Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator

Patent metadata

Field	Value
Publication number	US-9684238-B2
Application number	US-201314431813-A
Country	US
Kind code	B2
Filing date	Sep 20, 2013
Priority date	Sep 28, 2012
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

According to an embodiment of the present invention, there is provided a novel fluorene-based compound and a photopolymerization initiator using the fluorene-based compound. The fluorene-based compound according to an embodiment of the present invention is represented by the general formula (1). A photopolymerization initiator having additionally high sensitivity can be provided by using the fluorene-based compound. In addition, a photopolymerization initiator that can impart additionally excellent characteristics can be provided by appropriately selecting, for example, a substituent.

First claim

The invention claimed is:

1. A fluorene-based compound, which is represented by the general formula (1):

in the general formula (1):
when m represents 0 and n represents 0, R 1 represents a hydrogen atom, a halogen atom, a nitro group, a sulfonyloxy group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, a phenylsulfonyloxy group that may be substituted, a sulfonyl group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, a phenylsulfonyl group that may be substituted, a heterocyclic sulfonyl group that may be substituted, or a condensed ring sulfonyl group that may be substituted, when m represents 0 and n represents 1, R 1 represents a phenyl group that may be substituted, a heterocyclic group that may be substituted, or a condensed ring group that may be substituted, and when m represents 1 and n represents 1, R 1 represents a sulfonyloxy group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, or a phenylsulfonyloxy group that may be substituted;
R 2 and R 3 each independently represent, a linear or branched halogenated alkyl group having 1 to 10 carbon atoms, or a linear or branched alkyl group having 2 to 9 carbon atoms interrupted by one or more ether bonds, and R 2 and R 3 may form a ring together;
R 4 represents a group represented by the formula (2):

 in the formula (2) R 5 represents a linear, branched, or cyclic alkyl group having 1 to 17 carbon atoms, a linear or branched halogenated alkyl group having 2 to 5 carbon atoms, a linear or branched alkyl group having 2 to 7 carbon atoms interrupted by one or more ether bonds or thioether bonds, a phenyl group that may be substituted, a phenylalkyl group having 7 to 11 carbon atoms that may be substituted, a phenoxyalkyl group having 7 to 10 carbon atoms that may be substituted, a heterocyclic group that may be substituted, or a condensed ring group that may be substituted,
in the formula (2), R 6 represents a branched, or cyclic alkyl group having 3 to 17 carbon atoms, a linear or branched halogenated alkyl group having 1 to 7 carbon atoms, a linear or branched alkyl group having 2 to 7 carbon atoms interrupted by one or more ether bonds or thioether bonds, a linear or branched aminoalkyl group having 2 to 3 carbon atoms that may be substituted, a phenyl group that may be substituted, a condensed ring group that may be substituted, or a heterocyclic group that may be substituted, and
m and n each represent 0 or 1, and when m represents 1, n represents 1.

2. The fluorene-based compound according to claim 1 , wherein the R 5 represents a methyl group.

3. The fluorene-based compound according to claim 1 , wherein the R 4 represents a group represented by the formula (2), and the R 6 represents a branched or cyclic alkyl group having 3 to 17 carbon atoms, a linear or branched halogenated alkyl group having 1 to 5 carbon atoms, a phenyl group that may be substituted, a condensed ring group that may be substituted, or a heterocyclic group that may be substituted.

4. The fluorene-based compound according to claim 1 , wherein:
the m and the n each represent 0, and the R 1 represents a halogen atom or a nitro group; or
the m represents 0 and the n represents 1, and the R 1 represents a phenyl group that may be substituted, a condensed ring group that may be substituted, or a heterocyclic group that may be substituted.

5. A photopolymerization initiator, comprising at least one kind of the fluorene-based compound of claim 1 .

6. A photosensitive composition, comprising:
a compound having at least one ethylenically unsaturated bond; and
the photopolymerization initiator of claim 5 .

7. A fluorene-based compound, which is represented by the general formula (1):

in the general formula (1):
when m represents 0 and n represents 0, R 1 represents a hydrogen atom, a halogen atom, a nitro group, a sulfonyloxy group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, a phenylsulfonyloxy group that may be substituted, a sulfonyl group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, a phenylsulfonyl group that may be substituted, a heterocyclic sulfonyl group that may be substituted, or a condensed ring sulfonyl group that may be substituted, when m represents 0 and n represents 1, R 1 represents a phenyl group that may be substituted, a heterocyclic group that may be substituted, or a condensed ring group that may be substituted, and when m represents 1 and n represents 1, R 1 represents a sulfonyloxy group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, or a phenylsulfonyloxy group that may be substituted;
R 2 and R 3 each independently represent a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 22 carbon atoms, a linear or branched halogenated alkyl group having 1 to 10 carbon atoms, or a linear or branched alkyl group having 2 to 15 carbon atoms interrupted by one or more ether bonds or thioether bonds, and R 2 and R 3 may form a ring together;

wherein the R 4 represents a group represented by the formula (3):

 in the formula (3), R 5′ represents a linear, branched, or cyclic alkyl group having 1 to 17 carbon atoms, a linear or branched halogenated alkyl group having 2 to 5 carbon atoms, a linear or branched alkyl group having 2 to 7 carbon atoms interrupted by one or more ether bonds or thioether bonds, a phenyl group that may be substituted, a phenylalkyl group having 7 to 11 carbon atoms that may be substituted, a phenoxyalkyl group having 7 to 10 carbon atoms that may be substituted, a heterocyclic group that may be substituted, or a condensed ring group that may be substituted, and the R 7 represents a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear or branched halogenated alkyl group having 1 to 4 carbon atoms, a phenyl group that may be substituted, a phenylalkyl group having 7 to 10 carbon atoms that may be substituted, a phenylalkyl group having 7 to 9 carbon atoms that is interrupted by one or more ether bods or thioether bonds and may be substituted, a condensed ring group that may be substituted, or a heterocyclic group that may be substituted.

8. A fluorene-based compound, which is represented by the general formula (1):

in the general formula (1):
when m represents 0 and n represents 0, R 1 represents a hydrogen atom, a halogen atom, a nitro group, a sulfonyloxy group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, a phenylsulfonyloxy group that may be substituted, a sulfonyl group substituted with an alkyl group having 1 to 8 carbon atoms that may be substituted with a halogen atom, a phenylsulfonyl group that may be substituted, a heterocyclic sulfonyl group that may be substituted, or a condensed ring sulfonyl group that may be substituted, when m represents 0 and n represents 1, R 1 represents a phenyl group that may be substituted, a heterocyclic group that

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Harihara Makoto
• Yamazaki Tomohiko
• Kuwamura Katsuji

Classifications

• G03F7/031

  Organic compounds not covered by group G03F7/029 · CPC title

• G03F7/028 Primary

  with photosensitivity-increasing substances, e.g. photoinitiators · CPC title

• C08F4/00

  Polymerisation catalysts · CPC title

• C07D333/34

  Sulfur atoms · CPC title

• C07D333/22

  Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom · CPC title