Organic molecules for optoelectronic devices

Abstract

The present invention relates to an organic molecule particularly useful in optoelectronic devices. According to the present invention, the organic molecule has a structure of formula I: wherein R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X independently selected from: hydrogen; deuterium; halogen; C1-C4-alkyl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 Replaced by; and C6‑C 18 -aryl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 Replaced. #imgabs0#

Description

[0001] The present invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices.

[0002] describe

[0003] The object of the present invention is to provide molecules suitable for use in optoelectronic devices.

[0004] This object is achieved by the present invention, which provides a new class of organic molecules.

[0005] According to the invention, the organic molecules are pure organic molecules, i.e., they do not contain any metal ions in contrast to the metal complexes known for use in optoelectronic devices. However, the organic molecules of the invention comprise metalloids, in particular B, Si, Sn, Se and / or Ge.

[0006] According to the present invention, the organic molecules exhibit an emission maximum in the blue, sky-blue, or green spectral range. In particular, the organic molecules exhibit an emission maximum between 420 nm and 520 nm, preferably between 440 nm and 495 nm, and more preferably between 450 nm and 470 nm. In particular, the photoluminescence quantum yield of the organic molecules according to the present invention is 50% or higher. The use of the molecules according to the present invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), can result in higher device efficiency or higher color purity, expressed as the full width at half maximum (FWHM) of the emission. The corresponding OLEDs have higher stability than OLEDs with known emitter materials and comparable colors.

[0007] The organic light-emitting molecule according to the present invention comprises a structure of formula I or consists of a structure of formula I:

[0008]

[0009] in

[0010] R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X Each independently of the other is selected from:

[0011] Hydrogen; Deuterium; Halogen;

[0012] C1-C4-alkyl,

[0013] wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced by;

[0014] C6-C 18 -cycloalkyl,

[0015] wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced by;

[0016] C6-C 18 -aryl,

[0017] wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced.

[0018] R 5 are independently selected from the group consisting of: hydrogen; deuterium;

[0019] C1-C5-alkyl,

[0020] wherein optionally one or more hydrogen atoms are independently replaced by deuterium;

[0021] C6-C 18 -cycloalkyl,

[0022] wherein optionally one or more hydrogen atoms are independently replaced by a C1-C5-alkyl substituent;

[0023] C6-C 18 -aryl,

[0024] wherein optionally one or more hydrogen atoms are independently replaced by a C1-C5-alkyl substituent.

[0025] R of organic molecules I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX or R X At least one selected from:

[0026] C1-C4-alkyl,

[0027] wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced by;

[0028] C6-C 18 -cycloalkyl,

[0029] wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced by;

[0030] C6-C 18 -aryl,

[0031] wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced.

[0032] Optionally, each hydrogen is independently replaced by deuterium or halogen.

[0033] In some embodiments, R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X Each independently selected from:

[0034] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0035] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, t Substituted with Bu and phenyl (Ph) substituents;

[0036] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0037] In some embodiments, R I 、R II 、R III 、R IV 、R V At least two of the R VI 、R VII 、R VIII 、R IX and R X Two of them are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0038] In a preferred embodiment, R II 、R IV 、R VII and R IX For Ph.

[0039] In a preferred embodiment, R II 、R IV 、RVII and R IX for t Bu.

[0040] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia:

[0041]

[0042] where R I 、R II 、R III 、R IV and R V Independently selected from:

[0043] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0044] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, t Substituted by Bu and Ph substituents;

[0045] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0046] In one embodiment, the organic molecule comprises or consists of a structure of Formula Ia, wherein R I 、R II 、R III 、R IV 、R V At least two of which are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0047] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib:

[0048]

[0049] where R I 、R II 、R III 、R IV and R V Independently selected from:

[0050] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0051] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, t Substituted by Bu and Ph substituents;

[0052] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0053] In one embodiment, the organic molecule comprises or consists of a structure of Formula Ib, wherein R I 、R II 、R III 、R IV 、R V At least two of which are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0054] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ic:

[0055]

[0056] where R I 、R II 、R III 、R IV and R V Independently selected from:

[0057] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0058] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, t Substituted by Bu and Ph substituents;

[0059] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0060] In one embodiment, the organic molecule comprises or consists of a structure of Formula Ic, wherein R I 、R II 、R III 、R IV 、R V At least two of which are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0061] In one embodiment, the organic molecule comprises or consists of the structure of Formula Id:

[0062]

[0063] where R I 、R II 、R III 、R IV and R V Independently selected from:

[0064] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0065] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, t substituted with Bu and Ph substituents; and

[0066] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0067] In one embodiment, the organic molecule comprises or consists of a structure of Formula Id, wherein R I 、R II 、R III 、R IV 、R V At least two of which are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0068] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ie:

[0069]

[0070] where R I 、R II 、R III 、R IV and R V Independently selected from:

[0071] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0072] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, tsubstituted with Bu and Ph substituents; and

[0073] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0074] In one embodiment, the organic molecule comprises or consists of a structure of Formula Ie, wherein R I 、R II 、R III 、R IV 、R V At least two of which are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0075] In one embodiment, the organic molecule comprises or consists of a structure of formula If:

[0076]

[0077] where R I 、R II 、R III 、R IV and R V Independently selected from:

[0078] Hydrogen; Deuterium; Halogen; Me; i Pr; t Bu;

[0079] Cyclohexyl, which is optionally substituted by one or more independently selected from Me, i Pr, t substituted with Bu and Ph substituents; and

[0080] Ph, which is optionally replaced by one or more independently selected from Me, i Pr, t The cyclohexyl group and the cyclohexyl group are substituted.

[0081] In one embodiment, the organic molecule comprises or consists of a structure of formula If, wherein R I 、R II 、R III 、R IV 、R V At least two of which are independently selected from Me, i Pr, t Bu, cyclohexyl and Ph.

[0082] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense to mean any monocyclic, bicyclic, or polycyclic aromatic moiety. Accordingly, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this application, in the definition of certain substituents, the number of aromatic ring atoms can be given as a subscript number. In particular, a heteroaromatic ring contains one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense to mean any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatoms can be the same or different at each occurrence and can be selected individually from N, O, and S. Accordingly, the term "arylene" refers to a divalent substituent having two binding sites with other molecular structures and thus serving as a linker structure. In some cases, the groups in the exemplary embodiments are defined differently from the definitions given here, for example, the number of aromatic ring atoms or the number of heteroatoms is different from the given definition, and the definitions in the exemplary embodiments will apply. According to the present invention, a fused (cyclic) aromatic or heteroaromatic polycyclic ring is composed of two or more monoaromatic or heteroaromatic rings, which form a polycyclic ring via a condensation reaction.

[0083] In particular, as used throughout this document, the term "aryl group or heteroaryl group" includes groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, Perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzene oxazole, naphthoxazole, anthraxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or a combination of the foregoing.

[0084] As used throughout this document, the term "cyclic group" is to be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0085] As used throughout this document, the term "biphenyl" as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl or para-biphenyl, wherein the ortho, meta and para positions are defined with respect to the site of binding to another chemical moiety.

[0086] As used throughout this document, the term "alkyl group" is to be understood in the broadest sense as any linear, branched or cyclic alkyl substituent. In particular, the term alkyl includes the substituents methyl (Me), ethyl (Et), n-propyl ( n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 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, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hexan-1-yl, 1,1-dimethyl-n-heptan-1-yl, 1,1-dimethyl-n-octan-1-yl, 1,1-dimethyl-n-decan-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-hexan-1-yl, 1,1-diethyl-n-heptan-1-yl, 1,1-diethyl-n-octan-1-yl, 1,1-diethyl-n-decan-1-yl, 1,1-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)-cyclohexan-1-yl, 1-(n-butyl)-cyclohexan-1-yl, 1-(n-hexyl)-cyclohexan-1-yl, 1-(n-octyl)-cyclohexan-1-yl and 1-(n-decyl)-cyclohexan-1-yl.

[0087] As used throughout this article, the term "alkenyl" includes straight chain, branched and cyclic alkenyl substituents. For example, the term "alkenyl group" includes the substituents: ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0088] As used throughout this article, the term "alkynyl" includes straight chain, branched and cyclic alkynyl substituents. For example, the term "alkynyl group" includes ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0089] As used throughout this article, the term "alkoxy" includes straight chain, branched and cyclic alkoxy substituents. For example, the term "alkoxy group" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy and 2-methylbutoxy.

[0090] As used throughout, the term "thioalkoxy" includes linear, branched, and cyclic thioalkoxy substituents wherein the O of the exemplary alkoxy group is replaced with S.

[0091] As used throughout, the terms "halogen" and "halo" are to be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0092] Whenever hydrogen (H) is mentioned herein, it may also be replaced by deuterium at each occurrence.

[0093] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it is a fragment (e.g., naphthyl, dibenzofuranyl) or as if it is an entire molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0094] In one embodiment, the organic molecules according to the present invention have an excited state lifetime of no more than 150 μs, no more than 100 μs, in particular no more than 50 μs, more preferably no more than 10 μs or no more than 7 μs in a poly(methyl methacrylate) (PMMA) film having 5 wt.% of organic molecules at room temperature.

[0095] In yet another embodiment of the present invention, the organic molecules according to the present invention have an emission peak in the visible or near-UV range, i.e. in the wavelength range of 380 nm to 800 nm, and the full width at half maximum in a poly(methyl methacrylate) (PMMA) film with 5 wt.% of organic molecules at room temperature is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV.

[0096] Orbital and excited state energies can be determined experimentally. The energy of the highest occupied molecular orbital, E HOMO The energy of the lowest unoccupied molecular orbital, E, is determined from cyclic voltammetry measurements to an accuracy of 0.1 eV by methods known to those skilled in the art. LUMO Calculated as E HOMO +E gap, where E gap Determined as follows: For the host compound, the starting value of the emission spectrum of a film with 10 wt. % host in poly(methyl methacrylate) (PMMA) is used as E gap , unless otherwise stated. For emitter molecules, E gap Determined as the energy at which the excitation and emission spectra of a film with 10 wt. % emitter in PMMA cross. For the organic molecules according to the invention, E gap Determined as the energy at which the excitation and emission spectra of a film with 5 wt% emitter in PMMA cross.

