Organic molecules for optoelectronic devices and method for producing the organic molecules

Abstract

The present invention relates to a purely organic molecule (containing no metal centres) and its use as an emitter or absorber in an optoelectronic device. According to the invention, the purely organic molecule comprises the structure of formula A: [Formula 1] JPEG2025508664000019.jpg1623...Chemical formula A Where: (Het)Ar is a conjugated organic group selected from the group consisting of unsubstituted or substituted aromatics, heteroaromatics, and conjugated double bonds fixed by cis-trans isomerization; D is a chemically attached donor group having electron donating properties, and A is a chemically attached acceptor group having electron accepting properties; A and D are bonded to adjacent atoms of (Het)Ar.

Description

[Technical field]

[0001] The present invention relates to purely organic molecules (dyes) containing no metal centres of formula A and their use as emitters in OLEDs (organic light emitting diodes) and other optoelectronic components. [Background technology]

[0002] Recently, in the display technology field, the technology based on OLEDs (organic light-emitting diodes) has been established and the first commercial products based on them are appearing. Besides screen technology, OLEDs are also suitable for flat lighting technology.

[0003] Such devices are generally realized by a layer structure mainly composed of organic materials. For a better understanding, a simplified structure is exemplarily shown in FIG. 1. The key element of such devices is the light-emitting layer, in which the molecules that emit light are generally contained in a matrix. In said layer, negative charge carriers (electrons) and positive charge carriers (holes) meet and recombine to form so-called excitons. The energy contained in the excitons is released by the emitter in the form of light, which is called electroluminescence. An overview of the functioning of OLEDs is given, for example, in Top. Curr. Chem., 2004, 241, 1, H. Yersin and in "Highly Efficient OLEDs with Phosphorescent Materials", H Yersin, Wiley-VCH, Weinheim, Germany, 2008. Summary of the Invention [Problem to be solved by the invention]

[0004] Since the first report on organic light-emitting diodes (OLEDs) (Tang et al. Appl. Phys. Lett. 1987, 51, 913), the technology has been continuously developed, especially in the field of emitter materials. The first materials based purely on organic molecules could convert up to 25% of the excitons into light, based on spin statistics, but the use of phosphorescent compounds avoids this fundamental problem, but theoretically all excitons can be converted into light. However, said materials have drawbacks, especially with regard to the cost and stability of the materials used.

[0005] For triplet emitters suitable for triplet harvesting, transition metal complexes are usually used, in which metals are selected from the third row of transition metals. These are mainly very expensive noble metals such as iridium, platinum or gold. (In this connection, see also Top. Curr. Chem., 2004, 241, 1, by H. Yersin, and Phys. Rev. B 1999, 60, 14422, by MA Baldo, DF O'Brien, ME Thompson, SR Forrest). [Means for solving the problem]

[0006] Surprisingly, the present invention, using organic molecules of formula A (dyes, emitter molecules), can significantly ameliorate or eliminate the aforementioned problems.

[0007] The organic molecules according to the invention comprise a central base unit in the form of a π-conjugated system (pi-conjugated system), i.e. an aromatic (e.g. heteroaromatic or aromatic) substituted with a functional group (donor) with electron-donating properties and with a functional group (acceptor) with electron-withdrawing properties. Both groups are located on adjacent atoms of the central base unit, i.e. ortho-positioned to each other. Due to the ortho-positioning of such groups (donor and acceptor), they must rotate relative to each other and thus be orthogonal to each other, thereby electronically separating them. Such separation can be understood, for example, with a quantum mechanical calculation of the HOMO and LUMO. The two boundary orbitals must therefore not overlap or only show a minimal overlap. The pi-conjugated system of the central base unit may be mainly part of the HOMO or LUMO.

[0008] Besides such groups (donor and acceptor), there are no other groups with an electronic influence on the pi-conjugated system (central base unit). Further substituents which are permissible are, for example, alkyl groups or other groups which have a solubility effect.

[0009] The present invention provides an organic molecule consisting of or having the structure of Formula A, which may be used in optoelectronic devices. [ka] ···Chemical formula A In formula A, each letter represents the following: (Het)Ar is a conjugated organic group selected from the group consisting of unsubstituted or substituted aromatics, heteroaromatics, and conjugated double bonds fixed by cis-trans isomerization; D is a chemically attached donor group having electron donating properties, and A is a chemically bonded acceptor group having electron-accepting properties, where A and D are bonded to immediately adjacent atoms of the conjugated organic group (Het)Ar.

