Radically curable compound, method for producing radically curable compound, radically curable composition, cured product of the same, and resist-material composition

Patent metadata

Field	Value
Publication number	US-9550723-B2
Application number	US-201615259787-A
Country	US
Kind code	B2
Filing date	Sep 8, 2016
Priority date	Jul 25, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

Provided is a positive photoresist composition excellent in terms of heat resistance. A radically curable compound is represented by a general formula (1) below (where R 1 , R 2 , and R 3 each independently represent an alkyl group having 1 to 8 carbon atoms; m and n each independently represent an integer of 1 to 4; p represents an integer of 0 to 4; X, Y, and Z each independently represent an acryloyloxy group, a methacryloyloxy group, or a hydroxy group, and at least one of X, Y, and Z represents an acryloyloxy group or a methacryloyloxy group; and t represents 1 or 2).

First claim

The invention claimed is:

1. A method for producing a radically curable compound, comprising causing polycondensation between an alkyl-substituted phenol (a1) and an aromatic aldehyde (a2) having a hydroxy group on a benzene ring to prepare a polycondensate (A) represented by a general formula (3) below

(where R 1 , R 2 , and R 3 each independently represent an alkyl group having 1 to 8 carbon atoms; m and n each independently represent an integer of 1 to 4; p represents an integer of 0 to 4; and s represents 1 or 2); and
subsequently causing a reaction between the polycondensate and a (meth)acrylic acid halide (B).

2. The method for producing a radically curable compound according to claim 1 , wherein the alkyl-substituted phenol (a1) is 2,5-xylenol or 2,6-xylenol.

3. The method for producing a radically curable compound according to claim 1 , wherein the aromatic aldehyde (a2) having a hydroxy group on a benzene ring is a 4-hydroxybenzaldehyde.

4. The method for producing a radically curable compound according to claim 1 , comprising a step 1 of causing polycondensation between the alkyl-substituted phenol (a1) and the aromatic aldehyde (a2) having a hydroxy group on a benzene ring in the presence of an acid catalyst to prepare a crude product containing the polycondensate (A) in a reaction solution; a step 2 of collecting from the reaction solution the polycondensate (A) prepared in the step 1; and a step 3 of causing the reaction between the polycondensate (A) isolated in the step 2 and the (meth)acrylic acid halide (B) in the presence of a base.

5. A radically curable compound obtained by the production method according to claim 1 .

6. A radically curable compound obtained by the production method according to claim 2 .

7. A radically curable compound obtained by the production method according to claim 3 .

8. A radically curable compound obtained by the production method according to claim 4 .

9. A radically curable composition comprising the radically curable compound according to claim 5 .

10. A radically curable composition comprising the radically curable compound according to claim 6 .

11. A radically curable composition comprising the radically curable compound according to claim 7 .

12. A radically curable composition comprising the radically curable compound according to claim 8 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Imada Tomoyuki
• Kage Takakazu
• SHIN Dongmi

Classifications

• C08G8/30

  by unsaturated compounds, e.g. terpenes · CPC title

• C07C69/54 Primary

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C07C37/002

  by transformation of a functional group, e.g. oxo, carboxyl · CPC title

• C08F22/14

  Esters having no free carboxylic acid groups · CPC title