Bis- and tris- (di) benzocarbazole-based materials as hole transport materials for organic light emitting devices

• US 20030186077A1
• Filed: 12/31/2001
• Published: 10/02/2003
• Est. Priority Date: 12/31/2001
• Status: Abandoned Application

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Chen, Jian P.
• Application Number:
  US10/029,936
• Publication Number:
  US 20030186077A1
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07D 209/80 [b, c]- or [b, d]-condensed
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons

Abstract

Compounds according to Formula I

wherein one or two of Ar1-4 are present, R is selected from the group consisting of H, CH₃, OCH₃ or halogen, and Ar is an aryl bridge. Such compounds are suitable for use in organic light-emitting devices. These compounds exhibit both hole transport and emissive properties and have a high glass transition temperature and thermal stability.

Claims

1. A compound having the structure of Formula I

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

3. The compound of claim 1, wherein the compound is a bis-dibenzocarbazole.

4. The compound of claim 3, wherein the compound is selected from the group consisting of 1,4,-bis-7H-dibenzo[c,g]carbazole-benzene, 4,4′

-bis-7H-dibenzo[c,g]carbazole-biphenyl, 2,7-bis-7H-dibenzo[c,g]carbazole-9,9-dimethyl-fluorene, 4,4′

-bis-13H-dibenzo[a,i]carbazole-biphenyl, 4,4′

-bis-13H-dibenzo[a,g]carbazole-biphenyl, 4,4′

-bis-2,12-dimethoxy-7H-dibenzo[c,g]carbazole-biphenyl, 2,7-bis-2,12-dimethoxy-7H-dibenzo[c,g]carbazole-9,9-dimethyl-fluorene, 1,4-bis-2,12-dimethoxy- 13H-dibenzo[c,g]carbazole-benzene, 1,4bis-2,12-dimethoxy-7H-dibenzo[c,g]carbazole-benzene, and 1,4-bis-13H-dibenzo[a,i]carbazole-benzene.

5. The compound of claim 1, wherein the compound is a bis-benzocarbazole.

6. The compound of claim 5, wherein the compound is selected from the group consisting of 4,4′

-bis-7H-benzo[c]carbazole-biphenyl, 1,4-bis-7H-benzo[c]carbazole-benzene, 4,4′

-bis-11H-benzo[a]carbazole-biphenyl, 1,4-bis-11H-benzo[a]carbazole-benzene, 1,3-bis-7H-benzo[c]carbazole-benzene, 1,3-bis-11H-benzo[a]carbazole-benzene, and 4,4′

-bis-3-phenyl- 11H-benzo[a]carbazole -biphenyl.

13. A method of making a compound according to claim 3 comprising the step of reacting one equivalent of a diiodo- or dibromo-aromatic compound and two equivalents of dibenzocarbazole in the presence of a metal catalyst.

14. A method of making a compound according to claim 5 comprising the step of reacting one equivalent of a diiodo- or dibromo-aromatic compound and two equivalents of benzocarbazole in the presence of a metal catalyst.

17. An organic light emitting device comprising:

(a) a transparent anode;

(b) a cathode; and

(c) an emission layer containing a compound according to any one of claims 1-12.

18. An organic light emitting device comprising:

(a) a transparent anode;

(b) a cathode;

(c) an emission layer; and

(d) a hole transport layer containing a compound according to any one of claims 1-12.

7. A compound having the structure of Formula II

8. The compound of claim 7, wherein Ar is selected from the group consisting

9. The compound of claim 7, wherein the compound is a tris-dibenzocarbazole.

10. The compound of claim 9, wherein the compound is 4,4′

,4″

-tris(N-dibenzo[a,g]carbazolyl)triphenylamine.

11. The compound of claim 7, wherein the compound is a tris-benzocarbazole.

12. The compound of claim 11, wherein the compound is selected from the group consisting of 4,4′

,4″

-tris(N-benzo[c]carbazolyl)triphenlyamine and 4,4′

,4″

-tris(N-benzo[a]carbazolyl)triphenylamine.

15. A method of making a compound according to claim 9 comprising the step of reacting one equivalent of a triiodo- or tribromo-aromatic compound and three equivalents of dibenzocarbazole in the presence of a metal catalyst.

16. A method of making a compound according to claim 11 comprising the step of reacting one equivalent of a triiodo- or tribromo-aromatic compound and three equivalents of benzocarbazole in the presence of a metal catalyst.