Compounds and organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9595681-B2
Application number	US-201314416749-A
Country	US
Kind code	B2
Filing date	Jun 27, 2013
Priority date	Jul 23, 2012
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

The present invention concerns particular fluorenes, the use of the compound in an electronic device, and an electronic device containing at least one of these compounds. The present invention further concerns a method for producing the compound and a formulation and composition containing one or more of the compounds.

First claim

The invention claimed is:

1. An electroluminescent device comprising at least one compound of the general formula (2)

where the following applies to the symbols and indices used:
p, q, r, s
are 0 or 1, where p+q+r+s=1;

Z a 0 , Z b 0 , Z c 0 , Z d 0
are, identically or differently on each occurrence, equal to R 4

Z a 1 , Z b 1 , Z c 1 , Z d 1 are equal to

B
is a single bond, a divalent aryl group having 6 to 30 ring atoms or a divalent heteroaryl group having 5 to 30 ring atoms, each of which is optionally substituted by one or more radicals R 6 , where, if B is a single bond, the nitrogen atom is bonded directly to the fluorene;
Ar 1 and Ar 2 are selected, identically or differently on each occurrence, from the following groups of the formulae (42) to (107), (119)-(121) and (123)-(142)

where the dashed line denotes the linking position to the nitrogen atom;

R 2 , R 4 , and R 5
are H, D, F, Cl, Br, I, C(═O )R 6 , CN, Si(R 6 ) 3 , NO 2 , N(R 6 ) 2 , P(═O )(R 6 ) 2 , S(═O )R 6 , S(═O ) 2 R 6 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 6 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 6 C═CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═S, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, P(═O)(R 6 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 6 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 6 , or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 6 ;

R 1
is H, D, F, Cl, Br, I, C(═O)R 6 , CN, Si(R 6 ) 3 , NO 2 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , S(═O)R 6 , S(═O) 2 R 6 , a straight-chain alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkoxy or thioalkyl group having 3 to 20 C atoms or an alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 6 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 6 C═CR 6 , —C≡C—, Si(R 6 ) 2 , C═O, C═S, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, P(═O)(R 6 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 6 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 6 , or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 6 , where the radicals R 1 and R 2 cannot be identical and the radicals R 3 to R 5 may on each occurrence be identical or different, but is optionally identical to either R 1 or to R 2 ;
R 3 is H;

R 6
is on each occurrence, identically or differently, H, D, F, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , NO 2 , P(═O)(R 7 ) 2 , S(═O)R 7 , S(═O) 2 R 7 , N(R 7 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 7 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═S, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, P(═O)(R 7 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , 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 7 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 7 , where two or more adjacent substituents R 6 may form a mono- or polycyclic ring system with one another;

R 7
is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 C atoms, in which one or more H atoms is optionally replaced by D or F, where two or more adjacent substituents R 7 may form a mono- or polycyclic ring system with one another, and
wherein the compound of formula (2) is a monoamine compound.

2. The device according to claim 1 , wherein p=1 or r=1.

3. The device according to claim 1 , wherein the compound has the general formula (3)

where the symbols and indices indicated are defined as indicated in claim 1 .

4. The device according to claim 1 , wherein the compound has the general formula (4)

where the symbols and indices indicated are defined as indicated in claim 1 .

5. The device according to claim 1 , wherein the compound has the general formula (5)

where the symbols and indices indicated are defined as indicated in claim 1 .

6. The device according to claim 1 , wherein the compound has the general formula (6)

where the symbols and indices indicated are defined as indicated in claim 1 .

7. The device according to claim 1 , wherein B is a single bond or a phenylene, biphenylene, terphenylene, naphthylene, pyridinylene, pyrimidinylene, pyrazin-ylene, pyrida

Assignees

• Merck Patent Gmbh

Inventors

• Mujica-Fernaud Teresa
• Montenegro Elvira
• Parham Amir Hossain
• Buesing Arne
• Voges Frank

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07C209/10

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title