KR101983796B1 - Dicyanstyryl benzene derivatives and fluorescent material comprising the same - Google Patents

Abstract

The present invention relates to a dicystyryl benzene derivative represented by the following structural formula (1). Accordingly, the dicystynyl benzene derivative of the present invention can provide a fluorescent material capable of minimizing environmental pollution and improving economics by significantly reducing the amount of fluorescence yield and drastically reducing the amount of use.
[Formula 1]

Description

Dicytynyl benzene derivative and fluorescent material including the same {DICYANSTYRYL BENZENE DERIVATIVES AND FLUORESCENT MATERIAL COMPRISING THE SAME}

The present invention relates to a compound for a fluorescent material and a fluorescent dye comprising the same, and more particularly to a dicystyryl benzene derivative for a fluorescent material and a fluorescent material comprising the same.

According to the trend of the global dye industry, the development of fluorescent dye technology has been very slow since European companies (Ciba-Geigy, Bayer, BASF, etc.), which are leading companies in fluorescent dyes, reorganized their business in the early 2000s. At present, there is almost no development of new fluorescent dyes. The fluorescent dyes market has largely changed into a low-cost general-purpose fluorescent dyes market led by China, and is threatening the domestic dyes market due to the price competitiveness advantage of China's economies of scale. However, foreign buyers related to textile products are turning to the environmentally certified dye market because low-cost Chinese fluorescent dyes do not meet the requirements for producing eco-friendly textile products, and the demand for this is steadily increasing. It is necessary.

Dicyyanstyryl benzene or benzoxazole disperse fluorescent dyes used in synthetic fibers such as polyester are the result of the π-π * interaction of aromatic compounds present in these molecules. As a result, as shown below, the structural stability is maintained to form a highly aligned molecular structure.

For this reason, the process time for grinding these dyes up to the size of several micrometers (0.1 ~ 1㎛) by the current physical grinding takes about 20 ~ 24 hours, which leads to an increase in the production cost. In addition, since a large amount of dispersant and thickener are used to increase storage stability, it is a main cause of waste water generation together with undyed dyes.

In addition, in the case of dicystyryl benzene or benzoxazole, which is a conventional compound for fluorescent materials, the fluorescence yield needs to be further improved. Fluorescent dyes with greatly improved fluorescence yield can reduce the amount of use required, and thus can significantly reduce environmental pollution and improve economic efficiency. Therefore, it is necessary to improve the fluorescence yield of the compound for fluorescent materials developed in the related art.

An object of the present invention is to significantly improve the fluorescence yield according to the development of a new compound for the fluorescent material to significantly reduce the amount of use to minimize environmental pollution and improve the economics.

According to one aspect of the invention,

There is provided a dicystyryl benzene derivative represented by the following structural formula (1).

[Formula 1]

In structure 1,

R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group Or at least one of R ¹ and R ² is a substituted or unsubstituted fused C3 to C30 cycloalkyl group, in which either is bonded to a neighboring carbon atom of the bonded carbon atom, or a substituted or unsubstituted fused C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group Or at least one of R ³ and R ⁴ is a substituted or unsubstituted fused C3 to C30 cycloalkyl group which is bonded to a neighboring carbon atom of the carbon atom to which one is bonded, a substituted or unsubstituted fused C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

Preferably, the dicystyryl benzene derivative represented by the formula 1 is characterized in that represented by the following formula (2).

[Formula 2]

In structure 2,

R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group ego,

R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group to be.

Preferably, in Formula 2, R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group , A substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C1 to C30 alkylthiol group.

,

,

,

,

,

,

,

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,

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이고,More preferably, R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a C1 to C4 straight chain or a branched alkyl group, a C1 to C4 alkoxy group

,

,

,

,

,

,

,

,

,

,

, or

ego,

n ¹ to n ⁴ are each independently an integer selected from 0 to 4,

이고,X ¹ is nitrogen atom or

ego,

R ³⁹ is a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ¹ is oxygen atom, sulfur atom, or

ego,

Ar ¹ is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or Unsubstituted C1 to C30 heteroaryl group,

Y ² and Y ³ are the same as or different from each other, and each independently an oxygen atom or a sulfur atom,

R ⁵ to R ³⁸ are the same as or different from each other, and each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, It is characterized by a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

Preferably, in Formula 2, R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group , A substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C1 to C30 alkylthiol group.

,

,

,

,

,

,

,

,

,

,

, 또는

이고,More preferably, R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a C1 to C4 straight chain or a branched alkyl group, a C1 to C4 alkoxy group

,

,

,

,

,

,

,

,

,

,

, or

ego,

n ⁵ to n ⁸ are each independently an integer selected from 0 to 4,

이고,X ² is a nitrogen atom or

ego,

R ⁷⁴ is a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ⁴ is oxygen atom, sulfur atom, or

ego,

Ar ² is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or Unsubstituted C1 to C30 heteroaryl group,

Y ⁵ and Y ⁶ are the same as or different from each other, and each independently an oxygen atom or a sulfur atom,

R ⁴⁰ to R ⁷³ are the same as or different from each other, and each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, It is characterized by a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

Dicystyryl benzene derivative represented by the formula 2 is characterized in that any one selected from the following compounds 1 to 125.

According to another aspect of the invention,

It provides a fluorescent material comprising the dicystyryl benzene derivative.

The fluorescent material is any one selected from among fluorescent materials for textile dyes, light emitting materials for organic electroluminescent devices, dye materials for dye-sensitized solar cells, ink materials for ink compositions for electrical / electronic materials, and fluorescent materials for detecting target substances. Can be used as

According to another aspect of the invention,

It provides a fiber product comprising the fluorescent material.

In addition, it provides an electric and electric device comprising the fluorescent material.

Dicyyanstyryl benzene derivatives for the fluorescent material of the present invention has a significant improvement in fluorescence yield, thereby significantly reducing the amount of use, thereby minimizing environmental pollution and improving economics.

1 is a graph showing a light emission characteristic analysis results according to Test Example 1 of the present invention.

As the invention allows for various changes and numerous embodiments, particular embodiments will be illustrated and described in detail in the detailed description. However, this is not intended to limit the present invention to specific embodiments, it should be understood to include all transformations, equivalents, and substitutes included in the spirit and scope of the present invention. In the following description of the present invention, if it is determined that the detailed description of the related known technology may obscure the gist of the present invention, the detailed description thereof will be omitted.

The "substituted" means that at least one hydrogen atom is deuterium, C1 to C30 alkyl group, C3 to C30 cycloalkyl group, C2 to C30 heterocycloalkyl group, C1 to C30 halogenated alkyl group, C6 to C30 aryl group, C1 to C30 heteroaryl group, C1 to C30 alkoxy group, C3 to C30 cycloalkoxy group, C1 to C30 heterocycloalkoxy group, C2 to C30 alkenyl group, C2 to C30 alkynyl group, C6 to C30 aryloxy group, C1 to C30 heteroaryloxy group, silyl jade Period (-OSiH ₃ ), -OSiR ¹ H ₂ (R ¹ is a C1 to C30 alkyl group or a C6 to C30 aryl group), -OSiR ¹ R ² H (R ¹ and R ² are each independently a C1 to C30 alkyl group or C6 To C30 aryl group), -OSiR ¹ R ² R ³ , (R ¹ , R ² , and R ³ are each independently C1 to C30 alkyl group or C6 to C30 aryl group), C1 to C30 acyl group, C2 to C30 acyl Oxy group, C2 to C30 heteroaryloxy group, C1 to C30 sulfonyl group, C1 to C30 alkylthiol group, C3 to C30 cycloalkylthiol group, C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, C1 to C30 heteroarylthiol group, C1 to C30 amide phosphate group, silyl group (SiR ¹ R ² R ³ ₎ ( R ¹ , R ² , and R ³ are each independently a hydrogen atom, a C1 to C30 alkyl group or a C6 to C30 aryl group, an amine group (-NRR '), where R and R' are each independently a hydrogen atom It is substituted with a substituent selected from the group consisting of C1 to C30 alkyl group, and C6 to C30 aryl group), carboxyl group, halogen group, cyano group, nitro group, azo group, and hydroxy group. .

In addition, two adjacent substituents of the substituents may be fused to form a saturated or unsaturated ring.

In addition, the carbon number range of the alkyl group or the aryl group in the "substituted or unsubstituted C1 to C30 alkyl group" or "substituted or unsubstituted C6 to C30 aryl group", and the like, is unsubstituted without considering the portion substituted with the substituent. It means the total carbon number constituting the alkyl moiety or aryl moiety as viewed. For example, a phenyl group substituted with a butyl group in the para position means a aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

In addition, in the "substituted or unsubstituted C6 to C30 fused aryl group" and the like, the carbon number range of the fused aryl group is fused when it is considered to be unsubstituted without considering the substituted part, and is newly formed. It means the total carbon number which comprises an aryl part.

As used herein, "hetero" means one to four heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon unless otherwise defined.

In the present specification, "combination thereof" means that two or more substituents are bonded to a linking group or two or more substituents are condensed to each other unless otherwise defined.

In the present specification, "hydrogen" means monotium, dihydrogen, or tritium unless otherwise defined.

As used herein, unless otherwise defined, an "alkyl group" means an aliphatic hydrocarbon group.

The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.

The alkyl group may be an "unsaturated alkyl group" containing at least one double or triple bond.

The alkyl group, whether saturated or unsaturated, may be ground, straight chain or cyclic.

The alkyl group may be a C1 to C30 alkyl group. More specifically, it may be a C1 to C20 alkyl group, a C1 to C10 alkyl group, or a C1 to C6 alkyl group.

For example, a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:

Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl and cyclo A butyl group, a cyclopentyl group, a cyclohexyl group, etc. are meant.

"Amine group" includes an amino group, an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group, and may be represented by -NRR ', wherein R and R' are each independently a hydrogen atom , A C1 to C30 alkyl group, and a C6 to C30 aryl group.

A "cycloalkyl group" includes monocyclic or fused polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.

"Heterocycloalkyl group" means containing 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the rest are carbon. When the heterocycloalkyl group is a fused ring, at least one ring of the fused ring may include 1 to 4 heteroatoms.

"Aromatic group" means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.

An "aryl group" includes monocyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means containing 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the aryl group, the rest being carbon. When the heteroaryl group is a fused ring, at least one ring of the fused ring may include 1 to 4 heteroatoms.

The number of atoms of the ring in the aryl group and heteroaryl group is the sum of the number of carbon atoms and non-carbon atoms.

When used in combination with an "alkylaryl group" or an "arylalkyl group", the terms of each of the above alkyl and aryl have the meanings and content indicated above.

The term "arylalkyl group" means an aryl substituted alkyl radical such as benzyl and is included in the alkyl group.

The term "alkylaryl group" means an alkyl substituted aryl radical and is included in an aryl group.

Hereinafter, the dicystyryl benzene derivative of this invention is demonstrated. The dicystyryl benzene derivative of the present invention may be represented by the following structural formula (1).

[Formula 1]

In structure 1,

R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group Or at least one of R ¹ and R ² is a substituted or unsubstituted fused C3 to C30 cycloalkyl group, in which either is bonded to a neighboring carbon atom of the bonded carbon atom, or a substituted or unsubstituted fused C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group Or at least one of R ³ and R ⁴ is a substituted or unsubstituted fused C3 to C30 cycloalkyl group which is bonded to a neighboring carbon atom of the carbon atom to which one is bonded, a substituted or unsubstituted fused C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

Preferably, the compound represented by Structural Formula 1 may be a compound represented by Structural Formula 2 below.

[Formula 2]

In structure 2,

R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group ego,

R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cyclo Alkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine group, substituted Or an unsubstituted C1 to C30 alkylarylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or Unsubstituted C3 to C30 cycloalkoxy group, substituted or unsubstituted C1 to C30 heterocycloalkoxy group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C1 to C30 hete Roaryloxy group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C3 to C30 cycloalkylthiol group, substituted or unsubstituted C1 to C30 heterocycloalkylthiol group, C6 to C30 arylthiol group, Substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group, or substituted or unsubstituted C1 to C30 heteroarylsilyl group to be.

Also preferably, in Formula 2, R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 To C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine Groups, substituted or unsubstituted C1 to C30 alkoxy groups, or substituted or unsubstituted C1 to C30 alkylthiol groups,

,

,

,

,

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,

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,

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이고,More preferably, R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a C1 to C4 straight chain or a branched alkyl group, a C1 to C4 alkoxy group

,

,

,

,

,

,

,

,

,

,

, or

ego,

n ¹ to n ⁴ are each independently an integer selected from 0 to 4,

이고,X ¹ is nitrogen atom or

ego,

R ³⁹ is a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ¹ is oxygen atom, sulfur atom, or

ego,

Ar ¹ is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or Unsubstituted C1 to C30 heteroaryl group,

Y ² and Y ³ are the same as or different from each other, and each independently an oxygen atom or a sulfur atom,

R ⁵ to R ³⁸ are the same as or different from each other, and each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, It may be a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

Also preferably, in Formula 2, R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 To C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C30 alkylamine Group, a substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C1 to C30 alkylthiol group.

,

,

,

,

,

,

,

,

,

,

, 또는

이고,More preferably, R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a hydroxyl group, a carboxyl group, a C1 to C4 straight chain or a branched alkyl group, a C1 to C4 alkoxy group

,

,

,

,

,

,

,

,

,

,

, or

ego,

n ⁵ to n ⁸ are each independently an integer selected from 0 to 4,

이고,X ² is a nitrogen atom or

ego,

R ⁷⁴ is a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ⁴ is oxygen atom, sulfur atom, or

ego,

Ar ² is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or Unsubstituted C1 to C30 heteroaryl group,

Y ⁵ and Y ⁶ are the same as or different from each other, and each independently an oxygen atom or a sulfur atom,

R ⁴⁰ to R ⁷³ are the same as or different from each other, and each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, It may be a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

Examples of the substituted or unsubstituted C2 to C30 heteroaryl group include substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted thiophenyl group , Substituted or unsubstituted pyrrolyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted imidazo [1,2-a] pyridinyl group, substituted or unsubstituted Benzimidazolyl group, substituted or unsubstituted indazolyl group, substituted or unsubstituted phenothiazinyl group, substituted or unsubstituted phenazinyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzo Thiophenyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl Flag, Cyclic or unsubstituted thiatriazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted purinyl group, substituted or Unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted naphpyridinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted Quinazolinyl group, substituted or unsubstituted acridinyl group, or substituted or unsubstituted phenanthrolinyl group, preferably substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted Triazinyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted already Polyzo [1,2-a] pyridinyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted indazolyl groups, substituted or unsubstituted phenothiazinyl groups, substituted or unsubstituted phenazinyl groups , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

The dicystyryl benzene derivative represented by Formula 2 may be any one selected from Compounds 1 to 125, but the scope of the present invention is not limited thereto.

The present invention also provides a fluorescent material comprising the dicystyryl benzene derivative.

The fluorescent material is any one selected from among fluorescent materials for textile dyes, light emitting materials for organic electroluminescent devices, dye materials for dye-sensitized solar cells, ink materials for ink compositions for electrical / electronic materials, and fluorescent materials for detecting target substances. Although it may be used as, the scope of the present invention is not limited thereto, and may be applied to various industrial fields in which fluorescent materials may be used.

The fluorescent material may be used in textile products such as clothing to which fluorescent dyes are applied.

In addition, the fluorescent material may be applied to an organic light emitting device, a dye-sensitized solar cell, a target material detection device, and various electrical and electronic devices capable of introducing fluorescent material.

EXAMPLE

Hereinafter, the dicystyryl benzene derivative according to the present invention will be described in more detail with reference to Examples. However, this is for illustrative purposes and the scope of the present invention is not limited thereby.

Example  1: Synthesis of Compound 1

Step 1

2,6-dimethyl benzonitrile (10 g, 76.2 mmol), normal-bromosuccinimide (12.074 g, 68.6 mmol) and azobisisobutyronitrile (0.563 g, 3 mmol) were dried over anhydrous chloroform (241.42 mL) After dissolving in, reacted for 4 hours at 65 ° C., extracted with dichloromethane, dried over anhydrous magnesium sulfate, and purified by chromatography using silica gel (SiO 2, n-Hexane: THF = 9: 1) to remove side reactions. To obtain the product.

¹ H NMR (400 MHz, CH ₂ Cl ₂ ) δ 7.50-7.45 (m, 1H), 7.37 (d, J = 7.6 Hz, 1H), 7.30 (d, J = 7.7 Hz, 1H), 4.65 (s, 2H), 2.55 (s, 3H).

Step 2

2- (bromomethyl) -6-methylbenzonitrile (10 g, 47.6 mmol) prepared in Step 1 and an excess of triethylphosphate (40.81 mL, 23.8 mmol) were reacted at 165 ° C. for 24 hours, followed by distillation purification. Excess triethyl phosphate was removed via. Thereafter, the product was obtained by chromatography using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 1: 5).

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.38 (t, J = 7.7 Hz, 1H), 7.30 (dd, J = 7.5, 2.4 Hz, 1H), 7.20-7.14 (m, 1H), 4.14-3.97 ( m, 4H), 3.36 (d, J = 22.3 Hz, 2H), 1.29-1.17 (m, 6H).

Step 3

Terephthalaldehyde (5 g, 37 mmol) and diethyl 2-cyano-3-methylbenzylphosphonate (19.925 g, 74 mmol) prepared in step 2 were dissolved in dimethylformamide (111 mL), followed by hydroxylation. Sodium (4.47 g, 111.8 mmol) was slowly dropped and the temperature was raised to 50 ° C. After 4 hours, the mixture was cooled to room temperature, and then filtered under reduced pressure. The cake was washed with methanol, and the obtained compound was recrystallized with dimethyl sulfoxide. Obtained.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.64 (d, J = 8.0 Hz, 2H), 7.60 (s, 4H), 7.52 (d, J = 16.2 Hz, 2H), 7.46 (t, J = 7.8 Hz , 2H), 7.28 (s, 1H), 7.24 (s, 1H), 7.21 (d, J = 7.5 Hz, 2H), 2.58 (s, 6H).

Example  2: synthesis of compound 2

Step 1

2-methylbenzonitrile (10 g, 85.4 mmol), normal-iodosuccinimide (20.9 g, 93.9 mmol), palladium (II) acetate (0.9 g, 4.3 mmo), para-toluenesulfonic acid monohydrate (8 g , 42.7 mmol) was dissolved in 1,2-dichloroethane (358 mL) and stirred at 70 ° C. for 12 hours. After the completion of the reaction, the reaction product was cooled and chromatographed using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 5: 1) to obtain a product.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.73 (dd, J = 7.3, 1.6 Hz, 1H), 7.30 (dd, J = 7.5, 1.6 Hz, 1H), 7.24 (t, J = 7.4 Hz, 1H) , 2.42 (s, 3 H).

Step 2

2-iodo-6-methylbenzonitrile (10 g, 41.1 mmol), normal-bromosuccinimide (8.69 g, 49.4 mmol) and azobisisobutyronitrile (0.3 g, 1.9 mmol) prepared in step 1 ) Was dissolved in anhydrous chloroform (150 mL), reacted at 65 ° C. for 4 hours, extracted with dichloromethane, dried over anhydrous magnesium sulfate, and chromatography using silica gel (SiO 2, n-Hexane: Ethyl acetate = 3: 1) Purification gave the product.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.80 (dd, J = 7.5, 1.4 Hz, 1H), 7.42 (dd, J = 7.5, 1.6 Hz, 1H), 7.32 (t, J = 7.5 Hz, 1H) , 4.93 (s, 2 H).

Step 3

The 2- (bromo methyl) -6-iodinebenzonitrile (10 g, 31.1 mmol) prepared in Step 2 and an excess of triethylphosphate (26 mL, 15.53 mmol) were reacted at 165 ° C for 24 hours, followed by distillation purification. Excess triethyl phosphate was removed through. After that, the product was purified by chromatography using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 2: 5).

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.75 (dd, J = 7.5, 1.4 Hz, 1H), 7.36 (dd, J = 7.5, 1.6 Hz, 1H), 7.25 (t, J = 7.5 Hz, 1H) , 4.06 (dq, J = 8.5, 5.8 Hz, 4H), 3.05 (d, J = 11.8 Hz, 2H), 1.20 (q, J = 5.7 Hz, 6H).

Step 4

Terephthalaldehyde (5 g, 37 mmol) and diethyl 2-cyano-3-iodobenzylphosphonate (28.27 g, 74 mmol) prepared in step 3 were dissolved in dimethylformamide (111 mL), followed by hydroxylation. Sodium (4.47 g, 111.8 mmol) was slowly dropped and the temperature was raised to 50 ° C. After 4 hours of reaction, the mixture was cooled to room temperature and filtered under reduced pressure. The cake was washed with methanol, and the obtained compound was recrystallized with dimethyl sulfoxide. 2 was obtained.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.74 (dd, J = 7.5, 1.4 Hz, 1H), 7.59 (dd, J = 7.5, 1.4 Hz, 1H), 7.44 (s, 2H), 7.38 (d, J = 15.1 Hz, 1H), 7.31 (t, J = 7.5 Hz, 1H), 7.03 (d, J = 15.1 Hz, 1H).

Example  3: Synthesis of Compound 5

Step 1

Compound 2 (5 g, 8.6 mmol), normal butylboronic acid (1.92 g, 18.8 mmol) and potassium carbonate (7.1 g, 51.4 mmol) in Example 2 were dissolved in toluene anhydride (54.78 mL), followed by [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.626 g, 0.9 mmol) was added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 5.

¹ H NMR (400 MHz, Chloroform) δ 7.54 (t, J = 7.5 Hz, 1H), 7.47 (dd, J = 7.5, 1.6 Hz, 1H), 7.44 (s, 2H), 7.41 (d, J = 15.2 Hz, 1H), 7.25 (dd, J = 7.5, 1.6 Hz, 1H), 7.00 (d, J = 15.1 Hz, 1H), 2.64 (t, J = 7.7 Hz, 2H), 1.68 (p, J = 7.7 Hz, 2H), 1.53-1.33 (m, 2H), 0.99 (t, J = 6.6 Hz, 3H).

Example  4: Synthesis of Compound 7

Step 1

Compound 2 (5 g, 8.6 mmol), normal butylboronic acid (3.238 g, 18.8 mmol) and potassium carbonate (7.1 g, 51.4 mmol) in Example 2 were dissolved in toluene anhydride (54.78 mL), followed by [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.626 g, 0.9 mmol) was added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized with chloroform to obtain Compound 7.

¹ H NMR (400 MHz, Chloroform) δ 8.17-8.13 (m, 1H), 8.10-8.05 (m, 1H), 7.95-7.84 (m, 2H), 7.78-7.69 (m, 3H), 7.66-7.60 ( m, 1H), 7.58-7.50 (m, 3H), 7.45-7.40 (m, 2H), 7.17-7.08 (m, 1H).

Example  5: Synthesis of Compound 10

Step 1

2,5-dibromotoluene (10 g, 40 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL) and slowly dropped normal butyllithium (10 g, 160 mmol) at -78 ° C for 2 hours 30 minutes. Stirring was maintained while maintaining the temperature. Then dimethylformamide (15.5 mL, 200 mmol) was added and stirred for 1 hour. After adding 3 normal hydrochloric acid, anhydrous tetrahydrofuran was removed, extracted with chloroform, dried over anhydrous magnesium sulfate, and purified by chromatography using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 5: 1) to obtain a product. .

¹ H NMR (400 MHz, CDCl ₃ ) δ 10.38 (s, 1H), 10.09 (s, 1H), 7.98 (d, J = 7.8 Hz, 1H), 7.89-7.81 (d, 1H), 7.77-7.72 ( m, 1 H), 2.76 (s, 3 H).

Step 2

An intermediate was obtained by the same synthetic method as Step 2 and Step 3 of Example 1.

Step 3

2-methylterephthalaldehyde (5 g, 33.7 mmol) prepared in step 1 and diethyl 2-cyano-3-methylbenzylphosphonate (18 g, 67.5 mmol) dimethylformamide (101 mL) prepared in step 2 Sodium hydroxide (4 g, 101 mmol) was slowly added to the mixture, and then heated up to 50 ° C., reacted for 4 hours, cooled to room temperature, filtered under reduced pressure, the cake was washed with methanol, and the obtained compound was diluted with dimethyl sulfoxy. Recrystallization gave 10 to give compound 10.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.72-7.69 (m, 1H), 7.65-7.60 (m, 2H), 7.45 (d, J = 20.8 Hz, 7H), 7.25-7.18 (m, 3H), 2.58 (s, 6 H), 2.50 (s, 3 H).

Example  6: Synthesis of Compound 11

Step 1

2-bromo-1,4-dimethylbenzene (10 g, 54 mmol) was dissolved in acetic acid (65 mL) and acetic anhydride (130 mL) at 0-5 ° C., followed by dropping sulfuric acid (48 mL). Chromium trioxide (17.29 g, 172 mmol) was added to the mixture while maintaining the temperature. After the reaction for 5 hours, the green mixture was poured into iced water (1000 mL), extracted with chloroform, the organic layer was washed with an aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilled water (70 mL), ethanol (70 mL), sulfuric acid (7 mL) was added to the mixture was heated for 5 hours. The mixture was then cooled to room temperature, distilled water (500 mL) was added, extracted with chloroform, dried over anhydrous magnesium sulfate, and purified by chromatography on silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 4: 1). The product was obtained.

¹ H NMR (400 MHz, CDCl ₃ ) δ 10.44 (s, 1H), 10.06 (s, 1H), 8.16 (d, J = 1.4 Hz, 1H), 8.07 (d, J = 7.9 Hz, 1H), 7.96 7.90 (m, 1 H).

Step 2

2-methylbenzonitrile (10 g, 85.4 mmol), normal-bromosuccinimide (16.52 g, 94 mmol) and azobisisobutyronitrile (0.63 g, 3.8 mmol) were dissolved in anhydrous chloroform (256 mL). After reacting at 65 ° C. for 4 hours, the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and the reaction product was removed by chromatography using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 4: 1). Got.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.68 (d, J = 7.8 Hz, 1H), 7.62-7.57 (m, 1H), 7.56 (d, J = 7.7 Hz, 1H), 7.46-7.40 (m, 1H), 4.64 (s, 2H).

Step 3

The 2- (bromomethyl) benzonitrile (10 g, 51 mmol) prepared in Step 2 was reacted with an excess of triethylphosphate (44 mL, 25.5 mmol) at 165 ° C for 24 hours, and then the excess tree was purified through distillation purification. Ethyl phosphate was removed. The product was obtained by chromatography using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 2: 2).

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.67-7.62 (m, 1H), 7.58-7.50 (m, 2H), 7.40-7.31 (m, 1H), 4.14-4.01 (m, 4H), 3.40 (d , J = 22.3 Hz, 2H), 1.26 (q, J = 7.0 Hz, 6H).

Step 4

2-bromoterephthalaldehyde (5 g, 23.5 mmol) prepared in step 1, 2-cyanobenzylphosphonate (12 g, 46.9 mmol) prepared in step 3 was dissolved in dimethylformamide (70 mL). After slowly dropping sodium hydroxide (2.8 g, 70.4 mmol), the mixture was heated up to 50 ° C, cooled at room temperature for 4 hours, and then filtered under reduced pressure to wash the cake-like compound with methanol, and the compound was recrystallized with dimethyl sulfoxide. Compound 11 was obtained.

¹ H NMR (400 MHz, DMSO) δ 8.02 (dd, J = 8.0, 2.7 Hz, 9H), 8.00 (d, J = 1.4 Hz, 5H), 7.96 (d, J = 8.2 Hz, 5H), 7.90 ( t, J = 8.2 Hz, 10H), 7.81-7.74 (m, 15H), 7.68 (d, J = 16.1 Hz, 5H), 7.60-7.55 (m, 3H), 7.55-7.48 (m, 16H), 7.45 (d, J = 16.1 Hz, 6H).

Example  7: Synthesis of Compound 14

Compound 11 (5 g, 12.16 mmol), naphthalene-1-ylboronic acid (2.3 g, 13.37 mmol) and potassium carbonate (5.041 g, 36.47 mmol) of Example 6 were dissolved in toluene anhydrous (51.06 mL), 1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.445 g, 0.61 mmol) was added thereto, and the temperature was increased to 120 ° C. After the reaction for 2 hours, the mixture was cooled to room temperature, the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to prepare Compound 14.

¹ H NMR (400 MHz, Chloroform) δ 7.83 (d, J = 1.4 Hz, 1H), 7.82-7.79 (m, 1H), 7.78-7.74 (m, 1H), 7.72 (dd, J = 6.9, 2.0 Hz , 1H), 7.61 (d, J = 7.5 Hz, 1H), 7.57 (td, J = 6.4, 3.1 Hz, 3H), 7.85-6.77 (m, 22H), 7.54-7.39 (m, 7H), 7.39- 7.24 (m, 5H), 7.16 (d, J = 15.2 Hz, 1H), 7.14 (dd, J = 19.5, 15.2 Hz, 2H), 7.14 (dd, J = 19.5, 15.2 Hz, 2H), 7.11 (d , J = 15.2 Hz, 1H).

Example  8: Synthesis of Compound 16

Step 1

Compound 11 (5 g, 12.16 mmol), isobutylboronic acid (1.363 g, 13.37 mmol) and potassium carbonate (5.04 g, 36.47 mmol) in Example 6 were dissolved in toluene anhydride (51.06 mL), and then [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.445 g, 0.61 mmol) was added thereto, and the temperature was increased to 120 ° C. After the reaction for 2 hours, the mixture was cooled to room temperature, the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 16.

¹ H NMR (400 MHz, Chloroform) δ 7.63 (d, J = 0.4 Hz, 2H), 7.60 (d, J = 1.4 Hz, 2H), 7.53 (t, J = 10.6 Hz, 3H), 7.41 (s, 1H), 7.32 (t, J = 10.3 Hz, 3H), 7.22 (s, 1H), 7.16 (d, J = 3.9 Hz, 1H), 7.14 (s, 2H), 2.72-2.65 (m, 2H), 2.23 (s, 1 H), 1.10-1.03 (m, 6 H).

Example  9: Synthesis of Compound 17

Step 1

Terephthalaldehyde (10 g, 74.5 mmol), 1-chloro-4-methylbenzene (9 mL, 74.5 mmol) dissolved in anhydrous 1,4-dioxane (213 mL), and then palladium (II) acetate (0.167 g, 0.75 mmol) ), 1,3-bis (1-adamantyl) imidazolium chloride (0.056 g, 0.15 mmol) and cesium carbonate (48 g, 149 mmol) were added thereto, reacted at 80 ° C. for 16 hours, and extracted with dichloromethane. After drying over anhydrous magnesium sulfate, the product was purified by chromatography using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 3: 1).

¹ H NMR (400 MHz, CDCl ₃ ) δ 10.12 (s, 1H), 9.95 (s, 1H), 8.41 (d, J = 1.4 Hz, 1H), 8.18 (d, J = 7.5 Hz, 1H), 8.06 (dd, J = 7.5, 1.4 Hz, 1H), 7.59 (d, J = 7.4 Hz, 2H), 7.34 (d, J = 7.4 Hz, 2H), 2.36 (s, 3H).

Step 2

An intermediate was obtained in the same manner as in Step 2 and Step 3 in Example 6.

Step 3

4'-methyl- [1,1'-biphenyl] -2,5-dicarbaldehyde (5 g, 22.3 mmol) prepared in step 1 and example 2 prepared in step 2, step 3 of compound 1 -Cyanobenzylphosphonate (12 g, 49.1 mmol) was slowly added dropwise sodium hydroxide (2.7 g, 66.9 mmol) to dimethylformamide (71.35 mL), and then heated up to 50 ℃ and cooled at room temperature after 4 hours reaction After washing under reduced pressure, the cake-like compound was washed with methanol, and the obtained compound was recrystallized with dimethyl sulfoxide to obtain compound 17.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.85 (s, 3H), 7.66-7.51 (m, 29H), 7.48 (s, 4H), 7.39 (s, 3H), 7.33 (dd, J = 9.2, 1.4 Hz, 12H), 7.22 (s, 3H), 7.17 (s, 3H), 2.41-2.30 (m, 9H).

Example  10: Synthesis of Compound 18

Step 1

2-chloro-1,4-dimethyl benzene (10 g, 71.1 mmol) was dissolved in acetic acid (85 mL) and acetic anhydride (170 mL) at 0 ~ 5 ° C, and then sulfuric acid (63.2 mL) was dropped, and then the temperature was decreased. Chromium trioxide (22.759 g, 228 mmol) was added to the mixture while maintaining the same. After the reaction for 5 hours, the green mixture was poured into iced water (1000 mL), extracted with chloroform, the organic layer was washed with an aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilled water (70 mL), ethanol (70 mL), sulfuric acid (7 mL) was added to the mixture was heated for 5 hours. The mixture was then cooled to room temperature, distilled water (500 mL) was added, extracted with chloroform, dried over anhydrous magnesium sulfate, and chromatographed using silica gel (SiO ₂ , n-Hexane: Ethyl acetate = 4: 1). The product was obtained through.

¹ H NMR (400 MHz, CDCl ₃ ) δ 10.55 (s, 1H), 10.07 (s, 1H), 8.09 (d, J = 7.9 Hz, 1H), 7.97 (d, J = 1.4 Hz, 1H), 7.91 7.85 (m, 1 H).

Step 2

In the same manner as in Step 2 and Step 3 in Example 6, an intermediate was obtained.

Step 3

2-chloroterephthalaldehyde (5 g, 29.7 mmol) prepared in step 1, Example 6 2-cyanobenzylphosphonate (15 g, 59.3 mmol) prepared in step 2, step 3 in the preparation of compound 11 After dissolving in formamide (89 mL), sodium hydroxide (3.56 g, 89 mmol) was slowly dropped, and then heated up to 50 ° C, cooled at room temperature for 4 hours, and then filtered under reduced pressure to wash the cake-like compound with methanol. The compound was recrystallized from dimethyl sulfoxide to give compound 18.

¹ H NMR (400 MHz, DMSO) δ 8.03 (t, J = 7.3 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.89 (t, J = 7.6 Hz, 2H), 7.83 (d, J = 1.5 Hz, 1H), 7.80-7.69 (m, 4H), 7.60-7.45 (m, 5H).

Example  11: Synthesis of Compound 21

Step 1

An intermediate was obtained in the same manner as in Step 2 and Step 3 in Example 3.

Step 2

2,5-dibromoterephthalaldehyde (5 g, 17.1 mmol), 2-cyanobenzylphosphonate (8.675 g, 34.3 mmol) prepared in step 1 was dissolved in dimethylformamide (51 mL), followed by hydroxylation. After slowly dropping sodium (2 g, 51.4 mmol), the temperature was raised to 50 ° C., the reaction mixture was cooled to room temperature, and then cooled at room temperature. The mixture was filtered under reduced pressure to wash the cake-like compound with methanol, and the compound was recrystallized from dimethyl sulfoxide. Obtained.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.68-7.60 (m, 3H), 7.55 (td, J = 7.5, 1.4 Hz, 1H), 7.35 (td, J = 7.5, 1.4 Hz, 1H), 7.29 ( d, J = 15.1 Hz, 1H), 7.22 (d, J = 14.9 Hz, 1H).

Example  12: Synthesis of Compound 23

Compound 21 (5 g, 10.20 mmol), isobutylboronic acid (2.29 g, 22.44 mmol) and potassium carbonate (8.459 g, 61.2 mmol) in Example 11 were dissolved in toluene (65.28 mL), followed by [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.746 g, 1.02 mmol) was added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 23.

¹ H NMR (400 MHz, Chloroform) δ 7.61 (ddd, J = 7.5, 6.2, 1.5 Hz, 2H), 7.54 (td, J = 7.4, 1.5 Hz, 1H), 7.42 (s, 1H), 7.34 (td , J = 7.3, 1.6 Hz, 1H), 7.29-7.18 (m, 2H), 2.58 (d, J = 7.5 Hz, 2H), 2.25-2.05 (m, 1H), 1.05 (d, J = 6.3 Hz, 6H).

Example  13: Synthesis of Compound 24

Compound 21 (5 g, 10.20 mmol), naphthalene-1-ylboronic acid (3.86 g, 22.44 mmol) and potassium carbonate (8.459 g, 61.2 mmol) in Example 11 were dissolved in toluene (65.28 mL), [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.746 g, 1.02 mmol) was added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 24.

¹ H NMR (400 MHz, Chloroform) δ 8.11 (s, 1H), 7.96-7.91 (m, 1H), 7.91-7.87 (m, 1H), 7.86 (dd, J = 7.1, 1.8 Hz, 1H), 7.63 7.58 (m, 2H), 7.57 (d, J = 4.8 Hz, 2H), 7.52 (td, J = 7.4, 1.4 Hz, 1H), 7.50-7.41 (m, 3H), 7.33 (td, J = 7.6 , 1.7 Hz, 1H), 7.28 (d, J = 14.9 Hz, 1H).

Example  14: Synthesis of Compound 26

Compound 21 (5 g, 10.20 mmol), (3-aminophenyl) boronic acid (3.86 g, 22.44 mmol) and potassium carbonate (8.459 g, 61.2 mmol) in Example 11 were dissolved in anhydrous toluene (65.28 mL). , [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.746 g, 1.02 mmol) were added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized with chloroform to obtain Compound 26.

¹ H NMR (400 MHz, Chloroform) δ 8.06 (s, 1H), 7.62 (ddd, J = 7.4, 4.3, 1.5 Hz, 2H), 7.54 (td, J = 7.5, 1.5 Hz, 1H), 7.39-7.25 (m, 3H), 7.15 (d, J = 14.9 Hz, 1H), 7.09 (dt, J = 7.7, 1.5 Hz, 1H), 6.99 (t, J = 1.5 Hz, 1H), 6.70 (dt, J = 7.5, 1.4 Hz, 1H), 3.94 (s, 2H).

Example  15: Synthesis of Compound 27

Compound 2 (5 g, 8.6 mmol), (3-aminophenyl) boronic acid (2.58 g, 18.8 mmol) and potassium carbonate (7.1 g, 51.4 mmol) in Example 2 were dissolved in toluene anhydride (54.78 mL) , [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.626 g, 0.9 mmol) were added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 27.

¹ H NMR (400 MHz, Chloroform) δ 7.77-7.64 (m, 3H), 7.53 (d, J = 15.1 Hz, 1H), 7.45 (s, 2H), 7.25 (t, J = 7.5 Hz, 1H), 7.16 (d, J = 15.1 Hz, 1H), 7.06 (dt, J = 7.5, 1.4 Hz, 1H), 6.97 (t, J = 1.4 Hz, 1H), 6.67 (dt, J = 7.5, 1.5 Hz, 1H ), 3.89 (s, 2 H).

Example  16: Synthesis of Compound 28

Compound 11 (5 g, 12.16 mmol), (3-aminophenyl) boronic acid (1.831 g, 13.37 mmol) and potassium carbonate (5.04 g, 36.47 mmol) of Example 6 were dissolved in toluene (51.06 mL) , [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.445 g, 0.61 mmol) were added thereto, and the temperature was increased to 120 ° C. After the reaction for 2 hours, the mixture was cooled to room temperature, the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 28.

