Hole transport materials having a sulfur-containing group

• US 8,652,653 B2
• Filed: 06/30/2009
• Issued: 02/18/2014
• Est. Priority Date: 06/30/2008
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Lin, Chun, Ma, Bin, Xia, Chuanjun, Wu, Yonggang, Kwong, Raymond
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/001,577
• Publication Number:
  US 20110163302A1
• Time in Patent Office: 1,694 Days
• Field of Search: 428/690, 428/917, 313/504, 313/505, 313/506, 257/40, 257/E51.032, 257/E51.026, 564/26, 564/426, 564/434, 548/340.4, 548/418, 548/440
• US Class Current: 428/690
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1018 Heterocyclic compounds
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/141 comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/344 comprising ruthenium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/348 comprising osmium
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• 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 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Novel materials are provided, having a single phenyl or a chain of phenyls where there is a nitrogen atom on each end of the single phenyl or chain of phenyls. The nitrogen atom may be further substituted with particular thiophene, benzothiophene, and triphenylene groups. Organic light-emitting devices are also provided, where the novel materials are used as a hole transport material in the device. Combinations of the hole transport material with specific host materials are also provided.

Claims

1. A composition of matter having the chemical structure:

2. The composition of matter of claim 1, wherein the part of the composition represented by Formula I is more specifically:

3. The composition of matter of claim 1, wherein at least one of R₂, R₃, and R₄ is

4. The composition of matter of claim 1, wherein at least one of R₂, R₃ and R₄ is

5. The composition of matter of claim 1, wherein both R₁ and R₂ are

7. The composition of matter of claim 1, wherein

at least one of R₂, R₃, and R₄ is selected from the group consisting of:

8. The composition of matter of claim 1, wherein

R₁ is selected from the group consisting of:

9. The composition of matter of claim 3, wherein the composition of matter has a structure selected from the group consisting of:

10. The composition of matter of claim 9, wherein the composition of matter has the structure:

11. The composition of matter of claim 4, wherein the composition of matter has a structure selected from the group consisting of:

12. The composition of matter of claim 11, wherein the composition of matter has the structure:

13. The composition of matter of claim 5, wherein the composition of matter has a structure selected from the group consisting of:

14. The composition of matter of claim 13, wherein the composition of matter has the structure:

6. A composition of matter having the chemical structure:

15. The composition of matter of claim 6, wherein the composition of matter has a structure selected from the group consisting of:

16. The composition of matter of claim 15, wherein the composition of matter has the structure:

17. An organic light emitting device comprising:

an anode;

a cathode;

an organic emissive layer, disposed between the anode and the cathode, the organic emissive layer further comprising a host and a phosphorescent dopant,

an organic hole transport layer comprising a hole transport material, disposed between the organic emissive layer and the anode, and in direct contact with the organic emissive layer;

wherein the hole transport material has the structure;

18. The device of claim 17, wherein the dopant is an organo-metallic iridium material.

19. The device of claim 17, wherein at least one of R₂, R₃, and R₄ is

20. The device of claim 19, wherein the host is a compound comprising a triphenylene containing benzo-fused thiophene.

21. A consumer product, wherein the consumer product includes an organic light emitting device that further includes a composition of matter having the chemical structure: