Organic molecules for use in optoelectronic devices
Organic molecules are provided for use in organic optoelectronic devices. The organic molecules are purely organic molecules, i.e., they do not contain any metal ions. The organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The organic molecules exhibit emission maxima between 420 nm and 520 nm, between 440 nm and 495 nm, or between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules are 20% or more. The molecules exhibit thermally activated delayed fluorescence (TADF). Use of the molecules in an optoelectronic device, e.g., an organic light-emitting diode (OLED) leads to higher efficiencies of the device. Corresponding OLEDs have higher stabilities than OLEDs with known emitter materials and comparable color.
1. An organic molecule, comprising:
one 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 the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, R A and R 1 ;
V is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, R A and R 1 ;
W is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, R A and R 1 ;
X is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, R A and R 1 ;
Y is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, R A and R 1 ;
R A is consisting of a structure of Formula A1,
wherein $ represents the binding site of the single bond connecting R A to the first chemical moiety as shown in Formula I;
A I , A II , A III , A IV and A V are each selected from the group consisting of CF 3 and R I ;
R T is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R 2 ;
R V is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R 2 ;
R W is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R 2 ;
R X is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R 2 ;
R Y is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R 2 ;
# 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 selected from the group consisting of hydrogen, deuterium, OPh, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl and C 2 -C 5 -alkynyl,
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 selected from the group consisting of hydrogen, deuterium, OPh, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl and C 2 -C 5 -alkynyl,
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; and
C 6 -C 18 -aryl,
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═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 ; 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 optionally form, independently from each other, 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, W, X and Y is R A ;
exactly one substituent selected from the group consisting of R T , R V , R W , R X and R Y is CN;
exactly one substituent selected from the group consisting of T, V, W, X and Y represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties;
exactly one substituent selected from the group consisting of R T , R V , R W , R X and R Y represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties; and
exactly two substituents selected from the group consisting of A I , A II , A III , A IV and A V are CF 3 .
2. The organic molecule according to claim 1 , 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 to one of the two second chemical moieties;
exactly one substituent selected from the group consisting of R W , R X and R Y represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties.
3. The organic molecule according to claim 1 , wherein the first chemical moiety comprises a structure of Formula Ia:
wherein
Y D represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties;
R YD represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties;
Q is independently from each other at each occurrence selected from the group consisting of
R 1 and R A ;
R Q is independently from each other at each occurrence selected from the group consisting of
R 2 and CN;
wherein exactly one substituent R Q is CN; and
wherein exactly one substituent Q is R A .
4. The organic molecule according to claim 1 , wherein R 1 , R 2 and R I are individually at each occurrence independently from another selected from the group consisting of H, methyl, mesityl, tolyl, and phenyl.
5. The organic molecule according to claim 1 , wherein each of the two second chemical moieties independently from another comprise a structure of Formula IIa:
6. The organic molecule according to claim 5 , wherein each of the two second chemical moieties 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 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 .
7. The organic molecule according to claim 5 , wherein each of the two second chemical moieties 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═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 .
8. The organic molecule according to claim 6 , wherein each R b is 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. The organic molecule according to claim 7 , wherein each R b is 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 .
10. A composition, comprising:
(a) at least one organic molecule according to claim 1 ; and
(b) one or more emitter and/or host materials, which are different from the organic molecule of claim 1 .
11. The composition according to claim 10 , wherein the at least one organic molecule according to claim 1 is in a form of an emitter and/or a host.
12. An optoelectronic device, comprising an organic molecule according to claim 1 .
13. The optoelectronic device according to claim 12 , in a form of a device selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell, an OLED-sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser and a down-conversion element.
14. The optoelectronic device according to claim 12 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode are disposed on a substrate; and
at least one light-emitting layer, which is arranged between the anode and the cathode and which comprises an organic molecule according to claim 1 .
15. The optoelectronic device according to claim 12 , wherein the organic molecule according to claim 1 is configured as one or more of a luminescent emitter, a host material, an electron transport material, a hole injection material, and a hole blocking material.
16. A method for producing an optoelectronic device, wherein an organic molecule according to claim 1 is deposited on a solid support.
17. The method for producing an optoelectronic device of claim 16 , wherein the organic molecule is deposited by a vacuum evaporation method or from a solution.
18. An optoelectronic device, comprising a composition according to claim 10 .
19. The optoelectronic device according to claim 18 , in a form of a device selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell, an OLED-sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser and a down-conversion element.
20. The optoelectronic device according to claim 18 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode are disposed on a substrate; and
at least one light-emitting layer, which is arranged between the anode and the cathode and which comprises a composition according to claim 10 .