Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9419225-B2
Application number	US-201313803044-A
Country	US
Kind code	B2
Filing date	Mar 14, 2013
Priority date	Mar 14, 2013
Publication date	Aug 16, 2016
Grant date	Aug 16, 2016

Abstract

A compound according to a formula I, devices incorporating the same, and formulations including the same are described. The compound according to the formula I can have the structure wherein R1, R2, R3, R4, R5 and R6 each represent mono, di, tri, tetra substitutions, or no substitution, R9 represents mono, di, tri substitutions, or no substitution, R1, R2, R3, R4, R5, R6 and R9 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. A1, A2, A3, A4, A5, and A6 are each independently selected from N or C and n is an integer from 1 to 20.

First claim

What is claimed is:

1. A compound having a structure selected from the group consisting of formula II, III, IV, and V:

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each represent mono, di, tri, tetra substitutions, or no substitution;
R 9 represents mono, di, tri substitutions, or no substitution;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
A 1 , A 2 , A 3 , A 4 , and A 5 are each C;
n is an integer from 1 to 20; and
wherein, if the compound has a structure of formula (II) or formula (IV):
(a) n is an integer from 2 to 20, or
(b) at least one of R 1 -R 6 , and R 9 is not hydrogen, or
(c) both (a) and (b) are true.

2. The compound of claim 1 , wherein the compound has a structure of formula IV:

3. The compound of claim 1 , wherein the compound has a formula VI:

wherein
R 7 and R 8 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

4. The compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are each independently selected from the group consisting of hydrogen, deuterium, silyl, aryl, and heteroaryl.

5. The compound of claim 1 , wherein n is an integer from 1 to 5.

6. The compound of claim 1 , wherein
n is an integer from 1 to 3; and
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are each independently selected from the group consisting of hydrogen and phenyl.

7. The compound of claim 6 , wherein n is 1; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are hydrogen.

8. The compound of claim 1 , wherein n is 2.

9. A first device comprising an organic light-emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure selected from the group consisting of formula II, III, IV, and V:

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each represent mono, di, tri, tetra substitutions, or no substitution;
R 9 represents mono, di, tri substitutions, or no substitution;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
A 1 , A 2 , A 3 , A 4 , and A 5 are each C;
n is an integer from 1 to 20; and
wherein, if the compound has a structure of formula (II) or formula (IV):
(a) n is an integer from 2 to 20, or
(b) at least one of R 1 -R 6 , and R 9 is not hydrogen, or
(c) both (a) and (b) are true.

10. The first device of claim 9 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are each independently selected from the group consisting of hydrogen, deuterium, silyl, aryl, and heteroaryl.

11. The first device of claim 9 , wherein the organic layer is an emissive layer and the compound of the formula I is a host.

12. The first device of claim 11 , wherein the organic layer further comprises an emissive dopant.

13. The first device of claim 12 , wherein the emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:

wherein
R a , R b , and R c may represent mono, di, tri or tetra substitutions;
R a , R b , and R c are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
two adjacent substituents of R a , R b , and R c are optionally joined to form a fused ring.

14. The first device of claim 9 , wherein the organic layer is a blocking layer and the compound having the formula I is a blocking material in the organic layer.

15. The first device of claim 9 , wherein the organic layer is an electron transporting and the compound having formula I is an electron transporting material in the organic layer.

16. The first device of claim 9 , wherein the first device is a consumer product.

17. The first device of claim 9 , wherein the first device is an organic light-emitting device.

18. The first device of claim 9 , wherein the first device comprises a lighting panel.

19. A composition comprising a compound of claim 1 .

20. The first device of claim 9 , wherein the compound of the formula I is selected from the group consisting of:

21. The compound of claim 1 , wherein the compound is selected from a group consisting of:

Assignees

• Xia Chuanjun
• Adamovich Vadim
• Wu Yonggang
• Zeng Lichang
• Universal Display Corp

Inventors

• Xia Chuanjun
• Adamovich Vadim
• Wu Yonggang
• Zeng Lichang

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/5016

  Electricity · mapped topic