Organic molecules for optoelectronic devices

Abstract

The invention relates to organic molecules for use in optoelectronic devices. According to the invention, the organic molecules have a structure of formula I: wherein T and V are independently of each other selected from the group consisting of R 1 and R 2 ; R 1 comprises or consists of a structure of formula II at each occurrence: formula II is bound via the position marked by a dashed line; and Ar 1 is a C6-C 60 aryl group which is optionally substituted with one or more substituents R 6 .

Description

Technical Field

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

[0002] We are actively developing applications of organic molecules in optoelectronic devices. Summary of the Invention

[0003] The purpose of this invention is to provide organic molecules suitable for use in optoelectronic devices.

[0004] This objective is achieved through the invention of a novel organic molecule.

[0005] According to the invention, the organic molecule is a pure organic molecule, that is, it does not contain any metal ions, unlike known metal complexes used in optoelectronic devices. However, the organic molecule of the invention includes quasi-metals (specifically, B, Si, Sn, Se and / or Ge).

[0006] According to the present invention, the organic molecules exhibit emission maxima in the blue, sky-blue, or green spectral ranges. Specifically, the organic molecules exhibit emission maxima 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 molecules according to the invention is 50% or greater. The use of the organic molecules according to the invention in optoelectronic devices (e.g., organic light-emitting diodes (OLEDs)) results in higher efficiency or higher color purity (expressed by the full width at half maximum (FWHM) of the emission). The corresponding OLEDs exhibit higher stability than OLEDs with known emitter materials and comparable colors.

[0007] The organic molecules according to the invention include or are composed of the structure of Formula I.

[0008]

[0009]

[0010] in,

[0011] T and V are independently selected from R 1 and R 2 The group formed;

[0012] R 1 Each occurrence includes the structure of Formula II or consists of the structure of Formula II:

[0013]

[0014] Formula II is combined via the dashed line: ---- the position marked;

[0015] Ar 1 It can optionally replace one or more substituents R 6 C6-C 60 Aryl;

[0016] R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh (Ph = phenyl); SPh; CF3; CN; F; Si(C1-C5 alkyl)3; Si(Ph)3; C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently substituted with deuterium (D), CN, CF3 or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C6-C 18 Aryl group, wherein one or more hydrogen atoms are optionally substituted independently of each other by C1-C5 alkyl, Ph, CN, CF3 or F; C3-C 17 Heteroaryl, wherein one or more hydrogen atoms are optionally independently substituted by C1-C5 alkyl, Ph, CN, CF3 or F; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);

[0017] R 6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; SPh; CF3; CN; F; Si(C1-C5 alkyl)3; Si(Ph)3; C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C6-C18 Aryl group, optionally substituted with one or more C1-C5 alkyl substituents; C3-C 17 Heteroaryl groups, optionally substituted with one or more C1-C5 alkyl substituents; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);

[0018] Among them, exactly a portion of the groups consisting of T and V is R. 1 And exactly a portion of the groups consisting of T and V are R. 2 .

[0019] In one embodiment of the invented organic molecule, Ar 1 Selected from the group consisting of: Ph, optionally substituted with one or more substituents, said substituents being independently selected from D, Me, i Pr、 t Bu, CN, CF3, SiMe3, Si i The group consisting of Pr3, NPh2, carbazole, and Ph; naphthyl, optionally substituted with one or more substituents, said substituents being independently selected from the group consisting of D, Me, i Pr、 t Bu, CN, CF3, SiMe3, Si i The group consisting of Pr3, NPh2, carbazole, and Ph; and anthracene, optionally substituted with one or more substituents, said substituents being independently selected from the group consisting of D, Me, i Pr、 t Bu, CN, CF3, SiMe3, Si i The group consists of Pr3, NPh2, carbazole group and Ph.

[0020] In some embodiments, Ar 1 Each occurrence is independently selected from the group consisting of:

[0021]

[0022]

[0023] Each of Equations IIa to IIp is represented by a wavy line. The position of the marker is incorporated into B of Formula II.

[0024] In one embodiment, R 1 Each occurrence consists of the structure of formula II-I:

[0025]

[0026] in,

[0027] m is 0 or 1;

[0028] n is 0 or 1;

[0029] o is 0 or 1;

[0030] If n = 0, then o = 0;

[0031] If m = 1, then G a It is C; if m = 0, then G a It is CR c ;

[0032] If m = 1, then J a It is C; if m = 0, then J a It is CR c ;

[0033] If n = 1, then G b It is C; if n = 0, then G. b It is CR c ;

[0034] If n = 1, then there is exactly one J. b It is C and another J b It is CR c ;

[0035] If n = 0, then J b Each occurrence is an independent CR. c ;

[0036] If o = 1, then G c It is C; if o = 0, then G c It is CR c ;

[0037] If o = 1, then J c It is C; if o = 0, then J c It is CR c ;

[0038] R c Each time it appears, it is independently selected from hydrogen, deuterium, Me, i Pr、 t Bu, CN, CF3, SiMe3, Si i The group consists of Pr3, NPh2, carbazole group and Ph.

[0039] In one embodiment, R 1 Each occurrence is composed of the structure of Equation II-II:

[0040]

[0041] In some embodiments, R 1 Each occurrence is selected from the group consisting of the following:

[0042]

[0043]

[0044]

[0045] In one embodiment, R 2 Each time it appears, it is independently selected from the group consisting of: OPh (Ph = phenyl); SPh; CF3; CN; F; Si(C1-C5 alkyl)3; Si(Ph)3; C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently substituted with deuterium (D), CN, CF3 or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently substituted with deuterium, CN, CF3 or F; C6-C 18 The aryl group may optionally be substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms may be independently substituted with Ph, CN, CF3, or F; C3-C 17 Heteroaryl, optionally substituted with one or more C1-C5 alkyl substituents, and with one or more hydrogen atoms independently substituted by Ph, CN, CF3, or F; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 Aryl).

[0046] In one embodiment, R 2 Selected from the group consisting of: C6-C 18 The aryl group may optionally be substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms may be independently substituted with CN, CF3, or F; and the C3-C 17 The heteroaryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted by CN, CF3 or F.

[0047] In one embodiment, R 2 Selected from the group consisting of: C6-C 18 The aryl group may optionally be substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms may be independently substituted with CN or CF3; and C3-C 17 The heteroaryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted by CN or CF3.

[0048] In one embodiment, R 2 Selected from the group consisting of: Me; i Pr; t Bu; SiMe3; SiPh3; and Ph, optionally substituted with one or more substituents, said substituents being independently selected from Me, i Pr、 t The group consists of Bu and Ph.

