Organic molecules for optoelectronic devices
An organic molecule is disclosed having: one first chemical moiety with a structure of Formula I, and three second chemical moieties, each independently from another with a structure of Formula II, wherein the first chemical moiety is linked to each of the three second chemical moieties via a single bond.
1. An organic molecule, comprising:
a first chemical moiety comprising a structure of Formula I,
three second chemical moieties, each independently comprising a structure of Formula II,
wherein
the first chemical moiety is linked to each of the three second chemical moieties via a single bond;
Y is the binding site of a single bond linking the first chemical moiety to one of the three second chemical moieties;
T, V, W is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the three second chemical moiety, and R 1 ;
Z is at each occurrence independently selected from the group consisting of a direct bond, 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 ;
#represents the binding site of a single bond linking the first chemical moiety to the second chemical moiety;
Q is selected from the group consisting of N and C—R Py ;
R Tz is at each occurrence independently selected from the group consisting of hydrogen,
deuterium,
C 1 -C 5 -alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 2 -C 8 -alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 2 -C 8 -alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 6 -C 18 -aryl,
which is optionally substituted with one or more substituents R 5 ; and
C 3 -C 17 -heteroaryl,
which is optionally substituted with one or more substituents R 5 ;
R Py is at each occurrence independently selected from the group consisting of hydrogen,
deuterium,
C 1 -C 5 -alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 2 -C 8 -alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 2 -C 8 -alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 6 -C 18 -aryl,
which is optionally substituted with one or more substituents R 6 ; and
C 3 -C 17 -heteroaryl,
which is optionally substituted with one or more substituents R 6 ;
R 1 is at each occurrence independently selected from the group consisting of hydrogen,
deuterium,
C 1 -C 5 -alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 2 -C 8 -alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C 2 -C 8 -alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and
C 6 -C 18 -aryl,
which is optionally substituted with one or more substituents independently selected from the group consisting of
C 1 -C 5 -alkyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
and
C 6 -C 18 -aryl,
which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;
R a , R 3 and R 4 is at each occurrence independently selected from the group consisting of hydrogen,
deuterium,
N(R 5 ) 2 ,
OR 5 ,
Si(R 5 ) 3 ,
B(OR 5 ) 2 ,
OSO 2 R 5 ,
CF 3 ,
CN,
F,
Br,
I,
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R 5 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R 5 ;
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 5 ; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring-closure with one or more of the other substituents selected from the group consisting of R a , R 3 , R 4 and R 5 ;
R 5 is at each occurrence independently selected from the group consisting of hydrogen,
deuterium,
N(R 6 ) 2 ,
OR 6 ,
Si(R 6 ) 3 ,
B(OR 6 ) 2 ,
OSO 2 R 6 ,
CF 3 ,
CN,
F,
Br,
I,
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R 6 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R 6 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R 6 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R 6 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R 6 and
wherein one or more non-adjacent CH 2 -groups are optionally substituted 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 ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R 6 ;
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 6 ; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring-closure with one or more of the other substituents selected from the group consisting of R a , R 3 , R 4 and R 5 ;
R 6 is at each occurrence independently selected from the group consisting of hydrogen,
deuterium,
OPh,
CF 3 ,
CN,
F,
C 1 -C 5 -alkyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
C 1 -C 5 -alkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
C 1 -C 5 -thioalkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
C 2 -C 5 -alkenyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
C 2 -C 5 -alkynyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
C 6 -C 18 -aryl,
which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;
C 3 -C 17 -heteroaryl,
which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;
N(C 6 -C 18 -aryl) 2 ;
N(C 3 -C 17 -heteroaryl) 2 ; and
N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl);
wherein the substituents R a , R 3 , R 4 or R 5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R a , R 3 , R 4 or R 5 ;
wherein the mono- or polycyclic aliphatic, aromatic and/or benzo-fused ring system is optionally substituted with at least one substituent R 5 , and
optionally forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system together with one or more of the other R a , R 3 , R 4 or R 5 within the organic molecule;
wherein the mono- or polycyclic aliphatic, aromatic and/or benzo-fused ring system is optionally substituted with at least one substituent R 6 ;
wherein two substituents in exactly one group of a same letter selected from the group consisting of both of Ts, both of Vs and both of Ws each represent the binding site of a single bond linking the first chemical moiety and one of the three second chemical moieties, wherein the three second chemical moieties each individually are the same or different from each other,
and
wherein at least one ring member Q is N.
2. The organic molecule according to claim 1 , comprising:
a first chemical moiety comprising a structure of Formula I-Y,
wherein
T # is R 1 or is the binding site of a single bond linking the first chemical moiety to one of the three second chemical moieties;
W # is R 1 or is the binding site of a single bond linking the first chemical moiety to one of the three second chemical moieties; and
two substituents in exactly one group of a same letter selected from the group consisting of both of T # s and both of W # s represent the binding site of a single bond linking the first chemical moiety.
3. The organic molecule according to claim 1 , wherein R 1 and R Py are H at each occurrence and R Tz is phenyl at each occurrence which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph.
4. The organic molecule according to claim 1 , wherein the three second chemical moieties each individually from each other comprise a structure of Formula IIa:
5. The organic molecule according to claim 1 , wherein one of the three second chemical moieties is attached to Y and comprises a structure of Formula IIa:
and wherein the other two of the three second chemical moieties comprise a structure of Formula III:
6. The organic molecule according to claim 1 , wherein the organic molecule comprises a structure of Formula I-YYY:
7. The organic molecule according to claim 1 , wherein exactly two immediately ring-adjacent R a form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system.
8. A composition comprising:
(a) at least one organic molecule according to claim 1 as an emitter and/or a host;
(b) one or more emitter and/or host materials different from the organic molecule according to claim 1 , and
(c) optionally one or more dyes and/or one or more solvents.
9. An optoelectronic device comprising the organic molecule according to claim 1 .
10. The optoelectronic device according to claim 9 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an 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.
11. The optoelectronic device according to claim 10 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode is disposed on the substrate; and
at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.
12. An optoelectronic device comprising the organic molecule according to claim 1 , wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.
13. An optoelectronic device comprising the organic molecule according to claim 4 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an 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.
14. The optoelectronic device according to claim 13 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode is applied to the substrate; and
at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.
15. An optoelectronic device comprising the organic molecule according to claim 5 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an 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.
16. The optoelectronic device according to claim 15 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode is applied to the substrate; and
at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.
17. An optoelectronic device comprising the composition according to claim 8 .
18. The optoelectronic device according to claim 17 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an 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.
19. The optoelectronic device according to claim 18 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode is disposed on the substrate; and
at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.
20. A process for producing an optoelectronic device, comprising processing of the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.