alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group, the substituted or unsubstituted C ₂ -C ₅₀ hetero arylene group, and any one is selected from a substituted or unsubstituted heterocycloalkyl group of C ₂ -C ₃₀ a,

   Wherein Y1 and Y2 are the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or non-substituted of unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ of each ring C, respectively of ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkynyl of the group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group , A substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, a substituted or unsubstituted A C ₆ -C ₃₀ arylsilyl group, and a substituent group represented by the following structural formula 1 or 2:

   [Structural formula 1] [Structural formula 2]

   

   In the above Structural Formula 1 and Structural Formula 2,

   Wherein Rb and Rc are each the same or different, and independently are any one selected from the group consisting of hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C ₆ with each other,

   "- *" in the structural formulas 1 and 2 means a bonding site in which X2 or X3 in the above formula (A) is bonded,

   [Chemical Formula B]

   

   ≪ RTI ID = 0.0 &

   

   In the above formula (B)

   Wherein Ar 1 is a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or unsubstituted C ₂ -C ₃₀ heteroarylene group, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, and the one which is C ₂ -C ₃₀ alkenylene group, selected from substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group of the,

   L6 is any one selected from a single bond, O, S, -N (-R11) -,

   L7 is any of a single bond, O, S, -N (-R12) -,

   In the above formula (C)

   Substituted or unsubstituted C ₆ -C ₃₀ aryl group, substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkyl group, substituted Or an unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, or a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group,

   In the above formulas (B) to (C)

   Wherein Rd is a substituent of any one selected from hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C _6,

   Each of L3 to L5 is the same or different and independently selected from a single bond, O, S, or -N (-R9) -,

   When two or more of L3 to L5 each represent -N (-R9) -, each of -N (-R9) is the same or different,

   Wherein X4 to X7 are the same or different and each, independently of one another a single bond, O, S, -N (-R10 ) -, -O ((CH 2) m O) n - are optionally replaced with one selected from said m and n are the same or different and are each independently an integer selected from 1 to 4,

   The at least two of the X4 to X7 -N (-R10) respectively select, or at least two of the X4 to X7 is _{n -O ((CH 2) m} O) , respectively - if the select on each - N (-R 10) - and -O ((CH ₂ ) _m O) _n - are the same or different,

   Wherein R8 to R12 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or unsubstituted of C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ ring, each ring of the A C ₃ -C ₃₀ cycloalkyl group, and a substituted or unsubstituted C ₇ -C ₂₄ arylalkyl group,

   W4 is any one selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, and a substituted or unsubstituted C ₁ -C ₁₂ alkylene group,

   The W5 to W7 are the same or different and each independently represent a single bond, a substituted or unsubstituted C ₁ -C ₃₀ an alkyl group, an arylene group, a substituted or unsubstituted substituted or unsubstituted C ₆ -C ₃₀ unsubstituted C ₂ -C ₃₀ of alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenyl group, the substituted or unsubstituted C ₂ -C ₅₀ hetero arylene group, and any one is selected from a substituted or unsubstituted heterocycloalkyl group of C ₂ -C ₃₀ a,

   The Y3 to Y5 are the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or non-substituted of unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ of each ring C, respectively _{3 to 30} carbon atoms, a substituted or unsubstituted C _{2 to} C ₅₀ heteroaryl group, a substituted or unsubstituted C _{2 to} C ₃₀ heterocycloalkyl group, a substituted or unsubstituted C _{1 to} C ₃₀ alkyl A silyl group, a substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, and a substituent group represented by the following Structural Formula 1 or Structural Formula 2,

   [Structural formula 1] [Structural formula 2]

   

   In the above Structural Formula 1 and Structural Formula 2,

   Wherein Rb and Rc are each the same or different, and independently are any one selected from the group consisting of hydrogen, deuterium, an alkyl group a substituted or unsubstituted C ₁ -C ₆ with each other,

   "- *" in the structural formulas 1 and 2 means a binding site in which X5 to X7 in the above-mentioned formula (B) or (C) are bonded,

   Wherein Formula A] to [Chemical Formula C] "substituted" in the "substituted or unsubstituted" in the heavy hydrogen, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group of C ₁ -C _24, C ₁ -C _A C ₂ -C ₂₄ alkenyl group, a C ₂ -C ₂₄ alkynyl group, a C ₁ - ₂₄ heteroalkyl group, a C ₆ -C ₂₄ aryl group, a C ₇ -C ₂₄ arylalkyl group, A C ₂ -C ₂₄ heteroaryl group, a C ₂ -C ₂₄ heteroarylalkyl group, a C ₁ -C ₂₄ alkoxy group, a C ₁ -C ₂₄ alkylthioyl group, a C ₁ -C ₂₄ alkylamino group, a C C ₆ -C ₂₄ arylamino groups, C ₁ -C ₂₄ heteroarylamino groups, C ₁ -C ₂₄ alkylsilyl groups, C ₆ -C ₂₄ arylsilyl groups, C ₆ -C ₂₄ aryloxy groups, C ₆ And an arylthionyl group of -C ₂₄ .
2. The method according to claim 1,

   Wherein Formula A] within the substituent R4 to R6 are each the same or different, and independently represent hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group , ≪ / RTI >

   Ra, Rb and Rc are the same or different and independently of each other are any substituent selected from the group consisting of hydrogen and a deuterium methyl group.
3. The method according to claim 1,

   Wherein at least one of Y1 and Y2 in the above formula (A) is a structural formula (1) or a structural formula (2).
4. The method according to claim 1,

   Wherein L 1 in the formula [A] is -N (-R 5) - or S, and L 2 is -N (-R 6) - or S.
5. The method according to claim 1,

   L 1 in the above formula (A) is -N (-R 5) -, L 2 is -N (-R 6) -,

   Wherein R5 and R6 are compounds, characterized in that one each of which the same or different and independently represent hydrogen, deuterium, aryl selected from the group of C ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ in.
6. The method according to claim 1,

   Wherein Formula A] in W1 to W3 of at least one compound, characterized in that the arylene group of the substituted or unsubstituted C ₆ -C _30.
7. The method according to claim 6,

   Wherein Formula A] in W1 to W3 of the two or more compounds, characterized in that the arylene group of the substituted or unsubstituted C ₆ -C _30.
8. The method according to claim 1,

   W1 in the above formula (A) is a substituted or unsubstituted phenylene group,

   Wherein W2 and W3 are the same or different, at least one of which is a compound wherein the arylene group of the substituted or unsubstituted C ₆ -C _30.
9. The method according to claim 1,

   W1 to W3 in the formula [A] are the same or different, and at least two of them are a substituted or unsubstituted phenylene group.
10. The method according to claim 1,

    The Formula B] and [Chemical Formula C] in the substituents R8 to R12 are the same or different and each is, independently, it represents a hydrogen, a deuterium, a substituted or unsubstituted C ₁ -C _20, substituted or unsubstituted C ₆ to each other, respectively and any one selected from among aryl groups -C _20,

    Rb, Rc and Rd are the same or different and independently of each other are any one substituent selected from hydrogen, deuterium and methyl.
11. The method according to claim 1,

    At least one of Y3 to Y5 in the above formulas (B) and (C) is represented by [Formula 1] or [Formula 2].
12. The method according to claim 1,

    Wherein L 3 to L 7 are the same or different and independently of one another are a single bond, -N (-R 9) - or S,
13. The method according to claim 1,

    L3 to L5 in the above formula (C) are the same or different and independently of one another are a single bond, -N (-R9) - or S.
14. The method according to claim 1,

    In the above formulas [B] and [C]

    R9, R11 to R12 are the compounds wherein any one of each of which are identical or different and independently represent hydrogen, deuterium, aryl selected from the group of C ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ in.
15. The method according to claim 1,

    The Formula B] and [Chemical Formula C] within a W4 through W7 at least two or more of these compounds, characterized in that the arylene group of the substituted or unsubstituted C ₆ -C _30.
16. 16. The method of claim 15,

    Wherein at least two of W4 to W7 in the above formulas (B) and (C) are substituted or unsubstituted phenylene groups.
17. The method according to claim 1,

    The Formula B] and [Chemical Formula C] within a W4 through W7 at least more than two of these compounds, characterized in that the arylene group of the substituted or unsubstituted C ₆ -C _30.
18. 18. The method of claim 17,

    Wherein at least three of W4 to W7 in the above formulas (B) and (C) are substituted or unsubstituted phenylene groups.
19. The method according to claim 1,

    The compound represented by any one of the above Chemical Formulas A to C is represented by any one of the following compounds 1 to 134.

    

    [Compound 1] [Compound 2]

    

    [Compound 3] [Compound 4]

    

    [Compound 5] [Compound 6]

    

    [Compound 7] [Compound 8]

    

    [Compound 9] [Compound 10]

    

    [Compound 11] [Compound 12]

    

    [Compound 13] [Compound 14]

    

    [Compound 15] [Compound 16]

    

    [Compound 17] [Compound 18]

    

    [Compound 19] [Compound 20]

    

    [Compound 21] [Compound 22]

    

    [Compound 23] [Compound 24]

    

    [Compound 25] [Compound 26]

    

    [Compound 27] [Compound 28]

    

    [Compound 29] [Compound 30]

    

    [Compound 31] [Compound 32]

    

    [Compound 33] [Compound 34]

    

    [Compound 35] [Compound 36]

    

    [Compound 37] [Compound 38]

    

    [Compound 39] [Compound 40]

    

    [Compound 41] [Compound 42]

    

    [Compound 43] [Compound 44]

    

    [Compound 45] [Compound 46]

    

    [Compound 47] [Compound 48]

    

    [Compound 49] [Compound 50]

    

    [Compound 51] [Compound 52]

    

    [Compound 53] [Compound 54]

    

    [Compound 55] [Compound 56]

    

    [Compound 57] [Compound 58]

    

    [Compound 59] [Compound 60]

    

    [Compound 61] [Compound 62]

    

    [Compound 63] [Compound 64]

    

    [Compound 65] [Compound 66]

    

    [Compound 67] [Compound 68]

    

    [Compound 69] [Compound 70]

    

    [Compound 71] [Compound 72]

    

    [Compound 73] [Compound 74]

    

    [Compound 75] [Compound 76]

    

    [Compound 77] [Compound 78]

    

    [Compound 79] [Compound 80]

    

    [Compound 81] [Compound 82]

    

    [Compound 83] [Compound 84]

    

    [Compound 85] [Compound 86]

    

    [Compound 87] [Compound 88]

    

    [Compound 89] [Compound 90]

    

    [Compound 91] [Compound 92]

    

    [Compound 93] [Compound 94]

    

    [Compound 95] [Compound 96]

    

    [Compound 97] [Compound 98]

    

    [Compound 99] [Compound 100]

    

    [Compound 101] [Compound 102]

    

    [Compound 103] [Compound 104]

    

    [Compound 105] [Compound 106]

    

    [Compound 107] [Compound 108]

    

    [Compound 109] [Compound 110]

    

    [Compound 111] [Compound 112]

    

    [Compound 113] [Compound 114]

    

    [Compound 115] [Compound 116]

    

    [Compound 117] [Compound 118]

    

    [Compound 119] [Compound 120]

    

    [Compound 121] [Compound 122]

    

    [Compound 123] [Compound 124]

    

    [Compound 125] [Compound 126]

    

    [Compound 127] [Compound 128]

    

    [Compound 129] [Compound 130]

    

    [Compound 131] [Compound 132]

    

    [Compound 133] [Compound 134]
20. A photosensitive composition comprising the compound according to any one of claims 1 to 19.
21. 21. The method of claim 20,

    Wherein the composition further comprises a photoinitiator or a photopolymerizable monomer.
22. An optical material obtained by polymerizing the photosensitive composition of claim 20.
23. 1 to 95 parts by weight of the compound according to any one of claims 1 to 19, 0 to 90 parts by weight of a photopolymerizable compound and 0.1 to 20 parts by weight of a photoinitiator per 100 parts by weight of the photosensitive composition. Composition.
24. 24. The method of claim 23,

    Wherein the photosensitive composition is used for producing any one selected from a prism sheet, a microlens, a DBEF film, a coating material for an LCD, a coating material for an OLED, an optical lens and a multifocal lens. Composition.