Materials for organic electroluminescence devices

Patent metadata

Field	Value
Publication number	US-9893292-B2
Application number	US-201414219793-A
Country	US
Kind code	B2
Filing date	Mar 19, 2014
Priority date	Jun 9, 2005
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

The present invention relates to novel materials which can be used in organic electronic devices, in particular electroluminescent devices, and are certain derivatives of fused aromatic systems.

First claim

The invention claimed is:

1. A mixture comprising at least one compound of the Formula (I) and one or more dopants;

wherein
Ar 1 is, identically or differently on each
occurrence, a fused aryl or heteroaryl group having at least 14 aromatic ring atoms optionally substituted by one or more R;
X is, identically or differently on each occurrence, a group of formula (2) or (3)

 wherein the dashed bond is a link from Ar 2 or Q to Ar 1 ;
Y is, identically or differently on each occurrence, X; an Ar 3 group; or an N(Ar 3 ) 2 group, wherein the two Ar 3 radicals are optionally bonded to one another by a single bond or via an O, S, N(R), or C(R) 2 group;
Ar 2 is, identically or differently on each occurrence, an aryl or heteroaryl group optionally substituted by one or more R and to which a group Q is bonded, with the proviso that either the group Q or an R other than H is bonded in the orthoposition to the Ar 1 —Ar 2 bond;
Ar 3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system optionally substituted by one or more R;
Q is, identically or differently on each occurrence, a linear, branched, or cyclic alkylene or alkylidene group which forms two bonds to Ar 2 or one bond to Ar 1 and one bond to Ar 2 and thereby defining a further ring system; wherein Q has up to 20 C atoms optionally substituted by R 1 , wherein one or more non-adjacent C atoms are optionally replaced by N—R 1 , O, S, O—OO—O, CO—O, —CR 1 ═CR 1 —, or—C≡C—, and one or more H atoms are optionally replaced by F, Cl, Br, I, or CN,
wherein Q is bonded to the ortho-position of Ar 2 , where said ortho-position is relative to the link between Ar 2 and Ar 1 ;

R is, identically or differently on each occurrence, H, F, Cl, Br, I, CN, a straight-chain alkyl or alkoxy chain having up to 40 C atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, wherein said straight-chain alkyl or alkoxy chain or said branched or cyclic alkyl or alkoxy group are optionally substituted by R 1 , wherein one or more non-adjacent C atoms are optionally replaced by N—R 1 , O, S, O—CO—O, CO—O, —CR 1 ═CR 1 —, or —C≡C—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R 1 , or a combination of two, three or four of these systems; and wherein two or more R here optionally define a further mono- or polycyclic, aliphatic, or aromatic ring system with one another;
R 1 is, identically or differently on each occurrence, H or a hydrocarbon radical having up to 20 C atoms, wherein said hydrocarbon radical is optionally aliphatic or aromatic or a combination of aliphatic and aromatic, and wherein one or more H atoms are optionally replaced by F;
m is, on each occurrence, 0 or 1;
p is, on each occurrence, 0, 1, or 2;
with the proviso that the following compound is excluded as a compound of formula (1):

2. The mixture of claim 1 , wherein said dopants are selected from the group consisting of aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrene-diamines, monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers, and arylamines.

3. The mixture of claim 2 , wherein Ar 1 is selected from the group consisting of anthracene, acridine, phenanthrene, phenanthroline, pyrene, naphthacene, chrysene, pentacene, phenanthroline, and perylene, each of which is optionally substituted by R.

4. The mixture of claim 1 , wherein Ar 1 contains three, four, five, or six aromatic or heteroaromatic units, which are in each case fused to one another via one or more common edges and are optionally substituted by R.

5. The mixture of claim 1 , wherein the compound of formula (1) is selected from the group consisting of structures of formula (7), (8), (9), (10), (11), and (12):

wherein the anthracene, phenanthrene, and pyrene units are optionally substituted by one or more R.

6. The mixture of claim 1 , wherein Ar 3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms optionally substituted by R.

7. The mixture of claim 1 , wherein Ar 2 , is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 16 aromatic ring atoms optionally substituted by R.

8. The mixture of claim 1 , wherein Q is a linear, branched, or cyclic alkylene chain having 2 to 15 C atoms optionally substituted by R 1 , wherein one or more non-adjacent C atoms are optionally replaced by N—R 1 , O, or S and one or more H atoms are optionally replaced by F or CN.

9. The mixture of claim 1 , wherein Q defines a 6- , 7-, or 8-membered ring system together with Ar 1 and Ar 2 or defines a 3-, 4-, 5-, 6-, 7-, or 8-membered ring system together with Ar 2 .

10. The mixture of claim 1 , wherein the structures of formula (2) are selected from the group consisting of the structures of formula (15), (16), (17), (18), (19), and (20):

wherein the phenyl, naphthyl, or anthryl unit are in each case optionally substituted by R and wherein the dashed bond is the link to the Ar 1 unit.

11. The mixture of claim 1 , wherein the structures of formula (2) are selected from the group consisting of the structures of formula (21), (22), (23), and (24):

wherein
Z is CR 2 , O, S, NR, PR, P(═O)R, SiR 2 , or CR 2 —CR 2 ;
n is 1, 2, or 3; and
the dashed bond is the link to the Ar 1 unit.

12. The mixture of claim 1 , wherein Q defines a ring system with Ar 2 .

13. The mixture of claim 1 , wherein Q contains no benzylic protons or a bridgehead C atom is linked directly to Ar 2 .

14. The mixture of claim 1 , wherein p is 0 or 1.

15. The mixture of claim 1 , wherein said compounds of the formula (I) are selected from structures (1) to (98):

Assignees

• Merck Patent Gmbh

Inventors

• Heil Holger
• Buesing Arne
• Stoessel Philipp
• Vestweber Horst

Classifications

• C07D237/26

  condensed with carbocyclic rings or ring systems · CPC title

• C07D237/08

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• H01L51/0054

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0058

  Electricity · mapped topic