Organic molecules for use in optoelectronic components

Patent metadata

Field	Value
Publication number	US-10669473-B2
Application number	US-201615544557-A
Country	US
Kind code	B2
Filing date	Jan 20, 2016
Priority date	Jan 20, 2015
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

The invention relates to organic molecules having a structure of formula 1

AF1-(Separator) m -AF2   Formula 1

wherein:

m is 0 or 1;

AF1 is a first chemical entity, having a conjugated system, in particular at least six conjugated electrons (e.g., in the form of at least one aromatic system);

AF2 is a second chemical entity, having a conjugated system, in particular at least six conjugated π electrons (e.g., in the form of at least one aromatic system);

with AF1≠AF2;

wherein AF1 has a structure of formula 2-1:

wherein

FG is selected from the group consisting of CR** 2 F, CF 3 , CF 2 R**, SF 5 , N—(CF 3 ) 1 , N—(CF 3 ) 2 , O—CF 3 , S—CF 3 and CF 2 CO 2 R*;

n=1 to 5;

o=1 to 5;

n+o=5;

p=0 or 1;

R′=linking point on the separator, linking point on the chemical entity AF2 or a radical R*;

wherein one R′ represents a linking point on the separator or on the chemical entity AF2.

First claim

The invention claimed is:

1. An organic molecule, comprising a structure of formula 1:
AF1-(Separator) m -AF2   Formula 1

wherein:
m is 0 or 1;
AF1 is a first chemical entity, comprising a conjugated system;
AF2 is a second chemical entity, comprising a conjugated system;
AF1≠AF2;
wherein AF1 comprises a structure of formula 2-2:

wherein
FG is selected from the group consisting of CF 3 , SF 5 , NH—(CF 3 ) 1 , N—(CF 3 ) 2 , O—CF 3 , S—CF 3 and a group E*, which is an aryl or heteroaryl group with 6 to 18 aromatic ring atoms, which may be substituted with one or more radicals R 8 , and which as a constituent of the aromatic ring contains one or more groups V*, wherein the groups V* in each instance are selected to be the same or different, from ═C(F)— and ═C(CF 3 )—;
#=linking point on the separator or linking point on the chemical entity AF2; and wherein AF2 comprises a structure of formula 4:

wherein
p is 0 or 1;
t=4−2p;
X is CR** 2 , NR**, oxygen, sulfur or a direct bond, wherein maximally two place holders X are simultaneously a direct bond, wherein these are not constituents of the same ring;
R*** is R** or is selected from the following entities, wherein maximally two of the radicals R*** simultaneously are equal to one of the following entities:

R** in each instance, independently of one another, is a radical R* or marks a linking point to a separator S or the chemical entity AF1 wherein exactly one R** is a linking point to a separator S or to the chemical entity AF1;
and wherein the separator S comprises a structure of formula 4S

wherein
# marks the linking point for the chemical entities AF1 and AF2;
p=0 or 1;
q=0 or 1;
and wherein p≠q;
Separator is a chemical entity that links AF1 and AF2 and wherein the separator is linked to the conjugated system of AF1 and to the conjugated system of AF2;
and wherein the following is applicable for formula 1, 2-2, and formula 4:
R* in each instance, independently of one another, is selected from the group consisting of H, deuterium, phenyl, naphthyl, —CN, —NO 2 , C(═O)OH, C(═O)OR 3 , C(═O)N(R 3 ) 2 , C(═O)SR 3 , C(═S)SR 3 , Si(R 4 ) 3 , B(OR 5 ) 2 , B(N(R 6 ) 2 ) 2 , C(═O)R 3 , P(═O)(R 7 ) 2 , As(═O)(R 7 ) 2 , P(═S)(R 7 ) 2 , As(═S)(R 7 ) 2 , S(═O)R 3 , S═NR 3 , S(═O)NR 3 , S(═O) 2 NR 3 , S(═O) 2 R 3 , O—S(═O) 2 R 3 , SF 5 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a linear alkenyl or alkynyl group with 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C atoms, which in each case may be substituted with one or more radicals R 9 , wherein one or more adjacent CH 2 groups may be replaced by —R 9 C═CR 9 —, —C≡C—, or one adjacent CH 2 -group by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 , —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, —C(═O)N(R 3 )—, —P(═O)(R 7 )—, —As(═O)(R 7 )—, —P(═S)(R 7 ), —As(═S)(R 7 )—, —S(═O)—, —S(═O) 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 ; two or more of these substituents R* may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system;
R 2 in each instance, independently of one another, is selected from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 , C(═O)OR 3 , Si(R 4 ) 3 , C(═O)R 3 , P(═O)(R 7 ) 2 , As(═O)(R 7 ) 2 P(═S)(R 7 ) 2 , As(═S)(R 7 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a linear alkenyl or alkynyl group with 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein one or more adjacent CH 2 groups may be substituted with —R 9 C═CR 9 —, —C≡C— or one adjacent CH 2 -group with —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 , —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, —C(═O)N(R 3 )—, —P(═O)(R 7 )—, —As(═O)(R 7 )—, —P(═S)(R 7 )—, —As(═S)(R 7 )—, —S(═O)—, —S(═O) 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 9 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; here two or more of these substituents R 2 may also form with one another a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system;
R 3 in each instance, independently of one another, is selected from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical with 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF 3 ; here also two or more substituents R 3 may also form a mono- or polycyclic, aliphatic ring system with one another;
R 4 in each instance, independently of one another, is selected from the group consisting of H, deuterium, phenyl, naphthyl, CN, CF 3 , OH, C(═O)OR 3 , C(═O)N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 7 ) 2 , As(═O)(R 7 ) 2 , P(═S)(R 7 ) 2 , As(═S)(R 7 ) 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a linear alkenyl or alkynyl group with 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C atoms, which in each case may be substituted with one or more radicals R 9 , wherein one or more adjacent CH 2 groups may be replaced by —R 9 C═CR 9 —, —C≡C—, or one adjacent CH 2 -groups by —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, C(═O)N(R 3 )—, —P(═O)(R 7 )—, —As(═O)(R 7 )—, —P(═S)(R 7 ), —As(═S)(R 7 )—, —S(═O)—, —S(═O) 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; here, two or more of these substituents R 4 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system with one another;
R 5 in each instance, independently of one another, is selected from the group consisting of phenyl, naphthyl, CF 3 , C(═O)R 3 , P(═O)(R 7 ) 2 , As(═O)(R 7 ) 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a linear alkenyl or alkynyl group with 2 to 40 C atoms or branched or cyclic alkyl

Assignees

• Cynora Gmbh

Inventors

• Ambrosek David
• Danz Michael
• Flügge Harald
• Friedrichs Jana
• Grab Tobias
• Jacob Andreas
• Seifermann Stefan
• Volz Daniel

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• H01L51/0071

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title