Organic electroluminescent element

• US 10,411,212 B2
• Filed: 10/02/2012
• Issued: 09/10/2019
• Est. Priority Date: 10/04/2011
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited, JOLED Inc.
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Kambe, Emiko, Nakamura, Masato, Endo, Jun, Funahashi, Masakazu, Morishita, Hironobu
• Primary Examiner(s): Garrett, Dawn L
• Application Number:
  US14/349,626
• Publication Number:
  US 20140246663A1
• Time in Patent Office: 2,534 Days
• CPC Class Codes: C07D 215/30 Metal salts; Chelates
• CPC Class Codes: C07D 235/08 Radicals containing only hydrogen and carbon atoms
• CPC Class Codes: C07D 241/36 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/14 Ortho-condensed systems
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: H10K 50/13 comprising stacked EL layers within one EL unit
• CPC Class Codes: H10K 50/19 Tandem OLEDs
• CPC Class Codes: H10K 59/17 Passive-matrix OLED displays
• CPC Class Codes: H10K 59/32 Stacked devices having two or more layers, each emitting at different wavelengths
• CPC Class Codes: H10K 59/38 comprising colour filters or colour changing media [CCM]
• CPC Class Codes: H10K 85/611 Charge transfer complexes
• CPC Class Codes: H10K 85/623 containing five rings, e.g. pentacene
• CPC Class Codes: H10K 85/624 containing six or more rings
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

An organic electroluminescence device including: an anode; a cathode; two or more emitting units that are disposed between the anode and the cathode, each unit having an emitting layer; and a charge-generating layer that is disposed between the emitting units, wherein the charge-generating layer comprises an N layer nearer to the anode and a P layer nearer to the cathode, and the P layer comprises a compound represented by the following formula (I).

Claims

1. A substrate comprising two or more adjacent organic electroluminescence devices, each organic electroluminescence device comprising:

an anode;

a cathode;

two or more emitting units that are disposed between the anode and the cathode, each unit having an emitting layer; and

a charge-generating layer that is disposed between the emitting units,

wherein the charge-generating layer comprises an N layer nearer to the anode and a P layer nearer to the cathode, and

the P layer comprises a compound represented by the following formula (I);

2. The substrate according to claim 1, wherein at least one of the emitting units comprises a hole-transporting layer, and the P layer of the charge-generating layer is contacted with the hole-transporting layer.

3. The substrate according to claim 1, wherein the N layer of the charge-generating layer comprises at least one selected from the group consisting of an electron-donating metal, an electron-donating metal compound and an electron-donating metal complex.

4. The substrate according to claim 3, wherein the N layer of the charge-generating layer comprises at least one selected from the group consisting_of an alkali metal, an alkali metal compound, an alkali metal-containing organic metal complex, an alkaline-earth metal, an alkaline-earth metal compound, an alkaline-earth metal-containing organic metal complex, a rare-earth metal, a rare-earth metal compound and a rare-earth metal-containing organic metal complex.

5. The substrate according to claim 1, wherein the N layer of the charge-generating layer comprises a nitrogen-containing heterocyclic compound.

6. The substrate according to claim 5, wherein the nitrogen-containing heterocyclic compound is represented by the following formula (9):

7. The substrate according to claim 1, wherein a material constituting the emitting layer(s) of at least one of the emitting units is different from a material constituting the emitting layer(s) of other emitting unit(s).

8. The substrate_according to claim 1, wherein at least one of the emitting units comprises a hole-transporting region, and the P layer of the charge-generating region is contacted with the hole-transporting region.

9. The substrate according to claim 8, wherein the hole-transporting region comprises an aromatic amine derivative represented by the following formula (4):

10. The substrate according to claim 8, wherein the hole-transporting region comprises an aromatic amine derivative represented by the following formula (5):

12. The substrate according to claim 1, wherein the compound represented by the formula (I) is a compound represented by any one of the following formulas (II) to (X):

13. The substrate according to claim 1, wherein the compound represented by the formula (I) is a compound represented by any one of the following formulas (I-a) to (I-r):

14. The substrate according to claim 1, wherein the P layer of the charge-generating layer consists of the compound represented by the formula (I).

15. The substrate according to claim 1, wherein in the formula (I), Ar¹ is a benzene ring, a pyrazine ring, or a pyridine ring.

16. The substrate according to claim 15, wherein R¹ and R² are not bonded to each other to form a ring, R³ and R⁴ are not bonded to each other to form a ring, and adjacent groups of R¹ to R⁵ are not bonded to each other to form a ring.

17. The substrate according to claim 16, wherein R¹ to R⁴ may be the same or different from each other, and a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a halogen atom, a substituted or unsubstituted fluoroalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted fluoroalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group.

18. The substrate of claim 1, wherein the anode of each organic electroluminescence device is a stripe shape.

19. The substrate of claim 1, wherein in the compound of formula (1)

Y¹ to Y⁴ are —

CH═

;

and

at least one of R¹ and R² and at least one or R³ and R⁴ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted fluoroalkoxy group.

20. The substrate of claim 19, wherein the emitting layer disposed nearer to the cathode is a blue emitting layer comprising:

an anthracene derivative represented by the following formula (1);

11. The substrate according to claim I, wherein the compound represented by the formula (I) is a compound represented by the following formula (I-A) or (I-B):