[0097] The energy of the first excited triplet state, T1, is determined from the onset of the emission spectrum at low temperatures, typically 77 K. For host compounds in which the first excited singlet state and the lowest triplet state are separated in energy by >0.4 eV, phosphorescence is typically visible in the steady-state spectrum in 2-Me-THF. The triplet energy can therefore be determined from the onset of the phosphorescence spectrum. For TADF emitter molecules, the energy of the first excited triplet state, T1, is determined from the onset of the delayed emission spectrum at 77 K, measured, if not otherwise stated, in a PMMA film containing 10 wt% emitter, or, in the case of organic molecules according to the invention, in a PMMA film containing 1 wt% of the organic molecule according to the invention. For both host and emitter compounds, the energy of the first excited singlet state, S1, is determined from the onset of the emission spectrum, measured, if not otherwise stated, in a PMMA film containing 10 wt% host or emitter compound, or, in the case of organic molecules according to the invention, in a PMMA film containing 1 wt% of the organic molecule according to the invention.

[0098] The starting value of the emission spectrum is determined by calculating the intersection of the tangent line of the emission spectrum with the x-axis. The tangent line of the emission spectrum is set on the high energy side of the emission band and at a point half the maximum intensity of the emission spectrum.

[0099] In one embodiment, the organic molecules according to the present invention have an emission spectrum onset that is energetically close to the maximum emission, i.e., the energy difference between the emission spectrum onset and the energy of the maximum emission is less than 0.14 eV, preferably less than 0.13 eV, or even less than 0.12 eV, while the full width at half maximum (FWHM) of the organic molecules in a poly(methyl methacrylate) (PMMA) film having 5 wt% of organic molecules at room temperature is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV, resulting in a CIE y coordinate of less than 0.20, preferably less than 0.18, more preferably less than 0.16 or even more preferably less than 0.14.

[0100] A further aspect of the present invention relates to the use of the organic molecules of the present invention as luminescent emitters or as absorbers and / or as host materials and / or as electron transport materials and / or as hole injection materials and / or as hole blocking materials in optoelectronic devices.

[0101] A preferred embodiment relates to the use of the organic molecules according to the invention as luminescent emitters in optoelectronic devices.

[0102] An optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or near ultraviolet (UV) range, i.e., in the wavelength range of 380 to 800 nm. More preferably, the optoelectronic device may be capable of emitting light in the visible range, i.e., 400 nm to 800 nm.

[0103] In this context of use, the optoelectronic device is more particularly selected from:

[0104] Organic light-emitting diodes (OLEDs),

[0105] ·Luminescent electrochemical cells,

[0106] OLED sensors, especially gas and vapor sensors, are not hermetically shielded from the surrounding environment.

[0107] Organic diodes,

[0108] Organic solar cells,

[0109] Organic transistors,

[0110] Organic field effect transistors,

[0111] Organic lasers, and

[0112] Down-conversion components.

[0113] In a preferred embodiment in this use context, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC) and a light emitting transistor.

[0114] For the purposes described, the fraction of the organic molecules according to the invention in the emission layer of an optoelectronic device, more particularly an OLED, is from 0.1% to 99% by weight, more particularly from 1% to 80% by weight. In an alternative embodiment, the proportion of organic molecules in the emission layer is 100% by weight.

[0115] In one embodiment, the light-emitting layer comprises not only the organic molecule according to the invention but also a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than those of the organic molecule.

[0116] Yet another aspect of the present invention relates to a composition comprising or consisting of:

[0117] (a) at least one organic molecule according to the invention, in particular in the form of an emitter and / or host, and

[0118] (b) one or more emitter and / or host materials which are different from the organic molecules according to the invention, and

[0119] (c) optionally one or more dyes and / or one or more solvents.

[0120] In one embodiment, the light-emitting layer comprises (or consists essentially of) a composition comprising or consisting of:

[0121] (a) at least one organic molecule according to the invention, in particular in the form of an emitter and / or host, and

[0122] (b) one or more emitter and / or host materials which are different from the organic molecules according to the invention, and

[0123] (c) optionally one or more dyes and / or one or more solvents.

[0124] In a particular embodiment, the light-emitting layer EML comprises (or consists essentially of) a composition comprising or consisting of:

[0125] (i) 0.1-10% by weight, preferably 0.5-5% by weight, in particular 1-3% by weight, of one or more organic molecules according to the invention;

[0126] (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight of at least one host compound H; and

[0127] (iii) 0.9-94.9% by weight, preferably 14.5-80% by weight, in particular 24-77% by weight, of at least one further host compound D, the structure of which differs from the structure of the molecule according to the invention; and

[0128] (iv) optionally 0-94% by weight, preferably 0-65% by weight, in particular 0-50% by weight of a solvent; and

[0129] (v) optionally 0 to 30% by weight, in particular 0 to 20% by weight, preferably 0 to 5% by weight, of at least one further emitter molecule F, the structure of which differs from the structure of the molecules according to the invention.

