IP Library Granted Patent US 9,559,307
Granted Patent B2
US 9,559,307 · App. 14/137,275 · Granted Jan 31, 2017

Polymer and organic electronic device

Inventors: Annette Steudel (Cambridgeshire, GB); Florence Bourcet (Cambridgeshire, GB); Kiran Kamtekar (Cambridgeshire, GB)
Assignees: Cambridge Display Technology, Ltd.; Sumitomo Chemical Company Limited
H01L51/0043C08G61/12C08G61/122C08G73/0644C08K5/0091C09D179/04C09K11/06H01L51/0039H01L51/0085H05B33/10C08G2261/135C08G2261/148C08G2261/1412C08G2261/1624C08G2261/3142C08G2261/3162C08G2261/411C08G2261/95C08L65/00C09K2211/1466H01L51/009H01L51/5016
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Quick Facts
Patent No.
US 9,559,307
App. No.
14/137,275
Granted
Jan 31, 2017
Kind
B2
Abstract

A composition comprising a polymer and a phosphorescent material wherein the polymer comprises repeat units of formula (I): wherein A is a heteroaryl group containing a nitrogen atom, and A may be unusubstituted or substituted with one or more substituents; R 1 in each occurrence is independently a substituent; and n is 0, 1, 2, 3 or 4.

Claims (48)

1. A composition comprising a polymer and a phosphorescent material wherein the polymer comprises repeat units of formula (III):

wherein:

R 1 in each occurrence is independently C 1-40 hydrocarbyl, —OR 11 , —SR 11 , —NR 11 2 , or —SiR 11 3 ; R 11 each occurrence is C 1-40 hydrocarbyl;

R 2 is a C 1-40 hydrocarbyl; and

n is 0, 1, 2, 3 or 4.

2. The composition according to claim 1 , wherein the polymer comprises one or more co-repeat units.

3. The composition according to claim 2 , wherein the polymer comprises an arylene co-repeat unit that may be unsubstituted or substituted with one or more substituents.

4. The composition according to claim 2 , wherein the one or more co-repeat units include a conjugation-breaking repeat unit that does not provide any conjugation path between repeat units adjacent to the conjugation-breaking repeat unit.

5. The composition according to claim 4 , comprising one or more co-repeat units of formula (II):

wherein:

Ar 1 in each occurrence independently represent an aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents; and

Sp represents a spacer group comprising at least one carbon or silicon atom.

6. The composition according to claim 1 , wherein the phosphorescent material is mixed with the polymer.

7. The composition according to claim 1 , wherein the phosphorescent material is covalently bound to the polymer.

8. The composition according to claim 1 , wherein the phosphorescent material has a photoluminescent spectrum with a peak in the range of 420-490 nm.

9. A formulation comprising the composition according to claim 1 and at least one solvent.

10. An organic light-emitting device comprising an anode, a cathode and a light-emitting layer between the anode and cathode wherein the light-emitting layer comprises the composition according to claim 1 .

11. A polymer comprising a repeat unit of formula (III):

wherein:

R 2 is a C 1-40 hydrocarbyl;

R 1 in each occurrence is independently C 1-40 hydrocarbyl, —OR 11 , —SR 11 , —NR 11 2 , or —SiR 11 3 ; R 11 each occurrence is C 1-40 hydrocarbyl; and

n is 0, 1, 2, 3 or 4.

12. The composition of claim 1 , wherein the polymer further comprises a repeat unit of formula:

wherein q is 0, 1, 2, 3 or 4 and R 3 independently in each occurrence is selected from the group consisting of:

alkyl, wherein one or more non-adjacent C atoms may be replaced with optionally substituted aryl or heteroaryl, O, S, substituted N, C═O or —COO—, and one or more H atoms may be replaced with F;

aryl or heteroaryl groups that may be unsubstituted or substituted with one or more C 1-20 alkyl groups;

a group of formula —(Ar 3 ) r wherein each Ar 3 is independently an aryl or heteroaryl group and r is at least 2, wherein each Ar 3 may be unsubstituted or substituted with one or more C 1-20 alkyl groups; and

a crosslinkable-group.

13. The composition according to claim 1 , wherein the polymer does not comprise a fluorene repeat unit.

14. The polymer according to claim 11 , wherein R 2 is an aromatic ring or a branched or linear chain of aromatic rings, wherein each ring may be unsubstituted or substituted with one or more substituents R 4 , wherein each R 4 is independently a C 1-20 alkyl, wherein one or more non-adjacent C atoms of the C 1-20 alkyl may be replaces with O or S, and one or more H atoms of the C 1-20 alkyl may be replaced with F.

15. The polymer according to claim 11 , wherein the polymer further comprises a repeat unit of formula (IX):

wherein;

Ar 8 and Ar 9 in each occurrence are independently selected from subsutitited or unsubstituted aryl or heteroaryl;

g is greater than or equal to 1;

R 13 is H or a substituent ; and

c and d are each independently 1, 2 or 3.

16. The polymer of claim 11 , wherein the polymer further comprises a repeat unit of formula

wherein q is 0, 1, 2, 3 or 4 and R 3 independently in each occurrence is selected from the group consisting of:

alkyl, wherein one or more non-adjacent C atoms may be replaced with optionally substituted aryl or heteroaryl, O, S, substituted N, C═O or —COO—, and one or more H atoms may be replaced with F;

aryl or heteroaryl groups that may be unsubstituted or substituted with one or more C 1-20 alkyl groups;

a group of formula —(Ar 3 ) r wherein each Ar 3 is independently an aryl or heteroaryl group and r is at least 2, wherein each Ar 3 may be unsubstituted or substituted with one or more C 1-20 alkyl groups; and

a crosslinkable-group.

17. The polymer according to claim 11 , wherein the polymer does not comprise a fluorene repeat unit.

18. A method of forming a polymer comprising the step of polymerising a monomer of formula (IV):

wherein LG is a leaving group capable of leaving in a coupling reaction to form a carbon-carbon bond with an aromatic or heteroaromatic group, and wherein

R 1 , R 2 and n are as defined in claim 1 .

19. The method according to claim 18 , wherein each LG is independently selected from the group consisting of halogens, boronic acids; boronic esters; sulfonic acids; and sulfonic esters.

20. The method according to claim 19 , wherein the polymerization is carried out in the presence of a metal catalyst.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNMENT RECORDATION PREVIOUSLY RECORDED ON REEL 033232 FRAME 0859. ASSIGNOR(S) HEREBY CONFIRMS THE OMISSION OF SECOND ASSIGNEE SUMITOMO CHEMICAL COMPANY LIMITED. Recorded Jan 29, 2015
From: STEUDEL, ANNETTE; BOURCET, FLORENCE; KAMTEKAR, KIRAN
To: CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL COMPANY LIMITED
Reel/Frame 034868/0232 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2014
From: STEUDEL, ANNETTE; BOURCET, FLORENCE; KAMTEKAR, KIRAN
To: CAMBRIDGE DISPLAY TECHNOLOGY LIMITED
Reel/Frame 033232/0859 →
Priority Claims (1)
GB 1223283.1 · Dec 21, 2012 · national
Continuity (1)
Related Publication 20140175415A1 · Jun 26, 2014