Organic molecules for optoelectronic devices, optoelectronic devices, uses in optoelectronic devices, and methods for producing optoelectronic devices

Abstract

The present invention relates to an organic molecule, particularly for application in optoelectronic devices. According to the present invention, the organic molecule has the structure of Formula I: [Formula 1] JPEG2023514978000046.jpg4565Chemical formula I Here, R I , R II , R III , R IV , R V , R VI , R VII , R A , R B , R C , R D , R E , R F , R G and R H are 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 are independently substituted by C 6 -C 18 -aryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 and C 3 -C 15 Heteroaryl, wherein optionally, one or more hydrogen atoms are independently selected from R 5 are independently substituted by Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R A , R B , R C , R D , R E , R F , RG and R H any two adjacent ones of which form a monocyclic ring system having 5 to 8 C-atoms, At least, R A and R B Not just R C and R D also form a monocyclic ring system having 5 to 8 C-atoms, wherein, optionally, each hydrogen is independently replaced.

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] It is an object of the present invention to provide molecules suitable for use in optoelectronic devices. [Means for solving the problem]

[0003] This objective is achieved by the present invention, which provides a new class of organic molecules.

[0004] According to the invention, the organic molecules are purely organic, i.e., in contrast to the metal complexes known to be used in optoelectronic devices, they do not contain any metal ions. However, the organic molecules of the invention contain metalloids, in particular B, Si, Sn, Se and / or Ge.

[0005] According to the invention, the organic molecules exhibit an emission maximum in the blue, sky blue or green spectral range. The organic molecules exhibit an emission maximum in particular at 420 nm to 520 nm, preferably at 440 nm to 495 nm, more preferably at 450 nm to 470 nm. The photoluminescence quantum efficiency of the organic molecules according to the invention is in particular 50% or more. In optoelectronic devices, for example organic light-emitting diodes (OLEDs), the use of the molecules according to the invention leads to a higher efficiency or color purity, expressed by the full width at half maximum (FWHM) of the emission of the device. The corresponding OLEDs have a higher stability and a comparable color than OLEDs containing known emitter substances. [Brief description of the drawings]

[0006] [Figure 1] 1 is an emission spectrum of Example 1 (2 wt %) in PMMA. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] The organic light-emitting molecule according to the present invention comprises or consists of the structure of formula I: [ka] Chemical formula I Where: R I , R II , R III , R IV , R V , R VI , R VII , R A , R B , R C , R D , R E , R F , R G and R H 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.

[0008] R 5 is independently selected in each occurrence 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 6 is replaced by C 6 -C 18 -aryl, wherein optionally, one or more hydrogen atoms are independently selected from R 6 is replaced by, and C 3 -C 15 Heteroaryl, wherein optionally, one or more hydrogen atoms are independently selected from R 6 is replaced by.

[0009] R 6 is independently selected at each occurrence 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 5 -substituted with alkyl substituents, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 - substituted with alkyl substituents.

[0010] R of organic matter I , R II , R III , R IV , R V , R VI , R VII , R A , R B , R C , R D , R E , R F , R G and R H of which any two adjacent can form a monocyclic ring system having 5, 6, 7 or 8 C-atoms.

[0011] At least, R A and R B Not just organic molecules R C and R D also form monocyclic ring systems having 5, 6, 7 or 8 C-atoms, wherein optionally each hydrogen is independently selected from R 6 can be substituted with

[0012] Optionally, each hydrogen of the organic molecule is independently replaced with deuterium or a halogen.

[0013] In certain embodiments of the organic molecule, each R I , R II , R III , R IV , R V , R VI and R VII are 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 5 -substituted with an alkyl substituent, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 - substituted with alkyl substituents, Here, optionally, R I , R II , R III and R IV Among them, any two adjacent ones (i.e., R I and R II and / or R III and R IV ) form a monocyclic ring system consisting of 5 to 8 C-atoms (i.e. 5, 6, 7 or 8 carbon atoms), Here, optionally, each hydrogen can be independently replaced with methyl (Me).

[0014] The term "monocyclic ring system" specifically refers to a non-aromatic ring system.

[0015] In certain embodiments of the organic molecule, each R I , R II , R III , R IV , R V , R VI and R VII is independently selected from the group consisting of hydrogen, deuterium, halogen, Me, tBu, Ph (phenyl), cyclohexyl, and carbazole; Here, optionally, R I , R II , R III and R IV any two adjacent ones of these together form a monocyclic ring system having 5 to 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0016] In certain embodiments of the organic molecule, each R I , R II , R III , R IV , R V , R VI and R VII are independently hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph (phenyl), cyclohexyl and carbazole.

[0017] In certain embodiments of the organic molecule, R I and R IV , or R II and R III is cyclohexyl.

[0018] In certain embodiments of the organic molecule, R I and R IV , or R II and R IIIis Ph.

[0019] In certain embodiments of the organic molecule, R I and R IV , or R II and R III is Me.

[0020] In certain embodiments of the organic molecule, R I , R II , R III and R IV is hydrogen.

[0021] In a preferred embodiment of the organic molecule, R VII is Me.

[0022] In a preferred embodiment of the organic molecule, R VII is hydrogen.

[0023] In one embodiment, the organic molecule is A and R B Not just R C and R D comprises or consists of the structure of formula Ia, which is an example of a monocyclic ring system having 5 C-atoms, [ka] Chemical formula Ia Here, each R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H is independently selected from the group consisting of hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 -substituted with alkyl substituents, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 - substituted with alkyl substituents, Here, optionally, R I , R II , R III , R IV , R E , R F , R G and R H any two adjacent ones of which together form a monocyclic ring system having 5, 6, 7 or 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0024] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ia, where each R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H is independently selected from the group consisting of hydrogen, deuterium, halogen, Me, tBu, Ph, cyclohexyl, and carbazole. Here, optionally, R I , R II , R III , R IV , R E , R F , R G and R H any two adjacent ones of these together form a monocyclic ring system having 5 to 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0025] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ia, where each R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H are independently hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl and carbazole.

[0026] In one embodiment, the organic molecule is I and R IV , or R II and R III is cyclohexyl.

[0027] In one embodiment, the organic molecule is I and R IV , or R II and R III is a structure of formula Ia,

[0028] In one embodiment, the organic molecule is I and R IV , or R II and R III is Me.

[0029] In one embodiment, the organic molecule is I , R II , R III and R IV is hydrogen.

[0030] In one embodiment, the organic molecule isF and R G teeth, t The compound may comprise or consist of a structure of formula Ia, wherein R is H, R is H, and R is H.

[0031] In a preferred embodiment, the organic molecule is R VII is Me.

[0032] In a preferred embodiment, the organic molecule is R VII is hydrogen.

[0033] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, which is represented by R A and R B , R C and R D , R E and R F Not just R G and R H are examples of monocyclic ring systems having 5 C-atoms, [ka] Chemical formula Ia-2 Here, R I , R II , R III , R IV , R V , R VI and R VII are each independently selected from the group consisting of hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 -substituted with alkyl substituents, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 - substituted with alkyl substituents, Here, optionally, R I , R II , R III and R IV any two adjacent ones of which together form a monocyclic ring system having 5, 6, 7 or 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0034] In certain embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, where R I , R II , R III , R IV , R V , R VI and R VII Each independently represents hydrogen, deuterium, a halogen, Me, t selected from the group consisting of Bu, Ph, cyclohexyl and carbazole; Here, optionally, R I , R II , R III and R IV any two adjacent ones of these together form a monocyclic ring system having 5 to 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0035] In certain embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, where R I , R II , R III , R IV , R V , R VI and R VII are each independently hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl and carbazole.

[0036] In one embodiment, the organic molecule is I and R IV , or R II and R III is cyclohexyl.

[0037] In one embodiment, the organic molecule is I and R IV , or R II and R III is a structure of formula Ia-2,

[0038] In one embodiment, the organic molecule is I and R IV , or R II and R III is Me;

[0039] In one embodiment, the organic molecule is I , R II , R III and R IV is hydrogen;

[0040] In a preferred embodiment, the organic molecule is R VII is Me;

[0041] In a preferred embodiment, the organic molecule is R VII is hydrogen;

[0042] In one embodiment, the organic molecule is A and R B Not just R C and R D comprises or consists of the structure of formula Ib, which is an example of a monocyclic ring system having 6 C-atoms, [ka] Chemical formula Ib Here, each R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H are independently selected from the group consisting of hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 -substituted with alkyl substituents, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 - substituted with alkyl substituents, Here, optionally, R I , R II , R III , R IV , R E , R F , R G and R H any two adjacent ones of which together form a monocyclic ring system having 5, 6, 7 or 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0043] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ib, where each R I , R II , R III , R IV , R V , RVI , R VII , R E , R F , R G and R H is hydrogen, deuterium, halogen, Me, t independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole; Here, optionally, R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H any two adjacent ones of these together form a monocyclic ring system having 5 to 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0044] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ib, where each R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H are independently selected from the group consisting of hydrogen, deuterium, halogen, Me, tBu, Ph, cyclohexyl, and carbazole.

[0045] In one embodiment, the organic molecule is I and R IV , or R II and R III is cyclohexyl.

[0046] In one embodiment, the organic molecule is I and R IV , or RII and R III is a structure of formula Ib,

[0047] In one embodiment, the organic molecule is I and R IV , or R II and R III is Me.

[0048] In one embodiment, the organic molecule is I , R II , R III and R IV is hydrogen.

[0049] In one embodiment, the organic molecule is F and R G teeth, t The compound may comprise or consist of the structure of formula Ib, wherein:

[0050] . In a preferred embodiment, the organic molecule is R VII is Me.

[0051] In a preferred embodiment, the organic molecule is R VII is hydrogen.

[0052] In one embodiment, the organic molecule is A and R B , R C and R D , R E and R F Not just R G and R H each of which forms a monocyclic ring system having 6 C-atoms, [ka] Chemical formula Ib-2 Here, R I , R II , R III , R IV , R V , R VI and R VII are each independently selected from the group consisting of hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 -substituted with alkyl substituents, and C 3 -C 15 Heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from C 1 -C 5 - substituted with alkyl substituents, Here, optionally, R I , R II , R III and R IV any two adjacent ones of which together form a monocyclic ring system having 5, 6, 7 or 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0053] In certain embodiments, the organic molecule comprises or consists of the structure of formula Ib-2, where R I , R II , R III , R IV , R V , R VI and R VII They are hydrogen, deuterium, halogen, Me, t selected from the group consisting of Bu, Ph, cyclohexyl and carbazole; Here, optionally, R I , R II, R III and R IV any two adjacent ones of these together form a monocyclic ring system having 5 to 8 C-atoms, Here, optionally, each hydrogen may be independently replaced with Me.