[0010] 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 (T1) state below it, E(S 1 -T 1 ) value.

[0011] In one embodiment of the invention, the organic molecule has a luminescence lifetime of up to 50 μs, up to 30 μs or up to 20 μs.

[0012] In other embodiments, the organic molecule is a molecule having the E(S 1 -T 1 ) values ​​and the luminescence lifetimes presented herein.

[0013] Examples of donors include aromatics and heteroaromatics that already exhibit electron donating properties themselves and / or are substituted with electron donating groups, as well as other donors directly attached to a central pi-conjugated system (aromatic or heteroaromatic).

[0014] The donors are as follows: -O(-), -N(H)-alkyl group, -N-(alkyl group) 2 -NH 2 , -OH, -O-alkyl group, -NH(CO)-alkyl group, -O(CO)-alkyl group, -alkyl group, -phenyl group, -(CH)=C-(alkyl group) 2

[0015] Examples of acceptors include aromatics and heteroaromatics that already exhibit electron-accepting properties themselves and / or are substituted with electron-accepting groups, as well as other acceptors directly attached to a central pi-conjugated system (aromatic or heteroaromatic).

[0016] The receptors are as follows: -Halogen, -(CO)H, -(CO)-alkyl group, -(CO)O-alkyl group, -(CO)OH, -(CO)Cl, -CF3 , -CN, -S(O) 2 OH, -NH 3 (+), -N(alkyl group) 3 (+), N(O) 2

[0017] The organic molecule may optionally contain at least one solubilizing group, such as at least one alkyl group, which increases the solubility of the organic molecule in a given solvent.

[0018] 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, -Length is C 1 ~C 30 a branched or unbranched or cyclic long chain alkoxy chain, -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 repeat units.

[0019] In one embodiment of the present invention, the organic molecule has a phenyl ring as the central pi-conjugated system (Formula B). [ka] ...Chemical formula B

[0020] In another embodiment of the invention, at least one of the two substituents (i.e., donor and / or acceptor) of the central base unit contains a heteroatom X through which the substituent is bonded to the central base unit (pi-conjugated system).

[0021] The heteroatoms X are independently selected from the group consisting of N, S, P, O and Se.

[0022] In yet another embodiment of the present invention, the two substituents (i.e., donor and acceptor) are bonded to the central base unit (pi-conjugated system) via heteroatoms X (each independent of the other) selected from the group including N, S, P, O and Se.

[0023] In yet another embodiment of the invention, the organic molecule has the structure of Formula C: [ka] ...Chemical formula C At this time, NRR 1 is a donor (corresponding to D in formula A or formula B), R, R 1 are independent of each other, Hydrogen; halogen; and oxygen (-OR), nitrogen (-NR) through a direct bond or 2 ), silicon atom -(-SiR 3 a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups substituted with substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups; and Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitrile groups, and CF 3 and other commonly known donor and acceptor groups such as groups.

[0024] The radicals R and R 1 may alternatively be formed as a fused ring system.

[0025] The "oxidized" heteroatom Z(=O)n is an acceptor (corresponding to A in formula A or formula B), Z is selected from the group consisting of S and P; n is 1 or 2 to which a further radical R is attached; The radicals are, independently of one another, Hydrogen; halogen; and oxygen (-OR), nitrogen (-NR) through a direct bond or 2 ), silicon atom -(-SiR 3 a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups, having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and the like; and Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF 3 and other commonly known donor and acceptor groups such as groups.

[0026] The radical R may also optionally be formed in a fused ring system.

[0027] An example of such a receptor is SO 2 R, SO 2 (OR), S(O)R, P(O)RR', P(O)(OR)(OR'), P(O)R(OR'), SeO 2 R and Se(O)R.