[0049] In a preferred embodiment, R 2 Each occurrence is independent of the others: C6-C 18 The aryl group may optionally be substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms may be independently substituted with CN, CF3, or F.

[0050] In a preferred embodiment, R 2 Selected from the group consisting of: i Pr; and Ph, optionally substituted with one or more Ph substituents.

[0051] In a more preferred embodiment, R 2 Yes: C6-C 18 The aryl group may optionally be substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms may be independently substituted with CN, CF3, or F.

[0052] In a more preferred embodiment, R 2 Yes: C6-C 18 The aryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted by F or CF3.

[0053] In another embodiment, R 2 Yes: C6-C 18 The aryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted by CN or CF3.

[0054] In one embodiment, R 2 Yes: C6-C 18 The aryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted by CN.

[0055] In one embodiment, R 2 Yes: C6-C 18 The aryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted with CF3.

[0056] In one embodiment, R 2 Yes: C6-C 18 The aryl group is optionally substituted with one or more C1-C5 alkyl substituents, and one or more hydrogen atoms are independently substituted with F.

[0057] In one embodiment, the organic molecule comprises or is composed of a structure of formula IIIa:

[0058]

[0059] Any of the above definitions applies.

[0060] In one embodiment, the organic molecule comprises or is composed of a structure of formula IIIb:

[0061]

[0062] Any of the above definitions applies.

[0063] In one embodiment, the organic molecule comprises, or is composed of, structures selected from the group consisting of:

[0064]

[0065]

[0066]

[0067] In a preferred embodiment, the organic molecule comprises a structure selected from the group consisting of formulas IIIa-1, IIIb-1, IIIa-2, IIIb-2, IIIa-3, and IIIb-3, or is composed of a structure selected from the group consisting of formulas IIIa-1, IIIb-1, IIIa-2, IIIb-2, IIIa-3, and IIIb-3.

[0068] Among them, R1 Selected from the group consisting of:

[0069]

[0070]

[0071] In one embodiment, the organic molecule comprises a structure selected from the group consisting of formulas IIIa-1, IIIa-2, and IIIa-3, or is composed of a structure selected from the group consisting of formulas IIIa-1, IIIa-2, and IIIa-3, wherein R 1 Selected from the group consisting of:

[0072]

[0073] In one embodiment, the organic molecule comprises a structure selected from the group consisting of formulas IIIb-1, IIIb-2, and IIIb-3, or is composed of a structure selected from the group consisting of formulas IIIb-1, IIIb-2, and IIIb-3, wherein R 1 Selected from the group consisting of:

[0074] Detailed Implementation

[0075] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group comprises 6 to 60 aromatic ring atoms, and a heteroaryl group comprises 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 definitions of certain substituents. Specifically, a heteroaromatic ring comprises one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety comprising at least one heteroatom. Heteratoms may be the same or different each time they appear and may be individually selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent having two binding sites with other molecular structures and thus serving as a linking group structure. Where the group in the exemplary embodiments is defined differently from the definitions given herein (e.g., the number of aromatic ring atoms or the number of heteroatoms differs from the given definitions), the definitions in the exemplary embodiments will apply. According to the invention, the condensed (cyclized) aromatic polycyclic or heteroaromatic polycyclic is composed of two or more monoaromatic or heteroaromatic rings that form a polycyclic structure via a condensation reaction.

[0076] Specifically, as used throughout this document, the term "aryl or heteroaryl" includes groups that can be attached at any position via an aromatic or heteroaryl group derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, etc. Perylene, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenothiazine, pyrazole, indazole, imidazole, benzimidazole, naphthiamidazole, phenanthrenemidazole, pyridinium pyridimazole, pyrazinium pyridimazole, quinoxalineium pyridimazole, oxazole, benzo[a] Oxazole, naphthooxazole, anthraxazole, phenanthreneoxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthidine, carboline, benzocarboline, phenanthrene, 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-tetraazine, purine, pteridine, indene, and benzothiadiazole, or combinations of the above groups.

[0077] As used throughout this document, the term "cyclic group" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic moiety.

[0078] As used throughout this document, the term "biphenyl" as a substituent can be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined in relation to the binding site with another chemical moiety.

[0079] As used throughout this document, the term "terphenyl" as a substituent can be understood in the broadest sense as 3-o-terphenyl, 4-o-terphenyl, 4-m-terphenyl, 5-m-terphenyl, 2-p-terphenyl, or 3-p-terphenyl, where ortho, m, and p are defined with respect to the relative positions of the Ph moieties, and "2-", "3-", "4-", and "5-" are defined with respect to the binding site with another chemical moiety, i.e.:

[0080]

[0081] Here, # represents the binding site with another chemical moiety.

[0082] As used throughout this document, the term "naphthyl" as a naphthalene substituent can be understood in the broadest sense as 1-naphthyl and 2-naphthyl, where "1-" and "2-" are defined in relation to the binding site with another chemical moiety, namely:

[0083]

[0084] Here, # represents the binding site with another chemical moiety.

[0085] As used throughout this document, the term "anthrayl" as a substituent can be understood in the broadest sense as 1-anthrayl, 2-anthrayl, and 9-anthrayl, where "1-", "2-", and "9-" are defined in relation to the binding site with another chemical moiety, i.e.:

[0086]

[0087] Here, # represents the binding site with another chemical moiety.

[0088] As used throughout this document, the term "alkyl" can be understood in the broadest sense as any straight-chain, branched, or cyclic alkyl substituent. Specifically, the term alkyl includes substituents such as methyl (Me), ethyl (Et), and 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, secondary pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, secondary 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-hexyl-1-yl, 1,1-dimethyl-n-heptyl-1-yl, 1,1-dimethyl-n-octyl-1-yl, 1,1-dimethyl-n-decyl-1-yl, 1,1-dimethyl-n-dodecane-1-yl, 1,1-dimethyl-n-tetradecane-1-yl, 1,1-dimethyl-n-hexadecane-1-yl, 1,1-dimethyl-n-octadecane-1-yl, 1,1-diethyl-n-hexyl-1-yl, 1,1-diethyl-n-heptyl-1-yl, 1,1-diethyl-n-octyl-1-yl, 1,1-diethyl-n-decane-1-yl, 1,1-diethyl-n- Dodecane-1-yl, 1,1-diethyl-n-tetradecane-1-yl, 1,1-diethyl-n-hexadecane-1-yl, 1,1-diethyl-n-octadecane-1-yl, 1-(n-propyl)-cyclohexyl-1-yl, 1-(n-butyl)-cyclohexyl-1-yl, 1-(n-hexyl)-cyclohexyl-1-yl, 1-(n-octyl)-cyclohexyl-1-yl and 1-(n-decyl)-cyclohexyl-1-yl.

[0089] As used throughout, the term "alkenyl" includes straight-chain, branched, 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.

[0090] As used throughout, the term "alkynyl" includes straight-chain, branched, and cyclic alkynyl substituents. Examples of alkynyl substituents include ethynyl, propynyl, butynyl, pentyynyl, hexynyl, heptyynyl, or octyynyl.

[0091] As used throughout, the term "alkoxy" includes straight-chain, branched, and cyclic alkoxy substituents. Exemplary examples of the term "alkoxy" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and 2-methylbutoxy.

[0092] As used throughout, the term "thioalkoxy" includes straight-chain, branched, and cyclic thioalkoxy substituents in which the O of an alkoxy group is replaced by an S group, as exemplarily described.

[0093] As used throughout, the terms “halogen” and “halogenated” can be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0094] Whenever hydrogen (H) is mentioned here, it can also be replaced by deuterium each time it appears.

[0095] It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another part, its name may be written as if it were a fragment (e.g., naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached fragments are considered equivalent.

[0096] In one embodiment of the invention, the organic molecule according to the invention has an emission peak in the visible or closest to ultraviolet range (i.e., in the wavelength range of 380 nm to 800 nm) and a full width at half maximum (FWHM) of less than 0.35 eV (preferably less than 0.30 eV, more preferably less than 0.26 eV, even more preferably less than 0.22 eV or even less than 0.18 eV) at room temperature in dichloromethane (DCM) containing 0.001 mg / mL of organic molecule or in a poly(methyl methacrylate) (PMMA) film containing 1% by weight of organic molecule at room temperature.

[0097] The energy of the first excited triplet state (T1) is determined by the starting point of the emission spectrum at low temperature (typically 77 K). Phosphorescence is generally visible in the steady-state spectrum in films with 2% emitter and 98% PMMA. Therefore, the triplet energy can be determined as the starting point of the phosphorescence spectrum. For fluorescent emitter molecules, the energy of the first excited triplet state (T1) is determined by the starting point of the delayed emission spectrum at 77 K.

[0098] The starting point of the emission spectrum is determined by calculating the intersection of the 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 point of half maximum intensity of the emission spectrum.

[0099] In one embodiment, the organic molecules according to the invention have an emission spectrum at room temperature in a DCM containing 0.001 mg / mL of organic molecules or in a poly(methyl methacrylate) (PMMA) film containing 1% by weight of organic molecules, with an energy starting point close to the emission maximum, 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 molecules is less than 0.35 eV (preferably less than 0.30 eV, more preferably less than 0.26 eV, even more preferably less than 0.22 eV, or even less than 0.18 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).

[0100] Another aspect of the invention relates to the application of the organic molecules of the invention in optoelectronic devices as light emitters or absorbers and / or as host materials and / or as electron transport materials and / or as hole injection materials and / or as hole blocking materials.

[0101] Preferred embodiments relate to the application of the organic molecules according to the invention as light emitters in optoelectronic devices.

[0102] Optoelectronic devices can be understood in the broadest sense as any device based on organic materials suitable for emitting visible light or light in the range closest to the ultraviolet (UV) (i.e., wavelengths from 380 nm to 800 nm). More preferably, optoelectronic devices can be capable of emitting light in the visible light range (i.e., wavelengths from 400 nm to 800 nm).

[0103] In this context, optoelectronic devices are more specifically selected from the group consisting of:

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

[0105] • Photoluminescent electrochemical cells;

[0106] • OLED sensors, especially gas and vapor sensors that are not sealed and isolated from the surrounding environment;

[0107] Organic diodes;

[0108] Organic solar cells;

[0109] Organic transistors;

[0110] • Organic field-effect transistors;

[0111] Organic lasers; and

[0112] Down-conversion element.

[0113] In a preferred embodiment within the context of this application, the optoelectronic device is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0114] In this application, the fraction of the organic molecules according to the invention in the emitting layer of the optoelectronic device (more specifically, in an OLED) is from 0.1 wt% to 99 wt% (more specifically, from 1 wt% to 80 wt%). In an alternative embodiment, the proportion of organic molecules in the emitting layer is 100 wt%.

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

[0116] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0117] (a) at least one organic molecule according to the invention, specifically in the form of an emitter; and

[0118] (b) One or more triplet-triplet annihilation (TTA) host materials that are different from the organic molecule according to the invention; and

[0119] (c) Optionally, one or more TADF materials;

[0120] (d) Optionally, one or more dyes and / or one or more solvents.

[0121] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0122] (a) at least one organic molecule according to the invention, specifically in the form of an emitter; and

[0123] (b) One or more host materials that are different from the organic molecule according to the invention; and

[0124] (c) One or more TADF materials.

[0125] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0126] (a) at least one organic molecule according to the invention, specifically in the form of an emitter; and

[0127] (b) One or more host materials that are different from the organic molecule according to the invention; and

[0128] (c) One or more phosphorescent materials.

[0129] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0130] (a) at least one organic molecule according to the invention, specifically in the form of an emitter; and

[0131] (b) One or more host materials that are different from the organic molecule according to the invention; and

[0132] (c) one or more TADF materials; and

[0133] (d) One or more phosphorescent materials.

[0134] In a specific embodiment, the light-emitting layer (EML) comprises (or is substantially composed of) a composition comprising or consisting of the following components:

[0135] (i) 0.1% to 10% by weight (preferably, 0.5% to 5% by weight, specifically 1% to 3% by weight) of one or more organic molecules (E) according to the invention;

[0136] (ii) at least one host compound (H) comprising 5% to 99% by weight (preferably 15% to 85% by weight, specifically 20% to 75% by weight); and

[0137] (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 main compound (D), the other main compound (D) having a structure different from that of the organic molecule according to the invention; and

[0138] (iv) Optionally, a solvent of 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight); and

[0139] (v) Optionally, 0% to 30% by weight (specifically, 0% to 20% by weight, preferably 0% to 5% by weight) of at least one other emitter molecule (F), which has a structure different from that of the organic molecule according to the invention.

[0140] Compositions having one or more TTA host materials

[0141] In a preferred embodiment, in the organic electroluminescent device of the present invention, the light-emitting layer (EML) comprises (or is composed of) the following components:

[0142] (i) 10% to 84% by weight of TTA material (H N );

[0143] (ii) 0% to 30% by weight of TADF material (E B );and

[0144] (iii) 0.1% to 10% by weight of the organic molecule (emitter) according to the invention; and optionally

[0145] (iv) 0% to 89.9% by weight of one or more solvents.

