IP Library › Granted Patent US 9,190,620
Granted Patent B2
US 9,190,620 · App. 14/194,689 · Granted Nov 17, 2015

Organic electroluminescent materials and devices

Inventors: Lichang Zeng (Lawrenceville, NJ); Suman Layek (Lawrenceville, NJ); Harvey Wendt (Medford Lakes, NJ); Chuanjun Xia (Lawrenceville, NJ)
Assignee: Universal Display Corporation
H01L51/0074C07D333/76C07D409/04H01L51/005H01L51/0054H01L51/0072H01L51/5016H01L51/5024H01L51/5076H01L51/5096
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Quick Facts
Patent No.
US 9,190,620
App. No.
14/194,689
Granted
Nov 17, 2015
Kind
B2
Abstract

A novel compound containing terphenylene connected to dibenzothiophene, dibenzofuran or dibenzoselenophene that can be used as hosts in phosphorescent organic light-emitting device is disclosed.

Claims (45)

1. A compound having a structure according to a formula (I)

wherein A is selected from a group consisting of triphenylene, phenanthrene, anthracene, biphenyl, terphenyl, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, fluorene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, triazine, or combinations thereof;

wherein L is selected from a group consisting of a direct bond, benzene, biphenyl and terphenyl, pyridine, or combinations thereof, and wherein L is optionally further substituted with alkyl, halogen, hydrogen, deuterium, nitrite or aryl;

wherein B is selected from a group consisting of dibenzothiophene, dibenzofuran and dibenzoselenophene; and

wherein A and B are independently optionally further substituted with one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and for each of A and B, two adjacent substituents are optionally joined to form a ring.

2. The compound of claim 1 , wherein the compound is of formula (II) or (III)

wherein X is selected from a group consisting of O, S and Se.

3. The compound of claim 1 , wherein A is selected from the group consisting of

wherein X is S, O or Se; and

R 1 and R 2 are, independently, linear or branched alkyl with 1 to 12 carbon atoms, and R 1 and R 2 are optionally jointed to form a ring.

4. The compound of claim 1 , wherein B is selected from the group consisting of

5. The compound of claim 1 , wherein L is selected from the group consisting of a direct bond,

6. The compound of claim 1 , wherein the compound is selected from the group consisting of

7. A first device comprising a first phosphorescent organic light-emitting device, the phosphorescent organic light-emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having a formula (I)

wherein A is selected from a group consisting of triphenylene, phenanthrene, anthracene, biphenyl, terphenyl, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, fluorene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, triazine, or combinations thereof;

wherein L is selected from a group consisting of a direct bond, benzene, biphenyl and terphenyl, pyridine, or combinations thereof, and wherein L is optionally further substituted with alkyl, halogen, hydrogen, deuterium, nitrile or aryl;

wherein B is selected from a group consisting of dibenzothiophene, dibenzofuran and dibenzoselenophene; and

wherein A and B are independently optionally further substituted with one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and for each of A and B, two adjacent substituents are optionally joined to form a fused ring.

8. The first device of claim 7 , wherein the compound is of formula (II)

wherein X is selected from a group consisting of O, S and Se.

9. The first device of claim 7 , wherein A is selected from the group consisting of

wherein X is S, O or Se; and

R 1 and R 2 are, independently, linear or branched alkyl with 1 to 12 carbon atoms, and R 1 and R 2 are optionally jointed to form a ring.

10. The first device of claim 7 , wherein B is selected from the group consisting of

11. The first device of claim 7 , wherein L is selected from the group consisting of a direct bond,

12. The first device of claim 7 , wherein the compound is selected from the group consisting of

13. The first device of claim 7 , wherein the organic layer is an emissive layer and the compound of the formula (I) is a host.

14. The first device of claim 7 , wherein the organic layer further comprising a phosphorescent emissive dopant.

15. The first device of claim 14 , wherein the phosphorescent emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:

wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution;

wherein R a , R b , R c , and R d 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a fused ring or form a multidentate ligand.

16. The first device of claim 7 , wherein the organic layer is a blocking layer and the compound of the formula (I) is a blocking material in the organic layer.

17. The first device of claim 7 , wherein the organic layer is an electron transporting layer and the compound of the formula (I) is an electron transporting material in the organic layer.

18. The first device of claim 7 , wherein the first device is a consumer product.

19. The first device of claim 7 , wherein the first device is an organic light-emitting device.

20. The first device of claim 7 , wherein the first device comprises a lighting panel.

21. A formulation comprising the compound having a structure according to a formula (I)

wherein A is selected from a group consisting of triphenylene, phenanthrene, anthracene, biphenyl, terphenyl, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, fluorene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, triazine, or combinations thereof;

wherein L is selected from a group consisting of a direct bond, benzene, biphenyl and terphenyl, pyridine, or combinations thereof, and wherein L is optionally further substituted with alkyl, halogen, hydrogen, deuterium, nitrile or aryl;

wherein B is selected from a group consisting of dibenzothiophene, dibenzofuran and dibenzoselenophene; and

wherein A and B are independently optionally further substituted with one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and for each of A and B, two adjacent substituents are optionally joined to form a fused ring.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE FIRST WHEREAS CLAUSE IDENTIFIYING THE ASSIGNORS' INTEREST INSIDE THE ASSIGNMENT DOCUMENT PREVIOUSLY RECORDED AT REEL: 032330 FRAME: 0457. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 19, 2015
From: ZENG, LICHANG; LAYEK, SUMAN; WENDT, HARVEY; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 036886/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2014
From: ZENG, LICHANG; LAYEK, SUMAN; WENDT, HARVEY; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 032330/0457 →
Continuity (1)
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