Organic Molecules for Optoelectronic Devices

Abstract

The invention relates to organic molecules (specifically, applied in optoelectronic devices). According to the invention, the organic molecule has a structure of formula I, wherein: R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R 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; halogen; C1-C 12 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 ; C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 ; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 ; optionally, any two adjacent ones of 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 form a monocyclic ring system having 5 to 8 C atoms, at least R A and R B and R C and R D form a monocyclic ring system having 5 to 8 C atoms, wherein optionally each hydrogen can be independently replaced by each other. #imgabs0#

Description

Technical Field

[0001] The invention relates to organic light-emitting molecules and to the use of organic light-emitting molecules in organic light-emitting diodes (OLEDs) and in other optoelectronic devices. Background Art

[0002] The use of organic molecules in optoelectronic devices is being actively developed. Summary of the Invention

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

[0004] This object is achieved by an invention which provides a novel organic molecule.

[0005] According to the invention, the organic molecule is a purely organic molecule, i.e., it does not contain any metal ions compared to metal complexes known for use in optoelectronic devices. However, the organic molecule of the invention includes a metalloid (specifically, B, Si, Sn, Se, and / or Ge).

[0006] According to the present invention, the organic molecule exhibits an emission maximum in the blue spectral range, sky-blue spectral range, or green spectral range. Specifically, the organic molecule exhibits an emission maximum between 420 nm and 520 nm (preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm). Specifically, the photoluminescence quantum yield of the organic molecule according to the invention is 50% or greater. Using the organic molecule according to the invention in an optoelectronic device (e.g., an organic light-emitting diode (OLED)) results in a higher efficiency or higher color purity (which is expressed by the full width at half maximum (FWHM) of the emission) of the optoelectronic device. The corresponding OLED has a higher stability than an OLED having a known emitter material and comparable color.

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

[0008]

[0009] wherein 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 HIndependently selected from the group consisting of: hydrogen; deuterium; halogen; C1-C 12 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 ; C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 ; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by R 5 .

[0010] R 5 is independently selected from the group consisting of: hydrogen; deuterium; halogen; C1-C 12 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by R 6 ; C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by R 6 ; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by R 6 .

[0011] R 6 is independently selected from the group consisting of: hydrogen; deuterium; halogen; C1-C 12 alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by C1-C5 alkyl substituents; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by C1-C5 alkyl substituents.

[0012] Any two adjacent ones of the 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 in the organic molecule can form a monocyclic ring system having 5, 6, 7 or 8 carbon atoms.

[0013] At least R A and R B and R C and RD A monocyclic ring system having 5, 6, 7 or 8 C atoms is formed, wherein optionally each hydrogen can be independently substituted by R for each other. 6 Substituted.

[0014] Optionally, each hydrogen of the organic molecule is independently substituted by deuterium or a halogen.

[0015] In some embodiments of the organic molecule, R I , R II , R III , R IV , R V , R VI and R VII each independently selected from the group consisting of: hydrogen; deuterium; halogen; C1-C 12 alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently substituted by a C1-C5 alkyl substituent; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently substituted by a C1-C5 alkyl substituent;

[0016] wherein optionally any two adjacent ones of R I , R II , R III and R IV (i.e., R I and R II and / or R III and R IV ) together form a monocyclic ring system having 5 to 8 C atoms (i.e., 5, 6, 7 or 8 carbon atoms), wherein optionally each hydrogen can be independently substituted by methyl (Me).

[0017] The term "monocyclic ring system" specifically refers to a non-aromatic ring system.

[0018] In some embodiments of the organic molecule, R I , R II , R III , R IV , R V , R VI and R VII each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph (phenyl), cyclohexyl and carbazolyl,

[0019] wherein optionally R I , R II , R III and R IVAny two adjacent ones of them together form a monocyclic ring system having 5 to 8 C atoms, wherein, optionally, each hydrogen can be independently replaced by Me with respect to each other.

[0020] In some embodiments of the organic molecule, R I 、R II 、R III 、R IV 、R V 、R VI and R VII each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl, and carbazolyl.

[0021] In some embodiments of the organic molecule, R I and R IV or R II and R III are cyclohexyl.

[0022] In some embodiments of the organic molecule, R I and R IV or R II and R III are Ph.

[0023] In some embodiments of the organic molecule, R I and R IV or R II and R III are Me.

[0024] In some embodiments of the organic molecule, R I 、R II 、R III and R IV are hydrogen.

[0025] In a preferred embodiment of the organic molecule, R VII is Me.

[0026] In a preferred embodiment of the organic molecule, R VII is hydrogen.

[0027] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia, and the structure of formula Ia is an example for R A and R B and R C and R D to form a monocyclic ring system having 5 C atoms:

[0028]

[0029] wherein, R I, R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H each independently selected from the group consisting of: hydrogen; deuterium; halogen; C1-C 12 alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently substituted with C1-C5 alkyl substituents; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently substituted with C1-C5 alkyl substituents;

[0030] wherein 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, wherein optionally each hydrogen may be independently substituted with Me by each other.

[0031] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl and carbazolyl,

[0032] wherein 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 to 8 C atoms, wherein optionally each hydrogen may be independently substituted with Me by each other.

[0033] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl, and carbazolyl.

[0034] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R I and R IV or R II and R III is cyclohexyl.

[0035] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R I and R IV or R II and R III is Ph.

[0036] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R I and R IV or R II and R III is Me.

[0037] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R I , R II , R III and R IV is hydrogen.

[0038] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia, wherein R F and R G is t Bu.

[0039] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, wherein R VII is Me.

[0040] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Ia, wherein R VII is hydrogen.

[0041] In one embodiment, the organic molecule comprises or consists of a structure of formula Ia-2, and the structure of formula Ia-2 is for R A and R B 、R C and R D 、R E and R F as well as R G and R H to form examples of a monocyclic ring system having 5 carbon atoms:

[0042]

[0043] wherein each of 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; C1-C 12 alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by C1-C5 alkyl substituents; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by C1-C5 alkyl substituents;

[0044] wherein optionally any two adjacent ones of R I 、R II 、R III and R IV together form a monocyclic ring system having 5, 6, 7 or 8 carbon atoms, wherein optionally each hydrogen can be independently replaced by Me.

