Novel compounds

Abstract

The present invention addresses the problem of providing a bifunctional light-absorbing monomer that can be used as a monomer starting material for a polymer compound. [Solution] A compound characterized by being represented by general formula (1): # imgabs0 # (in formula (1), V is any divalent organic group selected from the group consisting of the following groups, and p is 0 or 1; in addition, R1, R2, and R3 are each a hydrogen atom, a hydroxyl group, an alkoxy group, or an alkyl group, and at least one of R1 and R3 is a hydroxyl group. # imgabs1 #

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 the function of absorbing light through a chemical mechanism and converting it into other energy such as heat. By utilizing this function and adding it to a synthetic resin that deteriorates or changes color due to light, weather resistance can be imparted. On the other hand, there is also a case where it is added to a synthetic resin to generate heat by irradiating light, and thereby intentionally denature the surrounding synthetic resin.

[0003] As an example of intentionally denaturing the surrounding synthetic resin by light irradiation, a temporary adhesive material for semiconductor processing that uses light for peeling can be cited. The temporary adhesive material for semiconductor processing is used to prevent breakage of a semiconductor substrate in processes such as back grinding, TSV (through-silicon via), or back electrode formation by bonding the semiconductor substrate to a support such as silicon or glass via an adhesive layer. The semiconductor substrate bonded with an adhesive needs to be easily peeled off at the final stage of the semiconductor processing step. To impart this peelability, a method of adding a light absorber to the adhesive layer is often employed.

[0004] Patent Document 1 describes a temporary adhesive material using the above-mentioned semiconductor temporary adhesive. That is, it describes a temporary adhesive material composed of an adhesive component and a light-absorbing component that can be peeled off by light irradiation.

[0005] However, as described in Patent Document 1, the above-mentioned added light-absorbing component is often added in the form of a single substance, and when exposed to an organic solvent in the semiconductor component manufacturing process, there is a case where the light-absorbing component dissolves out and the original peeling function of the light-absorbing component cannot be maintained.

[0006] Prior Art Documents

[0007] Patent Documents

[0008] Patent Document 1: International Publication No. 2020 / 105586 Summary of the Invention

[0009] (I) Technical Problems to be Solved

[0010] In view of the above circumstances, the present invention has been completed, and its object is to provide a bifunctional photoabsorbing monomer that can be used as a monomer raw material for a polymer compound.

[0011] (II) Technical Solution

[0012] To solve the above technical problems, the present invention provides a compound represented by the following general formula (1):

[0013]

[0014] In formula (1), V is a divalent organic group selected from any one of the following groups, and p is 0 or 1; in addition, R 1 , R 2 and R 3 are a hydrogen atom, a hydroxyl group, an alkoxy group or an alkyl group respectively, and at least one of R 1 and R 3 is a hydroxyl group,

[0015] .

[0016] If it is a compound of the present invention, a bifunctional photoabsorbing monomer can be provided, which can be used as a monomer raw material for a polymer compound having two polymerizable functional groups and two photoabsorbing triazine derivatives.

[0017] The compound of the present invention is preferably a photoabsorbing compound.

[0018] If the compound of the present invention is a photoabsorbing compound, for example, by using it as a temporary adhesive material for semiconductor processing, even when exposed to an organic solvent, the photoabsorbing component will not dissolve out, and the peeling function can be maintained.

[0019] Furthermore, the compound of the present invention preferably has at least one maximum absorption wavelength λmax of light between 200 nm and 1000 nm.

[0020] If it is such a compound of the present invention, for example, by using it as a temporary adhesive material for semiconductor processing, in the semiconductor processing process, the semiconductor substrate bonded with an adhesive can be simply peeled off by light irradiation.