[0146] In a preferred embodiment, the sum of the percentages of (i) to (iv) reaches 100% by weight.

[0147] In another preferred embodiment, in the organic electroluminescent device of the present invention, the light-emitting layer (EML) comprises (or is composed of) the following components:

[0148] (i) 56% to 90% by weight of TTA material (H N );

[0149] (ii) 0% to 5% by weight of TADF material (E B );and

[0150] (iii) 0.5% to 5% by weight of the organic molecule (emitter) according to the invention; and optionally...

[0151] (iv) 0% to 43.5% by weight of one or more solvents.

[0152] In a preferred embodiment, the sum of the percentages of (i) to (iv) reaches 100% by weight.

[0153] Compositions having one or more TADF materials

[0154] In one embodiment, the light-emitting layer (EML) comprises the following components:

[0155] (i) 10% to 89.9% by weight of one or more p-host compounds (H P );

[0156] (ii) 0% to 79.9% by weight of one or more n host compounds (H N );

[0157] (iii) 10% to 50% by weight of one or more TADF materials (E B );and

[0158] (iv) 0.1% to 10% by weight of one or more organic molecules (emitters) according to the invention; and

[0159] (v) 0% to 72% by weight of one or more solvents.

[0160] In one embodiment, the light-emitting layer (EML) comprises the following components:

[0161] (i) 22% to 87.5% by weight of one or more p-host compounds (H P );

[0162] (ii) Optionally, from 0% to 65.5% by weight of one or more n host compounds (H N );

[0163] (iii) 12% to 40% by weight of one or more TADF materials (E B );and

[0164] (iv) 0.5% to 5% by weight of one or more organic molecules (emitters) according to the invention; and

[0165] (v) 0% to 65.5% by weight of one or more solvents.

[0166] Composition having one or more phosphorescent materials

[0167] In which H N In an optional preferred embodiment, in the organic electroluminescent device of the present invention, the light-emitting layer (EML) comprises (or is composed of) the following components:

[0168] (i) 10% to 84.9% by weight of the main compound (H P );

[0169] (ii) 0% to 84.9% by weight of the main compound (H N );

[0170] (iii) 5% to 15% by weight of phosphorescent material (E B );and

[0171] (iv) 0.1% to 10% by weight of the organic molecule (emitter) according to the invention; and optionally

[0172] (v) 0% to 72% by weight of one or more solvents.

[0173] In which H N In an optional preferred embodiment, in the organic electroluminescent device of the present invention, the light-emitting layer (EML) comprises (or is composed of) the following components:

[0174] (i) 22% to 70.5% by weight of the main compound (H P );

[0175] (ii) 0% to 70.5% by weight of the main compound (H N );

[0176] (iii) 5% to 10% by weight of phosphorescent material (E B );and

[0177] (iv) 0.5% to 5% by weight of the organic molecule (emitter) according to the invention; and optionally...

[0178] (v) 0% to 72% by weight of one or more solvents.

[0179] 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.

[0180] In one embodiment, the host compound (H) has an energy (E) in the range of -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital (HOMO(H)) of (H) and at least one other host compound (D) possesses the energy (E) HOMO The highest occupied molecular orbital (HOMO(D)) of E(D)) is where E(D) is located. HOMO (H)>E HOMO (D)

[0181] In yet another embodiment, the host compound (H) possesses energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H), and at least one other host compound (D) possessing the energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(D)) of E(D), where E LUMO (H)>E LUMO (D)

[0182] In one embodiment, the host compound (H) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(H)) and the energy (E) of (H) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H) and

[0183] At least one other main compound (D) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(D)) and the energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(D)) of (D)

[0184] According to the invention, the organic molecule (E) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(E)) and the energy possessed by (E) LUMO The lowest unoccupied molecular orbital (LUMO(E)) of (E),

[0185] in,

[0186] E HOMO (H)>E HOMO (D), and according to the energy level (E) of the highest occupied molecular orbital (HOMO(E)) of the invented organic molecule (E). HOMO The energy levels of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) and (E) are related to the energy levels of the highest occupied molecular orbital (HOMO(H)) of the host compound (H). HOMO The difference between (H)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0187] E LUMO (H)>E LUMO (D), and according to the invention, the energy level (E) of the lowest unoccupied molecular orbital (LUMO(E)) of the organic molecule (E) LUMO (E)) and the energy level of at least one other host compound D's lowest unoccupied molecular orbital (LUMO(D)) (E) LUMO The difference between (D) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0188] In one embodiment of the invention, the host compound (D) and / or the host compound (H) are thermally activated delayed fluorescence (TADF) materials. TADF materials exhibit fluorescence intensity less than 2500 cm⁻¹. -1The energy difference ΔE between the first excited singlet state (S1) and the first excited triplet state (T1) ST Value. Preferably, TADF material exhibits a value of less than 3000 cm. -1 More preferably less than 1500cm -1 or even more preferably less than 1000cm -1 Or even less than 500cm -1 ΔE ST value.

[0189] In one embodiment, the host compound (D) is a TADF material, and the host compound (H) exhibits a thickness greater than 2500 cm⁻¹. -1 ΔE ST Value. 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.

[0190] In one embodiment, the host compound (H) is a TADF material, and the host compound (D) exhibits a length greater than 2500 cm⁻¹. -1 ΔE ST Value. 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(biphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine).

[0191] In another aspect, the invention relates to an optoelectronic device comprising the organic molecules described herein or compositions of the type described herein, more specifically in the form of devices selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED sensors (specifically, gas and vapor sensors that are not externally isolated by a sealed structure), organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

[0192] In a preferred embodiment, the optoelectronic device is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0193] 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 light-emitting layer (EML).

[0194] In one embodiment of the optoelectronic device of the invention, the light-emitting layer (EML) is composed of the composition according to the invention described herein.

[0195] When the optoelectronic device is an OLED, it can have, for example, the following layer structure:

[0196] 1. Base

[0197] 2. Anode layer, A

[0198] 3. Hole injection layer, HIL

[0199] 4. Hole transport layer, HTL

[0200] 5. Electron blocking layer, EBL

[0201] 6. Emitting layer, EML

[0202] 7. Hole blocking layer, HBL

[0203] 8. Electron Transport Layer (ETL)

[0204] 9. Electron Injection Layer (EIL)

[0205] 10. Cathode layer, C,

[0206] OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL and EIL. Optionally, different layers may be combined. OLED may include more than one layer from each of the layer types defined above.

