Phenolic hydroxyl-containing compound, composition containing the same, and cured film of the composition

Patent metadata

Field	Value
Publication number	US-10266471-B2
Application number	US-201515532272-A
Country	US
Kind code	B2
Filing date	Nov 19, 2015
Priority date	Jan 16, 2015
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

A phenolic hydroxyl-containing compound is provided. The compound dissolves well in solvents and can be formulated into compositions that give coatings superior in thermal decomposition resistance, alkali developability, resolution, and dry-etch resistance. Specifically, the compound is a phenolic hydroxyl-containing calixarene represented by structural formula (1):

(where A is a structural unit including a dihydroxynaphthalene- or naphthol-derived structure optionally with a substituent alkyl, alkoxy, aryl, or aralkyl group or halogen atom on the aromatic rings and a methylene group optionally having an alkyl or aryl group in place of one of the hydrogen atoms) and obtained using a dihydroxynaphthalene in combination with a naphthol, with the total repeat number p being an integer of 2 to 10.

First claim

The invention claimed is:

1. A method of producing a calix[2-10]arene compound, which comprises a step of reacting a substituted or unsubstituted 1,6-dihydroxynaphthalene compound and a substituted or unsubstituted 1-naphthol with an aliphatic aldehyde having two or more carbon atoms or an aromatic aldehyde in the presence of an inorganic acid catalyst,
wherein up to four of the hydrogens bonded directly to the naphthalene ring of 1,6-dihydroxynaphthalene and up to five of the hydrogens bonded directly to the naphthalene ring of naphthol are replaced with substituents selected from a group consisting of an alkyl group, an alkoxy group, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a halogen atom, and plural substituents may be the same as or different from each other;
the calix arene compound includes a structure comprising units of substituted or unsubstituted 1,6-dihydroxynaphthalene structure and substituted or unsubstituted 1-naphthol structure.

2. The method of producing a calix[2-10]arene compound according to claim 1 , wherein a total number of repeats the units of substituted or unsubstituted 1,6-dihydroxynaphthalene structure and substituted or unsubstituted 1-naphthol structure in the calix[2-10]arene compound is an integer of 2 to 10.

3. The method of producing a calix[2-10]arene compound according to claim 2 , wherein the reaction of a substituted or unsubstituted 1,6-dihydroxynaphthalene compound and a substituted or unsubstituted 1-naphthol with an aliphatic aldehyde having two or more carbon atoms or an aromatic aldehyde in the presence of an inorganic acid catalyst is carried out in an organic solvent, and the organic solvent is a butanol.

4. The method of producing a calix[2-10]arene compound according to claim 1 , wherein the inorganic acid catalyst is selected from one of the groups consisting of hydrochloric acid, sulfonic acid, phosphoric acid.

5. The method of producing a calix[2-10]arene compound according to claim 4 , wherein the reaction of a substituted or unsubstituted 1,6-dihydroxynaphthalene compound and a substituted or unsubstituted 1-naphthol with an aliphatic aldehyde having two or more carbon atoms or an aromatic aldehyde in the presence of an inorganic acid catalyst is carried out in an organic solvent, and the organic solvent is a butanol.

6. The method of producing a calix[2-10]arene compound according to claim 1 , wherein the inorganic acid catalyst is sulfonic acid.

7. The method of producing a calix[2-10]arene compound according to claim 6 , wherein the reaction of a substituted or unsubstituted 1,6-dihydroxynaphthalene compound and a substituted or unsubstituted 1-naphthol with an aliphatic aldehyde having two or more carbon atoms or an aromatic aldehyde in the presence of an inorganic acid catalyst is carried out in an organic solvent, and the organic solvent is a butanol.

8. The method of producing a calix[2-10]arene compound according to claim 1 , wherein the inorganic acid catalyst is strong sulfonic acid.

9. The method of producing a calix[2-10]arene compound according to claim 8 , wherein the reaction of a substituted or unsubstituted 1,6-dihydroxynaphthalene compound and a substituted or unsubstituted 1-naphthol with an aliphatic aldehyde having two or more carbon atoms or an aromatic aldehyde in the presence of an inorganic acid catalyst is carried out in an organic solvent, and the organic solvent is a butanol.

10. The method of producing a calix[2-10]arene compound according to claim 1 , wherein the reaction of a substituted or unsubstituted 1,6-dihydroxynaphthalene compound and a substituted or unsubstituted 1-naphthol with an aliphatic aldehyde having two or more carbon atoms or an aromatic aldehyde in the presence of an inorganic acid catalyst is carried out in an organic solvent, and the organic solvent is butanol.

Assignees

• Dainippon Ink & Chemicals

Inventors

• Imada Tomoyuki
• Nagae Norio

Classifications

• G03F7/091

  characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement · CPC title

• G03F7/0226

  characterised by the non-macromolecular additives · CPC title

• C08G65/38

  derived from phenols · CPC title

• C07C39/14 Primary

  with at least one hydroxy group on a condensed ring system containing two rings · CPC title

• G03F7/094

  Multilayer resist systems, e.g. planarising layers · CPC title