POLYOL COMPOUND FOR PHOTORESIST

• US 20110027725A1
• Filed: 04/02/2009
• Published: 02/03/2011
• Est. Priority Date: 04/04/2008
• Status: Abandoned Application

• Current Assignee: Daicel Chemical Industries Limited (Daicel Corporation)
• Original Assignee: Daicel Chemical Industries Limited (Daicel Corporation)
• Inventors: Funaki, Yoshinori, Okumura, Arimichi, Tsutsumi, Kiyoharu
• Application Number:
  US12/935,537
• Publication Number:
  US 20110027725A1
• Time in Patent Office: Days
• US Class Current: 430/325
• CPC Class Codes: C08G 2261/342 containing only carbon atoms
• CPC Class Codes: C08G 2261/45 Friedel-Crafts-type
• CPC Class Codes: C08G 61/02 Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• CPC Class Codes: C08L 65/00 Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C08L7/00 - C08L57/00, C08L61/00 take precedence; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 165/00 Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C09D107/00 - C09D157/00, C09D161/00 take precedence; Coating compositions based on derivatives of such polymers
• CPC Class Codes: G03F 7/0392 the macromolecular compound being present in a chemically amplified positive photoresist composition

Abstract

A polyol compound for photoresists has at least one aliphatic group and at least one aromatic group bound to each other alternately, in which the aromatic group has at least one aromatic ring and two or more hydroxyl groups bound to the aromatic ring. The polyol compound for photoresists can be prepared through an acid-catalyzed reaction, such as a Friedel-Crafts reaction, between an aliphatic polyol and an aromatic polyol. The aliphatic polyol is preferably an alicyclic polyol. The aromatic polyol is preferably hydroquinone.

By protecting phenolic hydroxyl group(s) thereof with a protecting group capable of leaving with an acid, the polyol compound for photoresists gives a compound for photoresists. A photoresist composition containing this compound can form a resist pattern which shows less line edge roughness (LER), excels in resolution and etching resistance, and is fine and sharp.

Claims

1. A polyol compound for photoresists, comprising at least one aliphatic group and at least one aromatic group bound to each other alternately, the aromatic group having at least one aromatic ring and two or more hydroxyl groups bound to the aromatic ring.

2. The polyol compound for photoresists according to claim 1, as a product of an acid-catalyzed reaction between an aliphatic polyol and an aromatic polyol.

3. The polyol compound for photoresists according to claim 2, wherein the acid-catalyzed reaction is a Friedel-Crafts reaction.

4. The polyol compound for photoresists according to claim 2 or 3, wherein the aliphatic polyol is an alicyclic polyol.

5. The polyol compound for photoresists according to claim 2, wherein the aliphatic polyol is an adamantanepolyol having an adamantane ring and two or more hydroxyl groups bound at the tertiary positions of the adamantane ring.

6. The polyol compound for photoresists according to claim 2, wherein the aromatic polyol is hydroquinone.

7. The polyol compound for photoresists according to claim 2, wherein the aromatic polyol is a naphthalenepolyol.

8. The polyol compound for photoresists according to claim 1, wherein the polyol compound has a weight-average molecular weight of 500 to 5000.

9. A compound for photoresists, comprising one ore more phenolic hydroxyl groups in the polyol compound for photoresists of claim 1, the phenolic hydroxyl groups being protected by protecting groups capable of leaving with an acid in part or all of the phenolic hydroxyl groups.

10. The compound for photoresists according to claim 9, wherein an acetal structure is formed as a result of the protection of the phenolic hydroxyl group of the polyol compound for photoresists by the protecting group capable of leaving with an acid.

11. The compound for photoresists according to claim 10, wherein the acetal structure is formed through a reaction between the phenolic hydroxyl group and a vinyl ether compound.

12. A photoresist composition comprising at least the compound for photoresists according to claim 9.

13. A process for the formation of a resist pattern, the process comprising the steps of forming a resist film from the photoresist composition according to claim 12;

pattern-wise exposing the resist film; and

developing the pattern-wise-exposed resist film.

14. A process for the production of a polyol compound for photoresists, the process comprising the step of carrying out an acid-catalyzed reaction between an aliphatic polyol and an aromatic polyol to give a polyol compound containing at least one aliphatic group and at least one aromatic group bound to each other alternately, the aromatic group having at least one aromatic ring and two or more hydroxyl groups bound to the aromatic ring.

15. The process for the production of a polyol compound for photoresists, according to claim 14, further comprising the step of mixing a solution of the polyol compound for photoresists with a poor solvent with respect to a compound having one or more phenolic hydroxyl groups to deposit or separate as a different layer hydrophobic impurities to thereby remove the hydrophobic impurities, the polyol compound having been formed through the acid-catalyzed reaction between the aliphatic polyol and the aromatic polyol and containing at least one aliphatic group and at least one aromatic group bound to each other alternately, the aromatic group having at least one aromatic ring and two or more hydroxyl groups bound to the aromatic ring.

16. The process for the production of a polyol compound for photoresists, according to claim 15, further comprising the step of mixing the solution, from which the hydrophobic impurities have been removed, with a poor solvent with respect to a compound having one or more phenolic hydroxyl groups to thereby deposit or separate as a different layer the polyol compound for photoresists, the polyol compound containing at least one aliphatic group and at least one aromatic group bound to each other alternately, the aromatic group having at least one aromatic ring and two or more hydroxyl groups bound to the aromatic ring.

17. The process for the production of a polyol compound for photoresists, according to claim 15 or 16, wherein the poor solvent for use in the deposition or layer-separation of the hydrophobic impurities is one selected from the group consisting of a solvent mixture containing water and a water-miscible organic solvent;

water; and

a hydrocarbon.