ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention pertains to an organic molecule for use in optoelectronic devices. The organic molecule has a first chemical moiety with a structure of Formula I

##STR00001##

and a second chemical moiety with a structure according to Formula II

##STR00002## wherein the first chemical moiety is linked to the second chemical moiety via a single bond; # is the binding site of the first chemical moiety to the second chemical moiety; exactly one group selected from R.sup.a, R.sup.b, and R.sup.c is the binding site of a single bond linking the second chemical moiety to the first chemical moiety; m is 0 or 1, n is 0 or 1, and m+n=1; and wherein at least one pair of adjacent groups R.sup.I and R.sup.II, R.sup.II and R.sup.III, R.sup.III and R.sup.IV, R.sup.V and R.sup.VI, R.sup.VI and R.sup.VII, R.sup.VII and R.sup.VIII, R.sup.IX and R.sup.X, R.sup.X and R.sup.XI, R.sup.XI and R.sup.XII, R.sup.XII and R.sup.XIII, R.sup.XIV and R.sup.XV, R.sup.XV and R.sup.XVI, R.sup.XVI and R.sup.XVII, or R.sup.XVII and R.sup.XVIII forms an aromatic ring system which is fused to the adjacent benzene ring a, b, c or d of Formula I and which is optionally substituted with one or more substituent R.sup.9.

Claims

1.-15. (canceled)

