# US 8,569,752 B2 · Polar semiconductor hole transporting material

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- Number: US 8,569,752 B2
- Document ID: US8569752B2
- Status: Granted
- Kind: B2
- Application number: 13/460,784
- Filed: 2012-04-30
- Published: 2012-08-30
- Granted: 2013-10-29
- Earliest claimed: 2004-10-11
- Assignees: Cambridge Display Technology Limited; CDT Oxford Limited
- Applicants: Mary J. McKiernan; Annette Steudel; Caroline Towns
- Inventors: Carl R. Towns; Mary J. McKiernan; Annette Steudel
- Web page: https://patentgrep.com/patent/US8569752B2

## CPC

- C08G 73/026: {Wholly aromatic polyamines}
- C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G 73/02: Polyamines
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE}
- H10K 85/151: {Copolymers}
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- H10K 50/14: Carrier transporting layers
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A semiconductive hole transport material containing polar substituent groups, the polar substituent groups substantially not affecting the electronic properties of the hole transport material and the hole transport material being soluble in a polar solvent.

## Claims

### Claim 1

An organic electronic device comprising an emissive layer and a hole-transporting layer, said hole-transporting layer comprising a semiconductive hole transport polymer containing fluorene, spirofluorene, indenofluorene, phenylene, phenylenevinylene, thiophene, benzothiadiazole, carbazole, or triarylamine repeat units in a backbone of the polymer, at least some of which repeat units have polar substituent groups, wherein said polar substituent groups do not substantially affect the electronic properties of the hole transport polymer, and the hole transport polymer is soluble in a polar solvent.

### Claim 2 (depends on 1)

An organic electronic device according to claim 1, wherein the nature and number of polar substituent groups are selected such that the hole transport polymer is soluble in a polar solvent having a dielectric constant at 20° C. of greater than 15.

### Claim 3 (depends on 1)

An organic electronic device according to claim 1, wherein the polar substituent groups independently are selected from aliphatic or alicyclic oxygen-, nitrogen-, sulphur- and phosphorous-containing groups.

### Claim 4 (depends on 1)

An organic electronic device according to claim 1, wherein the polar substituent groups independently are selected from polyether, hydroxyl, ester, acid, amine, cyano, amide, imine, sulfonate, and sulfate.

### Claim 5 (depends on 1)

An organic electronic device according claim 1 wherein the polar substituent groups comprise a plurality of groups XY, where XY represents a group with a high dissociation constant such that it is ionized completely.

### Claim 6 (depends on 1)

An organic electronic device according to claim 1, wherein the hole transport polymer comprises a repeat unit comprising general formula 25:
where Ar represents an aryl or heteroaryl group selected from the group consisting of fluorene, spirofluorene, indenofluorene, phenylene, phenylenevinylene, thiophene, benzothiadiazole, carbazole, and triarylamine; x represents an optional organic spacer group; and R represents a polar substituent group.

### Claim 7 (depends on 6)

An organic electronic device according to claim 6, wherein x comprises a group which breaks any conjugation between R and Ar.

### Claim 8 (depends on 6)

An organic electronic device according claim 6, wherein Ar represents fluorene.

### Claim 9 (depends on 8)

An organic electronic device according to claim 8, wherein the hole transport polymer comprises a repeat unit general formula I:
where x and x′ are optional organic spacer groups; R and R′ are polar substituent groups; and n4 and n5 each independently is in the range of from 0 to 5.

### Claim 10 (depends on 6)

An organic electronic device according claim 6, wherein the polymer contains a further aryl or heteroaryl repeat unit.

### Claim 11 (depends on 10)

An organic electronic device according to claim 10, wherein the further repeat unit is a triarylamine repeat unit or a fluorene repeat unit.

### Claim 12 (depends on 1)

An organic electronic device according to claim 1 which is substantially insoluble in a non-polar solvent.