[0207] In addition, in one embodiment, the optoelectronic device may include one or more protective layers that protect the device from damage caused by exposure to harmful substances in the environment, including, for example, moisture, vapor and / or gases.

[0208] In one embodiment of the invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0209] 1. Base

[0210] 2. Cathode layer, C

[0211] 3. Electron Injection Layer (EIL)

[0212] 4. Electron Transport Layer (ETL)

[0213] 5. Hole blocking layer, HBL

[0214] 6. Emitting layer, EML

[0215] 7. Electron blocking layer, EBL

[0216] 8. Hole Transport Layer (HTL)

[0217] 9. Hole injection layer, HIL

[0218] 10. Anode layer, A,

[0219] OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL and EIL. Optionally, different layers may be combined. OLED may include more than one layer from each of the layer types defined above.

[0220] In one embodiment of the invention, the optoelectronic device is an OLED that may have a stacked architecture. In this architecture, contrary to a 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 using OLEDs exhibiting a stacked architecture; specifically, white light can be generated by stacking blue OLEDs, green OLEDs, and red OLEDs. Furthermore, OLEDs exhibiting a stacked architecture may include a charge generation layer (CGL), which is typically located between two OLED sub-units and typically consists of an n-doped layer and a p-doped layer, with the n-doped layer of a CGL typically located close to the anode layer.

[0221] In one embodiment of the invention, the optoelectronic device is an OLED comprising two or more emitting layers between the anode and cathode. Specifically, this so-called tandem OLED comprises three emitting layers, wherein one emitting layer emits red light, one emitting green light, and one emitting blue light, and optionally, layers such as charge-generating layers, blocking layers, or transport layers may be further included between the respective emitting layers. In another embodiment, the emitting layers are stacked adjacent to each other. In yet another embodiment, the tandem OLED includes a charge-generating layer between every two emitting layers. Additionally, adjacent emitting layers or emitting layers separated by charge-generating layers may be merged.

[0222] The substrate can be formed from any material or combination of materials. Most commonly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., a copper, gold, silver, or aluminum film) or a plastic film or glass slide can be used. This allows for a higher degree of flexibility. The anode layer (A) is primarily composed of materials that allow for a (substantially) transparent film. Since at least one of the two electrodes should be (substantially) transparent to allow light emission from the OLED, the anode layer (A) or cathode layer (C) is transparent. Preferably, the anode layer (A) comprises a large amount of transparent conductive oxide (TCO), or is even composed of transparent conductive oxide (TCO). Such an anode layer (A) can, for example, include indium tin oxide, zinc aluminum 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.

[0223] The anode layer (A) can (basically) be made of indium tin oxide (ITO) (e.g., (InO3)). 0.9 (SnO2) 0.1The anode layer (A) can be composed of a hole injection layer (HIL). The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). Furthermore, the HIL can promote the injection of quasi-charge carriers (i.e., holes) because the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is facilitated. 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) also prevents metal from diffusing from the anode layer (A) into the hole transport layer (HTL). 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'-spirodifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylphenyl-1,4-diamine)), NPB ( N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetra(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,12-hexaazatriphenylhexacarboxynitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirodifluorene-2,7-diamine).

[0224] Adjacent to the anode layer (A) or hole injection layer (HIL), a hole transport layer (HTL) is typically positioned. Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazole can be used as hole transport compounds. The HTL can lower the energy barrier between the anode layer (A) and the light-emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high energy level of its triplet state (T1). For example, a hole transport layer (HTL) may include tris(4-carbazole-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenylamine)), 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, NPN Star-shaped heterocycles of PB, MeO-TPD, HAT-CN, and / or tri-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, the HTL may include a p-doped layer composed of inorganic or organic dopants 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. Tetrafluorotetracyanoquinone dimethyl ether (F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used, for example, as organic dopants.

[0225] EBLs may include, for example, mCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazole-9-yl)biphenyl), tri-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) and / or DCB (N,N'-dicarbazole-1,4-dimethylbenzene).

[0226] Adjacent to the hole transport layer (HTL), a light-emitting layer (EML) is typically positioned. The light-emitting layer (EML) comprises at least one organic molecule. Specifically, the EML comprises at least one organic molecule (E) according to the invention. In one embodiment, the light-emitting layer comprises only the organic molecule according to the invention. Typically, the EML additionally comprises one or more host materials (H). For example, the host material (H) is selected from CBP (4,4'-bis(N-carbazolyl)-biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran)-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene- [2-[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'-spirodifluorene-2-yl)-1,3,5-triazine). The host material (H) should typically be selected to exhibit first triplet (T1) and first singlet (S1) energy levels that are higher in energy than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0227] 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 comprises exactly one luminescent organic molecule according to the invention and the hybrid host system comprising a T2T as the electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole as the hole-dominant host. In another embodiment, the EML comprises 50% to 80% by weight (preferably 60% to 75% by weight) of a body, 10% to 45% by weight (preferably 15% to 30% by weight) of T2T, and 5% to 40% by weight (preferably 10% to 30% by weight) of an organic molecule according to the invention, the body being 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.

[0228] Adjacent to the luminescent layer (EML), an electron transport layer (ETL) may be positioned. Any electron transport agent can be used here. Exemplarily, electron-depleted compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone can be used. The electron transporter can also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). ETLs may include NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), 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 materials such as Liq. Electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0229] HBLs can include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), and TSPO1 (diphenyl-4-triphenylsilyl) Phenylphosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazolyl-9-yl)benzene).

[0230] Adjacent to the electron transport layer (ETL), a cathode layer (C) may be positioned. The cathode layer (C) may, for example, comprise a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or may be composed of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also be composed of a (substantially) opaque metal such as Mg, Ca, or Al. Optionally or additionally, the cathode layer (C) may also comprise graphite and / or carbon nanotubes (CNTs). Optionally, the cathode layer (C) may also be composed of nanoscale silver wires.

[0231] The OLED may optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (lithium 8-hydroxyquinoline), Li2O, BaF2, MgO and / or NaF.

[0232] Optionally, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also include one or more host compounds (H).

[0233] To further modify the emission and / or absorption spectra of the emissive layer (EML), the EML may further include one or more other emitter molecules (F). Such emitter molecules (F) can be any emitter molecule known in the art. Preferably, such emitter molecules (F) are molecules having a structure different from that of the organic molecule (E) according to the invention. The emitter molecule (F) may optionally be a TADF emitter. Alternatively, the emitter molecule (F) may optionally be a fluorescent and / or phosphorescent emitter molecule capable of shifting the emission and / or absorption spectra of the EML. Exemplarily, by emitting light that is typically redshifted compared to light emitted by the organic molecule, triplet and / or singlet excitons can transfer from the organic molecule according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Optionally, the emitter molecule (F) may also induce a two-photon effect (i.e., absorption of half the energy of the maximum absorption value of the two photon pairs).

[0234] Optionally, the optoelectronic device (e.g., OLED) can be a substantially 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. Then, energy transmittance may optionally exist between the two or more molecules as described above.

[0235] As used herein, unless otherwise defined in the specific context, the color of the emitted and / or absorbed light is specified as follows:

[0236] Purple: Wavelength range from >380nm to 420nm;

[0237] Deep blue: wavelength range >420nm to 480nm;

[0238] Sky blue: >480nm to 500nm wavelength range;

[0239] Green: Wavelength range >500nm to 560nm;

[0240] Yellow: Wavelength range >560nm to 580nm;

[0241] Orange: Wavelength range from >580nm to 620nm;

[0242] Red: Wavelength range from 620nm to 800nm.

[0243] For emitter molecules, this color refers to the maximum emission value. Thus, for example, a dark blue emitter has a maximum emission value in the range of >420nm to 480nm, a sky blue emitter has a maximum emission value in the range of >480nm to 500nm, a green emitter has a maximum emission value in the range of >500nm to 560nm, and a red emitter has a maximum emission value in the range of >620nm to 800nm.

[0244] The deep blue emitter may preferably have a maximum emission value 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.

[0245] Therefore, another aspect of the present invention relates to an OLED that has a density of 1000 cd / m². 2 It 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%), and / or exhibits a maximum emission value between 420 nm and 500 nm (preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm), and / or at 500 cd / m². 2 The OLED 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 more preferably greater than 1000 hours). Therefore, another aspect of the invention relates to an OLED whose emission exhibits 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, or even more preferably less than 0.10).

[0246] Another aspect of the invention relates to an OLED that emits light at different color points. According to the invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). Specifically, the OLED according to the invention emits light with an FWHM of a main emission peak of 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).

[0247] Another aspect of the invention relates to an OLED that emits light having CIEx and CIEy color coordinates (CIEx = 0.131, CIEy = 0.046) (the CIEx and CIEy color coordinates (CIEx = 0.131, CIEy = 0.046) close to the CIEx (= 0.131) and CIEy (= 0.046) color coordinates of the primary color blue as defined by ITU-R Recommendation BT.2020 (Rec.2020), and is therefore suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). Therefore, another aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates 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 more preferably between 0.10 and 0.15) and / or CIEy color coordinates 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 more preferably between 0.04 and 0.10).

[0248] In another aspect, the invention relates to a method for manufacturing optoelectronic components. In this case, the organic molecules of the invention are used.

[0249] The optoelectronic device (specifically, OLED) according to the invention can be fabricated by any method of vapor deposition and / or liquid processing. Therefore, at least one layer:

[0250] -Prepared via sublimation process.

[0251] -Prepared using an organic vapor deposition process.

[0252] -Prepared via carrier gas sublimation process.

[0253] - Solution treatment or printing.

[0254] The method for manufacturing optoelectronic devices (specifically, OLEDs) according to the present invention is known in the art. Different layers are deposited individually and continuously on a suitable substrate via subsequent deposition processes. The individual layers can be deposited using the same or different deposition methods.

[0255] Vapor deposition processes include, for example, thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active-matrix OLED displays, an AMOLED backplane serves as the substrate. Individual layers can be processed from solution or dispersion using suitable solvents. Solution deposition processes include, for example, spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent can be completely or partially removed by methods known in the art.

[0256] Example

[0257] General Synthesis Scheme I

[0258] General Synthesis Scheme I provides a synthesis scheme for the organic molecule according to the invention, wherein T = R 2 And V = R 1 :

[0259] General steps for synthesizing AAV1:

[0260]

[0261] The mixture of I0 (1.00 equivalent), I0-1 (2.20 equivalent), tetrakis(triphenylphosphine)palladium(O)Pd(PPh3)4 (0.04 equivalent; CAS: 14221-01-3), and potassium carbonate (K2CO3; 4.00 equivalent) was stirred overnight at 110 °C in a dioxane:water (4:1 v / v) mixture under a nitrogen atmosphere. After cooling to room temperature (RT), the reaction mixture was extracted between DCM and brine, and the phases were separated. The combined organic layers were dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to obtain AAV1 as a solid. Boric acid can be used instead of borate esters.

[0262] General steps for synthesizing AAV2:

[0263]

[0264] I1 (1.00 equivalent) and liquid bromine (4.0 equivalent; CAS 7726-95-6) were stirred overnight at room temperature in anhydrous dimethylformamide (DMF) under a nitrogen atmosphere. The reaction mixture was poured into water. The precipitate was filtered off and washed with water and ethanol. The crude product obtained was purified by recrystallization or column chromatography to obtain AAV2 as a solid.

[0265] General steps for synthesizing AAV3:

[0266]

[0267] Wherein, X is a halogen selected from the group consisting of F, Cl, Br, and I. In some embodiments, X is F.

[0268] I₂ (1.00 equivalent) was dissolved in THF or tert-butylbenzene under a nitrogen atmosphere, followed by the sequential addition of n-butyllithium or tert-butyllithium (4.0 equivalent) and I₂⁻ (3.0 equivalent), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was extracted between DCM and brine, and the phases were separated. The combined organic layers were dried over anhydrous MgSO₄, and the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography.

[0269] General steps for synthesizing AAV2a:

[0270]

[0271] I1a (1.00 equivalent) and liquid bromine (2.2 equivalent; CAS 7726-95-6) were stirred overnight in chloroform at room temperature under a nitrogen atmosphere. The reaction mixture was extracted between dichloromethane and a saturated sodium thiosulfate solution, and the phases were separated. The combined organic layers were dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to give I2a as a solid.

[0272] General steps for synthesizing AAV3a:

[0273]

[0274] In some embodiments, R2 is C6-C 18 Aryl group, wherein one or more hydrogen atoms may optionally be substituted independently of each other by a C1-C5 alkyl group, Ph, CN, CF3 or F.

[0275] I₂a (1.00 equivalent) was dissolved in toluene under a nitrogen atmosphere, followed by the sequential addition of tris(dibenzylacetone)dipalladium(0) (CAS: 51364-51-3; 0.04 equivalent), I₂a-1 (5.0 equivalent), X-Phos (CAS: 564483-18-7; 0.16 equivalent), and tripotassium phosphate (CAS: 7778-53-2; 4.00 equivalent). The reaction mixture was stirred overnight at 110 °C. The reaction mixture was extracted between DCM and brine, and the phases were separated. The combined organic layers were dried over anhydrous MgSO₄, and the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography.

[0276] General Synthesis Scheme II

[0277] General Synthesis Scheme II provides a synthetic scheme for an organic molecule used in the invention, wherein T = R 1 And V = R2 :

[0278]

[0279]

[0280] Wherein, X is a halogen selected from the group consisting of F, Cl, Br and I. Preferably, X is F.

[0281] The reaction steps were carried out under conditions similar to those described in General Scheme I for AAV1, AAV2, and AAV3.

[0282] Cyclic voltammetry

[0283] Cyclic voltammograms were obtained by reacting a sample in dichloromethane or a suitable solvent with a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) at a concentration of 10... -3 Measurements were taken at a solution concentration of mol / L for organic molecules. Measurements were performed at room temperature under a nitrogen atmosphere using a three-electrode assembly (working and counter electrodes: Pt wires, reference electrode: Pt wires), and using FeCp2 / FeCp2... + Calibration was performed using ferrocene as an internal standard. HOMO data were corrected for the saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0284] Density functional theory calculations

[0285] The molecular structure was optimized using the BP86 functional and the resolution of identity approach (RI). Excitation energies were calculated using the BP86-optimized structure via time-dependent DFT (TD-DFT). Orbital and excited-state energies were calculated using the B3LYP functional. The Def2-SVP basis set and an m4 grid were used for numerical integration. The Turbomole package was used for all calculations.

[0286] Optical physical measurement

[0287] Sample pretreatment: spin coating.

[0288] Instruments: Spin150, SPS euro.

[0289] The sample concentration was 0.2 mg / mL, dissolved in toluene / DCM.

[0290] Program: Apply at 2000 U / min for 7 to 30 seconds. After coating, dry the film at 70°C for 1 minute.

[0291] Photoluminescence and phosphorescence spectra

[0292] For the analysis of phosphorescence and fluorescence spectra, a fluorescence spectrometer "Fluoromax4P" from Horiba was used.

[0293] Time-resolved PL spectra in the μs and ns ranges (FS5)

[0294] Time-resolved photon emission (PL) measurements were performed on an FS5 fluorescence spectrometer from Edinburgh Instruments. The better light focusing allowed for an optimized signal-to-noise ratio compared to measurements on the HORIBA setup, which is advantageous for the FS5 system, especially for transient PL measurements of delayed fluorescence characteristics. The FS5 consists of a xenon lamp providing a broad spectrum. The continuous light source is a 150W xenon arc lamp, with the selected wavelength chosen via a Czerny-Turner monochromator, which is also used to set specific emission wavelengths. A sample emission pointing-sensitive R928P photomultiplier tube (PMT) allows detection of single photons with peak quantum efficiencies up to 25% in the spectral range from 200 nm to 870 nm. The detector is a temperature-stable PMT providing dark counts below 300 cps (counts per second). Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions was applied. This was done by using the corresponding amplitude A... i For a specific lifetime τ i Weighting,

[0295]

[0296] The delayed fluorescence lifetime τ was determined. DF .

[0297] Photoluminescence quantum yield measurement

[0298] For photoluminescent quantum yield (PLQY) measurements, an absolute PL quantum yield measurement system (Hamamatsu Photonics) C9920-03G was used. Quantum yield and CIE coordinates were determined using software version U6039-05 3.6.0.

[0299] The maximum emission value is given in nm, the quantum yield Φ is given in % and the CIE coordinates are given as x and y values.

[0300] PLQY is determined using the following protocol:

[0301] 1) Quality Assurance: Anthracene (known concentration) in ethanol is used as a reference.

[0302] 2) Excitation wavelength: Determine the maximum absorption value of organic molecules and use this wavelength to excite the molecules.

[0303] 3) Measurement

[0304] For the sample, the quantum yield of the solution or membrane is measured under a nitrogen atmosphere. The yield is calculated using the equation:

[0305]

[0306] Where, n 光子 Indicates photon count, and Int. indicates intensity.

[0307] Fabrication and characterization of optoelectronic devices

[0308] Optoelectronic devices (such as OLED devices) comprising organic molecules according to the invention can be fabricated via vacuum deposition (vacuum evaporation). If the layer contains more than one compound, the weight percentage of one or more compounds is given as %. 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%.

[0309] The not-fully-optimized OLED was characterized using standard methods and by measuring the electroluminescence spectrum and intensity-dependent external quantum efficiency (in%), which was calculated using light and current detected by a photodiode. The OLED device lifetime was extracted from the change in brightness during operation at a constant current density. The LT50 value corresponds to the time when the measured brightness decreases to 50% of the initial brightness; similarly, LT80 corresponds to the time when the measured brightness decreases to 80% of the initial brightness, LT95 corresponds to the time when the measured brightness decreases to 95% of the initial brightness, and so on.

[0310] Accelerated lifetime measurements are performed (e.g., by applying increased current density). For example, the following equation is used to determine the lifetime at 500 cd / m 2 The following LT80 value:

[0311]

[0312] Where L0 represents the initial brightness under the applied current density.

[0313] This value corresponds to the average of several (typically 2 to 8) pixels, giving the standard deviation among these pixels.

[0314] HPLC-MS

[0315] HPLC-MS analysis was performed on an Agilent (1260 series) HPLC system equipped with an MS detector (Thermo LTQ XL).

[0316] For example, a typical HPLC method is as follows: An Agilent reversed-phase column (Poroshell 120EC-C18, 3.0 mm × 100 mm, 2.7 μm particle size) is used in the HPLC. HPLC-MS measurements are performed at room temperature (rt) according to a gradient.

[0317]

[0318] Use the following solvent mixture containing 0.1% formic acid:

[0319] Solvent A: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent B: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent C: THF (50%) MeCN (50%)

[0320] A 2 μL sample is taken from a solution containing an analyte at a concentration of 0.5 mg / mL for measurement.

[0321] Ionize the probe using an atmospheric pressure chemical ionization (APCI) source in positive (APCI+) or negative (APCI-) ionization mode, or an atmospheric pressure photoionization (APPI) source.

[0322] Example 1

[0323]

[0324] Synthesize Example 1 according to General Synthesis Scheme I and the following steps:

[0325] AAV3 (27% yield), of which, (CAS 869340-02-3) is used as reactant I2, and dimethyltrimethylfluoroborane (CAS 436-59-9) is used as reactant I2-1.

[0326] MS (HPLC-MS), m / z (retention time): 783.45 (15.92 min).

