Organic molecule, method for producing organic molecule, photoelectron device, and method for producing photoelectron device
By developing pure organic molecules without metal centers, the problems of limited efficiency and high cost of fluorescent devices in OLED devices are solved, and the effect of efficient light emission and reducing production costs is achieved.
Patent Information
- Application Number
- JP2024549506
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2022-02-23
- Filing Date
- 2023-02-23
- Publication Date
- 2025-03-21
AI Technical Summary
In existing OLED devices, the internal quantum efficiency of the fluorescent device is limited by 25% of the Sinret excitons and 75% of the triple exciton distribution, resulting in efficiency roll-off problems. High-valent heavy metal composites such as iridium or platinum are used for triple exciton harvesting, which is costly.
A pure organic molecule without metal center was developed with a structure of Formula A. By adjusting its structure and ligand, efficient photoluminescent performance is achieved, and production costs are reduced through appropriate ligand design.
Improves the light luminous efficiency of OLED equipment, reduces efficiency roll-off, and reduces production costs, providing a more economical and sustainable solution.
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Abstract
Description
[Technical field]
[0001] The present invention relates to purely organic molecules (dyes) without metal centres of formula A and their use as emitters in OLEDs (organic light emitting diodes) and other optoelectronic devices. [Background technology]
[0002] Optoelectronic devices are characterized in that electrical energy is converted into photons (OLED, LEEC) or the reverse process (OPV) takes place. It is important that such a process takes place as efficiently as possible. Therefore, in the field of OLEDs, it is ideal to use materials with the highest possible photoluminescence quantum yield. However, as known to those skilled in the art, it must also be taken into account that in OLEDs, 25% of singlet excitons and 75% of triplet excitons are formed. This allows a typical fluorescent emitter to achieve a maximum internal quantum yield of 25%. Similarly, the formation of long-lived non-emissive triplet states also leads to a problem of a rapid drop in efficiency at higher currents (the so-called efficiency roll-off).
[0003] To avoid such drawbacks and to use as many charge carriers as possible, the concept of triplet harvesting, known to those skilled in the art, can be used, which generally requires the use of expensive heavy atom complexes (e.g. iridium or platinum) (see, for example, MA Baldo, DF O'Brian, ME Thompson, SR Forrest, Phys. Rev. B 1999, 60, 14422 and H Yersin, Top Curr Chem 2004, 241, 1).
[0004] Yet another alternative is to use materials that exhibit thermally activated delayed fluorescence (TADF). The generated triplet excitons can be converted to singlet excitons, which can then emit photons from the excited state. A prerequisite for such thermal repopulation is then the lowest excited singlet (S 1 ) and triplet levels (T 1 ) should have a short energy distance from the nucleophile. This can be achieved, for example, using copper(I) complexes (see, for example, H. Yersin, U. Monkowius, T. Fischer, T. Hofbeck, WO 2010 / 149748 A1, 2010), but also with purely organic substances (see, for example, K. Shizu, H. Tanaka, H. Nakanotani, C. Adachi, WO 2013 / 172255 A1; H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234).
[0005] Intensive research in this field has revealed that, despite some already existing concepts for such emitter materials, there is still a great need for new materials. One of the reasons for this is the variety of application areas (screen technology, lighting, smart packaging, etc.) and production methods (vacuum, liquid or hybrid processing). In the case of liquid processing areas, attention must be paid in particular to the target solubility or insolubility with respect to special solvents, so that a layer can be subsequently deposited without further etching of the previously deposited layer (orthogonality). Besides such material properties mentioned, the availability is also relevant for commercialization. This includes not only the availability of synthesis components, but also the costs for the actual synthesis of the functional material, especially its purification. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0006] [Means for solving the problem] One aspect of the present invention provides a molecule comprising or formed from the structure of Formula A: [Chemical A] [ka] Here, n = 0 to 5, m=1 to 6, and n+m=6; R * are independent of each other, H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 , a linear alkyl group having from 1 to 40 carbon atoms, an alkoxy group or a thioalkoxy group, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms, which may be substituted with Here, one or more non-adjacent CH 2 The group is 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)(R2 ), SO, SO 2 , N.R. 2 , O, S or CONR 2 can be substituted with One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid-catalyzed crosslinking, base-catalyzed crosslinking, thermal crosslinking or UV (ultraviolet) crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O.2 R 3 , a linear alkyl group having from 1 to 40 carbon atoms, an alkoxy group or a thioalkoxy group, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 form together with each other a monocyclic or polycyclic, aliphatic ring system, D are each independently a donor group having electron donating properties and having the structure of formula I or II, [C1] [ka] [Case II] [ka] Where: o≧1, and o+p=(sum of C atoms of Ar)−1; Ar is an aromatic ring system having 5 to 60 aromatic ring atoms; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; Each R may be the same or different at each occurrence; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2, a linear alkyl group having from 1 to 40 carbon atoms, an alkoxy group or a thioalkoxy group, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group having from 1 to 40 carbon atoms, an alkoxy group or a thioalkoxy group, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0007] According to one embodiment, Ar is associated with a benzene ring, thereby giving D the structure of formula III: [Case III] [ka] Where: p=0 to 4, o=1 to 5, and o+p=5; Otherwise, the definitions provided for Formula II apply. In yet other embodiments, donor D has the structure of formula IV: [CIV] [ka] Where: A and B are independently selected from the group consisting of CRR', CR, NR, N, where there is a single or double bond between A and B, and there is a single or double bond between B and Z; Z is a direct bond or a substituted or unsubstituted C 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 An alkynylene group, an arylene group, or a combination thereof; -CRR', -C=CRR', -C=NR, -NR-, -O-, -SiRR'-, -S-, -S(O)-, -S(O) 2 -, substituted or unsubstituted C interrupted by O 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 an alkynylene or arylene group; a divalent organic linking group that contains a phenyl or substituted phenyl unit; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; each R and R' at each occurrence may be the same or different; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2, a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 is replaced by where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0008] In one embodiment, the crosslinkable unit QE is a compound selected from the group consisting of oxetanes, alkynes and azides, in particular for the Click reaction, and the following alkene derivatives: [ka]
[0009] In alternative embodiments of the invention, Z is a single covalent bond; a substituted or unsubstituted (and branched or cyclic) alkylene, alkenylene, alkynylene, arylene, and heteroarylene group; O, NR, C=CR 2 , C=NR, SiR 2 S, S(O), S(O) 2, BR, PR, P(O)R, and combinations of these units are also possible (e.g., alkylene, alkenylene, alkynylene, arylene, and heteroarylene groups interrupted by O (as well as branched or cyclic)).
[0010] In one embodiment, each D is, independently of the other, a donor group having electron donating properties and is selected from the group consisting of substituted or unsubstituted carbazole, substituted or unsubstituted indole, substituted or unsubstituted indoline, substituted or unsubstituted dihydroacridine, substituted or unsubstituted benzimidazole, substituted or unsubstituted 2,3,4,9-tetrahydrocarbazole, substituted or unsubstituted 1,2,3,4-tetrahydroquinoline, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted dihydrophenazine, substituted or unsubstituted spiro compounds.
[0011] The molecules according to the invention are those which contain the radical R * ,R',R 2 ,R 3 In particular, the introduction of R provides the possibility of realizing various properties, adjusts the solubility in various solvents, makes it easy to introduce groups for crosslinking (e.g., alkenes, alkynes, oxetanes), and can vary the acceptor strength by using electron-donating or electron-accepting substituents that can affect the emission hue of the entire molecule.
[0012] The aryl group contains 6 to 40 carbon atoms. The heteroaryl group contains 2 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of the carbon atoms and the heteroatom is at least 5. The heteroatom is in particular selected from N, O and / or S. In this case, the aryl or heteroaryl group is a simple aromatic ring (i.e. benzene), a simple heteroaromatic ring (e.g. pyridine, pyrimidine, thiophene, etc.), or a fused aryl or heteroaryl group (e.g. naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.).
[0013] In the present invention, an aromatic ring system comprises 6 to 60 carbon atoms in the ring system. In the present invention, a heteroaromatic ring system comprises 1 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5. The heteroatom is in particular selected from N, O and / or S. In the present invention, an aromatic or heteroaromatic ring system does not necessarily contain an aryl or heteroaryl group, but means a system in which the various aryl or heteroaryl groups can be interrupted by non-aromatic units (in particular less than 10% of atoms other than H), such as C, N or O atoms or carbonyl groups. For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene must be understood as aromatic ring systems in the present invention, and two or more aryl groups are replaced, for example, by a linear or cyclic alkyl group or are interrupted by a silyl group. Also, systems in which two or more aryl or heteroaryl groups are directly bonded to one another, such as biphenyl or terphenyl, are likewise intended to be aromatic or heteroaromatic ring systems.
[0014] A cyclic alkyl, alkoxy or thioalkoxy group means a monocyclic, bicyclic or polycyclic group.
[0015] In the present invention, individual H atoms or CH 2 The C group can also be substituted with the above groups. 1 -C 40Examples of alkyl groups include methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-hexyl, butyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl-, 1,1-dimethyl-n-hept-1-yl-, 1,1 -Dimethyl-n-oct-1-yl-, 1,1-dimethyl-n-dec-1-yl-, 1,1-dimethyl-n-dodec-1-yl-, 1,1-dimethyl-n-tetradec-1-yl-, 1,1-dimethyl-n-hexadec-1-yl-, 1,1-dimethyl-n-octadec-1-yl-, 1,1-diethyl-n-hex-1-yl-, 1,1-diethyl-n-hept-1-yl-, 1,1-diethyl-n-oct-1-yl-, 1,1-diethyl-n-dec-1-yl-, 1, Means radicals such as 1-diethyl-n-dodec-1-yl-, 1,1-diethyl-n-tetradec-1-yl-, 1,1-diethyl-n-hexadec-1-yl-, 1,1-diethyl-n-octadec-1-yl-, 1-(n-propyl)cyclohex-1-yl-, 1-(n-butyl)cyclohex-1-yl-, 1-(n-hexyl)cyclohex-1-yl-, 1-(n-octyl)cyclohex-1-yl- and 1-(n-decyl)cyclohex-1-yl-. Alkenyl group means, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.Alkynyl group means, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. 1 -C 40 An alkoxy group means for example methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
[0016] Aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms substituted with the above-mentioned radicals and linkable via any position on the aromatic or heteroaromatic ring are, for example, benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spiro-bifluorene, dihydrophenanthrene, dihydropyrene, tetra ... propylene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroiso-truxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenone, Anthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazineimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzo-thiazole, pyridazine, benzopyridazine, Pyrimidine, benzpyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, aza-carbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,It means radicals derived from 5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine and indolizine and benzothiadiazole.
[0017] In one embodiment of the present invention, the organic molecule has a molecular weight of 5,000 cm -1 Less than 3,000cm -1 Less than or equal to 2,000 cm -1 The lowest excited singlet (S 1 ) state and the triplet state below it (T 1 ) state and △E(S 1 -T 1 ) value.
[0018] In one embodiment of the present invention, the organic molecule has a luminescence lifetime of up to 50 μs, up to 30 μs or up to 20 μs.
[0019] In another embodiment, the organic molecule has a ΔE(S 1 -T 1 ) values and the luminescence lifetimes presented herein.
[0020] The organic molecule can optionally have at least one solubilizing group, such as at least one alkyl group, which increases the solubility of the organic molecule in a given solvent.
[0021] In one embodiment, the substituents for increasing solubility (solubilizing groups) are selected from the group consisting of: -Length is C 1 -C 30 A branched, unbranched or cyclic long alkyl chain having -Length is C 1 -C 30A branched, unbranched or cyclic long chain alkoxy chain having -Length is C 1 -C 30 and a branched, unbranched or cyclic long-chain perfluoroalkyl chain, -Short-chain polyethers with a chain length of 3 to 50 repeating units
[0022] In one embodiment of the present invention, the organic molecule has exactly two donors (D), so that the organic molecule has the structure of formula B, C or D: [Case B] [ka] [C] [ka] [chemical D] [ka] Where: n=4, R * are, independently of each other, H, deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2, a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 form together with each other a monocyclic or polycyclic, aliphatic ring system, D are each independently a donor group having electron donating properties and having the structure of formula I or II, [Chemical formula I] [ka] [Case II] [ka] Where: o≧1, and o+p=(sum of C atoms of Ar)−1; Ar is an aromatic ring system having 5 to 60 aromatic ring atoms; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; Each R may be the same or different at each occurrence; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 a linear alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl or alkynyl group having from 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R2; Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0023] According to one embodiment of the present invention, Ar is associated with a benzene ring, thereby obtaining the structure of formula III for D: [Case III] [ka] Where: p=0 to 4, o=1 to 5, and o+p=5; Otherwise, the definitions provided for Formula II apply.
[0024] In another embodiment of the present invention, donor D has the structure of formula IV: [CIV] [ka] Where: A and B are independently selected from the group consisting of CRR', CR, NR, N, where there is a single or double bond between A and B, and there is a single or double bond between B and Z; Z is a direct bond or a substituted or unsubstituted C 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 An alkynylene group, an arylene group, or a combination thereof; -CRR', -C=CRR', -C=NR, -NR-, -O-, -SiRR'-, -S-, -S(O)-, -S(O) 2 -, substituted or unsubstituted C interrupted by O 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 an alkynylene or arylene group; a divalent organic linking group that contains a phenyl- or substituted phenyl unit; where the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula B, C or D; each R and R' at each occurrence may be the same or different; H, Deuterium, F, Cl, Br, I, N(R2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 a linear alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl or alkynyl group having from 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R2; Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0025] In one embodiment, the crosslinkable unit QE is a compound selected from the group consisting of oxetanes, alkynes and azides, in particular for the Click reaction, and the following alkene derivatives: [ka]
[0026] In alternative embodiments of the invention, Z is a covalent bond or a substituted or unsubstituted (and branched or cyclic) alkylene, alkenylene, alkynylene, arylene and heteroarylene group, O, NR, C=CR 2 , C=NR, SiR 2 S, S(O), S(O) 2 , BR, PR, P(O)R, and combinations of these units are also possible (e.g., alkylene, alkenylene, alkynylene, arylene, and heteroarylene groups interrupted by O (as well as branched or cyclic)).