16. An organic molecule, comprising: a first chemical moiety represented by Formula I, ##STR00245## and a second chemical moiety represented by Formula II, ##STR00246## wherein the first chemical moiety is linked to the second chemical moiety via a single bond; # is a binding site of the first chemical moiety to the second chemical moiety; m is 0 or 1, n is 0 or 1, and m+n=1; R.sup.a is a binding site of the single bond linking the second chemical moiety to the first chemical moiety, or is R.sup.A; R.sup.b is the binding site of the single bond linking the second chemical moiety to the first chemical moiety, or is R.sup.B; R.sup.c is the binding site of the single bond linking the second chemical moiety to the first chemical moiety, or is R.sup.X; R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, R.sup.X, R.sup.XI, R.sup.XII, R.sup.XIII, R.sup.XIV, R.sup.XV, R.sup.XVI, R.sup.XVII, and R.sup.XVIII are each independently selected from the group consisting of: hydrogen; deuterium; N(R.sup.9).sub.2; OR.sup.9; SR.sup.9; Si(R.sup.9).sub.3; B(OR.sup.9).sub.2; OSO.sub.2R.sup.9; CF.sub.3; CN; F; Cl; Br; I; C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.9 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.9CCR.sup.9, CC, Si(R.sup.9).sub.2, Ge(R.sup.9).sub.2, Sn(R.sup.9).sub.2, CO, CS, CSe, CNR.sup.9, P(O)(R.sup.9), SO, SO.sub.2, NR.sup.9, O, S or CONR.sup.9; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.9 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.9CCR.sup.9, CC, Si(R.sup.9).sub.2, Ge(R.sup.9).sub.2, Sn(R.sup.9).sub.2, CO, CS, CSe, CNR.sup.9, P(O)(R.sup.9), SO, SO.sub.2, NR.sup.9, O, S or CONR.sup.9; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.9 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.9CCR.sup.9, CC, Si(R.sup.9).sub.2, Ge(R.sup.9).sub.2, Sn(R.sup.9).sub.2, CO, CS, CSe, CNR.sup.9, P(O)(R.sup.9), SO, SO.sub.2, NR.sup.9, O, S or CONR.sup.9; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.9 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.9CCR.sup.9, CC, Si(R.sup.9).sub.2, Ge(R.sup.9).sub.2, Sn(R.sup.9).sub.2, CO, CS, CSe, CNR.sup.9, P(O)(R.sup.9), SO, SO.sub.2, NR.sup.9, O, S or CONR.sup.9; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.9 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.9CCR.sup.9, CC, Si(R.sup.9).sub.2, Ge(R.sup.9).sub.2, Sn(R.sup.9).sub.2, CO, CS, CSe, CNR.sup.9, P(O)(R.sup.9), SO, SO.sub.2, NR.sup.9, O, S or CONR.sup.9; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.9; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.9; wherein at least one pair of adjacent groups selected from the group of pairs consisting of R.sup.I and R.sup.II, R.sup.II and R.sup.III, R.sup.III and R.sup.IV, R.sup.V and R.sup.VI, R.sup.VI and R.sup.VII, R.sup.VII and R.sup.VIII, R.sup.IX and R.sup.X, R.sup.X and R.sup.XI, R.sup.XI and R.sup.XII, R.sup.XII and R.sup.XIII, R.sup.XIV and R.sup.XV, R.sup.XV and R.sup.XVI, R.sup.XVI and R.sup.XVII, and R.sup.XVII and R.sup.XVIII forms an aromatic ring system which is fused to a corresponding adjacent benzene ring a, b, c or d, and which is optionally substituted with one or more substituents R.sup.9; and wherein adjacent groups R.sup.I and R.sup.XVIII and/or adjacent groups R.sup.VIII and R.sup.IX optionally form a group Z.sup.1, which is at each occurrence independently selected from the group consisting of: a direct bond, CR.sup.9R.sup.10, CCR.sup.9R.sup.10, CO, CNR.sup.9, NR.sup.9, O, SiR.sup.9R.sup.10, S, S(O), and S(O).sub.2; R.sup.A, R.sup.B, R.sup.X, and R.sup.1 to R.sup.8 are independently selected from the group consisting of: hydrogen; deuterium; N(R.sup.11).sub.2; OR.sup.11; SR.sup.11; Si(R.sup.11).sub.3; B(OR.sup.11).sub.2; OSO.sub.2R.sup.11; CF.sub.3; CN; F; Cl; Br; I; C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.11 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.11CCR.sup.11, CC, Si(R.sup.11).sub.2, Ge(R.sup.11).sub.2, Sn(R.sup.11).sub.2, CO, CS, CSe, CNR.sup.11, P(O)(R.sup.11), SO, SO.sub.2, NR.sup.11, O, S or CONR.sup.11; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.11 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.11CCR.sup.11, CC, Si(R.sup.11).sub.2, Ge(R.sup.11).sub.2, Sn(R.sup.11).sub.2, CO, CS, CSe, CNR.sup.11, P(O)(R.sup.11), SO, SO.sub.2, NR.sup.11, O, S or CONR.sup.11; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.11 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.11CCR.sup.11, CC, Si(R.sup.11).sub.2, Ge(R.sup.11).sub.2, Sn(R.sub.11).sub.2, CO, CS, CSe, CNR.sup.11, P(O)(R.sup.11), SO, SO.sub.2, NR.sup.11, O, S or CONR.sup.11; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.11 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.11CCR.sup.11, CC, Si(R.sup.11).sub.2, Ge(R.sup.11).sub.2, Sn(R.sup.11).sub.2, CO, CS, CSe, CNR.sup.11, P(O)(R.sup.11), SO, SO.sub.2, NR.sup.11, O, S or CONR.sup.11; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.11 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.11CCR.sup.11, CC, Si(R.sup.11).sub.2, Ge(R.sup.11).sub.2, Sn(R.sup.11).sub.2, CO, CS, CSe, CNR.sup.11, P(O)(R.sup.11), SO, SO.sub.2, NR.sup.11, O, S or CONR.sup.11; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.11; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.11; wherein adjacent groups R.sup.2 and R.sup.3 and/or adjacent groups R.sup.X and R.sup.7 optionally form a group Z.sup.2, which is at each occurrence independently selected from the group consisting of: CR.sup.12R.sup.13, CCR.sup.12R.sup.13, CO, CNR.sup.12, NR.sup.12, O, SiR.sup.12R.sup.13, S, S(O) and S(O).sub.2; wherein, optionally, one or more pairs of adjacent groups selected from the group of pairs consisting of R.sup.1 and R.sup.2, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, R.sup.6 and R.sup.7, R.sup.7 and R.sup.8, R.sup.8 and R.sup.X, R.sup.X and R.sup.B, R.sup.B and R.sup.A, and R.sup.A and R.sup.1 form an aromatic or aliphatic, carbo- or heterocyclic ring system which is fused to a corresponding adjacent benzene ring e or f, which is optionally substituted with one or more substituents R.sup.11; R.sup.12 and R.sup.13 are at each occurrence independently selected from the group consisting of: hydrogen; deuterium; N(R.sup.14).sub.2; OR.sup.14; SR.sup.14; Si(R.sup.14).sub.3; B(OR.sup.11).sub.2; OSO.sub.2R.sup.14; CF.sub.3; CN; F; Cl; Br; I; C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.14 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.14CCR.sup.14, CC, Si(R.sup.14).sub.2, Ge(R.sup.14).sub.2, Sn(R.sup.14).sub.2, CO, CS, CSe, CNR.sup.14, P(O)(R.sup.14), SO, SO.sub.2, NR.sup.14, O, S or CONR.sup.14; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.14 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.14CCR.sup.14, CC, Si(R.sup.14).sub.2, Ge(R.sup.14).sub.2, Sn(R.sup.14).sub.2, CO, CS, CSe, CNR.sup.14, P(O)(R.sup.14), SO, SO.sub.2, NR.sup.14, O, S or CONR.sup.14; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.14 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.14CCR.sup.14, CC, Si(R.sup.14).sub.2, Ge(R.sup.14).sub.2, Sn(R.sup.14).sub.2, CO, CS, CSe, CNR.sup.14, P(O)(R.sup.14), SO, SO.sub.2, NR.sup.14, O, S or CONR.sup.14; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.14 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.14CCR.sup.14, CC, Si(R.sup.14).sub.2, Ge(R.sup.14).sub.2, Sn(R.sup.14).sub.2, CO, CS, CSe, CNR.sup.14, P(O)(R.sup.14), SO, SO.sub.2, NR.sup.14, O, S or CONR.sup.14; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.14 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.14CCR.sup.14, CC, Si(R.sup.14).sub.2, Ge(R.sup.14).sub.2, Sn(R.sup.14).sub.2, CO, CS, CSe, CNR.sup.14, P(O)(R.sup.14), SO, SO.sub.2, NR.sup.14, O, S or CONR.sup.14; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.14; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.14; wherein, optionally, R.sup.12 and R.sup.13 form an aliphatic or aromatic carbo- or heterocyclic ring system with 5 to 30 ring atoms, of which 1 to 3 atoms optionally are a heteroatom independently selected from the group consisting of N, O, and S; R.sup.9, R.sup.10, R.sup.11, and R.sup.14 are at each occurrence independently selected from the group consisting of: hydrogen; deuterium; OPh; SPh; CF.sub.3; CN; F; Si(C.sub.1-C.sub.5-alkyl).sub.3; Si(Ph).sub.3; C.sub.1-C.sub.5-alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); and wherein exactly one group selected from the group consisting of R.sup.a, R.sup.b, and R.sup.c is the binding site of the single bond linking the second chemical moiety to the first chemical moiety.

17. The organic molecule according to claim 16, wherein R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, R.sup.X, R.sup.XI, R.sup.XII, R.sup.XIII, R.sup.XIV, R.sup.XV, R.sup.XVI, R.sup.XVII, and R.sup.XVIII are each independently selected from the group consisting of: hydrogen; deuterium; Me; .sup.iPr; Bu; CN; CF.sub.3; SiMe.sub.3; SiPh.sub.3; Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, and N(Ph).sub.2; wherein at least one pair of adjacent groups selected from the group of pairs consisting of R.sup.I and R.sup.II, R.sup.II and R.sup.III, R.sup.III and R.sup.IV, R.sup.V and R.sup.VI, R.sup.VI and R.sup.VII, and R.sup.VII and R.sup.VIII forms an aromatic ring system which is fused to a respective adjacent benzene ring a or b to form a fused ring system, and which is optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; and wherein a total number of ring-forming atoms in the fused ring system is 9 to 30; wherein each pair of adjacent groups R.sup.IX and R.sup.X, R.sup.X and R.sup.XI, R.sup.XI and R.sup.XII, R.sup.XII and R.sup.XIII, R.sup.XIV and R.sup.XV, R.sup.XV and R.sup.XVI, R.sup.XVI and R.sup.XVII, and R.sup.XVII and R.sup.XVIII do not form an aromatic ring system which is fused to the adjacent benzene ring c or d; and wherein adjacent groups R.sup.I and R.sup.XVIII and/or adjacent groups R.sup.VIII and R.sup.IX optionally form a group Z.sup.1, which is at each occurrence a direct bond.