¹ H NMR (400 MHz, Chloroform) δ 7.88 (s, 2H), 7.60 (ddd, J = 25.8, 9.8, 6.0 Hz, 16H), 7.42 (s, 2H), 7.35 (d, J = 2.6 Hz, 4H ), 7.28 (d, J = 8.1 Hz, 3H), 7.15-7.04 (m, 6H), 6.98 (s, 2H), 6.70 (s, 2H), 4.00-3.85 (m, 4H).

Example  17: compound 31 synthesis

Step 1

Example 2 An intermediate was obtained in the same manner as in steps 1, 2 and 3 in the synthesis of compound 2.

Step 2

2,5-dibromoterephthalaldehyde (5 g, 17.1 mmol) and diethyl 2-cyano-3-iodo benzylphosphonate (13 g, 34.3 mmol) prepared in step 1 were added to dimethylformamide (51.38). mL) and then slowly drop the sodium hydroxide (2.05 g, 51.4 mmol), and then the temperature was raised to 50 ℃, after 4 hours the reaction was cooled to room temperature, and then filtered under reduced pressure to wash the cake-like compound with methanol and the obtained compound was dimethyl Recrystallization with sulfoxide gave compound 31.

¹ H NMR (400 MHz, Chloroform) δ 7.74 (dd, J = 7.5, 1.4 Hz, 2H), 7.60 (d, J = 1.6 Hz, 1H), 7.59 (s, 2H), 7.58 (d, J = 1.4 Hz, 1H), 7.33 (d, J = 7.6 Hz, 2H), 7.29 (s, 4H).

Example  18: Synthesis of Compound 32

Step 1

An intermediate was obtained in the same manner as in Step 1 of Example 5.

Step 2

An intermediate was obtained in the same manner as in Step 1, Step 2, and Step 3 of Example 2.

Step 3

2-bromo terephthalaldehyde (5 g, 23.5 mmol) in step 1 and diethyl 2-cyano-3-iodobenzylphosphonate (17.78 g, 46.9 mmol) in step 2 were diluted with dimethylformamide (70.41 mL). After dissolving in sodium hydroxide (2.82 g, 70.4 mmol) was slowly dropped, the temperature was raised to 50 ℃, after 4 hours the reaction was cooled to room temperature, and then filtered under reduced pressure to wash the cake-like compound with methanol and the obtained compound was dimethyl sulfoxy Recrystallization gave Compound 32.

¹ H NMR (400 MHz, Chloroform) δ 7.74 (dd, J = 7.5, 1.4 Hz, 2H), 7.65 (d, J = 1.4 Hz, 1H), 7.61 (ddd, J = 7.4, 3.9, 1.4 Hz, 2H ), 7.49-7.41 (m, 2H), 7.40-7.26 (m, 5H), 7.11 (d, J = 15.1 Hz, 1H).

Example  19: Synthesis of Compound 33

Step 1

An intermediate was obtained in the same manner as in Step 2 and Step 3 in Example 6.

Step 2

An intermediate was obtained in the same manner as in Step 1, Step 2, and Step 3 of Example 2.

Step 3

2,5-dibromoterephthalaldehyde (5 g, 17.1 mmol), 2-cyano benzylphosphonate (6.49 g, 17.1 mmol) prepared in step 1 and diethyl 2-cyano- prepared in step 2 3-Iodobenzylphosphonate (4.38 g, 17.1 mmol) was dissolved in dimethylformamide (51.38 mL), and sodium hydroxide (2.05 g, 51.4 mmol) was slowly dropped, and the temperature was raised to 50 ° C. and after 4 hours of reaction. After cooling at room temperature, the product was filtered under reduced pressure to wash the cake-like compound with methanol, and the obtained compound was recrystallized with dimethyl sulfoxide to obtain Compound 33.

¹ H NMR (400 MHz, Chloroform) δ 7.74 (dd, J = 7.5, 1.4 Hz, 1H), 7.63 (s, 1H), 7.61 (dt, J = 7.4, 1.7 Hz, 2H), 7.59-7.52 (m , 3H), 7.37-7.23 (m, 6H).

Example  20: Synthesis of Compound 34

Step 1

An intermediate was obtained in the same manner as in Step 1 in Example 6.

Step 2

An intermediate was obtained in the same manner as in Step 2 and Step 3 in Example 6.

Step 3

An intermediate was obtained in the same manner as in Step 1, Step 2, and Step 3 of Example 2.

Step 4

2-bromoterephthalaldehyde (5 g, 23.5 mmol) prepared in step 1, 2-cyanobenzylphosphonate (9 g, 23.5 mmol) prepared in step 2 and diethyl 2-cya prepared in step 3 No-3-iodobenzylphosphonate (6 g, 23.5 mmol) was dissolved in dimethylformamide (70.41 mL), and sodium hydroxide (2.82 g, 70.4 mmol) was slowly dropped, and the temperature was raised to 50 ° C. and 4 hours. After the reaction, the mixture was cooled to room temperature, filtered under reduced pressure to wash the cake-like compound with methanol, and the obtained compound was recrystallized from dimethyl sulfoxide to obtain Compound 34.

¹ H NMR (400 MHz, Chloroform) δ 7.74 (dd, J = 7.6, 1.5 Hz, 1H), 7.66-7.59 (m, 4H), 7.56 (td, J = 7.4, 1.4 Hz, 1H), 7.47 (d , J = 15.2 Hz, 1H), 7.43 (dd, J = 7.5, 1.4 Hz, 1H), 7.42-7.26 (m, 5H), 7.11 (d, J = 15.1 Hz, 1H).

Example  21: Synthesis of Compound 35

Compound 32 (5 g, 7.54 mmol), (3-aminophenyl) boronic acid (3.41 g, 24.9 mmol) and potassium carbonate (9.4 g, 67.86 mmol) were dissolved in toluene anhydride (64.85 mL) and then [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (0.828 g, 1.13 mmol) was added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 35.

¹ H NMR (400 MHz, Chloroform) δ 7.84 (d, J = 1.3 Hz, 1H), 7.75-7.70 (m, 3H), 7.67 (ddd, J = 6.6, 4.8, 2.6 Hz, 3H), 7.61 (d , J = 7.7 Hz, 1H), 7.59 (dd, J = 7.6, 1.2 Hz, 1H), 7.46 (d, J = 15.1 Hz, 1H), 7.30-7.20 (m, 4H), 7.13 (d, J = 15.2 Hz, 1H), 7.10-7.06 (m, 2H), 7.04 (dt, J = 7.5, 1.5 Hz, 2H), 7.00 (t, J = 1.4 Hz, 1H), 6.96 (t, J = 1.3 Hz, 2H), 6.71-6.63 (m, 3H), 4.20 (s, 2H), 3.90 (s, 4H).

