Organic molecules, use of organic molecules, compositions, optoelectronic devices and methods for producing optoelectronic devices

Abstract

The present invention relates in particular to an organic molecule for application in optoelectronic devices. According to the present invention, the organic molecule has the structure of formula I: [Formula 1] JPEG2023522355000096.jpg7289 In formula I, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI is independently selected from the group consisting of: Hydrogen, deuterium, halogens, C 1 -C 12 Alkyl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by C 6 -C 18 Aryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by, and C 3 -C 15 Heteroaryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by R 5 are each independently selected from the group consisting of: Hydrogen, Deuterium C 1 -C 12 Alkyl, and C 6 -C 18 Aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 substituted by alkyl substituents; T, V, W, and X are each independently selected from the group consisting of: C 1 -C 12 Alkyl, and C 6 -C 18 Aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 It is substituted by alkyl substituents.

Description

[Technical field]

[0001] The present invention relates to organic light emitting molecules and their use in organic light emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]

[0002] The problem that the present invention aims to solve is to provide molecules that are suitable for use in optoelectronic devices. [Means for solving the problem]

[0003] Such objectives are achieved by the present invention, which provides novel organic molecules. According to the invention, the organic molecules are purely organic, i.e. they do not contain any metal ions, in contrast to the metal complexes known to be used in optoelectronic devices. However, the organic molecules of the invention may also contain metalloids, in particular B, Si, Sn, Se and / or Ge. Effect of the Invention

[0004] According to the invention, the organic molecules have an emission maximum in the blue, sky blue or green spectral range. The organic molecules have an emission maximum in particular between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm. The photoluminescence quantum yield of the organic molecules according to the invention is in particular greater than 50%. The use of the molecules according to the invention in optoelectronic devices, for example organic light-emitting diodes (OLEDs), leads to a high efficiency or color purity of the device, which is expressed by the emission full width at half maximum (FWHM) of the device. The corresponding OLEDs have a higher safety than known emitter substances and OLEDs of similar hues. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0005] An organic molecule according to the present invention comprises or consists of a structure of Formula I:

[0006] [ka]

[0007] In formula I, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI is independently selected from the group consisting of: Hydrogen, deuterium, halogens, C 1 -C 12 Alkyl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by C 6 -C 18 Aryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by, and C 3 -C 15 Heteroaryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by R 5 are each independently selected from the group consisting of: Hydrogen, deuterium, C 1 -C 12 Alkyl, and C 6 -C 18 Aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 substituted by alkyl substituents; T, V, W, and X are each independently selected from the group consisting of: C 1 -C 12 Alkyl, and C 6 -C 18 Aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 It is substituted by alkyl substituents.

[0008] In some embodiments of the invention, T, V, W, and X are each independently selected from the group consisting of: t Bu, and Me, i Pr and t Ph (phenyl) optionally substituted with one or more substituents independently selected from the group consisting of Bu.

[0009] In one embodiment, the organic molecule comprises or consists of the following structure: [ka]

[0010] where the substituent Ph′ is Me, i Pr, t Represents a phenyl substituent optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0011] In other embodiments, the organic molecule comprises or consists of the structure of Formula I-1 or Formula I-2:

[0012] [ka]

[0013] [ka]

[0014] Here, the above definitions apply. In one embodiment, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI is independently selected from the group consisting of: Hydrogen, deuterium, halogens, C 1 -C 12 Alkyl, C 6 -C 18 Aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 6 Alkyl Substituent or C 6 -C 18 is substituted by an aryl substituent, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 6 Alkyl Substituent or C 6 -C 18 It is substituted by an aryl substituent. In one embodiment, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI is independently selected from the group consisting of: Hydrogen, deuterium, halogens, Me, i Pr, t Bu, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl, and Ph; Me, i Pr, t Carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl and Ph.

[0015] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia to In:

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] [ka]

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] [ka]

[0026] [ka]

[0027] [ka]

[0028] [ka]

[0029] [ka]

[0030] Here, the above definitions apply. In one embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIa to Formula IIn:

[0031] [ka]

[0032] [ka]

[0033] [ka]

[0034]

change

[0035]

change

[0036]

change

[0037]

change

[0038]

change

[0039]

change

[0040]

change

[0041]

change

[0042]

change

[0043]

change

[0044] [ka]

[0045] In one embodiment, R XI is selected from the group consisting of: Hydrogen, deuterium, halogens, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl, and Ph; Me, i Pr, t Carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl and Ph.

[0046] In one embodiment, R XI is selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, cyclohexyl, Ph, and t A carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0047] In some embodiments, R XI is hydrogen or Me. In a preferred embodiment, R XI is hydrogen. In a preferred embodiment, R XI is Me. In a preferred embodiment, R XI is phenyl.

[0048] In some embodiments, R XI teeth, t It is a carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph. In a preferred embodiment, R XIis carbazole, especially unsubstituted carbazole.

