JP2018002630A - Photopolymerization sensitizer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel photopolymerization sensitizer that does not use alkylene oxide, which is poorly available, in synthesis, and prevents the occurrence of migration during storage.SOLUTION: The present invention provides a 10-bis(2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by formula (1).SELECTED DRAWING: None

Description

The present invention relates to a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound, a production method thereof and a photopolymerization sensitizer.

Photo-curing resins that are polymerized by active energy rays such as ultraviolet rays and visible rays cure quickly and can significantly reduce the amount of organic solvent used compared to thermosetting resins. It is excellent in that it can be reduced. Conventional photocurable resins themselves have a poor polymerization initiating function, and it is usually necessary to use a photopolymerization initiator for curing. As the photopolymerization initiator, alkylphenone-based polymerization initiators such as hydroxyacetophenone and benzophenone, acylphosphine oxide-based photopolymerization initiators, or onium salts are used (Patent Documents 1, 2, and 3). Among these photopolymerization initiators, when an onium salt-based initiator is used, the light absorption of the onium salt is in the vicinity of 225 nm to 350 nm and does not absorb at 350 nm or more. Therefore, a long wavelength lamp of 350 nm or more is used as a light source. In such a case, there is a problem that the photocuring reaction does not easily proceed, and a photopolymerization sensitizer is generally added. Anthracene and thioxanthone compounds are known as photopolymerization sensitizers, and anthracene compounds are particularly often used due to color problems (Patent Document 4).

As an anthracene photopolymerization sensitizer, a 9,10-dialkoxyanthracene compound is used. For example, a 9,10-dialkoxyanthracene compound such as 9,10-dibutoxyanthracene or 9,10-diethoxyanthracene is used as a photopolymerization sensitizer for an iodonium salt that is a photopolymerization initiator in photopolymerization. (Patent Documents 5, 6, 7, and 8).

However, the 9,10-dialkoxyanthracene compound may cause problems such as powdering of the cured product and coloring due to blooming during photocuring or storage of the cured product due to blooming. Are known. For example, when these photopolymerization sensitizers are used as a component of a photoadhesive that bonds the film to the film, the photopolymerization sensitizer may migrate to the film overlaid (migration). On top of this, it may cause problems with powdering and coloring of the photopolymerization sensitizer. In order to suppress migration of such a photopolymerization sensitizer, a 9,10-bis (2-acyloxyalkoxy) anthracene compound in which an ester group which is a polar group is introduced into an alkoxy group of a 9,10-dialkoxyanthracene compound is It has been reported (Patent Document 9).

However, the 9,10-bis (2-acyloxyalkoxy) anthracene compound has a step of using an alkylene oxide compound at the time of production, and the 9,10-bis is difficult to obtain and handle the alkylene oxide compound, particularly ethylene oxide. This is a serious problem in the production of bis (2-acyloxyalkoxy) anthracene compounds.

Japanese Patent Laid-Open No. 06-345614 Japanese Patent Application Laid-Open No. 07-062010 JP 05-249606 A JP-A-10-195117 JP 2002-302507 A JP 11-279212 A JP 2000-344704 A WO2007 / 126066 JP 2014-031346 A

Therefore, it is desired to develop a photopolymerization sensitizer that does not easily cause blooming or migration during storage without using an alkylene oxide compound that is difficult to obtain in the production process.

As a result of further intensive studies on the structure and physical properties of the anthracene compound, the present inventors have found that the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention is difficult to obtain in the production process. The photopolymerizable composition can be produced using a glycidyl ether compound that is generally easy to handle and does not require the use of alkylene, and exhibits an excellent effect as a photopolymerization sensitizer in a photopolymerization reaction. The present inventors have found that the photopolymerization sensitizer is less likely to cause migration or the like even when a film is placed on the substrate, and the present invention has been completed.

That is, the first gist of the present invention resides in a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (1).

(In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents 1 to 8 carbon atoms. X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.)

The second gist of the present invention is that acylation is performed by reacting a 9,10-bis (2-hydroxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (2) with an acylating agent. The present invention resides in a method for producing a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (1).

The 3rd summary of this invention exists in the photopolymerizable composition containing the photoinitiator composition as described in a 2nd summary, and a photopolymerizable compound.

(In General Formula (2), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and X and Y are the same. May be different, and represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.)

(In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents 1 to 8 carbon atoms. X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.)

The third gist of the present invention resides in a photopolymerization sensitizer containing a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (1).

(In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents 1 to 8 carbon atoms. X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.)

The fourth gist of the present invention resides in a photopolymerization initiator composition containing the photopolymerization sensitizer described in the third gist and a photopolymerization initiator.

The fifth gist of the present invention resides in a photopolymerizable composition containing the photopolymerization initiator composition described in the fourth gist and a photopolymerizable compound.

The sixth gist of the present invention resides in a curing method in which the photopolymerizable composition described in the fifth gist is cured by irradiating with an energy ray containing light having a wavelength in the range of 250 nm to 500 nm.

The 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention not only has a high effect as a photopolymerization sensitizer in the photopolymerization reaction but also photopolymerizes the compound of the present invention. When a film is put on a photopolymerizable composition contained as a sensitizer, the compound of the present invention is a useful compound that has a very low migration property to a coating film. Furthermore, the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention can be obtained by using a more general glycidyl ether compound without using an alkylene oxide which is difficult to obtain at the time of production. It can be synthesized. Further, the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention obtained is a liquid at room temperature, such as 9,10-bis (2-hydroxy-3-substituted oxy). Propoxy) has an excellent characteristic such that the melting point is lower than that of anthracene compound, and as a result, the solubility in the polymerizable compound is remarkably improved.

(Compound)
The 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention is a compound represented by the following general formula (1).

In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents one having 1 to 8 carbon atoms. It represents either an alkyl group or an aryl group, and X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.

In the general formula (1), the alkoxymethyl group having 1 to 5 carbon atoms represented by A includes a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, a butoxymethyl group, a pentyloxymethyl group, allyl An oxymethyl group etc. are mentioned. Examples of the aryloxymethyl group having an aryl group having 6 to 10 carbon atoms include phenoxymethyl group, tolyloxymethyl group, 1-naphthyloxymethyl group, and 2-naphthyloxymethyl group.

In the general formula (1), examples of the alkyl group having 1 to 8 carbon atoms represented by B include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, n -Pentyl group, i-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group and the like can be mentioned. As the aryl group, phenyl group, tolyl group, naphthyl group and the like can be mentioned. .

In the general formula (1), the alkyl group having 1 to 8 carbon atoms represented by X or Y includes a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and an i-butyl group. , T-butyl group, n-pentyl group, i-pentyl group, n-hexyl group, n-heptyl group, n-octyl group or 2-ethylhexyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

As a specific example of the 9,10-bis (2-acyloxy-3-substituted propoxy) anthracene compound represented by the general formula (1) of the present invention, X and Y are hydrogen atoms, and B is a methyl group. In some cases, for example, 9,10-bis (2-acetoxy-3-methoxypropoxy) anthracene, 9,10-bis (2-acetoxy-3-ethoxypropoxy) anthracene, 9,10-bis [2-acetoxy- 3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene, 9,10-bis [2-acetoxy-3- (n-pentyloxy) Propoxy] anthracene, 9,10-bis [2-acetoxy-3- (n-hexyloxy) propoxy] anthracene, 9,10-bis 2-acetoxy-3- (n-heptyloxy) propoxy] anthracene, 9,10-bis [2-acetoxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-acetoxy-3- (2-Ethylhexyloxy) propoxy] anthracene, 9,10-bis (2-acetoxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-acetoxy-3-methallyloxypropoxy) anthracene, 9,10 -Bis (2-acetoxy-3-phenoxypropoxy) anthracene, 9,10-bis (2-acetoxy-3-tolyloxypropoxy) anthracene, 9,10-bis (2-acetoxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Examples of the case where X and Y are hydrogen atoms and B is an ethyl group include, for example, 9,10-bis (2-propionyloxy-3-methoxypropoxy) anthracene, 9,10-bis (2-propionyloxy- 3-Ethoxypropoxy) anthracene, 9,10-bis [2-propionyloxy-3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene 9,10-bis [2-propionyloxy-3- (n-pentyloxy) propoxy] anthracene, 9,10-bis [2-propionyloxy-3- (n-hexyloxy) propoxy] anthracene, 9,10 -Bis [2-propionyloxy-3- (n-heptyloxy) propoxy] anthra 9,10-bis [2-propionyloxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-propionyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 9, 10-bis (2-propionyloxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-propionyloxy-3-methallyloxypropoxy) anthracene, 9,10-bis (2-propionyloxy-3-) Phenoxypropoxy) anthracene, 9,10-bis (2-propionyloxy-3-tolyloxypropoxy) anthracene, 9,10-bis (2-propionyloxy-3-naphthyloxypropoxy) anthracene and the like.

Examples of the case where X and Y are hydrogen atoms and B is a propyl group include, for example, 9,10-bis (2-butyryloxy-3-methoxypropoxy) anthracene, 9,10-bis (2-butyryloxy-3-). Ethoxypropoxy) anthracene, 9,10-bis [2-butyryloxy-3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene, 9,10 -Bis [2-butyryloxy-3- (n-pentyloxy) propoxy] anthracene, 9,10-bis [2-butyryloxy-3- (n-hexyloxy) propoxy] anthracene, 9,10-bis [2-butyryloxy -3- (n-heptyloxy) propoxy] anthracene, 9,10-bis [2- Tyryloxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-butyryloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 9,10-bis (2-butyryloxy-3-allyloxy) Propoxy) anthracene, 9,10-bis (2-butyryloxy-3-methallyloxypropoxy) anthracene, 9,10-bis (2-butyryloxy-3-phenoxypropoxy) anthracene, 9,10-bis (2-butyryloxy-) 3-tolyloxypropoxy) anthracene, 9,10-bis (2-butyryloxy-3-naphthyloxypropoxy) anthracene, and the like.

Examples of the case where X and Y are hydrogen atoms and B is a butyl group include, for example, 9,10-bis (2-pentanoyloxy-3-methoxypropoxy) anthracene, 9,10-bis (2-pentanoyl) Oxy-3-ethoxypropoxy) anthracene, 9,10-bis [2-pentanoyloxy-3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-pentanoyloxy-3- (n-butoxy) ) Propoxy] anthracene, 9,10-bis [2-pentanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 9,10-bis [2-pentanoyloxy-3- (n-hexyloxy) propoxy Anthracene, 9,10-bis [2-pentanoyloxy-3- (n-heptyloxy) propoxy] anthra 9,10-bis [2-pentanoyloxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-pentanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 9,10-bis (2-pentanoyloxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-pentanoyloxy-3-methallyloxypropoxy) anthracene, 9,10-bis (2-penta) Noyloxy-3-phenoxypropoxy) anthracene, 9,10-bis (2-pentanoyloxy-3-tolyloxypropoxy) anthracene, 9,10-bis (2-pentanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Examples of the case where X and Y are hydrogen atoms and B is a pentyl group include, for example, 9,10-bis (2-hexanoyloxy-3-methoxypropoxy) anthracene, 9,10-bis (2-hexanoyl). Oxy-3-ethoxypropoxy) anthracene, 9,10-bis [2-hexanoyloxy-3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-hexanoyloxy-3- (n-butoxy) ) Propoxy] anthracene, 9,10-bis [2-hexanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 9,10-bis [2-hexanoyloxy-3- (n-hexyloxy) propoxy Anthracene, 9,10-bis [2-hexanoyloxy-3- (n-heptyloxy) propoxy] ant Sen, 9,10-bis [2-hexanoyloxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-hexanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 9,10-bis (2-hexanoyloxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-hexanoyloxy-3-methallyloxypropoxy) anthracene, 9,10-bis (2-hexa) Noyloxy-3-phenoxypropoxy) anthracene, 9,10-bis (2-hexanoyloxy-3-tolyloxypropoxy) anthracene, 9,10-bis (2-hexanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Examples of the case where X and Y are hydrogen atoms and B is a hexyl group include, for example, 9,10-bis (2-heptanoyloxy-3-methoxypropoxy) anthracene, 9,10-bis (2-heptanoyl) Oxy-3-ethoxypropoxy) anthracene, 9,10-bis [2-heptanoyloxy-3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-heptanoyloxy-3- (n-butoxy) ) Propoxy] anthracene, 9,10-bis [2-heptanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 9,10-bis [2-heptanoyloxy-3- (n-hexyloxy) propoxy Anthracene, 9,10-bis [2-heptanoyloxy-3- (n-heptyloxy) propoxy] ant Sen, 9,10-bis [2-heptanoyloxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-heptanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 9,10-bis (2-heptanoyloxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-heptanoyloxy-3-methallyloxypropoxy) anthracene, 9,10-bis (2-hepta) Noyloxy-3-phenoxypropoxy) anthracene, 9,10-bis (2-heptanoyloxy-3-tolyloxypropoxy) anthracene, 9,10-bis (2-heptanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Examples of the case where X and Y are hydrogen atoms and B is a heptyl group include, for example, 9,10-bis (2-octanoyloxy-3-methoxypropoxy) anthracene, 9,10-bis (2-octanoyl). Oxy-3-ethoxypropoxy) anthracene, 9,10-bis [2-octanoyloxy-3- (n-propoxy) propoxy] anthracene, 9,10-bis [2-octanoyloxy-3- (n-butoxy) ) Propoxy] anthracene, 9,10-bis [2-octanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 9,10-bis [2-octanoyloxy-3- (n-hexyloxy) propoxy Anthracene, 9,10-bis [2-octanoyloxy-3- (n-heptyloxy) propoxy] ant Sen, 9,10-bis [2-octanoyloxy-3- (n-octyloxy) propoxy] anthracene, 9,10-bis [2-octanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 9,10-bis (2-octanoyloxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-octanoyloxy-3-methallyloxypropoxy) anthracene, 9,10-bis (2-octa) Noyloxy-3-phenoxypropoxy) anthracene, 9,10-bis (2-octanoyloxy-3-tolyloxypropoxy) anthracene, 9,10-bis (2-octanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Next, when X or Y is a methyl group and B is a methyl group, for example, 2-methyl-9,10-bis (2-acetoxy-3-methoxypropoxy) anthracene, 2-methyl-9 , 10-bis (2-acetoxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-acetoxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-Acetoxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-acetoxy-3- (n-pentyloxy) propoxy] anthracene, 2-methyl-9,10- Bis [2-acetoxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-acetoxy-3- (n-he Tiloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-acetoxy-3- (n-octyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-acetoxy-3- (2) -Ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-acetoxy-3-allyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-acetoxy-3-methallyloxypropoxy) ) Anthracene, 2-methyl-9,10-bis (2-acetoxy-3-phenoxypropoxy) anthracene, 2-methyl-9,10-bis (2-acetoxy-3-tolyloxypropoxy) anthracene, 2-methyl- 9,10-bis (2-acetoxy-3-naphthyloxypropoxy) anthrace Etc. The.

Examples of the case where X or Y is a methyl group and B is an ethyl group include, for example, 2-methyl-9,10-bis (2-propionyloxy-3-methoxypropoxy) anthracene, 2-methyl-9,10 -Bis (2-propionyloxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-propionyloxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-propionyloxy-3- (n-pentyloxy) propoxy] anthracene, 2-methyl-9, 10-bis [2-propionyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl-9 10-bis [2-propionyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-propionyloxy-3- (n-octyloxy) propoxy] anthracene, 2- Methyl-9,10-bis [2-propionyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-propionyloxy-3-allyloxypropoxy) anthracene, 2- Methyl-9,10-bis (2-propionyloxy-3-methallyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-propionyloxy-3-phenoxypropoxy) anthracene, 2-methyl-9, 10-bis (2-propionyloxy-3-tolyloxypropoxy) Anthracene, 2-methyl-9,10-bis (2-propionyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a methyl group and B is a propyl group include, for example, 2-methyl-9,10-bis (2-butyryloxy-3-methoxypropoxy) anthracene, 2-methyl-9,10- Bis (2-butyryloxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-butyryloxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9,10-bis [2- Butyryloxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-butyryloxy-3- (n-pentyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2 -Butyryloxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-buty Ruoxy-3- (n-heptyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-butyryloxy-3- (n-octyloxy) propoxy] anthracene, 2-methyl-9,10-bis [ 2-butyryloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-butyryloxy-3-allyloxypropoxy) anthracene, 2-methyl-9,10-bis (2- Butyryloxy-3-methallyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-butyryloxy-3-phenoxypropoxy) anthracene, 2-methyl-9,10-bis (2-butyryloxy-3-tolyloxy) Propoxy) anthracene, 2-methyl-9,10-bis (2-buty) Aryloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a methyl group and B is a butyl group include, for example, 2-methyl-9,10-bis (2-pentanoyloxy-3-methoxypropoxy) anthracene, 2-methyl-9, 10-bis (2-pentanoyloxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-pentanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9, 10-bis [2-pentanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-pentanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Methyl-9,10-bis [2-pentanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl-9 10-bis [2-pentanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-pentanoyloxy-3- (n-octyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-pentanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-pentanoyloxy-3-allyloxypropoxy) Anthracene, 2-methyl-9,10-bis (2-pentanoyloxy-3-methallyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-pentanoyloxy-3-phenoxypropoxy) anthracene, 2-Methyl-9,10-bis (2-pentanoyloxy-3-tolyloxypropoxy) Anthracene, 2-methyl-9,10-bis (2-pentanoyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a methyl group and B is a pentyl group include, for example, 2-methyl-9,10-bis (2-hexanoyloxy-3-methoxypropoxy) anthracene, 2-methyl-9, 10-bis (2-hexanoyloxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-hexanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9, 10-bis [2-hexanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-hexanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Methyl-9,10-bis [2-hexanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl- , 10-bis [2-hexanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-hexanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-methyl-9,10-bis [2-hexanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-hexanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-methyl-9,10-bis (2-hexanoyloxy-3-methallyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-hexanoyloxy-3-phenoxypropoxy) anthracene 2-methyl-9,10-bis (2-hexanoyloxy-3-tolyloxypropoxy) Anthracene, 2-methyl-9,10-bis (2-hexanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a methyl group and B is a hexyl group include, for example, 2-methyl-9,10-bis (2-heptanoyloxy-3-methoxypropoxy) anthracene, 2-methyl-9, 10-bis (2-heptanoyloxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-heptanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9, 10-bis [2-heptanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-heptanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Methyl-9,10-bis [2-heptanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl- , 10-bis [2-heptanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-heptanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-methyl-9,10-bis [2-heptanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-heptanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-methyl-9,10-bis (2-heptanoyloxy-3-methallyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-heptanoyloxy-3-phenoxypropoxy) anthracene 2-methyl-9,10-bis (2-heptanoyloxy-3-tolyloxypropoxy) Anthracene, 2-methyl-9,10-bis (2-heptanoyloxymethyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a methyl group and B is a heptyl group include, for example, 2-methyl-9,10-bis (2-octanoyloxy-3-methoxypropoxy) anthracene, 2-methyl-9, 10-bis (2-octanoyloxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis [2-octanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-methyl-9, 10-bis [2-octanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-methyl-9,10-bis [2-octanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Methyl-9,10-bis [2-octanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-methyl- , 10-bis [2-octanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-methyl-9,10-bis [2-octanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-methyl-9,10-bis [2-octanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-methyl-9,10-bis (2-octanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-methyl-9,10-bis (2-octanoyloxy-3-methallyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-octanoyloxy-3-phenoxypropoxy) anthracene 2-methyl-9,10-bis (2-octanoyloxy-3-tolyloxypropoxy) Anthracene, 2-methyl-9,10-bis (2-octanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Next, when X or Y is an ethyl group and B is a methyl group, for example, 2-ethyl-9,10-bis (2-acetoxy-3-methoxypropoxy) anthracene, 2-ethyl-9 , 10-bis (2-acetoxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-acetoxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-Acetoxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-acetoxy-3- (n-pentyloxy) propoxy] anthracene, 2-ethyl-9,10- Bis [2-acetoxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-acetoxy-3- (n-he Tiloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-acetoxy-3- (n-octyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-acetoxy-3- (2) -Ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-acetoxy-3-allyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-acetoxy-3-methallyloxypropoxy) ) Anthracene, 2-ethyl-9,10-bis (2-acetoxy-3-phenoxypropoxy) anthracene, 2-ethyl-9,10-bis (2-acetoxy-3-tolyloxypropoxy) anthracene, 2-ethyl- 9,10-bis (2-acetoxy-3-naphthyloxypropoxy) anthrace Etc. The.

