IP Library Granted Patent US 9,515,277
Granted Patent B2
US 9,515,277 · App. 12/935,416 · Granted Dec 6, 2016

Organic electroluminescent element, organic EL display device and organic EL illumination

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Quick Facts
Patent No.
US 9,515,277
App. No.
12/935,416
Granted
Dec 6, 2016
Kind
B2
Abstract

To provide an organic electroluminescent element having a low driving voltage, high current efficiency and high voltage efficiency. An organic electroluminescent element comprising an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a mixed layer containing a light-emitting low molecular compound and/or a charge-transporting low molecular compound in a film containing an insolubilized polymer obtained by insolubilizing an insolubilizing polymer, and, adjacent to the mixed layer, a layer containing a light-emitting low molecular compound and a charge-transporting low molecular compound and not containing an insolubilized polymer.

Claims (61)

1. An organic electroluminescent element, comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode;

wherein:

the organic layer comprises a first layer and a second layer adjacent to the first layer;

the first layer comprises in a single, mixed layer: (i) at least one of a light-emitting low molecular weight compound and a charge-transporting low molecular weight compound, and (ii) an insolubilized polymer;

the second layer comprises in a single, mixed layer: (i) a light-emitting low molecular weight compound, and (ii) a charge-transporting low molecular weight compound;

the insolubilized polymer is obtained by insolubilizing an insolubilizing polymer;

the insolubilizing polymer comprises a charge transporting moiety; and

the second layer is free of insolubilized polymers.

2. The organic electroluminescent element according to claim 1 , wherein the insolubilizing polymer is selected from the group consisting of cross-linking polymers, dissociating polymers, and eliminating polymers.

3. The organic electroluminescent element according to claim 1 , wherein the insolubilizing polymer comprises at least one repeating unit represented by formula (2):

wherein:

m is an integer of from 0 to 3;

each of Ar 11 and Ar 12 is independently a direct bond, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent;

each of Ar 13 and Ar 15 is independently an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent; and

Ar 11 and Ar 12 are not direct bonds at the same time.

4. The organic electroluminescent element according to claim 2 , wherein:

the insolubilized polymer is a cross-linking polymer;

the cross-linking polymer has a number of cross-linking groups of from 0.5 to 10 groups per molecular weight of 10,000; and

the molecular weight is calculated from a molar ratio and structural formulae of charged monomers, excluding terminal groups of the cross-linking polymer.

5. An organic EL display device comprising the organic electroluminescent element of claim 1 .

6. An organic EL illumination comprising the organic electroluminescent element of claim 1 .

7. A process for producing an organic electroluminescent element comprising an anode, a cathode and an organic layer disposed between the anode and the cathode, the process comprising:

forming an insolubilized film by applying an active energy to a film comprising an insolubilizing polymer; and

applying a composition comprising: (i) at least one of a light-emitting low molecular compound and a charge-transporting low molecular weight compound, and (ii) a solvent, on to the insolubilized film to form a film on the insolubilized film to obtain the organic layer;

wherein the insolubilizing polymer comprises a charge transporting moiety.

8. An organic electroluminescent element, comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode;

wherein:

the organic layer comprises a first layer and a second layer adjacent to the first layer;

the first layer comprises in a single, mixed layer: (i) an insolubilized polymer obtained by insolubilizing an insolubilizing polymer comprising a charge transporting moiety, and (ii) at least one of a light-emitting low molecular weight compound and a charge-transporting low molecular weight compound;

the second layer comprises in a single, mixed layer: (i) a light-emitting low molecular weight compound, and (ii) a charge-transporting low molecular weight compound;

the second layer is free of polymers; and

when the first layer is dipped for 60 seconds in each of water, ethyl benzoate, and a hydrocarbon solvent at a temperature of from 20 to 25° C., the first layer has a remaining film thickness of at least 95% of a film thickness of the first layer before the dipping.

9. The organic electroluminescent element according to claim 2 , wherein the insolubilizing polymer comprises at least one repeating unit represented by formula (2):

wherein:

m is an integer of from 0 to 3;

each of Ar 11 and Ar 12 is independently a direct bond, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent;

each of Ar 13 and Ar 15 is independently an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent; and

Ar 11 and Ar 12 are not direct bonds at the same time.

10. The organic electroluminescent element according to claim 9 , wherein:

the insolubilized polymer is a cross-linking polymer;

the cross-linking polymer has a number of cross-linking groups of from 0.5 to 10 groups per molecular weight of 10,000; and

the molecular weight is calculated from a molar ratio and structural formulae of charged monomers, excluding terminal groups of the cross-linking polymer.

11. An organic EL display device comprising the organic electroluminescent element of claim 2 .

12. An organic EL display device comprising the organic electroluminescent element of claim 3 .

13. An organic EL display device comprising the organic electroluminescent element of claim 9 .

14. An organic EL display device comprising the organic electroluminescent element of claim 4 .

15. An organic EL display device comprising the organic electroluminescent element of claim 10 .

16. An organic EL illumination comprising the organic electroluminescent element of claim 2 .

17. An organic EL illumination comprising the organic electroluminescent element of claim 3 .

18. An organic EL illumination comprising the organic electroluminescent element of claim 4 .

19. An organic EL illumination comprising the organic electroluminescent element of claim 9 .

20. An organic EL illumination comprising the organic electroluminescent element of claim 10 .

21. The organic electroluminescent element according to claim 1 , wherein the first layer comprises: (i) the charge-transporting low molecular weight compound, and (ii) the insolubilized polymer.

22. The organic electroluminescent element according to claim 7 , wherein the composition applied to the insolubilized film comprises: (i) the charge-transporting low molecular weight compound, and (ii) the solvent.

23. The organic electroluminescent element according to claim 8 , wherein the first layer comprises: (i) the polymer, and (ii) the charge-transporting low molecular weight compound.

Assignments (3)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
MERGER Recorded Sep 4, 2017
From: MITSUBISHI CHEMICAL CORPORATION
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 043750/0207 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2010
From: OKABE, KAZUKI; TAKAHASHI, ATSUSHI; ABE, TOMOHIRO; TSURUTANI, YASUYUKI; SATO, HIDEKI
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 025383/0379 →