Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-12069950-B2
Application number	US-201917415980-A
Country	US
Kind code	B2
Filing date	Dec 17, 2019
Priority date	Dec 20, 2018
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

The present application concerns compounds for use in electronic devices, processes for preparing the compounds, and electronic devices comprising the compounds.

First claim

The invention claimed is:

1. A compound of formula (I)

where the following applies to the variable groups:
Z is C, if a group —[Ar 2 ] n -A is bonded to it; and Z is selected, identically or differently at each occurrence, from CR 1 and N, if no group —[Ar 2 ] n -A is bonded to it;
Y is C, if a group Ar 1 is bonded to it; and Y is selected, identically or differently on each occurrence, from CR 3 and N, if no group Ar 1 is bonded to it;
X is O or S;
Ar 1 is, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R 4 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R 4 ;
Ar 2 is, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R 5 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R 5 ;
A corresponds to the following formula

which is bonded via the dotted line;

Ar 3 and Ar 4 are, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R 5 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R 5 ;
T is a single bond or a divalent group selected from C(R 5 ) 2 , Si(R 5 ) 2 , N(R 5 ), O, and S;
k is 0 or 1, where k=0 means that T does not occur and the groups Ar 3 and Ar 4 are not connected;
R 1 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , 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 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 6 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 6 C═CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ;
R 2 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, Si(R 6 ) 3 , N(R 6 ) 2 , 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 the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 6 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 6 C═CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ;
R 3 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , 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 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 6 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 6 C═CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ;
R 4 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , 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 4 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 6 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 6 C—CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ;
R 5 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , 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 5 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 6 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 6 C═CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ;
R 6 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O)R 7 , S(═O) 2 R 7 , 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 6 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case be substituted by radicals R 7 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 ;
R 7 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, alkyl groups having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms, or heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more radicals selected from F and CN;
m is

Assignees

• Merck Patent Gmbh
• Merck Kgaa

Inventors

• Montenegro Elvira
• Mujica-Fernaud Teresa
• Maier-Flaig Florian
• Voges Frank

Classifications

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/6576 Primary

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title