[0028] In yet another embodiment of the invention, the organic molecule has the structure of Formula D: [ka] ...Chemical formula D At this time, NArAr 1 is a donor (corresponding to D in formula A or formula B), Here, Ar, Ar 1 is optionally aryl, heteroaryl (independently of each other) to which further radicals R are attached, The radicals are, independently of each other, Hydrogen; halogen; and oxygen (-OR), nitrogen (-NR) through a direct bond or 2 ), silicon atom -(-SiR 3 a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, etc., having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, etc.; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF 3 and other commonly known donor and acceptor groups such as groups.

[0029] The radical R may also optionally be formed in a fused ring system.

[0030] Ar and Ar 1 may also be condensed with each other or bonded with each other via the unit E (e.g., carbazole, phenoxazine), E is through a direct bond, or a substituted or unsubstituted alkylene group, alkenylene group, alkynylene group, arylene group, or a combination thereof; -O-, -NR-, -SiR2 -,-S-,-S(O)-,-S(O) 2 -, an alkyl group (including branched or cyclic) terminated by O, a heteroalkyl group, an aryl group, a heteroaryl group, an alkenyl group, or a phenyl group; or an organic linking group which is a substituted phenyl unit; where each R is independent of the others, Hydrogen; halogen; and oxygen (-OR), nitrogen (-NR) through a direct bond or 2 ), silicon atom -(-SiR 3 a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups and alkenyl groups having substituents such as halogen, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups and the like; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF 3 and other commonly known donor and acceptor groups such as groups.

[0031] The radical R may also optionally be formed in a fused ring system.

[0032] SO 2 Ar 2 is a receptor (chemical formula A or chemical formula B, corresponding to A), Here, Ar 2 is aryl or heteroaryl to which a further radical R is optionally attached; The radicals are, independently of one another, Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or aryl 2), silicon atom -(-SiR 3 a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups and alkenyl groups having substituents such as halogen, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups and the like; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF 3 and other commonly known donor and acceptor groups such as groups.

[0033] The radical R may also optionally be formed into a fused ring system.

[0034] Ar may also be fused to other aryl and heteroaryl groups to form larger aromatic systems (eg, phenyl, naphthyl, anthracenyl, tolyl, etc.).

[0035] In yet another embodiment of the invention, the organic molecule has the structure of Formula E: [ka] ...Chemical formula E At this time, R 1 ~R 18 are each independently of the other, Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or aryl 2 ), silicon atom -(-SiR 3 or a substituent bonded via a sulfur (-SR) atom, where the radical R corresponds to the definition given for R in formula D; The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups and alkenyl groups having substituents such as halogen, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups and the like; Optionally, further substituted and / or condensed groups, such as amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitrile groups, and CF 3 and other commonly known donor and acceptor groups such as groups.

[0036] The radical R 1 ~R 18 may also optionally be formed as a fused ring system.

[0037] According to another aspect, the present invention relates to a method for preparing the aforementioned organic molecules. In one embodiment, the method comprises the step of substituting at least one of the three groups, (Het)Ar, A and / or D (of formula A or B), with at least one substituent to increase solubility, wherein the substituent is selected from the group consisting of: -Length is C 1 ~C 30 a long-chain, branched or unbranched, or cyclic alkyl chain, -Length is C 1 ~C 30 long chain, branched or unbranched or cyclic alkoxy chains, -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 repeat units.

[0038] In yet another aspect, the present invention relates to the use of organic molecules of the type described herein as emitters or absorbers in optoelectronic devices, preferably selected from the following group: -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 transistors, -Organic lasers and -down-conversion element

[0039] The ratio of organic molecules in the emitter or absorber is 1% to 99%. In one embodiment of the present invention, the ratio of organic molecules in the emitter or absorber may be 100%.

[0040] In one embodiment, in the optical light emitting device, particularly in the OLED, the proportion of organic molecules as emitters is 5% to 80%.

[0041] In yet another aspect, the invention relates to an optoelectronic device comprising an organic molecule of the type described herein, said device may in particular be selected from the group consisting of 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.

[0042] In yet another aspect, the present invention relates to methods of fabricating optoelectronic devices using organic molecules of the type described herein.

[0043] Part of such a method may be the step of applying the organic molecules according to the invention to a carrier, the application being optionally carried out wet chemically, by colloidal suspension or by sublimation.