[0130] Preferably, energy can be transferred from the host compound H to one or more organic molecules according to the present invention, in particular from the first excited triplet state T1(H) of the host compound H to the first excited triplet state T1(E) of one or more organic molecules E according to the present invention and / or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of one or more organic molecules E according to the present invention.

[0131] In one embodiment, the host compound H has an energy E HOMO (H) the highest occupied molecular orbital HOMO (H) in the range of -5 to -6.5 eV, and the at least one other host compound D has an energy E HOMO (D) the highest occupied molecular orbital HOMO (D), where E HOMO (H)>E HOMO (D).

[0132] In yet another embodiment, the host compound H has an energy E LUMO (H), and the at least one other host compound D has an energy E LUMO (D) is the lowest unoccupied molecular orbital LUMO(D), where E LUMO (H)>E LUMO (D).

[0133] In one embodiment, the host compound H has an energy E HOMO The highest occupied molecular orbital HOMO(H) has an energy of E LUMO the lowest unoccupied molecular orbital LUMO(H), and

[0134] The at least one other host compound D has an energy E HOMO The highest occupied molecular orbital HOMO(D) of (D) has energy E LUMO (D) the lowest unoccupied molecular orbital LUMO(D),

[0135] The organic molecule E according to the present invention has an energy E HOMO The highest occupied molecular orbital HOMO(E) has an energy of E LUMO The lowest unoccupied molecular orbital LUMO(E) of (E),

[0136] in

[0137] E HOMO (H)>E HOMO (D) and the energy level (E) of the highest occupied molecular orbital HOMO (E) of the organic molecule E according to the present inventionHOMO (E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound (E HOMO (H)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV; and

[0138] E LUMO (H)>E LUMO (D) and the energy level (E) of the lowest unoccupied molecular orbital LUMO (E) of the organic molecule E according to the present invention LUMO (E)) and the energy level (E) of the lowest unoccupied molecular orbital LUMO (D) of at least one other host compound D LUMO The difference between (D)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV.

[0139] In one embodiment of the present invention, host compound D and / or host compound H is a thermally activated delayed fluorescence (TADF) material. TADF materials exhibit a fluorescence intensity less than 2500 cm -1 ΔE ST , which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1). Preferably, the TADF material exhibits a ΔH of less than 3000 cm -1 , more preferably less than 1500cm -1 , even more preferably less than 1000 cm -1 Or even less than 500cm -1 ΔE ST value.

[0140] In one embodiment, host compound D is a TADF material and host compound H exhibits a -1 ΔE ST In a particular embodiment, the host compound D is a TADF material and the host compound H is selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene-2-yl)phenyl]-9H-carbazole.

[0141] In one embodiment, host compound H is a TADF material and host compound D exhibits a -1 ΔE ST In a particular embodiment, the host compound H is a TADF material and the host compound D is selected from T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9′-spirobifluoren-2-yl)-1,3,5-triazine).

[0142] In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition of the type described herein, more particularly in the form of a device selected from the group consisting of: organic light-emitting diodes (OLEDs); light-emitting electrochemical cells; OLED sensors, in particular gas and vapor sensors that are not hermetically shielded from the outside; organic diodes; organic solar cells; organic transistors; organic field-effect transistors; organic lasers and down-conversion elements.

[0143] In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light emitting transistor.

[0144] In one embodiment of the optoelectronic device of the present invention, the organic molecules E according to the present invention are used as light-emitting material in the light-emitting layer EML.

[0145] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of a composition according to the invention described herein.

[0146] When the optoelectronic device is an OLED, it may, for example, have the following layer structure:

[0147] 1. Substrate

[0148] 2. Anode layer A

[0149] 3. Hole injection layer HIL

[0150] 4. Hole Transport Layer (HTL)

[0151] 5. Electron blocking layer EBL

[0152] 6. Emission Layer (EML)

[0153] 7. Hole blocking layer HBL

[0154] 8. Electron Transport Layer (ETL)

[0155] 9. Electron injection layer EIL

[0156] 10. Cathode layer,

[0157] Where the OLED comprises each layer selected from the group consisting of a HIL, HTL, EBL, HBL, ETL and EIL, only optionally the different layers may be combined and the OLED may comprise more than one layer of each layer type defined above.

[0158] Additionally, in one embodiment, the optoelectronic device may include one or more protective layers that protect the device from exposure to harmful substances in the environment, including, for example, moisture, vapor, and / or gases.

[0159] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0160] 1. Substrate

[0161] 2. Cathode layer

[0162] 3. Electron injection layer EIL

[0163] 4. Electron Transport Layer (ETL)

[0164] 5. Hole blocking layer HBL

[0165] 6. Emission layer B

[0166] 7. Electron blocking layer EBL

[0167] 8. Hole Transport Layer (HTL)

[0168] 9. Hole injection layer HIL

[0169] 10. Anode layer A

[0170] Where the OLED comprises each layer selected from the group consisting of a HIL, HTL, EBL, HBL, ETL and EIL, only optionally the different layers may be combined and the OLED may comprise more than one layer of each layer type defined above.

