Electroluminescent devices

• US 20040151943A1
• Filed: 02/04/2003
• Published: 08/05/2004
• Est. Priority Date: 02/04/2003
• Status: Active Grant

• Current Assignee: Intellectual Ventures II LLC (Intellectual Ventures LLC)
• Original Assignee: CityU Research Limited
• Inventors: Lee, Shuit-Tong, Wang, Peng-Fei, Lee, Chun-Sing, Mi, Bao-Xiu
• Granted Patent: US 7,232,617 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C07D 209/88 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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 50/14 Carrier transporting layers
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

A compound of formula [I]:

X—R  [I]

wherein X represents the group:

and R is either (i) represented by the formula [II]

wherein n is 1 or 2, and the or each R₇ group is independently selected from the group consisting of hydrogen and halogen atoms, cyano, nitro, mercapto, carbonyl and sulfone groups, and optionally substituted alkyl, haloalkyl, hydroxyalkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylthio, arylthio, ester, siloxy, cyclic hydrocarbon and heterocyclic groups;

or (ii) is selected from the group consisting of optionally substituted alkyl, hydroxyalkyl, aryl, cyclic hydrocarbon and heterocyclic groups;

wherein in each case R₁-R₆ are each independently selected from the group consisting of hydrogen and halogen atoms, cyano, nitro, mercapto, carbonyl and sulfone groups, and optionally substituted alkyl, haloalkyl, hydroxyalkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylthio, arylthio, ester, siloxy, cyclic hydrocarbon and heterocyclic groups. The compounds are useful as hole-transporting materials in electroluminescence devices.

Claims

1. A compound of formula [I]:

X—

R 

 

[I]

wherein X represents the group;

2. The compound of claim 1 having formula [III]:

3. The compound of claim 2 wherein R is selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

4. The compound of claim 1 having formula [IV]:

5. The compound of claim 4 wherein the or each R₇ group is independently selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

6. The compound of claim 1 having the formula [V]:

7. The compound of claim 6 wherein the or each R₇ group is independently selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

8. The compound of any of claims 1 to 7 wherein R₁-R₆ are selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

9. The compound of claim 8 wherein R₁-R₆ are hydrogen atoms.

10. An organic electroluminescence device comprising

an anode;

a cathode;

a hole transporting layer; and

an electron transporting layer;

wherein the hole-transporting layer is disposed between the anode and the electron-transporting layer and the electron-transporting layer is disposed between the cathode and the hole-transporting layer, and the hole-transporting layer comprises a compound of formula [I]

X—

R 

 

[I]

wherein X represents the group;

and R is either (i) represented by the formula [II]

wherein n is 1 or 2, and the or each R₇ group is independently selected from the group consisting of hydrogen and halogen atoms, cyano, nitro, mercapto, carbonyl and sulfone groups, and optionally substituted alkyl, haloalkyl, hydroxyalkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylthio, arylthio, ester, siloxy, cyclic hydrocarbon and heterocyclic groups;

or (ii) is selected from the group consisting of optionally substituted alkyl, hydroxyalkyl, aryl, cyclic hydrocarbon and heterocyclic groups;

wherein in each case R₁-R₆ are each independently selected from the group consisting of hydrogen and halogen atoms, cyano, nitro, mercapto, carbonyl and sulfone groups, and optionally substituted alkyl, haloalkyl, hydroxyalkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylthio, arylthio, ester, siloxy, cyclic hydrocarbon and heterocyclic groups.

11. An organic electroluminescence device according to claim 10 wherein the hole transporting layer comprises a compound of formula [III]

12. An organic electroluminescence device according to claim 10 wherein R is selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

13. An organic electroluminescence device according to claim 10 wherein the hole transporting layer comprises a compound of formula [IV]:

14. An organic electroluminescence device according to claim 10 wherein the or each R₇ group is independently selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

15. An organic electroluminescence device according to claim 10 wherein the hole-transporting layer comprises a compound of formula [V]:

16. An organic electroluminescence device according to claim 10 wherein the or each R₇ group is independently selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

17. An organic electroluminescence device according to claim 10 wherein R₁-R₆ are selected from the group consisting of alkyl, haloalkyl, aryl and heterocyclic groups.

18. An organic electroluminescence device according to claim 10 wherein R₁-R₆ are hydrogen atoms.

19. An organic electroluminescence device according to claim 10 wherein a luminescent material is incorporated in the electron transporting layer.

20. An organic electroluminescence device according to claim 10 wherein a luminescent material is incorporated in the hole transporting layer.

21. An organic electroluminescence device according to claim 10 wherein a luminescent layer is disposed between the electron transporting layer and the hole transporting layer.

22. An organic electroluminescence device according to claim 10 wherein the hole transporting layer comprises an additional hole transporting compound selected from the group consisting of optionally substituted phthalocyanine derivatives, napththalocyanine derivatives, porphyrin derivatives, pyrazoline derivatives, carbazole derivatives, thiophene derivatives, aromatic tertiary amine derivatives, benzidine derivatives, triphenylamine derivatives, polyvinylcarbazole and polysilane.

23. An organic electroluminescence device according to claim 22 wherein the additional hole transporting compound has a structure selected from the group consisting of:

24. An organic electroluminescence device according to claim 10 additionally comprising a hole injection material disposed between the anode and the hole transporting layer.

25. A method of using a compound of formula [I] in an electroluminescence device:

X—

R 

 

[I]

wherein X represents the group;