Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-9708262-B2
Application number	US-201514814994-A
Country	US
Kind code	B2
Filing date	Jul 31, 2015
Priority date	Jan 25, 2010
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

The present invention relates to compounds of the formula (I) and to the use thereof in organic electronic devices, and to organic electronic devices which comprise compounds of the formula (I), preferably as hole-transport materials and/or as matrix materials, in particular in combination with a further matrix material.

First claim

The invention claimed is:

1. A compound of the formula (I)

where the following applies to the symbols and indices occurring:
Y is on each occurrence, identically or differently, a single bond or C(R 2 ) 2 , where at least one group Y which represents a single bond is present;
Ph is a phenyl group, which may be substituted by one or more radicals R 1 ;
Ar 1 is an aromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
R 1 , R 2 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, 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 may be substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups may be replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, where two or more radicals R 1 and/or R 2 may be linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , CR 4 ═C(R 4 ) 2 , CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , OH, 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 may be substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 4 , or a combination of these systems, where two or more radicals R 3 may be linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 4 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F; two or more identical or different substituents R 4 here may also be linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
n is on each occurrence, identically or differently, 0 or 1, where the sum of the values of n is equal to 1 or 2 and where, for n=0, a group R 1 is bonded instead of a group Y;
and where not more than one group R 1 which represents a group of the formula N(R 3 ) 2 , where R 3 is an aryl group, may be bonded to a single triarylamine group in formula (I).

2. The compound according to claim 1 , wherein the sum of the values of n is equal to 1.

3. The compound according to claim 1 , wherein precisely one group Y is a single bond and precisely one further group Y is C(R 2 ) 2 .

4. The compound according to claim 1 , wherein R 1 is selected on each occurrence, identically or differently, from H, D, F, CN, Si(R 3 ) 3 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 3 , where one or more adjacent or non-adjacent CH 2 groups may be replaced by —C≡C—, R 3 C═CR 3 , Si(R 3 ) 2 , C═O, C═NR 3 , NR 3 , O, S, COO or CONR 3 , or an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 .

5. The compound according to claim 1 , wherein R 2 is selected on each occurrence, identically or differently, from H, D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms or an aryl group having 6 to 18 carbon atoms, where the said groups may each be substituted by one or more groups R 3 .

6. The compound according to claim 1 , wherein at least one group R 2 which represents an aryl group having 6 to 10 carbon atoms which is substituted by one or more radicals R 3 must be present.

7. The compound according to claim 1 , wherein R 3 is selected on each occurrence, identically or differently, from H, D, F, CN, Si(R 4 ) 3 , N(R 4 ) 2 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 4 , where one or more adjacent or non-adjacent CH 2 groups may be replaced by —C≡C—, R 4 C═CR 4 , Si(R 4 ) 2 , C═O, C═NR 4 , NR 4 , O, S, COO or CONR 4 , or an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 .

8. The compound according to claim 1 , wherein R 4 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F.

9. The compound according to claim 1 , wherein Ar 1 conforms to a formula (Ar 1 -1)

where the bonds to the group Ph and to the nitrogen atom are represented by the dashed lines, and where the group may be substituted in all free positions by radicals R 1 as defined in claim 1 .

10. The compound according to claim 1 , wherein the group Ph conforms to one of the formulae (Ph-1) and (Ph-2):

where the bonds to the nitrogen atom and to the group Ar 1 are represented by the dashed lines, and the symbols # mark the position of the bond to a group Y, if present, and where the structures may be substituted in all free positions by radicals R 1 as defined in claim 1 .

11. The compound according to claim 1 , wherein the compound conforms to one of the following formulae (I-16) to (I-20):

where
L is C(R 2 ) 2 ; and
R 1 is as defined in claim 1 .

12. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer may be localised at any desired positions substituted by R 1 or R 2 in formula (I).

13. A formulation comprising at least one compound ac

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir H
• Pflumm Christof
• Brocke Constanze

Classifications

• H01L51/05

  Electricity · mapped topic

• C09B15/00

  Acridine dyes · CPC title

• C09B17/00

  Azine dyes · CPC title

• H01L51/0072

  Electricity · mapped topic

• C07D471/06 Primary

  Peri-condensed systems · CPC title