Organic molecules for optoelectronic devices

Abstract

The compound includes a structure of formula I below, wherein Z is independently a direct bond, NR a , O and S; R a and R b are independently hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , O.S.O. 2 R 5 , C.F. 3 , C.N., F., Br., I., C. 1 -C 40 Alkyl, C 1 -C 40 Alkoxy, C 1 -C 40 Thioalkoxy, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 6 -C 60 Aryl and C 2 -C 57 An organic molecule selected from the group consisting of heteroaryl. TIFF2024540879000065.tif8168

Description

[Technical field]

[0001] The present invention relates to light-emitting organic molecules and oligomers comprising a plurality of such organic molecules as oligomeric units, and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]

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

[0003] Such objectives are achieved by the present invention, which provides novel organic molecules.

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

[0005] According to the invention, the organic molecules exhibit an emission maximum in the yellow, orange or red spectral range. The organic molecules exhibit an emission maximum in particular between 570 nm and 800 nm, preferably between 580 nm and 700 nm, more preferably between 590 nm and 690 nm, even more preferably between 610 nm and 665 nm. The photoluminescence quantum yield of the organic molecules according to the invention is in particular greater than 30%. The use of the organic molecules according to the invention in optoelectronic devices, for example organic light-emitting diodes (OLEDs), leads to higher efficiency of the device or higher color purity, expressed as the full width at half maximum (FWHM) of the emission. The corresponding OLEDs have a higher stability than OLEDs with known emitter substances and similar hues. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] Organic molecules according to the invention In a first aspect, the present invention relates to an organic molecule comprising or consisting of a structure of formula I:

[0007] [ka]

[0008] Z, in each occurrence, independently, is a direct bond, NR a , O and S; R a and R b is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , O.S.O. 2 R 5 , C.F. 3 ,CN,F,Br,I, C 1 -C 40 Alkyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 1 -C 40 Alkoxy, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 1 -C 40 Thioalkoxy, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 2 -C 40 Alkenyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2, Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 2 -C 40 Alkynyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by Optionally, one or more substituents R 5 C replaced with 6 -C 60 Aryl, and Optionally, one or more substituents R 5 C replaced with 2 -C 57 Heteroaryl, R 5 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , B(R 6 ) 2 , O.S.O. 2 R 6 , C.F.3 ,CN,F,Br,I, C 1 -C 40 Alkyl, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 1 -C 40 Alkoxy, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 1 -C 40 Thioalkoxy, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 2 -C 40 Alkenyl, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 2 -C 40 Alkynyl, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by Optionally, one or more substituents R 6 C replaced with 6 -C 60 Aryl, and Optionally, one or more substituents R 6 C replaced with 2 -C 57 Heteroaryl, R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh (Ph=phenyl), CF 3 ,C.N.,F. C 1 -C 5 Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 1 -C 5 Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 1 -C 5 Thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 2 -C 5 Alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 2 -C 5 Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, Optionally, 1 or more C 1 -C 5 C substituted with alkyl substituents 6 -C 18 Aryl, Optionally, 1 or more C 1 -C 5C substituted with alkyl substituents 2 -C 17 Heteroaryl, N(C 6 -C 18 Aryl) 2 , N(C 2 -C 17 Heteroaryl) 2 , and N(C 2 -C 17 Heteroaryl)(C 6 -C 18 aryl), where the optional substituent R a , R b , R 5 and R 6 independently represents one or more substituents R a , R b , R 5 and / or R 6 Together with the ring system may form mono- or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems.

[0009] In one embodiment, the organic molecule comprises or consists of a structure of Formula Ia, Ib, or Ic:

[0010] [ka] TIFF2024540879000004.tif8453TIFF2024540879000005.tif8354.

[0011] In one embodiment, the organic molecule comprises or consists of a structure of Formula Id, Formula Ie, or Formula If:

[0012] [ka] TIFF2024540879000007.tif8355TIFF2024540879000008.tif8459.

[0013] In a preferred embodiment, Z is, in each occurrence, independently of one another, NR a and O.

[0014] In a preferred embodiment, the organic molecule comprises or consists of the structure of Formula II-1 and Formula II-2:

[0015] [ka] TIFF2024540879000010.tif7374.

[0016] In one embodiment, the organic molecule comprises or consists of the structure of Formula IIa:

[0017] [ka] .

[0018] In one embodiment of the present invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, N(Ph) 2 .

[0019] In one embodiment of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, N(Ph) 2 .

[0020] In one embodiment, the organic molecule comprises or consists of the structure of formula IIa-1:

[0021] [ka] .

[0022] In one embodiment, the organic molecule comprises or consists of a structure of formula IIa-2, IIa-3, IIa-4, or IIa-5:

[0023] [ka] TIFF2024540879000014.tif7579TIFF2024540879000015.tif11082TIFF2024540879000016.tif10481.

[0024] In one embodiment, the organic molecule comprises or consists of the structure of formula IIa-1, where adjacent R a The substituents may independently form mono- or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems.

[0025] In one embodiment, the organic molecule comprises or consists of a structure of formula IIb-1, IIb-2, IIb-3, or IIb-4:

[0026] [ka] TIFF2024540879000018.tif7883TIFF2024540879000019.tif6882TIFF2024540879000020.tif8978.

[0027] In one embodiment, the organic molecule comprises or consists of the structure of Formula III:

[0028] [ka] .

[0029] In one embodiment, the organic molecule comprises or consists of the structure of formula IVa, IVb, IVc, IVd, IVe, and IVf:

[0030] [ka] TIFF2024540879000023.tif8280TIFF2024540879000024.tif8568TIFF2024540879 000025.tif8364TIFF2024540879000026.tif8366TIFF2024540879000027.tif8367.

[0031] In one embodiment, the organic molecule comprises or consists of the structure of Formula V:

[0032] [ka] .

