Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-11649249-B2
Application number	US-201816606784-A
Country	US
Kind code	B2
Filing date	Apr 24, 2018
Priority date	Apr 25, 2017
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

The present application relates to bridged triarylamines conforming to a defined formula. These compounds are suitable for use in electronic devices. The present application further relates to processes for preparing the compounds, and to electronic devices comprising the compounds.

First claim

The invention claimed is:

1. A compound of formula (I)

where the variables that occur are as follows:
Y is the same or different at each instance and is selected from a single bond, O and S, where there is at least one Y group selected from O and S;
Z 1 is the same or different at each instance and is CR 1 , N or C, where a Z 1 group is C in the specific case when a Y group is bonded to it;
Ar 1 is the same or different at each instance and is an aromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted by one or more R 2 radicals;
Cbz is a divalent group of the formula (Cbz)

substituted at each of its unoccupied positions by an R 3 radical, where one of the two bonds of the divalent group to the rest of the compound is the dotted bond on the nitrogen atom of the formula (Cbz),
where the second of these two bonds may be at any unoccupied position in the group, and where
Z 2 is the same or different at each instance and is selected from C and N;
Ar 2 is selected from the formulae

where the variables that occur are defined as follows:
V is the same or different at each instance and is N or CR 4 , where at least one V group in each of formulae (Ar 2 -A), (Ar 2 -D) and (Ar 2 -E) is N;
W is the same or different at each instance and is N or CR 4 ;
U is NR 4 ;
where at least one group selected from W and V groups in formula (Ar 2 —B) is N; and
where one R 4 group per formula is replaced by the bond to the Ar 1 group or Cbz;
R 1 , R 2 , R 4 are the same or different at each instance and are selected from H, D, F, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 5 , S(═O) 2 R 5 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R 1 or R 2 or R 3 or R 4 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned may each be substituted by one or more R 5 radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO, SO 2 ;
R 3 are the same or different at each instance and are selected from H, D, F, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 5 , S(═O) 2 R 5 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; where two or more or R 3 or R 4 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR, P(═O)(R 5 ), —O—, —S—, SO, SO 2 ;
R 5 is the same or different at each instance and is selected from H, D, F, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , S(═OR 6 , S(═O)R 6 , S(═O) 2 R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R 5 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned may each be substituted by one or more R 6 radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may 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 the same or different at each instance and is selected from H, D, F, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon 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 R 6 radicals may be joined to one another and may form a ring; and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by F or CN;
i is the same or different at each instance and is 0 or 1, where at least two indices i in formula (I) are 1, and where the Y group in question is absent when the corresponding index i=0;
n is 0, 1, 2, 3 or 4; and
m is 0, 1, 2, 3 or 4.

2. The compound as claimed in claim 1 , wherein the Cbz group is the same or different at each instance and is selected from carbazole, azacarbazole, benzocarbazole, dibenzocarbazole, indenocarbazole, indolocarbazole, carbazole fused to benzofuran and carbazole fused to benzothiophene, where the groups mentioned may each be substituted by one or more R 3 radicals.

3. The compound as claimed in claim 1 , wherein the Cbz group is selected from the formulae

where:
T is C(R 3 ) 2 , O, S or NR 3 ;
where the dotted bonds represent the bonds to the rest of the compound, and
where the groups in the abovementioned formulae may each be substituted by an R 3 radical at any position shown as unsubstituted.

4. The compound as claimed in claim 1 , wherein Y is the same or different at each instance and is selected from O and S.

5. The compound as claimed in claim 1 , wherein Z 1 is CR 1 or C, where a Z 1 group is C when a Y group is bonded thereto.

6. The compound as claimed in claim 1 , wherein Ar 1 is the same or different at each instance and is a divalent group derived from the base skeletons of benzene, biphenyl, terphenyl, naphthalene, and fluorene, where the divalent group may be substituted by one or more R 2 radicals.

7. The compound as claimed in claim 1 , wherein R 1 , R 2 , and R 4 are the same or different at each instance and are selected from H, D, F, CN, Si(R 5 ) 3 , N(R 5 ) 2 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl or alkoxy groups mentioned, the aromatic ring

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir
• Kroeber Jonas
• Joosten Dominik
• Ludemann Aurélie
• Grossmann Tobias

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K85/6574

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

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title