Examples of the case where X or Y is an ethyl group and B is an ethyl group include, for example, 2-ethyl-9,10-bis (2-propionyloxy-3-methoxypropoxy) anthracene, 2-ethyl-9,10 -Bis (2-propionyloxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-propionyloxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-propionyloxy-3- (n-pentyloxy) propoxy] anthracene, 2-ethyl-9, 10-bis [2-propionyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl-9 10-bis [2-propionyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-propionyloxy-3- (n-octyloxy) propoxy] anthracene, 2- Ethyl-9,10-bis [2-propionyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-propionyloxy-3-allyloxypropoxy) anthracene, 2- Ethyl-9,10-bis (2-propionyloxy-3-methallyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-propionyloxy-3-phenoxypropoxy) anthracene, 2-ethyl-9, 10-bis (2-propionyloxy-3-tolyloxypropoxy) Anthracene, 2-ethyl-9,10-bis (2-propionyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is an ethyl group and B is a propyl group include, for example, 2-ethyl-9,10-bis (2-butyryloxy-3-methoxypropoxy) anthracene, 2-ethyl-9,10- Bis (2-butyryloxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-butyryloxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2- Butyryloxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-butyryloxy-3- (n-pentyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2 -Butyryloxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-buty Ruoxy-3- (n-heptyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-butyryloxy-3- (n-octyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [ 2-butyryloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-butyryloxy-3-allyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2- Butyryloxy-3-methallyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-butyryloxy-3-phenoxypropoxy) anthracene, 2-ethyl-9,10-bis (2-butyryloxy-3-tolyloxy) Propoxy) anthracene, 2-ethyl-9,10-bis (2-buty) Aryloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is an ethyl group and B is a butyl group include, for example, 2-ethyl-9,10-bis (2-pentanoyloxy-3-methoxypropoxy) anthracene, 2-ethyl-9, 10-bis (2-pentanoyloxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-pentanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9, 10-bis [2-pentanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-pentanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Ethyl-9,10-bis [2-pentanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl-9 10-bis [2-pentanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-pentanoyloxy-3- (n-octyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-pentanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-pentanoyloxy-3-allyloxypropoxy) Anthracene, 2-ethyl-9,10-bis (2-pentanoyloxy-3-methallyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-pentanoyloxy-3-phenoxypropoxy) anthracene, 2-Ethyl-9,10-bis (2-pentanoyloxy-3-tolyloxypropoxy) Anthracene, 2-ethyl-9,10-bis (2-pentanoyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is an ethyl group and B is a pentyl group include, for example, 2-ethyl-9,10-bis (2-hexanoyloxy-3-methoxypropoxy) anthracene, 2-ethyl-9, 10-bis (2-hexanoyloxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-hexanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9, 10-bis [2-hexanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-hexanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Ethyl-9,10-bis [2-hexanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl- , 10-bis [2-hexanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-hexanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-ethyl-9,10-bis [2-hexanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-hexanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-ethyl-9,10-bis (2-hexanoyloxy-3-methallyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-hexanoyloxy-3-phenoxypropoxy) anthracene 2-ethyl-9,10-bis (2-hexanoyloxy-3-tolyloxypropoxy) Anthracene, 2-ethyl-9,10-bis (2-hexanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is an ethyl group and B is a hexyl group include, for example, 2-ethyl-9,10-bis (2-heptanoyloxy-3-methoxypropoxy) anthracene, 2-ethyl-9, 10-bis (2-heptanoyloxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-heptanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9, 10-bis [2-heptanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-heptanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Ethyl-9,10-bis [2-heptanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl- , 10-bis [2-heptanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-heptanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-ethyl-9,10-bis [2-heptanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-heptanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-ethyl-9,10-bis (2-heptanoyloxy-3-methallyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-heptanoyloxy-3-phenoxypropoxy) anthracene 2-ethyl-9,10-bis (2-heptanoyloxy-3-tolyloxypropoxy) Anthracene, 2-ethyl-9,10-bis (2-heptanoyloxymethyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is an ethyl group and B is a heptyl group include, for example, 2-ethyl-9,10-bis (2-octanoyloxy-3-methoxypropoxy) anthracene, 2-ethyl-9, 10-bis (2-octanoyloxy-3-ethoxypropoxy) anthracene, 2-ethyl-9,10-bis [2-octanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-ethyl-9, 10-bis [2-octanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-octanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Ethyl-9,10-bis [2-octanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-ethyl- , 10-bis [2-octanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-ethyl-9,10-bis [2-octanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-ethyl-9,10-bis [2-octanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-octanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-ethyl-9,10-bis (2-octanoyloxy-3-methallyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-octanoyloxy-3-phenoxypropoxy) anthracene 2-ethyl-9,10-bis (2-octanoyloxy-3-tolyloxypropoxy) Anthracene, 2-ethyl-9,10-bis (2-octanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Next, when X and Y are both methyl groups and B is a methyl group, for example, 2,6-dimethyl-9,10-bis (2-acetoxy-3-methoxypropoxy) anthracene, 2, 6-dimethyl-9,10-bis (2-acetoxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-acetoxy-3- (n-propoxy) propoxy] anthracene, 2, 6-dimethyl-9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-acetoxy-3- (n-pentyloxy) propoxy Anthracene, 2,6-dimethyl-9,10-bis [2-acetoxy-3- (n-hexyloxy) propoxy] anthracene, 2,6-dimethyl 9,10-bis [2-acetoxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-acetoxy-3- (n-octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-acetoxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis (2-acetoxy-3-allyloxypropoxy) Anthracene, 2,6-dimethyl-9,10-bis (2-acetoxy-3-methallyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-acetoxy-3-phenoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-acetoxy-3-tolyloxypropoxy) anthracene, 2 6-dimethyl-9,10-bis (2-acetoxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X and Y are both a methyl group and B is an ethyl group include, for example, 2,6-dimethyl-9,10-bis (2-propionyloxy-3-methoxypropoxy) anthracene, 2,6- Dimethyl-9,10-bis (2-propionyloxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-propionyloxy-3- (n-propoxy) propoxy] anthracene, 2, 6-dimethyl-9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-propionyloxy-3- (n-pentyloxy) ) Propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-propionyloxy-3- (n-hexyloxy) Ropoxy] anthracene, 2,6-dimethyl-9,10-bis [2-propionyloxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-propionyloxy- 3- (n-octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-propionyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl-9,10 -Bis (2-propionyloxy-3-allyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-propionyloxy-3-methallyloxypropoxy) anthracene, 2,6-dimethyl-9, 10-bis (2-propionyloxy-3-phenoxypropoxy) anthracene, 2, -Dimethyl-9,10-bis (2-propionyloxy-3-tolyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-propionyloxy-3-naphthyloxypropoxy) anthracene, etc. .

Examples of the case where X and Y are both a methyl group and B is a propyl group include, for example, 2,6-dimethyl-9,10-bis (2-butyryloxy-3-methoxypropoxy) anthracene, 2,6-dimethyl. -9,10-bis (2-butyryloxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-butyryloxy-3- (n-propoxy) propoxy] anthracene, 2,6-dimethyl -9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-butyryloxy-3- (n-pentyloxy) propoxy] anthracene, 2,6-Dimethyl-9,10-bis [2-butyryloxy-3- (n-hexyloxy) propoxy] anthrace 2,6-dimethyl-9,10-bis [2-butyryloxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-butyryloxy-3- (n- Octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-butyryloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis (2-butyryloxy) -3-allyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-butyryloxy-3-methallyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-butyryloxy-) 3-phenoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-butyryloxy) 3-tolyl oxy propoxy) anthracene, 2,6-dimethyl-9,10-bis (2-butyryloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X and Y are both methyl groups and B is a butyl group include, for example, 2,6-dimethyl-9,10-bis (2-pentanoyloxy-3-methoxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-pentanoyloxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-pentanoyloxy-3- (n-propoxy) propoxy] anthracene 2,6-dimethyl-9,10-bis [2-pentanoyloxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-pentanoyloxy-3- (N-pentyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-pentanoyloxy-3- (n-hexyloxy) Ropoxy] anthracene, 2,6-dimethyl-9,10-bis [2-pentanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-pentanoyl Oxy-3- (n-octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-pentanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl- 9,10-bis (2-pentanoyloxy-3-allyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-pentanoyloxy-3-methallyloxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-pentanoyloxy-3-phenoxypropoxy) anthracene, 2, -Dimethyl-9,10-bis (2-pentanoyloxy-3-tolyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-pentanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Can be mentioned.

Examples of the case where X and Y are both methyl groups and B is a pentyl group include, for example, 2,6-dimethyl-9,10-bis (2-hexanoyloxy-3-methoxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-hexanoyloxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-hexanoyloxy-3- (n-propoxy) propoxy] anthracene 2,6-dimethyl-9,10-bis [2-hexanoyloxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-hexanoyloxy-3- (N-pentyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-hexanoyloxy-3- (n-hexyloxy) Propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-hexanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-hexanoyl] Oxy-3- (n-octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-hexanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl- 9,10-bis (2-hexanoyloxy-3-allyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hexanoyloxy-3-methallyloxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-hexanoyloxy-3-phenoxypropoxy) anthracene, 2 6-dimethyl-9,10-bis (2-hexanoyloxy-3-tolyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hexanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Examples of the case where X and Y are both methyl groups and B is a hexyl group include, for example, 2,6-dimethyl-9,10-bis (2-heptanoyloxy-3-methoxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-heptanoyloxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-heptanoyloxy-3- (n-propoxy) propoxy] anthracene 2,6-dimethyl-9,10-bis [2-heptanoyloxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-heptanoyloxy-3- (N-pentyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-heptanoyloxy-3- (n-hexyloxy) Propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-heptanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-heptanoyl] Oxy-3- (n-octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-heptanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl- 9,10-bis (2-heptanoyloxy-3-allyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-heptanoyloxy-3-methallyloxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-heptanoyloxy-3-phenoxypropoxy) anthracene, 2 6-dimethyl-9,10-bis (2-heptanoyloxy-3-tolyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-heptanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

When X and Y are both methyl groups and B is a heptyl group, for example, 2,6-dimethyl-9,10-bis (2-octanoyloxy-3-methoxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-octanoyloxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-octanoyloxy-3- (n-propoxy) propoxy] anthracene 2,6-dimethyl-9,10-bis [2-octanoyloxy-3- (n-butoxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-octanoyloxy-3- (N-pentyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-octanoyloxy-3- (n-hexyloxy) Propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-octanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-octanoyl] Oxy-3- (n-octyloxy) propoxy] anthracene, 2,6-dimethyl-9,10-bis [2-octanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2,6-dimethyl- 9,10-bis (2-octanoyloxy-3-allyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-octanoyloxy-3-methallyloxypropoxy) anthracene, 2,6 -Dimethyl-9,10-bis (2-octanoyloxy-3-phenoxypropoxy) anthracene, 2 6-dimethyl-9,10-bis (2-octanoyloxy-3-tolyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-octanoyloxy-3-naphthyloxypropoxy) anthracene, etc. Is mentioned.

Next, when X or Y is a chlorine atom and B is a methyl group, for example, 2-chloro-9,10-bis (2-acetoxy-3-methoxypropoxy) anthracene, 2-chloro-9 , 10-bis (2-acetoxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-acetoxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-Acetoxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-acetoxy-3- (n-pentyloxy) propoxy] anthracene, 2-chloro-9,10- Bis [2-acetoxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-acetoxy-3- (n-he Tiloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-acetoxy-3- (n-octyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-acetoxy-3- (2) -Ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-acetoxy-3-allyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-acetoxy-3-methallyloxypropoxy) ) Anthracene, 2-chloro-9,10-bis (2-acetoxy-3-phenoxypropoxy) anthracene, 2-chloro-9,10-bis (2-acetoxy-3-tolyloxypropoxy) anthracene, 2-chloro- 9,10-bis (2-acetoxy-3-naphthyloxypropoxy) anthrace Etc. The.

Examples of the case where X or Y is a chlorine atom and B is an ethyl group include, for example, 2-chloro-9,10-bis (2-propionyloxy-3-methoxypropoxy) anthracene, 2-chloro-9,10 -Bis (2-propionyloxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-propionyloxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-propionyloxy-3- (n-pentyloxy) propoxy] anthracene, 2-chloro-9, 10-bis [2-propionyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro-9 10-bis [2-propionyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-propionyloxy-3- (n-octyloxy) propoxy] anthracene, 2- Chloro-9,10-bis [2-propionyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-propionyloxy-3-allyloxypropoxy) anthracene, 2- Chloro-9,10-bis (2-propionyloxy-3-methallyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-propionyloxy-3-phenoxypropoxy) anthracene, 2-chloro-9, 10-bis (2-propionyloxy-3-tolyloxypropoxy) Anthracene, 2-chloro-9,10-bis (2-propionyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a chlorine atom and B is a propyl group include, for example, 2-chloro-9,10-bis (2-butyryloxy-3-methoxypropoxy) anthracene, 2-chloro-9,10- Bis (2-butyryloxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-butyryloxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9,10-bis [2- Butyryloxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-butyryloxy-3- (n-pentyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2 -Butyryloxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-buty Ruoxy-3- (n-heptyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-butyryloxy-3- (n-octyloxy) propoxy] anthracene, 2-chloro-9,10-bis [ 2-butyryloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-butyryloxy-3-allyloxypropoxy) anthracene, 2-chloro-9,10-bis (2- Butyryloxy-3-methallyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-butyryloxy-3-phenoxypropoxy) anthracene, 2-chloro-9,10-bis (2-butyryloxy-3-tolyloxy) Propoxy) anthracene, 2-chloro-9,10-bis (2-buty) Aryloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a chlorine atom and B is a butyl group include, for example, 2-chloro-9,10-bis (2-pentanoyloxy-3-methoxypropoxy) anthracene, 2-chloro-9, 10-bis (2-pentanoyloxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-pentanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9, 10-bis [2-pentanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-pentanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Chloro-9,10-bis [2-pentanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro-9 10-bis [2-pentanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-pentanoyloxy-3- (n-octyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-pentanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-pentanoyloxy-3-allyloxypropoxy) Anthracene, 2-chloro-9,10-bis (2-pentanoyloxy-3-methallyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-pentanoyloxy-3-phenoxypropoxy) anthracene, 2-Chloro-9,10-bis (2-pentanoyloxy-3-tolyloxypropoxy) Anthracene, 2-chloro-9,10-bis (2-pentanoyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a chlorine atom and B is a pentyl group include, for example, 2-chloro-9,10-bis (2-hexanoyloxy-3-methoxypropoxy) anthracene, 2-chloro-9, 10-bis (2-hexanoyloxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-hexanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9, 10-bis [2-hexanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-hexanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Chloro-9,10-bis [2-hexanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro- , 10-bis [2-hexanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-hexanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-chloro-9,10-bis [2-hexanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-hexanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-chloro-9,10-bis (2-hexanoyloxy-3-methallyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-hexanoyloxy-3-phenoxypropoxy) anthracene 2-chloro-9,10-bis (2-hexanoyloxy-3-tolyloxypropoxy) Anthracene, 2-chloro-9,10-bis (2-hexanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a chlorine atom and B is a hexyl group include, for example, 2-chloro-9,10-bis (2-heptanoyloxy-3-methoxypropoxy) anthracene, 2-chloro-9, 10-bis (2-heptanoyloxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-heptanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9, 10-bis [2-heptanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-heptanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Chloro-9,10-bis [2-heptanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro- , 10-bis [2-heptanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-heptanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-chloro-9,10-bis [2-heptanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-heptanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-chloro-9,10-bis (2-heptanoyloxy-3-methallyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-heptanoyloxy-3-phenoxypropoxy) anthracene 2-chloro-9,10-bis (2-heptanoyloxy-3-tolyloxypropoxy) Anthracene, 2-chloro-9,10-bis (2-heptanoyloxymethyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a chlorine atom and B is a heptyl group include, for example, 2-chloro-9,10-bis (2-octanoyloxy-3-methoxypropoxy) anthracene, 2-chloro-9, 10-bis (2-octanoyloxy-3-ethoxypropoxy) anthracene, 2-chloro-9,10-bis [2-octanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-chloro-9, 10-bis [2-octanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-chloro-9,10-bis [2-octanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Chloro-9,10-bis [2-octanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-chloro- , 10-bis [2-octanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-chloro-9,10-bis [2-octanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-chloro-9,10-bis [2-octanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-octanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-chloro-9,10-bis (2-octanoyloxy-3-methallyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-octanoyloxy-3-phenoxypropoxy) anthracene 2-chloro-9,10-bis (2-octanoyloxy-3-tolyloxypropoxy) Anthracene, 2-chloro-9,10-bis (2-octanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Next, when X or Y is a bromine atom and B is a methyl group, for example, 2-bromo-9,10-bis (2-acetoxy-3-methoxypropoxy) anthracene, 2-bromo-9 , 10-bis (2-acetoxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-acetoxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-Acetoxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-acetoxy-3- (n-pentyloxy) propoxy] anthracene, 2-bromo-9,10- Bis [2-acetoxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-acetoxy-3- (n-he Tiloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-acetoxy-3- (n-octyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-acetoxy-3- (2) -Ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-acetoxy-3-allyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-acetoxy-3-methallyloxypropoxy) ) Anthracene, 2-bromo-9,10-bis (2-acetoxy-3-phenoxypropoxy) anthracene, 2-bromo-9,10-bis (2-acetoxy-3-tolyloxypropoxy) anthracene, 2-bromo- 9,10-bis (2-acetoxy-3-naphthyloxypropoxy) anthrace Etc. The.

Examples of the case where X or Y is a bromine atom and B is an ethyl group include, for example, 2-bromo-9,10-bis (2-propionyloxy-3-methoxypropoxy) anthracene, 2-bromo-9,10 -Bis (2-propionyloxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-propionyloxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-propionyloxy-3- (n-pentyloxy) propoxy] anthracene, 2-bromo-9, 10-bis [2-propionyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo-9 10-bis [2-propionyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-propionyloxy-3- (n-octyloxy) propoxy] anthracene, 2- Bromo-9,10-bis [2-propionyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-propionyloxy-3-allyloxypropoxy) anthracene, 2- Bromo-9,10-bis (2-propionyloxy-3-methallyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-propionyloxy-3-phenoxypropoxy) anthracene, 2-bromo-9, 10-bis (2-propionyloxy-3-tolyloxypropoxy) Anthracene, 2-bromo-9,10-bis (2-propionyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a bromine atom and B is a propyl group include, for example, 2-bromo-9,10-bis (2-butyryloxy-3-methoxypropoxy) anthracene, 2-bromo-9,10- Bis (2-butyryloxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-butyryloxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9,10-bis [2- Butyryloxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-butyryloxy-3- (n-pentyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2 -Butyryloxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-buty Ruoxy-3- (n-heptyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-butyryloxy-3- (n-octyloxy) propoxy] anthracene, 2-bromo-9,10-bis [ 2-butyryloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-butyryloxy-3-allyloxypropoxy) anthracene, 2-bromo-9,10-bis (2- Butyryloxy-3-methallyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-butyryloxy-3-phenoxypropoxy) anthracene, 2-bromo-9,10-bis (2-butyryloxy-3-tolyloxy) Propoxy) anthracene, 2-bromo-9,10-bis (2-buty) Aryloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a bromine atom and B is a butyl group include, for example, 2-bromo-9,10-bis (2-pentanoyloxy-3-methoxypropoxy) anthracene, 2-bromo-9, 10-bis (2-pentanoyloxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-pentanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9, 10-bis [2-pentanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-pentanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Bromo-9,10-bis [2-pentanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo-9 10-bis [2-pentanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-pentanoyloxy-3- (n-octyloxy) propoxy] anthracene, 2-Bromo-9,10-bis [2-pentanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-pentanoyloxy-3-allyloxypropoxy) Anthracene, 2-bromo-9,10-bis (2-pentanoyloxy-3-methallyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-pentanoyloxy-3-phenoxypropoxy) anthracene, 2-Bromo-9,10-bis (2-pentanoyloxy-3-tolyloxypropoxy) Anthracene, 2-bromo-9,10-bis (2-pentanoyloxy-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a bromine atom and B is a pentyl group include, for example, 2-bromo-9,10-bis (2-hexanoyloxy-3-methoxypropoxy) anthracene, 2-bromo-9, 10-bis (2-hexanoyloxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-hexanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9, 10-bis [2-hexanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-hexanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Bromo-9,10-bis [2-hexanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo- , 10-bis [2-hexanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-hexanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-bromo-9,10-bis [2-hexanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-hexanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-bromo-9,10-bis (2-hexanoyloxy-3-methallyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-hexanoyloxy-3-phenoxypropoxy) anthracene 2-bromo-9,10-bis (2-hexanoyloxy-3-tolyloxypropoxy) Anthracene, 2-bromo-9,10-bis (2-hexanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a bromine atom and B is a hexyl group include, for example, 2-bromo-9,10-bis (2-heptanoyloxy-3-methoxypropoxy) anthracene, 2-bromo-9, 10-bis (2-heptanoyloxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-heptanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9, 10-bis [2-heptanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-heptanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Bromo-9,10-bis [2-heptanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo- , 10-bis [2-heptanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-heptanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-bromo-9,10-bis [2-heptanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-heptanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-bromo-9,10-bis (2-heptanoyloxy-3-methallyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-heptanoyloxy-3-phenoxypropoxy) anthracene 2-bromo-9,10-bis (2-heptanoyloxy-3-tolyloxypropoxy) Anthracene, 2-bromo-9,10-bis (2-heptanoyloxymethyl-3-naphthyloxy propoxy) anthracene, and the like.

Examples of the case where X or Y is a bromine atom and B is a heptyl group include, for example, 2-bromo-9,10-bis (2-octanoyloxy-3-methoxypropoxy) anthracene, 2-bromo-9, 10-bis (2-octanoyloxy-3-ethoxypropoxy) anthracene, 2-bromo-9,10-bis [2-octanoyloxy-3- (n-propoxy) propoxy] anthracene, 2-bromo-9, 10-bis [2-octanoyloxy-3- (n-butoxy) propoxy] anthracene, 2-bromo-9,10-bis [2-octanoyloxy-3- (n-pentyloxy) propoxy] anthracene, 2 -Bromo-9,10-bis [2-octanoyloxy-3- (n-hexyloxy) propoxy] anthracene, 2-bromo- , 10-bis [2-octanoyloxy-3- (n-heptyloxy) propoxy] anthracene, 2-bromo-9,10-bis [2-octanoyloxy-3- (n-octyloxy) propoxy] anthracene 2-bromo-9,10-bis [2-octanoyloxy-3- (2-ethylhexyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-octanoyloxy-3-allyloxypropoxy) ) Anthracene, 2-bromo-9,10-bis (2-octanoyloxy-3-methallyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-octanoyloxy-3-phenoxypropoxy) anthracene 2-bromo-9,10-bis (2-octanoyloxy-3-tolyloxypropoxy) Anthracene, 2-bromo-9,10-bis (2-octanoyl-3-naphthyloxy propoxy) anthracene, and the like.

Among these exemplified compounds, 9,10-bis (2-acetoxy-3-butoxypropoxy) anthracene (compound A) shown below is easy to produce and has a great effect as a photopolymerization sensitizer. ), 9,10-bis (2-propionyloxy-3-butoxypropoxy) anthracene (Compound B), 9,10-bis (2-butyryloxy-3-butoxypropoxy) anthracene (Compound C), 9,10-bis (2-Acetoxy-3-phenoxypropoxy) anthracene (Compound D) is preferred.

(Production method)
Next, a method for producing the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention will be described. The 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention reduces the 9,10-anthraquinone compound represented by the general formula (4). Then, a 9,10-bis (2-hydroxy-3-substituted oxypropoxy) anthracene compound obtained by reacting with a hydroxyhydroxy etherifying agent is synthesized by reacting with an acylating agent in the presence of a basic compound. be able to.

Specifically, the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention is synthesized as follows. That is, the corresponding 9,10-anthraquinone compound is reduced in a solvent (first reaction), and then the 9,10-dihydroxyanthracene compound represented by the following general formula (3) is obtained in the presence of a base compound or Hydroxyetherification in the absence (second reaction). Finally, the resulting 9,10-bis (2-hydroxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (2) is acylated with an acylating agent in the presence of a basic compound. (Third reaction).

In the first reaction, X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.

In the second reaction, X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom. In the general formula (2), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms.

In the third reaction, X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom. In the general formula (2), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms. In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents from 1 to carbon atoms. 8 represents an alkyl group or an aryl group.