[0044] In yet another aspect, the present invention relates to a method for modifying the emission and / or absorption properties of an electronic device, comprising the step of incorporating an organic molecule according to the present invention into a matrix material for conducting electrons or holes in an optoelectronic device.

[0045] In yet another aspect, the present invention relates to the use of organic molecules of the type described herein in optoelectronic devices, in particular for the conversion of ultraviolet (UV) radiation or blue light into visible light, in particular green, yellow or red light (so-called down-conversion). [Brief description of the drawings]

[0046] [Figure 1] FIG. 1 illustrates generally an example of an OLED structure (the device includes at least one anode, cathode, and light-emitting layer; the thicknesses given for the layers are merely exemplary). [Diagram 2] This is the HOMO / LUMO image of organic molecule 1. [Diagram 3] This is the HOMO / LUMO image of organic molecule 2. [Figure 4] FIG. 1 shows the emission spectrum of 1 dissolved in toluene (arbitrary units of intensity (au) versus wavelength length (nm)). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0047] Example [ka] JPEG2025508664000008.jpg9955

[0048] Synthesis method Synthesis of 1 [ka]

[0049] Copper(I) iodide (479 mg, 2.5 mmol) and potassium carbonate (13.8 g, 100 mmol) were placed in a 100 mL two-neck flask equipped with a reflux condenser and evacuated for 5 min. Under nitrogen atmosphere, 50 mL of 2-propanol, 1-fluoro-2-iodobenzene (12.2 g, 55 mmol), thiophenol (5.1 mL, 50 mmol) and ethylene glycol (5.6 mL, 100 mmol) were added. The mixture was stirred at 90 °C for 1 day. The reaction solution was filtered and the residue was washed with 100 mL of water and 100 mL of EtOAc. After phase separation, the aqueous phase was further extracted with 100 mL of EtOAc. The combined organic phase was washed with saturated NaCl solution and MgSO 4 The solvent was removed under reduced pressure on a rotary evaporator, and the residue was purified by column chromatography on a small amount of silica gel (eluent: CH 2 Cl 2 The mixture was filtered through a 500 rpm evaporator. The solvent was further removed under reduced pressure on a rotary evaporator to give 9.8 g of diaryl sulfide 1A as a colorless oil containing approximately 10% 1-fluoro-2-iodobenzene but which could be further reacted without additional purification. 1 H-NMR (500 MHz, CDCl 3 ): δ = 7.41-7.37 (m, 2H), 7.37-7.32 (m, 2H), 7.32-7.27 (m, 3H), 7.16-7.08 (m, 2H)

[0050] [ka]

[0051] Diaryl sulfide 1A (90% purity, 6.81 g, 30 mmol) was dissolved in 150 mL of glacial acetic acid and diluted with H 2 O 2(30% in water). The mixture was stirred at 100° C. for 2 hours and then left at room temperature overnight. The reaction solution was added to 800 mL of water, at which time the product precipitated as a white solid. The solid was filtered and washed with water. It was dried in vacuum at 50° C. overnight. 5.8 g of diarylsulfone 1B was obtained as a white solid. 1 H-NMR (500 MHz, CDCl 3 ) δ = 8.11 (td, J = 7.5, 1.8 Hz, 1H), 8.05 - 7.98 (m, 2H), 7.65 - 7.55 (m, 2H), 7.53 (t, J = 7.8 Hz, 2H), 7.32 (t, J = 7.7 Hz, 1H), 7.14 - 7.07 (m, 1H)

[0052] [ka]

[0053] 3,6-Dimethoxycarbazole (696 mg, 3 mmol) was dissolved in 10 mL of dry dimethylformamide (DMF) and NaH (60% in mineral oil, 240 mg, 6 mmol) was added. After stirring for 30 min, diarylsulfone 1B dissolved in 10 mL of methylformamide (DMF) was added and stirred at 100° C. for 2 h. The reaction solution was poured into 200 mL of ice water. After standing overnight, the solid was filtered and washed with a small amount of water. The solid was purified by column chromatography (eluent: CH 2 Cl 2 / cyclohexane) to give 350 mg of product 1, which can be further purified by recrystallization with EtOH. 1 H-NMR (500 MHz, CDCl 3) δ = 8.61 (dd, J = 7.8, 1.8 Hz, 1H), 7.74 (dtd, J = 18.7, 7.5, 1.6 Hz, 2H), 7.44 (d, J = 2.5 Hz, 2H), 7.13 (ddt, J = 5.5, 4.0, 2.2 Hz, 2H), 7.11 - 7.07 (m, 2H), 6.88 (t, J = 7.9 Hz, 2H), 6.76 (dd, J = 8.8, 2.5 Hz, 2H), 6.41 (d, J = 8.8 Hz, 2H), 3.92 (s, 6H) 13 C-NMR (125 MHz, CDCl 3 ) δ = 154.3, 142.7, 139.4, 138.2, 137.1, 135.3, 132.8, 132.8, 130.0, 129.7, 128.4, 127.9, 123.9, 115.0, 111.6, 102.7, 56.3