[0021] (III) Beneficial effects

[0022] As described above, according to the present invention, a compound having two polymerizable functional groups and two photoabsorbing triazine derivatives can be provided. If it is a compound of the present invention, by using it as a temporary adhesive material for semiconductor processing, even when exposed to an organic solvent, the photoabsorbing component will not dissolve out, and the peeling function can be maintained. Thus, at the final stage of the semiconductor processing process, the semiconductor substrate bonded with an adhesive can be simply peeled off by light irradiation. Detailed implementation manners

[0023] As described above, there is a need to develop a compound in which the photoabsorbing component will not dissolve out even when exposed to an organic solvent and the peeling function can be maintained.

[0024] The inventors of the present application have conducted in-depth research on the above technical problems and as a result, discovered a compound having two polymerizable functional groups and two photoabsorbing triazine derivatives, thus completing the present invention.

[0025] That is, the present invention is a compound represented by the following general formula (1):

[0026]

[0027] In formula (1), V is a divalent organic group selected from any of the following groups, and p is 0 or 1; in addition, R 1 , R 2 and R 3 are each a hydrogen atom, a hydroxyl group, an alkoxy group or an alkyl group, and at least one of R 1 and R 3 is a hydroxyl group.

[0028] .

[0029] The following provides a detailed description of the present invention, but the present invention is not limited thereto.

[0030] The compound of the present invention having two polymerizable functional groups and two photoabsorbing triazine derivatives is represented by the above general formula (1), where V in formula (1) is a divalent organic group selected from any of the following groups, and p is 0 or 1. In addition, R 1 , R 2 and R 3 are each a hydrogen atom or a hydroxyl group, an alkoxy group or an alkyl group, and at least one of R 1 and R 3 is a hydroxyl group.

[0031] .

[0032] Examples of the alkoxy group include hydrocarbon groups having 1 to 7 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, neopentyloxy, hexyloxy, and heptyloxy, and a more representative alkoxy group is methoxy.

[0033] Examples of the alkyl group include alkyl groups having 1 to 7 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, and heptyl, and a more representative alkyl group is methyl.

[0034] As a compound represented by such a general formula (1), representative examples include compounds of the following formulas (2) to (13).

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047] [Preparation method of the compound of the present invention]

[0048] The compound of general formula (1) can be obtained by reacting the diallyl - diglycidyl ether compound (14) shown below with a compound represented by the following general formula (15) in an amount of 2 equivalents relative to the compound (14).

[0049]

[0050] In formula (14), V is a divalent organic group selected from any of the following groups, and p is 0 or 1.

[0051]

[0052]

[0053] R 1 、R 2 and R 3 are each a hydrogen atom, a hydroxyl group, an alkoxy group or an alkyl group, and at least one of R 1 and R 3 is a hydroxyl group.

[0054] The compound represented by general formula (1) can be obtained by adding a base to 2 equivalents of the compound represented by general formula (15) dissolved in a solvent, stirring, then adding 1 equivalent of the diallyl - diglycidyl ether compound (14) and heating with stirring.

[0055] The above-mentioned solvent is not particularly limited, but a non-protic organic solvent is preferred, and examples thereof 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-dimethylpropanamide, N-methylpyrrolidone, and N-ethylpyrrolidone; and sulfoxides such as dimethyl sulfoxide, etc.

[0056] The amount of the above-mentioned solvent is not particularly limited, but it is preferably an amount that can fully dissolve the compound represented by the general formula (1). Relative to the compound represented by the general formula (1), it is preferably 0.30 M or less, more preferably 0.25 M or less, and still more preferably 0.20 M or less.

[0057] The above-mentioned base is not particularly limited, but a base with an acid dissociation constant ( pKa ) greater than that of phenols is preferred, and examples thereof include: aliphatic amines such as triethylamine, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,8-diazabicyclo[5.4.0]undec-7-ene; heterocyclic amines such as pyridine or 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, etc.

[0058] The equivalent amount of the above-mentioned 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.

[0059] The heating temperature is not particularly limited, but it is preferably 25°C to 180°C, more preferably 100°C to 160°C, and the reaction time is about 2 to 30 hours, preferably 5 to 7 hours.

