Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-10374168-B2
Application number	US-201515303390-A
Country	US
Kind code	B2
Filing date	Mar 19, 2015
Priority date	Apr 14, 2014
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

The present application relates to heterospirobifluorene compounds, to a process for the preparation thereof, and to electronic devices, in particular organic electroluminescent devices, comprising the heterospirobifluorene derivatives.

First claim

The invention claimed is:

1. A compound of the formula (I)

where the following applies to the symbols and indices occurring:
A is C;
Y is N;
X is on each occurrence, identically or differently, CR 1 or N;
Ar 1 , Ar 2 are on each occurrence, identically or differently, selected from the formula (Ar-2) to (Ar-15) and (Ar-18) to (Ar-66)

Ar 3 , Ar 4 , Ar 5 , Ar 6 on each occurrence, identically or differently, conform to formula (Ar-1),

 which is optionally substituted by one or more radicals R 2 on the free positions, and where the bond denoted by * represents the bonding position of the respective group;
R 1 , R 2 are selected on each occurrence, identically or differently, from H, D, F, C(═O)R 3 , CF 3 , OCF 3 , CN, Si(R 3 ) 3 , N(R 3 ) 2 , P(═O)(R 3 ) 2 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 1 or R 2 is optionally linked to one another and may form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R 3 ; and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 ;
R 3 is selected on each occurrence, identically or differently, from H, D, F, C(═O)R 4 , CF 3 , OCF 3 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 3 is optionally linked to one another and may form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R 4 ; and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO or SO 2 ;
R 4 is selected on each occurrence, identically or differently, from H, D, F, CN, alkyl groups having 1 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 4 is optionally linked to one another and may form a ring; and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems is optionally substituted by F or CN;
a, b, c, d are on each occurrence, identically or differently, 0 or 1; and
wherein at least one of the indices a, b, c and d is equal to 1.

2. An oligomer, polymer or dendrimer containing one or more compounds of the formula (I)

where the following applies to the symbols and indices occurring:
A is C or Si;
Y is on each occurrence, identically or differently, N or P;
X is on each occurrence, identically or differently, CR 1 or N;
Ar 1 , Ar 2 are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
Ar 3 , Ar 4 , Ar 5 , Ar 6 are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
R 1 , R 2 are selected on each occurrence, identically or differently, from H, D, F, C(═O)R 3 , CF 3 , OCF 3 , CN, Si(R 3 ) 3 , N(R 3 ) 2 , P(═O)(R 3 ) 2 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 1 or R 2 is optionally linked to one another and may form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems may each be substituted by one or more radicals R 3 ; and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 ;
R 3 is selected on each occurrence, identically or differently, from H, D, F, C(═O)R 4 , CF 3 , OCF 3 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40

Assignees

• Merck Patent Gmbh

Inventors

• Pfister Jochen
• Voges Frank
• Montenegro Elvira
• Mujica-Fernaud Teresa

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/185

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

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title