[0054] In certain embodiments, the organic molecule comprises or consists of the structure of formula Ib-2, where R I , R II , R III , R IV , R V , R VI and R VII They are hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl and carbazole.

[0055] In one embodiment, the organic molecule is I and R IV , or R II and R III is cyclohexyl.

[0056] In one embodiment, the organic molecule is I and R IV , or R II and R III is Ph. The compound of the present invention comprises or consists of a structure of formula Ib-2,

[0057] In one embodiment, the organic molecule is I and R IV , or R II and R III is Me;

[0058] In one embodiment, the organic molecule is I , R II , R III and R IVis hydrogen;

[0059] In a preferred embodiment, the organic molecule is R VII is Me.

[0060] In a preferred embodiment, the organic molecule is R VII is hydrogen;

[0061] The terms "aryl" and "aromatic" as used throughout this application 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, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms is also given by the number of subscripts 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 one or more heteroatoms. The heteroatoms may be the same or different in each case and may be selected individually 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. If a group in an exemplary embodiment is defined differently from the definitions given herein, e.g., the number of aromatic ring atoms or the number of heteroatoms, the definition in the exemplary embodiment applies. According to the present invention, a fused (cyclic) aromatic or heteroaromatic polycycle is composed of two or more single aromatic or heteroaromatic rings that form a polycycle via a condensation reaction.

[0062] In particular, the term "aryl or heteroaryl group" as used throughout includes groups that may be attached via any position of an aromatic or heteroaromatic group, where the aromatic or heteroaromatic group is 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, benzyl, Derived from midazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, 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 including combinations of the foregoing groups.

[0063] As used throughout, the term "cyclic group" is understood in the broadest sense to mean any monocyclic, bicyclic or polycyclic moiety.

[0064] As used throughout, the term "biphenyl" as a substituent is also to be understood in its broadest sense as ortho-biphenyl, meta-biphenyl or para-biphenyl, where ortho, meta and para refer to and define the site of attachment to another chemical moiety.

[0065] As used throughout, the term "alkyl group" is understood in the broadest sense to mean any linear, branched or cyclic alkyl substituent. In particular, the term alkyl refers to 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 -Des-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexades-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-dodec-1-yl -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.

[0066] As used throughout, 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.

[0067] As used throughout, 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.

[0068] As used throughout, 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.

[0069] The term "thioalkoxy" as used throughout includes linear, branched and cyclic thioalkoxy substituents, where the O in the exemplary alkoxy group is replaced with S.

[0070] The terms "halogen" and "halo" as used throughout may be understood in the broadest sense, preferably fluorine, chlorine, bromine or iodine.

[0071] Whenever hydrogen (H) is mentioned herein, it can also be replaced by deuterium in each case.

[0072] When a molecular fragment is described as being a substituent or attached to another moiety, the name may be used either as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, such different ways of designating a substituent or attached fragment are considered equivalent.

[0073] In one embodiment, the organic molecules according to the present invention have an excited state lifetime of 150 μs or less, 100 μs or less, in particular 50 μs or less, more desirably 10 μs or less, or 7 μs or less in a poly(methyl methacrylate) (PMMA) film containing 5 wt % of the organic molecules at room temperature.

[0074] In one embodiment, the organic molecules according to the present invention have an excited state lifetime of 150 μs or less, 100 μs or less, particularly 50 μs or less, and more preferably 10 μs or less or 7 μs or less, in a poly(methyl methacrylate) (PMMA) film containing 1-5 wt %, particularly 2 wt %, of the organic molecules at room temperature.

[0075] In an additional embodiment of the invention, 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, at room temperature in a poly(methyl methacrylate) (PMMA) film having 5 wt % of the organic molecules, with a half width 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, and even more preferably less than 0.17 eV.

[0076] In a further embodiment of the invention, 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 half-width 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, and even more preferably less than 0.17 eV, at room temperature in a poly(methyl methacrylate) (PMMA) film having 1 to 5 wt. %, in particular 2 wt. %, of the organic molecules.

[0077] The orbitals, and excited state energies, can be determined through experimental methods. The highest occupied molecular orbital E HOMO The energy of the lowest unoccupied molecular orbital E is determined from cyclic voltammetry measurements with an accuracy of 0.1 eV by methods known to those skilled in the art. LUMO The energy of E HOMO +E gap where E gapis determined as follows: For host compounds, the onset of the emission spectrum of a poly(methyl methacrylate) film with 10 wt % host is E, unless otherwise specified. gap For the emitter molecule, E gap is determined as the energy at which the excitation and emission spectra of a film with 10% by weight of emitter intersect in PMMA. For the organic molecules according to the invention, E gap is determined as the energy at which the excitation and emission spectra intersect for a film with 5 wt. % emitter in PMMA.

[0078] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperature, typically at 77 K. For host compounds, the first excited singlet state and the lowest triplet state are energetically separated by >0.4 eV, and phosphorescence is typically visible in the steady-state spectrum of 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 77 K, measured in PMMA films with 10 wt. % emitter and 1 wt. % of the organic molecules according to the invention, unless otherwise specified. For both the host and emitter compounds, the energy of the first excited singlet state S1 is determined as the onset of the emission spectrum and, unless otherwise specified, is determined from the onset of the emission spectrum measured in a PMMA film containing 10 wt. % of the host or emitter compound and having 1 wt. % of the organic molecules according to the present invention.

[0079] 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 is set at the high energy side of the emission band and at the half width of the maximum intensity of the emission spectrum.

[0080] In one embodiment, the organic molecules according to the present invention have an emission spectrum onset that is energetically close to the emission maximum, i.e., in a poly(methyl methacrylate) (PMMA) film having 5 wt. % of the organic molecules at room temperature, the energy difference between the emission spectrum onset and the energy of the emission maximum is less than 0.14 eV, preferably less than 0.13 eV, and even more preferably less than 0.12 eV, while the full width at half maximum (FWHM) of the organic molecules is less than 0.23 eV, preferably less than 0.20 eV, and even more preferably less than 0.19 eV, and even more preferably less than 0.18 eV, and even more preferably less than 0.17 eV, resulting in a CIE y coordinate of less than 0.20, preferably less than 0.18, and even more preferably less than 0.16, and even more preferably less than 0.14.

[0081] In one embodiment, the organic molecules according to the present invention have an emission spectrum onset that is energetically close to the emission maximum, i.e., at room temperature, in a film of poly(methyl methacrylate) (PMMA) having 1-5 wt. %, in particular 2 wt. %, of the organic molecules, the energy difference between the emission spectrum onset and the energy of the emission maximum 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 is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.19 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, even more preferably less than 0.16, even more preferably less than 0.14.

[0082] Further aspects of the present invention relate to the use of the organic molecules of the present invention as luminescent emitters or luminescent absorbers, and / or as host materials and / or electron transport materials, and / or as hole injection materials and / or hole blocking materials in optoelectronic devices.

[0083] A preferred embodiment relates to the use of the organic molecules according to the invention as luminescent emitters in optoelectronic devices.

[0084] 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 nm to 800 nm, and more preferably, the optoelectronic device may be capable of emitting light in the visible range, i.e. in the wavelength range from 400 nm to 800 nm.

[0085] With respect to such applications, the optoelectronic device is more specifically selected from the group consisting of: Organic Light Emitting Diodes (OLEDs), Light-emitting electrochemical cells, OLED sensors, especially gas and vapor sensors that are not completely shielded from the surrounding environment; Organic diodes, organic solar cells, Organic transistors, Organic field effect transistors, Organic lasers, Down conversion element.

[0086] 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.

[0087] For this application, in the light-emitting layer of the optoelectronic device, more particularly in the OLED, the organic molecules according to the invention are present in an amount of 0.1% to 99% by weight, more particularly 1% to 80% by weight. In another embodiment, the proportion of the organic molecules in the light-emitting layer is 100% by weight.

[0088] In one embodiment, the emissive layer comprises not only an organic molecule according to the present invention but also a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.

[0089] 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 particular in the form of emitters and / or hosts, (b) one or more emitter and / or host substances different from the organic molecules according to the invention, and (c) optionally, one or more dyes and / or one or more solvents.

[0090] In one embodiment, the light-emitting layer comprises a composition that comprises, or consists of (or consists essentially of): (a) one or more organic molecules according to the invention, in particular in the form of emitters and / or hosts, (b) one or more emitter and / or host substances different from the organic molecules according to the invention, and (c) optionally, one or more dyes and / or one or more solvents.

[0091] In certain embodiments, the light-emitting layer (EML) comprises a composition that comprises or consists essentially 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, and (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; and (v) optionally 0-30% by weight, in particular 0-20% by weight, preferably 0-5% by weight, of at least one additional emitter molecule F having a structure different from that of the molecule according to the invention.

[0092] Desirably, energy is transferred from the host compound H to one or more organic molecules according to the invention, in particular in a first excited triplet state T1(H) of the host compound H to a first excited triplet state T1(E) of one or more organic molecules E according to the invention, and / or to a first excited singlet state S1(H) of the host compound H to a first excited singlet state S1(E) of one or more organic molecules E according to the invention.

[0093] In one embodiment, the host compound H has an energy E in the range of −5 to 6.5 eV. HOMO (H) and one or more additional host compounds D have a highest occupied molecular orbital HOMO(H) of E HOMO (D) has a highest occupied molecular orbital HOMO(D) with energy, where E HOMO (H)>E HOMO (D).

[0094] In a further embodiment, the host compound H has an energy E LUMO (H) having a lowest lying unoccupied molecular orbital LUMO(H), and one or more additional host compounds D have an energy E LUMO (D) has a lowest lying unoccupied molecular orbital LUMO(D), where E LUMO (H)>E LUMO (D).

