Organic molecules for use in optoelectronic devices
The invention relates to an organic molecule having a structure of the formula I where X=CN or CF 3 ; D=chemical unit having a structure of the formula I-1: where #=attachment point of the unit of formula I-1 to the central phenyl ring in the structure of formula I; A and B=independently of one another are selected from the group consisting of CRR 1 , CR, NR, N, there being a single or double bond between A and B and a single or double bond between B and Z; and Z=a direct bond or a divalent organic bridge which is a substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group or a combination thereof, —CRR 1 , —C═CRR 1 , —C═NR, —NR—, —O—, —SiRR 1 —, —S—, —S(O)—, —S(O) 2 —, O-interrupted substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group, phenyl units or substituted phenyl units.
1. An optoelectronic device comprising at least one light-emitting layer,
wherein the at least one light emitting layer consists of an organic molecule comprising a structure of Formula I and a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule,
wherein the organic molecule is a luminescent emitter,
wherein the at least one light emitting layer comprises no additional emitter material:
wherein
X=CN or CF 3 ;
D=a chemical unit comprising a structure of Formula 1-1:
wherein
#=an attachment point of the unit of Formula I-1 to a central phenyl ring of the structure of Formula I;
A and B=independently of one another are selected from the group consisting of CRR 1 , CR, NR, and N, there being a single or double bond between A and B and a single or double bond between B and Z;
Z=a direct bond or a divalent organic bridge which is a substituted or unsubstituted C 1 to C 9 -alkylene, C 2 to C 8 -alkenylene, C 2 to C 8 -alkynylene or arylene group or a combination thereof,
—C(Me) 2 , —C═CRR 1 , C═NR, —NR—, —O—, —SiRR 1 —, —S—, —S(O)—, —S(O) 2 —, O-interrupted substituted or unsubstituted C 1 to C 9 -alkylene, C 2 to C 8 -alkenylene, C 2 to C 8 -alkynylene or arylene group, phenyl units or substituted phenyl units;
where each R and R 1 , identically or differently at each occurrence, is H, deuterium, azide (N 3 − ), F, Cl, Br, I, N(R 2 ) 2 , CN, CF 3 , NO 2 , OH, COOH, COOR 2 , CO (NR 2 ) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O) R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, which in each case may be substituted by one or more radicals R 2 , it being possible for one or more non-adjacent CH 2 groups to be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 , and it being possible for one or more H atoms to be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or is an aromatic hydrocarbon ring system having 6 to 60 aromatic ring atoms optionally substituted by one or more radicals R 2 or a heteroaromatic ring system having 5 to 60 aromatic ring atoms, or is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy or the heteroaryloxy group is optionally substituted by one or more radicals R 2 , or is a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, wherein the diarylamino group, the diheteroarylamino group or the arylheteroarylamino is optionally substituted by one or more radicals R 2 , or is a combination of these systems, or is a crosslinkable unit QE which may be crosslinked by acid-catalytic, thermal or UV crosslinking methods in the presence or absence of a photoinitiator or by microwave radiation; optionally two or more of these substituents R and R 1 may form with one another a mono-or polycyclic, aliphatic, aromatic and/or benzo-fused ring system, wherein, when any R combines to form a carbazole group bonded to Formula I-1, the carbazole group is bonded to Formula I-1 through the nitrogen atom of the carbazole group;
R 2 , identically or differently at each occurrence, is H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , CN, CF 3 , NO 2 , OH, COOH, COOR 3 , CO(NR 3 ) 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may be substituted in each case by one or more radicals R 3 , it being possible for one or more non-adjacent CH 2 groups to be replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 , and it being possible for one or more H atoms to be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or the heteroaromatic ring system is optionally substituted in each case by one or more radicals R 3 , or is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy or the heteroaryloxy group is optionally substituted by one or more radicals R 3 , or is a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, wherein the diarylamino group, the diheteroarylamino group or the arylheteroarylamino is optionally substituted by one or more radicals R 3 , or is a combination of these systems; where optionally two or more of these substituents R 2 form with one another a mono-or polycyclic, aliphatic, aromatic and/or benzo-fused ring system;
