IP Library Granted Patent US 9,450,192
Granted Patent B2
US 9,450,192 · App. 13/310,899 · Granted Sep 20, 2016

Carbazole derivative and organic electroluminescent devices utilizing the same and fabrication method thereof

Inventors: Banumathy Balaganesan (Taoyuan, TW); Kun-Feng Chiang (Taoyuan, TW); Huang-Ming Guo (Taoyuan, TW); Po-Wei Hsu (Taoyuan, TW)
Assignee: E-RAY OPTOELECTRONICS TECHNOLOGY
H01L51/0072C07D209/88C07D403/04C07D403/12C07D403/14C07D487/04C07D491/048C09K11/06H05B33/14C09K2211/1022C09K2211/1029C09K2211/1059H01L51/0061H01L51/0081H01L51/0085H01L51/5016H01L51/5056H01L51/5072H01L51/5096
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Quick Facts
Patent No.
US 9,450,192
App. No.
13/310,899
Granted
Sep 20, 2016
Kind
B2
Abstract

The present invention provides a carbazole derivative of formula (I) for an organic electroluminescent device: wherein Y represents a heteroatom selected from N, O, P, S, or a bicyclic or tricyclic heterocyclic ring; and Ar 1 and Ar 2 each independently represent an alkyl or aryl substituted or unsubstituted aromatic hydrocarbon, or an alkyl or aryl substituted or unsubstituted heterocyclic aromatic hydrocarbon.

Claims (39)

1. A carbazole derivative of formula (I) for an organic electroluminescent device:

wherein Y represents one selected from N, O, P, S, a bicyclic heterocyclic ring fused with the carbazole, and a tricyclic heterocyclic ring;

Ar 1 and Ar 2 are each independently selected from the group consisting of H, alkyl, phenyl, biphenylyl, naphthalenyl, terphenyl,

wherein Ar 1 and Ar 2 are each independently and optionally substituted by a substituent selected from the group consisting of alkyl, phenyl, alkoxy

and

when Y represents N, Ar 1 is selected from the group consisting of phenyl, biphenylyl, naphthalenyl and terphenyl, and Ar 2 represents

wherein Ar 1 and Ar 2 are each independently and optionally substituted by alkyl, or when Y represents N, Ar 1 and Ar 2 represents phenyl and biphenylyl respectively, and Ar 2 is substituted by

or the carbazole derivative is one of compounds represented by formulas (1-30) and (1-31):

when Y represents O, Ar 1 does not exist, and Ar 2 represents

when Y represents S, Ar 2 does not exist;

when Y represents the bicyclic heterocyclic ring fused with the carbazole, Ar 1 is selected from the group consisting of H, phenyl, biphenylyl, naphthalenyl and terphenyl, and Ar 2 is selected from the group consisting of H, alkyl,

wherein Ar 1 and Ar 2 are each independently and optionally substituted by a substituent selected from the group consisting of alkyl, phenyl and alkoxy; and

when Y represents a tricyclic heterocyclic ring, Ar 1 represents H, and Ar 2 represents

2. The carbazole derivative of claim 1 , wherein Y represents a bicyclic heterocyclic ring fused with the carbazole.

3. The carbazole derivative of claim 1 , being one of compounds represented by the following formulas:

4. An organic electroluminescent device, comprising: a carbazole derivative of claim 1 or 3 .

5. The organic electroluminescent device of claim 4 , further comprising a light emitting layer containing a phosphorescent dopant and at least one compound of the carbazole derivative of claim 1 or 3 .

6. The organic electroluminescent device of claim 5 , wherein the phosphorescent dopant is an organic metal complex comprising at least one metal selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.

7. The organic electroluminescent device of claim 5 , wherein the phosphorescent dopant is one of Ir(ppy) 3 , Ir(pq) 2 (acac), Ir(piq) 2 (acac), Ir(piq) 3 , FIrpic, and PtOEt 3 .

8. The organic electroluminescent device of claim 5 , wherein the content of the phosphorescent dopant in the light emitting layer is in the range of 1% by volume to 15% by volume based on the total content of the light emitting layer.

9. The organic electroluminescent device of claim 4 , further comprising a hole transporting layer containing at least one compound of the carbazole derivative of claim 1 or 3 .

10. The organic electroluminescent device of claim 4 , further comprising an electron transporting layer containing at least one compound of the carbazole derivative of claim 1 or 3 .

11. The organic electroluminescent device of claim 4 , further comprising a hole block layer; and an electron block layer, wherein one of the hole block layer and the electron block layer contains at least one compound of the carbazole derivative of claim 1 or 3 .

12. The organic electroluminescent device of claim 4 , further comprising:

a substrate;

an electrode; and

a sandwich structure formed between the substrate and electrode, wherein said sandwich structure has a hole transporting layer, an electron transporting layer, and a light emitting layer sandwiched between the hole transporting layer and electron transporting layer.

13. The organic electroluminescent device of claim 12 , wherein one of the hole transporting layer, electron transporting layer and light emitting layer contains at least one compound of the carbazole derivative of claim 1 or 3 .

14. A method for forming an organic electroluminescent device, comprising:

forming an hole injection layer on a substrate;

forming an hole transport layer on the hole injecting layer;

forming an light emitting layer on the hole transport layer having a phosphorescent dopant and at least one compound of the carbazole derivative of claim 1 or 3 ;

forming an electron transporting layer on the light emitting layer;

forming an electron injection layer on the electron transporting layer; and

forming an electrode on the electron injection layer.

15. The method of claim 14 , wherein the phosphorescent dopant is an organic metal complex comprising at least one metal selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.

16. The method of claim 14 , wherein the phosphorescent dopant is one of Ir(ppy) 3 , Ir(pq) 2 (acac), Ir(piq) 2 (acac), Ir(piq) 3 , FIrpic, and PtOEt 3 .

17. The method of claim 14 , wherein the content of the phosphorescent dopant in the light emitting layer is in the range of 1 wt % to 15 wt %.

18. The method of claim 14 , wherein the electrode is a cathode.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2011
From: BALAGANESAN, BANUMATHY; CHIANG, KUN-FENG; GUO, HUANG-MING; HSU, PO-WEI
To: E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD
Reel/Frame 027321/0959 →
Continuity (2)
Provisional Application 61420016 · Dec 6, 2010
Related Publication 20120175598A1 · Jul 12, 2012