Hereinafter, the first reaction will be described in order. In the 9,10-anthraquinone compound represented by the general formula (4) used as a raw material in the first reaction, X and Y may be the same or different, and each is a hydrogen atom, having 1 to 8 carbon atoms. It represents either an alkyl group or a halogen atom.

In the general formula (4), the alkyl group having 1 to 8 carbon atoms represented by X and Y includes a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and an i-butyl group. , T-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group and the like. As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, etc. are mentioned as a halogen atom.

Specific examples of the 9,10-anthraquinone compound represented by the general formula (4) include anthraquinone, 2-methyl-9,10-anthraquinone, 2-ethyl-9,10-anthraquinone, and 2- (n-propyl). -9,10-anthraquinone, 2- (i-propyl) -9,10-anthraquinone, 2- (n-butyl) -9,10-anthraquinone, 2- (i-butyl) -9,10-anthraquinone, 2 -(N-pentyl) -9,10-anthraquinone, 2- (n-hexyl) -9,10-anthraquinone, 2- (n-heptyl) -9,10-anthraquinone, 2- (n-octyl) -9 , 10-anthraquinone, 2- (2-ethylhexyl) -9,10-anthraquinone, 2-fluoro-9,10-anthraquinone, 2-chloro-9,10-anthra Non, 2-bromo-9,10-anthraquinone, and the like.

The reducing agent used in the first reaction is not particularly limited as long as it can reduce the ketone group, and sodium borohydride, lithium aluminum hydride, sodium dithionite, thiourea peroxide and the like are used. These reducing agents are added in a molar ratio of 2 or more with respect to the 2-substituted-9,10-anthraquinone compound. Usually, it is 2 to 4 mole times.

The reduction reaction is usually performed in a solvent. The solvent is not particularly limited, and amide solvents such as dimethylformamide and dimethylacetamide, alcohol solvents such as methanol and ethanol, and ether solvents such as tetrahydrofuran and dioxane are preferably used.

In the first reaction, the reaction temperature for the reduction reaction of the 9,10-anthraquinone compound is usually 0 ° C. or higher and 120 ° C. or lower. More preferably, it is 40 degreeC or more and 80 degrees C or less. If it is 0 ° C. or lower, the reaction is slow, and if it is 120 ° C. or higher, side reactions are liable to occur and the purity of the product is lowered. The reduction is completed when the reaction time is 0.5 to 3 hours, usually 1 hour. The obtained 9,10-dihydroxyanthracene compound can be used for the next hydroxyetherification reaction without being usually isolated.

In the first reaction, catalytic hydrogen reduction using a noble metal as a catalyst is also possible. Examples of usable noble metal catalysts include palladium-supported activated carbon, palladium-supported alumina, and platinum-supported activated carbon. In particular, 5% palladium / carbon is preferably used. The addition amount of the noble metal catalyst to the 2-substituted-9,10-anthraquinone compound is usually 0.01% or more and 5% or less, more preferably 0.2% or more and 2% or less. If the addition amount of the catalyst is less than 0.01%, the hydrogenation rate is slow, and if the addition amount exceeds 5%, the hydrogenation of the aromatic ring occurs side by side reaction, which is not preferable. Ruthenium catalysts that have been developed recently are also useful.

The reduction reaction is usually performed in a solvent. Examples of the solvent to be used include alcohol solvents such as methanol and ethanol, ketone solvents such as acetone and methyl ethyl ketone, and ether solvents such as tetrahydrofuran and 1,4-dioxane. The concentration of the 9,10-anthraquinone compound in the solvent depends on the solubility in the solvent, but is usually about 5% to 20%. The pressure of hydrogen is usually about 1 Pa to 10 Pa. The reaction time is about 1 to 3 hours. After completion of the hydrogen reduction, the catalyst is removed by filtration, and the filtrate is subjected to the subsequent hydroxy etherification reaction.

Next, the second reaction will be described. The hydroxy etherification agent used in the second reaction is methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, octyl glycidyl ether, allyl glycidyl ether, methallyl glycidyl ether , Phenyl glycidyl ether, tolyl glycidyl ether or naphthyl glycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether and the like.

In the second reaction, the addition ratio of the hydroxy etherifying agent to the 9,10-dihydroxyanthracene compound is 2.0 mol times or more and 30 mol times or less, preferably 3.0 mol times or more and 20 mol times or less. If it is less than 2.0 mol times, the 9,10-dihydroxyanthracene compound remains unreacted, and if it is added more than 30 mol times, the 9,10-bis (2-hydroxyalkoxy) anthracene compound produced is added to the reaction solution. The solubility becomes high, and it becomes difficult to crystallize from the reaction product, resulting in a decrease in yield.

As the base compound used when the second reaction is carried out in the presence of the base compound, inorganic alkali salts, alkali metal carbonates and the like are usually used. As the inorganic alkali salt, for example, sodium hydroxide, potassium hydroxide, lithium hydroxide and the like are used. Examples of the alkali metal carbonate include sodium carbonate, potassium carbonate, and lithium carbonate. In addition, pyridine, piperidine, trimethylamine, triethylamine, and the like, which are organic bases, can be used.

The temperature of hydroxy etherification is 0 degreeC or more and 100 degrees C or less, Preferably it is room temperature or more and 80 degrees C or less. If it is less than 0 ° C., the reaction rate is too slow and the reaction takes too much time, and if the temperature exceeds 100 ° C., side reactions occur and the purity of the product decreases. The reaction time is usually about 0.5 to 24 hours. As the reaction proceeds, crystals of the product precipitate, and the precipitate is filtered and dried to obtain a 9,10-bis (2-hydroxyalkoxy) anthracene compound.

Next, the third reaction will be described. Examples of the acylating agent used in the third reaction include acid anhydrides and acid halides. Examples of the acid anhydride include acetic anhydride, propionic anhydride, butyric anhydride, and examples of the acid halide include acetyl chloride, propionyl chloride, butyryl chloride, isobutyryl chloride, valeryl chloride, isovaleryl chloride, hexanoyl chloride, heptanoyl chloride, and chloride. Examples include benzoyl, p-toluoyl chloride, 1-naphthoyl chloride, 2-naphthoyl chloride, acetyl bromide, propionyl bromide, butyryl bromide, and benzoyl bromide.

When the acylating agent is an acid halide, the addition amount of the acylating agent to the 9,10-bis (2-hydroxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (2) is 2.0. It is more than mol times and less than 5 mol times, more preferably more than 2.2 mol times and less than 4 mol times. If it is less than 2.0 mol times, unreacted 9,10-bis (2-hydroxy-3-substituted oxypropoxy) anthracene compound remains in the product and the purity is lowered. Moreover, the yield is not improved even if it is added 5 mol times or more. On the other hand, when the acylating agent is an acid anhydride, it is preferably added in an amount of 2 moles or more. However, addition of more than 5 moles does not adversely affect the reaction. A large excess may be added.

In the third reaction, a basic compound is essential. As the basic compound, an organic basic compound is usually used. Examples of the organic basic compound include triethylamine, tributylamine, trihexylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine-butylamine, cyclohexylamine, pyridine, piperidine, γ-picoline, lutidine and the like.

The third reaction is usually performed in a solvent. The solvent used is not particularly limited as long as it does not react with acid anhydrides or acid halides. For example, aromatic solvents such as toluene, xylene and ethylbenzene, ether solvents such as tetrahydrofuran and 1,4-dioxane, acetone Ketone solvents such as methyl ethyl ketone, amide solvents such as dimethylacetamide and dimethylformamide, and halogenated carbon solvents such as methylene chloride, ethylene dichloride and chlorobenzene.

The reaction temperature for acylation is usually 0 ° C. or higher and lower than 100 ° C., preferably 20 ° C. or higher and lower than 60 ° C. If it is less than 0 ° C., the reaction time is too long, and if it is 100 ° C. or more, impurities are increased and the purity of the target compound is lowered, which is not preferable.

The reaction time in acylation varies depending on the reaction temperature, but is usually about 1 to 30 hours. More preferably, it is 3 hours to 10 hours.

In the third reaction, when the acylating agent is an acid halide after completion of the reaction, wash with water to remove the adduct of organic base hydrochloric acid or hydrobromic acid, and then concentrate and use a poor solvent such as alcohol or hexane. Recrystallize from When the acylating agent used is an acid anhydride, the product 9,10-bis (2-acyloxyalkoxy) anthracene compound precipitates when added to a poor solvent such as alcohol or hexane after completion of the reaction. The precipitated crystals may be filtered and dried as they are or after concentration. When the solvent used is water miscible, the product 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound precipitates when water is added after the reaction is completed. It may be filtered and dried.

(Photopolymerization sensitizer)
The 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention thus obtained is a photocationically polymerizable compound or a photoradically polymerizable compound. When polymerizing a photopolymerizable compound such as a photopolymerization initiator in the presence of a photopolymerization initiator, it can be used as a photocationic polymerization sensitizer or a photoradical polymerization sensitizer.

In addition, a photopolymerization sensitizer containing a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention is 9,10-bis (2- Acyloxy-3-substituted oxypropoxy) anthracene compound as an active ingredient, and the total amount thereof is 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound. As long as the above is not impaired, a photopolymerization sensitizer other than the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound may be included.

Examples of photopolymerization sensitizers other than such 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compounds include thioxanthone compounds (for example, 2-isopropylthioxanthone, 2,4-diethylthioxanthone), naphthalene compounds. (For example, 1,4-diethoxynaphthalene, 1,4-dimethoxynaphthalene, 1,4-dihydroxynaphthalene, 4-methoxy-1-naphthol), an amine compound (for example, methyl diethylaminobenzoate) and the like can be mentioned.

The addition ratio of the photopolymerization sensitizer other than the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound to the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound is particularly Although not limited, it is 0.1 to 10 times by weight with respect to the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound.

(Photopolymerization initiator)
Photopolymerization initiators include onium salts, benzylmethyl ketal photopolymerization initiators, α-hydroxyalkylphenone photopolymerization initiators, α-aminophenone photopolymerization initiators, acylphosphine oxide photopolymerization initiators, and oximes. Examples thereof include ester photopolymerization initiators and biimidazole photopolymerization initiators.

As the onium salt, an iodonium salt or a sulfonium salt is usually used. Examples of the iodonium salt include 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate, bis (dodecylphenyl) iodonium hexamethoxyantimonate, 4-isopropylphenyl-4′-methylphenyliodonium tetrakispentamethoxyphenylborate, 4- Examples thereof include isopropylphenyl-4′-methylphenyliodonium tetrakispentafluorophenylborate and the like. For example, IRGACURE 250 manufactured by BASF (Irgacure is a registered trademark of BASF), Solvay Japan PHOTOINITIATOR 2074 manufactured by the company can be used. On the other hand, examples of the sulfonium salt include S, S, S ′, S′-tetraphenyl-S, S ′-(4,4′-thiodiphenyl) disulfonium bishexamethoxyphosphate, diphenyl-4-phenylthiophenylsulfonium hexanium. Examples thereof include methoxyphosphate, triphenylsulfonium hexamethoxyphosphate, and the like, for example, UVI6992 manufactured by Dow Chemical Co., Ltd. or IRGACURE 270 manufactured by BASF (IRGACURE is a registered trademark of BASF Corporation). Etc. can be used. These photopolymerization initiators may be used alone or in combination of two or more.

