Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-10227528-B2
Application number	US-201314654708-A
Country	US
Kind code	B2
Filing date	Nov 27, 2013
Priority date	Dec 21, 2012
Publication date	Mar 12, 2019
Grant date	Mar 12, 2019

Abstract

The present invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, comprising these compounds.

First claim

The invention claimed is:

1. A compound of the formula (1) or formula (1A),

where the following applies to the symbols and indices used:
Y is on each occurrence, identically or differently, CR 1 or N, with the proviso that at least one group Y stands for N;
X is on each occurrence, identically or differently, CR 1 or N; or two adjacent X stand for S, O or NR 1 , so that a five-membered ring forms; or two adjacent X stand for a group of the following formula (2), (3) or (4),

where ^ indicates the corresponding adjacent groups X in the formula (1);
V is on each occurrence, identically or differently, C(R 1 ) 2 , NR 1 , O, S, BR 1 , Si(R 1 ) 2 or C═O;
Z is on each occurrence, identically or differently, CR 1 or N;
Ar 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 1 ;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, N(Ar 1 ) 2 , a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl 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 or O and where one or more H atoms is optionally replaced by D or F, or an aromatic ring system having 6 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; wherein the aromatic ring system is selected from benzene, ortho-, meta-para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta-, para- or branched quaterphenyl, 1-, 2- or 3-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, phenanthrene, or combinations of two or three of these groups, each of which may be substituted by one or more radicals R 1 ; two adjacent substituents R here may form a monocyclic or polycyclic, aliphatic or aromatic ring system, which is optionally substituted by one or more radicals R 2 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 2 ) 2 , C(═O)Ar 1 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 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 , C═O, C═S, 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 , 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 2 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two adjacent substituents R 1 here may optionally form a monocyclic or polycyclic, or aliphatic ring system, which is optionally substituted by one or more radicals R 2 ;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 2 ; two radicals Ar 1 here which are bonded to the same N atom or P atom may also be bridged to one another by a single bond or a bridge selected from N(R 2 ), C(R 2 ) 2 , O or S;
R 2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R 2 may form a mono- or polycyclic, aliphatic ring system with one another;
m and n are on each occurrence, identically or differently, 0 or 1, with the proviso that m+n≥1;
p is on each occurrence, identically or differently, 0, 1, 2, 3 or 4;
q is 0, 1 or 2.

2. The compound according to claim 1 , wherein the X stands, identically or differently on each occurrence, for the CR 1 or the N, where a maximum of one group X per ring stands for the N; or the two adjacent groups X stand for a group of the formula (2) or (3), where the Z stands, identically or differently on each occurrence, for the CR 1 and the V stands, identically or differently on each occurrence, for the NR 1 , the C(R 1 ) 2 , the O or the S.

3. The compound according to claim 1 , wherein the compound is selected from the compounds of the formulae (5) to (12),

where the symbols and indices used have the meanings given in claim 1 , and the V stands for the NR 1 , the C(R 1 ) 2 , the O or the S.

4. The compound according to claim 1 , wherein the compound is selected from the structures of the formulae (5a) to (12a),

where the symbols and indices used have the meanings given in claim 1 .

5. The compound according to claim 1 , wherein the R is selected, identically or differently on each occurrence, from the group consisting of H, F, CN, N(Ar 1 ) 2 , a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic ring system having 6 to 30 aromatic ring atoms, where the aromatic ring system does not contain heteroaryl groups, which is optionally substituted by one or more non-aromatic radicals R 2 , and wherein the aromatic ring system is selected from benzene, ortho-, meta-para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta-, para- or branched quaterphenyl, 1-, 2- or 3-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, phenanthrene, or combinations of two or three of these groups, each of which may be substituted by one or more radicals R 1 and in that the R 1 is selected, identically or differently on each occurrence, from the group consisting of H, D, F, Br, CN, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , 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 or an alkenyl or alkynyl group having 2 to 10 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 O and where one or more H atoms is optionally replaced by D or F, 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 .

6. The compound according to claim 1 , wherein the Ar is selected from aromatic or heteroaromatic ring systems having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , each of which is optionally substituted by one

Assignees

• Merck Patent Gmbh

Inventors

• Jatsch Anja
• Pflumm Christof
• Parham Amir Hossain
• Eberle Thomas
• Stoessel Philipp
• Kroeber Jonas Valentin
• Linge Rouven

Classifications

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D209/96 Primary

  Spiro-condensed ring systems · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title