[0049] In one embodiment, R I , R II , R III , R IV , R V At least one of, and R VI , R VII , R VIII , R IX or R X At least one of is selected from the group consisting of: C 1 -C 12 Alkyl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by, and C 6 -C 18 Aryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 is replaced by

[0050] In one embodiment of the organic molecule, R I =R X , R II =R IX , R III =R VIII , R IV =R VII , R V =R VI , T=X, and V=W.

[0051] As used throughout this specification, the terms "aryl" and "aromatic" are understood in the broadest sense as any monocyclic, bicyclic or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms. A heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this specification, the number of aromatic ring atoms may be given in subscript numbers in the definition of a particular substituent. In particular, a heteroaromatic ring contains 1 to 3 heteroatoms. Furthermore, the terms "heteroaryl" and "heteroaromatic" are understood in the broadest sense as any monocyclic, bicyclic or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatoms may be the same or different and may be individually selected from the group consisting of N, O and S. Thus, the term "arylene" refers to a divalent substituent that possesses two attachment sites to other molecular structures and serves as a linker structure. In exemplary embodiments, if a group is defined differently than given herein, for example if the number of aromatic ring atoms or heteroatoms is different from the definitions given, the definition in the exemplary embodiment applies. In accordance with the present invention, a fused (annulated) aromatic or heteroaromatic polycycle is composed of two or more single aromatic or heteroaromatic rings that form the polycycle via a condensation reaction.

[0052] In particular, as used throughout this specification, the term "aryl group" or "heteroaryl group" refers to any of the following: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, 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, naphthoimidazole, phenanthridine, pyridoimidazole ... and pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, 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 group that can be attached via any position of the aromatic or heteroaromatic group derived from a combination of the aforementioned groups.

[0053] As used throughout this specification, the term "cyclic group" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0054] As used throughout this specification, the term "biphenyl" is also understood in its broadest sense as a substituent, ortho-biphenyl, meta-biphenyl or para-biphenyl, where ortho, meta and para are defined in relation to the point of attachment to another chemical moiety.

[0055] As used throughout this specification, the term "alkyl group" is 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-propyl ... n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-Butyl ( i Bu), s-Butyl ( s Bu), t-Butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-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-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl -n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n- These include 1,1-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

[0056] As used throughout this specification, the term "alkenyl" includes linear, branched and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0057] As used throughout this specification, the term "alkynyl" includes linear, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0058] As used throughout this specification, the term "alkoxy" includes linear, branched and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

[0059] The term "thioalkoxy" as used throughout this specification includes linear, branched and cyclic thioalkoxy substituents, where the O of the exemplary alkoxy group is replaced with S.

[0060] The terms "halogen" and "halo" as used throughout this specification are also understood in the broadest sense to mean preferably fluorine, chlorine, bromine or iodine.

[0061] Hydrogen (H) is also substituted with deuterium whenever mentioned herein.

[0062] When a molecular fragment is described as being attached to a substituent or other moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above ways of describing the substituent or attached fragment are considered equivalent.

[0063] In one embodiment, in a polymethyl methacrylate (PMMA) film containing 5 wt. % of organic molecules at room temperature, the organic molecules according to the invention have an excited state lifetime of 150 μs or less, 100 μs or less, in particular 50 μs or less, more preferably 10 μs or less, or 7 μs or less.

[0064] In a further embodiment of the invention, in a PMMA film containing 5 wt. % of organic molecules at room temperature, the organic molecules according to the invention have an emission peak in the visible or near UV range, i.e. in the wavelength range of 380 nm to 800 nm, with a full width at half maximum value of 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.

[0065] Orbital energies and excited state energies can be determined through experimental methods. The energy of the highest occupied molecular orbital, E HOMO is determined to an accuracy of 0.1 eV from cyclic voltammetry measurements by methods known to those skilled in the art. The energy of the lowest unoccupied molecular orbital, E LUMO E HOMO +E gap where E gap is determined as follows: for host compounds, unless otherwise specified, the onset of the emission spectrum of a PMMA film containing 10 wt. % of the host is E gap For the emitter molecule, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film containing 10% by weight of the emitter intersect. For the organic molecules according to the invention, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film containing 1 wt. % of the emitter intersect.

[0066] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperature, typically 77K. For host compounds where the first excited singlet state and the lowest triplet state are energetically separated by 0.4 eV or more, phosphorescence is typically visible in the steady-state spectrum in 2-Me-THF. The triplet energy is therefore also determined as 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 77K measured on a PMMA film containing 10% by weight of the emitter, unless otherwise specified, and in the case of organic molecules according to the invention, 1% by weight of the organic molecule according to the invention, unless otherwise specified. 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 on a PMMA film containing 10% by weight of the host or emitter compound, unless otherwise specified, and in the case of organic molecules according to the invention, 1% by weight of the organic molecule according to the invention.

[0067] The onset of the emission spectrum is determined by calculating the intersection point of a tangent to the emission spectrum with the x-axis, the tangent to the emission spectrum being set at the high energy side of the emission band and at half maximum of the maximum intensity of the emission spectrum.

[0068] In one embodiment, the organic molecules according to the invention have an emission spectrum onset close to the maximum emission energetically in a PMMA film comprising 1 wt. % of the organic molecules at room temperature, 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 more preferably less than 0.12 eV, and the full width at half maximum (FWHM) of said organic molecules 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 more preferably 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.

[0069] A further aspect of the present invention relates to the use of the organic molecules according to the invention as light emitters or absorbers and / or host materials and / or electron transport materials and / or hole injection materials and / or hole blocking materials in optoelectronic devices.

[0070] A preferred embodiment concerns the use of organic molecules according to the invention as light emitters in optoelectronic devices.

[0071] An optoelectronic device is understood in the broadest sense as any device based on organic materials suitable for emitting light in the visible or near ultraviolet (UV) range, i.e. in the wavelength range from 380 to 800 nm, more preferably said optoelectronic device is capable of emitting light in the visible range, i.e. in the wavelength range from 400 nm to 800 nm.

[0072] In connection with such applications, the optoelectronic device is more specifically selected from the group consisting of: Organic Light Emitting Diode (OLED) Light-emitting electrochemical cells OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside Organic diode ·Organic solar cells Organic transistors Organic field-effect transistors Organic Lasers Downward conversion element For such applications, in preferred embodiments, 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.

[0073] For said applications, the fraction of the organic molecules according to the invention in the light-emitting layer in an optoelectronic device, more particularly in an OLED, is 0.1% to 99% by weight, more particularly 1% to 80% by weight. In another embodiment, the fraction of said organic molecules in the light-emitting layer is 100% by weight.

[0074] In one embodiment, the light-emitting layer comprises not only the organic molecule according to the present invention but also a host material whose triplet (T1) energy level and singlet (S1) energy level are higher than the triplet (T1) energy level and singlet (S1) energy level of the organic molecule.

[0075] A further aspect of the invention relates to a composition comprising or consisting of: (a) one or more organic molecules according to the invention in emitter and / or host form (b) one or more emitter substances and / or host substances different from the organic molecules according to the invention (c) optionally, one or more dyes and / or one or more solvents.

[0076] In one embodiment, the light-emitting layer comprises or consists essentially of a composition comprising or consisting of: (a) one or more organic molecules according to the invention, in particular in emitter and / or host form; (b) one or more emitter substances and / or host substances different from the organic molecules according to the invention (c) optionally, one or more dyes and / or one or more solvents.

[0077] In particular embodiments, the emissive layer EML comprises or consists essentially of a composition comprising or consisting of: (i) 0.1 to 10% by weight, preferably 0.5 to 5% by weight, in particular 1 to 3% by weight, of one or more organic molecules according to the invention. (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight, of one or more host compounds H (iii) 0.9 to 94.9% by weight, preferably 14.5 to 80% by weight, in particular 24 to 77% by weight, of one or more additional host compounds D having a structure different from that of the molecules according to the invention. (iv) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent; (v) optionally 0 to 30% by weight, in particular 0 to 20% by weight, preferably 0 to 5% by weight of at least one additional emitter molecule F having a structure different from that of the molecule according to the invention.

[0078] Preferably, energy is transferred from the host compound H to one or more organic molecules according to the 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 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 invention.

[0079] In one embodiment, the host compound H has an energy E in the range of −5 to −6.5 eV. HOMO (H), and at least one additional host compound D has a highest occupied molecular orbital HOMO (H) with energy E HOMO (D) has the highest occupied molecular orbital HOMO (D), where E HOMO (H)>E HOMO (D).

[0080] In a further embodiment, the host compound H has an energy E LUMO (H), and at least one additional host compound D has a lowest unoccupied molecular orbital LUMO (H) with energy E LUMO (D) has a lowest unoccupied molecular orbital LUMO (D), where E LUMO (H)>E LUMO (D).

[0081] In one embodiment, the host compound H has an energy E HOMO The highest occupied molecular orbital (HOMO) with (H) and energy E LUMO (H) having a lowest unoccupied molecular orbital LUMO (H); At least one additional host compound D has an energy E HOMO (D) highest occupied molecular orbital HOMO(D), and energy E LUMO has a lowest unoccupied molecular orbital (LUMO) (D); The organic molecule E according to the present invention has energy E HOMO (E) highest occupied molecular orbital HOMO (E), with energy E LUMO (E) having a lowest unoccupied molecular orbital LUMO (E); Where: E HOMO (H)>E HOMO (D) and the energy level (E HOMO (E)) and the energy level of the highest occupied molecular orbital (HOMO) of the host compound H (E HOMO (H)) is −0.5 eV to 0.5 eV, more preferably −0.3 eV to 0.3 eV, even more preferably −0.2 eV to 0.2 eV, and still more preferably −0.1 eV to 0.1 eV, E LUMO (H)>E LUMO (D) and the energy level of the lowest unoccupied molecular orbital (LUMO) (E) of the organic molecule E according to the present invention (E LUMO (E)) and the energy level of the lowest unoccupied molecular orbital (LUMO) (D) of at least one additional host compound D (E LUMO The difference from (D)) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV, and further preferably -0.1 eV to 0.1 eV.

[0082] In one embodiment of the present invention, the host compound D and / or the host compound H is a thermally activated delayed fluorescent (TADF) material. The TADF material has a wavelength of 2500 cm -1 ΔE corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) of less than ST Preferably, the TADF material has a wavelength of 3000 cm -1 less than 1500 cm -1 less than 1000 cm -1 Less than 500 cm, more preferably -1 Less than ΔE ST Indicates the value.

[0083] In one embodiment, host compound D is a TADF material and host compound H is a 2500 cm -1 Larger ΔE ST In a particular embodiment, the host compound D is a TADF material and the host compound H is 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-dibenzothiophenyl)phenyl]-9H-carbazole.

[0084] In one embodiment, host compound H is a TADF material and host compound D is a 2500 cm -1 Larger ΔE ST In a particular embodiment, the host compound H is a TADF material and the host compound D is selected from the group consisting of 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9′-spirobifluoren-2-yl)-1,3,5-triazine (TST).

[0085] 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 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 completely sealed off from the outside, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and downward conversion devices.

[0086] 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.

[0087] In one embodiment of the inventive optoelectronic device, an organic molecule E according to the invention is used as emissive material in the emissive layer EML.

[0088] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the inventive composition described herein.

[0089] When the optoelectronic device is an OLED, it can have, for example, the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer Here, the OLED optionally includes layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above.

[0090] Additionally, the optoelectronic device, in one embodiment, also includes at least one protective layer that protects the device from damaging exposure to harmful substances in the environment including, for example, moisture, vapors and / or gases.

[0091] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Light-emitting layer B 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A Here, the OLED optionally includes layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above.

[0092] In one embodiment of the present invention, the optoelectronic device is an OLED that can have a stacked structure. In this structure, individual units are stacked on top of each other, unlike the common arrangement in which OLEDs are arranged side by side. Mixed light is generated by an OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED, and a red OLED. An OLED that exhibits a stacked structure may also include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally configured as an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0093] In one embodiment of the present invention, the optoelectronic device is an OLED that includes two or more light-emitting layers between an anode and a cathode. In particular, the so-called tandem OLED includes three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and may optionally include additional layers between each light-emitting layer, such as a charge generation layer, a charge blocking layer, or a charge transport layer. In a further embodiment, the light-emitting layers are stacked adjacent to each other. In a further embodiment, the tandem OLED includes a charge generation layer between each two light-emitting layers. Also, adjacent light-emitting layers or light-emitting layers separated by a charge generation layer can be merged.

[0094] The substrate is made of any material or composition of materials. Mostly, 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 a plastic slide can be used, which allows a higher level of flexibility. The anode layer A is made of a material that allows obtaining an almost (essentially) transparent film. To allow light emission from the OLED, at least one of the two electrodes must be (essentially) transparent, so that either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such anode layers A may, for example, comprise 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.

[0095] The anode layer A is made of (essentially) indium tin oxide (ITO) (e.g., InO 3 ) 0.9 (SnO 2 ) 0.1 The roughness of the anode layer A due to the transparent conducting oxide (TCO) is also mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of similar charge carriers (i.e. holes) in that the transport of similar charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) is made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonic acid (PSS), MoO 2 , V 2 O 5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent diffusion of metals from the anode layer A into the hole transport layer (HTL). For example, the HIL can be poly-3,4-ethylenedioxythiophene:polystyrenesulfonate (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalene-2-yl)phenylamine (NAPH), N,N'-bis ... It is also composed of N,N'-triphenyl-N,N'-bis-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0096] Adjacent to the anode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles are also used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) is also an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) may be formed of tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′,4″-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or 9,9′-diphenyl-6-(9-phenyl-9H- The HTL may also include star-shaped heterocycles such as carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer composed of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopant may be, for example, a transition metal oxide such as vanadium oxide, molybdenum oxide or tungsten oxide. The organic dopant may be, for example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or a transition metal complex.

[0097] EBLs may include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0098] Adjacent to the hole transport layer (HTL) is typically located an emissive layer (EML). The emissive layer (EML) comprises at least one emissive molecule. In particular, the EML comprises one or more emissive molecules E according to the invention. In one embodiment, the emissive layer comprises only organic molecules according to the invention. Typically, the EML further comprises one or more host materials H. For example, the host material H may be 4,4′-bis-(N-carbazolyl)-biphenyl (CBP), mCP, mCBP, dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), CzSi, dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran ... [3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9′-spirobifluoren-2-yl)-1,3,5-triazine (TST). The host material H should generally be selected to exhibit a first triplet (T1) energy level and a first singlet (S1) energy level that are energetically higher than the first triplet (T1) energy level and the first singlet (S1) energy level of the organic molecule.

[0099] In one embodiment of the present invention, the EML comprises a so-called mixed host system, which has 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, T2T as the electron-dominant host, and one 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-dibenzothiophenyl)phenyl]-9H-carbazole as the hole-dominant host. In a further embodiment, the EML comprises 50-80% by weight, preferably 60-75% by weight, 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-dibenzothiophenyl)phenyl]-9H-carbazole, 10-45% by weight, preferably 15-30% by weight, of T2T, and 5-40% by weight, preferably 10-30% by weight, of an emissive molecule according to the present invention.

[0100] Adjacent to the light-emitting layer (EML) may be an electron transport layer (ETL). Any electron transporter may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxides and sulfones may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may also include 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq3), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,7-di(2,2′-bipyridin-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or 4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl (BTB). Optionally, the ETL is also doped with a material such as Liq. The electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) is introduced.

[0101] Examples of HBL include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq3), diphenyl-4-triphenylsilylphenyl-phosphineoxy, and the like. side (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9′-spirobifluoren-2-yl)-1,3,5-triazine (TST) and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0102] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g. Al, Au, Ag, Pt, Cu, Zn, NiFe, Pb, LiF, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca or Al. Alternatively, or in addition, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscale silver wires.

[0103] The OLED may optionally further include a protective layer (also referred to as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The layer may be any of lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li 2 O, BaF 2 , MgO and / or NaF.

[0104] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) also contain one or more host compounds H.

[0105] To additionally modify the emission and / or absorption spectrum of the emissive layer EML, the emissive layer EML may further comprise one or more additional emitter molecules F. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F are molecules having a structure different from that of the molecules E according to the invention. The emitter molecules F are optionally also TADF emitters. Alternatively, the emitter molecules F are optionally also fluorescent and / or phosphorescent emitter molecules capable of shifting the emission and / or absorption spectrum of the emissive layer EML. For example, triplet and / or singlet excitons may be converted to the ground state S 0 Before being relaxed to , the emitter molecule according to the invention can also be transferred to the emitter molecule F, which can emit light that is typically red-shifted compared to the light emitted by the organic molecule. Optionally, the emitter molecule F can also induce a two-photon effect (i.e. the absorption of two photons that are half the maximum absorbed energy).

[0106] Optionally, the optoelectronic device (e.g., an OLED) may also be, for example, an essentially white optoelectronic device. For example, such a white optoelectronic device may include at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and / or red light. Optionally, there may then be an energy transfer between the two or more molecules, as described above.

[0107] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: >380~420nm wavelength range Deep blue: Wavelength range >420~480nm Sky blue color: >480~500nm wavelength range Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: >620~800nm ​​wavelength range Associated with the emitter molecule, such hues exhibit maximum emission, so for example, a deep blue emitter has a maximum emission in the range >420-480 nm, a sky blue emitter has a maximum emission in the range >480-500 nm, a green emitter has a maximum emission in the range >500-560 nm, and a red emitter has a maximum emission in the range >620-800 nm.

[0108] Deep blue emitters may preferably have a maximum emission less than 480 nm, more preferably less than 470 nm, even more preferably less than 465 nm, and even more preferably less than 460 nm. The maximum emission is typically greater than 420 nm, preferably greater than 430 nm, more preferably greater than 440 nm, and even more preferably greater than 450 nm.

[0109] Thus, a further aspect of the present invention is 2 an OLED that exhibits an external quantum efficiency of more than 8%, preferably more than 10%, more preferably more than 13%, even more preferably more than 15%, and even more preferably more than 20% at 500 cd / m; an OLED that exhibits a maximum emission at 420 nm to 500 nm, preferably at 430 nm to 490 nm, more preferably at 440 nm to 480 nm, and even more preferably at 450 nm to 470 nm; and / or an OLED that exhibits a maximum emission at 500 cd / m 2 The present invention thus relates to an OLED having an LT80 value of greater than 100 h, preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, and even more preferably greater than 1000 h. A further aspect of the present invention thus relates to an OLED having an emission exhibiting a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20, even more preferably less than 0.15, and even more preferably less than 0.10.

[0110] Yet another aspect of the present invention relates to an OLED that emits light at a well-defined color point. According to the present invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the present invention emits light having a FWHM of the main emission peak 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, and even more preferably less than 0.17 eV.