18. The organic molecule according to claim 16, wherein: at least one pair of adjacent groups selected from the group of pairs consisting of R.sup.I and R.sup.II, R.sup.II and R.sup.III, and R.sup.III and R.sup.IV forms a first aromatic ring system which is fused to the adjacent benzene ring a to form a first fused ring system; and at least one pair of adjacent groups selected from the group of pairs consisting of R.sup.V and R.sup.VI, R.sup.VI and R.sup.VII, and R.sup.VII and R.sup.VIII forms a second aromatic ring system which is fused to the adjacent benzene ring b to form a second fused ring system; wherein the first and second aromatic ring systems are identical and optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; wherein a total number of ring-forming atoms in each of the first and second fused ring systems is 9 to 30; wherein each pair of adjacent groups R.sup.IX and R.sup.X, R.sup.X and R.sup.XI, R.sup.XI and R.sup.XII, R.sup.XII and R.sup.XIII, R.sup.XIV and R.sup.XV, R.sup.XV and R.sup.XVI, R.sup.XVI and R.sup.XVII, and R.sup.XVII and R.sup.XVIII do not form an aromatic ring system which is fused to the adjacent benzene ring c or d; and wherein adjacent groups R.sup.I and R.sup.XVIII and/or adjacent groups R.sup.VIII and R.sup.IX optionally form a group Z.sup.1, which is at each occurrence a direct bond.

19. The organic molecule according to claim 16, wherein R.sup.A, R.sup.B, R.sup.X, and R.sup.1 to R.sup.8 are each independently selected from the group consisting of: hydrogen; deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; wherein adjacent groups R.sup.2 and R.sup.3 and/or adjacent groups R.sup.X and R.sup.7 optionally form a group Z.sup.2, which is at each occurrence independently selected from the group consisting of: CR.sup.12R.sup.13, NR.sup.12, O, and S; wherein, optionally, one or more pair of adjacent groups selected from the group of pairs consisting of R.sup.1 and R.sup.2, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, R.sup.6 and R.sup.7, R.sup.2 and R.sup.8, R.sup.8 and R.sup.X, R.sup.X and R.sup.B, R.sup.B and R.sup.A, and R.sup.A and R.sup.1 form an additional aliphatic or aromatic, carbocyclic or heterocyclic ring system which is fused to the adjacent benzene ring e or f to form a fused ring system, and optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, and CF.sub.3; and wherein a total number of ring-forming atoms in the fused ring system is 9 to 30 ring atoms, of which 1 to 3 atoms optionally are heteroatoms independently selected from the group consisting of N, O, and S.

20. The organic molecule according to claim 16, wherein adjacent groups R.sup.2 and R.sup.3 and/or adjacent groups R.sup.X and R.sup.7 form the group Z.sup.2, and R.sup.12 and R.sup.13 are at each occurrence independently selected from the group consisting of: hydrogen; deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, and wherein, optionally, R.sup.12 and R.sup.13 form an aliphatic or aromatic, carbocyclic ring system with 5 to 30 carbon atoms.

21. The organic molecule according to claim 16, wherein the first chemical moiety is represented by any of Formula I-a, I-b, I-c, I-d, I-e, I-f, I-g, I-h, I-i, I-j, I-k, I-m, I-n, I-o, I-p, I-q, I-r, I-s, I-t, I-u, I-v, I-w, I-x, or I-y: ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## wherein R.sup.9 is at each occurrence independently selected from the group consisting of: deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph.

22. The organic molecule according to claim 21, wherein the first chemical moiety is represented by any of Formula I-a, I-d, I-f, I-n, I-q, or I-s, and wherein R.sup.9 is at each occurrence hydrogen or deuterium.