[0054] Synthesis of 2 [ka]

[0055] 4-Iodobenzonitrile (11.5 g, 500 mmol), copper(I) iodide (957 mg, 5 mmol) and potassium carbonate (13.8 g, 100 mmol) were placed in a 250 mL two-neck flask equipped with a reflux condenser and evacuated for 5 min. Under a nitrogen atmosphere, 100 mL of 2-propanol (iPrOH), 1-fluoro-2-thiobenzene (6.41 g, 50 mmol) and ethylene glycol (5.6 mL, 100 mmol) were added. The mixture was stirred at 90 °C for 1 day. The reaction solution was filtered and the residue was washed with 300 mL of EtOAc. The solvent was removed under reduced pressure on a rotary evaporator and the residue was dissolved in 100 mL of EtOAc and 100 mL of water. The organic phase was washed once more with 100 mL of water, followed by 50 mL of saturated NaCl solution and MgSO 4 The solvent was removed under reduced pressure on a rotary evaporator, and the residue was purified by column chromatography on a small amount of silica gel (eluent: CH2 Cl 2 The mixture was filtered through a cyclohexane-cyclohexane evaporator. The solvent was further removed under reduced pressure on a rotary evaporator. 10.5 g of diaryl sulfide 2A was obtained as a white solid, which contains about 5% of 4-iodobenzonitrile but can be further transformed without further purification. 1 H-NMR (500 MHz, CDCl 3 ): δ = 7.57 - 7.43 (m, 4H), 7.25 - 7.19 (m, 2H), 7.19 - 7.15 (m, 2H)

[0056] [ka]

[0057] Diaryl sulfide 2A (95% purity, 5.31 g, 22 mmol) was dissolved in 150 mL of CH 2 Cl 2 Metachloroperbenzoic acid (mCPBA) (70%, 16.3 g, 66 mmol) was added over about 10 minutes under ice cooling. The mixture was then stirred at room temperature for 16 hours. The reaction solution was dissolved in 100 mL of semi-concentrated Na 2 CO 3 After washing with solution, it was washed with 50 mL of saturated NaCl solution and MgSO 4 The solvent was removed under reduced pressure on a rotary evaporator and the residue was purified by column chromatography on a small amount of silica gel (eluent: CH 2 Cl 2 The mixture was filtered through a cyclohexane distillation column. The solvent was further removed under reduced pressure on a rotary evaporator to give 5.2 g of diaryl sulfone 2B as a pale yellow solid. 1 H-NMR (500 MHz, CDCl 3 ): δ = 8.17 - 8.08 (m, 3H), 7.85 - 7.81 (m, 2H), 7.64 (tdd, J = 7.4, 4.9, 1.8 Hz, 1H), 7.37 (t, J = 7.7 Hz, 1H), 7.18 - 7.10 (m, 1H)

[0058] [ka]

