Compounds and organic electronic devices

Patent metadata

Field	Value
Publication number	US-10944058-B2
Application number	US-201715833506-A
Country	US
Kind code	B2
Filing date	Dec 6, 2017
Priority date	Jul 23, 2012
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

Abstract

The present invention relates to certain fluorenes, to the use of the compounds in an electronic device, and to an electronic device comprising at least one of these compounds. The present invention furthermore relates to a process for the preparation of the compounds and to a formulation and composition comprising one or more of the compounds.

First claim

The invention claimed is:

1. A compound of the general formula (1)

where the following applies to the symbols and indices used:
R 1
is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 4 , CN, Si(R 4 ) 3 , NO 2 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl, alkoxy or thio-alkyl 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 4 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═S, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, P(═O)(R 4 ), —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 4 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , where the two radicals R 1 is optionally linked to one another and may form a ring, so that a spiro compound forms in position 9 of the fluorene, where spirobifluorenes are excluded;

R 2 and R 3
are on each occurrence, identically or differently, preferably identically, H, D, F, Cl, Br, I, C(═O)R 4 , CN, Si(R 4 ) 3 , NO 2 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , N(R 4 ) 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 4 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═S,
C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, P(═O)(R 4 ), —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 4 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , where two or more radicals R 2 or two or more radicals R 3 is optionally linked to one another and may form a ring;

R 4
is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 5 , CN, Si(R 5 ) 3 , NO 2 , P(═O)(R 5 ) 2 , S(═O)R 5 , S(═O) 2 R 5 , N(R 5 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thio-alkyl 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 5 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═S,
C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, P(═O)(R 5 ), —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 5 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 5 ;

R 5
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 5 may form a mono- or polycyclic, aliphatic ring system with one another;

q is 1, and
p and r are 0;

Z a 0 , Z c 0
are R 3 ;

Z b 1
is

B′
is an aryl group having 6 to 30 ring atoms or a mono- or bicyclic heteroaryl group having 5 to 30 ring atoms, each of which is optionally substituted by one or more radicals R 4 ;

Ar 1 is a compound of formula (77)-(93)

which is optionally substituted by one or more radicals R 6 ;
Ar 2 is a compound of formula (37), (38), (39) or (64)-(116)

which is optionally substituted by one or more radicals R 6 ;
R 6
is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 5 , CN, Si(R 5 ) 3 , NO 2 , P(═O)(R 5 ) 2 , S(═O)R 5 , S(═O) 2 R 5 , a straight-chain alkyl, alkoxy or thio-alkyl 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 5 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═S, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, P(═O)(R 5 ), —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 hetero-aromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 5 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 5 ;

with the proviso that Z a 1 , Z b 1 and Z c 1 in the compound of the formula (1) contain no fluorene or carbazole groups.

2. The device according to claim 1 , wherein
Ar 1 and Ar 2
are on each occurrence, identically or differently, an aromatic or heteroaromatic radical having 10 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 6 , which are identical to or different from one another, where the two groups Ar 1 or Ar 2 each contain at least two or more aromatic or heteroaromatic rings,
where two of the aromatic or heteroaromatic rings in Ar 1 and/or two of the aromatic or heteroaromatic rings in Ar 2 is in uncondensed form,
and where two of the aromatic or heteroaromatic rings in Ar 1 is unbridged and
where the compound of the formula (1) contains no condensed aromatic or heteroaromatic ring systems.

3. The compound according to claim 1

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C07D219/02 Primary

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

• C07D307/91

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/171

  Electron injection layers · CPC title