[0033] In one embodiment, the organic molecule comprises or consists of the structure of formula V-1, formula V-2, or formula V-3:

[0034] [ka] TIFF2024540879000030.tif7472TIFF2024540879000031.tif7887.

[0035] In one embodiment, the organic molecule comprises or consists of the structure of formula IVa, IVb, IVc, IVd, IVe, or IVf:

[0036] [ka] TIFF2024540879000033.tif8369TIFF2024540879000034.tif8669TIFF2024540879 000035.tif8474TIFF2024540879000036.tif8468TIFF2024540879000037.tif8570 TIFF2024540879000038.tif8368TIFF2024540879000039.tif8474TIFF2024540879 000040.tif8666TIFF2024540879000041.tif8466TIFF2024540879000042.tif8370.

[0037] In one embodiment, the organic molecule comprises or consists of the structure of formula V-3: a The substituents may independently form mono- or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems.

[0038] In one embodiment, the organic molecule comprises or consists of the structure of formula V-3a:

[0039] [ka] .

[0040] In one embodiment of the present invention, R b are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, N(Ph) 2 .

[0041] The present invention also provides an oligomer for use as an emitter in an optoelectronic device, the oligomer comprising, or consisting of, a plurality (i.e., 2, 3, 4, 5 or 6) of units of formula VI:

[0042] [ka] .

[0043] The oligomers are dimers to hexamers (m=2 to 6), in particular dimers to trimers (m=2 or 3), or preferably dimers (m=2). -having a plurality of units of formula VI, - a plurality of units represented by chemical formula VI are linked via a linking group selected from the group consisting of a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, an anthracene group, a pyrene group, a pyridine group, a pyrimidine group, and a triazine group; - a plurality of units are linked together such that the ring a and / or ring b in the unit of formula VI-AB is shared with at least one other adjacent unit of the oligomer;

[0044] [ka] - the units of the oligomer are linked together such that ring a and / or ring b of any unit is fused to ring a and / or ring b of an adjacent unit of the oligomer.

[0045] In one embodiment, the organic molecule comprises or consists of the structure of Formula VIIIa or Formula VIIIb:

[0046] [ka] TIFF2024540879000047.tif76125.

[0047] definition As used throughout this specification, the term "cyclic group" is understood in its broadest sense to refer to any monocyclic, bicyclic or polycyclic moiety.

[0048] As used throughout this specification, the terms "ring" and "ring system" are understood in the broadest sense to refer to any monocyclic, bicyclic or polycyclic moiety.

[0049] As used throughout this specification, the term "carbocycle" is understood in its broadest sense as any cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen or any other substituent as defined in certain embodiments of the invention. The term "carbocyclic" is also understood as an adjective, referring to a cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen or any other substituent as defined in certain embodiments of the invention.

[0050] As used throughout this specification, the term "heterocycle" is understood in the broadest sense as any cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The term "heterocyclic" is also understood as an adjective and refers to a cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The heteroatoms can be the same or different in each case and can be individually selected from the group consisting of N, O, S and Se, unless otherwise specified in a specific embodiment. It goes without saying that all carbon atoms or heteroatoms contained in a heterocycle in the context of the present invention can be substituted with hydrogen or any other substituent defined in a specific embodiment of the present invention.

[0051] As used throughout this specification, the term "aromatic ring system" is understood in its broadest sense as any bicyclic or polycyclic aromatic moiety.

[0052] As used throughout this specification, the term "heteroaromatic ring system" is understood in its broadest sense as any bicyclic or polycyclic heteroaromatic moiety.

[0053] As used throughout this specification, when referring to an aromatic or heteroaromatic ring system, the term "fused" means that the "fused" aromatic or heteroaromatic rings share at least one bond that is part of both ring systems. For example, naphthalene (or naphthyl when referred to as a substituent) or benzothiophene (or benzothiophenyl when referred to as a substituent) are considered as fused aromatic ring systems in the context of the present invention, where the two benzene rings (in the case of naphthalene) or thiophene and benzene (in the case of benzothiophene) share one bond. Sharing a bond in such a context is also understood to include sharing the two atoms that constitute each bond, and a fused aromatic or heteroaromatic ring system is also understood as one aromatic or heteroaromatic system. It is also understood that one or more bonds are shared by the aromatic or heteroaromatic rings that constitute the fused aromatic or heteroaromatic ring system (e.g., in pyrene). Aliphatic ring systems may also be fused, which will be understood to have the same meaning as aromatic or heteroaromatic ring systems, except that a fused aliphatic ring system is not aromatic.

[0054] As used throughout this specification, the terms "aryl" and "aromatic" are understood in the broadest sense as any monocyclic, bicyclic or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Nevertheless, throughout this specification, the number of aromatic ring atoms may be given in subscript numbers in the definitions of specific substituents. In particular, a heteroaromatic ring contains 1 to 3 heteroatoms. Furthermore, the terms "heteroaryl" and "heteroaromatic" are understood in the broadest sense as any monocyclic, bicyclic or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatom may be the same or different in each case, and may be individually selected from the group consisting of N, O, S and Se, unless otherwise stated in a specific embodiment. Thus, the term "arylene" refers to a divalent substituent that possesses two attachment sites to other molecular structures and serves as a linker structure. In exemplary embodiments, if a group is defined differently from the definitions given herein, for example, if the number of aromatic ring atoms or the number of heteroatoms differs from the definitions given, the definitions in the exemplary embodiments apply. In accordance with the present invention, a fused (annulated) aromatic or heteroaromatic polycycle is composed of two or more single aromatic or heteroaromatic rings that form the polycycle via a condensation reaction.

[0055] In particular, as used throughout this specification, the term "aryl group" or "heteroaryl group" refers to any of the following: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, selenophene, benzoselenophene, isobenzoselenophene, dibenzoselenophene; pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazoline,

[0033] The aromatic or heteroaromatic groups include those derived from azole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or combinations of the aforementioned groups, which may be attached via any position of the aromatic or heteroaromatic group.

[0056] As used throughout this specification, the term "aliphatic" when referring to a ring system is also understood in its broadest sense to mean that none of the rings constituting the ring system are aromatic or heteroaromatic. Such aliphatic ring systems are also understood to be fused to one or more aromatic rings, making some, but not all, of the carbon atoms or heteroatoms contained in the core structure of the aliphatic ring system part of the aromatic ring to which they are attached.

[0057] As used herein, the term "alkyl group" is understood in the broadest sense as any linear, branched or cyclic alkyl substituent. In particular, the term "alkyl" includes the substituents methyl (Me), ethyl (Et), n-propyl (N-propyl ... ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-Butyl ( i Bu), s-Butyl ( s Bu), t-Butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n -octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n- des-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexades-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec- 1-yl, 1,1-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.

[0058] As used herein, the term "alkenyl" includes straight-chain, branched and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0059] As used herein, the term "alkynyl" includes straight-chain, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0060] As used herein, the term "alkoxy" includes straight chain, branched and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

[0061] As used herein, the term "thioalkoxy" includes straight chain, branched and cyclic thioalkoxy substituents, where the O in the exemplary alkoxy group is replaced with an S.

[0062] As used herein, the terms "halogen" and "halo" are also understood in the broadest sense, preferably fluorine, chlorine, bromine or iodine.

[0063] When a molecular fragment is described as being a substituent or attached to another moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above ways of describing a substituent or an attached fragment are considered equivalent.

[0064] All hydrogen atoms (H) contained in any structure referred to in this application are also replaced, in each case independently of one another, with deuterium (D), unless specifically stated otherwise. The replacement of hydrogen with deuterium is common practice and will be apparent to those skilled in the art. Thus, there are many well-known methods by which it can be achieved and many review articles describing it (e.g. A. Michelotti, M. Roche, Synthesis 2019, 51(06), 1319-1328, DOI:10.1055 / s-0037-1610405; J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. Int. Ed. 2007, 46(15), 7744-7765, DOI:10.1002 / anie.200700039; Y. Sawama, Y. Monguchi, H. Sajiki, Synlett 2012, 23(7), 959-972, DOI:10.1055 / s-0031-1289696).

[0065] When a molecular fragment is described as being a substituent or attached to another moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above ways of describing a substituent or an attached fragment are considered equivalent.

[0066] In one embodiment of the present invention, the organic molecules according to the present invention have an emission peak in the visible or near ultraviolet range, i.e., in the wavelength range of 380 to 800 nm, with a half-width 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 less than 0.18 eV, in a solution in an organic solvent, in particular a dichloromethane (DCM), toluene or chloroform solution, or in a poly(methyl methacrylate) (PMMA) film having 1 to 5 wt. %, in particular 2 wt. %, of the organic molecules at room temperature.

[0067] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperature, typically 77K. Phosphorescence is typically visible in the normal state spectrum in a film of 2% emitter and 98% PMMA, or in organic solvents, particularly DCM, toluene or chloroform. The triplet energy is therefore also determined as the onset of the phosphorescence spectrum. For fluorescent emitter molecules, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77K.

[0068] The photoluminescence quantum yield of the organic molecules according to the invention is in particular 30% or more, preferably more than 50%, more preferably more than 70%, even more preferably more than 80% or even more preferably more than 90% in a solution of 0.001 mg / mL of the organic molecules according to the invention in an organic solvent, in particular dichloromethane (DCM), toluene or chloroform, at room temperature.

[0069] The onset of the emission spectrum is determined by calculating the intersection point of a tangent to the emission spectrum with the x-axis, the tangent to the emission spectrum being set at the high energy side of the emission band and at half maximum of the maximum intensity of the emission spectrum.

[0070] In one embodiment, the organic molecule according to the invention has an onset of the emission spectrum that is energetically close to the maximum emission, i.e. the energy difference between the onset of the emission spectrum and the energy of the maximum emission is less than 0.14 eV, preferably less than 0.13 eV, or even more preferably less than 0.12 eV, at room temperature, at 0.001 mg / mL of the organic molecule according to the invention in toluene or DCM, and the full width at half maximum (FWHM) of said organic molecule 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 more preferably less than 0.18 eV.

[0071] Further aspects and embodiments of the present invention A further aspect of the present invention relates to the use of the organic molecules according to the invention as light emitters or absorbers and / or host materials and / or electron transport materials and / or hole injection materials and / or hole blocking materials in optoelectronic devices.

[0072] A preferred embodiment concerns the use of organic molecules according to the invention as light emitters in optoelectronic devices.

[0073] The optoelectronic component is understood in the broadest sense as any component based on organic materials that is suitable for emitting light in the visible or near ultraviolet (UV) range, i.e. in the wavelength range from 380 nm to 800 nm. More preferably, the optoelectronic component is capable of emitting light in the visible range, i.e. in the wavelength range from 400 nm to 800 nm.

[0074] In connection with such applications, the optoelectronic device is more specifically selected from the group consisting of: Organic Light Emitting Diode (OLED) Light-emitting electrochemical cells OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside Organic diode ·Organic solar cells Organic transistors Organic field-effect transistors Organic lasers, and Down conversion element.

[0075] For such applications, in preferred embodiments, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light emitting transistor.

[0076] For said applications, in the light-emitting layer in the optoelectronic device, in particular in the OLED, the fraction of the organic molecules according to the invention is 0.1% to 99% by weight, more particularly 1% to 80% by weight. In an alternative embodiment, in the light-emitting layer, the proportion of the organic molecules is 100% by weight.

[0077] In one embodiment, the light-emitting layer comprises an organic molecule according to the present invention as well as a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.

[0078] Host substance H B According to the present invention, one or more host materials H contained in any one of at least one light-emitting layer B B Any of the above may be used as a p-host H P , n-host H showing high electron mobility N or an ambipolar host material H that exhibits both high hole mobility and high electron mobility BP It is also.

[0079] According to the present invention, a p-host H P is the energy E HOMO (H P ) with the highest occupied molecular orbital HOMO (H P ), where preferably, −6.1 eV≦E HOMO (H P )≦−5.6 eV.

[0080] According to the present invention, a p-host H P is the energy E LUMO (H P ) with the lowest unoccupied orbital LUMO(H P ), where preferably, −2.6 eV≦E LUMO (H P ).

[0081] According to the present invention, a p-host H P is the lowest excited singlet state energy level E(S1 p-H ), where preferably E(S1 p-H ) ≧3.0 eV.

[0082] According to the present invention, a p-host H P is the lowest excited triplet state energy level E(T1 p-H ), where preferably E(T p-H )≧2.7 eV.

[0083] A host material H contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B Any requirement or preferred feature previously defined for the p-host H P It is understood that the same is also valid for the following. Therefore, in a preferred embodiment, the relationships represented by the following formulas (6) to (9) apply: E(S1 p-H )>E(S1 E ) (6) E(S1 p-H )>E(S1 S ) (7) E(T1 p-H )>E(T1 S ) (8) E(T1 p-H )>E(T1 E ) (9).

[0084] Therefore, the p-host H P The lowest excited singlet state S1 p-H is the TADF material E B The lowest excited singlet state S1 E It is preferable that the energy is higher than that of the p-host H P The lowest excited singlet state S1 p-His the FWHM of an arbitrary small emitter S B The lowest excited singlet state S1 S It is preferable that the energy is higher than that of the p-host H P The lowest excited triplet state T1 p-H is the FWHM of an arbitrary small emitter S B The lowest excited triplet state T1 S It is preferable that the energy is higher than that of the p-host H P The lowest excited triplet state T1 of p-H is the TADF material E B The lowest excited triplet state T1 E Even higher energies are preferred.

[0085] According to the present invention, the n-host H N is the energy E HOMO (H N ) with the highest occupied molecular orbital HOMO (H N ), wherein preferably, E HOMO (H N )≦−5.9 eV.

[0086] According to the present invention, the n-host H N is the energy E LUMO (H N ) with the lowest unoccupied orbital LUMO(H N ), where preferably, −3.5 eV≦E LUMO (H N )≦−2.9 eV.

[0087] According to the present invention, the n-host H N is the lowest excited singlet state energy level E(S1 n-H ), where preferably E(S1 n-H ) ≧3.0 eV.

[0088] According to the present invention, the n-host H N is the lowest excited triplet state energy level E(T1 n-H ), where preferably E(T n-H )≧2.7 eV.

[0089] A host material H contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B Any requirement or preferred feature previously defined for the n-host H N It is understood that the same is also valid for the following. Therefore, in a preferred embodiment, the relationships expressed by the following formulas (10) to (13) apply: E(S1 n-H )>E(S1 E ) (10) E(S1 n-H )>E(S1 S ) (11) E(T1 n-H )>E(T1 S ) (12) E(T1 n-H )>E(T1 E ) (13).

[0090] Therefore, the n-host H N The lowest excited singlet state S1 n-H is the TADF material E B The lowest excited singlet state S1 E It is preferable that the n-host H N The lowest excited singlet state S1 n-H is the FWHM of an arbitrary small emitter S B The lowest excited singlet state S1 S It is preferable that the n-host H N The lowest excited triplet state T1 n-H is the FWHM of an arbitrary small emitter S B The lowest excited triplet state T1 S Preferably, any n-host HN The lowest excited triplet state T1 n-H is any TADF material E B The lowest excited triplet state T1 E Even higher energy.

[0091] According to the present invention, a bipolar host H is selectively contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention. BP is the energy E LUMO (H BP ) with the lowest unoccupied orbital LUMO(H BP ), where preferably, −3.5 eV≦E LUMO (H BP )≦−2.9 eV.

[0092] According to the present invention, a bipolar host H is selectively contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention. BP is the lowest excited singlet state energy level E(S1 bp-H ), where preferably E(S1 bp-H ) ≧3.0 eV.

[0093] According to the present invention, a bipolar host H is selectively contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention. BP is the lowest excited triplet state energy level E(T1 bp-H ), where preferably E(T bp-H )≧2.7 eV.

[0094] A host material H contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B Any requirement or preferred feature previously defined for the bipolar host H BP It is understood that the same is also valid for the following. Therefore, in a preferred embodiment, the relationships represented by the following formulas (14) to (17) apply: E(S1 bp-H )>E(S1 E ) (14) E(S1bp-H )>E(S1 S ) (15) E(T1 bp-H )>E(T1 S ) (16) E(T1 bp-H )>E(T1 E ) (17).

[0095] Therefore, the bipolar host H BP The lowest excited singlet state S1 bp-H is the TADF material E B The lowest excited singlet state S1 E The higher the energy, the more preferable the bipolar host H BP The lowest excited singlet state S1 bp-H is the FWHM of an arbitrary small emitter S B The lowest excited singlet state S1 S The higher the energy, the more preferable the bipolar host H BP The lowest excited triplet state T1 bp-H is the FWHM of an arbitrary small emitter S B The lowest excited triplet state T1 S Preferably, any bipolar host H BP The lowest excited triplet state T1 bp-H is any TADF material E B The lowest excited triplet state T1 E Even higher energy.

