Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds

• US 9,054,323 B2
• Filed: 03/15/2012
• Issued: 06/09/2015
• Est. Priority Date: 03/15/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Lam, Siu Tung, Lee, Chi Hang, Lam, Sze Kui
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/421,489
• Publication Number:
  US 20130241401A1
• Time in Patent Office: 1,181 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/40 Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/156 comprising a multilayered structure
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/81 Anodes
• CPC Class Codes: H10K 50/82 Cathodes
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• 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

Novel diarylamino phenyl carbazole compounds are provided. By appropriately selecting the nature of the diarylamino substituent and the substitution on the carbazole nitrogen, compounds with appropriate HOMO and LUMO energies can be obtained for use as materials in a secondary hole transport layer.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein R₃ and R₄ are independently selected from the group consisting of alkyl, heteroalkyl, arylalkyl, aryl, and heteroaryl.

3. The compound of claim 1, wherein R₃ and R₄ are hydrogen or deuterium.

4. The compound of claim 1, wherein the compound has the formula:

5. The compound of claim 1, wherein X is O or S.

6. The compound of claim 1, wherein Ar₁ and Ar₂ are aryl.

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

8. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode;

an emissive layer disposed between the anode and the cathode;

a hole injection layer disposed between the anode and the emissive layer;

a first hole transport layer disposed between the hole injection layer and the emissive layer; and

a second hole transport layer disposed between the first hole transport layer and the emissive layer; and

wherein the second hole transport layer comprises a compound of formula;

9. The first device of claim 8, wherein the second hole transport layer is disposed adjacent to the first hole transport layer.

10. The first device of claim 8, wherein the first hole transport layer is thicker than the second hole transport layer.

11. The first device of claim 8, wherein the first hole transport layer comprises a compound with the formula:

12. The first device of claim 8, wherein the triplet energy of the compound of Formula II is higher than the emission energy of the emissive layer.

13. The first device of claim 8, further comprising a first dopant material that is an emissive dopant comprising a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

14. The first device of claim 8, wherein the first device is a consumer product.

15. The first device of claim 8, wherein the first device is an organic light-emitting device.

16. The first device of claim 8, wherein the first device comprises a lighting panel.

17. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode;

a first organic layer disposed between the anode and the cathode; and

wherein the first organic layer comprises a compound of formula;

18. The first device of claim 17, wherein the first organic layer is an emissive layer.

19. The first device of claim 18, wherein the emissive layer is a phosphorescent emissive layer.