Organic molecules for use in optoelectronic devices
Organic molecules are provided for use in 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). The 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 a higher stability than OLEDs with known emitter materials and comparable color.
1. An organic molecule, comprising:
a structure of Formula IV:
wherein
R T is selected from the group consisting of CF 3 and R I ;
R V is selected from the group consisting of CF 3 and R I ;
R Z is selected from the group consisting of CF 3 and R I ;
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 phenyl;
R a 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, optionally, each substituent R a independently from each other forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R a ;
wherein
exactly one substituent selected from the group consisting of R T , R V and R Z is CF 3 .
2. The organic molecule according to claim 1 , comprising a structure of Formula IV-1 or IV-2:
3. The organic molecule according to claim 1 , wherein R 1 , R 2 and R I are at each occurrence independently from each other selected from the group consisting of H, methyl, mesityl, tolyl, and phenyl.
4. The organic molecule according to claim 1 , wherein the structure of Formula IV is selected from the group consisting of Formula IVa-1, Formula IVa-2, Formula IVb-1, Formula IVb-2, Formula IVc-1 Formula IVc-2, Formula IVd-1 and Formula IVd-2:
wherein R c is at each occurrence independently from another selected from the group consisting of Me, i Pr, t Bu, 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; and 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.
5. The organic molecule according to claim 1 , wherein the portions of the molecule that have the structure of Formula II:
each at each occurrence independently from another have a structure of Formula IIc:
wherein
# represents the binding site of a single bond linking the structure of Formula IIc to the remaining portion of the structure of Formula IV;
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 .
6. The organic molecule according to claim 5 , 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 .
7. A composition, comprising:
(a) at least one organic molecule according to claim 1 ;
(b) one or more emitter and/or host materials, which are different from the organic molecule of claim 1 ; and
(c) optionally, one or more dyes and/or one or more solvents.
8. An optoelectronic device, comprising the organic molecule according to claim 1 .
9. The optoelectronic device according to claim 8 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode are disposed on the substrate; and
at least a light-emitting layer, which is arranged between the anode and the cathode and which comprises the organic molecule according to claim 1 .
10. The optoelectronic device according to claim 8 , in the 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.
11. An optoelectronic device, comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode are disposed on the substrate; and
at least a light-emitting layer, which is arranged between the anode and the cathode and which comprises the organic molecule according to claim 2 .
12. An optoelectronic device, comprising the composition according to claim 7 .
13. The optoelectronic device according to claim 12 , comprising:
a substrate;
an anode;
a cathode, wherein the anode or the cathode are disposed on the substrate; and
at least a light-emitting layer, which is arranged between the anode and the cathode and which comprises the composition according to claim 7 .
14. The optoelectronic device according to claim 12 , in the 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.