Organic electroluminescent materials and devices

• US 9,647,217 B2
• Filed: 02/24/2014
• Issued: 05/09/2017
• Est. Priority Date: 02/24/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Lin, Chun, Zeng, Lichang, Xia, Chuanjun
• Primary Examiner(s): Leong, Nathan T
• Application Number:
  US14/188,297
• Publication Number:
  US 20150243904A1
• Time in Patent Office: 1,170 Days
• Field of Search: None
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

The present invention relates to novel organic compounds comprising at least two different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene. The compounds are useful for organic light-emitting diodes. The compounds are also useful for charge-transport and charge-blocking layers, and as hosts in the light-emissive layer for organic light emitting devices (OLEDs).

Claims

1. A compound having formula I:

A-L-B 

 

(I);

wherein A and B are each different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein A and B can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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 wherein two adjacent substituents can optionally join to form a fused ring;

wherein L is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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.

2. The compound of claim 1, wherein A including optional substituents and B including optional substituents are different.

3. The compound of claim 1, wherein the compound further comprises C;

wherein C is selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein C can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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;

wherein C is connected to A or B by L′

;

wherein L′

is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L′

can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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 3, wherein C is a different selection from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene than A and B.

5. The compound of claim 3, wherein A, B, and C have no further substitution.

6. The compound of claim 3, wherein no more than one of A, B, and C is aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, or aza-triphenylene.

7. The compound of claim 3 wherein L′

has from 1 to 24 carbon atoms.

8. The compound of claim 3, wherein L′

is selected from the group consisting of

9. The compound of claim 3, wherein the compound is selected from the group consisting of:

10. The compound of claim 1, wherein A and B have no further substitution.

11. The compound of claim 1, wherein A and B are each independently selected from the group consisting of N-phenyl carbazole, aza-(N-phenyl carbazole), dibenzofuran, dibenzothiophene, and triphenylene.

12. The compound of claim 1, wherein A is selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, and triphenylene;

and B is selected from the group consisting of aza-(N-phenyl carbazole), aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene.

13. The compound of claim 1, wherein L has from 1 to 24 carbon atoms.

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

15. The compound of claim 1, wherein A or B is (9-carbazolyl)-(N-phenyl-carbazole).

16. The compound of claim 1, wherein the aza-(N-phenyl carbazole) is selected from the group consisting of N-pyridyl carbazole, N-pyrazinyl carbazole, and N-triazinyl carbazole.

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

18. The compound of claim 1, wherein the compound is selected from the group consisting of compound 1 to compound 459 listed below:

19. The compound of claim 1, wherein A is dibenzothiophene, L is —

CH₂—

, and B is N-phenyl carbazole.

20. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

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

A-L-B 

 

(I);

wherein A and B are each different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein A and B can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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;

wherein L is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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.

21. A formulation comprising a compound having formula I:

A-L-B 

 

(I);

wherein A and B are each different selections selected from the group consisting of N-phenyl carbazole, dibenzofuran, dibenzothiophene, triphenylene, aza-(N-phenyl carbazole), aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, and aza-triphenylene;

wherein A and B can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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 wherein two adjacent substituents can optionally join to form a fused ring;

wherein L is selected from the group consisting of alkyl, cycloalkyl, substituted alkyl, and substituted cycloalkyl; and

wherein L can be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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.