[0095] In one embodiment, the host compound H has an energy E HOMO (H) with the highest occupied molecular orbital HOMO(H) and energy E LUMO (H) having a lowest lying unoccupied molecular orbital LUMO(H), The one or more additional host compounds D have an energy E HOMO (D) with the highest occupied molecular orbital HOMO(D) and energy E LUMO(D) having a lowest lying 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), and energy E LUMO (E) having a lowest lying unoccupied molecular orbital LUMO (E); Where: E HOMO (H)>E HOMO (D), and the energy level of the highest occupied molecular orbital HOMO (E) of the organic molecule E according to the present invention (E HOMO (E)) and the energy level of the highest occupied molecular orbital (HOMO) of the host compound (E HOMO (H)) is from -0.5 eV to 0.5 eV, more preferably from -0.3 eV to 0.3 eV, even more preferably from -0.2 eV to 0.2 eV, or even more preferably from -0.1 eV to 0.1 eV; and 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 lying unoccupied molecular orbital LUMO(D) of one or more additional host compounds 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, or even more preferably -0.1 eV to 0.1 eV.

[0096] In one embodiment of the present invention, the host compound D and / or the host compound H is a thermally activated delayed fluorescence (TADF) material. The TADF material has an energy difference ΔE between the first excited singlet state (S1) and the first excited triplet state (T1). ST The value is 2,500 cm -1 Preferably, the TADF material has a resolution of less than 3,000 cm -1 Less than 1,500 cm, preferably less than 1,500 cm -1 less than 1,000 cm, and even more preferably less than 1,000 cm -1 Less than or equal to 500cm -1Less than ΔE ST Indicates the value.

[0097] In one embodiment, host compound D is a TADF material and host compound H is a 2,500 cm -1 ΔE exceeds 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.

[0098] In one embodiment, host compound H is a TADF material and host compound D is a 2,500 cm -1 ΔE exceeds 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 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).

[0099] In a further aspect, the invention relates to an optoelectronic device comprising an organic molecule or composition of the type described therein, more particularly 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, more particularly an externally non-sealed gas and vapor sensor, an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a down conversion device.

[0100] 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.

[0101] 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.

[0102] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the composition according to the present invention as described therein.

[0103] When the optoelectronic device is an OLED, it may have, for example, the following layer structure: 1. Substrate 2. Positive electrode 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. Negative electrode layer Here, the OLED may selectively include layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each type of layer defined above.

[0104] Additionally, the optoelectronic device, in one embodiment, also includes one or more protective layers that protect the device from damaging exposure to harmful species in environments that include, for example, moisture, steam, and / or gases.

[0105] In one embodiment of the present invention, the optoelectronic device is an OLED having an inverted layer structure: 1. Substrate 2. Negative electrode 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. Positive electrode layer A Here, the OLED may optionally include layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0106] 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 can be generated by the OLED that exhibits this stacked structure, and in particular, white light can be generated by stacking blue, green and red OLEDs. The OLED that exhibits this stacked structure also includes a charge generation layer (CGL), which is generally located between two OLED subunits and is generally composed of n-doped and p-doped layers, and the n-doped layer of one CGL is closer to the positive electrode layer.

[0107] In one embodiment of the present invention, the optoelectronic device is an OLED that includes two or more emissive layers between the positive and negative electrodes. In particular, this so-called tandem OLED includes three emissive layers, where one emissive layer emits red light, one emissive layer emits green light, and one emissive layer emits blue light, and optionally further includes a charge generating layer, a blocking layer, or a transport layer between each individual emissive layer. In a further embodiment, the emissive layers are stacked adjacently. In a further embodiment, the tandem OLED includes a charge generating layer between each two emissive layers. Also, adjacent emissive layers or emissive layers separated by charge generating layers may be merged.

[0108] The substrate may be formed by 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 slide may be used, which may allow a higher level of flexibility. The positive electrode layer A is made of a material that allows obtaining a nearly (essentially) transparent film. Since at least one of the two electrodes must be (essentially) transparent to allow light emission from the OLED, one of the positive electrode layer A or the negative electrode layer C is transparent. Preferably, the positive electrode layer A contains a large content of transparent conductive oxides (TCOs) or indeed consists of them. Such a cathode layer A may include, for example, 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.

[0109] The positive electrode layer A is made of (essentially) indium tin oxide (ITO) (e.g., InO 3 ) 0.9 (SnO 2 ) 0.1 The roughness of the cathode layer A due to the transparent conductive oxide (TCO) can also be compensated for by utilizing a hole injection layer (HIL). The hole injection layer (HIL) can also facilitate 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) can be made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonate (PSS), MoO 2 , V 2 O 5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) may also prevent diffusion of metals from the cathode layer A to the hole transport layer (HTL). The HIL may be, for example, 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(phenyl) ... -(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile) and / or Spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0110] Adjacent to the cathode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport compound may be used here. For example, electron rich heteroaromatic compounds such as triarylamines and / or carbazoles may be used as hole transport compounds. The HTL may reduce the energy barrier between the cathode layer A and the emissive layer EML. The hole transport layer (HTL) may also be an electron blocking layer (EBL). Desirably, the hole transport compound has a relatively high energy level of the triplet state T1. For example, the hole transport layer (HTL) may be made of any of a variety of compounds, including tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine) (), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzeneamine]), 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, Me O-TPD, HAT-CN and / or 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,TrisPcz (9'H-3,3'-bicarbazole). The HTL may also comprise a p-doped layer consisting of an inorganic or organic dopant in an organic hole transport matrix. For example, transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may be used as inorganic dopants. For example, tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes may be used as organic dopants.

