Organic electroluminescent material and electroluminescent device by using the same

• US 20040146742A1
• Filed: 01/24/2003
• Published: 07/29/2004
• Est. Priority Date: 01/24/2003
• Status: Active Grant

• Current Assignee: RITDISPLAY CORPORATION
• Original Assignee: RITDISPLAY CORPORATION
• Inventors: Hsu, Hsiang Lun, Leung, Man-Kit, Wang, Shen-Shen
• Granted Patent: US 7,029,764 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/58 Naphthylamines; N-substituted derivatives thereof
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• 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 2211/1029 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: C09K 2211/1096 containing other heteroatoms
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• 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 85/653 comprising only oxygen as heteroatom
• CPC Class Codes: H10K 85/655 : comprising only sulfur as heteroatom
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

An organic electroluminescent material of the formula:

wherein R¹, R² and R³ are selected from the group consisting of hydrogen, halogen, nitryl, alkyl, cycloalkyl, alkyloxy, alkenyl, amine, aryl, polyaryl, arylalkyl, and propenyloxy, Ar³ is at least one selected from the group consisting of aryl and polyaryl and A and B are at least one selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkyloxy, alkenyl, amine, aryl, polyaryl, arylalkyl, and propenyloxy. This invention also discloses an electroluminescent device having the organic electroluminescent material.

Claims

1. An organic electroluminescent material of the formula:

2. The organic electroluminescent material of claim 1, wherein R¹, R² and R³ are at least one selected from the substituted or unsubstituted group consisting of alkyl having 1 to 10 carbon atoms, cycloalkyl having 1 to 10 carbon atoms, alkyloxy having 1 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, amine, aryl having 6 to 30 carbon atoms, polyaryl having 6 to 30 carbon atoms, arylalkyl having 6 to 30 carbon atoms, and propenyloxy having 1 to 10 carbon atoms.

3. The organic electroluminescent material of claim 1, wherein Ar³ is at least one selected from the substituted or unsubstituted group consisting of aryl having 6 to 30 carbon atoms, and polyaryl having 6 to 30 carbon atoms.

4. The organic electroluminescent material of claim 3, wherein Ar³ bonds with A.

5. The organic electroluminescent material of claim 3, wherein Ar³ bonds with B.

6. The organic electroluminescent material of claim 3, wherein Ar³ is at least one selected from the group consisting of

7. The organic electroluminescent material of claim 1, wherein A and B are at least one selected from the substituted or unsubstituted group consisting of alkyl having 1 to 10 carbon atoms, cycloalkyl having 1 to 10 carbon atoms, alkyloxy having 1 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, amine, aryl having 6 to 30 carbon atoms, polyaryl having 6 to 30 carbon atoms, arylalkyl having 6 to 30 carbon atoms, and propenyloxy having 1 to 10 carbon atoms.

8. An organic electroluminescent device comprising two electrodes and at least one organic electroluminescent layer sandwiched between the electrodes, wherein the organic electroluminescent layer comprises an organic electroluminescent material of the formula:

9. The device of claim 8, wherein R¹, R² and R³ are at least one selected from the substituted or unsubstituted group consisting of alkyl having 1 to 10 carbon atoms, cycloalkyl having 1 to 10 carbon atoms, alkyloxy having 1 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, amine, aryl having 6 to 30 carbon atoms, polyaryl having 6 to 30 carbon atoms, arylalkyl having 6 to 30 carbon atoms, and propenyloxy having 1 to 10 carbon atoms.

10. The device of claim 8, wherein Ar³ is at least one selected from the substituted or unsubstituted group consisting of aryl having 6 to 30 carbon atoms, and polyaryl having 6 to 30 carbon atoms.

11. The device of claim 10, wherein Ar³ bonds with A.

12. The device of claim 10, wherein Ar³ bonds with B.

13. The device of claim 10, wherein Ar³ is at least one selected from

14. The device of claim 8, wherein A and B are at least one selected from the substituted or unsubstituted group consisting of alkyl having 1 to 10 carbon atoms, cycloalkyl having 1 to 10 carbon atoms, alkyloxy having 1 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, amine, aryl having 6 to 30 carbon atoms, polyaryl having 6 to 30 carbon atoms, arylalkyl having 6 to 30 carbon atoms, and propenyloxy having 1 to 10 carbon atoms.

15. The device of claim 8, wherein the organic electroluminescent layer further comprises an aryl amino compound.

16. The device of claim 15, wherein the aryl amino compound is substituted with aryl group.

17. The device of claim 15, wherein the aryl amino compound is substituted with polyaryl group.

18. The device of claim 15, wherein the glass transition temperature of the organic electroluminescent layer is higher than 100°

C.

19. The device of claim 8, wherein the organic electroluminescent material is doped in the organic electroluminescent layer.

20. The device of claim 19, wherein the doping ratio of the organic electroluminescent material is greater than 0.01 wt %.

21. The device of claim 19, wherein the doping ratio of the organic electroluminescent material is less than 10 wt %.

22. The device of claim 8, wherein the organic electroluminescent material is doped in a hole transporting layer of the organic electroluminescent layer.