[0111] Yet another aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of primary blue (CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and is suitable for use in an Ultra High Definition (UHD) display, such as a UHD-TV. Thus, a further aspect of the present invention relates to an OLED whose emission exhibits a CIEx color coordinate of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, even more preferably 0.08 to 0.18, and even more preferably 0.10 to 0.15, and / or a CIEy color coordinate of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, even more preferably 0.03 to 0.15, and even more preferably 0.04 to 0.10.

[0112] In a further aspect, the invention relates to a method for producing an optoelectronic component, in which the organic molecules of the invention are used.

[0113] The optoelectronic device, in particular the OLED according to the invention, may be produced by any means of vapor deposition and / or liquid crystal processes. Thus, at least one layer may be - Produced by the sublimation process; -Manufactured by organic vapor phase deposition process, - Produced by a carrier gas sublimation process; - Solution processed or printed.

[0114] The methods used to manufacture 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 steps. The individual layers can be deposited using the same or different deposition methods.

[0115] For example, the vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. The individual layers are also processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art.

[0116] Working Example General synthetic scheme I General synthetic scheme I shows the synthesis of R I =R X , R II =R IX , R III =R VIII , R IV =R VII , R V =R VI , T=X and V=W.

[0117] [ka]

[0118] [ka]

[0119] [ka]

[0120] [ka]

[0121] General procedure for synthetic AAV1: [ka]

[0122] E1 (1.00 equivalent), aniline (E2 2.20 equivalent), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu) 3 (0.04 equivalents, CAS: 13716-12-6) and sodium tert-butoxide NaO t Bu (4.20 equiv., CAS: 865-48-5) is stirred in toluene under nitrogen at 90° C. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic phase is diluted with MgSO 4 After drying on the stove, the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give product I1 as a solid.

[0123] General procedure for synthetic AAV2: [ka]

[0124] I1 (1.00 equivalent), E3 (2.10 equivalent), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalents, CAS: 13716-12-6) and sodium tert-butoxide NaO t Bu (4.00 equiv., CAS: 865-48-5) is stirred in toluene under nitrogen atmosphere at 110° C. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic phase is diluted with MgSO 4 After drying on the stove, the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give the product I2 as a solid.

[0125] General procedure for synthetic AAV3: [ka] I2 (1.00 equiv.) is stirred in tBu-benzene at 40°C under a nitrogen atmosphere. tert-Butyllithium ( t BuLi, 2.20 equiv., CAS 594-19-4) is added dropwise and the reaction is heated to 50 °C. Trimethyl borate (6 equiv., CAS 121-43-7) is added slowly at room temperature to quench the lithiation. The reaction mixture is heated at 60 °C for 2 h, after which the reaction mixture is cooled to room temperature. Water is added and the mixture is stirred for an additional 2 h. After extraction with ethyl acetate, the organic phase is washed with MgSO 4 After drying on the stove, the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give product I3 as a solid.

[0126] General procedure for synthetic AAV4: [ka]

[0127] I3 (1.00 equiv.) was stirred in chlorobenzene under a nitrogen atmosphere. N,N-diisopropylethylamine (10.0 equiv., CAS7087-68-5) and aluminum chloride (AlCl 3, 10.0 equiv., CAS 7446-70-0) is added and the reaction mixture is heated to 120° C. After 60 minutes, N,N-diisopropylethylamine (5.00 equiv., CAS 7087-68-5) and aluminum chloride (AlCl 3 , 5.00 eq., CAS7446-70-0) is added and the reaction mixture is stirred for 1.5 h. After cooling to room temperature, the reaction mixture is extracted between DCM and water. The organic phase is diluted with MgSO 4 After drying on the stover, the solvent is removed under reduced pressure. The crude product P1 is further purified by recrystallization or column chromatography.

[0128] General procedure for synthetic AAV5: [ka]

[0129] E4 (1.00 equiv.), E5 (1.50 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (Pd 2 (dba) 3 , 0.005 equiv., CAS 51364-51-3), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (0.02 equiv., X-Phos, CAS 564483-18-7) and tripotassium phosphate (K 3 PO 4 , 2.00 equiv., CAS7778-53-2) is suspended in toluene / water (4:1, by volume) under nitrogen atmosphere. The mixture is heated to 110° C. until the reaction is complete. After cooling to room temperature, the phases are separated and the aqueous phase is extracted with ethyl acetate. The combined organic layers are washed with activated carbon / celite® / MgSO 4 The crude material is purified by recrystallization to give E2.

[0130] Cyclic voltammogram The cyclic voltage and current are measured at a concentration of 10 for organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). -3 The measurement is performed at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and FeCp 2 / FeCp 2 + The HOMO data were corrected using peroxene as an internal standard relative to a saturated calomel electrode (SCE).

[0131] Density functional theory calculations The molecular structures were optimized using the BP86 function and the Resolution of Identity (RI) approach. The excitation energies were calculated with the Time-Dependent DFT (TD-DFT) method using the (BP86) optimized structures. The orbital energies and excited state energies were calculated with the B3LYP function. For numerical integration, the Def2-SVP basis set and m4-grid were used. The Turbomole program package was used for all calculations.