[0096] TADF substance E B According to the invention, one or more thermally activated delayed fluorescent (TADF) substances E B Any of the above is preferably in the lowest excited singlet state S1 E and the lowest excited triplet state T1 E ΔE corresponds to the energy difference between ST The TADF material E according to the present invention is characterized by exhibiting a value of less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, or even less than 0.05 eV. BΔE ST is preferably in the lowest excited triplet state T1 at room temperature (RT). E from the lowest excited singlet state S1 E is small enough to allow thermal recharge (also called up-intersystem crossing or reverse intersystem crossing) of

[0097] In addition, the optoelectronic device according to the present invention includes at least one light-emitting layer B having a small FWHM emitter S B is selectively lowered to ΔE less than 0.4 eV. ST value and is understood to exhibit thermally activated delayed fluorescence (TADF). However, in the context of the present invention, any small FWHM emitter S B This is merely a selective feature. B At least one small FWHM emitter S B While the primary contribution to the emission bandwidth of the optoelectronic device according to the invention is preferably provided by at least one small FWHM emitter S B The TADF material E in the context of the present invention can be attributed to the emission of B is preferably a small FWHM emitter S in the context of the present invention. B is different from.

[0098] According to the present invention, the TADF material E contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B is the energy E HOMO (E B ) with the highest occupied molecular orbital HOMO (E B ), where preferably, −6.0 eV≦E HOMO (E B )≦−5.8 eV.

[0099] According to the present invention, the TADF material E contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B is the energy E LUMO (E B ) with the lowest unoccupied orbital LUMO (EB ), where preferably, −3.4 eV≦E LUMO (E B )≦−3.0 eV.

[0100] According to the present invention, the TADF material E contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B is the lowest excited singlet state energy level E(S1 E ), where preferably 2.5 eV≦E(S1 E )≦2.8 eV.

[0101] According to the present invention, the TADF material E contained in any one of at least one light-emitting layer B of the optoelectronic device according to the present invention B is the lowest excited triplet state energy level E(T1 E ), and the preferred range is ΔE ST Together with the above-mentioned preferred ranges for the singlet state energy level E(S E ) are also defined by the above-mentioned preferred ranges.

[0102] A further aspect of the invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention, in particular in the form of an emitter, (b) one or more triplet-triplet annihilation (TTA) host substances other than the organic molecules according to the present invention; (c) optionally, one or more TADF materials, and (d) optionally, one or more dyes and / or one or more solvents.

[0103] A further aspect of the invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention, in particular in the form of an emitter, (b) one or more host materials different from the organic molecules according to the invention, and (c) one or more TADF materials.

[0104] A further aspect of the invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention, in particular in the form of an emitter, (b) one or more host materials different from the organic molecules according to the invention, and (c) one or more phosphorescent materials.

[0105] In certain embodiments, the emissive layer EML comprises (or consists essentially of) a composition comprising or consisting of: (i) 0.1 to 10% by weight, preferably 0.5 to 5% by weight, in particular 1 to 3% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight, of at least one host compound H, (iii) 0.9 to 94.9% by weight, preferably 14.5 to 80% by weight, in particular 24 to 77% by weight, of at least one additional host compound D having a structure different from that of the molecule according to the invention, (iv) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent, and (v) optionally 0 to 30% by weight, in particular 0 to 20% by weight, preferably 0 to 5% by weight, of at least one additional emitter molecule F having a structure different from that of the molecules according to the invention.

[0106] Compositions Comprising One or More TTA Host Materials In a preferred embodiment, in the optoelectronic device of the invention, said light-emitting layer B comprises (or consists of) (i) 10 to 84 weight percent of a TTA material; (ii) 0 to 30% by weight of TADF material E B , (iii) 0.1 to 10% by weight of an emitter according to the invention, and optionally (iv) 0 to 89.9 weight percent of one or more solvents.

[0107] In a preferred embodiment, the sum of the percentages (i) to (iv) is 100% by weight.

[0108] In another preferred embodiment, in the optoelectronic device of the invention, said light-emitting layer B comprises (or consists of) (i) 56 to 90% by weight of TTA material; (ii) 0 to 5 wt% of TADF material E B , (iii) 0.5 to 5% by weight of an emitter according to the invention, and optionally (iv) 0 to 43.5 weight percent of one or more solvents.

[0109] In a preferred embodiment, the sum of the percentages (i) to (iv) is 100% by weight.

[0110] Compositions Comprising One or More TADF Materials In a preferred embodiment, the light-emitting layer B comprises: (i) 10 to 89.9% by weight of one or more p-host compounds H P , (ii) 0 to 79.9% by weight of one or more n-host compounds H N , (iii) 10 to 50 wt. % of one or more TADF materials E B , (iv) 0.1 to 10% by weight of one or more emitters according to the present invention, and (v) 0 to 89.9 weight percent of one or more solvents.

[0111] In one embodiment, the light-emitting layer B comprises: (i) 22 to 87.5% by weight of one or more p-host compounds H P , (ii) optionally, 0 to 65.5 wt. % of one or more n-host compounds H N , (iii) 12 to 40 wt. % of one or more TADF materials E B , (iv) 0.5 to 5% by weight of one or more emitters according to the invention, and (v) 0 to 65.5 weight percent of one or more solvents.

[0112] Compositions containing one or more phosphorescent materials In a preferred embodiment, H N is optional, in the optoelectronic device of the invention, said light-emitting layer B comprises (or consists of): (i) 10 to 84.9 wt % of p-host compound H P , (ii) 0 to 84.9% by weight of n-host compound H N , (iii) 5 to 15% by weight of phosphorescent material E B , (iv) 0.1 to 10% by weight of an emitter according to the invention, and optionally (v) 0 to 84.9 weight percent of one or more solvents.

[0113] In a preferred embodiment, H N is optional, in the optoelectronic device of the invention, said light-emitting layer B comprises (or consists of): (i) 22 to 70.5 wt % of p-host compound H P , (ii) 0 to 70.5% by weight of n-host compound H N , (iii) 5 to 10% by weight of phosphorescent material E B , (iv) 0.5 to 5% by weight of an emitter according to the invention, and optionally (v) 0 to 72.5 weight percent of one or more solvents.

[0114] Preferably, energy is transferred from the host compound H to one or more organic molecules according to the invention, in particular from the first excited triplet state T1(H) of the host compound H to the first excited triplet state T1(E) of one or more organic molecules E according to the invention and / or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of one or more organic molecules E according to the invention.

[0115] In one embodiment, the host compound H has an energy E in the range of −5 to −6.5 eV. HOMO(H), and at least one additional host compound D has a highest occupied molecular orbital HOMO (H) with energy E HOMO (D) has the highest occupied molecular orbital HOMO (D), where E HOMO (H)>E HOMO (D).

[0116] In a further embodiment, the host compound H has an energy E LUMO (H), and at least one additional host compound D has a lowest unoccupied molecular orbital LUMO (H) with energy E LUMO (D) has a lowest unoccupied molecular orbital LUMO (D), where E LUMO (H)>E LUMO (D).

[0117] In one embodiment, the host compound H has an energy E HOMO (H) highest occupied molecular orbital HOMO(H), with energy E LUMO (H) having a lowest unoccupied molecular orbital LUMO (H); At least one additional host compound D has an energy E HOMO The highest occupied molecular orbital (HOMO) with (D) and energy E LUMO has a lowest unoccupied molecular orbital (LUMO) (D); The organic molecule E according to the present invention has energy E HOMO (E) highest occupied molecular orbital HOMO (E), with energy E LUMO (E) having a lowest unoccupied molecular orbital LUMO (E); Where: E HOMO (H)>E HOMO (D) and the energy level of the highest occupied molecular orbital (HOMO) (E) of the organic molecule according to the present invention (E HOMO (E)) and the energy level of the highest occupied molecular orbital (HOMO) of the host compound H (E HOMO (H)) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV, or -0.1 eV to 0.1 eV; E LUMO (H)>ELUMO (D) and the energy level of the lowest unoccupied molecular orbital (LUMO) (E) of the organic molecule according to the present invention (E LUMO (E)) and the energy level of the lowest unoccupied molecular orbital (LUMO) (D) of at least one additional host compound D (E LUMO The difference from (D)) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV, or -0.1 eV to 0.1 eV.

[0118] In one embodiment of the present invention, the host compound D and / or the host compound H is a thermally activated delayed fluorescence (TADF) material. The TADF material has a wavelength of 2500 cm -1 ΔE corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) of less than ST Preferably, the TADF material has a 3000 cm -1 less than 1500 cm -1 less than 1000 cm -1 Less than or extremely less than 500cm -1 Less than ΔE ST Indicates the value.

[0119] In one embodiment, the host compound D is a TADF material and the host compound H is a 2500 cm -1 Larger ΔE ST In a particular embodiment, the host compound D is a TADF material and the host compound H is selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0120] In one embodiment, the host compound H is a TADF material and the host compound D is a 2500 cm -1 Larger ΔE ST In a particular embodiment, the host compound H is a TADF material and the host compound D is selected from the group consisting of 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST).

[0121] In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition as described herein, more particularly a device selected from the group consisting of organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, in particular gas and vapor sensors that are not completely sealed off from the outside world, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and down conversion devices.

[0122] 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.

[0123] In one embodiment of the inventive optoelectronic device, an organic molecule E according to the invention is used as emitter material in the light-emitting layer EML.

[0124] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the inventive composition described herein.

[0125] When the optoelectronic device is an OLED, it can have, for example, the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer Here, the OLED optionally includes layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above.

[0126] Additionally, in one embodiment, the optoelectronic device may include one or more protective layers that protect the device from damaging exposure to harmful substances in the environment including, for example, moisture, vapors and / or gases.

[0127] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Light-emitting layer B 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A Here, the OLED optionally includes layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above.

[0128] In one embodiment of the present invention, the optoelectronic element is an OLED that can have a stacked structure. In this structure, individual units are stacked on top of each other, unlike the common arrangement in which OLEDs are arranged side by side. Mixed light is generated by an OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED, and a red OLED. An OLED that exhibits a stacked structure may also optionally include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally configured as an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0129] In one embodiment of the present invention, the optoelectronic device is an OLED that includes two or more light-emitting layers between an anode and a cathode. In particular, the so-called tandem OLED includes three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and may optionally include additional layers between each light-emitting layer, such as a charge generation layer, a charge blocking layer, or a charge transport layer. In a further embodiment, the light-emitting layers are stacked adjacently. In a further embodiment, the tandem OLED includes a charge generation layer between each two light-emitting layers. Also, adjacent light-emitting layers or light-emitting layers separated by a charge generation layer can be merged.

[0130] The substrate is made of any material or composition of materials. Mostly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g. copper, gold, silver or aluminum film) or a plastic film or a plastic slide can be used, which allows a higher level of flexibility. The anode layer A is made of a material that allows obtaining a mostly (essentially) transparent film. Since at least one of the two electrodes must be (essentially) transparent to allow light emission from the OLED, one of the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such anode layers A may, for example, comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene.

[0131] The anode layer A is made of (essentially) indium tin oxide (ITO) (e.g., InO 3 ) 0.9 (SnO 2 ) 0.1 The roughness of the anode layer A due to the transparent conducting oxide (TCO) is also mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of like charge carriers (i.e. holes) in that the transport of like charge carriers from the TCO to the hole transport layer (HTL) is promoted. The hole injection layer (HIL) is made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonic acid (PSS), MoO 2 , V 2 O 5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent diffusion of metals from the anode layer A into the hole transport layer (HTL). For example, the HIL can be poly-3,4-ethylenedioxythiophene:polystyrenesulfonate (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalene-2-yl)phenylamine (NAPH), N,N'-bis ... It is also composed of N,N'-triphenyl-N,N'-bis-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0132] Adjacent to the anode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles are also used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) is also an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) may be tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′,4″-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or The HTL may also include star-shaped heterocycles such as 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer consisting of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopants may be transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide. The organic dopants may be tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes can be used.

