Organic molecules for use in optoelectronic devices
An organic molecule is disclosed comprising: a first chemical moiety with a structure of formula I, and two second chemical moieties, each independently from another with a structure of formula II, wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond.
1. An organic molecule, comprising
a first chemical moiety comprising a structure of Formula I:
and
two second chemical moieties, each independently from another comprising a structure of Formula II,
wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond;
wherein
T is selected from the group consisting of R A and R 1 ;
V is selected from the group consisting of R A and R 1 ;
W is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of R A and R 2 ;
X is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R 2 ;
Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R 2 ;
R A is 1,3,5-triazinyl substituted with two substituents R TZ :
which is bonded to the structure of Formula I via the position marked by the dotted line;
R T is selected from the group consisting of CN and R I ;
R v is selected from the group consisting of CN and R I ;
R W is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of CN and R I ;
R x is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R I ;
R Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R I ;
# represents the binding site of a single bond linking the second chemical moieties to the first chemical moiety;
Z is at each occurrence independently from another 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 ;
R 1 is at each occurrence independently from another 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 R 6 ;
R 2 is at each occurrence independently from another 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 R 6 ;
R I is at each occurrence independently from another 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 R 6 ;
R Tz is at each occurrence independently from another 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 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 a , R 3 and R 4 is at each occurrence independently from another 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 ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 5 ;
R 5 is at each occurrence independently from another 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═0, 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 ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 6 ;
R 6 is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, OPh, CF 3 , CN, F,
C 1 -C 5 -alkyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F;
C 1 -C 5 -alkoxy,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F;
C 1 -C 5 -thioalkoxy,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F;
C 2 -C 5 -alkenyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F;
C 2 -C 5 -alkynyl,
wherein one or more hydrogen atoms are optionally, 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
exactly one substituent selected from the group consisting of T, V and W is R A ,
exactly one substituent selected from the group consisting of R T , R v and R W is CN,
exactly one substituent selected from the group consisting of W, Y and X represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties and
exactly one substituent selected from the group consisting of R W , R Y and R X represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties.
2. The organic molecule according to claim 1 , wherein the first chemical moiety comprises a structure of Formula Ia:
wherein
R z is selected from the group consisting of R I and CN;
R D is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties;
Y D is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties;
and wherein exactly one substituent selected from the group consisting of R v , R T and R Z is CN;
and wherein apart from that the definitions in claim 1 apply.
3. The organic molecule according claim 1 , wherein at each occurrence R 1 , R 2 and R I is independently from each selected from the group consisting of H, methyl, mesityl, tolyl, and phenyl.
4. The organic molecule according to claim 1 , wherein R TZ is independently from each other selected from the group of H, methyl and phenyl.
5. The organic molecule according to claim 1 , wherein the two second chemical moieties each at each occurrence, independently from another, comprise a structure of Formula IIa:
6. The organic molecule according to claim 1 , wherein the two second chemical moieties each at each occurrence, independently from another, comprise a structure of Formula IIb:
wherein
R b is at each occurrence independently from another selected from the group consisting of:
deuterium, N(R 5 ) 2 , OR S , 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 , 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 ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 5 .
7. The organic molecule according to claim 1 , wherein the two second chemical moieties each at each occurrence, independently from another, comprise a structure of Formula IIc:
wherein
R b is at each occurrence independently from another selected from the group consisting of 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═0, 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 ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R 5 .
8. The organic molecule according to claim 6 , wherein R b is at each occurrence independently from another selected from the group consisting of
Me, i Pr, t Bu, CN, CF 3 ,
Ph, 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;
pyridinyl, 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;
pyrimidinyl, 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;
carbazolyl, 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;
triazinyl, 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;
and
N(Ph) 2 .
9. A composition comprising:
(a) at least one organic molecule according to claim 1 as an emitter and/or host;
(b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 1 , and
(c) optionally one or more dyes and/or one or more solvents.
10. An optoelectronic device comprising the organic molecule according to claim 1 .
11. The optoelectronic device according to claim 10 , wherein the optoelectronic device 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 device according to claim 10 , wherein the organic molecule is one of a luminescent emitter, a host material, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.
13. The optoelectronic device according to claim 10 , 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.
14. An optoelectronic device comprising an organic molecule according to claim 2 .
15. The optoelectronic device according to claim 14 , 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.
16. An optoelectronic device comprising the composition according to claim 9 .
17. The optoelectronic device according to claim 16 , 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 composition.
18. The optoelectronic device according to claim 16 , wherein the optoelectronic device 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.
19. 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.
20. A process for producing an optoelectronic device, comprising processing of the composition according to claim 9 by a vacuum evaporation method or from a solution.