Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-8951647-B2
Application number	US-99979209-A
Country	US
Kind code	B2
Filing date	Jul 8, 2009
Priority date	Aug 8, 2008
Publication date	Feb 10, 2015
Grant date	Feb 10, 2015

Abstract

The present invention relates to organic electroluminescent devices which comprise fluorene derivatives and spirobifluorene derivatives as matrix material for phosphorescent emitters.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising, in at least one emitting layer,
(A) at least one phosphorescent compound and
(B) at least one compound of the formula (1) or formula (2):

where the following applies to the symbols and indices used:
Ar is on each occurrence, identically or differently, a heteroaryl group selected from the group consisting of triazine, pyrazine, pyridazine, pyridine, pyrazole, imidazole, oxazole and thiazole, each of which may be substituted by one or more groups R 1 ;
X is on each occurrence, identically or differently, a group of the formula (3), where the dashed bond in each case indicates the bonding to the two benzene rings:

or X is on each occurrence, identically or differently, a divalent bridge selected from B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R′), P(R 1 ) and P(═O)R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 2 ═CR 2 Ar 1 , 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 or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more, non-adjacent CH 2 groups is 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 where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems; two or more adjacent substituents R 1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two radicals Ar 1 here which are bonded to the same nitrogen, phosphorus or boron atom are optionally linked to one another by a single bond or a bridge selected from the group consisting of B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(O)R 2 ;
R 2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by D or F; two or more adjacent substituents R 2 here optionally form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
n is 0 or 1;
m is 0, 1, 2 or 3;
o is 0, 1, 2, 3 or 4 if n=0 and is 0, 1, 2 or 3 if n=1.

2. The organic electroluminescent device according to claim 1 , wherein the compound of the formula (1) or formula (2) is a fluorene derivative of the formula (4) or formula (5) or a spirobifluorene derivative of the formula (6) or formula (7):

where the symbols and indices used have the same meanings as described in claim 1 .

3. The organic electroluminescent device according to claim 2 , wherein the monovalent group Ar is selected from the groups of the formulae (8) to (20), where the dashed bond in each case indicates the bonding of the group to the fluorene or spirobifluorene or to the corresponding heterocyclic derivative, and R 1 has the same meaning as described in claim 2 , and in that the divalent group Ar in compounds of the formulae (2), (5) and (7) is selected from the groups of the formulae (21) to (28), where the dashed bonds in each case indicate the bonding of the group to the fluorene or spirobifluorene or to the corresponding heterocyclic derivative, and R 1 has the same meaning as described in claim 2 :

4. The organic electroluminescent device according to claim 3 , wherein the radical R 1 which is bonded to the groups of the formulae (8) to (28) stands, identically or differently on each occurrence, for H or D, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R 2 , Where one or more H atoms is optionally replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or a combination of these systems.

5. The organic electroluminescent device according to claim 2 , wherein the compound of the formula (1), (2) or (4) to (5) is selected from compounds of the formulae (29) to (32):

where the symbols and indices have the same meaning as described in claim 2 , and where, for n=0, a substituent R 1 may also be bonded in the corresponding position.

6. The organic electroluminescent device according to claim 1 , wherein the index m=0 and in that the sum of the indices n+o=0 or 1 on each benzene ring.

7. The organic electroluminescent device according to claim 1 , wherein the compound of the formula (1) or formula (2) is selected from compounds of the formulae (33) to (36):

where the symbols and indices used have the meanings mentioned in claim 1 , and furthermore n+o=0 or 1 on each benzene ring and where, for n=0 and o=1, the radical R 1 may be bonded to any desired free site on the benzene ring.

8. The organic electroluminescent device according to claim 7 , wherein the compounds of the formula (35) are selected from compounds of the formulae (37), (38) and (39):

where the symbols used have the meanings mentioned above and o stands, identically or differently on each occurrence, for 0 or 1.

9. The organic electroluminescent device according to claim 1 , wherein the phosphorescent compound is a compound which contains copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium.

10. The organic electroluminescent device according to claim 1 , wherein the phosphorescent compound is a compound which contains iridium or platinum.

11. The organic electroluminescent device according to claim 10 , wherein the phosphorescent compound is selected from compounds of the formulae (40) to (43):

where R 1 has the same meaning as described in claim 10 , and the following applies

Assignees

• Parham Amir Hossain
• Kaiser Joachim
• Gerhard Anja
• Kroeber Jonas Valentin
• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Kaiser Joachim
• Gerhard Anja
• Kroeber Jonas Valentin

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09B57/00 Primary

  Other synthetic dyes of known constitution · CPC title

• Y10S428/917

  Electroluminescent · CPC title

• H01L51/0067 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic