Compound, photopolymerization initiator comprising said compound, and photosensitive resin composition containing said photopolymerization initiator

Patent metadata

Field	Value
Publication number	US-10508078-B2
Application number	US-201615781623-A
Country	US
Kind code	B2
Filing date	Dec 7, 2016
Priority date	Dec 9, 2015
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

The purpose of the present invention is to provide: a novel compound which can generate a base and radical upon the irradiation with an active energy ray; a photopolymerization initiator which comprises the novel compound; and a photosensitive resin composition which contains the photopolymerization initiator, has high sensitivity and excellent storage stability, and can be formed into a cured article that does not have a metal-corrosive property. The novel compound is represented by formula (1):

(wherein R 1 to R 6 independently represent a hydrogen atom, a hydroxy group, an alkoxy group, an organic group other than the aforementioned substituents, or the like; X represents a residue having a structure such that n hydrogen atoms are removed from a saturated hydrocarbon containing a ring structure; and n represents an integer of 1 to 6).

First claim

The invention claimed is:

1. A compound of formula (1):

wherein in formula (1),
R 1 is a hydrogen atom, a hydroxyl group, an alkoxy group having a carbon number of 1 to 18 or an organic group selected from the group consisting of an alkyl group having a carbon number of 1 to 18, an alkenyl group having a carbon number of 2 to 18, an alkynyl group having a carbon number of 2 to 18, an aryl group having a carbon number of 6 to 12, an acyl group having a carbon number 1 to 18, an aroyl group having a carbon number of 7 to 18, a nitro group, a cyano group, an alkylthio group having a carbon number of 1 to 18, and a halogen atom,
when there is a plurality of R 1 , each R 1 may be the same or different from each other;
R 2 , R 3 , R 5 , and R 6 each independently is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group having a carbon number of 1 to 18, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a cyano group, a sulfino group, a sulfo group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphono group, a phosphonato group, an amino group, an ammonio group, or an organic group selected from the group consisting of an alkyl group having a carbon number of 1 to 20, an aryl group having a carbon number of 6 to 20, an aralkyl group, a halogenated alkyl group, an isocyano group, a cyanate group, an isocyanato group, a thiocyanato group, an isothiocyanato group, an alkoxycarbonyl group, a carbamoyl group, a thiocarbamoyl group, a carboxyl group, a carboxylate group, an acyl group having a carbon number of 1 to 20, an acyloxy group, and a hydroxyimino group;
R 2 and R 3 on the same benzene ring may be connected to form a ring structure;
R 5 and R 6 on the same benzene ring may be connected to form a ring structure;
R 4 each independently is an organic group selected from the group consisting of an alkyl group having a carbon number of 1 to 20 containing a thioether bond, an aryl group having a carbon number of 6 to 20 containing a thioether bond, an aralkyl group containing a thioether bond, a halogenated alkyl group containing a thioether bond, an isocyano group containing a thioether bond, a cyanate group containing a thioether bond, an isocyanato group containing a thioether bond, a thiocyanato group containing a thioether bond, an isothiocyanato group containing a thioether bond, an alkoxycarbonyl group containing a thioether bond, a carbamoyl group containing a thioether bond, a thiocarbamoyl group containing a thioether bond, a carboxyl group containing a thioether bond, a carboxylate group containing a thioether bond, an acyl group containing a thioether bond, an acyloxy group having an acyl group containing a thioether bond, and a hydroxyimino group containing a thioether bond;
X is a residue being a saturated hydrocarbon including a ring structure having a 3- to 10-membered ring from which n hydrogen atoms are removed; and
n is an integer of 1 to 6.

2. The compound according to claim 1 , wherein the organic group of R 4 is an alkyl group having a carbon number of 1 to 20 containing a thioether bond or an aryl group having a carbon number of 6 to 20 containing a thioether bond.

3. The compound according to claim 1 , wherein the compound has the structure of formula (2):

wherein in formula (2),
R 1 to R 6 are the same as R 1 to R 6 in formula (1);
A is a cycloalkylene group which is a saturated cyclic hydrocarbon from which two hydrogen atoms are removed, and which is selected from the group consisting of a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloadamantane ring; and
D is an alkylene group having a carbon number of 1 to 18.

4. The compound according to claim 3 , wherein the compound has the structure of formula (3):

wherein in formula (3), R 1 to R 6 are the same as R 1 to R 6 in formula (2).

5. The compound according to claim 1 , wherein R 1 is a hydroxyl group.

6. A photopolymerization initiator comprising the compound according to claim 1 .

7. A photosensitive resin composition comprising a polymer precursor capable of being polymerized by irradiation or by both of irradiation and heating in the presence of a photopolymerization initiator, and the photopolymerization initiator according to claim 6 .

8. The photosensitive resin composition according to claim 7 , wherein the polymer precursor comprises at least one selected from the group consisting of a compound having a substituent selected from the group consisting of an epoxy group, an isocyanate group, an oxetane group, an acryloyl group, a methacryloyl group, a maleimide group, and a thiirane group; a polysiloxane precursor; a polyimide precursor; and a polybenzoxazole precursor.

9. The photosensitive resin composition according to claim 8 , wherein the polymer precursor comprises a compound having an epoxy group.

10. A method for forming a pattern comprising:
changing solubility of an irradiation area by irradiation to a coat, a film or a formed body of the photosensitive resin composition according to claim 7 in a predefined pattern, followed by heating or on heating; and
removing a non-irradiated area by performing development.

Assignees

• Univ Tokyo Science Found
• Nippon Kayaku Kk

Inventors

• TERADA Kiwamu
• Yamamoto Kazuyoshi
• Arimitsu Koji

Classifications

• G03F7/0385

  using epoxidised novolak resin · CPC title

• G03F7/0387

  Polyamides or polyimides · CPC title

• C08F2/50

  with sensitising agents · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title