[0027] In one embodiment, each D is, independently of the other, a donor group having electron donating properties and is selected from the group consisting of substituted or unsubstituted carbazole, substituted or unsubstituted indole, substituted or unsubstituted indoline, substituted or unsubstituted dihydroacridine, substituted or unsubstituted benzimidazole, substituted or unsubstituted 2,3,4,9-tetrahydrocarbazole, substituted or unsubstituted 1,2,3,4-tetrahydroquinoline, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted dihydrophenazine, substituted or unsubstituted spiro compounds.
[0028] In yet another embodiment of the present invention, the organic molecule has the structure of formula E: [chemical E] [ka] Where: R" is H, deuterium, CF 3 , COOR 2 , CO(NR 2 ) 2 , Si(R 2 ) 3 , B(OR2 ) 2 , C(=O)R 2 , P(=O)(R 2 ) 2 , S(=O)R 2 , S(=O) 2 R 2 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group, or a thioalkoxy group having 1 to 40 carbon atoms, a linear alkenyl group, or an alkynyl group having 2 to 40 carbon atoms, or one or more of each of R 2 a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms which can be substituted by a radical; Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 form together with each other a monocyclic or polycyclic, aliphatic ring system, D are each independently a donor group having electron donating properties and having the structure of formula I or II, [Chemical formula I] [ka] [Case II] [ka] Where: o≧1, and o+p=(sum of C atoms of Ar)−1; Ar is an aromatic ring system having 5 to 60 aromatic ring atoms; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; Each R may be the same or different at each occurrence; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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, N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3, a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0029] According to one embodiment, Ar is associated with a benzene ring, thereby giving D the structure of formula III: [Case III] [ka] Where: p=0 to 4, o=1 to 5, and o+p=5; Otherwise, the definitions provided for Formula II apply.
[0030] In yet other embodiments, donor D has the structure of formula IV: [CIV] [ka] Where: A and B are independently selected from the group consisting of CRR', CR, NR, N, where there is a single or double bond between A and B, and there is a single or double bond between B and Z; Z is a direct bond or a substituted or unsubstituted C 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 An alkynylene group, an arylene group, or a combination thereof; -CRR', -C=CRR', -C=NR, -NR-, -O-, -SiRR'-, -S-, -S(O)-, -S(O) 2 -, substituted or unsubstituted C interrupted by O 1 -C 9 Alkylene group, C 2-C 8 Alkenylene group, C 2 -C 8 an alkynylene or arylene group; a divalent organic linking group that contains a phenyl- or substituted phenyl unit; where the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula E; each R and R' at each occurrence may be the same or different; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2, O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3, a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0031] In one embodiment, the crosslinkable unit QE is a compound selected from the group consisting of oxetanes, alkynes and azides, in particular for the Click reaction, and the following alkene derivatives: [ka]
[0032] In alternative embodiments of the invention, Z is a single covalent bond; a substituted or unsubstituted (and branched or cyclic) alkylene, alkenylene, alkynylene, arylene, and heteroarylene group; O, NR, C=CR 2 , C=NR, SiR 2 S, S(O), S(O) 2 , BR, PR, P(O)R, and combinations of these units are also possible (e.g., alkylene, alkenylene, alkynylene, arylene, and heteroarylene groups interrupted by O (as well as branched or cyclic)).
[0033] In one embodiment, each D is, independently of the other, a donor group having electron donating properties and is selected from the group consisting of substituted or unsubstituted carbazole, substituted or unsubstituted indole, substituted or unsubstituted indoline, substituted or unsubstituted dihydroacridine, substituted or unsubstituted benzimidazole, substituted or unsubstituted 2,3,4,9-tetrahydrocarbazole, substituted or unsubstituted 1,2,3,4-tetrahydroquinoline, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted dihydrophenazine, substituted or unsubstituted spiro compounds.
[0034] In yet another embodiment of the present invention, the organic molecule has the structure of formula F: [F] [ka] Where: R" is H, deuterium, CF 3 , 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 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group, or a thioalkoxy group having 1 to 40 carbon atoms, a linear alkenyl group, or an alkynyl group having 2 to 40 carbon atoms, or one or more of each of R 2 a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms which can be substituted by a radical; Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or each of them can be substituted with one or more radicals R2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 form together with each other a monocyclic or polycyclic, aliphatic ring system, D are each independently a donor group having electron donating properties and having the structure of formula I or II, [Chemical formula I] [ka] [Case II] [ka] Where: o≧1, and o+p=(sum of C atoms of Ar)−1; Ar is an aromatic ring system having 5 to 60 aromatic ring atoms; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; Each R may be the same or different at each occurrence; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is R2 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, where one or more H atoms are replaced by F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0035] According to one embodiment, Ar is associated with a benzene ring, thereby giving D the structure of formula III: [Case III] [ka] Where: p=0 to 4, o=1 to 5, and o+p=5; Otherwise, the definitions provided for Formula II apply.