[0045] In some embodiments, the organic molecule comprises or consists of a structure of formula Ia-2, wherein each of 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, t Bu, Ph, cyclohexyl and carbazolyl,

[0046] wherein optionally, RI , R II , R III and R IV Any two adjacent ones of and R form a monocyclic ring system having 5 to 8 C atoms, wherein, optionally, each hydrogen can be independently replaced by Me with respect to each other.

[0047] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R I , R II , R III , R IV , R V , R VI and R VII each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl and carbazolyl.

[0048] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R I and R IV or R II and R III are cyclohexyl.

[0049] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R I and R IV or R II and R III are Ph.

[0050] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R I and R IV or R II and R III are Me.

[0051] In some embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R I , R II , R III and R IV are hydrogen.

[0052] In preferred embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R VII is Me.

[0053] In preferred embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, wherein R VIIis hydrogen.

[0054] In one embodiment, the organic molecule comprises or consists of the structure of formula Ib, the structure of formula Ib being wherein R A and R B and R C and R D Examples of forming a monocyclic ring system having 6 C atoms:

[0055]

[0056] wherein, R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H each independently selected from the group consisting of: hydrogen; deuterium; halogen; C1-C 12 alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by a C1-C5 alkyl substituent; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by a C1-C5 alkyl substituent;

[0057] wherein optionally, any two adjacent ones of R I , R II , R III , R IV , R E , R F , R G and R H together form a monocyclic ring system having 5, 6, 7 or 8 C atoms, wherein optionally each hydrogen can be independently replaced by Me.

[0058] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib, wherein R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H each independently selected from hydrogen, deuterium, halogen, Me, tThe group consisting of Bu, Ph, cyclohexyl, and carbazolyl

[0059] wherein, 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 to 8 C atoms, wherein, optionally, each hydrogen can be independently replaced by Me with respect to each other.

[0060] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib, wherein R I , R II , R III , R IV , R V , R VI , R VII , R E , R F , R G and R H are each independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl, and carbazolyl.

[0061] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib, wherein R I and R IV or R II and R III are cyclohexyl.

[0062] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib, wherein R I and R IV or R II and R III are Ph.

[0063] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib, wherein R I and R IV or R II and R III are Me.

[0064] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib, wherein R I , R II , R III and R IV are hydrogen.

[0065] In some embodiments, the organic molecule comprises or consists of the structure of Formula Ib, wherein R F and R G is t Bu.

[0066] In a preferred embodiment, the organic molecule comprises or consists of the structure of Formula Ib, wherein R VII is Me.

[0067] In a preferred embodiment, the organic molecule comprises or consists of the structure of Formula Ib, wherein R VII is hydrogen.

[0068] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib-2, and the structure of Formula Ib-2 is an example where R A and R B , R C and R D , R E and R F as well as R G and R H each form a monocyclic ring system having 6 C atoms:

[0069]

[0070] wherein each of 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; C1-C 12 alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced by a C1-C5 alkyl substituent; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced by a C1-C5 alkyl substituent;

[0071] wherein optionally, any two adjacent ones of R I , R II , R III and R IV together form a monocyclic ring system having 5, 6, 7 or 8 C atoms, wherein optionally each hydrogen can be independently replaced by Me.

[0072] In some embodiments, the organic molecule comprises or consists of a structure of Formula Ib-2, wherein 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, Me, t Bu, Ph, cyclohexyl, and carbazolyl,

[0073] wherein optionally, any two adjacent ones of R I , R II , R III , and R IV together form a monocyclic ring system having 5 to 8 C atoms, wherein optionally each hydrogen can be independently replaced by Me.

[0074] In some embodiments, the organic molecule comprises or consists of a structure of Formula Ib-2, wherein 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, Me, t Bu, Ph, cyclohexyl, and carbazolyl.

[0075] In some embodiments, the organic molecule comprises or consists of a structure of Formula Ib-2, wherein R I and R IV or R II and R III are cyclohexyl.

[0076] In some embodiments, the organic molecule comprises or consists of a structure of Formula Ib-2, wherein R I and R IV or R II and R III are Ph.

[0077] In some embodiments, the organic molecule comprises or consists of a structure of Formula Ib-2, wherein R I and R IV or R II and R III are Me.

[0078] In some embodiments, the organic molecule comprises or consists of the structure of Formula Ib-2, wherein R I 、R II 、R III and R IV are hydrogen.

[0079] In preferred embodiments, the organic molecule comprises or consists of the structure of Formula Ib-2, wherein R VII is Me.

[0080] In preferred embodiments, the organic molecule comprises or consists of the structure of Formula Ib-2, wherein R VII is hydrogen. BRIEF DESCRIPTION OF THE DRAWINGS

[0081] Figure 1 : Emission spectrum of Example 1 (2 wt%) in PMMA. DETAILED DESCRIPTION

[0082] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense to mean any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, aryl contains from 6 to 60 aromatic ring atoms, and heteroaryl contains from 5 to 60 aromatic ring atoms at least one of which is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms may be given as a subscript number in the definition of certain substituents. Specifically, the heteroaromatic ring contains from one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense to include any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatoms may be the same or different each time they occur and may be independently selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent having two points of attachment to other molecular structures and thus serving as a linking group structure. In the case where 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 is different from the given definition), the definition in the exemplary embodiment will apply. According to the invention, a condensed (cyclized) aromatic polycycle or heteroaromatic polycycle is composed of two or more monocyclic aromatic rings or heteroaromatic rings that form a polycycle via a condensation reaction.

[0083] Specifically, as used throughout, the term "aryl or heteroaryl" includes groups that can be attached at any position via an aromatic group or a heteroaromatic group, and the group is derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, Perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridinimidazole, pyrazinimidazole, quinoxalinimidazole, 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 combinations of the above groups.