23. The organic molecule according to claim 16, wherein the second chemical moiety is represented by any of Formula II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-6, II-b-7, II-b-8, II-b-9, II-b-10, II-b-11, II-b-12, or II-b-13: ##STR00253## ##STR00254## ##STR00255## ##STR00256## wherein, the dashed line indicates the single bond linking the second chemical moiety to the first chemical moiety; X.sup.1 is selected from the group consisting of C(R.sup.17).sub.2, NR.sup.15, O, and S; R.sup.15, R.sup.16, and R.sup.17 are at each occurrence independently selected from the group consisting of: hydrogen; deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; wherein two or more adjacent groups R.sup.16 optionally form an additional aliphatic or aromatic, carbocyclic or heterocyclic ring system which is fused to the structure according to any of Formulas II-a-4, II-a-5, II-a-6 and II-a-7 to form a fused ring system; wherein, a total number of ring-forming atoms in the fused ring system of the second chemical moiety represented by Formula II-a-4, II-a-5, II-a-6, or II-a-7 is 16 to 30, of which 1 to 3 atoms optionally are heteroatoms independently selected from the group consisting of N, O, and S; wherein the optionally formed additional ring system is optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; and wherein, optionally, two substituents R.sup.17 form an aliphatic or aromatic, carbocyclic ring system with 5 to 30 carbon atoms, which optionally are substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; .sup.iPr; .sup.tBu; CN; CF.sub.3; and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph.

24. An optoelectronic device, comprising the organic molecule according to claim 16 as a luminescent emitter.

25. The optoelectronic device according to claim 24, wherein the optoelectronic device is at least one selected from the group consisting of: organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

26. A composition, comprising: (a) the organic molecule according to claim 16, in the form of an emitter and/or a host, and (b) an emitter and/or host material, which differs from the organic molecule, and (c) optionally, a dye and/or a solvent.

27. An optoelectronic device, comprising the composition according to claim 26.

28. The optoelectronic device according to claim 27, wherein the device is at least one selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

29. The optoelectronic device according to claim 24, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is on the substrate, and a light-emitting layer between the anode and the cathode and comprising the organic molecule.

30. A method for producing an optoelectronic device, the method comprising depositing the organic molecule according to claim 16 by a vacuum evaporation method and/or from a solution.

31. The optoelectronic device according to claim 27, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is on the substrate, and a light-emitting layer between the anode and the cathode and comprising the composition.

32. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 26 by a vacuum evaporation method and/or from a solution.

Description

EXAMPLES

General Synthesis Scheme

[0433] The general synthesis scheme provides a synthesis scheme for organic molecules according to the invention.

##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020##

General Procedure for Synthesis:

Procedure 1

[0434] Under N.sub.2 atmosphere, a two-necked flask is charged with 1,3-dibromo-5-chlorobenzene [81067-41-6] (1.0 equiv.), an arylamine E1 (2.2 equiv.), Pd.sub.2(dba).sub.3 [51364-51-3] (0.01 equiv.), and sodium tert-butoxide [865-48-5] (4.0 equiv.). Dry toluene (5 mL/mmol of 1,3-dibromo-5-chlorobenzene) and tri-tert-butylphosphine [13716-12-6] (0.08 equiv.) are added and the resulting suspension is degassed for 10 min (nitrogen sparging). Subsequently, the mixture is heated at 90 C. until completion (usually 10-16 h). After cooling down to room temperature (rt), water is added, the phases separated, the aqueous layer extracted with ethyl acetate and the combined organic layers dried over MgSO.sub.4, filtered and concentrated. The crude product is purified with column chromatography or recrystallization to obtain the corresponding product P1 as a solid.

Procedure 2

[0435] Under N2 atmosphere, a two-necked flask is charged with P1 (1.0 equiv.), an aryl bromide E2 (2.2 equiv.), Pd.sub.2(dba).sub.3 [51364-51-3] (0.02 equiv.), and sodium tert-butoxide [865-48-5] (2.3 equiv.). Dry toluene (16 mL/mmol of P1) and tri-tert-butylphosphine [131274-22-1] (0.08 equiv.) are added and the resulting suspension degassed for 10 min (nitrogen sparging). Subsequently, the mixture is heated at 110 C. until completion (usually 10-24 h). After cooling down to room temperature (rt), water is added, the phases separated, the aqueous layer extracted with ethyl acetate and the combined organic layers dried over MgSO.sub.4, filtered and concentrated. The crude product is purified with column chromatography or recrystallization to obtain the corresponding product P2 as a solid.