[0171] In one embodiment of the present invention, the optoelectronic device is an OLED, which may have a stacked structure. In this structure, the individual OLEDs are stacked on top of each other, as opposed to the typical arrangement in which OLEDs are placed side by side. OLEDs with a stacked structure can be used to produce mixed light, and in particular, white light can be produced by stacking blue, green, and red OLEDs. Furthermore, OLEDs with a stacked structure may include a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of n-doped and p-doped layers, with the n-doped layer of one CGL typically located closer to the anode layer.

[0172] In one embodiment of the present invention, the optoelectronic device is an OLED comprising two or more emissive layers between an anode and a cathode. In particular, this so-called tandem OLED comprises three emissive layers, one of which emits red light, one emits green light, and one emits blue light, and optionally may comprise other layers such as charge generation layers, blocking or transport layers between the individual emissive layers. In another embodiment, the emissive layers are stacked adjacent to each other. In another embodiment, the tandem OLED comprises a charge generation layer between each two emissive layers. In addition, adjacent emissive layers or emissive layers separated by a charge generation layer may be combined.

[0173] The substrate can be formed from any material or combination of materials. Most commonly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver, or aluminum film) or a plastic film or slide can be used. This allows for a higher degree of flexibility. The anode layer A is primarily composed of a material that allows a (substantially) transparent film to be obtained. Since at least one of the two electrodes should be (substantially) transparent to allow light emission from the OLED, the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A contains a large amount of transparent conductive oxide (TCO) or even consists of a transparent conductive oxide (TCO). Such anode layer A may, for example, contain indium tin oxide, aluminum zinc oxide, fluorine-doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole, and / or doped polythiophene.

[0174] The anode layer A may (essentially) be made of indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1). The roughness of the anode layer A caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). Furthermore, the HIL can facilitate the injection of quasi-charge carriers (i.e., holes) by promoting the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) can contain poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC, or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL). The HIL may, for example, comprise PEDOT:PSS (poly-3,4-ethylenedioxythiophene:polystyrenesulfonate), PEDOT (poly-3,4-ethylenedioxythiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetrakis(N,N-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'-bis- (1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-bis-[4-(N,N-diphenyl-amino)phenyl]-p-diaminobenzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)-p-diaminobenzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexanitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0175] A hole transport layer (HTL) is typically provided adjacent to the anode layer A or hole injection layer (HIL). Any hole transport compound can be used. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can be used as hole transport compounds. The HTL can lower the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high triplet T1 energy level. For example, the hole transport layer (HTL) may contain star-shaped heterocycles such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [α]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4′-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, and PEG-TPD. D, HAT-CN, and / or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Furthermore, the HTL may include a p-doped layer, which may consist of an inorganic or organic dopant in an organic hole-transporting matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide can be used, for example, as inorganic dopants. Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used, for example, as organic dopants.

[0176] The EBL may, for example, contain mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N′-dicarbazyl-1,4-dimethylbenzene).

[0177] Adjacent to the hole transport layer (HTL), an emitting layer EML is usually provided. The emitting layer EML comprises at least one emitting molecule. In particular, the EML comprises at least one emitting molecule E according to the present invention. In one embodiment, the emitting layer comprises only organic molecules according to the present invention. Typically, the EML further comprises one or more host materials H. For example, the host material H is selected from CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H -carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothienyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9′-spirobifluoren-2-yl)-1,3,5-triazine). The host material H should generally be selected to have a first triplet state (T1) and a first singlet state (S1) energy level that are energetically higher than the first triplet state (T1) and the first singlet state (S1) energy levels of the organic molecule.

[0178] In one embodiment of the present invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises exactly one light-emitting organic molecule according to the present invention and a hybrid host system comprising T2T as the electron-dominant host and a host selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophen-2-yl)phenyl]-9H-carbazole as the hole-dominant host. In yet another embodiment, the EML comprises 50-80 wt%, preferably 60-75 wt%, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole; 10-45 wt%, preferably 15-30 wt% of T2T and 5-40 wt%, preferably 10-30 wt% of a light-emitting molecule according to the present invention.

[0179] An electron transport layer (ETL) may be provided adjacent to the light-emitting layer (EML). Any electron transport agent may be used herein. For example, electron-poor compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron transport agent may also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may include NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenyl), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), and / or BTB (4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Optionally, the ETL may be doped with a material such as Liq. An electron transport layer (ETL) may also block holes or introduce a hole blocking layer (HBL).

[0180] The HBL may, for example, comprise BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), BAlq (bis(8-hydroxy-2-methylquinolinol)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinolinol)), TSPO1 (diphenyl-4-triphenylsilylbenzene), (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazolyl)benzene).

[0181] Adjacent to the electron transport layer (ETL), a cathode layer C may be provided. Cathode layer C may, for example, comprise or consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also consist (essentially consist) of an opaque metal such as Mg, Ca, or Al. Alternatively or additionally, cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, cathode layer C may also consist of nanoscale silver filaments.

[0182] The OLED may also optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. This layer may include lithium fluoride, cesium fluoride, silver, Liq (lithium 8-hydroxyquinoline), Li2O, BaF2, MgO, and / or NaF.

[0183] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may also comprise one or more host compounds H.

