IP Library Granted Patent US 9,150,491
Granted Patent B2
US 9,150,491 · App. 13/522,292 · Granted Oct 6, 2015

Bicyclohexane derivative compound and manufacturing method of the same

Inventors: Masatoshi Echigo (Hiratsuka, JP); Dai Oguro (Hiratsuka, JP)
Assignee: Mitsubishi Gas Chemical Company, Inc
C07C69/54C07C43/12C07C43/23C07C59/72C07C69/712C08F20/28C08F220/28C08K5/04G03F7/0392G03F7/0397C07C2101/14
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Quick Facts
Patent No.
US 9,150,491
App. No.
13/522,292
Granted
Oct 6, 2015
Kind
B2
Abstract

A bicyclohexane derivative compound useful in the field of photoresist, the field of intermediate of drugs and pesticides, and the like, and a manufacturing method of the same are provided. A bicyclohexane derivative compound represented by the following general formula (II) is provided. (In formula (II), Y independently represents an alkyl group of 1 to 10 carbons, a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, X 1 represents a halogen atom, m represents an integer of 0 to 11, and m represents an integer of 0 to 10.).

Claims (21)

1. A bicyclohexane derivative compound of formula (II)

wherein Y independently represents a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, X 1 represents a halogen atom, m represents an integer of 0 to 11, and m′ represents an integer of 0 to 10.

2. A bicyclohexane derivative compound of formula (VI)

wherein Y independently represents a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, m represents an integer of 0 to 11, and m′ represents an integer of 0 to 10, and R 1 to R 4 each independently represents a hydrogen atom or an alkyl group of 1 to 3 carbons.

3. A bicyclohexane derivative compound according to claim 2 , wherein general formula (VI) is the following general formula (VIII) or (IX)

4. A bicyclohexane derivative compound of formula (III)

wherein R 5 is an acid dissociative functional group represented by the following general formula (V), X 2 is a hydrogen atom or a halogen atom, L 1 is a divalent organic group selected from a single bond, or a linear or branched alkylene group of 1 to 4 carbons, and r 1 is 0 or 1

, wherein Y independently represents an alkyl group of 1 to 10 carbons, a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, m represents an integer of 0 to 11, and m′ represents an integer of 0 to 10.

5. A bicyclohexane derivative compound of formula (III-2)

wherein R 1A is an acid dissociative functional group represented by the following general formula (V) or a hydrogen atom, at least one of R 1A is an acid dissociative functional group represented by the following general formula (V), R 4A is a functional group selected from the group consisting of an alkyl group of 1 to 20 carbons, a cycloalkyl group of 3 to 20 carbons, an aryl group of 6 to 20 carbons, an alkoxy group of 1 to 20 carbons, a cyano group, a nitro group, a heterocyclic group, a hydroxyl group, a halogen atom, a carboxyl group and an alkylsilyl group of 1 to 20 carbons, or an acid dissociative functional group selected from the group consisting of a substituted methoxy group of 2 to 20 carbons, a 1-substituted ethoxy group of 3 to 20 carbons, a 1-substituted-n-propoxy group of 4 to 20 carbons, a 1-branched alkyloxy group of 3 to 20 carbons, a silyloxy group of 1 to 20 carbons, an acyloxy group of 2 to 20 carbons, a 1-substituted alkoxyalkyloxy group of 2 to 20 carbons, a cyclic etheroxy group of 2 to 20 carbons, an alkoxycarbonyloxy group of 2 to 20 carbons, an alkoxycarbonylalkyloxy group and a group represented by the following general formula (V-2), X is a hydrogen atom or a halogen atom, m 1 is an integer of 1 to 4, p is an integer of 0 to 5, m2 is an integer of 0 to 3, and m 1 +m 2 =4,

wherein Y independently represents an alkyl group of 1 to 10 carbons, a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, m represents an integer of 0 to 11, and m′ represents an integer of 0 to 10, and

wherein Y of general formula (V) independently represents an alkyl group of 1 to 10 carbons, a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, m of general formula (V) represents an integer of 0 to 11, and m′ of general formula (V) represents an integer of 0 to 10.

6. A bicyclohexane derivative compound of formula (IV)

, wherein R 1A is an acid dissociative functional group represented by the following general formula (V) or a hydrogen atom, at least one of R 1A is an acid dissociative functional group represented by the following general formula (V), R 6 represents a substituent group selected from the group consisting of a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an acyl group, an alkoxycarbonyl group, an alkyloyloxy group, an aryloyloxy group, a cyano group, and a nitro group;

R 7 represents a trivalent substituent group of 6 to 12 carbons having a benzene structure;

k0, j0, m0, n0, x0 and y0 are integers of 0 to 3;

k1, j1, m1, n1, x1 and y1 are integers of 0 to 3;

k2, j2, m2, n2, x2 and y2 are integers of 0 to 4; and

conditions of 1≦k0+k1+k2≦5, 1≦j0+j1+j2≦5, 1≦m0+m1+m2≦5, 1≦n0+n1+n2≦5, 1≦x0+x1+x2≦5, 1≦y0+y1+y2≦5, 1≦k1+j1+m1+n1+x1+y1≦18, 1≦k0+k1≦3, 1≦j0+j1≦3, 1≦m0+m1≦3, 1≦n0+n1≦3, 1≦x0+x1≦3 and 1≦y0+y1≦3 are met, and wherein

a plurality of R 1A and R 6 may each be the same or different and

wherein Y independently represents an alkyl group of 1 to 10 carbons, a halogen atom, an acyloxy group, an alkoxycarbonyl group or a hydroxyl group, m represents an integer of 0 to 11, and m′ represents an integer of 0 to 10.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2012
From: ECHIGO, MASATOSHI; OGURO, DAI
To: MITSUBISHI GAS CHEMICAL COMPANY, INC.
Reel/Frame 028548/0604 →
Priority Claims (1)
JP 2010-006202 · Jan 14, 2010 · national
Continuity (1)
Related Publication 20130030211A1 · Jan 31, 2013