[0132] photophysical measurements Sample preparation: spin coating Equipment: Spin150, SPSeuro Sample concentration is 10 mg / ml dissolved in an appropriate solvent.

[0133] Program: 1) 400 U / min for 3 sec, 1,000 U / min for 20 sec (1,000 U / m / s). 3) 4,000 U / min for 10 sec (1,000 U / m / s). After coating, the film was dried at 70° C. for 1 min.

[0134] Photoluminescence spectroscopy and time-correlated single photon coefficient (TCSPC) Steady-state emission spectroscopy was recorded using a Model FluoroMax-4 (Horiba Scientific) equipped with a 150 W xenon-Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and time-correlated single photon counting options. Standard correction fits were used to correct the emission and excitation spectra.

[0135] The excited state lifetimes are determined using the same system using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub.

[0136] Excitation light source: NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns) NanoLED 290 (wavelength: 294nm, pulse duration: <1ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm) Data analysis (exponential fit) is performed using the software suite DataStation and DAS6 analysis software. The fit is determined using the chi-squared test.

[0137] Photoluminescence quantum yield measurements For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0138] Emission maxima are given in nm, quantum yields Φ are given in %, and CIE coordinates are given as x,y values.

[0139] The PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard. 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured on solution or film samples in a nitrogen atmosphere. The yield is calculated using the following equation:

[0140]

number

[0141] Fabrication and characterization of optoelectronic devices Optoelectronic devices, particularly OLED devices, comprising the organic molecules according to the invention can also be produced by vacuum deposition methods. When a layer comprises one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so that when no value is specified, the proportion of the compound is equal to the difference between the specified value and 100%.

[0142] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance, similarly LT80 corresponds to the point when the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the point when the measured luminance has decreased to 95% of the initial luminance.

[0143] Accelerated lifetime measurements are performed (e.g. by applying increased current densities), e.g. 500cd / m 2 In the present invention, the LT80 value is determined using the following formula:

[0144]

number

[0145] Here, L 0 denotes the initial luminance at an applied current density. The value corresponds to the average of several pixels (typically 2-8) and the standard deviation across the pixels is provided.

[0146] HPLC-MS HPLC-MS analysis is performed on an Agilent HPLC (1100 series) equipped with an MS-detector (Thermo LTQ XL).

[0147] The general HPLC method is as follows: A reversed-phase column 4.6 mm x 150 mm and particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6 x 150 mm, 3.5 μm HPLC column) is used for HPLC. HPLC-MS measurements are performed at room temperature (rt) with a gradient.

[0148] [Table 1]

[0149] [Table 2]

[0150] From the analyte solution at a concentration of 0.5 mg / mL, an injection volume of 5 μL was taken for the measurement. The ionization of the probe is by cation (APCI + ) ionization mode or negative (APCI - ) ionization mode using an APCI (atmospheric pressure chemical ionization) source.

[0151] Example 1 [ka]

[0152] Example 1 was synthesized as follows. AAV5 (44% yield) using 4-tert-butyl-3-chloroaniline (CAS 52756-36-2) as E4 and phenylboronic acid (CAS 98-80-6) as E5; AAV1 (52%) with 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) as E1; AAV2 (69% yield) using 1-bromo-3,5-di-tert-butylbenzene (CAS 22385-77-9) as E3; AAV3 (26% yield) and AAV4 (15% yield).

[0153] MS (HPLC-MS), m / z (residence time): 924.4 (8.75 minutes) The emission maximum of Example 1 (2% by weight in PMMA) is 461 nm with a full width at half maximum (FWHM) of 0.16 eV and a CIE y coordinate of 0.11. The photoluminescence quantum yield (PLQY) is 77%.

[0154] Example D1 Example 1 was tested on an OLED D1 fabricated with the following layer structure:

[0155] [Table 3]

[0156] [ka]

[0157] [ka]

[0158] The OLED D1 is 1000cd / m 2At 3.7 V, the external quantum efficiency (EQE) is 11.1%. At 3.7 V, the maximum emission is 465 nm with a FWHM of 28 nm. The CIEx value is 0.13 and the CIEy value is 0.10. The LT95 value is 1200 cd / m 2 It was determined that the time was 12 hours.

