Production method of polymer compound

Patent metadata

Field	Value
Publication number	US-2022017687-A1
Application number	US-201917296221-A
Country	US
Kind code	A1
Filing date	Sep 4, 2019
Priority date	Dec 6, 2018
Publication date	Jan 20, 2022
Grant date	—

Abstract

A method of producing a polymer compound which is capable of improving yield while lowering the dispersity of the molecular weight is described. The method of producing polymer compound A containing a constitutional unit (1-2) having a group obtained by removing one or more hydrogen atoms present on Ar1 from a compound represented by the formula [1-2] involves a first step of separating high molecular weight components contained in a polymer compound B by a fractionation precipitation method from the polymer compound B containing a constitutional unit (1-1) having a group obtained by removing one or more hydrogen atoms present on Ar1 from a compound represented by the formula [1-1], to obtain a polymer compound C composed of the high molecular weight components, and a second step of converting the constitutional unit (1-1) contained in polymer compound C into constitutional unit (1-2), to obtain polymer compound A:

First claim

1 . A method of producing a polymer compound A containing a constitutional unit (1-2) having a group obtained by removing one or more hydrogen atoms present on Ar 1 from a compound represented by the formula [1-2], comprising
a first step of separating high molecular weight components contained in a polymer compound B, by a fractionation precipitation method, from the polymer compound B containing a constitutional unit (1-1) having a group obtained by removing one or more hydrogen atoms present on Ar 1 from a compound represented by the formula [1-1], to obtain a polymer compound C composed of the high molecular weight components, and a second step of converting said constitutional unit (1-1) contained in said polymer compound C obtained by said first step into said constitutional unit (1-2), to obtain said polymer compound A:

wherein,
Ar 1 represents an aryl group optionally having a substituent or a monovalent heterocyclic group optionally having a substituent,
R A and R B each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.

2 . The production method according to claim 1 , wherein said polymer compound B, a good solvent for said polymer compound B and a poor solvent for said polymer compound B are used in said fractionation precipitation method.

3 . The production method according to claim 1 , wherein said polymer compound A, said polymer compound B and said polymer compound C further contain a constitutional unit represented by the formula (X):

wherein,
a 1 and a 2 each independently represent an integer of 0 or more,
Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent,
Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly, and these groups optionally have a substituent, when a plurality of Ar X2 and Ar X4 are present, they may be the same or different at each occurrence,
R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent, when a plurality of R X2 and R X3 are present, they may be the same or different at each occurrence.

4 . The production method according to claim 1 , wherein said constitutional unit (1-1) is a constitutional unit represented by the formula (2-1), and said constitutional unit (1-2) is a constitutional unit represented by the formula (2-2):

wherein,
n1 and nA1 each independently represent an integer of 1 to 3, when a plurality of nA1 are present, they may be the same or different,
m1 represents an integer of 1 or more, when a plurality of m1 are present, they may be the same or different,
X represents a formyl group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, when X is an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, these groups optionally have a substituent, when a plurality of X are present, they may be the same or different, however, at least one X is a formyl group,
Ar A and Ar B each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent, Ar C represents an aromatic hydrocarbon ring or a heterocyclic group, and these groups optionally have a substituent, when a plurality of Ar B and Ar C are present, they may be the same or different at each occurrence, at least two or more of Ar A , Ar B and Ar C may be combined together to form a ring,
R 1 represents a single bond or an aliphatic hydrocarbon group, and these groups optionally have a substituent, when a plurality of R 1 are present, they may be the same or different, however, nA1 is 1 when R 1 is a single bond,
R C and R D each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent, when a plurality of R C and R D are present, they may be the same or different at each occurrence.

5 . The production method according to claim 1 , wherein said constitutional unit (1-1) is a constitutional unit represented by the formula (3-1), and said constitutional unit (1-2) is a constitutional unit represented by the formula (3-2):

wherein,
n2 and nA2 each independently represent an integer of 1 to 3, when a plurality of nA2 are present, they may be the same or different,
m2 represents an integer of 1 or more, when a plurality of m2 are present, they may be the same or different,
Y represents a formyl group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, when Y is an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, these groups optionally have a substituent, when a plurality of Y are present, they may be the same or different, however, at least one Y is a formyl group,
Ar D represents an aromatic hydrocarbon ring or a heterocyclic group, and these groups optionally have a substituent,
Ar E represents an aromatic hydrocarbon ring or a heterocyclic group, and these groups optionally have a substituent, when a plurality of Ar E are present, they may be the same or different,
R 2 represents a single bond or an aliphatic hydrocarbon group, and these groups optionally have a substituent, when a plurality of R 2 are present, they may be the same or different,
R E and R F each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent, when a plurality of R E and R F are present, they may be the same or different at each occurrence.

6 . The production method according to claim 1 , wherein said constitutional unit (1-1) is a constitutional unit represented by the formula (4-1), and said constitutional unit (1-2) is a constitutional unit represented by the formula (4-2):

wherein,
n3 represents an integer of 1 to 3,
Z represents a formyl group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, when Z is an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, these groups optionally have a substituent, when a plurality of Z are present, they may be the same or different, however, at least one Z is a formyl group,
Ar F represents an aromatic hydrocarbon ring or a heterocyclic group, and these groups optionally have a substituent,
R G and R H each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent, when a plurality of R G and R H are present, they may be the same or different at each occurrence.

7 . The production method according to claim 1 , comprising a step of purifying the resultant polymer compound A using an ads

Assignees

• Sumitomo Chemical Co

Inventors

• Sakakibara Ken
• Shiratori Mio

Classifications

• C08G2261/148

  Side-chains having aromatic units · CPC title

• C08G2261/1426

  containing carboxy groups (COOH) and/or -C(=O)O-moieties · CPC title

• C08G2261/411

  Suzuki reactions · CPC title

• C08G2261/71

  Purification · CPC title

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title