[0036] In yet other embodiments, donor D has the structure of formula IV: [CIV] [ka] Where: A and B are independently selected from the group consisting of CRR', CR, NR, N, where there is a single or double bond between A and B, and there is a single or double bond between B and Z; Z is a direct bond or a substituted or unsubstituted C 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8An alkynylene group, an arylene group, or a combination thereof; -CRR', -C=CRR', -C=NR, -NR-, -O-, -SiRR'-, -S-, -S(O)-, -S(O) 2 -, substituted or unsubstituted C interrupted by O 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 an alkynylene or arylene group; a divalent organic linking group that contains a phenyl- or substituted phenyl unit; where the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula F; each R and R' in each occurrence may be the same or different; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which can be substituted by one or more radicals R2, or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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)(R3 ) 2 , S(=O)R 3 , S(=O) 2 R 3 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 are, in each case, the same or different, and are H, deuterium, F, CF3, or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, inclusive, where one or more H atoms are selected from the group consisting of F or CF 3 where two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0037] In one embodiment, the crosslinkable unit QE is a compound selected from the group consisting of oxetanes, alkynes and azides, in particular for the Click reaction, and the following alkene derivatives: [ka]
[0038] In alternative embodiments of the invention, Z is a single covalent bond; a substituted or unsubstituted (and branched or cyclic) alkylene, alkenylene, alkynylene, arylene, and heteroarylene group; O, NR, C=CR 2 , C=NR, SiR 2 S, S(O), S(O) 2 , BR, PR, P(O)R, and combinations of these units are also possible (e.g., alkylene, alkenylene, alkynylene, arylene, and heteroarylene groups interrupted by O (as well as branched or cyclic)).
[0039] In one embodiment, each D is, independently of the other, a donor group having electron donating properties and is selected from the group consisting of substituted or unsubstituted carbazole, substituted or unsubstituted indole, substituted or unsubstituted indoline, substituted or unsubstituted dihydroacridine, substituted or unsubstituted benzimidazole, substituted or unsubstituted 2,3,4,9-tetrahydrocarbazole, substituted or unsubstituted 1,2,3,4-tetrahydroquinoline, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted dihydrophenazine, substituted or unsubstituted spiro compounds.
[0040] In yet another embodiment of the present invention, the donor group D has the structure of formula V: [CV] [ka] Where: Z is a direct bond or a substituted or unsubstituted C 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 An alkynylene group, an arylene group, or a combination thereof; -CRR', -C=CRR', -C=NR, -NR-, -O-, -SiRR'-, -S-, -S(O)-, -S(O) 2 -, substituted or unsubstituted C interrupted by O 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 an alkynylene or arylene group; a divalent organic linking group that contains a phenyl- or substituted phenyl unit; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; each R and R' at each occurrence may be the same or different; H, Deuterium, F, Cl, Br, I, N(R2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, wherein one or more H atoms are selected from the group consisting of F or CF 3 and two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0041] In one embodiment, the crosslinkable unit QE is a compound selected from the group consisting of oxetanes, alkynes and azides for the Click reaction, and the following alkene derivatives: [ka]
[0042] In alternative embodiments of the invention, Z is a single covalent bond; a substituted or unsubstituted (and branched or cyclic) alkylene, alkenylene, alkynylene, arylene, and heteroarylene group; O, NR, C=CR 2 , C=NR, SiR 2 S, S(O), S(O) 2 , BR, PR, P(O)R, and combinations of these units are also possible (e.g., alkylene, alkenylene, alkynylene, arylene, and heteroarylene groups interrupted by O (as well as branched or cyclic)).
[0043] In yet another embodiment of the present invention, the donor group D has the structure of formula VI: [Chemical formula VI] [ka] Where: The wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; Each R may be the same or different at each occurrence; H, Deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 2, a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation; two or more of the R and R' substituents together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R2 may be the same or different in each occurrence, H, Deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 , O.S.O. 2 R 3 , a linear alkyl group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having 3 to 40 carbon atoms and which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 OR NO 2 or each of them can be substituted with one or more radicals R 3or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, wherein one or more H atoms are selected from the group consisting of F or CF 3 and two or more substituents R 3 may together form a monocyclic or polycyclic, aliphatic ring system.
[0044] In one embodiment, the crosslinkable unit QE is a compound selected from the group consisting of oxetanes, alkynes and azides for the Click reaction, and the following alkene derivatives: [ka]
[0045] Examples of donors according to the present invention: [ka] [ka]
[0046] In various embodiments, the molecules according to the invention are substituted with one, two, three, four, five or six donors D.
[0047] The present invention also relates to a method for producing an organic molecule according to the invention.
