Organic EL multi-color light-emitting device

• US 10,276,637 B2
• Filed: 05/09/2012
• Issued: 04/30/2019
• Est. Priority Date: 05/13/2011
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited, JOLED Inc.
• Original Assignee: Idemitsu Kosan Company Limited, JOLED Inc.
• Inventors: Matsumoto, Toshiki, Yoshinaga, Tadahiko, Kato, Tomoki, Inoue, Tetsuya, Ito, Mitsunori, Yoshida, Kei, Ikeda, Kiyoshi, Eida, Mitsuru
• Primary Examiner(s): Murata, Austin
• Application Number:
  US14/114,880
• Publication Number:
  US 20140159023A1
• Time in Patent Office: 2,547 Days
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• 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: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/27 Combination of fluorescent and phosphorescent emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/131 with spacer layers between the electroluminescent layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 59/35 comprising red-green-blue [RGB] subpixels
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• 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
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

An organic EL multi-color emitting device including a substrate, and a first light-emitting element and a second light-emitting element arranged on the surface of the substrate; the first light-emitting element including, between an anode and a cathode, a first organic layer, a second organic layer and a third organic layer in this sequence in a direction perpendicular to the surface of the substrate; the second light-emitting element including, between an anode and a cathode, a second organic layer and a third organic layer in this sequence in a direction perpendicular to the surface of the substrate; the first organic layer including a first light-emitting dopant; the third organic layer including a second light-emitting dopant; the second organic layer including any of (A) a compound including an arylamine site, and a furan site or a thiophene site, (B) a compound including an arylamine site and a site comprising a nitrogen-containing six-membered ring structure, (C) a compound including a carbazole site, and a furan site or a thiophene site, and (D) a compound including a carbazole site and a site including a nitrogen-containing six-membered ring structure.

Claims

1. An organic EL multi-color light-emitting device comprising a substrate, and a first light-emitting element and a second light-emitting element arranged on the surface of the substrate;

the first light-emitting element comprising, between an anode and a cathode, a first organic layer, a second organic layer and a third organic layer in this sequence in a direction perpendicular to the surface of the substrate;

the second light-emitting element comprising, between an anode and a cathode, a second organic layer and a third organic layer in this sequence in a direction perpendicular to the surface of the substrate;

the second organic layer of the first light-emitting element and the second organic layer of the second light-emitting element comprise the same compound, and the third organic layer of the first light-emitting element and the third organic layer of the second light-emitting element may be the same or different;

the first organic layer comprising a first light-emitting dopant;

the third organic layer of the first light-emitting element and the third organic layer of the second light-emitting element comprising a second light-emitting dopant, and the third organic layer of the first light-emitting element is an electron-injecting and/or electron-transporting layer;

the second organic layer of the first light-emitting element and the second organic layer of the second light-emitting element comprising any of the following compounds (A) to (D);

(A) a compound comprising an arylamine site, and a furan site or a thiophene site,

(B) a compound comprising an arylamine site and a site comprising a nitrogen-containing six-membered ring structure,

(C) a compound comprising a carbazole site, and a furan site or a thiophene site, and

(D) a compound comprising a carbazole site and a site comprising a nitrogen-containing six membered ring structure,

wherein the first and second light-emitting elements emit different color light, and

the thickness of the second organic layer of the first light-emitting element is the same as the thickness of the second organic layer of the second light-emitting element.

2. The organic EL multi-color light-emitting device according to claim 1, wherein the compounds (A) to (D) are a compound represented by the following formula (1) or (2):

3. The organic EL multi-color light-emitting device according to claim 2, wherein, in the formula (1), when Ar¹ and Ar², Ar¹ and Ar³ and Ar² and Ar³ are not bonded with each other, at least one of Ar¹ to Ar³ is a substituent represented by the formula (a).

4. The organic EL multi-color light-emitting device according to claim 2, wherein at least one of Ar¹, Ar² and Ar³ in the formula (1) and at least one of Ar¹¹, Ar¹², Ar¹³ and Ar¹⁴ in the formula (2) is a substituent represented by the formula (a).