Procedure 3

[0436] Under nitrogen atmosphere, in a flame-dried two-necked flask, aryl chloride P2 (1.0 equiv.) is dissolved in degassed tert-butylbenzene. At 20 C., a solution of ted-butyllithium (1.9 M in pentane [594-19-4] (3.3 equiv.) is added dropwise. Subsequently, the mixture is stirred at 40 C. until completion of the lithiation (2-3 h). At 0 C., trimethyl borate [121-43-7] (6.0 equiv.) is injected slowly and stirring is continued at 20 C. until completion of the borylation (1-2 h). Subsequently, water is added and the resulting biphasic mixture stirred at 20 C. for 15 min. Ethyl acetate is added, the phases separated, and the combined organic layers dried over MgSO.sub.4, filtered and concentrated. The crude product is purified by recrystallization to obtain the corresponding boronic acid P3 as a solid.

Procedure 4

[0437] Under N.sub.2 atmosphere, a two-necked flask is charged with the boronic acid P3 (1.0 equiv.). Dry chlorobenzene is added, followed by aluminum chloride [7446-70-0] (10 equiv.) and N,N-diisopropylethylamine (DIPEA) [7087-68-5] (10 equiv.). The resulting mixture is heated at 120 C. until completion of the reaction (1-2 h). After cooling down to rt, the reaction is quenched with ice water. Subsequently, the phases are separated, and the aqueous layer extracted with dichloromethane. The combined organic layers are dried over MgSO.sub.4, filtered and concentrated. The residue is purified by filtration over a plug of silica, followed by precipitation from dichloromethane solution through addition of acetonitrile. The desired material P4, was obtained as a solid.

Procedure 5

[0438] Under N.sub.2 atmosphere, a two-necked flask is charged with P4 (1.0 equiv.), bis(pinacolato)diboron [73183-34-3] (5.0 equiv.), Pd.sub.2(dba).sub.3 [51364-51-3] (0.02 equiv.), X-Phos [564483-18-7] (0.08 equiv.), and potassium acetate [127-08-2] (7.5 equiv.). Dry dioxane (20 mL/mmol of P4) is added and the resulting mixture degassed for 10 min (nitrogen sparging). Subsequently, the mixture is heated at 100 C. for 24 h. After cooling down to room temperature (rt), dichloromethane and water are added, the phases separated, the aqueous layer extracted with dichloromethane. The combined organic layers are stirred at rt with MgSO.sub.4/Celite (kieselgur)/charcoal for 10 min, filtered and concentrated. The crude product is used for further conversion without purification. The desired boronic ester P5 is obtained as a solid.

Procedure 6

[0439] Under N.sub.2 atmosphere, a two-necked flask is charged with P5 (1.0 equiv.), a heteroaryl bromide E3, E4 or E5 (4.0 equiv.), Pd(PPha).sub.4 [14221-01-3] (0.1 equiv.) and potassium carbonate [584-08-7] (3.0 equiv.). A mixture of DMF and water (10:1 by volume, 60 mL/mmol of P5) is added and the resulting mixture degassed for 15 min (nitrogen sparging). Subsequently, the mixture is heated at 150 C. for 4-6 h. After cooling down to room temperature (rt), the mixture is poured into water. The precipitated solid was filtered off and rinsed with ethanol. The crude product is purified by recrystallization to obtain the corresponding product M1, M2 or M3 as a solid.

Cyclic Voltammetry

[0440] Cyclic voltammograms are measured from solutions having concentration of 10.sup.3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp.sub.2/FeCp.sub.2.sup.+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).

Density Functional Theory Calculation

[0441] Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and an m4-grid for numerical integration were used. The Turbomole program package was used for all calculations.

Photophysical Measurements

Sample Pretreatment: Spin-Coating

[0442] Apparatus: Spin150, SPS euro.

