Novel compound

Abstract

To provide a bifunctional light-absorbing monomer usable as a monomeric raw material for a polymer compound.SOLUTION: Specifically, a compound having the following structural formula is exemplified.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound having two polymerizable functional groups and two photoabsorbing triazine derivatives.

Background Art

[0002] A light absorber has a function of absorbing light by a chemical mechanism and converting it into other energy such as heat. By utilizing this function, weather resistance can be imparted by adding it to a synthetic resin that causes deterioration or discoloration by light. On the other hand, there are cases where it is added to a synthetic resin in order to intentionally alter the surrounding synthetic resin by generating heat when irradiated with light.

[0003] As an example of intentionally altering the surrounding synthetic resin by light irradiation, a temporary adhesive material for semiconductor processing that peels off by light is mentioned. The temporary adhesive material for semiconductor processing is used to prevent the semiconductor substrate from being damaged in processes such as back grinding, TSV, and back electrode formation by bonding the semiconductor substrate to a support such as silicon or glass via an adhesive layer. The semiconductor substrate bonded by the adhesive must be easily peeled off at the final stage of the semiconductor processing step. In order to provide this peelability, a method of adding a light absorber to the adhesive layer is often adopted.

[0004] Patent Document 1 discloses a temporary adhesive material using such a semiconductor temporary adhesive. That is, a temporary adhesive material composed of an adhesive component and a light absorption component and peelable by light irradiation is disclosed.

[0005] However, as described in Patent Document 1, these added light absorption components are often added as a single substance, and when exposed to an organic solvent during the semiconductor component manufacturing process, the light absorption components elute, and there are cases where the original peeling function of the light absorption components cannot be maintained.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] The present invention has been made in view of the above circumstances, and an object thereof is to provide a bifunctional light-absorbing monomer that can be used as a monomer raw material for a polymer compound.

Means for Solving the Problems

[0008] In order to solve the above problems, in the present invention, the following general formula (1):

Chemical formula

Chemical formula

[0009] If it is a compound of the present invention, it is possible to provide a bifunctional light-absorbing monomer that can be used as a monomer raw material for a polymer compound having two polymerizable functional groups and two light-absorbing triazine derivatives.

[0010] The compound of the present invention is preferably a light-absorbing compound.

[0011] If the compound of the present invention is a light-absorbing compound, for example, by using it as a temporary adhesive material for semiconductor processing, the light-absorbing component will not elute even when exposed to an organic solvent, and the peeling function can be maintained.

[0012] Furthermore, it is preferable that the compound of the present invention has at least one maximum absorption wavelength λmax of light between 200 nm and 1000 nm.

[0013] For such a compound of the present invention, for example, by using it as a temporary adhesive material for semiconductor processing, in the semiconductor processing step, the semiconductor substrate bonded by an adhesive can be easily peeled off by light irradiation.

Advantages of the Invention

[0014] As described above, according to the present invention, a compound having two polymerizable functional groups and two light-absorbing triazine derivatives can be provided. For the compound of the present invention, by using it as a temporary adhesive material for semiconductor processing, the light-absorbing component will not elute even when exposed to an organic solvent, and the peeling function can be maintained. Thereby, the semiconductor substrate bonded by an adhesive can be easily peeled off by light irradiation at the final stage of the semiconductor processing step.

Modes for Carrying Out the Invention

[0015] As described above, there has been a demand for the development of a compound that can maintain the peeling function without eluting the light-absorbing component even when exposed to an organic solvent.

[0016] As a result of intensive studies on the above problems, the present inventors have found a compound having two polymerizable functional groups and two light-absorbing triazine derivatives, and completed the present invention.

[0017] That is, the present invention is the following general formula (1):

Chemical formula

[0018] Hereinafter, the present invention will be described in detail, but the present invention is not limited thereto.

[0019] The compound having two polymerizable functional groups and two photoabsorbing triazine derivatives of the present invention is represented by the above general formula (1), and in formula (1), V is [Chemical formula] is a divalent organic group selected from any of the following, and p is 0 or 1. Also, R 1 and R 2 and R 3 are each a hydrogen atom or a hydroxy group, an oxyalkyl group or an alkyl group, and at least one of R 1 and R 3 is a hydroxy group.

[0020] Examples of the oxyalkyl group include hydrocarbon groups having 1 to 7 carbon atoms such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, neopentyloxy group, hexyloxy group, and heptyloxy group, and a typical one is methoxy group.

[0021] Examples of the alkyl group include alkyl groups having 1 to 7 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, and heptyl group, and a more typical one is the methyl group.

[0022] As the compound represented by such general formula (1), representative examples include the compounds of the following formulas (2) - (13).

[0023]

Chemical formula

[0024]

Chemical formula

[0025]

Chemical formula

[0026]

Chemical formula

[0027]

Chemical formula

[0028]

Chemical formula

[0029]

Chemical formula

[0030]

Chemical formula

[0031] [Chemistry]

[0032] [Chemistry]

[0033] [Chemistry]

[0034] [Chemistry]

[0035] [Method for Producing the Compound of the Present Invention] The compound of general formula (1) is obtained by reacting the diallyl - diglycidyl ether compound (14) shown below with [Chemistry] (In formula (14), V is [Chemistry] a divalent organic group selected from any of the above, and p is 0 or 1.) It can be obtained by reacting 2 equivalents of the compound represented by the following general formula (15). [Chemistry] (R 1 , R 2 and R 3 are each a hydrogen atom, a hydroxy group, an oxyalkyl group or an alkyl group, and at least one of R 1 and R 3 is a hydroxy group.)