[0327] Example 1 (0.001 mg / mL, in dichloromethane (DCM)) showed a maximum emission at 464 nm (2.67 eV), a full width at half maximum (FWHM) of 0.24 eV, and a CIEy coordinate of 0.17. The starting point of the emission spectrum was determined at 2.79 eV.

[0328] Example 1 (1%, in PMMA) has a maximum emission at 462 nm, a full width at half maximum (FWHM) of 0.26 eV, and a CIEy coordinate of 0.17. The starting point of the emission spectrum is determined at 2.81 eV.

[0329] Example 2

[0330]

[0331] Synthesize Example 2 according to General Synthesis Scheme I and the following steps:

[0332] AAV3 (53% yield), of which, (CAS 27973-29-1) is used as reactant I2, and dimethyltrimethylfluoroborane (CAS 436-59-9) is used as reactant I2-1.

[0333] MS (HPLC-MS), m / z (retention time): 698.43 (7.42 min).

[0334] Example 2 (0.001 mg / mL, in dichloromethane (DCM)) showed a maximum emission at 441 nm (2.81 eV) and a CIEy coordinate of 0.06. The starting point of the emission spectrum was determined at 2.93 eV.

[0335] Example 3

[0336]

[0337] Synthesize Example 3 according to General Synthesis Scheme I and the following steps:

[0338] AAV1, where, (CAS 27973-29-1) used as reactant I0 (CAS1392512-54-7) is used as reactant I0-1

[0339] AAV2

[0340] And AAV3, wherein 1,6-dibromo-3,8-bis(4-fluoro-2,6-dimethylphenyl)pyrene is used as reactant I2, and dimethoxyfluoroborane (CAS 436-59-9) is used as reactant I2-1.

[0341] Example 4

[0342]

[0343] Synthesize Example 4 according to General Synthesis Scheme I and the following steps:

[0344] AAV1, where, (CAS 27973-29-1) is used as reactant I0. (CAS1423-27-4) is used as reactant I0-1

[0345] AAV2

[0346] AAV3, wherein 1,6-dibromo-3,8-bis(2-(trifluoromethyl)phenyl)pyrene is used as reactant I2, and dimethoxyfluoroborane (CAS 436-59-9) is used as reactant I2-1.

[0347] Example 5

[0348]

[0349] Synthesize Example 5 according to General Synthesis Scheme I and the following steps:

[0350] AAV2a (70% yield), wherein Example 2 is used as reactant I1a; and

[0351] AAV3a (2% yield), wherein 2,4,6-trimethylphenylboronic acid (CAS 5980-97-2) is used as reactant I2a-1.

[0352] Example 5 (1%, in PMMA) shows a maximum emission at 452 nm, a full width at half maximum (FWHM) of 0.30 eV, and a CIEy coordinate of 0.13. The starting point of the emission spectrum was determined at 2.88 eV.

[0353] Example D1

[0354] Example 1 was tested in an OLED D1 that was manufactured with the following layer structure:

[0355]

[0356]

[0357] OLED D1 at 1000cd / m 2 An external quantum efficiency (EQE) of 8.7% was achieved. The maximum emission at 4.9 V was 469 nm with a free wave size (FWHM) of 46 nm. The corresponding CIEx value was 0.12, and the CIEy value was 0.21. This was determined at 1200 cd / m². 2 The LT95 value is 7.1 hours.

[0358] Example D2

[0359] Example 2 was tested in an OLED D2 that was manufactured with the following layer structure:

[0360]

[0361] OLED D2 at 1000cd / m 2An external quantum efficiency (EQE) of 7.9% was achieved. The emission peak at 6.1 V was 452 nm with an FWHM of 46 nm. The corresponding CIEx value was 0.14, and the CIEy value was 0.10. This was determined at 1200 cd / m². 2 The LT95 value is 7.4 hours.

[0362] Additional examples of the invented organic molecules

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

Claims

1. An organic molecule, said organic molecule having the structure of formula IIIa: Formula IIIa, in, R 1 In each occurrence, it follows the structure of Equation II: Formula II, Formula II is combined through the positions marked by the dashed lines; Ar 1 Each occurrence is independently selected from the group consisting of: Formula IIa Formula IIb Formula IIc Formula IId Formula IIe Formula IIf Formula IIg Formula IIh, Each of equations IIa to IIh is transmitted via " The marked position is attached to the boron atom in Formula II; R 2 Selected from the group consisting of: i Pr; and Ph, wherein one or more hydrogen atoms are optionally substituted independently of each other by C1-C5 alkyl, Ph, CN, CF3 or F.

2. The organic molecule according to claim 1, wherein, R 1 Selected from the group consisting of: Formula IIa-2 Formula IIb-2 Formula IIc-2 Formula IId-2 Formula IIe-2 Formula IIf-2 Formula IIg-2 Formula IIh-2.

3. The organic molecule according to claim 1, wherein the organic molecule is selected from the following compounds: 。 4. The application of an organic molecule according to any one of claims 1 to 3 as a light emitter in an optoelectronic device.

5. The application according to claim 4, wherein, The optoelectronic device is selected from the group consisting of: Luminescent electrochemical cells; Organic diodes; Organic solar cells; Organic transistors; Organic lasers; and Down-conversion element.

6. The application according to claim 5, wherein, The organic diode is an organic light-emitting diode, and the organic transistor is an organic field-effect transistor.

7. The application according to claim 5, wherein, The organic diode is an organic light-emitting diode sensor, and the organic transistor is an organic field-effect transistor.

8. A composition comprising: (a) The organic molecule according to any one of claims 1 to 3, in the form of an emitter and / or a host; (b) an emitter and / or host material different from the organic molecule; and (c) Optionally, dyes and / or solvents.

9. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 3 or a composition according to claim 8, wherein the optoelectronic device is in the form of a device selected from the group consisting of a luminescent electrochemical cell, an organic diode, an organic solar cell, an organic transistor, an organic laser, and a downconversion element.

10. The optoelectronic device according to claim 9, wherein the optoelectronic device comprises: Base; anode; and A cathode, wherein the anode or the cathode is disposed on the substrate; as well as A light-emitting layer is disposed between the anode and the cathode and includes the organic molecules or the composition.

11. The optoelectronic device according to claim 9, wherein, The organic diode is an organic light-emitting diode, and the organic transistor is an organic field-effect transistor.

12. The optoelectronic device according to claim 9, wherein, The organic diode is an organic light-emitting diode sensor, and the organic transistor is an organic field-effect transistor.

13. A method for manufacturing an optoelectronic device, wherein, The method, using an organic molecule according to any one of claims 1 to 3 or a composition according to claim 8, includes the step of treating the organic molecule by vacuum evaporation or from solution.

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