Example  22: Synthesis of Compound 42

Compound 32 (5 g, 7.54 mmol), cyclohexylboronic acid (4.246 g, 33.18 mmol) and potassium carbonate (12.5 g, 90.49 mmol) were dissolved in toluene anhydride (81.44 mL) and then [1,1'-bis (Diphenylphosphino) ferrocene] palladium (II) dichloride catalyst (1.1 g, 1.5 mmol) was added thereto, and the temperature was increased to 120 ° C. After reacting for 2 hours, the mixture was cooled to room temperature, and then the solvent was removed, washed with methanol, and the obtained compound was recrystallized from chloroform to obtain Compound 42.

¹ H NMR (400 MHz, Chloroform) δ 7.57-7.52 (m, 4H), 7.52-7.47 (m, 2H), 7.39-7.34 (m, 2H), 7.26-7.19 (m, 2H), 7.17-7.11 ( m, 2H), 3.27 (s, 1H), 3.13 (s, 1H), 2.69-2.54 (m, 2H), 2.25-2.08 (m, 8H), 1.78-1.62 (m, 20H), 1.47-1.30 ( m, 12H).

Comparative example  1: Synthesis of Comparative Compound

Step 1

An intermediate was obtained in the same manner as in Step 2 and Step 3 in Example 3.

Step 2

Terephthalaldehyde (5 g, 37.3 mmol), 2-cyanobenzylphosphonate (18.88 g, 74.6 mmol) prepared in step 1 was dissolved in dimethylformamide (111.85 mL), followed by sodium hydroxide (4.47 g, 111.8 mmol ) Was slowly dropped, and then heated up to 50 ° C., cooled at room temperature after 4 hours of reaction, and filtered under reduced pressure to wash the cake-like compound with methanol to recrystallize the compound with dimethyl sulfoxide to prepare a comparative compound.

¹ H NMR (400 MHz, CDCl ₃ ) δ 7.82 (d, J = 8.0 Hz, 1H), 7.67 (dd, J = 7.8, 1.0 Hz, 1H), 7.61 (s, 2H), 7.59 (d, J = 7.7 Hz, 1H), 7.50 (d, J = 16.2 Hz, 1H), 7.35 (td, J = 7.6, 0.9 Hz, 1H), 7.29 (d, J = 16.2 Hz, 1H).

[Test Example]

Emission characteristics

The luminescence quantum efficiency (ΦF (A)) of the sample (A) to be analyzed is the diacyanstyryl benzene prepared according to Comparative Example 1 and the UV absorbance (A), PL of the compounds 1, 10, 17, 18 and 21. (Photoluminescence) intensity (area) and refractive index (η) of the solvent were substituted and calculated. That is, the luminescence properties were analyzed by comparing the relative PL intensity with respect to the absorbance A value related to the concentration regardless of the concentration of specific materials.

 [expression]

Results of light emission characteristics analysis are shown in Table 1 and FIG. 1.

division Relative quantum efficiency
(PLQY) UV (absorption) PL (area) PL (strength) Comparative Compound 1.00 1.1696 1436400 19670.84 Compound 1 5.09 0.1797 1122294 15083.02 Compound 5 1.87 0.8251 1892105 23221.62 Compound 7 3.91 0.9189 4414981 48521.18 Compound 9 0.95 0.9495 1102821 14942.46 Compound 10 3.66 0.3154 1417284 19116.61 Compound 17 1.09 0.9051 1211981 20981.79 Compound 18 2.12 0.9906 2574984 35190.20 Compound 21 1.40 0.9557 1646578 22604.14 Compound 27 3.63 0.8516 3797862 41982.91 Compound 42 1.97 0.9105 2199876 26181.13

Accordingly, the luminescence intensity was analyzed by comparing the compounds for fluorescent materials under similar concentration conditions with those of Comparative Example 1, except that Compound 1 of the present invention was substituted with Compound 17. 5, 7, 9, 10, 18, 21, 27 and 42 showed relatively higher fluorescence yields than the comparative compounds. In particular, in the case of Compound 1 substituted with two methyl groups, the emission intensity was remarkably increased more than five times than that of the comparative compound. These results indicate that the fluorescent dye compound of the present invention can exhibit the same fluorescence brightening properties while using a relatively small amount, and thus is a very advantageous new material in terms of environment or economy.

Claims (11)

Dicystyryl benzene derivative, characterized in that represented by the following formula (2).
[Formula 2]

In structure 2,
R ¹ and R ² are not hydrogen atoms at the same time, R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 A cycloalkyl group or a substituted or unsubstituted C6 to C30 aryl group,
R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C6 to C30 It is an aryl group. delete delete The method of claim 1,
R ¹ and R ² are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a C1 to C4 straight chain or a branched alkyl group,

,

,

,

,

, or

R ¹ and R ² are not a hydrogen atom at the same time,
X ¹ is

ego,
R ³⁹ is a hydrogen atom or a substituted or unsubstituted C 1 to C 30 alkyl group,
R ⁵ to R ⁹ , R ¹⁷ to R ²⁰ , and R ²⁸ to R ³⁶ , which are the same as or different from each other, are each independently hydrogen atoms or substituted or unsubstituted C 1 to C 30 alkyl groups, which are dicystyryls Benzene derivatives. delete The method of claim 1,
R ³ and R ⁴ are the same as or different from each other, and each independently a hydrogen atom, a halogen group, a C1 to C4 straight chain or a branched alkyl group,

,

,

,

,

, or

ego,
X ² is

ego,
R ⁷⁴ is a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,
R ⁴⁰ to R ⁴⁴ , R ⁵² to R ⁵⁵ , and R ⁶⁵ to R ⁷¹ are the same as or different from each other, and are each independently a hydrogen atom or a substituted or unsubstituted C 1 to C 30 alkyl group Benzene derivatives. Dicystyryl benzene derivative any one selected from compound 1 to 8, 10, 12 to 14, 17, 20, 21, 24, 25 to 104, and 106 to 125.

A fluorescent material comprising any one of dicystyryl benzene derivatives selected from claims 1, 4, 6 and 7. The method of claim 8,
The fluorescent material is any one selected from among fluorescent materials for textile dyes, light emitting materials for organic electroluminescent devices, dye materials for dye-sensitized solar cells, ink materials for ink compositions for electrical / electronic materials, and fluorescent materials for detecting target substances. Fluorescent material, characterized in that used as. A textile product comprising the fluorescent material of claim 8. An electric or electronic device comprising the fluorescent material of claim 8.

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