[0048] In one embodiment, the method includes Cu-catalyzed or Pd-catalyzed coupling of the bromine-substituted compound to the secondary amine. [ka] [ka] wherein the definitions given for formulae A, I, and II apply and X is Cl, Br, or I.
[0049] In another embodiment, the method according to the present invention further comprises the step of substituting with at least one substituent selected from the group consisting of: -Length is C 1 -C 30 A long-chain, branched or unbranched or cyclic alkyl chain having -Length is C 1 -C 30 A long chain, branched or unbranched or cyclic alkoxy chain having -Length is C 1 -C 30 and a branched, unbranched or cyclic perfluoroalkyl chain, -Short-chain polyethers with a chain length of 3 to 50 repeating units
[0050] In yet another embodiment, the method according to the invention comprises the steps of: *with a crosslinkable unit that is crosslinkable by acid catalyzed crosslinking, base catalyzed crosslinking, thermal crosslinking or UV crosslinking in the presence or absence of a photoinitiator or by microwave radiation, which are selected from the group consisting of: -Oxetanes, azides and alkynes for click reactions and the following alkene derivatives: [ka]
[0051] The present invention also relates to the use of the molecules according to the invention as emitters or absorbers in optoelectronic devices produced by a vacuum evaporation process or from a solution, said optoelectronic devices being in particular selected from the group consisting of: -Organic Light Emitting Diode (OLED) -Light-emitting electrochemical cells -OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside -Organic solar cells -Organic field effect transistor -Organic laser -Down-conversion element
[0052] In one embodiment, the proportion of organic molecules in the emitter or absorber is 1% to 99%, in particular in organic light emitting devices, especially OLEDs, the proportion of organic molecules as emitters is 5% to 80%. In another embodiment, the proportion of organic molecules in the emitter or absorber is 100%.
[0053] The present invention also relates to optoelectronic devices comprising the organic molecules according to the invention, said optoelectronic devices including in particular organic light-emitting devices, organic diodes, organic solar cells, organic transistors, organic light-emitting diodes, light-emitting electrochemical cells, organic field effect transistors and organic lasers.
[0054] In one embodiment of the optoelectronic device according to the invention, the compound according to the invention is used as luminescent material in the light-emitting layer, either as a pure layer or in combination with a matrix material.
[0055] In another embodiment, in an optical light emitting device, in particular an OLED, the proportion of organic molecules according to the invention as luminescent material in the emitting layer is between 5% and 80%.In one embodiment of an optoelectronic device according to the invention, the emitting layer is deposited on a substrate, in particular an anode and a cathode are deposited on a substrate and the emitting layer is deposited between the anode and the cathode.
[0056] The light-emitting layer entirely comprises organic molecules according to the invention in a concentration of 100%, an anode and a cathode are deposited on a substrate, and the light-emitting layer is deposited between the anode and the cathode.
[0057] In one embodiment, the light-emitting layer contains, in addition to the organic molecules according to the present invention, triplets (T 1 ) energy levels and singlet (S 1 ) energy level of organic molecules is triplet (T 1 ) energy levels and singlet (S 1 ) energy level above the host material.
[0058] In one embodiment of the optoelectronic device according to the invention, a hole injection layer and an electron injection layer are deposited between the anode and the cathode, a hole transport layer and an electron transport layer are deposited between the hole injection layer and the electron injection layer, and an emissive layer is deposited between the hole transport layer and the electron transport layer.
[0059] In yet another embodiment of the present invention, an optoelectronic device comprises a substrate, an anode, a cathode, at least one hole injection layer and at least one electron injection layer, at least one hole transport layer and at least one electron transport layer, at least one light-emitting layer, organic molecules according to the present invention, and a triplet (T 1 ) energy levels and singlet (S 1 ) energy level of organic molecules is triplet (T 1 ) energy levels and singlet (S1 ) energy level of the light-emitting layer, a positive electrode and a negative electrode are deposited on a substrate, a hole injection layer and an electron injection layer are deposited between the positive electrode and the negative electrode, a hole transport layer and an electron transport layer are deposited between the hole injection layer and the electron injection layer, and an emitting layer is deposited between the hole transport layer and the electron transport layer.
[0060] The present invention also provides a light-emitting material, comprising an organic molecule according to the present invention and a host material, the triplet (T 1 ) energy levels and singlet (S 1 ) energy level of the organic molecule 1 ) energy levels and singlet (S 1 ) energy level, the luminescent material emits fluorescence or thermally activated delayed fluorescence, and the lowest excited singlet (S 1 ) and the triplet (T1) below it, ΔE(S 1 -T 1 ) value is 3,000 cm -1 is less than.
[0061] The present invention also relates to a method for producing an optoelectronic device using the organic molecules according to the invention.
[0062] In one embodiment of such a method according to the invention, the organic molecules according to the invention are deposited by a carrier, said deposition being carried out in particular wet-chemically, by colloidal suspension or by sublimation.
