ORGANIC LIGHT EMITTING DEVICE TO EMIT IN NEAR INFRARED

• US 20100231125A1
• Filed: 03/12/2009
• Published: 09/16/2010
• Est. Priority Date: 03/12/2009
• Status: Abandoned Application

• Current Assignee: Nitto Denko Corporation
• Original Assignee: Nitto Denko Corporation
• Inventors: LI, SHENG, MOCHIZUKI, AMANE
• Application Number:
  US12/403,265
• Publication Number:
  US 20100231125A1
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C09B 23/04 one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
• CPC Class Codes: C09B 57/10 Metal complexes of organic compounds not being dyes in uncomplexed form
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1055 with other heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/322 comprising boron

Abstract

Compositions and light-emitting devices related to compounds represented by Formula I are disclosed herein.

Claims

1. A composition comprising:

a host comprising at least one of a hole-transport material, an electron-transport material, and an ambipolar material; and

an emissive compound represented by Formula I;

2. The composition of claim 1 wherein R¹ is CF₃.

3. The composition of claim 1 wherein X¹ and X² are O.

4. The composition of claim 1 wherein Y¹ and Y² are F.

5. The composition of claim 1 wherein R⁴ and R⁵ are optionally substituted C_6-10 aryl or optionally substituted C_3-9 heteroaryl.

6. The composition of claim 1 wherein the emissive compound is further represented by Formula II:

7. The composition of claim 6 wherein the emissive compound is represented by Formula III:

8. The composition of claim 7 wherein the compound is present at a concentration of from about 0.1% (w/w) to about 10% (w/w).

9. The composition of claim 1 wherein the hole-transport material comprises at least one of an aromatic-substituted amine, a carbazole, polyvinylcarbazole, and N,N′

-bis(3-methylphenyl)N,N′

-diphenyl-[1,1′

-biphenyl]-4,4′

-diamine, poly(9-vinylcarbazole), polyfluorene, a polyfluorene copolymer, poly(9,9-di-n-octylfluorene-alt-benzothiadiazole), poly(paraphenylene), and poly[2-(5-cyano-5-methylhexyloxy)-1,4-phenylene].

10. The composition of claim 9 wherein the hole-transport material comprises poly(9-vinylcarbazole).

11. The composition of claim 1 wherein the electron-transport material comprises at least one of 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole, 1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole, 1,3-bis[2-(2,2′

-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]benzene, 3-phenyl-4-(1′

-naphthyl)-5-phenyl-1,2,4-triazole, 2,9-dimethyl-4,7-diphenyl-phenanthroline, aluminum tris(8-hydroxyquinolate), and 1,3,5-tris(2-N-phenylbenzimidazolyl)benzene.

12. The composition of claim 1 wherein the composition is a solid.

13. The composition of claim 1, wherein the composition is emissive.

14. The composition of claim 13 wherein the emissive composition is luminescent in an electric field, and the emissive composition has its maximum emission in the range of from about 720 nm to about 850 nm.

15. The composition of claim 1 wherein the composition comprises a liquid phase and is suitable for deposition onto a substrate.

16. The composition of claim 15 wherein the deposition onto a substrate comprises at least one of spraying, spin coating, drop casting, inkjet printing, and screen printing.

17. An organic light emitting diode device comprising:

an anode layer;

a cathode layer; and

a light-emitting layer positioned between, and electrically connected to, the anode layer and the cathode layer;

wherein the light-emitting layer comprises a composition of claim 1.

18. An organic light emitting diode device comprising:

an anode layer;

a cathode layer; and

a light-emitting layer positioned between, and electrically connected to, the anode layer and the cathode layer;

wherein the light-emitting layer comprises;

from about 1% (w/w) to about 10% (w/w) of 2,8-di(4-methoxyphenyl)-11-trifluoromethyl-difuro[2,3-b]-[3,2-g]-5,5-difluoro-5-bora-3a,4a-diaza-s-indacene;

poly(9-vinylcarbazole); and

2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole.

19. The device of claim 18 wherein the light-emitting layer comprises from about 50% (w/w) to about 80% (w/w) of poly(9-vinylcarbazole) and from about 20% (w/w) to about 50% (w/w) of the 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole.