Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9356242-B2
Application number	US-201214349190-A
Country	US
Kind code	B2
Filing date	Sep 8, 2012
Priority date	Oct 6, 2011
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

An organic electroluminescent device that includes at least two phosphorescent emitting layers, where phosphorescent emitter layer 1 comprises a hole-conducting matrix material and two different phosphorescent emitters, and phosphorescent emitter layer 2 comprises an electron-conducting matrix material and a phosphorescent emitter.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising, in this sequence:
anode, phosphorescent emitter layer 1 , phosphorescent emitter layer 2 , which is in direct contact with said phosphorescent emitter layer 1 , a charge-generation layer, blue-emitting layer, and cathode, wherein said phosphorescent emitter layer 1 comprises a hole-conducting matrix material and two different phosphorescent emitters wherein one phosphorescent emitter is a shorter-wave phosphorescent emitter and one phosphorescent emitter is a longer-wave phosphorescent emitter, and said phosphorescent emitter layer 2 comprises an electron-conducting matrix material and a phosphorescent emitter, wherein the phosphorescent emitter of emitter layer 2 has the same emission maximum as the shorter-wave phosphorescent emitter of emitter layer 1 , wherein said device is a white-emitting, tandem organic electroluminescent device.

2. The organic electroluminescent device of claim 1 , wherein the phosphorescent emitter of emitter layer 2 is identical to the shorter-wave phosphorescent emitter of emitter layer 1 .

3. The organic electroluminescent device of claim 1 , wherein said phosphorescent emitter layer 1 is a yellow-, orange-, or red-emitting layer and phosphorescent emitter layer 2 is a green- or yellow-emitting layer.

4. The organic electroluminescent device of claim 1 , wherein said phosphorescent emitter layer 1 and said phosphorescent emitter layer 2 emit in total light having color coordinates of 0.45 ≦CIE x≦0.58.

5. The organic electroluminescent device of claim 1 , wherein said hole-conducting matrix material in said phosphorescent emitter layer 1 is a material which has an HOMO of ≧−5.5 eV.

6. The organic electroluminescent device of claim 1 , wherein the triplet energy T 1 of the hole-conducting matrix material in said phosphorescent emitter layer 1 is greater than that of the longer-wave emitter.

7. The organic electroluminescent device of claim 1 , wherein the electron-conducting matrix material in said phosphorescent emitter layer 2 is a material whose LUMO is in the range from −2.3 eV to −3.1 eV.

8. The organic electroluminescent device of claim 1 , wherein said phosphorescent emitter layer 2 comprises a mixture of an electron-conducting matrix material and at least one further matrix material.

9. The organic electroluminescent device of claim 1 , wherein the triplet energy T 1 of the electron-conducting matrix material in said phosphorescent emitter layer 2 is ≧2.5 eV.

10. The organic electroluminescent device of claim 1 , wherein the shorter-wave phosphorescent emitter is present in said phosphorescent emitter layer 1 in a concentration of 3 to 25% by vol. and the longer-wave phosphorescent emitter is present in emitter layer 1 in a concentration of 2 to 15% by vol., and wherein the phosphorescent emitter is present in said phosphorescent emitter layer 2 in a concentration of 2 to 20% by vol.

11. The organic electroluminescent device of claim 1 , wherein the electron-conducting matrix material in said phosphorescent emitter layer 2 is selected from the group consisting of compounds of the formulae (1) to (5),

wherein:
Ar 1 is, identically or differently on each occurrence, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 1 ;
Ar 2 is a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 1 ;
R 1 is, identically or differently on each occurrence, H; D; F; Cl; Br; I; CHO; C(═O)Ar 3 ; P(═O)(Ar 3 ) 2 ; S(═O)Ar 3 ; S(═O) 2 Ar 3 ; CR 2 ═CR 2 Ar 3 ; CN; NO 2 ; Si(R 2 ) 3 ; B(OR 2 ) 2 ; B(R 2 ) 2 ; B(N(R 2 ) 2 ) 2 ; OSO 2 R 2 ; a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms, a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , C═C , Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S, or CONR 2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 2 ; or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 2 ; or a combination of these systems; wherein two or more adjacent substituents R 1 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
Ar 3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R 2 ;
R 2 is, identically or differently on each occurrence, H, D, CN, or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F, wherein two or more adjacent substituents R 2 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
or wherein the electron-conducting matrix material in said phosphorescent emitter layer 2 is a compound of formula (21),

wherein:
Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more groups R 1 ; and
R 1 is, identically or differently on each occurrence, H; D; F; Cl; Br; I; CHO; C(═O)Ar 3 ; P(═O)(Ar 3 ) 2 ; S(═O)Ar 3 ; S(═O) 2 Ar 3 ; CR 2 ═CR 2 Ar 3 ; CN; NO 2 ; Si(R 2 ) 3 ; B(OR 2 ) 2 ; B(R 2 ) 2 ; B(N(R 2 ) 2 ) 2 ; OSO 2 R 2 ; a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms, a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , C≡C , Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S, or CONR 2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 ; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 2 ; or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 2 ; or a combination of these systems; wherein two or more adjacent substituents R 1 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system.

12. The organic electroluminescent device of claim 1 , wherein the hole-conducting matrix material in said phosphorescent emitter layer 1 is selected from the group consisting of the compounds of formulae (26) to (32),

wherein:
Ar 4 is, identically or differently on each occurrence, a divalent, trivalent or tetravalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optio

Assignees

• Kaiser Joachim
• Boehm Edgar
• Merck Patent Gmbh

Inventors

• Kaiser Joachim
• Boehm Edgar

Classifications

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0072

  Electricity · mapped topic

• H01L51/5206

  Electricity · mapped topic

• H01L51/005

  Electricity · mapped topic