[0084] As used throughout, the term "ring group" can be understood in the broadest sense to mean any monocyclic moiety, bicyclic moiety or polycyclic moiety.

[0085] As used throughout, the term "biphenyl" as a substituent can be understood in the broadest sense to mean o-biphenyl, m-biphenyl or p-biphenyl, where o, m and p are defined with respect to the binding site to another chemical moiety.

[0086] As used throughout, the term "alkyl" can be understood in the broadest sense to mean any straight-chain, branched-chain or cyclic alkyl substituent. Specifically, the term alkyl includes substituents such as methyl (Me), ethyl (Et), n-propyl ( n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-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-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.

[0087] As used throughout, the term "alkenyl" includes straight-chain, branched-chain, and cyclic alkenyl substituents. The term "alkenyl" includes, for example, substituents such as vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

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

[0089] As used throughout, the term "alkoxy" includes straight-chain, branched-chain, and cyclic alkoxy substituents. Exemplary alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and 2-methylbutoxy.

[0090] As used throughout, the term "thioalkoxy" includes straight-chain, branched-chain, and cyclic thioalkoxy substituents in which, for example, the O of the alkoxy is replaced by S.

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

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

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

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

[0095] In one embodiment, the organic molecule according to the invention has an excited state lifetime of no more than 150 μs, no more than 100 μs, specifically no more than 50 μs, more preferably no more than 10 μs or no more than 7 μs at room temperature in a film of poly(methyl methacrylate) (PMMA) having 1 wt% to 5 wt% (specifically, having 2 wt%) of the organic molecule.

[0096] In yet another embodiment of the invention, the organic molecule according to the invention has an emission peak in the visible light or near-ultraviolet range (i.e., in the wavelength range of 380 nm to 800 nm) and a full width at half maximum 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) at room temperature in a film of poly(methyl methacrylate) (PMMA) having 5 wt% of the organic molecule.

[0097] In yet another embodiment of the invention, the organic molecule according to the invention has an emission peak in the visible light or near-ultraviolet range (i.e., in the wavelength range of 380 nm to 800 nm) and a full width at half maximum 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) at room temperature in a film of poly(methyl methacrylate) (PMMA) having 1 wt% to 5 wt% (specifically, having 2 wt%) of the organic molecule.

[0098] Orbital and excited state energies can also be determined by means of experimental methods. The highest occupied molecular orbital energy (EHOMO ) Determined by cyclic voltammetry measurement with an accuracy of 0.1 eV via a method known to those skilled in the art. The lowest unoccupied molecular orbital energy (E LUMO ) is calculated as E HOMO + E gap , where E gap is determined as follows: For the host compound, unless otherwise stated, the starting point of the emission spectrum of a film with 10 wt% host in poly(methyl methacrylate) (PMMA) is used as E gap . For the emitter molecule, E gap is determined as the energy at which the excitation spectrum and the emission spectrum of a film with 10 wt% emitter in PMMA cross. For the organic molecules according to the invention, E gap is determined as the energy at which the excitation spectrum and the emission spectrum of a film with 5 wt% organic molecules according to the invention in PMMA cross.

[0099] The energy of the first excited triplet state T1 is determined by the starting point of the emission spectrum at low temperature (usually, at 77 K). For host compounds where the first excited singlet state and the lowest triplet state differ in energy by > 0.4 eV, phosphorescence is usually visible in the steady-state spectrum in 2-methyl-tetrahydrofuran (2-Me-THF). Thus, the triplet energy can be determined as the starting point of the phosphorescence spectrum. For TADF emitter molecules, unless otherwise stated, the energy of the first excited triplet state T1 is determined by the starting point of the delayed emission spectrum at 77 K, which is measured in a PMMA film with 10 wt% emitter and, in the case of the organic molecules according to the invention, 1 wt% of the organic molecules according to the invention. For both host and emitter compounds, unless otherwise stated, the energy of the first excited singlet state S1 is determined by the starting point of the emission spectrum, which is measured in a PMMA film with 10 wt% host or emitter compound and, in the case of the organic molecules according to the invention, 1 wt% of the organic molecules according to the invention.

[0100] The starting point of the emission spectrum is determined by calculating the intersection of the tangent of the emission spectrum with the x-axis. The tangent of the emission spectrum is set at the high-energy side of the emission band and at the point of half maximum of the maximum intensity of the emission spectrum.

[0101] In one embodiment, the organic molecule according to the invention has, at room temperature, an emission spectrum with a starting point that is energetically close to the emission maximum in a film of poly(methyl methacrylate) (PMMA) having 5 wt% of the organic molecule, i.e., the energy difference between the starting point of the emission spectrum 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 molecule is less than 0.23 eV (preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV), such that the CIEy coordinate is less than 0.20 (preferably less than 0.18, more preferably less than 0.16, or even more preferably less than 0.14).

[0102] In one embodiment, the organic molecule according to the invention has, at room temperature, an emission spectrum with a starting point that is energetically close to the emission maximum in a film of poly(methyl methacrylate) (PMMA) having 1 wt% to 5 wt% (specifically, having 2 wt%) of the organic molecule, i.e., the energy difference between the starting point of the emission spectrum 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 molecule is less than 0.23 eV (preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV), such that the CIEy coordinate is less than 0.20 (preferably less than 0.18, more preferably less than 0.16, or even more preferably less than 0.14).

[0103] Another aspect of the invention relates to the use of the organic molecule of the invention as a light-emitting emitter or as an absorber and / or as a host material and / or as an electron transport material and / or as a hole injection material and / or as a hole blocking material in optoelectronic devices.

[0104] A preferred embodiment relates to the use of the organic molecule according to the invention as a light-emitting emitter in optoelectronic devices.

[0105] An optoelectronic device can be understood in the broadest sense as any device based on an organic material that is suitable for emitting visible light or light in the range closest to the ultraviolet (UV) range (i.e., in the wavelength range of 380 nm to 800 nm). More preferably, the optoelectronic device can be capable of emitting light in the visible light range (i.e., 400 nm to 800 nm).