Examples of the benzylmethyl ketal radical polymerization initiator include 2,2-dimethoxy-1,2-diphenylethane-1-one (trade name “Irgacure 651” manufactured by BSF Corporation). α-Hydroxyalkylphenone radical polymerization initiators include 2-hydroxy-2-methyl-1-phenylpropan-1-one (trade name “Darocur 1173” manufactured by BASF Corporation), 1-hydroxycyclohexyl phenyl ketone (product) Name “Irgacure 184” manufactured by BSF Corporation), 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one (trade name “Irgacure 2959” BSF Corporation) 2-hydroxy-1- {4- [4- (2-hydroxy-2-methylpropionyl) -benzyl] phenyl} -2-methyl-1-one (trade name “Irgacure 127” manufactured by BASF Corporation) ).

In particular, 2,2-dimethoxy-1,2-diphenylethane-1-one (trade name “Irgacure 651” manufactured by BASF), which is a benzylmethyl ketal radical polymerization initiator, and α-hydroxyalkylphenone radical polymerization initiation 2-hydroxy-2-methyl-1-phenylpropan-1-one (trade name “Darocur 1173” manufactured by BASF), 1-hydroxycyclohexyl phenylketone (trade name “Irgacure 184” manufactured by BASF) Is preferred.

Further, acetophenone radical polymerization initiators such as acetophenone, 2-hydroxy-2-phenylacetophenone, 2-ethoxy-2-phenylacetophenone, 2-methoxy-2-phenylacetophenone, 2-isopropoxy-2-phenylacetophenone, 2 -Isobutoxy-2-phenylacetophenone, benzyl radical polymerization initiator benzyl, 4,4'-dimethoxybenzyl, anthraquinone radical polymerization initiator 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-phenoxyanthraquinone 2- (phenylthio) anthraquinone, 2- (hydroxyethylthio) anthraquinone, and the like can also be used.

Of the illustrated photopolymerization initiators, onium salts are particularly preferable. As the onium salt, not only the iodonium salt but also the sulfonium salt, the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention is an optical compound. One of the characteristics is that it has a polymerization sensitizing effect.

The amount of the photopolymerization sensitizer containing the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention with respect to the photopolymerization initiator is particularly limited. However, it is usually in the range of 5 to 100% by weight, preferably in the range of 10 to 50% by weight with respect to the photopolymerization initiator. If the amount of the photopolymerization sensitizer used is less than 5% by weight, it takes too much time to photopolymerize the photopolymerizable compound. On the other hand, if the amount exceeds 100% by weight, an effect commensurate with the addition is obtained. Absent.

(Photopolymerization initiator composition)
The photopolymerization sensitizer containing the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention should be added directly to the photopolymerizable compound. However, it is also possible to prepare a photopolymerization initiator composition in advance by blending with a photopolymerization initiator and then add it to the photopolymerizable compound. That is, the photopolymerization initiator composition of the present invention contains at least a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1). And a photopolymerization initiator.

(Photopolymerizable composition)
A photopolymerizable composition can also be prepared by blending the photopolymerization initiator composition and a photopolymerizable compound. The photopolymerizable composition of the present invention comprises a photopolymerization sensitizer containing a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention, It is a composition containing a photopolymerization initiator composition containing a photopolymerization initiator and a photocationically polymerizable compound or a photoradical polymerizable compound.

The photopolymerization sensitizer containing the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention and the photopolymerization initiator are separately photocations. It may be added to the polymerizable compound or the photoradical polymerizable compound to form a photopolymerization initiator composition as a result in the photocationic polymerizable compound or the photoradical polymerizable compound.

Examples of the cationic photopolymerizable compound include epoxy compounds and vinyl ethers. Examples of general epoxy compounds include alicyclic epoxy compounds, epoxy-modified silicones, and aromatic glycidyl ethers. Examples of the alicyclic epoxy compound include 3 ′, 4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (3,4-epoxycyclohexyl) adipate, and the like, for example, UVR6105 manufactured by Dow Chemical Co., Ltd. UVR6110 etc. can be used. Examples of the epoxy-modified silicone include UV-9300 manufactured by Momentive Performance Materials. Examples of the aromatic glycidyl compound include 2,2'-bis (4-glycidyloxyphenyl) propane. Examples of the vinyl ether include methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether and the like. Of these photocationically polymerizable compounds, alicyclic epoxy compounds and epoxy-modified silicones are preferred in terms of film-forming ability and the like and the high solubility of the compounds of the present invention. These photocationically polymerizable compounds may be one kind or a mixture of two or more kinds.

As the photoradical polymerizable compound, for example, an organic compound having a double bond such as styrene, vinyl acetate, acrylic acid, methacrylic acid, acrylonitrile, methacrylonitrile, acrylamide, acrylic acid ester, and methacrylic acid ester can be used. . Among these photo-radically polymerizable compounds, in terms of film-forming ability and the like and the solubility of the compound of the present invention is high, acrylic acid esters and methacrylic acid esters (hereinafter referred to as (meth) acrylic acid esters together). ) Is preferred. (Meth) acrylic acid esters include methyl acrylate, butyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, isobornyl acrylate, methyl methacrylate, butyl methacrylate, methacrylic acid Examples include cyclohexyl, tetraethylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, epoxy acrylate, urethane acrylate, polyester acrylate, polybutadiene acrylate, polyol acrylate, polyether acrylate, silicone resin acrylate, and imide acrylate. These radical photopolymerizable compounds may be one kind or a mixture of two or more kinds.

In the photopolymerizable composition of the present invention, the amount of the photopolymerization initiator composition used is in the range of 0.005 wt% or more and 10 wt% or less, preferably 0.025 wt% with respect to the photopolymerizable composition. The content is 5% by weight or less. If it is less than 0.005% by weight, it takes time to photopolymerize the photopolymerizable composition. On the other hand, if it exceeds 10% by weight, the hardness of the photocured product obtained by photopolymerization decreases. This is not preferable because the physical properties of the cured product are deteriorated.

In addition, the photopolymerizable composition of the present invention has a diluent, a colorant, an organic or inorganic filler, a leveling agent, a surfactant, an antifoaming agent, a thickener, within a range not impairing the effects of the present invention. Various resin additives such as flame retardants, antioxidants, stabilizers, lubricants, and plasticizers may be blended.

(Photocured product)
A photocured product can be obtained by irradiating the photopolymerizable composition of the present invention with light. When the photopolymerizable composition is irradiated with light to be polymerized and photocured, the photopolymerizable composition can be formed into a film and photocured, or can be formed into a lump and photocured. In the case where it is molded into a film and photocured, the liquid photopolymerizable composition is applied to a substrate such as a polyester film so as to have a film thickness of 5 to 300 microns using a bar coater or the like. On the other hand, it can also be applied with a thinner or thicker film by spin coating or screen printing.

A photocured product is obtained by irradiating the coating film made of the photopolymerizable composition thus prepared with ultraviolet light having a wavelength range of 250 to 500 nm at an intensity of about 1 to 1000 mW / cm ^2. Can do. As a light source to be used, high pressure mercury lamp, ultra high pressure mercury lamp, metal halide lamp, xenon lamp, gallium doped lamp, black light, 395 nm ultraviolet LED, 385 nm ultraviolet LED, 365 nm ultraviolet LED, blue LED, white LED, D manufactured by Fusion Examples thereof include a valve and a V valve. Natural light such as sunlight can also be used. In particular, a 395 nm ultraviolet LED, a 385 nm ultraviolet LED, and a 365 nm ultraviolet LED are preferable.

(Tack free test)
As a method for determining whether or not the photopolymerizable composition of the present invention has been photocured, there is a tack free test. That is, when the photopolymerizable composition is irradiated with light, it cures and the surface is not tacky (stickiness). Therefore, by measuring the time from when the light is irradiated until tack (stickiness) disappears, the photocuring time Can be measured.

(Determination of migration resistance)
As a method for determining whether or not the photopolymerization sensitizer contained in the photopolymerizable composition of the present invention migrates to a film or the like, the photopolymerizable composition containing the photopolymerization sensitizer is a thin film. Create a product applied to the object, cover it with a polyethylene film, store it at a constant temperature (26 ° C) for a certain period of time, then peel off the polyethylene film, and examine whether the photopolymerization sensitizer has transferred to the polyethylene film The migration resistance was determined. The peeled polyethylene film was washed after washing the surface composition with acetone, measured for UV resistance of the polyethylene film, and measured for migration resistance by examining the increase in absorption intensity caused by the photopolymerization sensitizer. did. For the measurement, an ultraviolet / visible spectrophotometer (manufactured by Shimadzu Corporation, model: UV2200) was used. In order to quantitatively compare with 9,10-dibutoxyanthracene, which is the compound of the comparative example, the obtained absorbance was converted to the absorbance value of 9,10-dibutoxyanthracene. In conversion, the absorbance at 260 nm of the compound of the present invention and 9,10-dibutoxyanthracene was measured with an ultraviolet / visible spectrophotometer, the respective molar extinction coefficients were calculated from the absorbance value and molar concentration, and the ratio It converted using.

The present invention is illustrated by the following examples which are not intended to limit the scope of the invention. Unless otherwise specified, all parts are parts by weight. The product was confirmed based on the measurement by the following equipment.

(1) Melting point: Melting point measuring device manufactured by Gelen Camp, model MFB-595 (conforms to JIS K0064)
(2) Infrared (IR) spectrophotometer: Model IR-810 manufactured by JASCO Corporation
(3) Nuclear magnetic resonance apparatus (NMR): manufactured by JEOL Ltd., model GSX FT NMR Spectrometer

Synthesis Example 1 Synthesis of 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene 60 g of an aqueous sodium salt solution of 20 wt% anthrahydroquinone obtained in the same manner as in Synthesis Example 1 (0 as anthraquinone) 0.058 mol) was placed in an autoclave equipped with a stirrer in a nitrogen box and sealed. To this was added 23 g (0.18 mol) of butyl glycidyl ether dissolved in 30 ml of methanol under a nitrogen atmosphere. The reaction solution was heated for 1 hour at a temperature of 60 ° C., then cooled and the solid produced was filtered off. Next, the obtained solid was dissolved in 80 ml of dichloromethane and dehydrated with anhydrous sodium sulfate, and then 100 ml of methanol was added and stored in the refrigerator. After 2 days, crystals precipitated, and suction filtration and drying were performed to obtain 16.5 g (0.036 mol) of yellow 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene crystals. . The yield based on the starting 9,10-dihydroxyanthracene was 62 mol%.

(Synthesis Example 2) Synthesis of 9,10-bis (2-hydroxy-3-phenoxypropoxy) anthracene 20 g of an aqueous sodium salt solution of 20 wt% anthrahydroquinone obtained in the same manner as Synthesis Example 1 (0.019 mol as anthraquinone) Was dissolved in 40 ml of methanol. To this was added 7.5 g (0.05 mol) of phenyl glycidyl ether. After heating at 60 ° C. for 1 hour, the precipitated crystals were collected to obtain 6.2 g (0.012 mol) of 9,10-di (2-hydroxy-3-phenoxypropoxy) anthracene powder. The yield based on the starting 9,10-dihydroxyanthracene was 64 mol%.

