Organic molecules for use in optoelectronic devices
An organic molecule having a structure of Formula I for the application in optoelectronic devices: wherein m is an integer from 1 to 2; n is an integer from 0 to 4; o is an integer from 0 to 2; with the sum (m+n+o) being an integer from 1 to 5; and X is selected from the group consisting of hydrogen, CN and CF 3 .
1. An organic molecule comprising a structure of Formula I:
wherein
m is an integer from 1 to 2;
n is an integer from 0 to 4;
o is an integer from 0 to 2;
the sum equal to (m+n+o) is an integer from 1 to 5;
X is selected from the group consisting of hydrogen, CN and CF 3 ;
Ar EWG is at each occurrence independently selected from the group consisting of Formula IIa to IIo:
wherein # marks the binding position of the single bond shown in Formula 1 that bonds Ar EWG to the phenyl ring;
R a and R b are each independently selected from the group consisting of
hydrogen, deuterium,
C 1 -C 5 -alkyl,
C 2 -C 8 -alkenyl,
C 2 -C 8 -alkinyl, and
C 6 -C 18 -aryl,
which is optionally substituted with one or more substituents R m ;
R C at each occurrence is independently selected from the group consisting of hydrogen, deuterium, N(R m ) 2 , OR m , Si(R m ) 3 , B(OR m ) 2 , OSO 2 R m , CF 3 , CN, F, Br, I, C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkinyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R m ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R m ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 8 , R 9 and R 10 are each independently selected from the group consisting of:
hydrogen, deuterium, N(R m ) 2 , OR m , SR m , Si(R m ) 3 , B(OR m ) 2 , OSO 2 R m , CF 3 , CN, halogen,
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R m ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R m ;
R 4 is independently selected from the group consisting of:
a direct bond to R X to form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system,
hydrogen, deuterium, N(R m ) 2 , OR m , SR m , Si(R m ) 3 , B(OR m ) 2 , OSO 2 R m , CF 3 , CN, halogen,
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R m ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R m ;
R 7 is independently selected from the group consisting of:
a direct bond to R Y to form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system,
hydrogen, deuterium, N(R m ) 2 , OR m , SR m , Si(R m ) 3 , B(OR m ) 2 , OSO 2 R m , CF 3 , CN, halogen,
C 1 -C 40 -alkyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -alkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 1 -C 40 -thioalkoxy,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkenyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 2 -C 40 -alkynyl,
which is optionally substituted with one or more substituents R m and
wherein one or more non-adjacent CH 2 -groups are optionally substituted by R m C═CR m , C≡C, Si(R m ) 2 , Ge(R m ) 2 , Sn(R m ) 2 , C═O, C═S, C═Se, C═NR m , P(═O)(R m ), SO, SO 2 , NR m , O, S or CONR m ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R m ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R m ;
R 11 and R 12 are each independently selected from the group consisting of hydrogen, deuterium,
C 1 -C 5 -alkyl,
C 2 -C 8 -alkenyl,
C 2 -C 8 -alkinyl,
C 6 -C 18 -aryl,
which is optionally substituted with one or more substituents selected form the group of C 1 -C 5 -alkyl and C 6 -C 18 -aryl, and
C 3 -C 12 -heteroaryl,
which is optionally substituted with one or more substituents selected form the group of C 1 -C 5 -alkyl and C 6 -C 18 -aryl;
R 13 is selected from the group consisting of hydrogen, deuterium,
C 1 -C 5 -alkyl,
C 2 -C 8 -alkenyl,
C 2 -C 8 -alkinyl, and
C 6 -C 18 -aryl,
which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;
R X is selected from the group consisting of:
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused rind system with R 4 ,
C 1 -C 5 -alkyl,
which is optionally substituted with one or more substituents R m ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R m ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R m ;
R Y is selected from the group consisting of:
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with R 7 ,
C 1 -C 5 -alkyl,
which is optionally substituted with one or more substituents R m ;
C 6 -C 60 -aryl,
which is optionally substituted with one or more substituents R m ; and
C 3 -C 57 -heteroaryl,
which is optionally substituted with one or more substituents R m ;
R m is at each occurrence independently selected from the group consisting of:
hydrogen, deuterium, OPh, SPh, CF 3 , CN, F, Si(C 1 -C 5 -alkyl) 3 , Si(Ph) 3 ,
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).
2. The organic molecule according to claim 1 , wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 8 , R 9 and R 19 are each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 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 , 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 ;
R 4 is selected from the group consisting of:
a direct bond to R X to form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system,
hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 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 , 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 ;
R 7 is selected from the group consisting of:
a direct bond to R Y to form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system,
hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 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 , 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 ;
R 11 and R 12 are at each occurrence independently selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, Ph, and
triazine, which is optionally substituted with one or more Ph;
R 13 is at each occurrence independently selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, and Ph;
R X is selected from the group consisting of:
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with R 4 ,
C 1 -C 5 -alkyl,
C 6 -C 18 -aryl, and
C 3 -C 57 -heteroaryl,
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
R Y is selected from the group consisting of:
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with R 7 ,
C 1 -C 5 -alkyl,
C 6 -C 18 -aryl, and
C 3 -C 57 -heteroaryl,
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.
3. The organic molecule according to claim 2 , wherein m is 1 and o is 0.
4. The organic molecule according to claim 2 , wherein m is 1 and o is 1.
5. The organic molecule according to claim 1 , wherein m is 2 and o is 0.
6. An optoelectronic device comprising the organic molecule according to claim 2 , 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.
7. The optoelectronic device according to claim 6 , 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 arranged between the anode and the cathode and which comprises the organic molecule.
8. The organic molecule according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, SiMe 3 , SiPh 3 , and 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, Ph, and N(Ph) 2 ;
wherein
R X and R Y are each independently selected from the group consisting of Me, i Pr, t Bu, and Ph.
9. The organic molecule according to claim 1 , wherein m is 1 and o is 0.
10. The organic molecule according to claim 1 , wherein m is 1 and o is 1.
11. The organic molecule according to claim 1 , wherein Ar EWG is selected from the group consisting of Formula Ila and Formula Ilb:
12. 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; and
(c) optionally one or more dyes and/or one or more solvents.
13. An optoelectronic device comprising the composition according to claim 10 .
14. The optoelectronic device according to claim 13 , 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.
15. The optoelectronic device according to claim 14 , 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 arranged between the anode and the cathode and which comprises the composition.
16. An optoelectronic device comprising the organic molecule according to claim 1 .
17. The optoelectronic device according to claim 16 , 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.
18. The optoelectronic device according to claim 17 , 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 arranged between the anode and the cathode and which comprises the organic molecule.
19. 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.
20. A method for producing an optoelectronic device, comprising processing of the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.