[0133] EBLs may include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0134] Adjacent to the hole transport layer (HTL) is typically located an emissive layer (EML). The emissive layer (EML) comprises at least one emissive molecule. In particular, the EML comprises at least one emissive molecule E according to the invention. In one embodiment, the emissive layer comprises only organic molecules according to the invention. Typically, the EML further comprises one or more host materials H. For example, the host material H may be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), mCP, mCBP, dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), CzSi, dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(diphenylphosphino ... benzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). The host material H should generally be selected to exhibit a first triplet (T1) and a first singlet (S1) energy level that are energetically higher than the first triplet (T1) and the first singlet (S1) energy level of the organic molecule.

[0135] In one embodiment of the present invention, the EML comprises a so-called mixed host system, which has at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises a mixed host system comprising exactly one light-emitting organic molecule according to the present invention, T2T as an electron-dominant host, and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as a hole-dominant host. In a further embodiment, the EML comprises 50-80% by weight, preferably 60-75% by weight, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 10-45% by weight, preferably 15-30% by weight, of T2T, and 5-40% by weight, preferably 10-30% by weight, of an emissive molecule according to the present invention.

[0136] Adjacent to the light-emitting layer (EML) may be an electron-transporting layer (ETL). Any electron transporter may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxides, and sulfones may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may be 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,7-di(2,2'-bipyridin-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) and / or 4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl (BTB). Optionally, the ETL is also doped with a material such as Liq. The electron transport layer (ETL) can also block holes. Alternatively, a hole blocking layer (HBL) is introduced.

[0137] Examples of HBL include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine (BCP), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), and aluminum-tris(8-hydroxyquinoline) (Alq 3), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST) and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0138] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g. Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also comprise or consist of nanoscale silver wires.

[0139] The OLED may optionally further include a protective layer (also called an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The layer may be any of lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li 2 O, BaF 2 , MgO and / or NaF.

[0140] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) also contain one or more host compounds H.

[0141] To additionally modify the emission and / or absorption spectrum of the emissive layer EML, the emissive layer EML may further comprise one or more additional emitter molecules F. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F are molecules having a structure different from that of the molecules E according to the invention. The emitter molecules F are optionally also TADF emitters. Alternatively, the emitter molecules F are optionally also fluorescent and / or phosphorescent emitter molecules capable of shifting the emission and / or absorption spectrum of the emissive layer EML. For example, triplet and / or singlet excitons may be converted to the ground state S 0 Before being relaxed to , the organic emitter molecule according to the invention can be transferred to the emitter molecule F, which can emit light that is typically red-shifted compared to the light emitted by the organic molecule. Optionally, the emitter molecule F can also induce a two-photon effect (i.e., absorption of two photons that are half the maximum absorbed energy).

[0142] Optionally, the optoelectronic device (e.g., an OLED) may also be, for example, an essentially white optoelectronic device, for example comprising at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and / or red light, and, optionally, there may be energy transfer between two or more molecules, as described above.

[0143] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: >380~420nm wavelength range Deep blue: wavelength range >420~480nm Sky blue: Wavelength range >480~500nm Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: Wavelength range of >620~800nm.

[0144] Associated with the emitter molecule, such hues exhibit maximum emission, so for example, a deep blue emitter has a maximum emission in the range >420-480 nm, a sky blue emitter has a maximum emission in the range >480-500 nm, a green emitter has a maximum emission in the range >500-560 nm, and a red emitter has a maximum emission in the range >620-800 nm.

[0145] The red emitter may preferably have a maximum emission below 800 nm, more preferably below 700 nm, even more preferably below 665 nm, or even less than 640 nm. It will typically also be greater than 570 nm, preferably greater than 590 nm, more preferably greater than 610 nm, or even greater than 620 nm.

[0146] Thus, a further aspect of the present invention is 2 and / or an external quantum efficiency of greater than 8%, preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even greater than 20%; and / or an emission maximum between 590 nm and 690 nm, preferably between 610 nm and 665 nm, more preferably between 620 nm and 640 nm; and / or an emission maximum of 500 cd / m 2 and preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, or even more preferably greater than 1000 h. Accordingly, a further aspect of the invention relates to an OLED whose emission exhibits a CIEy color coordinate of greater than 0.25, preferably greater than 0.27, more preferably greater than 0.29, and even more preferably greater than 0.30.

[0147] Further embodiments of the present invention relate to OLEDs that emit light with CIEx and CIEy color coordinates close to the CIEx (=0.708) and CIEy (=0.292) color coordinates of primary red (CIEx=0.708 and CIEy=0.292) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which are suitable for use in UHD displays, e.g., UHD-TVs. In this context, the term "close" refers to the range of CIEx and CIEy coordinates provided at the end of the paragraph. While in commercial applications, a top light-emitting element (where the top electrode is transparent) is typically used, the test element used throughout the present invention shows a bottom light-emitting element (where the bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx colour coordinates of 0.60 to 0.88, preferably 0.61 to 0.83, more preferably 0.63 to 0.78, even more preferably 0.66 to 0.76 or even more preferably 0.68 to 0.73, and / or CIEy colour coordinates of 0.25 to 0.70, preferably 0.26 to 0.55, more preferably 0.27 to 0.45, even more preferably 0.28 to 0.40 or even more preferably 0.29 to 0.35.

[0148] Thus, a further aspect of the present invention is 2 and / or an emission maximum between 590 nm and 690 nm, preferably between 610 nm and 665 nm, more preferably between 620 nm and 640 nm.