[0036] The compound represented by the general formula (1) can be obtained by adding a base to 2 equivalents of the compound represented by the general formula (15) dissolved in a solvent, stirring, and then adding 1 equivalent of a diallyl-diglycidyl ether compound (14) and heating with stirring.

[0037] The above solvent is not particularly limited, but an aprotic organic solvent is preferred, and examples include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloroethane, chloroform, and chlorobenzene; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylpropionamide, N-methylpyrrolidone, and N-ethylpyrrolidone; and sulfoxides such as dimethyl sulfoxide.

[0038] The amount of the above solvent is not particularly limited, but it is preferably an amount sufficient to sufficiently dissolve the compound represented by the general formula (1). It is preferably 0.30 M or less, more preferably 0.25 M or less, and even more preferably 0.20 M, based on the compound represented by the general formula (1).

[0039] The above base is not particularly limited, but those with an acid dissociation constant (pKa) greater than that of phenols are preferred, and examples include aliphatic amines such as triethylamine, diazabicyclononene, and diazabicycloundecene; heterocyclic amines such as pyridine and N,N-dimethylaminopyridine; ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide; carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; and inorganic salts such as lithium hydroxide, sodium hydroxide, and potassium hydroxide.

[0040] The equivalent amount of the above base is not particularly limited, but it is preferably 1 equivalent or more, more preferably 1.5 equivalents or more, and most preferably 2 equivalents or more.

[0041] The heating temperature is not particularly limited, but is preferably from 25°C to 180°C, more preferably from 100°C to 160°C, and the reaction time is about 2 to 30 hours, preferably 5 to 7 hours.

[0042] After completely distilling off the reaction solvent by distillation under reduced pressure for these reaction products, an organic solvent and an acidic aqueous solution are added to make the inside of the reaction system have a pH of less than 7. Next, the acidic aqueous layer is removed, a water washing step with pure water is carried out, and the used solvent is sufficiently removed by distillation under reduced pressure to obtain the target compound of general formula (1).

[0043] The organic solvent to be added is not particularly limited, and examples include aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as normal pentane, normal hexane, cyclopentane, and cyclohexane, and halogenated hydrocarbons such as dichloroethane, chloroform, and chlorobenzene. In particular, it is preferable to use toluene.

[0044] The acidic aqueous solution used when making the inside of the reaction system have a pH of less than 7 is not particularly limited, and examples include dilute sulfuric acid, dilute nitric acid, hydrochloric acid, acetic acid, ammonium chloride aqueous solution, etc., but it is preferable to use divalent dilute sulfuric acid.

Examples

[0045] Hereinafter, the present invention will be specifically described using examples and comparative examples, but the present invention is not limited thereto.

[0046] [Examples] Into a 5-liter separable flask equipped with a thermometer and a Dimroth condenser, the following formula (16)

Chemical formula

Chemical formula

[0047] When 1H nuclear magnetic resonance spectrum analysis of the obtained compound was performed, it was confirmed that the target compound (2) in which 2 equivalents of the phenol compound (16) reacted with the 2,2'-diallylbisphenol A compound (17) and the epoxy ring was opened. The results of 1H-NMR are shown in Table 1.

[0048]

Table 1

Chemical formula

[0049] In addition, when the absorbance of the obtained compound (2) was measured using an ultraviolet-visible spectrophotometer (UV-3600iPlus manufactured by SHIMAZDU Corporation) in the light wavelength range of 200 nm to 1000 nm, the maximum absorption wavelengths λmax were 288 nm and 338 nm.

[0050] As described above, it has been found that the compound of the present invention can provide a compound having two polymerizable reactive functional groups available for polymer synthesis and two photoabsorbing triazine derivatives. By incorporating the compound into the polymer of the semiconductor temporary bonding material, the photoabsorbing component does not elute even when exposed to an organic solvent, and the peeling function can be maintained. It is expected that the semiconductor substrate bonded by the temporary bonding material can be easily peeled at the final stage of the semiconductor processing step by light irradiation.

[0051] Note that the present invention is not limited to the above-described embodiment. The above-described embodiment is an example, and any configuration that has substantially the same configuration as the technical idea described in the claims of the present invention and exhibits the same operational effects is included in the technical scope of the present invention.

Claims

1. The following general formula (1): 【Chemical 1】 (In formula (1), V is 【Chemical 2】 is a divalent organic group selected from any of them, and p is 0 or 1. Also, R １ , R ２ and R ３ are each a hydrogen atom, a hydroxy group, an oxyalkyl group or an alkyl group, and at least one of R １ and R ３ is a hydroxy group.) A compound characterized in that it is represented by.

2. The compound according to claim 1, characterized in that the compound is a light-absorbing compound.

3. The compound according to claim 2, characterized in that there is at least one maximum absorption wavelength λmax of light between 200 nm and 1000 nm.

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