[0111] The EBL may include, for example, mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).

[0112] Adjacent to the hole transport layer (HTL) is generally located an emissive layer EML. The emissive layer EML comprises at least one emissive molecule. In particular, EML comprises one or more emissive molecules E according to the invention. In one embodiment, the emissive layer EML comprises only organic molecules according to the invention.

[0113] Typically, the EML further comprises one or more host materials H. For example, the host material H may be CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP, mCBPSif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]etheroxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, ... The host material H is generally selected from the group consisting of 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)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 exhibit a first triplet (T1) and first singlet (S1) energy level that is energetically higher than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0114] In one embodiment of the present invention, the EML comprises a so-called mixed 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 mixed host system comprising T2T as the electron-dominant host, and 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.

[0115] Adjacent to the light-emitting layer EML, an electron transport layer (ETL) may be located. Any electron transporter may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphinoxide, and sulfone 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 be NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(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. The electron transport layer (ETL) may also block holes, and a hole blocking layer (HBL) may be introduced.

[0116] Examples of HBL include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = Bathocuproine), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq 3 (aluminum-tris(8-hydroxyquinoline), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine), and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzol / 1,3,5-tris(carbazol-9-yl)benzene).

[0117] Adjacent to the electron transport layer (ETL) may be an anode layer C. The anode 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 anode layer may be composed of a metal that is not (essentially) transparent, such as Mg, Ca or Al. Alternatively or additionally, the anode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the anode layer C may also be composed of nanoscale silver wires.

[0118] The OLED may also optionally include a protective layer, also called an electron injection layer (EIL), between the electron transport layer (ETL) and the negative electrode layer C. The layer may be any of a variety of materials, including lithium fluoride, cesium fluoride, silver, Liq (8-hydroxyquinolinolatolithium), Li 2 O, BaF 2 , MgO and / or NaF.

[0119] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may also comprise one or more host compounds H.

[0120] To further modify the emission and / or absorption spectrum of the light-emitting layer (EML), the light-emitting 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. Desirably, such emitter molecules F are molecules having a structure different from that of the molecules E according to the invention. The emitter molecules F may alternatively be TADF emitters. Alternatively, the emitter molecules F may alternatively be fluorescent and / or phosphorescent emitter molecules capable of shifting the emission and / or absorption spectrum of the light-emitting layer (EML). Exemplarily, triplet and / or singlet excitons may be transferred from organic emitter molecules according to the invention to emitter molecules F before relaxing to the ground state S0, typically by emitting red-shifted light compared to the light emitted by the organic molecules. Alternatively, the emitter molecule F can also induce a two-photon effect (ie two-photon absorption at half the maximum absorbed energy).

[0121] Optionally, the optoelectronic device (e.g., an OLED) may be, for example, essentially a 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 that emit green and / or red light. Optionally, there may then also be an energy transfer between two or more molecules, as described above.

[0122] As used herein, unless more specifically defined in a particular context, the designations for the color of emitted and / or absorbed light are as follows: Purple: >380~420nm wavelength range Deep blue: wavelength range >420~480nm Sky blue: Wavelength range >480~500nm Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: >620~800nm ​​wavelength range

[0123] For emitter molecules, such hues refer to emission maxima, so for example, a deep blue emitter has an emission maximum in the range >420-480 nm, a sky blue emitter has an emission maximum in the range >480-500 nm, a green emitter has an emission maximum in the range >500-560 nm, and a red emitter has an emission maximum in the range >620-800 nm.

[0124] The deep blue emitter may desirably have an emission maximum less than 480 nm, more desirably less than 470 nm, even more desirably less than 465 nm, and even more preferably less than 460 nm. It may typically be greater than 420 nm, desirably greater than 430 nm, even more desirably greater than 440 nm, and even more preferably greater than 450 nm.

[0125] Thus, a further aspect of the invention is a 2 and / or an emission maximum at 420 nm to 500 nm, preferably at 430 nm to 490 nm, more preferably at 440 nm to 480 nm, more preferably at 450 nm to 470 nm, and / or an emission maximum at 500 cd / m 2 and preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, and even more preferably greater than 1,000 h. Accordingly, a further aspect of the invention 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, or even more preferably less than 0.15, and even more preferably less than 0.10.

[0126] Yet another aspect of the present invention relates to OLEDs that emit light at distinct color points. According to the present invention, the OLEDs emit light in a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLEDs according to the present invention emit light at a FWHM of the main emission peak that 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, and even more preferably less than 0.17 eV.

[0127] Yet another aspect of the invention relates to OLEDs that emit light at CIEx and CIEy color coordinates close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of the primary blue color (CIEx=0.131 and CIEy=0.046) defined in ITU-R Recommendation BT.2020 (Rec.2020), and thus are suitable for use in Ultra High Definition (UHD) displays, such as UHD-TVs. Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates 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, or even more preferably 0.10 to 0.15, and / or CIEy color coordinates 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.

[0128] In a further aspect, the present invention relates to a method for producing an optoelectronic component, in which the organic molecules of the present invention are used.