[0059] Carbazole (2.51 g, 15 mmol) was dissolved in 50 mL of dry methylformamide (DMF) and NaH (60% in mineral oil, 1.20 g, 30 mmol) was added. After stirring for 15 min, diarylsulfone 2B dissolved in 50 mL of methylformamide (DMF) was added and stirred at 100° C. for 2 h. The reaction solution was poured into 800 mL of ice. After standing overnight, the solid was filtered and washed with water. The solid was purified by column chromatography (eluent: CH 2 Cl 2 ) to give 3.14 g of product 2 as a white solid. 1 H-NMR (500 MHz, CDCl 3 ): δ = 8.66 - 8.61 (m, 1H), 8.03 (d, J = 7.7 Hz, 2H), 7.89 - 7.80 (m, 2H), 7.30 - 7.23 (m, 5H), 7.19 (ddd, J = 8.2, 7.1, 1.2 Hz, 2H), 7.11 - 7.01 (m, 4H), 6.53 (d, J = 8.0 Hz, 2H) 13 C-NMR (125 MHz, CDCl 3 ) δ = 142.8, 141.9, 141.8, 136.1, 136.0, 133.0, 132.0, 130.3, 130.2, 128.1, 126.1, 123.3, 120.8, 120.1, 11,7.1, 116.2, 110.4

Claims

1. An organic molecule having the structure of Formula A: 【Chemistry 1】 ...Chemical formula A Where: (Het)Ar is a conjugated organic group selected from the group consisting of unsubstituted or substituted aromatics, heteroaromatics, and conjugated double bonds fixed by cis-trans isomerization; D is a chemically attached donor group having electron donating properties; A is a chemically attached acceptor group having electron accepting properties; A and D are bonded to immediately adjacent atoms of the conjugated organic group (Het)Ar.

2. The organic molecule is - The lowest excited singlet (S １ ) state and the triplet (T １ ) between the states １ -T １ ) value is 5,000 cm －１ and / or The organic molecule according to claim 1, having a luminescence lifetime of 50 μs or less.

3. 3. An organic molecule according to claim 1 or 2, wherein (Het)Ar, A and / or D have at least one substituent that increases the solubility of the organic molecule in an organic solvent, wherein the solubility enhancing substituent is preferably selected from the group consisting of: - Length C １ ~C ３０ a branched, unbranched or cyclic long alkyl chain, - Length C １ ~C ３０ a branched or unbranched or cyclic long chain alkoxy chain, - Length 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 repeat units.

4. The organic molecule according to any one of claims 1 to 3, wherein (Het)Ar is phenyl.

5. At least one of the two substituents A and / or D is a heteroatom X, and the substituent is covalently bonded to (Het)Ar via the heteroatom X. The organic molecule according to any one of claims 1 to 4.

6. The organic molecule of claim 5 , wherein the heteroatom X is selected from the group consisting of N, S, P, O and Se.

7. The organic molecule of any one of claims 1 to 6, having the structure of formula C: 【Chemistry 2】 ...Chemical formula C Where: N.R.R. １ is the donor, R.R. １ are independent of each other, Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or a combination of these ２ ), silicon atom -(-SiR ３ a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, etc., having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, etc.; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitrile groups, and CF ３ and other commonly known donor and acceptor groups such as groups; Radicals R and R １ is optionally formed in a fused ring system, The heteroatom Z(=O)n is an acceptor (corresponding to A in chemical formula A or chemical formula B), Z is selected from the group consisting of S and P; n is 1 or 2 to which a further radical R is attached, The radicals are, independently of each other, Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or a combination of these ２ ), silicon atom -(-SiR ３ a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, etc., having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, etc.; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF ３ and other commonly known donor and acceptor groups such as groups; The radical R may also optionally be formed in a fused ring system.

8. The organic molecule of any one of claims 1 to 7, having the structure of formula D: 【Chemistry 3】 ...Chemical formula D Where: NArAr １ is a donor (corresponding to D in chemical formula A or chemical formula B), Here, Ar, Ar １ is optionally aryl, heteroaryl (independently of each other) to which further radicals R are attached, The radical R is Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or a combination of these ２ ), silicon atom -(-SiR ３ a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups, having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and the like; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF ３ and other commonly known donor and acceptor groups, such as aryl, ... The radical R is optionally formed in a fused ring system, Ar and Ar １ may also be condensed with each other or linked with each other via the unit E (e.g., carbazole, phenoxazine); E is a direct bond; a substituted or unsubstituted alkylene group, alkenylene group, alkynylene group, arylene group, or a combination thereof; -O-, -NR-, -SiR ２ -, -S-, -S(O)-, -S(O) ２ -, an alkyl group (including branched or cyclic) terminated by O, a heteroalkyl group, an aryl group, a heteroaryl group, an alkenyl group, a phenyl group; or is an organic linking group which is a substituted phenyl unit; wherein each R is independently Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or a combination of these ２ ), silicon atom -(-SiR ３ a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups, having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and the like; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitrile groups, and CF ３ and other commonly known donor and acceptor groups such as groups; The radical R is optionally formed in a fused ring system, SO ２ Ar ２ is a receptor (A in formula A or B), Here, Ar ２ is an aryl or heteroaryl to which a further radical R is optionally attached, The radicals are, independently of one another, Hydrogen; halogen; oxygen (-OR), nitrogen (-NR) or a combination of these ２ ), silicon atom -(-SiR ３ a substituent bonded through a sulphur atom (-SR); The substituent is Alkyl groups (branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups, having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and the like; Amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitriles, and CF ３ and other commonly known donor and acceptor groups such as groups; The radical R is optionally formed in a fused ring system, Ar is optionally fused to other aryl and heteroaryl groups to form larger aromatic systems.

