IP Library Granted Patent US 10,669,473
Granted Patent B2
US 10,669,473 · App. 15/544,557 · Granted Jun 2, 2020

Organic molecules for use in optoelectronic components

Inventors: David Ambrosek (Berlin, DE); Michael Danz (Eggenstein-Leopoldshafen, DE); Harald Flügge (Karlsruhe, DE); Jana Friedrichs (Karlsruhe, DE); Tobias Grab (Karlsruhe, DE); Andreas Jacob (Hannover, DE); Stefan Seifermann (Brühl, DE); Daniel Volz (Karlsruhe, DE)
Assignee: CYNORA GMBH
C09K11/06H01L51/0067H01L51/0071H01L51/0072H01L51/5004C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1051C09K2211/1059C09K2211/1074H01L51/5012Y02E10/549Y02P70/521
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Quick Facts
Patent No.
US 10,669,473
App. No.
15/544,557
Granted
Jun 2, 2020
Kind
B2
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.

Claims (102)

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, 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 —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; in this connection two or more of these substituents R 5 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system;

R 6 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 , 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 may be substituted in each case 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 —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 or more radicals R*, 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; in this process two or more of these substituents R 6 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system with one another;

R 7 is in each instance, independently of one another, selected from the group consisting of phenyl, naphthyl, CN, CF 3 , C(═O)OR 3 , C(═O)N(R 3 ) 2 , C(═O)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 replaced by —R 9 C═CR 9 —, —C≡C—, or one adjacent CH 2 -group by —Sn(R 4 ) 2 , —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, —C(═O)N(R 3 )—, —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 3 , or a combination of these systems; here, two or more of these substituents R 7 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system;

R 8 is in each instance independently of one another selected from the group consisting of H, deuterium, phenyl, naphthyl, F, 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, two or more substituents R 8 may also form a mono- or polycyclic, aliphatic ring system; and

R 9 is in each instance independently of one another selected from the group consisting of H, deuterium, phenyl, naphthyl, CN, CF 3 , NO 2 , OH, COOH, C(═O)OR 3 , C(═O)N(R 3 ) 2 , C(═O)R 3 , S(═O)R 3 , S(═O) 2 R 3 , OSO 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 8 , wherein one or more non-adjacent CH 2 groups may be replaced by —R 3 C═CR 3 —, or one adjacent CH 2 -group by —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, —C(═O)N(R 3 )—, —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 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 3 , 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 8 , or a combination of these systems; here, two or more of these substituents R 9 may also form with one another a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system.

2. The organic molecule according to claim 1 , wherein AF2 is selected as one of the following structures, wherein the possible linking points on the separator or on the chemical entity AF2 are designated with lower-case letters a to z and a 2 to k 2 ;

3. The organic molecule according to claim 1 , wherein the separator is selected from the group of following structures:

wherein # represent the linking points for the chemical entities AF1 and AF2.

4. An optoelectronic component, comprising an organic molecule according to claim 1 .

5. The optoelectronic component according to claim 4 , comprising

a substrate,

an anode,

a cathode, wherein the anode and the cathode are applied to the substrate, and

at least one light-emitting layer applied between the anode and cathode and containing the organic molecule.

6. The optoelectronic component according to claim 5 , wherein the light-emitting layer contains fluorescent or phosphorescent materials and wherein the materials of the light-emitting layer are the organic molecules.

7. The optoelectronic component according to claim 4 , in which the light-emitting layer comprises at least one host material, wherein the excited singlet state (S 1 ) and/or the excited triplet state (T 1 ) of the at least one host material is higher than that of the excited singlet state (S 1 ) and/or the excited triplet state (T 1 ) of the organic molecule.

8. The optoelectronic component according to claim 4 , comprising at least one host material consisting of the organic molecule.

9. The optoelectronic component according to claim 4 , in which the organic molecule together with a functional material form an exciplex.

10. The optoelectronic component according to claim 4 , in which the organic molecule is part of a charge transport layer.

11. The optoelectronic component according to claim 4 , wherein the optoelectronic component is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

12. The optoelectronic component according to claim 4 , wherein the organic molecule is one of a luminescent emitter, an absorber, a host material, an electron transport material, a hole injection material, and a hole blocking material.