[0129] The optoelectronic device, in particular the OLED, according to the present invention can be produced by any deposition and / or liquid processing means. Thus, at least one layer is - Produced by the sublimation process, - Produced by organic vapor phase deposition process; - Produced by carrier gas sublimation process, -Solution processed or printed.

[0130] The methods used to manufacture the optoelectronic devices, in particular the 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 may be deposited using the same or different deposition methods.

[0131] For example, 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. Individual layers are also processed from solutions or dispersions using appropriate solvents. For example, the solution deposition processes include spin coating, dip coating and jet printing. The liquid processing is optionally carried out in an inert atmosphere (e.g., nitrogen atmosphere) and the solvent may be completely or partially removed by means known in the art. EXAMPLES

[0132] General synthesis scheme [ka] [ka] [ka] [ka]

[0133] General synthetic scheme I General synthetic scheme I provides a synthetic scheme for organic molecules according to the invention, where R I =R III and R II =R IVwhere n=0 or 1. [ka] [ka] [ka] [ka]

[0134] Synthetic Scheme II (alternative synthesis of compound I2) General synthetic scheme I provides a synthetic scheme for organic molecules according to the invention, where R I =R III , R II =R IV where n=0 or 1. [ka] [ka]

[0135] General procedure for AAV1 synthesis. [ka] E1 (1.00 equivalent), E2 (2.20 equivalent), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 ) (0.04 equivalents, CAS: 13716-12-6) and sodium tert-butoxide (NaO tBu) (3.50 equiv., CAS: 865-48-5) is stirred in toluene at 90 °C under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and saturated brine, and the phases are separated. The combined organic layer is washed with MgSO 4 After drying at rt, the solvent was removed under reduced pressure, and the resulting crude material was recrystallized or purified by column chromatography to give I1 as a solid.

[0136] General procedure for AAV2 synthesis. [ka] I1 (1.00 equivalent), E3 (2.20 equivalent), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 ) (0.04 equivalents, CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu) (3.00 equiv., CAS: 865-48-5) is stirred in toluene at 110 °C under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and saturated brine, and the phases are separated. The combined organic layer is washed with MgSO 4 After drying at rt, the solvent was removed under reduced pressure, and the resulting crude product was recrystallized or purified by column chromatography to give I2 as a solid.

[0137] General procedure for AAV3 synthesis. [ka] I2 (1 equivalent) at 0°C t Bu-benzene is stirred under a nitrogen atmosphere. tert-Butyllithium ( tBuLi, 2.2 eq., CAS 594-19-4) is added dropwise and the reaction is heated to 50° C. Trimethylborate (6 eq., CAS 121-43-7) is added slowly at room temperature to quench the lithiation reaction. The reaction mixture is heated to 60° C. for 2 hours, after which the reaction mixture is allowed to cool to room temperature. Water is added and the mixture is stirred for 2 hours. After extraction with ethyl acetate, the organic phase is washed with MgSO 4 The mixture was dried at rt and the solvent was removed under reduced pressure, and the crude product was either recrystallized or purified by column chromatography to give I3 as a solid.

[0138] General procedure for AAV4 synthesis. [ka] I3 (1 eq.) was stirred in chlorobenzene under nitrogen atmosphere. N,N-diisopropylethylamine (10.0 eq., CAS 7087-68-5) 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 equiv., 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 with DCM and water. The organic phase is diluted with MgSO 4 The mixture was dried over 100 ml and the solvent was removed under reduced pressure. The residue was recrystallized or purified by column chromatography to give P1 as a solid.

[0139] General procedure for AAV5 synthesis. [ka] E3 (1.00 equivalent), E2 (1.10 equivalent), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3, 0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 ) (0.04 equivalents, CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu) (2.00 equiv., CAS: 865-48-5) is stirred in toluene at 90 °C under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and saturated brine, and the phases are separated. The combined organic layer is washed with MgSO 4 After drying at 40° C., the solvent was removed under reduced pressure, and the resulting crude product was recrystallized or purified by column chromatography to give I1.2 as a thick oil or solid.

[0140] General procedure for AAV6 synthesis. [ka] E1 (1.00 equiv.), I1.2 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 ) (0.04 equivalents, CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu) (3.50 equiv., CAS: 865-48-5) is stirred in toluene at 110 °C under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and saturated brine, and the phases are separated. The combined organic layer is washed with MgSO 4 After drying at rt, the solvent was removed under reduced pressure, and the resulting crude product was recrystallized or purified by column chromatography to give I2 as a solid.

[0141] Cyclic Voltammetry Cyclic voltammograms are performed at concentrations of organic molecules in dichloromethane, or a suitable solvent, and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) ranging from 10 -3 The measurement is performed at room temperature under 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 ferrocene as an internal standard relative to a saturated calomel electrode (SCE).

[0142] Density functional theory calculations Molecular structures were optimized using the BP86 functional and the resolution of identity approach. Excitation energies were calculated using the (BP86) optimized structures using the Time-Dependent Density Functional Theory (TD-DFT) method. Orbitals and excited state energies were calculated by the B3LYP functional. The Def2-SVP basis set (and m4-grid for numerical integration) was used. The Turbomole program package was used for all calculations.