[0443] The sample concentration is 0.2 mg/ml, dissolved in Toluene/DCM as suitable solvent.

[0444] Program: 7-30 sec. at 2000 U/min. After coating, the films are tried at 70 C. for 1 min.

Absorption Measurements

[0445] A Thermo Scientific Evolution 201 UV-Visible Spectrophotometer is used to determine wavelength of the absorption maximum of the sample in the wavelength region above 270 nm. This wavelength is used as excitation wavelength for photoluminescence spectral and quantum yield measurements.

[0446] Photoluminescence Spectroscopy and Phosphorescence Spectroscopy For the analysis of Phosphorescence and Photoluminescence spectroscopy a fluorescence spectrometer Fluoromax 4P from Horiba is used.

Time-Resolved PL Spectroscopy in the s-Range and ns-Range (FS5)

[0447] Time-resolved PL measurements were performed on a FS5 fluorescence spectrometer from Edinburgh Instruments. Compared to measurements on the HORIBA setup, better light gathering allows for an optimized signal to noise ratio, which favors the FS5 system especially for transient PL measurements of delayed fluorescence characteristics. As continuous light source, the spectrometer includes a 150 W xenon arc lamp and specific wavelengths may be selected by a Czemy-Turner monochromator. However, the standard measurements were instead performed using an external VPLED variable pulsed LED with an emission wavelength of 310 nm. The sample emission is directed towards a sensitive R928P photomultiplier tube (PMT), allowing the detection of single photons with a peak quantum efficiency of up to 25% in the spectral range between 200 nm to 870 nm. The detector is a temperature stabilized PMT, providing dark counts below 300 cps (counts per second). Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions is applied. By weighting the specific lifetimes .sub.i with their corresponding amplitudes A.sub.i,

[00001]${}_{\mathrm{DF}}={.Math.}_{i=1}^3\frac{A_i{}_i}{A_i}$ [0448] the delayed fluorescence lifetime T.sub.DF is determined.

Photoluminescence Quantum Yield Measurements

[0449] For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.

[0450] Emission maxima are given in nm, quantum yields m in % and CIE coordinates as x,y values.

[0451] PLQY is determined using the following protocol:

[0452] Quality assurance: Anthracene in ethanol (known concentration) is used as reference

[0453] Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength

Measurement

[0454] Quantum yields are measured for sample of films (2% by weight of the emitter in PMMA) under nitrogen atmosphere. The yield is calculated using the equation:

[00002]${}_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emitted}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\right)\right]d}{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\right)\right]d}$

[0455] wherein n.sub.photon denotes the photon count and Int. denotes the intensity. For quality assurance, anthracene in ethanol (known concentration) is used as reference.

Time-Correlated Single-Photon Counting (TCSPC)

[0456] Excited state population dynamics are determined employing Edinburgh Instruments FS5 Spectrofluoremeters, equipped with an emission monochromator, a temperature stabilized photomultiplier as detector unit and a pulsed LED (310 nm central wavelength, 910 s pulse width) as excitation source. The samples are placed in a cuvette and flushed with nitrogen during the measurements.

Full Decay Dynamics

[0457] The full excited state population decay dynamics over several orders of magnitude in time and signal intensity is achieved by carrying out TCSPC measurements in 4 time windows: 200 ns, 1 s, and 20 s, and a longer measurement spanning >80 s. The measured time curves are then processed in the following way:

[0458] A background correction is applied by determining the average signal level before excitation and subtracting.

[0459] The time axes are aligned by taking the initial rise of the main signal as reference.

[0460] The curves are scaled onto each other using overlapping measurement time regions.

[0461] The processed curves are merged to one curve.

Data Analysis

[0462] Data analysis was done using monoexponential and bi-exponential fitting of prompt fluorescence (PF) and delayed fluorescence (DF) decays separately. The ratio of delayed and prompt fluorescence (n-value) is calculated by the integration of respective photoluminescence decays in time.

[00003]$\frac{I_{\mathrm{DF}}\left(t\right)\mathrm{dt}}{I_{\mathrm{PF}}\left(t\right)\mathrm{dt}}=n$

[0463] The average excited state life time is calculated by taking the average of prompt and delayed fluorescence decay time, weighted with the respective contributions of PF and DF.

