# US 10,870,726 B2 · Polymer

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- Number: US 10,870,726 B2
- Document ID: US10870726B2
- Status: Granted
- Kind: B2
- Application number: 16/063,635
- Filed: 2016-12-15
- Published: 2018-12-27
- Granted: 2020-12-22
- Earliest claimed: 2015-12-18
- Assignees: Cambridge Display Technology Limited; Sumitomo Chemical Company, Limited
- Applicants: Cambridge Display Technology Limited; Sumitomo Chemical Company Limited
- Inventors: Kiran Kamtekar; Florence Bourcet; Martina Pintani
- Web page: https://patentgrep.com/patent/US10870726B2

## CPC

- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C09D 165/00: Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers
- C09K 11/06: containing organic luminescent materials
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- C08G 2261/122: statistical
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/148: Side-chains having aromatic units
- C08G 2261/149: Side-chains having heteroaromatic units
- C08G 2261/314: Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3245: containing nitrogen and oxygen as heteroatoms
- C08G 2261/344: containing heteroatoms
- C08G 2261/411: Suzuki reactions
- C08G 2261/512: Hole transport
- C08G 2261/5222: electrofluorescent
- C08G 2261/95: Use in organic luminescent diodes
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A polymer comprising a repeat unit of formula (I): (I) wherein each Ar1 and each Ar2 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; each Cy independently represents a saturated heterocyclic or carbocyclic ring that may be unsubstituted or substituted with one or more substituents; n is 1, 2 or 3; and adjacent groups Ar2 may be linked by a divalent linking group in the case where n is 2 or 3. The polymer may be used as a charge-transporting material or light-emitting material in an organic light-emitting device.

## Claims

### Claim 1

A polymer comprising a repeat unit of formula (I):
wherein each Ar1 and each Ar2 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; each Cy independently represents a saturated heterocyclic or carbocyclic ring that may be unsubstituted or substituted with one or more substituents; n is 1, 2 or 3; and adjacent groups Ar2 may be linked by a divalent linking group in the case where n is 2 or 3.

### Claim 2 (depends on 1)

A polymer according to claim 1 wherein the divalent linking group is selected from C1-10 alkylene; and a saturated monocyclic or polycyclic carbocyclic ring that may be unsubstituted or substituted with one or more substituents.

### Claim 3 (depends on 1)

A polymer according to claim 1 wherein n is 2.

### Claim 4 (depends on 2)

A polymer according to claim 2 wherein —(Ar2)n— is a group of formula (II) that may be unsubstituted or substituted with one or more substituents:
wherein — represents a bond to N of formula (I).

### Claim 5 (depends on 1)

A polymer according to claim 1 wherein each Ar2 is independently phenyl that may be unsubstituted or substituted with one or more substituents.

### Claim 6 (depends on 1)

A polymer according to claim 1 wherein Cy is a saturated carbocyclic ring.

### Claim 7 (depends on 6)

A polymer according to claim 6 wherein Cy is cyclohexane.

### Claim 8 (depends on 1)

A polymer according to claim 1 wherein Ar1 is unsubstituted or substituted phenyl.

### Claim 9 (depends on 1)

A polymer according to claim 1 wherein the polymer has a photoluminescence spectrum with a peak of less than or equal to 480 nm.

### Claim 10 (depends on 1)

A polymer according to claim 1 comprising one or more co-repeat units.

### Claim 11 (depends on 10)

A polymer according to claim 10 wherein the repeat units of formula (I) form 0.5-25 mol % of repeat units of the polymer.

### Claim 12 (depends on 10)

A polymer according to claim 10 wherein the co-repeat units comprise one or more C6-20 arylene co-repeat units that may each independently be unsubstituted or substituted with one or more substituents.

### Claim 13

A monomer of formula (III):
wherein each Ar1 and each Ar2 independently represents a substituted or unsubstituted aromatic or heteroaromatic group; each Cy independently represents a saturated heterocyclic or carbocyclic ring that may be unsubstituted or substituted with one or more substituents; n is 1, 2 or 3; and adjacent groups Ar2 may be linked by a divalent linking group in the case where n is 2 or 3, and each L represents a reactive leaving group.

### Claim 14 (depends on 13)

A monomer according to claim 13 wherein each L is independently selected from the group consisting of halogen; boronic acids and esters thereof; and sulfonic acid esters.

### Claim 15 (depends on 13)

A method of forming a polymer comprising the step of polymerising a monomer according to claim 13.

### Claim 16 (depends on 1)

An organic electronic device comprising a semiconductor layer wherein the semiconductor layer comprises a polymer according to claim 1.

### Claim 17 (depends on 16)

An organic electronic device according to claim 16 wherein the device is an organic light-emitting device comprising the semiconductor layer between an anode and a cathode.

### Claim 18 (depends on 17)

An organic electronic device according to claim 17 wherein the semiconductor layer is a light-emitting layer.

### Claim 19 (depends on 1)

A formulation comprising a polymer according to claim 1 and at least one solvent.

### Claim 20 (depends on 16)

A method of forming an organic electronic device according to claim 16, the method comprising the step of forming the semiconducting layer by depositing a formulation comprising the polymer and at least one solvent, and evaporating the at least one solvent.