9. The organic molecule of any one of claims 1 to 7, having the structure of formula E: 【Chemistry 4】 ...Chemical formula E Where: R １ ~R １８ are each independently of the other, Hydrogen; halogen; and oxygen (-OR), nitrogen (-NR) or aryl, either through a direct bond. ２ ), silicon atom -(-SiR ３ or a substituent bonded via a sulfur (-SR) atom, where the radical R corresponds to the definition given for R in formula D; The substituent is Alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, alkenyl groups, alkynyl groups; Substituted alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and alkenyl groups, having substituents such as halogens, deuterium, alkyl groups (including branched or cyclic), heteroalkyl groups, aryl groups, heteroaryl groups, and the like; Optionally, further substituted and / or condensed groups, such as amines, alcohol and ether groups, carbonyl groups, carboxylates and their esters, nitrile groups, and CF ３ and other commonly known donor and acceptor groups such as groups; The radical R １ ~R １８ is optionally formed in a fused ring system.

10. A method for producing an organic molecule according to any one of claims 1 to 9.

11. 11. The method of claim 10, further comprising substituting at least one of the three groups (Het)Ar, A and / or D with at least one substituent to increase solubility, The substituents are selected from the following group: - Length C １ ~C ３０ a long-chain, branched or unbranched, or cyclic alkyl chain, - Length C １ ~C ３０ long chain, branched or unbranched or cyclic alkoxy chains, - Length C １ ~C ３０ and a branched, unbranched or cyclic perfluoroalkyl chain, - Short chain polyethers with a chain length of 3 to 50 repeat units.

12. Use of an organic molecule according to any one of claims 1 to 9 as an emitter or absorber in an optoelectronic device.

13. The use according to claim 12, wherein the optoelectronic element is selected from the following group: - organic light emitting devices (OLEDs), - light-emitting electrochemical cells, OLED sensors, in particular gas and vapor sensors that are not completely sealed off from the outside, -organic solar cells, - organic field effect transistors, - Organic lasers and - Down conversion element.

14. The use according to claim 12 or 13, wherein the proportion of organic molecules in the emitter or the absorber is between 1% and 99%, or 100%.

15. Use according to any of claims 12 to 14, wherein in the optical light emitting device, in particular an OLED, the proportion of organic molecules as emitters is between 5% and 80%.

16. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 9.

17. 17. The optoelectronic device of claim 16, formed of a device selected from the group consisting of an organic light emitting device, an organic diode, an organic solar cell, an organic transistor, an organic light emitting diode, a light emitting electrochemical cell, an organic field effect transistor, and an organic laser.

18. A method for producing an optoelectronic device, in which an organic molecule according to any one of claims 1 to 9 is used.

19. 19. Method according to claim 18, characterized in that the organic molecules according to any one of claims 1 to 9 are applied to a carrier, said application being carried out selectively wet-chemically, by means of a colloidal suspension or by sublimation.

20. A method for modifying the emission and / or absorption properties of an optoelectronic device, characterized in that an organic molecule according to any one of claims 1 to 9 is incorporated into a matrix material for conducting electrons or holes in the optoelectronic device.

21. Use of an organic molecule according to any one of claims 1 to 9, in particular for the conversion (down-conversion) of UV (ultraviolet) or blue light into visible light, in particular green, yellow or red light, in an optoelectronic device.

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