Production and Characterization of Optoelectronic Devices

[0464] Via vacuum-deposition methods, optoelectronic devices, such as OLED devices including organic molecules according to the invention can be produced. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100%, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100%.

[0465] The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50% of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80% of the initial luminance, and LT97 to the time point, at which the measured luminance decreased to 97% of the initial luminance etc.

[0466] Accelerated lifetime measurements are performed (e.g. applying increased current densities). Exemplarily LT80 values at 500 cd/m.sup.2 are determined using the following equation:

[00004]$\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{500\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$

[0467] wherein L.sub.0 denotes the initial luminance at the applied current density.

[0468] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given. FIGS. 1-2 show the data series for one OLED pixel.

HPLC-MS

[0469] This analysis is performed on an HPLC-MS by Agilent (HPLC1260 Infinity) with MS-detector

(Single Quadrupole).

[0470] For example, a typical HPLC method is as follows: a reverse phase column 3.0 mm100 mm, particle size 2.7 m from Agilent (Poroshell 120EC-C18, 3.0100 mm, 2.7 m HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at 45 C. and a typical gradient is as follows:

TABLE-US-00001 Flow rate [ml/min] Time [min] A[%] B[%] C[%] 2.1 0.0 40 50 10 2.1 1.00 40 50 10 2.1 3.50 10 65 25 2.1 6.00 10 40 50 2.1 8.00 10 10 80 2.1 11.50 10 10 80 2.1 11.51 40 50 10 2.1 12.50 40 50 10

[0471] using the following solvent mixtures (all solvents contain 0.1% (V/V) of formic acid:

TABLE-US-00002 Solvent A: H.sub.2O (10%) MeCN (90%) Solvent B: H.sub.2O (90%) MeCN (10%) Solvent C: THF (50%) MeCN (50%)

[0472] An injection volume of 2 L of a solution with a concentration of 0.5 mg/mL of the analyte is used for the measurements.

[0473] Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI +) or negative (APCI ) ionization mode or an atmospheric pressure photoionization (APPI) source.

Example 1

[0474] ##STR00021##

[0475] Example 1 was synthesized according to [0476] Procedure 1 (78% yield), wherein 3,5-di-tert-butylaniline [2380-36-1] was used as compound E1; [0477] Procedure 2 (59% yield); [0478] Procedure 3 (27% yield); [0479] Procedure 4 (59% yield); [0480] Procedure 5 (quant. yield); [0481] Procedure 6 (30% yield), wherein 2-bromobiphenyl [92-66-0] was used as compound E3.

[0482] MS (HPLC-MS): m/z (retention time)=898.0 (8.42 min).

[0483] The emission maximum of example 1 (2% by weight in PMMA) is at 474 nm, the full width at half maximum (FWHM) is 0.13 eV (23 nm), the CIE.sub.X and CIE.sub.Y coordinates are 0.12, and 0.22, respectively, and the PLQY is 64%.

Example 2

[0484] ##STR00022##

[0485] Example 2 was synthesized according to [0486] Procedure 1 (78% yield), wherein 3,5-di-tert-butylaniline [2380-36-1] was used as compound E1; [0487] Procedure 2 (59% yield); [0488] Procedure 3 (27% yield); [0489] Procedure 4 (59% yield); [0490] Procedure 5 (quant. yield); [0491] Procedure 6 (28% yield), wherein 2-bromodibenzofuran [86-76-0] was used as compound E3.

[0492] MS (HPLC-MS): m/z (retention time)=912.1 (8.51 min).

[0493] The emission maximum of example 1 (2% by weight in PMMA) is at 471 nm, the full width at half maximum (FWHM) is 0.13 eV (24 nm), the CIE.sub.X and CIE.sub.Y coordinates are 0.12, and 0.19, respectively, and the PLQY is 59%.

Additional Examples of Organic Molecules of the Invention

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FIGURES

[0495] FIG. 1 Emission spectrum of example 1 (2% by weight) in PMMA.

[0496] FIG. 2 Emission spectrum of example 2 (2% by weight) in PMMA.