5. The organic EL multi-color light-emitting device according to claim 2, wherein the substituent represented by the formula (a) is a substituent represented by the following formula (a-1):

6. The organic EL multi-color light-emitting device according to claim 5, wherein the substituent represented by the formula (a-1) is a substituent represented by the following formula (a-2):

7. The organic EL multi-color light-emitting device according to claim 2, wherein at least one of Ar¹, Ar² and Ar³ in the formula (1) and at least one of Ar¹¹, Ar¹², Ar¹³ and Ar¹⁴ in the formula (2) is a substituent represented by the following formula (c):

—

Ar²¹—

Ar²²Ar²³)_p 

 

(c)

wherein Ar²¹ to Ar²³ are independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms; and

p is an integer of 0 to 2.

8. The organic EL multi-color light-emitting device according to claim 7, wherein the substituent represented by the formula (c) is a substituent represented by the following formula (c-1):

9. The organic EL multi-color light-emitting device according to claim 2, wherein at least one of Ar⁴ and Ar⁵ is a linkage group represented by the formula (d) or (e):

10. The organic EL multi-color light-emitting device according to claim 2, wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1):

11. The organic EL multi-color light-emitting device according to claim 2 wherein, when the aromatic hydrocarbon group having 6 to 25 ring carbon atoms of R¹ and R² and the aromatic heterocyclic group having 5 to 25 ring atoms have a substituent, the substituent is a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.

12. The organic EL multi-color light-emitting device according to claim 2, wherein the compound represented by the formula (2) is a compound represented by the following formula (f):

13. The organic EL multi-color light-emitting device according to claim 12, wherein the compound represented by the formula (f) is a compound represented by the following formula (f-1) or the following formula (f-2):

14. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer is in contact with the first organic layer and the second organic layer comprises the compound represented by the formula (C) or (D).

15. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer is in contact with the third organic layer, and the second organic layer comprises the compound represented by the formula (A) or (B).

16. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer is a single layer or a stack of a plurality of organic layers, and the second organic layer comprises two or more selected from the compounds (A) to (D).

17. The organic EL multi-color light-emitting device according to claim 16, wherein the second organic layer is a stack of a plurality of organic layers.

18. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer comprises a compound having a triplet energy of 2.55 eV or more.

19. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer is in contact with the first organic layer, and the second organic layer comprises a compound having a triplet energy of 2.65 eV or more.

20. The organic EL multi-color light-emitting device according to claim 1, wherein the first organic layer is a red, yellow or green phosphorescent emitting layer and the third organic layer of the second light-emitting element is a blue fluorescent emitting layer.

21. The organic EL multi-color light-emitting device according to claim 1, wherein the first organic layer is formed by coating and the third organic layer is formed by deposition.

22. The organic EL multi-color light-emitting device according to claim 1, wherein a hole-injecting and/or hole-transporting layer formed by coating is provided on the anode side of the second organic layer of the second light-emitting element.

23. The organic EL multi-color light-emitting device according to claim 1, wherein the compounds (A) to (D) are a compound represented by the following formula (1) or (2):

24. The organic EL multi-color light-emitting device according to claim 1, wherein the compounds (A) to (D) are a compound represented by the following formula (1) or (2):

25. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer of the first light-emitting element and the second organic layer of the second light-emitting element each independently comprise a compound represented by the following formula (1) or (2):

26. The organic EL multi-color light-emitting device according to claim 1, wherein the first light-emitting element emits blue light, the second light-emitting element emits red or green light, and the first light-emitting element and the second light-emitting element emit different color lights from each other.

27. The organic EL multi-color light-emitting device according to claim 1, wherein the first light-emitting element is a green-emitting element, a red-emitting element or a yellow-emitting element, and the second light-emitting element is a blue-emitting element.

28. The organic EL multi-color light-emitting device according to claim 1, wherein the second organic layer is capable of preventing emission of light from the third organic layer in the first light-emitting element.