Organic molecules for use in organic optoelectronic devices
An organic molecule is disclosed comprising: a first chemical unit having a structure according, to Formula I and two second chemical units, which in each case are the same or different in each occurrence, having a structure according to Formula II, wherein, in each case, the first chemical unit is connected to the two second chemical units via a single bond.
1. An organic molecule, comprising:
a first chemical unit comprising a structure according to Formula I:
and
two second chemical units, which are respectively the same or different in each occurrence, comprising a structure according to Formula II:
wherein, in each case, the first chemical unit is connected to the two second chemical units via a single bond;
wherein
T is the point of attachment of the single bond between the first chemical unit and a second chemical unit or is H;
V is the point of attachment of the single bond between the first chemical unit and a second chemical unit or is H;
W is the point of attachment of the single bond between the first chemical unit and a second chemical unit or is selected from the group consisting of H, CN and CF 3 ;
X is the point of attachment of the single bond between the first chemical unit and a second chemical unit or is selected from the group consisting of H, CN and CF 3 ;
Y is the point of attachment of the single bond between the first chemical unit and a second chemical unit or is selected from the group consisting of H, CN and CF 3 ;
# identifies the point of attachment of the single bond between a second chemical unit and the first chemical unit;
Z is the same or different in each occurrence, is a direct bond or is selected from the group consisting of 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 the same or different in each occurrence and is selected from the group consisting of:
H, deuterium;
a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms in the aforementioned groups can be replaced by deuterium; and
an aromatic ring system having 6 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;
R 2 is selected from the group consisting of H and deuterium;
R a , R 3 and R 4 is the same or different in each occurrence and is selected from the group consisting of:
H, deuterium, N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic ring system having 6 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
R 5 is the same or different in each occurrence and is selected from the group consisting of:
H, deuterium, N(R 6 ) 2 , OH, Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 6 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic ring system having 6 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;
a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can in each case be substituted with one or more radicals R 6 ;
R 6 is the same or different in each occurrence and is selected from the group consisting of:
H, deuterium, OH, CF 3 , CN, F;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic ring system having 6 to 60 aromatic ring atoms;
a heteroaromatic ring system having 5 to 60 aromatic ring atoms;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms;
wherein each of the radicals R a , R 3 , R 4 or R 5 can also form a mono- or polycyclic, aliphatic, aromatic and/or benzoannelated ring system with one or more further radicals R a , R 3 , R 4 or R 5 ;
wherein
exactly one radical selected from the group consisting of W, X and Y is CN or CF 3 and exactly two radicals selected from the group consisting of T, V, W, X and Y are a point of attachment of the single bond between the first chemical unit and a second chemical unit.
2. The organic molecule according to claim 1 , wherein R 1 is the same or different in each occurrence and is methyl or phenyl.
3. The organic molecule according to claim 1 , wherein R 2 is H.
4. The organic molecule according to claim 1 , wherein W is CN.
5. The organic molecule according to claim 1 , wherein the second chemical unit is the same or different in each occurrence and has a structure of Formula IIa:
6. The organic molecule according to claim 1 , wherein, in each case, the second chemical unit has a structure of Formula IIb:
wherein
R b is the same or different in each occurrence and is selected from the group consisting of:
N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSOR 5 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic ring system having 6 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 .
7. The organic molecule according to claim 1 , wherein, in each case, the second chemical unit has a structure of Formula IIc:
wherein
R b is the same or different in each occurrence and is selected from the group consisting of:
N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSOR 5 , CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 40 C atoms, wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R 5 , wherein one or more non-adjacent CH 2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic ring system having 6 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 ; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can in each case be substituted with one or more radicals R 5 .
8. The organic molecule according to claim 6 , wherein R b is the same or different in each occurrence and is selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 ,
Ph, which can in each case be substituted with one or more radicals selected independently of one another from Me, i Pr, t Bu, CN, CF 3 or Ph,
pyridinyl, which can in each case be substituted with one or more radicals selected independently of one another from Me, i Pr, t Bu, CN, CF 3 or Ph,
pyrimidinyl, which can in each case be substituted with one or more radicals selected independently of one another from Me, i Pr, t Bu, CN, CF 3 or Ph,
triazinyl, which can in each case be substituted with one or more radicals selected independently of one another from Me, i Pr, t Bu, CN, CF 3 or Ph,
carbazolyl which can in each case be substituted with one or more radicals selected independently of one another from Me, i Pr, t Bu, CN, CF 3 or 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, 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.
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 the 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, 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. 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.