[0106] In the context of such applications, optoelectronic devices are more specifically selected from the group consisting of:

[0107] · Organic light-emitting diodes (OLEDs);

[0108] · Light-emitting electrochemical cells;

[0109] · OLED sensors, especially gas and vapor sensors not hermetically isolated from the surrounding environment;

[0110] · Organic diodes;

[0111] · Organic solar cells;

[0112] · Organic transistors;

[0113] · Organic field-effect transistors;

[0114] · Organic lasers; and

[0115] · Down-conversion elements.

[0116] In a preferred embodiment in the context of such applications, the optoelectronic device is a device selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0117] In the case of this application, the fraction of the organic molecules according to the invention in the emission layer of the optoelectronic device (more specifically, in the OLED) is 0.1 wt% to 99 wt% (more specifically, 1 wt% to 80 wt%). In an alternative embodiment, the proportion of the organic molecules in the emission layer is 100 wt%.

[0118] In one embodiment, the light-emitting layer (or referred to as the "emission layer") includes not only the organic molecules according to the invention but also a host material whose triplet (T1) energy level and singlet (S1) energy level are higher in energy than the triplet (T1) energy level and singlet (S1) energy level of the organic molecules.

[0119] Another aspect of the invention relates to a composition that comprises or consists of the following components:

[0120] (a) at least one organic molecule according to the invention, specifically in the form of an emitter and / or a host;

[0121] (b) one or more emitter and / or host materials different from the organic molecules according to the invention; and

[0122] (c) optionally, one or more dyes and / or one or more solvents.

[0123] In one embodiment, the light-emitting layer comprises (or consists essentially of) a composition that comprises or consists of the following components:

[0124] (a) at least one organic molecule according to the invention, specifically in the form of an emitter and / or a host;

[0125] (b) one or more emitters and / or host materials different from the organic molecule according to the invention; and

[0126] (c) optionally, one or more dyes and / or one or more solvents.

[0127] In a specific embodiment, the emitting layer (EML) comprises a composition (or consists essentially of a composition), which composition comprises the following components or consists of the following components:

[0128] (i) 0.1 wt% to 10 wt% (preferably 0.5 wt% to 5 wt%, specifically 1 wt% to 3 wt%) of one or more organic molecules (E) according to the invention;

[0129] (ii) 5 wt% to 99 wt% (preferably 15 wt% to 85 wt%, specifically 20 wt% to 75 wt%) of at least one host compound (H); and

[0130] (iii) 0.9 wt% to 94.9 wt% (preferably 14.5 wt% to 80 wt%, specifically 24 wt% to 77 wt%) of at least one other host compound (D), which other host compound (D) has a structure different from the structure of the organic molecule according to the invention; and

[0131] (iv) optionally, 0 wt% to 94 wt% (preferably 0 wt% to 65 wt%, specifically 0 wt% to 50 wt%) of a solvent; and

[0132] (v) optionally, 0 wt% to 30 wt% (specifically 0 wt% to 20 wt%, preferably 0 wt% to 5 wt%) of at least one other emitter molecule (F), which other emitter molecule (F) has a structure different from the structure of the organic molecule according to the invention.

[0133] Preferably, energy can be transferred from the host compound (H) to one or more organic molecules according to the invention. Specifically, energy can be transferred 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.

[0134] In one embodiment, the host compound (H) has an energy (E) in the range of -5 eV to -6.5 eV HOMO(H)) of the highest occupied molecular orbital (HOMO(H)), at least one other host compound (D) has a highest occupied molecular orbital (HOMO(D)) with an energy of E HOMO (D)), where E HOMO (H) > E HOMO (D).

[0135] In yet another embodiment, the host compound (H) has a lowest unoccupied molecular orbital (LUMO(H)) with an energy of E LUMO (H)), at least one other host compound (D) has a lowest unoccupied molecular orbital (LUMO(D)) with an energy of E LUMO (D)), where E LUMO (H) > E LUMO (D).

[0136] In one embodiment, the host compound (H) has a highest occupied molecular orbital (HOMO(H)) with an energy of E HOMO (H)) and a lowest unoccupied molecular orbital (LUMO(H)) with an energy of E LUMO (H)), and

[0137] at least one other host compound (D) has a highest occupied molecular orbital (HOMO(D)) with an energy of E HOMO (D)) and a lowest unoccupied molecular orbital (LUMO(D)) with an energy of E LUMO (D)),

[0138] The organic molecule (E) according to the invention has a highest occupied molecular orbital (HOMO(E)) with an energy of E HOMO (E)) and a lowest unoccupied molecular orbital (LUMO(E)) with an energy of E LUMO (E)),

[0139] wherein,

[0140] E HOMO (H) > E HOMO (D), and the energy level (E HOMO (E)) of the highest occupied molecular orbital (HOMO(E)) of the organic molecule (E) according to the invention and the energy level (E HOMO (H)) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) differ by between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0141] E LUMO(H) > E LUMO (D), and according to the energy level (E LUMO (E)) of the lowest unoccupied molecular orbital (LUMO(E)) of the organic molecule (E) of the invention and the energy level (E LUMO (D)) of the lowest unoccupied molecular orbital (LUMO(D)) of at least one other host compound D, the difference therebetween is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0142] In one embodiment of the invention, the host compound (D) and / or the host compound (H) is a thermally activated delayed fluorescence (TADF) material. The TADF material exhibits a ΔE -1 value corresponding to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) of less than 2500 cm ST . Preferably, the TADF material exhibits a ΔE -1 of less than 3000 cm -1 , more preferably less than 1500 cm -1 , even more preferably less than 1000 cm -1 or even less than 500 cm ST .

[0143] In one embodiment, the host compound (D) is a TADF material, and the host compound (H) exhibits a ΔE -1 value greater than 2500 cm ST . In a specific 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-(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.

[0144] In one embodiment, the host compound (H) is a TADF material, and the host compound (D) exhibits a ΔE -1 value greater than 2500 cm ST . In a specific 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'-spirobifluorene-2-yl)-1,3,5-triazine).

[0145] In yet another aspect, the invention relates to an optoelectronic device comprising an organic molecule as described herein or a composition of the type described herein, the optoelectronic device being 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, a gas and vapor sensor hermetically isolated externally), an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a down-conversion element.

