Organic electroluminescent materials and devices

• US 9,627,631 B2
• Filed: 10/08/2015
• Issued: 04/18/2017
• Est. Priority Date: 07/30/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond
• Primary Examiner(s): Zucker, Paul A
• Assistant Examiner(s): LUDERER, MARK R
• Application Number:
  US14/878,497
• Publication Number:
  US 20160028016A1
• Time in Patent Office: 558 Days
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons

Abstract

Boron-nitrogen polyaromatic compounds having a fused aromatic ring system are provided, where the compounds include a [1,2]azaborino[1,2-a][1,2]azaborine

which is optionally fused to one or more aromatic rings or fused aromatic rings; wherein the fused aromatic ring system is substituted by one or more substituents, R, that are not fused to the aromatic ring system, 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 wherein any two adjacent substituents, R, are optionally joined to form one or more non-aromatic rings. Devices, such as organic light emitting devices (OLEDs) that comprise light emitting materials are also provided.

Claims

1. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound that comprises;

a fused aromatic ring system that includes a [1,2]azaborino[1,2-a][1,2]azaborine

2. The first device of claim 1, wherein the organic layer is an emissive layer and the compound of Formula (I) is an emissive dopant.

3. The first device of claim 1, wherein the organic layer is an emissive layer and the compound of Formula (I) is a host.

4. The first device of claim 1, wherein the organic layer is a hole injecting layer or a hole transporting layer.

5. The first device of claim 1, wherein the organic layer is an electron injecting layer or an electron transporting layer.

6. The first device of claim 1, wherein the organic layer is an exciton blocking layer.

7. The first device of claim 1, wherein the fused aromatic ring system exhibits delayed fluorescence.

8. The first device of claim 1, wherein the fused aromatic ring system is selected from the group consisting of:

9. The first device of claim 1, wherein the fused aromatic ring system is

10. The first device of claim 1, wherein R is selected from the group consisting of alkyl, cycloalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof.

11. The first device of claim 1, wherein the compound is a compound of Formula (II), Formula (III), or Formula (IV):

12. The first device of claim 11, wherein R₁ to R₂₂ are each independently selected from the group consisting of aryl, heteroaryl, and NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

13. The first device of claim 11, wherein the compound is a compound of Formula (II) and at least one of R₅, R₈, R₁₃, or R₁₆ is not hydrogen or deuterium.

14. The first device of claim 11, wherein the compound is a compound of Formula (III) or Formula (IV), and at least one of R₈, R₁₁, R₁₉, or R₂₂ is not hydrogen or deuterium.

15. The first device of claim 11, wherein the compound is a compound of Formula (II) and at least one of R₅, R₈, R₁₃, or R₁₆ is aryl, heteroaryl, or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

16. The first device of claim 11, wherein the compound is a compound of Formula (III) or Formula (IV), and at least one of R₈, R₁₁, R₁₉, or R₂₂ is aryl, heteroaryl, or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

17. The first device of claim 11, wherein the compound is a compound of Formula (II) and at least one of R₁, R₄, R₉, or R₁₂ is aryl, heteroaryl, or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

18. The first device of claim 11, wherein the compound is a compound of Formula (III) or Formula (IV), and at least one of R₈, R₁₁, R₁₉, or R₂₂ is aryl, heteroaryl, or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

19. The first device of claim 1, wherein the compound is selected from the group consisting of: