Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9653687-B2
Application number	US-201113879094-A
Country	US
Kind code	B2
Filing date	Sep 15, 2011
Priority date	Oct 14, 2010
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

The present invention relates to a mixture comprising a) a polymer which contains at least one L=X structural unit, b) a triplet emitter compound and c) a carbazole compound or a soluble neutral molecule. The invention furthermore relates to organic electroluminescent devices which contain the mixture according to the invention.

First claim

The invention claimed is:

1. A mixture comprising
a) a polymer comprising a main-chain which contains at least one L=X structural unit, and wherein the content of the at least one structural unit in the polymer is up to 80 mol %,
b) a triplet emitter compound and
c) a carbazole compound,

where the following applies to the symbols and indices used:
L is on each occurrence, identically or differently, C(R 1 ) 2 , PR 1 , P(R 1 ) 3 , S(R 1 ) 2 , or (R 1 ) 2 S(═O);
X is on each occurrence, identically or differently, O, S or NR 2 ;
R 1 is on each occurrence, identically or differently, H, D, F, CN, N(R 2 ) 2 , a straight-chain, branched or cyclic alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which is optionally substituted by R 3 or also unsubstituted, where one or more non-adjacent CH 2 groups is optionally replaced by
—R 4 C═CR 4 —, —C═C—, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , —O—, —S—, —NR 4 or —CONR 4 — and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 1 to 60 C atoms, which is optionally substituted by one or more radicals R 3 , where two or more substituents R 1 , together with the atoms to which they are bonded, may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where at least one group R 1 has a bond to a further structural unit of the polymer;

R 2 is on each occurrence, identically or differently, a straight-chain, branched or cyclic alkyl or alkoxy group having 1 to 22 C atoms, in which, in addition, one or more non-adjacent C atoms is optionally replaced by
—R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , —NR 4 —, —O—, —S—, —CO—O—,
—O—CO—O—, where, in addition, one or more H atoms is optionally replaced by fluorine, an aryl, heteroaryl or aryloxy group having 1 to 40 C atoms, which may also be substituted by one or more radicals R 3 , or OH or N(R 3 ) 2 ;

R 3 is on each occurrence, identically or differently, R 4 or CN, B(R 4 ) 2 or Si(R 4 ) 3 ;
R 4 is on each occurrence, identically or differently, H, D or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms,
and wherein the triplet emitter compound contains at least one atom having an atomic number greater than 56 and less than 80.

2. The mixture according to claim 1 , wherein the structural unit L=X of the polymer is a structural unit of the formula (1)

where the following applies to the symbols used:
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more groups R 5 ;
R 5 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 6 ═CR 6 Ar 1 , CN, NO 2 , Si(R 6 ) 3 , B(OR 6 ) 2 , B(R 6 ) 2 , B(N(R 6 ) 2 ) 2 , OSO 2 R 6 , 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 6 , where one or more non-adjacent CH 2 groups is optionally replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 6 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 6 , or a combination of these systems; two or more adjacent substituents R 5 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 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 5 ;
R 6 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by F; two or more adjacent substituents R 6 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
where at least one radical R 5 is a covalent bond to a further structural unit of the polymer.

3. The mixture according to claim 1 , wherein the polymer contains at least one further structural unit which is different from the structural unit L=X, selected from a substituted or unsubstituted cis- or trans-indenofluorene structural unit or a structural unit containing two aromatic groups which are connected to one another via a linear C 1 -C 10 -alkyl group.

4. The mixture according to claim 1 , wherein the carbazole compound is a compound of the formula (2)

where the following applies to the symbols and indices used:
Ar is on each occurrence an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 7 ;
R 7 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(Ar 2 ) 2 , CN, NO 2 , Si(R 8 ) 3 , B(OR 8 ) 2 , C(═O)Ar 2 , P(═O)(Ar 2 ) 2 , S(═O)Ar 2 , S(═O) 2 Ar 2 , —CR 8 ═CR 8 (Ar 2 ), OSO 2 R 8 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 8 , where one or more non-adjacent CH 2 groups is optionally replaced by R 8 C═CR 8 , C≡C, Si(R 8 ) 2 , Ge(R 8 ) 2 , Sn(R 8 ) 2 , C═O, C═S, C═Se, C═NR 8 , P(═O)(R 8 ), SO, SO 2 , NR 8 , O, S or CONR 8 and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 8 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 8 , or a combination of these systems; two or more substituents R here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 7 is on each occurrence, identically or differently, R, a group Ar 2 or F;
Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 8 ;
R 8 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R; two or more substituents R 8 here may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
n is on each occurrence, identically or differently, 0, 1, 2, 3 or 4;
p is on each occurrence, identically or differently, 0, 1, 2, 3 or 4; and
q is 1, 2, 3, 4 or 5.

5. The mixture according to claim 3 , wherein the carbazole compound is a compound of the formula (2)

Assignees

• Ludemann Aurélie
• Anémian Rémi Manouk
• Heun Susanne
• Rapp Almut
• Merck Patent Gmbh

Inventors

• Ludemann Aurélie
• Anémian Rémi Manouk
• Heun Susanne
• Rapp Almut

Classifications

• C08G2261/411

  Suzuki reactions · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C08G2261/3424

  non-conjugated, e.g. paracyclophanes or xylenes · CPC title

• C08G2261/126

  block · CPC title