[0146] 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.

[0147] In one embodiment of the optoelectronic device of the invention, the organic molecule (E) according to the invention is used as the emitting material in the emitting layer (EML).

[0148] In one embodiment of the optoelectronic device of the invention, the emitting layer (EML) consists of the composition according to the invention as described herein.

[0149] When the optoelectronic device is an OLED, it may for example have the following layer structure:

[0150] 1. Substrate

[0151] 2. Anode layer, A

[0152] 3. Hole injection layer, HIL

[0153] 4. Hole transport layer, HTL

[0154] 5. Electron blocking layer, EBL

[0155] 6. Emitting layer, EML

[0156] 7. Hole blocking layer, HBL

[0157] 8. Electron transport layer, ETL

[0158] 9. Electron injection layer, EIL

[0159] 10. Cathode layer, C

[0160] Wherein, the OLED comprises each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and optionally, different layers may be combined, and the OLED may comprise more than one layer of each layer type defined above.

[0161] In addition, in one embodiment, the optoelectronic device may include one or more protective layers that protect the device from damage due to exposure to harmful substances in the environment, including, for example, moisture, vapor, and / or gas.

[0162] In one embodiment of the invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0163] 1. Substrate

[0164] 2. Cathode layer, C

[0165] 3. Electron injection layer, EIL

[0166] 4. Electron transport layer, ETL

[0167] 5. Hole blocking layer, HBL

[0168] 6. Emission layer, EML

[0169] 7. Electron blocking layer, EBL

[0170] 8. Hole transport layer, HTL

[0171] 9. Hole injection layer, HIL

[0172] 10. Anode layer, A

[0173] Wherein, the OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL. Optionally only, different layers may be combined, and the OLED may include more than one layer of each layer type defined above.

[0174] In one embodiment of the invention, the optoelectronic device is an OLED that may have a stacked architecture. In this architecture, contrary to the typical arrangement in which OLEDs are placed side by side, the individual units are stacked on top of each other. Mixed light can be generated with an OLED exhibiting a stacked architecture. Specifically, white light can be generated by stacking a blue OLED, a green OLED, and a red OLED. In addition, an OLED exhibiting a stacked architecture may include a charge generation layer (CGL), which is typically positioned between two OLED sub-units and typically consists of an n-doped layer and a p-doped layer, and the n-doped layer of one CGL is typically positioned close to the anode layer.

[0175] In one embodiment of the invention, the optoelectronic device is an OLED comprising two or more emission layers between an anode and a cathode. Specifically, such a so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light, and one emission layer emits blue light, and optionally may further comprise layers such as charge generation layers, blocking layers or transport layers between the respective emission layers. In yet another embodiment, the emission layers are stacked adjacent to each other. In yet another embodiment, the tandem OLED comprises a charge generation layer between every two emission layers. Additionally, adjacent emission layers or emission layers separated by a charge generation layer may be combined.

[0176] The substrate may be formed of any material or combination of materials. Most commonly, a glass slide is used as the substrate. Optionally, a thin metal layer (e.g., a copper, gold, silver or aluminum film) or a plastic film or glass slide may be used. This may allow a higher degree of flexibility. The anode layer (A) mainly consists of a material that allows for the obtaining of a (substantially) transparent film. Since at least one of the two electrodes should be (substantially) transparent to allow light to be emitted from the OLED, either the anode layer (A) or the cathode layer (C) is transparent. Preferably, the anode layer (A) comprises a large amount of transparent conductive oxide (TCO), or even consists of transparent conductive oxide (TCO). Such an anode 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.

[0177] The anode layer (A) may (substantially) consist of indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1)It is composed of. The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). In addition, since the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is promoted, the HIL can promote the injection of quasi-charge carriers (i.e., holes). The hole injection layer (HIL) can include poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC, or CuI (specifically, a mixture of PEDOT and PSS). The hole injection layer (HIL) can also prevent the diffusion of metal from the anode layer (A) into the hole transport layer (HTL). The HIL can include, for example, PEDOT:PSS (poly-3,4-ethylenedioxythiophene:polystyrene sulfonate), PEDOT (poly-3,4-ethylenedioxythiophene), mMTDATA (4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetra(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine)), NPB (N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile), and / or spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0178] Adjacent to the anode layer (A) or the hole injection layer (HIL), typically a hole transport layer (HTL) is positioned. Here, any hole transport compound can be used. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer (A) and the emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a rather high energy level of its triplet state T1. For example, the hole transport layer (HTL) can include star-shaped heterocycles such as tris(4-carbazol-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), α-NPD (2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine), TAPC (4,4'-cyclohexyl-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or triPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, the HTL can include a p-doped layer that can be composed of an inorganic dopant or an organic dopant in an organic hole transport matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide can be used, for example, as inorganic dopants. Tetracyanoquinodimethane (F4-TCNQ), copper(I) pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used, for example, as organic dopants.

[0179] The EBL can include, for example, mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), triPcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).

[0180] Adjacent to the hole transport layer (HTL), a light emitting layer (EML) is typically positioned. The light emitting layer (EML) includes at least one light emitting molecule. Specifically, the EML includes at least one light emitting molecule (E) according to the invention. In one embodiment, the light emitting layer includes only organic molecules according to the invention. Typically, the EML additionally includes one or more host materials (H). For example, the host material (H) is selected from CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP, mCBP, Sif87 (dibenzothiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzothiophen-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran)-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-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'-spirobifluorene-2-yl)-1,3,5-triazine). The host material (H) should typically be selected to exhibit a first triplet (T1) and a first singlet (S1) energy level that is higher in energy than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0181] In one embodiment of the invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML exactly comprises a luminescent organic molecule according to the invention and a hybrid host system, which hybrid host system comprises T2T as the electron-dominant host and a host selected from CBP, mCP, mCBP, 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 yet another embodiment, the EML comprises 50 wt% to 80 wt% (preferably, 60 wt% to 75 wt%) of a host, 10 wt% to 45 wt% (preferably, 15 wt% to 30 wt%) of T2T, and 5 wt% to 40 wt% (preferably, 10 wt% to 30 wt%) of the luminescent molecule according to the invention, and the host is selected from CBP, mCP, mCBP, 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.

[0182] Adjacent to the luminescent layer EML, an electron transport layer (ETL) may be positioned. Here, any electron transport agent can be used. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide and sulfone can be used. The electron transport body can also be a star heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). The ETL may comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), Sif87 (dibenzothiophen-2-yl)triphenylsilane), Sif88 ((dibenzothiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-bis(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) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0183] The HBL may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), BAlq (bis(8-hydroxy-2-methylquinolinato)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinolinato)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), 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'-spirobifluorene-2-yl)-1,3,5-triazine), and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene).

[0184] Adjacent to the electron transport layer (ETL), a cathode layer (C) may be positioned. The cathode layer (C) may include, for example, a metal (such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or may consist of a metal (such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also consist of a (substantially) opaque metal such as Mg, Ca, or Al. Optionally or additionally, the cathode layer (C) may also include graphite and / or carbon nanotubes (CNT). Optionally, the cathode layer (C) may also consist of nanoscale silver wires.

[0185] The OLED may further optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (lithium 8-hydroxyquinolate), Li2O, BaF2, MgO, and / or NaF.

[0186] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may also include one or more host compounds (H).

[0187] In order to further modify the emission spectrum and / or absorption spectrum of the emissive layer (EML), the emissive layer EML may further comprise one or more other emitter molecules (F). Such emitter molecules (F) may be any emitter molecules known in the art. Preferably, such emitter molecules (F) are molecules having a structure different from the structure of the organic molecule (E) according to the invention. Optionally, the emitter molecule (F) may be a TADF emitter. Optionally, the emitter molecule (F) may optionally be a fluorescent and / or phosphorescent emitter molecule capable of shifting the emission spectrum and / or absorption spectrum of the emissive layer (EML). Exemplarily, by emitting light that is typically redshifted compared to the light emitted by the organic molecule, triplet and / or singlet excitons may be transferred from the organic emitter molecule according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Optionally, the emitter molecule (F) may also cause a two-photon effect (i.e., the absorption of two photons at half the energy of the absorption maximum).

[0188] Optionally, an optoelectronic device (e.g., an OLED) may be, for example, a substantially white optoelectronic device. For example, such a white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green light and / or red light. Then, energy transmittance may also optionally exist between two or more molecules as described above.

[0189] As used herein, if not more specifically defined in a particular context, the designation of the color of emitted and / or absorbed light is as follows:

[0190] Violet: wavelength range of >380 nm to 420 nm;

[0191] Deep blue: wavelength range of >420 nm to 480 nm;

[0192] Sky blue: wavelength range of >480 nm to 500 nm;

[0193] Green: wavelength range of >500 nm to 560 nm;

[0194] Yellow: wavelength range of >560 nm to 580 nm;

[0195] Orange: wavelength range of >580 nm to 620 nm;

[0196] Red: wavelength range of >620 nm to 800 nm.

[0197] For emitter molecules, this color refers to the emission maximum. Thus, for example, a dark blue emitter has an emission maximum in the range of >420 nm to 480 nm, a sky blue emitter has an emission maximum in the range of >480 nm to 500 nm, a green emitter has an emission maximum in the range of >500 nm to 560 nm, and a red emitter has an emission maximum in the range of >620 nm to 800 nm.

[0198] The dark blue emitter may preferably have an emission maximum below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.

[0199] Thus, yet another aspect of the present invention relates to an OLED that exhibits an external quantum efficiency greater than 8% (more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even greater than 20%) at 1000 cd / m 2 and / or exhibits an emission maximum between 420 nm and 500 nm (preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm), and / or exhibits an LT80 value greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even greater than 1000 hours) at 500 cd / m 2 Thus, yet another aspect of the present invention relates to an OLED whose emission exhibits a CIEy color coordinate less than 0.45 (preferably less than 0.30, more preferably less than 0.20, or even more preferably less than 0.15, or even less than 0.10).

[0200] Yet another aspect of the present invention relates to an OLED that emits light at different color points. According to the present invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). On the one hand, the OLED according to the invention emits light having an 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, or even less than 0.17 eV).

[0201] Another aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates (CIEx = 0.131, CIEy = 0.046), which are close to the CIEx (= 0.131) and CIEy (= 0.046) color coordinates of the primary blue color as defined by ITU-R Recommendation BT.2020 (Rec.2020), and is thus suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). Accordingly, another aspect of the present invention relates to an OLED whose emission exhibits a CIEx color coordinate between 0.02 and 0.30 (preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20, or even more preferably between 0.08 and 0.18, or even between 0.10 and 0.15) and / or a CIEy color coordinate between 0.00 and 0.45 (preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20, or even more preferably between 0.03 and 0.15, or even between 0.04 and 0.10).

[0202] In yet another aspect, the invention relates to a method for manufacturing an optoelectronic component. In this case, the organic molecules of the invention are used.

[0203] The optoelectronic device (specifically, OLED) according to the present invention can be manufactured by any means of vapor deposition and / or liquid processing. Accordingly, at least one layer:

[0204] - is prepared by means of a sublimation process,

[0205] - is prepared by means of an organic vapor deposition process,

[0206] - is prepared by means of a carrier gas sublimation process,

[0207] - solution processing or printing.

[0208] The method for manufacturing an optoelectronic device (specifically, OLED) according to the present invention is known in the art. By means of subsequent deposition processes, different layers are deposited separately and continuously on a suitable substrate. The same or different deposition methods can be used to deposit each layer.

[0209] Vapor deposition processes include, for example, thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as a substrate. The individual layers may be processed from a solution or dispersion using an appropriate solvent. Solution deposition processes include, for example, spin coating, dip coating, and jet printing. Liquid processing may optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent may be completely or partially removed by means known in the art.