13. The optoelectronic component according to claim 12 , wherein a proportion of the organic molecule in an emission layer in the optoelectronic component is 1% to 99%.

14. The optoelectronic component according to claim 12 , wherein a proportion of the organic molecule in an emission layer in the optoelectronic component is 5% to 80%.

15. A method for producing an optoelectronic component, comprising processing the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

16. 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 is selected from the following structures:

wherein the possible linking points on the separator or on the chemical entity AF2 are designated with lower-case letters a, b, d and e; and wherein AF2 comprises a structure of formula 3:

wherein:

n is 0 or 1;

p is 0 or 1;

VG1=bridging group selected from the group consisting of

NR**, CR** 2 , O, S, a direct bond, BR**, AsR**, SiR** 2 , GeR** 2 ,

VG2=bridging group is in each instance, independently of one another, selected from the group consisting of CR** 2 , NR**, O, S and a direct bond, wherein two entities VG2 are not simultaneously a direct bond;

E is NR**

O or S;

L is CR*** when n=0; L is CR** or C (in the case of covalent bonding to VG2 when n=1;

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 and formula 3:

R* in each instance, independently of one another, is selected from the group consisting of H, deuterium, phenyl, naphthyl, —CN, 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 ), C(═O)R 3 , P(═O)(R 7 ) 2 , As(═O)(R 7 ), 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, 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 —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; in this connection two or more of these substituents R 5 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system;

R 6 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 , 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 may be substituted in each case 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 —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 or more radicals R*, 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; in this process two or more of these substituents R 6 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system with one another;

R 7 is in each instance, independently of one another, selected from the group consisting of phenyl, naphthyl, CN, CF 3 , C(═O)OR 3 , C(═O)N(R 3 ) 2 , C(═O)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 replaced by —R 9 C═CR 9 —, —C≡C—, or one adjacent CH 2 -group by —Sn(R 4 ), —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, —C(═O)N(R 3 )—, —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 3 , or a combination of these systems; here, two or more of these substituents R 7 may also form a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system;

R 8 is in each instance independently of one another selected from the group consisting of H, deuterium, phenyl, naphthyl, F, 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, two or more substituents R 8 may also form a mono- or polycyclic, aliphatic ring system; and

R 9 is in each instance independently of one another selected from the group consisting of H, deuterium, phenyl, naphthyl, CN, CF 3 , NO 2 , OH, COOH, C(═O)OR 3 , C(═O)N(R 3 ), C(═O)R 3 , S(═O)R 3 , S(═O) 2 R 3 , OSO 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 8 , wherein one or more non-adjacent CH 2 groups may be replaced by —R 3 C═CR 3 —, —C≡C—, or one adjacent CH 2 -group by —C(═O)—, —C(═S)—, —C(═Se)—, —C═N—, —C(═O)O—, —C(═O)N(R 3 )—, —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 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 3 , 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 8 , or a combination of these systems; here, two or more of these substituents R 9 may also form with one another a mono- or polycyclic, aliphatic, aromatic and/or benzoanellated ring system.

17. The organic molecule according to claim 16 , 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.

18. The organic molecule according to claim 17 , wherein AF2 is selected as one of the following structures, wherein the possible linking points on the separator or on the chemical entity AF2 are designated with lower-case letters a to z and a 2 to k 2 ;

19. An optoelectronic component, comprising an organic molecule according to claim 16 .

20. The optoelectronic component according to claim 19 , comprising

a substrate,

an anode,

a cathode, wherein the anode and the cathode are applied to the substrate, and

at least one light-emitting layer applied between the anode and cathode and containing the organic molecule.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2022
From: CYNORA GMBH
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 060329/0712 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2017
From: AMBROSEK, DAVID; DANZ, MICHAEL; FLÜGGE, HARALD; FRIEDRICHS, JANA; GRAB, TOBIAS; JACOB, ANDREAS; SEIFERMANN, STEFAN; VOLZ, DANIEL
To: CYNORA GMBH
Reel/Frame 043228/0344 →
Priority Claims (2)
EP 15151870 · Jan 20, 2015 · regional
DE 10 2015 107 905 · May 20, 2015 · national
Continuity (1)
Related Publication 20180265777A1 · Sep 20, 2018
Cited By (4)
US 12,281,106 US 12,336,369 US 12,336,425 US 12,543,498