Organic molecules for use in organic optoelectronic devices

Patent metadata

Field	Value
Publication number	US-11271174-B2
Application number	US-201716313105-A
Country	US
Kind code	B2
Filing date	Jun 21, 2017
Priority date	Jul 1, 2016
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

An organic molecule for use in optoelectronic components is disclosed having a structure of Formula I

with

X═CN,

D=

wherein

# is the point of attachment of unit D to one of the phenyl rings shown in Formula I;

Z is a direct bond or is selected from the group consisting of CR 3 R 4 , C═CR 3 R 4 , C═O, C═NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O), S(O) 2 ;

In each occurrence R 1 and R 2 is the same or different, is H, deuterium, a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium or an aromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;
and wherein at least one R a is not H, and
wherein at least one R 2 is H.

First claim

The invention claimed is:

1. An organic molecule, comprising a structure of Formula I,

with
X═CN and
D=

wherein
# is the point of attachment of unit D to a phenyl ring of the structure according to Formula I;
Z is a direct bond or is selected from the group consisting of CR 3 R 4 , C═CR 3 R 4 , C═O, C═NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 ;
in each occurrence R 1 and R 2 are the same or different and are selected from the group consisting of:
H, deuterium;
a linear alkyl group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium;
a linear alkenyl or alkynyl group having 2 to 8 C atoms, wherein one or more H atoms can be replaced by deuterium;
a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium; and
an aromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;

in each occurrence R a , R 3 and R 4 is the same or different and is selected from the group consisting of:
H, deuterium, N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 5 ; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R 5 ;

in each occurrence R 5 is the same or different and is selected from the group consisting of:
H, deuterium, N(R 6 ) 2 , OH, Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R 6 ; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R 6 ;

in each occurrence R 6 is the same or different and is selected from the group consisting of:
H, deuterium, OH, CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms;

wherein each of the radicals R a , R 3 , R 4 or R 5 can also form a mono- or polycyclic, aliphatic, aromatic and/or benzoannelated ring system with one or more further radicals R a , R 3 , R 4 or R 5 ; and
wherein at least one R a is not H, and
wherein at least one R 2 is H.

2. The organic molecule according to claim 1 , wherein R 1 is H or methyl and R 2 is H.

3. The organic molecule according to claim 1 , wherein D comprises a structure of Formula IIa:

wherein # and R a have the aforestated meanings.

4. The organic molecule according to claim 1 , wherein D comprises a structure of Formula IIb:

wherein
in each occurrence R b is the same or different and is selected from the group consisting of:
N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which c

Assignees

• Cynora Gmbh

Inventors

• Bergmann Larissa
• Danz Michael
• Zink Daniel

Classifications

• H10K50/10

  OLEDs or polymer light-emitting diodes [PLED] · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/6572

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

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• Y02E10/549

  Organic PV cells · CPC title