[0210] Example

[0211] General synthetic scheme

[0212]

[0213]

[0214] General Synthesis Scheme I

[0215] General Synthetic Scheme I provides a synthetic scheme for organic molecules according to the invention, wherein R I =R III , R II =R IV , and where n = 0 or 1:

[0216]

[0217]

[0218] General Synthesis Scheme II (Alternative Synthesis of Compound I2)

[0219] General Synthetic Scheme II provides a synthetic scheme for organic molecules according to the invention, wherein R I =R III , R II =R IV , and wherein n=0 or 1;

[0220]

[0221] General steps for synthesizing AAV1:

[0222]

[0223] E1 (1.00 equiv.), E2 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalent, CAS: 13716-12-6) and sodium tert-butoxide NaO tBu (3.50 equiv., CAS: 865-48-5). After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine and the phases were separated. The combined organic layers were dried over MgSO4 and the solvent was then removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to obtain I1 as a solid.

[0224] General steps for synthesizing AAV2:

[0225]

[0226] I1 (1.00 equiv.), E3 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv.; CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalent, CAS: 13716-12-6) and sodium tert-butoxide NaO t Bu (3.00 equiv., CAS: 865-48-5). After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine and the phases were separated. The combined organic layers were dried over MgSO4 and the solvent was then removed under reduced pressure. The obtained crude product was purified by recrystallization or column chromatography to obtain I2 as a solid.

[0227] General steps for synthesizing AAV3:

[0228]

[0229] I2 (1.00 equiv.) was stirred in tert-butylbenzene at 0 °C under nitrogen atmosphere. tert-Butyllithium ( t In the mixture of 4-nitropropene (4-nitropropene) and 4-nitropropene (2-nitropropene) was added 4-nitropropene (2-nitropropene) and the reaction was heated to 50 ° C. The lithiation was quenched by slowly adding trimethyl borate (6.00 equivalents, CAS 121-43-7) at room temperature. After the reaction mixture was heated to 60 ° C for 2 hours, the reaction mixture was cooled to room temperature. Water was added and the mixture was stirred for another 2 hours. After extraction with ethyl acetate, the organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The crude product obtained by recrystallization or column chromatography was purified to obtain I3 as a solid.

[0230] General steps for synthesizing AAV4:

[0231]

[0232] I3 (1.00 equivalent) was stirred in chlorobenzene under a nitrogen atmosphere. N, N-diisopropylethylamine (10.0 equivalent, CAS7087-68-5) and aluminum chloride (AlCl3, 10.0 equivalent, CAS 7446-70-0) were added and the reaction mixture was heated to 120 ° C. After 60 minutes, N, N-diisopropylethylamine (5.00 equivalent, CAS 7087-68-5) and aluminum chloride (AlCl3, 5.00 equivalent, CAS 7446-70-0) were added and the reaction mixture was stirred for 1.5 hours. After cooling to room temperature, the reaction mixture was extracted between DCM and water. The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The residue was purified by recrystallization or column chromatography to obtain P1 as a solid.

[0233] General steps for synthesizing AAV5:

[0234]

[0235] E3 (1.00 equiv.), E2 (1.10 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv.; CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalent, CAS: 13716-12-6) and sodium tert-butoxide NaO t Bu (2.00 equiv., CAS: 865-48-5). After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine and the phases are separated. The combined organic layers are dried over MgSO4 and the solvent is then removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography to obtain I1.2 as a high viscosity oil or solid.

[0236] General steps for synthesizing AAV6:

[0237]

[0238] E1 (1.00 equiv.), I1.2 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv.; CAS: 51364-51-3), tri-tert-butylphosphine P( t Bu)3 (0.04 equivalent, CAS: 13716-12-6) and sodium tert-butoxide NaO t Bu (3.50 equiv., CAS: 865-48-5). After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine and the phases were separated. The combined organic layers were dried over MgSO4 and the solvent was then removed under reduced pressure. The obtained crude product was purified by recrystallization or column chromatography to obtain I2 as a solid.

[0239] Cyclic voltammetry

[0240] The cyclic voltammogram was measured on a solution with a concentration of 10 -3 mol / L of the organic molecule in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). The measurement was carried out using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) under a nitrogen atmosphere at room temperature, and FeCp2 / FeCp2 + was used as an internal standard for calibration. Ferrocene was used as an internal standard to correct the HOMO data for the saturated calomel electrode (SCE).

[0241] Density functional theory calculations

[0242] The molecular structure was optimized using the BP86 functional and the resolution of identity approach (RI). The excitation energies were calculated using the time-dependent DFT (TD-DFT) method with the (BP86)-optimized structure. The orbital and excited-state energies were calculated using the B3LYP functional. The Def2-SVP basis set and the numerical integration method with an m4 grid were used. The Turbomole program package was used for all calculations.

[0243] Photophysical measurements

[0244] Sample pretreatment: Spin coating

[0245] Instrument: Spin150, SPS euro.

[0246] The sample concentration was 10 mg / mL, dissolved in a suitable solvent.

[0247] Procedure: 1) 3 seconds at 400 U / min; 20 seconds at 1000 U / min at 1000 Upm / s. 3) 10 seconds at 4000 U / min at 1000 Upm / s. After coating, the film was dried at 70 °C for 1 min.

[0248] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC)

[0249] The steady-state emission spectra were measured by Horiba Scientific Modell FluoroMax-4 equipped with a 150 W xenon arc lamp, excitation and emission monochromators, and a Hamamatsu R928 photomultiplier tube and a time-correlated single photon counting option. The emission and excitation spectra were corrected using standard calibration fitting.

[0250] The excited state lifetime was determined using the same system with the TCSPC method, an FM-2013 device, and a Horiba Yvon TCSPC hub.

[0251] Excitation sources:

[0252] Nano-LED 370 (wavelength: 371 nm, pulse duration: 1.1 ns)

[0253] Nano-LED 290 (wavelength: 294 nm, pulse duration: <1 ns)

[0254] Spectral LED 310 (wavelength: 314 nm)

[0255] Spectral LED 355 (wavelength: 355 nm).

[0256] Data analysis (exponential fitting) was completed using the software suite Data Station and DAS6 analysis software. The fitting was specified using the chi-square test.