[0159] Additional Examples of Organic Molecules of the Invention [ka]

[0160] [ka]

[0161] [ka]

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168]

change

[0169]

change

[0170]

change

[0171]

change

[0172]

change

Claims

1. An organic molecule comprising the structure of Formula I: 【Chemistry 1】 In formula I, R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ , R Ｘ and R ＸＩ is independently selected from the group consisting of: Hydrogen, deuterium, halogens, C １ -C １２ Alkyl, wherein optionally, one or more hydrogen atoms are independently selected from R ５ is replaced by C ６ -C １８ Aryl, wherein optionally, one or more hydrogen atoms are independently selected from R ５ is replaced by, and C ３ -C １５ Heteroaryl, wherein optionally, one or more hydrogen atoms are independently selected from R ５ is replaced by R ５ are each independently selected from the group consisting of: Hydrogen, deuterium, C １ -C １２ Alkyl, and C ６ -C １８ Aryl, wherein optionally one or more hydrogen atoms are independently selected from C １ -C ５ substituted by alkyl substituents; T, V, W, and X are each independently selected from the group consisting of: C １ -C １２ Alkyl, and C ６ -C １８ Aryl, T is C 1 -C 12 alkyl, or C 6 -C 18 aryl; V is C 6 -C 18 aryl when T is C 1 -C 12 alkyl, and C 1 -C 12 alkyl when T is C 6 -C 18 aryl; W is C 1 -C 12 alkyl, or C 6 -C 18 aryl; X is C 6 -C 18 aryl when W is C 1 -C 12 alkyl, and C 1 -C 12 alkyl when W is C 6 -C 18 aryl; wherein optionally one or more hydrogen atoms are independently selected from C １ -C ５ It is substituted by alkyl substituents.

2. T is one or more substituents independently selected from the group consisting of Me, i Pr and t Bu, or Ph; V is Ph when T is one or more substituents independently selected from the group consisting of Me, iPr, and tBu, and when T is Ph, V is one or more substituents independently selected from the group consisting of Me, iPr, and tBu; W is one or more substituents independently selected from the group consisting of Me, i Pr and t Bu, or Ph; 2. The organic molecule of claim 1, wherein X is Ph when W is one or more substituents independently selected from the group consisting of Me, iPr, and tBu, and when W is Ph, X is one or more substituents independently selected from the group consisting of Me, iPr, and tBu.

3. The organic molecule of claim 1 or 2, comprising the structure of formula I-1 or I-2: 【Chemistry 2】 【Chemistry 3】 。

4. R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ , R Ｘ and R ＸＩ is independently selected from the group consisting of: Hydrogen, deuterium, halogens, C １ -C １２ Alkyl, C ６ -C １８ Aryl, wherein optionally one or more hydrogen atoms are independently selected from C １ -C ６ Alkyl Substituent or C ６ -C １８ is substituted by an aryl substituent, and C ３ -C １５ Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C １ -C ６ Alkyl Substituent or C ６ -C １８ It is substituted by an aryl substituent.

5. R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ , R Ｘ and R ＸＩ is independently selected from the group consisting of: Hydrogen, deuterium, halogen, Me, ｉ P.R. ｔ B, Me, ｉ P.R. ｔ Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl, and Ph; Me, ｉ P.R. ｔ A carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl and Ph.

6. The organic molecule of any one of claims 1 to 5, comprising a structure selected from the group consisting of formula Ia to formula In: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 。

7. The organic molecule of any one of claims 1 to 6, comprising a structure selected from the group consisting of Formula IIa to Formula IIn: 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 。

8. R ＸＩ The organic molecule according to any one of claims 1 to 7, wherein is selected from the group consisting of: Hydrogen, deuterium, halogen, Me, ｉ P.R. ｔ B, Me, ｉ P.R. ｔ Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl, and Ph; Me, ｉ P.R. ｔ A carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu, cyclohexyl and Ph.

9. R ＸＩ The organic molecule according to any one of claims 1 to 8, wherein is selected from the group consisting of: Hydrogen, deuterium, Me, ｉ P.R. ｔ Bu, cyclohexyl, Ph, and ｔ A carbazole optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

10. R ＸＩ The organic molecule according to any one of claims 1 to 9, wherein is hydrogen or Me.

11. Use of an organic molecule according to any one of claims 1 to 10 as a light emitter in an optical element.

12. The use of organic molecules according to claim 11, wherein the optical element is selected from the group consisting of: ・Organic Light Emitting Diode (OLED) Light-emitting electrochemical cells ・OLED sensor ・Organic diode ・Organic solar cells ・Organic transistors ・Organic field effect transistor ・Organic laser ・Downward conversion element.

13. A composition comprising: (a) an organic molecule according to any one of claims 1 to 10 in emitter and / or host form, (b) an emitter material and / or a host material different from the organic molecule; and (c) optionally, a dye and / or a solvent.

14. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 10 or a composition according to claim 13 in a form 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 downward conversion device.

15. -substrate, -anode, a cathode, and - comprises a light-emitting layer, The anode or the cathode is disposed on the substrate; The optoelectronic device of claim 14 , wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or composition.

16. A method for the manufacture of an optoelectronic device, in which an organic molecule according to any one of claims 1 to 10 or a composition according to claim 13 is used, comprising the step of processing said organic molecule by a vacuum evaporation method or from a solution.

Images