[0143] optical physical measurements Sample preparation: spin coating Equipment: Spin150, SPS Euro Sample concentration is 10 mg / ml dissolved in an appropriate solvent. Program: 1) 3 sec at 400 U / min, 20 sec at 1,000 U / min at 1,000 U / min. 3) 10 sec at 4,000 U / min at 1,000 U / min. After coating, the film is dried at 70° C. for 1 min.

[0144] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC) Normal-state emission spectroscopy is measured on a Horiba Scientific, Model FluoroMax-4 equipped with a 150W Xenon Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and time-correlated single photon counting option. Standard correction fitting is used to correct the emission and excitation spectra.

[0145] Excited state lifetimes are determined using the same system using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub. The excitation source is: 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).

[0146] Data analysis (exponential fitting) is performed using the software suite DataStation and DAS6 analysis software. Goodness of fit is determined using the chi-square test.

[0147] Photoluminescence quantum yield measurement For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0. The luminous mass is expressed in nm, the quantum yield Φy is expressed in %, and the CIE coordinates are expressed as x,y values. The PLQY is determined using the following protocol. 1) Quality assurance: Uses anthracene in ethanol (known concentration) as standard 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and this wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured on a solution or film sample in a nitrogen atmosphere and is calculated using the following equation:

number

[0148] Fabrication and characterization of optoelectronic devices The optoelectronic device, particularly the OLED device, comprising the organic molecules according to the present invention can be manufactured via vacuum deposition method. When a layer comprises one or more compounds, the weight percentage of one or more compounds is expressed in %. The total weight percentage value is 100%, so when no value is specified, the proportion of the compound is the same as the difference between the specified value and 100%.

[0149] OLEDs that are not fully optimized are characterized using standard methods, using electroluminescence spectra, external quantum efficiency (%) by intensity, light sensed by a photodiode, and properties calculated using current. The lifetime of an 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 is reduced to 50% of the initial luminance, similarly the LT80 value corresponds to the time when the measured luminance is reduced to 80% of the initial luminance, and the LT95 value corresponds to the time when the measured luminance is reduced to 95% of the initial luminance.

[0150] Accelerated lifetime measurements are performed (e.g., applying increased current densities). For example, 500 cd / m 2 In the present invention, the LT80 value is determined using the following equation:

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[0151] HPLC-MS The HPLC-MS analysis is carried out on an Agilent (1100 series) HPLC with an MS-detector (Thermo LTQXL). A typical HPLC method is as follows: Reverse phase column 4.6mm x 150mm A particle size of 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6 × 150 mm, 3.5 μm HPLC column) is used for HPLC. The HPLC-MS measurements are performed at room temperature (rt) with a gradient. [Table 1] The following solvent mixtures are used: [Table 2] In an analyte solution of 0.5 mg / mL concentration, an injection volume of 5 μL is taken for the measurement.

[0152] The ionization of the probe is positive (APCI + ) or negative (APCI - ) ionization mode using an atmospheric pressure chemical ionization (APCI) source.

[0153] Example 1 [ka] Example 1 was synthesized as follows. AAV1 (91% yield), in which 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) was used as reactant E1 and 1,2,3,5,6,7-hexahydro-S-5-indacen-4-yl-amine (CAS: 63089-56-5) was used as reactant E2; AAV2 (63% yield), where 1-bromo-4-tert-butylbenzene (CAS: 3972-65-4) was used as reactant E3; AAV3 and AAV4 (18% yield in two steps).

[0154] MS (HPLC-MS), m / z (residence time): 693.6 (8.23 minutes)

[0155] The emission maximum of Example 1 (2% by weight of PMMA) is 458 nm, the full width at half maximum (FWHM) is 0.15 eV, and the CIEx and CIEy coordinates are 0.14 and 0.08, respectively.

[0156] Additional Examples of Organic Molecules of the Invention (See: In the structure shown, t Bu indicates a tertiary butyl group attached, the following materials are equivalent: [ka] [ka]

[0157] Also, Ph represents a bound phenyl group, and the following materials are equivalent: [ka] [ka]

[0158] [ka]

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Claims

1. An organic molecule represented by any one of the following compounds: 【Chemistry 1】 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】

2. 10. Use of the organic molecule according to claim 1 as a light emitter in an optoelectronic device.

3. The use of organic molecules according to claim 1 , wherein the optoelectronic device is selected from the group consisting of: Organic Light Emitting Diodes (OLEDs), Light-emitting electrochemical cells, OLED sensor, Organic diodes, organic solar cells, Organic transistors, Organic field effect transistors, Organic lasers, and Down-conversion element.

4. (a) the organic molecule according to claim 1 in the form of an emitter and / or a host; (b) emitter and / or host materials that are different from the organic molecules; and (c) optionally, a dye and / or a solvent.

5. 10. An optoelectronic device comprising the organic molecule of claim 1 or the composition of claim 4, and having a device form selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical device, 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 device.

6. -substrate, - positive electrode, a negative electrode, where the positive electrode or the negative electrode is disposed on a substrate, and An optoelectronic device according to claim 5, comprising: a light-emitting layer, the light-emitting layer being disposed between a positive electrode and a negative electrode and comprising said organic molecule or said composition.

7. A method for producing an optoelectronic device, in which the organic molecule described in claim 1 or the composition described in claim 4 is used.

8. The method of claim 7 , comprising processing the organic molecules by vacuum evaporation or from a solution.

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