[0063] In addition, in the method for producing an optoelectronic element according to the present invention, at least one layer of the optoelectronic element is -Coated in a sublimation process, -Coated in the OVPD (organic vapor phase deposition) process, -Carrier gas sublimation coated and / or - Produced from solution or by printing processes.
[0064] The invention also relates to a method for modifying the emission and / or absorption properties of an electronic component, characterized in that an organic molecule according to the invention is incorporated into a matrix material for conducting electrons or holes in an optoelectronic device.
[0065] The invention also relates to organic molecules for converting UV radiation or blue light into visible light, in particular green, yellow or red light (down-conversion), in particular for the use of organic molecules in optoelectronic devices.
[0066] Example General synthesis route: [ka] [ka]
[0067] where the definitions given for formulae A, I and II apply and X is Cl, Br or I.
[0068] In the case of direct attachment of an amine, the synthesis can occur via palladium- or copper-catalyzed, or mediated reactions of single or multiply brominated disulfones with secondary amines. In the case where the donor is attached via an aryl group, the synthesis can occur via palladium-, nickel-, or copper-catalyzed, or mediated reactions of single or multiply brominated disulfones with secondary amines.
Claims
1. An organic molecule having the structure of formula A: [Chemical A] 【Chemistry 1】 Where: n=0 to 5; m=1 to 6, and n+m=6; R * are, independently of each other, H, deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that can be crosslinked by acid-catalyzed crosslinking, base-catalyzed crosslinking, thermal crosslinking or ultraviolet crosslinking in the presence or absence of a photoinitiator or by microwave radiation, two or more of the substituents R and R′ together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, wherein one or more H atoms are selected from the group consisting of F or CF 3 and two or more substituents R 3 together form a monocyclic or polycyclic, aliphatic ring system, D are each independently a donor group having electron donating properties and having the structure of formula I or II, [Chemical formula I] 【Chemistry 2】 [Chemical II] 【Chemistry 3】 Where: o≧1, and o+p=(sum of C atoms of Ar)−1; Ar is an aromatic ring system having 5 to 60 aromatic ring atoms; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; Each R may be the same or different at each occurrence; H, deuterium, F, Cl, Br, I, N(R 2 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that is crosslinkable by acid-catalyzed, base-catalyzed, thermal or UV crosslinking methods in the presence or absence of a photoinitiator or by microwave radiation; two or more of the substituents R and R′ together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of them can be substituted with one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, wherein one or more H atoms are selected from the group consisting of F or CF 3 and two or more substituents R 3 can together form a monocyclic or polycyclic, aliphatic ring system.
2. The organic molecule of claim 1 , wherein D has the structure of Formula III: [Chemical III] 【Chemistry 4】 Where: p=0 to 4, o=1 to 5, with the proviso that o+p=5; Otherwise the definitions given in claim 1 apply.
3. 2. The organic molecule of claim 1 , wherein D has the structure of Formula IV: [Case IV] 【Chemistry 5】 Where: A and B are independently selected from the group consisting of CRR′, CR, NR, and N, where there is a single or double bond between A and B, and there is a single or double bond between B and Z; Z is a direct bond or a substituted or unsubstituted C 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 An alkynylene group, an arylene group, or a combination thereof; —CRR′, —C═CRR′, —C═NR, —NR—, —O—, —SiRR′—, —S—, —S(O)—, —S(O) 2 -, substituted or unsubstituted C interrupted by O 1 -C 9 Alkylene group, C 2 -C 8 Alkenylene group, C 2 -C 8 an alkynylene or arylene group; a divalent organic linking group that contains a phenyl- or substituted phenyl unit; wherein the wavy line indicates the position where D is attached to the aromatic backbone of a molecule of formula A; each R and R' in each occurrence may be the same or different; H, deuterium, azide (N 3 -), F, Cl, Br, I, N (R 2 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that is crosslinkable by acid-catalyzed, base-catalyzed, thermal or UV crosslinking methods in the presence or absence of a photoinitiator or by microwave radiation; two or more of the substituents R and R′ together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, wherein one or more H atoms are selected from the group consisting of F or CF 3 and two or more substituents R 3 can together form a monocyclic or polycyclic, aliphatic ring system.
4. The organic molecule is - The lowest excited singlet (S 1 ) state and the triplet (T 1 ) state and △E(S 1 -T 1 ) value is 3,000 cm -1 and / or An organic molecule according to any one of claims 1 to 3, having a luminescence lifetime of 100 μs or less.
5. 5. The organic molecule of claim 1 having the structure of formula B: [Chemical B] 【Chemistry 6】 Where: n=4, Otherwise the definitions given in claims 1 to 4 apply.
6. 5. The organic molecule of claim 1 having the structure of formula C: [C] 【Chemistry 7】 Where: n=4, Otherwise the definitions given in claims 1 to 4 apply.