(Synthesis Example 1) Synthesis of 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) in a 200 ml three-necked flask equipped with a stirrer in the same manner as in Synthesis Example 1 4.7 g (10 mmol) of 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene, 30 g of dimethylacetamide and 10.2 g (100 mmol) of acetic anhydride were obtained, and the resulting pale yellow color was obtained. A solution of 3.03 g (30 mmol) of triethylamine in 5 g of dimethylacetamide was added at room temperature. After heating at 50 ° C. for 5 hours, the obtained pale yellow reaction solution was added to 100 ml of 0.5% aqueous sulfuric acid solution. As a result, a yellow candy-like substance precipitated, and the supernatant liquid was discarded, and the precipitated candy-like substance was washed well with water, and gradually solidified. The solid was reslurried in methanol, filtered off with suction and dried to give 3.88 g (7.0 mmol) of a pale yellow crystalline powder of 9,10-bis [2-acetyloxy-3- (n-butoxy) propoxy] anthracene. ) The isolated yield based on the raw material 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene was 70 mol%.

(1) Melting point: 89-90 ° C
(2) IR (KBr, cm ⁻¹ ): 3060, 2960, 2935, 2880, 1729, 1398, 1369, 1344, 1230, 1169, 1117, 1096, 1053, 1019, 950, 773, 682, 651.
(3) ¹ H-NMR (CDCl ₃ , 400 Hz): δ 0.94 (t, J = 8 Hz, 6H), 1.36 to 1.46 (m, 4H), 1.58 to 1.66 (m, 4H), 2.20 (s, 6H), 3.56 (t, J = 8 Hz, 4H), 3.83-3.92 (m, 4H), 4.28-4.34 (m, 2H) 4.35-4.40 (m, 2H), 5.50-5.55 (m, 2H), 7.44-7.50 (m, 4H), 8.26-8.33 (m, 4H).

(Synthesis Example 2) Synthesis of 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene (Compound B) thermometer, 200 ml three-necked flask with stirrer was prepared in the same manner as in Synthesis Example 1. The synthesized 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene 4.7 g (10 mmol), dimethylacetamide 30 g, and propionic anhydride 9.1 g (70 mmol) were added to obtain. To a light yellow solution, a solution of 3.03 g (30 mmol) of triethylamine in 5 g of dimethylacetamide was added at room temperature. After heating at 50 ° C. for 5 hours, the obtained pale yellow reaction solution was added to 100 ml of 0.5% aqueous sulfuric acid solution. Then, a yellow candy-like substance precipitated, and the supernatant liquid was discarded, and the precipitated candy-like substance was washed well with water. Thereafter, the starch syrup was dried to obtain 3.2 g (5.5 mmol) of a light yellow starch syrup of 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene. The isolated yield based on the starting material 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene was 55 mol%.

(1) Melting point: room temperature water-like (2) IR (KBr, cm ⁻¹ ): 2955, 2925, 2870, 1736, 1350, 1184, 1168, 1113, 1064, 997, 768.
(3) ¹ H-NMR (CDCl ₃ , 400 Hz): δ 0.94 (t, J = 8 Hz, 6H), 1.23 (t, J = 8 Hz, 6H), 1.37-1.45 (m, 4H), 1.58-1.66 (m, 4H), 2.48 (q, J = 8 Hz, 4H), 3.52-3.61 (m, 4H), 3.82-3.93 ( m, 4H), 4.26-4.33 (m, 2H), 4.36-4.43 (m, 2H), 5.51-5.56 (m, 2H), 7.43-7. 50 (m, 4H), 8.27-8.33 (m, 4H).

Synthesis Example 3 Synthesis of 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene (Compound C) in a 200 ml three-necked flask equipped with a stirrer and in the same manner as in Synthesis Example 1 4.7 g (10 mmol) of 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene, 30 g of dimethylacetamide and 2.7 g (25 mmol) of butyryl chloride were added, and the resulting pale yellow color was obtained. To this solution was added 2.5 g (25 mmol) of triethylamine in 4 g of dimethylacetamide at room temperature. After heating at 50 ° C. for 5 hours, the obtained pale yellow reaction solution was added to 100 ml of 0.5% aqueous sulfuric acid solution. Then, a yellow candy-like substance precipitated, and the supernatant liquid was discarded, and the precipitated candy-like substance was washed well with water. Thereafter, the syrup was dried to obtain 3.9 g (6.4 mmol) of 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene pale yellow syrup. The isolated yield based on the raw material 9,10-bis [2-hydroxy-3- (n-butoxy) propoxy] anthracene was 64 mol%.

(1) Melting point: room temperature water-like (2) IR (KBr, cm ⁻¹ ): 2960, 2930, 2865, 1735, 1350, 1167, 1106, 1065, 998, 952, 768.
(3) ¹ H-NMR (CDCl ₃ , 400 Hz): δ 0.93 (t, J = 8 Hz, 6H), 1.01 (t, J = 8 Hz, 6H), 1.32-1.45 (m, 4H), 1.56-1.67 (m, 4H), 1.71-1.80 (m, 4H), 2.42 (t, J = 8 Hz, 4H), 3.51-3.62 ( m, 4H), 3.81-3.87 (m, 2H), 3.87-3.92 (m, 2H), 4.26-4.32 (m, 2H), 4.35-4. 41 (m, 2H), 5.50-5.56 (m, 2H), 7.42-7.50 (m, 4H), 8.26-8.33 (m, 4H).

(Synthesis Example 4) 9,10-bis (2-acetyloxy-3-phenoxypropoxy) anthracene (Compound D) synthesis thermometer, synthesized in the same manner as Synthesis Example 2 in a 200 ml three-necked flask equipped with a stirrer 1.8 g (3.6 mmol) of 10-bis (2-hydroxy-3-phenoxypropoxy) anthracene, 10 g of dimethylacetamide and 2.0 g (20 mmol) of acetic anhydride were added, and triethylamine was added to the resulting pale yellow solution. A solution of 1.0 g (10 mmol) of 2 g of dimethylacetamide was added at room temperature. After heating at 50 ° C. for 5 hours, the obtained pale yellow reaction solution was added to 100 ml of 0.5% aqueous sulfuric acid solution. Then, a yellow candy-like substance precipitated, and the supernatant liquid was discarded, and the precipitated candy-like substance was washed well with water. Thereafter, the starch candy was dried to obtain 0.94 g (1.6 mmol) of a light yellow candy of 9,10-bis (2-acetyloxy-3-phenoxypropoxy) anthracene. The isolated yield based on the raw material 9,10-bis (2-hydroxy-3-phenoxypropoxy) anthracene was 44 mol%.

(1) Melting point: room temperature candy form (2) IR (KBr, cm ⁻¹ ): 3060, 3030, 2920, 2875, 1739, 1495, 1224, 1068, 753, 691.
(3) ¹ H-NMR (CDCl ₃ , 400 Hz): δ 2.28 (s, 6H), 4.40-4.58 (m, 8H), 5.68-5.74 (m, 2H), 6 .98 (d, J = 9 Hz, 4H), 7.12-7.36 (m, 6H), 7.39-7.45 (m, 4H), 8.26-8.31 (m, 4H) .

(Evaluation Example 1) Photocationic polymerization using 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) As a cationically polymerizable compound, an alicyclic epoxy compound 3 ′, 100 parts of 4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (Celoxide 2021P, manufactured by Daicel), isobutylphenyl (4-methylphenyl) iodonium hexafluorophosphate (BAS as a photopolymerization initiator) -Irgacure 250 manufactured by F Corporation, "Irgacure" is a registered trademark of BSF Corporation, 4 parts, 9,10-bis [2-acetoxy- synthesized in Synthesis Example 1 as a photopolymerization sensitizer 3- (n-Butoxy) propoxy] anthracene (Compound A) 1 part is mixed to be photopolymerizable The Narubutsu was prepared. Using a bar coater (No. 12) on a 100 micron thick polyester film (Toray Lumirror, Lumirror is a registered trademark of Toray Industries, Inc.), the photopolymerizable composition is made to have a thickness of 18 microns. Applied. Then, the photocured material was obtained by irradiating light from the top using UV LED made from Phoseon. The central wavelength of the irradiation light is 395 nm and the irradiation intensity is 50 mW / cm ² . The stickiness (tack) of the coating film was confirmed by finger touch at regular intervals. The light irradiation time “tack free time” from the start of light irradiation until the tackiness of the coated surface of the composition disappeared was 1.3 seconds.

(Evaluation Example 2) 9,10-Bis [9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene (Compound B) as a cationic photopolymerization photopolymerization sensitizer 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy synthesized in the same manner as in Synthesis Example 2 instead of 2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) A photopolymerizable composition was prepared in the same manner as in Evaluation Example 1 except that anthracene (compound B) was used, and the photopolymerizable composition was applied and irradiated with light under the same conditions. The light irradiation time “tack free time” from the start of light irradiation until the sticking (tack) of the coated surface of the composition disappeared was 1.2 seconds.

(Evaluation Example 3) 9,10-bis [2 as a photocationic polymerization photosensitizer using 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene (compound C) 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene synthesized in the same manner as in Synthesis Example 3 instead of -acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) A photopolymerizable composition was prepared in the same manner as in Evaluation Example 1 except that (Compound C) was used, and the photopolymerizable composition was applied and irradiated with light under the same conditions. The light irradiation time “tack free time” from the start of light irradiation to the elimination of tackiness on the coated surface of the composition was 1.5 seconds.

(Evaluation Comparative Example 1) 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) as a cationic photopolymerization photosensitizer carried out without using a photopolymerization sensitizer The photopolymerizable composition was prepared in the same manner as in Evaluation Example 1 except that the photopolymerizable composition was applied and irradiated with light under the same conditions. ) Was confirmed by finger touch. However, tackiness did not disappear even after 30 seconds of light irradiation (it did not cure).

(Evaluation Comparative Example 2) 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy as a cationic polymerization photopolymerization sensitizer using 9,10-dibutoxyanthracene as a photopolymerization sensitizer A photopolymerizable composition was prepared in the same manner as in Evaluation Example 1 except that 9,10-dibutoxyanthracene (compound E) was used instead of anthracene (compound A), and the photopolymerizable composition was prepared under the same conditions. The object was applied and irradiated with light. The light irradiation time “tack free time” from the start of light irradiation to the elimination of tackiness on the coated surface of the composition was 1.0 second.

The results of Evaluation Examples 1 to 3 and Evaluation Comparative Examples 1 and 2 are shown in Table 1.

In addition, the compounds A, B, C and E which are photopolymerization sensitizers in Table 1 are compounds having the following structures.

(Evaluation Example 4) As a radical polymerizable radical polymerizable compound using 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A), pentaerythritol tetraacrylate (manufactured by Osaka Organic Chemical Co., Ltd.) 100 parts by weight of Biscoat 400), 2 parts of isobutylphenyl (4-methylphenyl) iodonium hexafluorophosphate (Irgacure 250 manufactured by BASF) as a photopolymerization initiator, and synthesized as a photopolymerization sensitizer A photopolymerizable composition was prepared by mixing 1 part of 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) synthesized in Example 1. Using the bar coater (No. 20) on the photopolymerizable composition on a 100 micron thick polyester film (Toray Lumirror, registered trademark of Toray Industries, Inc.) so that the film thickness becomes 30 microns. Applied. Then, the photocured material was obtained by irradiating light in the nitrogen atmosphere from the top using UV LED by Thunder. The central wavelength of the irradiation light was 395 nm and the irradiation intensity was 3 mW / cm ² . The stickiness (tack) of the coating film was confirmed by finger touch at regular intervals. The light irradiation time “tack free time” from the start of light irradiation until the tackiness of the coated surface of the composition disappeared was 10.0 seconds.

(Evaluation Example 5) As a radical polymerization photopolymerization sensitizer using 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene (Compound B), 9,10-bis [2 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy synthesized in the same manner as in Synthesis Example 2 instead of -acetyloxy-3- (n-butoxy) propoxy] anthracene (Compound A) A photopolymerizable composition was prepared in the same manner as in Evaluation Example 4 except that anthracene (compound B) was used, and the photopolymerizable composition was applied and irradiated with light under the same conditions. The light irradiation time “tack free time” from the start of light irradiation until the sticking (tack) of the coated surface of the composition disappeared was 8.0 seconds.

(Evaluation Example 6) As a radical polymerization photopolymerization sensitizer using 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene (compound C), 9,10-bis [2- 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene synthesized in the same manner as in Synthesis Example 3 instead of acetyloxy-3- (n-butoxy) propoxy] anthracene (Compound A) A photopolymerizable composition was prepared in the same manner as in Evaluation Example 4 except that (Compound C) was used, and the photopolymerizable composition was applied and irradiated with light under the same conditions. The light irradiation time “tack free time” from the start of light irradiation until the tackiness of the coated surface of the composition disappeared was 11.0 seconds.

(Evaluation Comparative Example 3) 9,10-bis [2-acetyloxy-3- (n-butoxy) propoxy] anthracene (Compound A) as a radical polymerization photopolymerization sensitizer carried out without using a photopolymerization sensitizer ) A photopolymerizable composition was prepared in the same manner as in Evaluation Example 4 except that it was not used, and the photopolymerizable composition was applied and irradiated with light under the same conditions. Was confirmed by finger touch. However, even after 60 seconds of light irradiation, tackiness (tack) did not disappear (it did not cure).

(Evaluation Comparative Example 4) As radical polymerization photopolymerization sensitizer using 9,10-dibutoxyanthracene as photopolymerization sensitizer, 9,10-bis [2-acetyloxy-3- (n-butoxy) Propoxy] A photopolymerizable composition was prepared in the same manner as in Evaluation Example 4 except that 9,10-dibutoxyanthracene (compound E) was used instead of anthracene (compound A), and photopolymerizable under the same conditions. The composition was applied and irradiated with light. The light irradiation time “tack free time” from the start of light irradiation until the tackiness of the coated surface of the composition disappeared was 9.0 seconds.

Table 2 shows the results of Evaluation Examples 4 to 6 and Evaluation Comparative Examples 3 and 4.

In addition, the compounds A, B, C and E which are photopolymerization sensitizers in Table 2 are compounds having the following structures.

From the results of Evaluation Examples 1 to 6 and Evaluation Comparative Examples 1 to 4 shown in Tables 1 and 2 above, the following is clear. That is, when the 9,10-bis [2-acyloxy-3- (n-butoxy) propoxy] anthracene compound of the present invention is used as a photopolymerization sensitizer and subjected to photo radical polymerization or photo cation polymerization, tack free From the test results, it can be seen that the photopolymerization sensitizing effect is excellent and the photopolymerization sensitizing ability is equivalent to that of 9,10-dibutoxyanthracene, which is a known photopolymerization sensitizer.

(Evaluation Example 7) Evaluation of migration resistance when 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) is used as a photopolymerization sensitizer Cationic polymerization As a compound, 100 parts of alicyclic epoxy compound 3 ′, 4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (Celoxide 2021P manufactured by Daicel) was synthesized in Synthesis Example 1 as a photopolymerization sensitizer. 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) 2 parts were mixed, and the prepared composition was a 100 micron-thick polyester film (Toray Lumirror, Lumirror Using a bar coater (No. 12) on top of the registered trademark of the corporation, so that the film thickness becomes 18 microns. Coated. Next, a low-density polyethylene film (film thickness 30 microns) was placed on the obtained coating, and stored for one day in a dark place, stored for three days, and then stored, and then the low-density polyethylene film was peeled off. After the low density polyethylene film was washed with acetone and dried, the UV spectrum of the low density polyethylene film was measured, and the absorbance at 260 nm was measured. The absorbance of 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene obtained from the measurement results was converted to 9,10-dibutoxyanthracene. The absorbance was 0.017 after storage for one day and 0.015 after storage for three days.

(Evaluation Example 8) Evaluation of migration resistance when 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene (Compound B) is used as a photopolymerization sensitizer Photopolymerization Instead of 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (compound A) as a sensitizer, 9,10-bis [2- A composition was prepared in the same manner as in Evaluation Example 7 except that propionyloxy-3- (n-butoxy) propoxy] anthracene (compound B) was used, and the absorbance at 260 nm of the low-density polyethylene film washed with acetone was measured. It was measured. The absorbance of 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene obtained from the measurement results was converted to 9,10-dibutoxyanthracene. The absorbance was 0.016 after one day storage and 0.015 after three days storage.

(Evaluation Example 9) Evaluation of migration resistance when 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene (Compound C) was used as a photopolymerization sensitizer 9,10-bis [2-butyryloxy synthesized in the same manner as in Synthesis Example 3 instead of 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) as a sensitizer. A composition was prepared in the same manner as in Evaluation Example 7 except that -3- (n-butoxy) propoxy] anthracene (Compound C) was used, and the absorbance at 260 nm of a low-density polyethylene film washed with acetone was measured. . The absorbance of 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene obtained from the measurement results was converted to 9,10-dibutoxyanthracene. The absorbance was 0.013 after one day storage and 0.012 after three days storage.

(Comparative Example 5) Evaluation of migration resistance when 9,10-dibutoxyanthracene (Compound E) was used as a photopolymerization sensitizer 9,10-bis [2-acetoxy- 3- (n-Butoxy) propoxy] anthracene (Compound A) instead of 9,10-dibutoxyanthracene (Compound E), a composition was prepared in the same manner as in Evaluation Example 7, and acetone was added. The absorbance of the washed low density polyethylene film at 260 nm was measured. The absorbance of 9,10-dibutoxyanthracene was 1.48 after 1 day storage and 1.49 after 3 days storage.

Table 3 shows the results of Evaluation Examples 7 to 9 and Evaluation Comparative Example 5.

In addition, the compounds A, B, C and E which are photopolymerization sensitizers in Table 3 are compounds having the following structures.

(Evaluation Example 10) Evaluation of migration resistance when 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) is used as a photopolymerization sensitizer Radical polymerization As a compound, 100 parts of trimethylolpropane triacrylate, and 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene synthesized in the same manner as in Synthesis Example 1 as a photopolymerization sensitizer ( Compound A) 2 parts are mixed and the prepared composition is placed on a polyester film having a film thickness of 100 microns (Toray Lumirror, Lumirror is a registered trademark of Toray Industries, Inc.) so that the film thickness is 30 microns. Applied. Next, a low-density polyethylene film (film thickness of 30 microns) is placed on the obtained coating, and after storing for one day and one for three days in the dark, the low-density polyethylene film is peeled off, After the low density polyethylene film was washed with acetone and dried, the UV spectrum of the low density polyethylene film was measured, and the absorbance at 260 nm was measured. The absorbance of 9,10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene obtained from the measurement results was converted to 9,10-dibutoxyanthracene. The absorbance was 0.037 after one day storage and 0.034 after three days storage.

(Evaluation Example 11) Evaluation of migration resistance when 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene (Compound B) was used as a photopolymerization sensitizer 9, 9,10-bis [2-propionyloxy-3- (n) synthesized in the same manner as in Synthesis Example 2 instead of 10-bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) -Butoxy) propoxy] A composition was prepared in the same manner as in Evaluation Example 10 except that anthracene (Compound B) was used, and the absorbance of a low-density polyethylene film washed with acetone was measured at 260 nm. The absorbance of 9,10-bis [2-propionyloxy-3- (n-butoxy) propoxy] anthracene obtained from the measurement results was converted to 9,10-dibutoxyanthracene. The absorbance was 0.038 after one day storage and 0.036 after three days storage.

(Evaluation Example 12) Evaluation of migration resistance when 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene (Compound C) was used as a photopolymerization sensitizer 9,10 9,10-bis [2-butyryloxy-3- (n-butoxy) synthesized in the same manner as in Synthesis Example 3 instead of -bis [2-acetoxy-3- (n-butoxy) propoxy] anthracene (Compound A) ) Propoxy] A composition was prepared in the same manner as in Evaluation Example 10 except that anthracene (Compound C) was used, and the absorbance at 260 nm of the acetone-washed low density polyethylene film was measured. The absorbance of 9,10-bis [2-butyryloxy-3- (n-butoxy) propoxy] anthracene obtained from the measurement results was converted to 9,10-dibutoxyanthracene. Absorbance was 0.046 after 1 day storage and 0.044 after 3 days storage.

(Evaluation Comparative Example 6) Evaluation of migration resistance when 9,10-dibutoxyanthracene (Compound E) is used as a photopolymerization sensitizer 9,10-bis [2-acetoxy-3- (n-butoxy) ) Propoxy] low density polyethylene film prepared in the same manner as in Evaluation Example 10 except that 9,10-dibutoxyanthracene (Compound E) is used instead of anthracene (Compound A) and washed with acetone The absorbance at 260 nm was measured. Absorbance was 2.54 after 1 day storage and 2.49 after 3 days storage.

Table 4 shows the results of Evaluation Examples 10 to 12 and Evaluation Comparative Example 6.

In addition, the compounds A, B, C and E which are photopolymerization sensitizers in Table 3 are compounds having the following structures.

From Tables 3 and 4, the following is clear. That is, the photopolymerization sensitizer containing the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the general formula (1) of the present invention has a very high degree of migration to a polyethylene film. It can be seen that the migration resistance is low. On the other hand, 9,10-dibutoxyanthracene, which is a known photopolymerization sensitizer, was observed to have high migration to a polyethylene film in the same test.

From the above results, the 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound of the present invention is a known photopolymerization sensitizer in photocationic polymerization and photoradical polymerization. Compared with the dibutoxyanthracene compound, it is an excellent compound that not only has the same photopolymerization sensitizing ability but also has high migration resistance, and is extremely useful as a photopolymerization sensitizer.

Claims (6)

A 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (1).

(In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents 1 to 8 carbon atoms. X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.) The 9,10-bis (2-hydroxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (2) is acylated by reacting with an acylating agent. ) 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the following formula.

(In General Formula (2), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and X and Y are the same. And may be different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.)

(In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents 1 to 8 carbon atoms. X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.) A photopolymerization sensitizer containing a 9,10-bis (2-acyloxy-3-substituted oxypropoxy) anthracene compound represented by the following general formula (1).

(In the general formula (1), A represents an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms or an aryloxymethyl group having an aryl group having 6 to 10 carbon atoms, and B represents 1 to 8 carbon atoms. X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.) A photopolymerization initiator composition comprising the photopolymerization sensitizer according to claim 3 and a photopolymerization initiator. A photopolymerizable composition comprising the photopolymerization initiator composition according to claim 4 and a photopolymerizable compound. A curing method, wherein the photopolymerizable composition according to claim 5 is cured by irradiating the photopolymerizable composition with energy rays containing light having a wavelength in the range of 250 nm to 500 nm.