[0060] For the reaction product of the above-mentioned substances, after completely distilling off the reaction solvent under reduced pressure, an organic solvent and an acidic aqueous solution are added to make the pH in the reaction system less than 7. Then, the acidic aqueous layer is removed, and a water washing process is carried out with pure water, and the solvent used is sufficiently removed by reduced pressure distillation, whereby the general formula (1) as the target compound can be obtained.

[0061] The organic solvent to be added is not particularly limited, and examples thereof include: aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, cyclopentane, and cyclohexane; and halogenated hydrocarbons such as dichloroethane, chloroform, and chlorobenzene, etc. Toluene is particularly preferably used.

[0062] The acidic aqueous solution used to make the pH in the reaction system less than 7 is not particularly limited, and examples thereof include dilute sulfuric acid or dilute nitric acid, hydrochloric acid, acetic acid, ammonium chloride aqueous solution, etc., but dilute sulfuric acid of divalent is preferably used.

[0063] Example

[0064] The present invention will be specifically described below using examples and comparative examples, but the present invention is not limited thereto.

[0065] [Example]

[0066] 238.5 g (600 mmol) of the phenolic compound represented by the following formula (16) (R in the general formula (1) 1 = OH, R 2 = Me, R 3 = Me) was added to a 5 L separable flask equipped with a thermometer and a Dimroth type condenser, and 3000 mL of N,N-dimethylformamide as a solvent and 170.0 g (1230 mmol) of potassium carbonate as a base were added, and the mixture was stirred at room temperature for 30 minutes. Then, 126.2 g (300 mmol) of the 2,2'-diallylbisphenol A compound (17) was added and heated at 140 °C for 6 hours to cause a reaction. After completion of the reaction, N,N-dimethylformamide was sufficiently removed at 100 °C by distillation under reduced pressure, 1500 mL of toluene and 2000 mL of pure water were added and stirred. While cooling the reaction solution with ice, 3M dilute sulfuric acid was added dropwise until the pH became less than 7. The aqueous layer was removed, and the washing operation with pure water was carried out until the pH became about 7, and toluene was completely removed by distillation under reduced pressure to obtain 360.9 g (297 mmol) of the target compound (2). The target compound (2) was a red-brown viscous substance.

[0067]

[0068]

[0069] The obtained compound was analyzed by 1H nuclear magnetic resonance spectroscopy, and as a result, it was confirmed that the obtained compound was the target compound (2) in which the 2,2'-diallylbisphenol A compound (17) reacted with 2 equivalents of the phenolic compound (16) relative to the compound (17) and the epoxy group was ring-opened. The results of 1H-NMR are shown in Table 1.

[0070] [Table 1]

[0071]

[0072]

[0073] In addition, using a UV-visible spectrophotometer (manufactured by Shimadzu Corporation, UV-3600iPlus), the absorbance of the obtained compound (2) was measured in the light wavelength region of 200 nm to 1000 nm, and as a result, the maximum absorption wavelengths λmax were 288 nm and 338 nm.

[0074] As described above, it can be understood that the compound according to the present invention can provide a compound having two polymerizable functional groups and two light-absorbing triazine derivatives that can be used in polymer synthesis. By introducing the compound into the polymer of the semiconductor temporary adhesive material, it can be expected that: even when exposed to an organic solvent, the light-absorbing component will not dissolve out, and the peeling function can be maintained; at the final stage of the semiconductor processing step, the semiconductor substrate bonded using the temporary adhesive material can be simply peeled by light irradiation.

[0075] In addition, the present invention is not limited to the above-described embodiments. The above-described embodiments are examples, and any technical solutions having a configuration substantially the same as the technical concept described in the claims of the present invention and exhibiting the same technical effects are included in the technical scope of the present invention.

Claims

1. A compound, characterized in that It is represented by the following general formula (1): In formula (1), V is a divalent organic group selected from any one of the following groups, p is 0 or 1; and R 1 , R 2 and R 3 are hydrogen atoms, hydroxyl groups, alkoxy groups or alkyl groups, R 1 With R 3 At least one of them is a hydroxyl group, 。 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 It has at least one maximum absorption wavelength λmax of light between 200nm and 1000nm.

Images