Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12559510-B2
Application number	US-202017762123-A
Country	US
Kind code	B2
Filing date	Sep 21, 2020
Priority date	Sep 24, 2019
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

Abstract

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.

First claim

The invention claimed is:

1 . A compound of the formula (5) or (6),

where
R 40 , R 41 , R 43 , R 44 are at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 ,
R 42 is selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one more radicals R 32 ; and
R A stands on each occurrence, identically or differently, for F, CN, a straight-chain alkyl or alkoxy group having 1 to 40 C atoms or branched or cyclic alkyl or alkoxy groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F; or 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;
or
R 40 , R 41 , R 43 , R 44 are at each occurrence, identically or differently, selected from an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 ;
R 42 is selected from H, a straight-chain alkyl group having 1 to 10 carb atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 32 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 32 ; and
R A stands on each occurrence, identically or differently, for H, D, F, CN, a straight-chain alkyl or alkoxy group having 1 to 40 C atoms or branched or cyclic alkyl or alkoxy groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F; or 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;
Y is a single bond or a divalent bridge selected from —C(R Y ) 2 —, —C(R Y ) 2 —C(R Y ) 2 —, —O—, —S—, —S(═O) 2 — and —C(═O)—;
R Y stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , N(R) 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC═CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, P(═O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or 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, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; where two adjacent substituents R Y may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R′;
R 32 is on each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;
R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , Si(R′) 3 , B(OR′) 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R′, where in each case one or more non-adjacent CH 2 groups may be replaced by R′C═CR′, C≡C, Si(R′) 2 , Ge(R′) 2 , Sn(R′) 2 , C═O, C═S, C═Se, P(═O)(R′), SO, SO 2 , O, S or CONR′ and where one or more H atoms may be 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′, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R′, where two adjacent radicals R may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R′;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case also be substituted by one or more radicals R′;
R′ stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH 2 groups may be replaced by SO, SO 2 , O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms.

2 . The compound according to claim 1 , wherein R A stand on each occurrence, identically or differently,
for H, D, F, CN; or for a group of formula (RS-a),

wherein
R 22 , R 23 , R 24 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 , and where two of radicals R 22 , R 23 , R 24 or all radicals R 22 , R 23 , R 24 may be joined to form a (poly) cyclic alkyl group, which may be substituted by one or more radicals R 25 ;
R 25 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms;
with the proviso that at each occurrence at least one of radicals R 22 , R 23 and R 24 is other than H, with the proviso that at each occurrence all of radicals R 22 , R 23 and R 24 together have at least 4 carbon atoms and with the proviso that at each occurrence, if two of radicals R 22 , R 23 , R 24 are H, the remaining radical is not a straight-chain;
or for a group of formula (RS-b),

wherein
R 26 , R 27 , R 28 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R 25 as defined above, and where two of radicals R 26 , R 27 , R 28 or all radicals R 26 , R 27 , R 28 may be joined to form a (poly) cyclic alkyl group, which may be substituted by one or more radic

Assignees

• Merck Patent Gmbh

Inventors

• Stengel Ilona
• Lackner Aaron
• Rodriguez Lara-Isabel
• WALTER Charlotte
• Mekic Amel

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title