Organic electroluminescent material and organic electroluminescent element by using the same

• US 7,026,061 B2
• Filed: 03/17/2003
• Issued: 04/11/2006
• Est. Priority Date: 03/17/2003
• Status: Expired due to Fees

• Current Assignee: RITDISPLAY CORPORATION
• Original Assignee: RITDISPLAY CORPORATION
• Inventors: Hsu, Hsiang Lun, Wang, Shen-shen, Liu, Jui Hsiung, Huang, Heh Lung, Hsieh, Tzu Lin
• Primary Examiner(s): GARRETT, DAWN L
• Application Number:
  US10/388,513
• Publication Number:
  US 20040183432A1
• Time in Patent Office: 1,121 Days
• Field of Search: 257/40, 428/690, 428/917, 313/506, 544/224, 544/338
• US Class Current: 428/690
• 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: 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 85/324 comprising aluminium, e.g. Alq3
• 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: Y10S 428/917 Electroluminescent

Abstract

An organic electroluminescent material of the formula:

• • wherein M is at least one selected from the group consisting of —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂C(CH₃)₂CH₂—, and —CH₂YCH₂—, X is at least one selected from the group consisting of oxygen, sulfur, nitrogen, carbon, alkyl, silicon, silyl, phosphorus, aryl, and polyaryl, and n is depending on the amount of free radicals of X. Y is at least one selected from the group consisting of oxygen, sulfur, nitrogen and SiR¹R². Wherein, R¹ and R² is at least one selected from the group consisting of substituted or unsubstituted alkyl having 1 to 10 carbon atoms, and substituted or unsubstituted aryl having 6 to 30 carbon atoms. This invention also discloses an organic electroluminescent element having the organic electroluminescent material.

Claims

1. An organic electroluminescent material of the formula:

wherein M is at least one selected from the group consisting of —

CH₂—

, —

CH₂CH₂—

, —

CH₂CH₂CH₂—

, —

CH₂C(CH₃)₂CH₂—

, and —

CH₂YCH₂—

, X is at least one selected from the group consisting of oxygen, sulfur, nitrogen, carbon, alkyl, silicon, silyl, phosphorus, aryl, and polyaryl, n is depending on the amount of free radicals of X, and Y is at least one selected from the group consisting of oxygen, sulfur, nitrogen and SiR¹R², R¹ and R² being at least one selected from the group consisting of substituted or unsubstituted alkyl having 1 to 10 carbon atoms, and substituted or unsubstituted aryl having 6 to 30 carbon atoms.

2. The organic electroluminescent material of claim 1, wherein X is at least one selected from the group consisting of:

wherein, R is at least one selected from the group consisting of hydrogen, halogen, nitryl, alkyl, cycloalkyl, alkyloxy, alkenyl, amine, aryl, polyaryl, arylalkyl, and propenyloxy.

3. The organic electroluminescent material of claim 1, wherein R¹ and R² are at least one selected from the substituted or unsubstituted group consisting of cycloalkyl having 1 to 10 carbon atoms, polyaryl having 6 to 30 carbon atoms, and arylalkyl having 6 to 30 carbon atoms.

4. The organic electroluminescent material of claim 1, wherein X 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.

5. The organic electroluminescent material of claim 4, wherein X is at least one selected from the group consisting of:

wherein, R is at least one selected from the group consisting of hydrogen, halogen, nitryl, alkyl, cycloalkyl, alkyloxy, alkenyl, amine, aryl, polyaryl, arylalkyl, and propenyloxy.

6. The organic electroluminescent material of claim 5, wherein R is 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 3 to 10 carbon atoms.

7. The organic electroluminescent material of claim 1, wherein X has at least two free radicals, and n is at least 2.

8. An organic electroluminescent element 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:

wherein M is at least one selected from the group consisting of —

CH₂—

, —

CH₂CH₂—

, —

CH₂CH₂CH₂—

, —

CH₂C(CH₃)2CH2—

, and —

CH₂YCH₂—

, X is at least one selected from the group consisting of oxygen, sulfur, nitrogen, carbon, alkyl, silicon, silyl, phosphorus, aryl, and polyaryl, n is depending on the amount of free radicals of X, and Y is at least one selected from the group consisting of oxygen, sulfur, nitrogen and SiR¹R², R¹ and R² being at least one selected from the group consisting of substituted or unsubstituted alkyl having 1 to 10 carbon atoms, and substituted or unsubstituted aryl having 6 to 30 carbon atoms.

9. The element of claim 8, wherein X 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.

10. The element of claim 8, wherein X is at least one selected from the group consisting of:

wherein, R is at least one selected from the group consisting of hydrogen, halogen, nitryl, alkyl, cycloalkyl, alkyloxy, alkenyl, amine, aryl, polyaryl, arylalkyl, and propenyloxy.

11. The element of claim 10, wherein R is 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 3 to 10 carbon atoms.

12. The element of claim 10, wherein X 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.

13. The element of claim 12, wherein X is at least one selected from the group consisting of:

wherein, R is at least one selected from the group consisting of hydrogen, halogen, nitryl, alkyl, cycloalkyl, alkyloxy, alkenyl, amine, aryl, polyaryl, arylalkyl, and propenyloxy.

14. The element of claim 13, wherein R is 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 element of claim 8, wherein X has at least two free radicals, and n is at least 2.

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

17. The element of claim 16, wherein the aryl amino compound is substituted with aryl group.

18. The element of claim 16, wherein the aryl amino compound is substituted with polyaryl group.

19. The element of claim 16, wherein the glass transition temperature of the organic electroluminescent layer is higher than 100°

C.

20. The element of claim 8, wherein the organic electroluminescent material is doped in the organic electroluminescent layer.

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

22. The element of claim 20, wherein the doping ratio of the organic electroluminescent material is less than 10 wt%.

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