[0184] In order to further modify the emission spectrum and / or absorption spectrum of the light-emitting layer EML, the light-emitting layer EML may further comprise one or more other emitter molecules F. Such emitter molecules F may be any emitter molecules known in the art. Preferably, such emitter molecules F are molecules having a structure different from that of the molecules E according to the present invention. The emitter molecule F may optionally be a TADF emitter. Alternatively, the emitter molecule F may optionally be a fluorescent and / or phosphorescent emitter molecule that is capable of changing the emission spectrum and / or absorption spectrum of the light-emitting layer EML. Exemplarily, triplet and / or singlet excitons may be transferred from the organic emitter molecules according to the present invention to the emitter molecules F, and then relax to the ground state S0 by emitting light that is generally red-shifted compared to the light emitted by the organic molecules. Optionally, the emitter molecule F may also cause a two-photon effect (i.e., absorbing two photons of half the maximum absorption energy).

[0185] Optionally, the optoelectronic device (e.g., OLED) can be, for example, a substantially white optoelectronic device. For example, such a white optoelectronic device can comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Energy transfer can then optionally occur between the two or more molecules as described above.

[0186] As used herein, if not more specifically defined in a particular context, the color of emitted and / or absorbed light is designated as follows:

[0187] Purple: wavelength range >380-420nm;

[0188] Dark blue: wavelength range >420-480nm;

[0189] Sky blue: wavelength range >480-500nm;

[0190] Green: wavelength range >500-560nm;

[0191] Yellow: wavelength range >560-580nm;

[0192] Orange: wavelength range >580-620nm;

[0193] Red: Wavelength range >620-800nm.

[0194] With respect to emitter molecules, such colors refer to the emission maximum. Thus, for example, a deep blue emitter has an emission maximum in the range >420 to 480 nm, a sky blue emitter has an emission maximum in the range >480 to 500 nm, a green emitter has an emission maximum in the range >500 to 560 nm, and a red emitter has an emission maximum in the range >620 to 800 nm.

[0195] The emission maximum of the deep blue emitter is preferably below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It is typically above 420 nm, preferably above 430 nm, more preferably above 440 nm, or even above 450 nm.

[0196] Accordingly, another aspect of the present invention relates to an OLED having a brightness of 1000 cd / m 2 The external quantum efficiency at 500 nm is greater than 8%, more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15% or even greater than 20% and / or the maximum emission is between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and / or at 500 cd / m 2 The LT80 value under 100 hours is greater than 100 hours, preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours or even greater than 1000 hours. Accordingly, a further aspect of the present invention relates to an OLED having an emission CIE y color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.

[0197] Yet another aspect of the present invention relates to an OLED that emits light at different color points. According to the present invention, the light emitted by the OLED has a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the FWHM of the main emission peak of the light emitted by the OLED according to the present invention is less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.19 eV, or even less than 0.17 eV.

[0198] Yet another aspect of the present invention relates to an OLED whose emitted light has CIEx and CIEy color coordinates close to the color coordinates CIEx (=0.131) and CIEy (=0.046) of the primary color blue (CIEx=0.131 and CIEy=0.046) as defined in ITU-R Recommendation BT.2020 (Rec.2020) and is therefore suitable for use in ultra-high-definition (UHD) displays such as UHD-TVs. Accordingly, a further aspect of the invention relates to an OLED having an emission CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and / or a CIEy color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.

[0199] In a further aspect, the present invention relates to a method for producing an optoelectronic component, wherein the organic molecules according to the invention are used.

[0200] Optoelectronic devices, in particular OLEDs according to the invention, can be produced by any vapor deposition and / or liquid processing methods. Accordingly, at least one layer

[0201] - prepared by sublimation process,

[0202] - prepared by organic vapor deposition process,

[0203] - prepared by carrier gas sublimation process,

[0204] - is solution processed or printed.

[0205] Methods for producing optoelectronic devices, in particular OLEDs according to the present invention, are known in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition processes. The individual layers can be deposited using the same or different deposition methods.

[0206] Vapor deposition processes include, for example, thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. Individual layers can be processed from a solution or dispersion using an appropriate solvent. Solution deposition processes include, for example, spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent can be completely or partially removed by measures known in the art. Example

[0207] General Synthesis Scheme I

[0208] General Synthesis Scheme 1 provides an organic molecule according to the present invention (wherein R I =R X , R II =R IX , R III =R VIII , R IV =R VII , and R V =R VI ) synthesis scheme:

[0209]

[0210] General procedure for synthesizing AAV1:

[0211]

[0212] E1 (1.00 equivalent), 2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-amine (E2 2.20 equivalent, CAS: 851534-18-4), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalent, CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalent, CAS: 13716-12-6) and sodium tert-butoxide NaO t Bu (4.20 equivalents, CAS: 865-48-5) was stirred in toluene at 90°C under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The organic layers were combined and dried over MgSO4, and the solvent was removed under reduced pressure. The resulting crude product was purified by recrystallization or column chromatography to obtain I1 as a solid.