7. 5. The organic molecule of claim 1 having the structure of formula D: [Chemical D] 【Chemistry 8】 Where: n=4, Otherwise the definitions given in claims 1 to 4 apply.
8. 7. The organic molecule of claim 6 having the structure of Formula E: [Chemical E] 【Chemistry 9】 Where: R" is H, deuterium, CF 3 , 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 group, an alkoxy group, or a thioalkoxy group having 1 to 40 carbon atoms, a linear alkenyl group, or an alkynyl group having 2 to 40 carbon atoms, or one or more of each of R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms which can be substituted by a radical; Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that is crosslinkable by acid-catalyzed, base-catalyzed, thermal or UV crosslinking methods in the presence or absence of a photoinitiator or by microwave radiation; two or more of the substituents R and R′ together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, wherein one or more H atoms are selected from the group consisting of F or CF 3 and two or more substituents R 3 can together form a monocyclic or polycyclic, aliphatic ring system.
9. 8. The organic molecule of claim 7 having the structure of formula F: [chemical F] 【Chemistry 10】 Where: R" is H, deuterium, CF 3 , 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 group, an alkoxy group, or a thioalkoxy group having 1 to 40 carbon atoms, a linear alkenyl group, or an alkynyl group having 2 to 40 carbon atoms, or one or more of each of R 2 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms which can be substituted by a radical; Here, one or more non-adjacent CH 2 The group is 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 , N.R. 2 , O, S or CONR 2 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 2 or one or more radicals R 2 or one or more radicals R 2 or a combination of these systems, or a crosslinkable unit QE that is crosslinkable by acid-catalyzed, base-catalyzed, thermal or UV crosslinking methods in the presence or absence of a photoinitiator or by microwave radiation; two or more of the substituents R and R′ together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 2 may be the same or different in each occurrence, H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , C.N., C.F. 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 group, an alkoxy group or a thioalkoxy group having from 1 to 40 carbon atoms, a linear alkenyl group or an alkynyl group having from 2 to 40 carbon atoms, or one or more of each of the radicals R 3 a branched or cyclic alkyl group, alkenyl group, alkynyl group, alkoxy group, or thioalkoxy group having from 3 to 40 carbon atoms, which can be substituted by Here, one or more non-adjacent CH 2 The group is 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 , N.R. 3 , O, S or CONR 3 is replaced by One or more H atoms are deuterium, F, Cl, Br, I, CN, CF 3 Or NO 2 or each of which may be substituted with one or more radicals R 3 or one or more radicals R 3 or one or more radicals R 3 or a combination of these systems, where two or more substituents R 2 together form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system; R 3 may be the same or different in each case and are H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having from 1 to 20 carbon atoms, in which one or more H atoms are replaced by F or CF3 and two or more substituents R 3 can together form a monocyclic or polycyclic, aliphatic ring system.
10. The organic molecule according to any one of claims 1 to 3, wherein D is selected from the group consisting of substituted or unsubstituted carbazole, substituted or unsubstituted indole, substituted or unsubstituted indoline, substituted or unsubstituted 2,3,4,9-tetrahydrocarbazole, substituted or unsubstituted 1,2,3,4-tetrahydroquinoline, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, substituted or unsubstituted dihydrophenazine, and substituted or unsubstituted spiro compounds.
11. 11. The organic molecule of claim 3 , wherein the electron donor group of formula IV has the structure of formula V: [Case V] 【Chemistry 11】 where R is as defined in claim 1.
12. The organic molecule of claim 11 , wherein Z is a direct bond.
13. 13. A method for the preparation of organic molecules according to any one of claims 1 to 12, characterized by a step of catalytic coupling, in particular Cu, Ni or Pd catalysed coupling, of a bromine substituted compound with a secondary amine or with an amine substituted aromatic, in particular in the latter case nickel catalysed coupling, said method being carried out in particular according to one of the following reaction schemes: 【Chemistry 12】 【Chemistry 13】 wherein the definitions given in claim 1 apply and X is Cl, Br, I.
14. The method further comprises the step of replacing the donor D, the radical R″ and / or the radical R with at least one crosslinkable unit that is crosslinkable by acid-catalyzed, base-catalyzed, thermal or UV crosslinking methods, 13. The method of claim 12, wherein the units are crosslinked in the presence or absence of a photoinitiator or by microwave radiation and are selected from the group consisting of: Oxetanes, azides and alkynes for the click reaction, and the following alkene derivatives: 【Chemistry 14】 。
15. 13. Use of an organic molecule according to any one of claims 1 to 12 as an emitter or absorber in an optoelectronic device produced by a vacuum evaporation process or from a solution.
16. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 12.
17. A method for manufacturing an optoelectronic device, in which an organic molecule according to any one of claims 1 to 12 is used.