# US 11,898,011 B2 · Polymers for use in electronic devices

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- Number: US 11,898,011 B2
- Document ID: US11898011B2
- Status: Granted
- Kind: B2
- Application number: 17/169,926
- Filed: 2021-02-08
- Published: 2021-08-26
- Granted: 2024-02-13
- Earliest claimed: 2020-02-19
- Assignees: Dupont Electronics, Inc.
- Applicants: Dupont Electronics, Inc.
- Inventors: Viacheslav V Diev; Nora Sabina Radu
- Web page: https://patentgrep.com/patent/US11898011B2

## CPC

- C08G 73/1085: {Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties}
- C07D 221/14: Aza-phenalenes, e.g. 1,8-naphthalimide
- C07D 311/80: Dibenzopyrans; Hydrogenated dibenzopyrans
- C08G 69/00: Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule (products obtained from isocyanates or isothiocyanates C08G18/00; polyamide-imides C08G73/14)
- C08G 73/1039: {comprising halogen-containing substituents}
- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- C08L 2203/16: used for films
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Disclosed is a dianhydride having Formula I, and diamines having Formula IV and Formula VII In the formulas: Y is alkyl, silyl, ester, siloxane, oligosiloxane, polysiloxane, O, S, SO2, BR3, NR3, P(O)R3, unsubstituted or substituted carbocyclic aryl, or unsubstituted or substituted heteroaryl and deuterated analogs thereof; Ar2— Ar4 are the same or different and are carbocyclic aryl, heteroaryl, or substituted derivatives thereof; Q1 is a single bond, alkyl, silyl, ester, siloxane, oligosiloxane, polysiloxane, O, S, SO2, BR3, NR3, P(O)R3, unsubstituted or substituted carbocyclic aryl, or unsubstituted or substituted heteroaryl and deuterated analogs thereof; R1-R2 are the same or different at each occurrence and are F, CN, deuterium, alkyl, fluoroalkyl, unsubstituted or substituted carbocyclic aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, siloxy and deuterated analogs thereof; R3 is alkyl or unsubstituted or substituted carbocyclic aryl; a and b are the same or different and are an integer from 0-5; and c is 0 or 1.

## Claims

### Claim 1

A dianhydride having Formula I
wherein:
Y is selected from the group consisting of alkyl, silyl, ester, siloxane, oligosiloxane, polysiloxane, SO2, BR3, NR3, P(O)R3, unsubstituted or substituted carbocyclic aryl, and unsubstituted or substituted heteroaryl and deuterated analogs thereof;
R1-R2 are the same or different at each occurrence and are selected from the group consisting of F, CN, deuterium, alkyl, fluoroalkyl, unsubstituted or substituted carbocyclic aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, and siloxy and deuterated analogs thereof;
R3 is selected from the group consisting of alkyl and unsubstituted or substituted carbocyclic aryl and deuterated analogs thereof; and
a and b are the same or different and are an integer from 0-5.

### Claim 2

A diamine having Formula IV or Formula VII
wherein:
Ar2, Ar3, and Ar4 are the same or different and are selected from the group consisting of carbocyclic aryl, heteroaryl, and substituted derivatives thereof and deuterated analogs thereof;
Q1 is selected from the group consisting of a single bond, alkyl, silyl, ester, siloxane, oligosiloxane, polysiloxane, O, S, SO2, BR3, NR3, P(O)R3, unsubstituted or substituted carbocyclic aryl, and unsubstituted or substituted heteroaryl and deuterated analogs thereof;
R1 and R2 are the same or different at each occurrence and are selected from the group consisting of F, CN, deuterium, alkyl, fluoroalkyl, unsubstituted or substituted carbocyclic aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, siloxy and deuterated analogs thereof;
R3 is selected from the group consisting of alkyl and unsubstituted or substituted carbocyclic aryl and deuterated analogs thereof; and
a and b are the same or different and are an integer from 0-5; and
c is 0 or 1.

### Claim 3 (depends on 1)

A polyamic acid having a repeat unit structure of Formula II
where:
Ra is the same or different at each occurrence and represents one or more tetracarboxylic acid component residues; and
Rb is the same or different at each occurrence and represents one or more aromatic diamine residues;
wherein 0.001-100 mol % of Ra is a residue from one or more dianhydrides having Formula I according to claim 1.

### Claim 4 (depends on 2)

A polyamic acid having a repeat unit structure of Formula V or Formula VIII
where:
Ra1 is the same or different at each occurrence and represents one or more tetracarboxylic acid component residues; and
Ra2 is the same or different at each occurrence and represents one or more tetracarboxylic acid component residues;
Rb1 is the same or different at each occurrence and represents one or more aromatic diamine residues; and
Rb2 is the same or different at each occurrence and represents one or more aromatic diamine residues;
wherein 0.001-100 mol % of Rb1 is a diamine residue from one or more diamines having Formula IV according to claim 2; and
wherein 0.001-100 mol % of Rb2 is a diamine residue from one or more diamines having Formula VII according to claim 2.

### Claim 5 (depends on 1)

A polyimide having a repeat unit structure of Formula III
where
Ra is the same or different at each occurrence and represents one or more tetracarboxylic acid component residues; and
Rb is the same or different at each occurrence and represents one or more aromatic diamine residues;
wherein 0.001-100 mol % of Ra is a residue from one or more dianhydrides having Formula I according to claim 1.

### Claim 6 (depends on 2)

A polyimide having a repeat unit structure of Formula VI or Formula IX
where:
Ra1 is the same or different at each occurrence and represents one or more tetracarboxylic acid component residues; and
Ra2 is the same or different at each occurrence and represents one or more tetracarboxylic acid component residues;
Rb1 is the same or different at each occurrence and represents one or more aromatic diamine residues; and
Rb2 is the same or different at each occurrence and represents one or more aromatic diamine residues;
wherein 0.001-100 mol % of Rb1 is a diamine residue from one or more diamines having Formula IV according to claim 2; and
wherein 0.001-100 mol % of Rb2 is a diamine residue from one or more diamines having Formula VII according to claim 2.

### Claim 7 (depends on 5)

A flexible replacement for glass in an electronic device wherein the flexible replacement for glass comprises a polyimide film having a repeat unit of Formula III, according to claim 5.

### Claim 8 (depends on 7)

An electronic device comprising the flexible replacement for glass, according to claim 7.

### Claim 9 (depends on 6)

A flexible replacement for glass in an electronic device wherein the flexible replacement for glass comprises a polyimide film having a repeat unit of Formula IV or Formula IX, according to claim 6.

### Claim 10 (depends on 9)

An electronic device comprising the flexible replacement for glass, according to claim 9.