[0213] General procedure for synthesizing AAV2:

[0214]

[0215] I1 (1.00 equivalent), E3 (2.10 equivalent), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalent, CAS: 13716-12-6) and sodium tert-butoxide NaO tBu (4.00 equivalents, CAS: 865-48-5) was stirred in toluene at 110 ° C under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine and the phases were separated. The organic layers were combined and dried over MgSO4, and the solvent was removed under reduced pressure. The resulting crude product was purified by recrystallization or column chromatography to obtain I2 as a solid.

[0216] General procedure for synthesizing AAV3:

[0217]

[0218] I2 (1 equivalent) was added under nitrogen atmosphere. t Bu-benzene was stirred at 40 ° C. Tert-butyl lithium ( t The mixture was stirred for 2 hours at room temperature. After 3 hours, the mixture was cooled to room temperature. Water was added and the mixture was stirred for another 2 hours. After extraction with ethyl acetate, the organic phase was dried with MgSO4, and the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to obtain I3 as a solid.

[0219] General procedure for synthesizing AAV4:

[0220]

[0221] I3 (1 equivalent) is stirred in chlorobenzene under a nitrogen atmosphere. N, N-diisopropylethylamine (10.0 equivalents, CAS 7087-68-5) and aluminum chloride (AlCl3, 10.0 equivalents, CAS 7446-70-0) are added and the reaction mixture is heated to 120 ° C. After 60 minutes, N, N-diisopropylethylamine (5.00 equivalents, CAS 7087-68-5) and aluminum chloride (AlCl3, 5.00 equivalents, CAS 7446-70-0) are added and the reaction mixture is stirred for 1.5 hours. After cooling to room temperature, the reaction mixture is extracted between DCM and water. The organic layer is dried with MgSO4 and some solvents are removed under reduced pressure. Ethanol is added to the remaining organic phase and stored in a refrigerator for 1 hour. The solid precipitated is then filtered and dried. The crude product P1 can be further purified by recrystallization or column chromatography.

[0222] Cyclic voltammetry

[0223] From a concentration of 10 -3Cyclic voltammograms were measured for solutions of 100 mol / L organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). The measurements were performed at room temperature under nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and using FeCp2 / FeCp2 + The HOMO data were calibrated against a saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0224] Density functional theory calculations

[0225] The molecular structure was optimized using the BP86 functional and the unit decomposition method (RI). Excitation energies were calculated using the (BP86) optimized structure with the time-dependent DFT (TD-DFT) method. Orbital and excited state energies were calculated using the B3LYP functional. The Def2-SVP basis set (and m4-grid for numerical integration) were used. All calculations were performed using the Turbomole package.

[0226] Photophysical measurements

[0227] Sample pretreatment: spin coating

[0228] Device:Spin150, SPS euro.

[0229] The sample concentration was 10 mg / ml and was dissolved in a suitable solvent.

[0230] Procedure: 1) 400 U / min for 3 s; 1000 U / min, 1000 U / s for 20 s. 3) 4000 U / min, 1000 U / s for 10 s. After coating, the film was dried at 70°C for 1 minute.

[0231] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC)

[0232] Steady-state emission spectra were measured using a Horiba Scientific Modell FluoroMax-4 equipped with a 150W xenon arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and a time-correlated single photon counting option. Emission and excitation spectra were corrected using standard calibration fits.

[0233] The excited state lifetimes were determined using the same system with the TCSPC method using an FM-2013 instrument and the Horiba Yvon TCSPC hub.

[0234] Excitation source:

[0235] NanoLED 370 (wavelength: 371nm, pulse duration: 1.1ns)

[0236] NanoLED 290 (wavelength: 294nm, pulse duration: <1ns)

[0237] SpectraLED 310 (wavelength: 314nm)

[0238] SpectraLED 355 (wavelength: 355nm).

[0239] Data analysis (exponential fitting) was performed using the software suite DataStation and DAS6 analysis software. The fit was evaluated using the chi-square test.

[0240] Photoluminescence quantum yield measurement

[0241] For photoluminescence quantum yield (PLQY) measurements, an absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yield and CIE coordinates were determined using software U6039-05 version 3.6.0.

[0242] The emission maximum is given in nm, the quantum yield Φ is given in %, and the CIE coordinates are given as x,y values.

[0243] PLQY was determined using the following scheme:

[0244] 1) Quality assurance: Use anthracene (known concentration) in ethanol as a reference

[0245] 2) Excitation wavelength: Determine the maximum absorption of the organic molecule and use this wavelength to excite the molecule

[0246] 3) Measurement

[0247] Measure the quantum yield of a sample of solution or film under a nitrogen atmosphere. Calculate the yield using the following formula:

[0248]

[0249] where n 光子 represents the photon count and Int. represents the intensity.

[0250] Fabrication and characterization of optoelectronic devices

[0251] Optoelectronic devices, in particular OLED devices, comprising the organic molecules according to the present invention can be produced by vacuum deposition methods. If a layer contains more than one compound, the weight percentage of the compound or compounds is given in %. The total weight percentage value amounts to 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0252] Non-optimized OLEDs are characterized using standard methods and measured electroluminescence spectra. The external quantum efficiency (expressed in %) depends on the intensity and current, with the intensity calculated using the light detected by the photodiode. The OLED device lifetime is derived from the change in brightness during operation at a constant current density. The LT50 value corresponds to the time at which the measured brightness drops to 50% of the initial brightness. Similarly, LT80 corresponds to the time point at which the measured brightness drops to 80% of the initial brightness, LT95 corresponds to the time point at which the measured brightness drops to 95% of the initial brightness, and so on.

[0253] Perform accelerated lifetime measurements (e.g., apply increasing current density). For example, calculate 500 cd / m using the following formula: 2 The following LT80 values:

[0254]

[0255] where L0 represents the initial luminance at the applied current density.

[0256] These values ​​correspond to the average of several (usually two to eight) pixels, giving the standard deviation between these pixels.

[0257] HPLC-MS

[0258] HPLC-MS analysis was performed on HPLC by Agilent (1100 series) and MS-detector (Thermo LTQ XL).

[0259] For example, a typical HPLC method is as follows: a reverse phase column 4,6 mm x 150 mm with a particle size of 3.5 μm from Agilent (ZORBAX Eclipse Plus C18, 4.6x150mm, 3.5μm HPLC column). HPLC-MS measurements were performed at room temperature (rt) using a gradient.

[0260]

[0261] The following solvent mixture was used:

[0262] Solvent A: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent B: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent C: THF (50%) MeCN (50%)

[0263] A 5 μL injection volume was taken from a solution with an analyte concentration of 0.5 mg / mL for measurement.

[0264] Ionization of the probe was performed using an atmospheric pressure chemical ionization (APCI) source in either positive (APCI+) or negative (APCI-) ionization mode.

[0265] Example 1

[0266]

[0267] According to the following synthesis example 1

[0268] AAV1 (yield 30%);

[0269] AAV2, in which 1-bromo-3,5-di-tert-butylbenzene was used as reactant E3 (yield 67%);

[0270] AAV3 (yield 20%);

[0271] and AAV4 (yield 79%).

[0272] MS (HPLC-MS), m / z (retention time): 881.90 (8.94 min).

[0273] Comparative Example C1

[0274]

[0275] Example 1 and Comparative Example 1 were tested in OLED D1 and OLED CD1, respectively, which were manufactured to have the following structures:

[0276]

[0277]

[0278] Both devices exhibited deep blue emission. CD1 produced a relative EQE of 1.00, while device example D1 achieved a relative EQE of 1.12. It can be seen that the molecules according to the present invention exhibit superior performance compared to the prior art.

[0279] Other examples of organic molecules of the present invention

[0280]

Claims

1. An organic molecule comprising a structure of Formula I: in R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X Independently selected from: hydrogen; halogens; and C1-C4-alkyl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced by; R 5 independently at each occurrence: C1-C5-alkyl, R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX or R X At least one selected from: C1-C4-alkyl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 replaced by; And optionally, each hydrogen is independently replaced by deuterium or halogen.

2. The organic molecule according to claim 1, wherein R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X Independently selected from: Hydrogen; Deuterium; Halogen; Me; i Pr; and t Bu.

3. The organic molecule according to claim 1 or 2, wherein R I 、R II 、R III 、R IV 、R V At least two of the R VI 、R VII 、R VIII 、R IX and R X Two of which are independently selected from Me, i Pr, and t Bu.

4. The organic molecule according to claim 1 or 2, wherein R II 、R IV 、R VII and R IX Each for t Bu.

5. The organic molecule according to claim 3, wherein the organic molecule comprises a structure of Formula Ia:

6. The organic molecule according to claim 3, wherein the organic molecule comprises a structure of Formula Ic:

7. Use of an organic molecule according to any one of claims 1 to 6 as a luminescent emitter in an optoelectronic device.

8. The use according to claim 7, wherein the optoelectronic device is selected from: Organic light-emitting diodes (OLEDs), ·Luminescent electrochemical cells, OLED-sensors, Organic diodes, Organic solar cells, Organic transistors, Organic field effect transistors, Organic lasers, and Down-conversion components.

9. A composition comprising: (a) an organic molecule according to any one of claims 1 to 6 (b) an emitter and / or host material different from the organic molecule, and (c) optionally a dye and / or a solvent.

10. The composition according to claim 9, comprising the organic molecules in the form of emitters and / or hosts.

11. An optoelectronic device comprising the organic molecule according to any one of claims 1 to 6 or the composition according to claim 9 or 10.

12. The optoelectronic device according to claim 11, comprising the composition in the form of a device selected from the group consisting of: an organic light emitting diode (OLED); a light emitting electrochemical cell; an OLED sensor; an organic diode; an organic solar cell; an organic transistor; an organic field effect transistor; an organic laser and a down-conversion element.

13. The optoelectronic device according to claim 12, comprising: - substrate, -anode, - a cathode, wherein the anode or the cathode is disposed on the substrate, and - a light-emitting layer, which is arranged between the anode and the cathode and comprises the organic molecule or the composition.

14. A method for producing an optoelectronic device, wherein the organic molecule according to any one of claims 1 to 6 or the composition according to claim 9 or 10 is used.

15. The method of claim 14, comprising processing the organic molecule by vacuum evaporation or from solution.

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