[0257] Photoluminescence quantum yield measurement

[0258] For the measurement of the photoluminescence quantum yield (PLQY), an absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. The quantum yield and CIE coordinates were determined using software version U6039-05 3.6.0.

[0259] The emission maximum is given in nm, the quantum yield Φ is given in %, and the CIE coordinates are given as the x value and y value.

[0260] The following protocol was used to determine the PLQY:

[0261] 1) Quality assurance: Anthracene (known concentration) in ethanol was used as a reference

[0262] 2) Excitation wavelength: The absorption maximum of the organic molecule was determined and the molecule was excited using this wavelength

[0263] 3) Measurement

[0264] For the sample, the quantum yield of the solution or film was measured under a nitrogen atmosphere. The yield was calculated using the equation:

[0265]

[0266] where n 光子 represents the photon count and Int. represents the intensity.

[0267] Fabrication and characterization of optoelectronic devices

[0268] Optoelectronic devices (specifically, OLED devices) comprising the organic molecules according to the invention can be manufactured via vacuum deposition. If a layer contains more than one compound, the weight percentage of one or more compounds is given in %. The total weight percentage value is 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0269] Unoptimized OLEDs are characterized using standard methods and measuring the electroluminescence spectrum, the intensity-dependent external quantum efficiency (in %), which is calculated using the light and current detected by a photodiode. The OLED device lifetime is extracted from the change in luminance during operation at a constant current density. The LT50 value corresponds to the time at which the measured luminance decreases to 50% of the initial luminance, similarly, LT80 corresponds to the time point at which the measured luminance decreases to 80% of the initial luminance, LT95 corresponds to the time point at which the measured luminance decreases to 95% of the initial luminance, etc.

[0270] (e.g., applying an increased current density) for accelerated lifetime measurements. For example, the LT80 value at 500 cd / m 2 is determined using the following equation:

[0271]

[0272] where L0 represents the initial luminance at the applied current density.

[0273] This value corresponds to the average of several (typically 2 to 8) pixels, giving the standard deviation between these pixels.

[0274] HPLC-MS

[0275] HPLC-MS analysis is performed on an Agilent (1100 series) HPLC with an MS detector (Thermo LTQ XL).

[0276] Exemplarily, a typical HPLC method is as follows: an Agilent reversed-phase column 4.6 mm × 150 mm, particle size 3.5 μm (ZORBAX Eclipse Plus C18, 4.6 × 150 mm, 3.5 μm HPLC column) is used in the HPLC. HPLC-MS measurements are performed at room temperature (rt) according to a gradient.

[0277]

[0278] The following solvent mixture is used:

[0279] Solvent A: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent B: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent C: THF (50%) MeCN (50%)

[0280] A 5 μL injection volume was sampled from a solution with an analyte concentration of 0.5 mg / mL for measurement.

[0281] Ionization of the probe was carried out using an atmospheric pressure chemical ionization (APCI) source in positive (APCI+) or negative (APCI−) ionization mode.

[0282] Example 1

[0283]

[0284] Example 1 was synthesized according to the following procedure:

[0285] AAV1 (91% yield), wherein 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) was used as reactant E1 and 1,2,3,5,6,7-hexahydro-S-5-inden-4-yl-amine (CAS: 63089-56-5) was used as reactant E2;

[0286] AAV2 (63% yield), wherein 1-bromo-4-tert-butylbenzene (CAS: 3972-65-4) was used as reactant E3;

[0287] AAV3 and AAV4 (two steps, 18% yield).

[0288] MS (HPLC-MS), m / z (retention time): 693.6 (8.23 min).

[0289] (2 wt% in PMMA) The emission maximum of Example 1 was at 458 nm, the full width at half maximum (FWHM) was 0.15 eV, and the CIEx and CIEy coordinates were 0.14 and 0.08, respectively.

[0290] Additional examples of the inventive organic molecules

[0291] (Note: In the structures drawn, t Bu represents a bonded tert-butyl group such that is equivalent to

[0292] Furthermore, Ph represents a bonded phenyl group such that is equivalent to

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

Claims

1. An organic molecule, the organic molecule comprising a structure of formula I: Wherein, R I 、R II 、R III 、R IV 、R V and R VI are independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl and carbazolyl; R VII selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph and carbazolyl; 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; halogen; C1-C 12 alkyl; and C6-C 18 aryl; wherein at least R A together with R B and R C together with R D form a monocyclic ring system having 5 to 8 C atoms; And optionally, each hydrogen is independently replaced by deuterium or a halogen.

2. The organic molecule according to claim 1, wherein, The organic molecule comprises a structure of formula Ia:

3. The organic molecule according to claim 1 or 2, wherein The organic molecule comprises a structure of formula Ia-2:

4. The organic molecule according to claim 1, wherein, The organic molecule comprises a structure of formula Ib:

5. The organic molecule according to claim 1 or 4, wherein The organic molecule comprises a structure of formula Ib-2:

6. The organic molecule according to claim 1, wherein, The organic molecule is selected from the following compounds:

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

8. The application according to claim 7, wherein The optoelectronic device is selected from the group consisting of: Organic light-emitting diodes; Light-emitting electrochemical cells; Organic light-emitting diode sensors; Organic diodes; Organic solar cells; Organic transistors; Organic field-effect transistors; Organic lasers; and Down-conversion elements.

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

10. An optoelectronic device, the optoelectronic device comprising an organic molecule according to any one of claims 1 to 6 or a composition according to claim 9, the optoelectronic device being in the form of a device selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

11. The optoelectronic device according to claim 10, the optoelectronic device comprising: A substrate; An anode; And A cathode, wherein the anode or the cathode is disposed on the substrate; And A light-emitting layer disposed between the anode and the cathode and comprising the organic molecule or the composition.

12. A method for manufacturing an optoelectronic device, wherein, Use an organic molecule according to any one of claims 1 to 6 or a composition according to claim 9.

13. The method according to claim 12, the method comprising the step of treating the organic molecule by vacuum evaporation or from a solution.

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