R 3 , identically or differently at each occurrence, is H, deuterium, F, CF 3 or an aliphatic, aromatic and/or heteroaromatic radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF 3 ; where optionally two or more substituents R 3 form with one another a mono-or polycyclic, aliphatic ring system;
R′=selected from the group consisting of H, N (R 4 ) 2 , OR 4 , thiophene, a linear alkyl or alkoxy group having 1 to 40 C atoms and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, it being possible for this group to be substituted in each case by one or more radicals R 4 , and an aromatic hydrocarbon ring system having 6 to 60 aromatic ring atoms, wherein the aromatic ring system is optionally substituted in each case by one or more radicals R 4 ;
R″=selected from the group consisting of N(R 4 ) 2 , OR 4 , thiophene, a linear alkyl or alkoxy group having 1 to 40 C atoms and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, it being possible for this group to be substituted in each case by one or more radicals R 4 , and an aromatic hydrocarbon ring system having 6 to 60 aromatic ring atoms, wherein the aromatic ring system is optionally substituted by one or more radicals R 4 :
R 4 , identically or differently at each occurrence, is H, deuterium, N(R 5 ) 2 , Si(R 5 ) 3 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, it being possible for this group to be substituted in each case by one or more radicals R 5 , or is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or the heteroaromatic ring system is optionally substituted in each case by one or more radicals R 5 , or is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy or the heteroaryloxy group is optionally substituted by one or more radicals R 5 , or is a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms wherein the diarylamino group, the diheteroarylamino group or the arylheteroarylamino is optionally substituted by one or more radicals R 5 , or is a combination of these systems; where optionally two or more of these substituents R 5 may also form with one another a mono-or polycyclic, aliphatic, aromatic and/or benzo-fused ring system; and
R 5 , identically or differently at each occurrence, is H, deuterium or an aliphatic, aromatic and/or heteroaromatic radical having 1 to 20 carbon atoms; where optionally two or more substituents R 5 may also form with one another a mono-or polycyclic, aliphatic ring system.
2. The optoelectronic device according to claim 1 , 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.
3. The optoelectronic device according to claim 2 , wherein a proportion of the organic molecule in an emission layer in the optoelectronic device is 1 vol. % to 99 vol. %.
4. The optoelectronic device according to claim 2 , wherein a proportion of the organic molecule in an emission layer in the optoelectronic device is 5 vol. % to 80 vol. %.
5. The optoelectronic device according to claim 1 , 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.
6. The optoelectronic device according to claim 2 , 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.
7. The optoelectronic device according to claim 1 , wherein for the organic molecule the structure of Formula 1-1 has a structure of Formula II:
where #, Z and R have the aforestated meanings.
8. The optoelectronic device according to claim 1 , wherein for the organic molecule the structure of Formula I-1 has a structure of Formula III:
where # and R have the aforestated meanings.
9. The optoelectronic device according to claim 1 , wherein for the organic molecule X of the structure of Formula I is CN.
10. The optoelectronic device according to claim 1 , wherein for the organic molecule X of the structure of Formula I is CF 3 .
11. The optoelectronic device according to claim 1 , wherein for the organic molecule the radical R′ of the structure of Formula I is a hydrogen atom.
12. The optoelectronic device according to claim 1 , wherein for the organic molecule:
R′=selected from the group consisting of H, N(R 4 ) 2 , OR 4 , a linear alkyl or alkoxy group having 1 to 40 C atoms and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, it being possible for this group to be substituted in each case by one or more radicals R 4 , and an aromatic hydrocarbon ring system having 6 to 60 aromatic ring atoms, wherein the aromatic ring system is optionally substituted in each case by one or more radicals R 4 ;
R″=selected from the group consisting of N(R 4 ) 2 , OR 4 , a linear alkyl or alkoxy group having 1 to 40 C atoms and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, it being possible for this group to be substituted in each case by one or more radicals R 4 , and-an aromatic hydrocarbon ring system having 6 to 60 aromatic ring atoms, wherein the aromatic ring system is optionally substituted by one or more radicals R 4 .
13. The optoelectronic device according to claim 12 , 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.