[0149] A further aspect of the present invention relates to an OLED that emits light at a well-defined color point. According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the present invention emits light with a FWHM of the 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.

[0150] In a further aspect, the invention relates to a method for producing an optoelectronic component, in which the organic molecules of the invention are used.

[0151] The optoelectronic device, in particular the OLED according to the invention, may be produced by any means of vapor deposition and / or liquid processes. Thus, at least one layer may be - Produced by the sublimation process; -Manufactured by organic vapor phase deposition process, - Produced by a carrier gas sublimation process; - Solution processed or printed.

[0152] The methods used to manufacture optoelectronic devices, in particular OLEDs, according to the present invention are known in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition steps. The individual layers may be deposited using the same or different deposition methods.

[0153] For example, the vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. The individual layers are also processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art.

[0154] Working Example General synthesis method [ka]

[0155] CG 1 In order to introduce the heterocycle E2 at the position of 1 and C.G. 2 is selected as the reaction pair. Preferably, the so-called Suzuki coupling reaction is used, where CG 1 is selected from Cl, Br or I, and CG 2 is selected from a boronic acid group or a boronic ester group (in particular a boronic acid pinacol ester group), or CG 1 is selected from a boronic acid group or a boronic ester group (in particular a boronic acid pinacol ester group), CG 2 is selected from Cl, Br or I.

[0156] General procedure for synthesis AAV1-1: E1 (1.00 equiv., e.g., 5-bromo-N1,N1,N3,N3-tetraphenyl-1,3-benzenediamine, CAS 1290039-73-4), E2 (1.20 equiv.; e.g., (10-phenylanthracen-9-yl)boronic acid, CAS: 1290039-73-4), tris(dibenzylideneacetone)dipalladium(0) (0.01 equiv.; CAS: 51364-51-3), S-Phos (0.04 equiv.; CAS: 657408-07-6), and potassium phosphate (K 3 PO 4 CAS: 7778-53-2, 2.00 equiv.) was stirred in toluene / water at 95° C. for 72 h under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and water. The organic phase was collected and diluted with MgSO 4 Dry with Celite (登録商標)The mixture was treated with ethyl acetate and charcoal, stirred for 1 h, and filtered. The combined organic layers were concentrated under reduced pressure. The crude product was purified by column chromatography or recrystallization to give E3 as a solid.

[0157] AAV2: A solution of E-3 (1.0 equiv.) in dry 1,2-dichlorobenzene (35 mL per mmol of E-3) was added to boron tribromide (99%, CAS-No. 10294-33-4, 4.0 equiv.). The mixture was warmed to room temperature and then heated to 190 °C for 48 h. The mixture was cooled to ambient temperature. The mixture was then extracted with brine / water and dichloromethane and the combined organic layers were washed with MgSO 4 The mixture was dried at 40° C., filtered and concentrated. After purification through recrystallization or column chromatography, the target compound P-1 was obtained as a solid.

[0158] Cyclic Voltammetry Cyclic voltammograms are performed at concentrations of 10 to 150 nm in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). -3 The measurement is performed at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and FeCp 2 / FeCp 2 + The HOMO data were corrected using ferrocene as an internal standard relative to a saturated calomel electrode (SCE).

[0159] Density functional theory calculations The molecular structures were optimized using the BP86 function and the Resolution of Identity (RI) approach. The excitation energies were calculated with the Time-Dependent DFT (TD-DFT) method using the (BP86) optimized structures. The orbital energies and excited state energies were calculated with the B3LYP function. For numerical integration, the Def2-SVP basis set and m4-grid were used. The Turbomole program package was used for all calculations.

[0160] optical physical measurements Sample preparation: spin coating Equipment: Spin150, SPS euro The sample concentration is 0.2 mg / ml dissolved in toluene / DCM.

[0161] Program: 7) 2000 U / min for 30 sec. After coating, the film was dried at 70° C. for 1 min.

[0162] Fluorescence and phosphorescence spectroscopy For phosphorescence and photoluminescence spectroscopy analysis a Horiba fluorescence spectrometer "Fluoromax 4P" is used.

[0163] Time-resolved PL spectroscopy in the μs and ns range (FS5) Time-resolved PL measurements are performed on an FS5 fluorescence spectrometer from Edinburgh Instruments. Better light collection compared to measurements on the HORIBA setup allows an optimized signal-to-noise ratio, making the FS5 system especially advantageous for transient PL measurements of delayed fluorescence properties. The FS5 consists of a xenon lamp providing a broad spectrum. The continuous light source is a 150 W xenon arc lamp and the selected wavelength is selected by a Czerny-Turner monochromator, which is also used to set the specific emission wavelength. The sample emission is directed to a sensitive R928P photomultiplier tube (PMT) capable of detecting single photons with a peak quantum efficiency of up to 25% in the spectral range from 200 nm to 870 nm. The detector is a temperature-stabilized PMT providing dark counts below 300 cps (counts per second). Finally, a tail fit using three exponential functions is applied to determine the transient decay lifetime of the delayed fluorescence. The specific lifetime τ i and the corresponding amplitude A i The delayed fluorescence lifetime τ is calculated by weighting DF is determined.

[0164]

number

[0165] Photoluminescence quantum yield measurement For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0166] Emission maxima are given in nm, quantum yields Φ are given in %, and CIE coordinates are given as x,y values.

[0167] The PLQY is determined using the following protocol:

[0168] 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard.

[0169] 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule.

[0170] 3) Measurement The quantum yield is measured on solution or film samples in a nitrogen atmosphere. The yield is calculated using the following equation:

[0171]

number

[0172] Measurement of emission spectrum The material was dissolved in chloroform and the solution was filtered through a syringe filter. The remaining solution was used to spin coat a 2% film in PMMA. The sample was excited at 291 nm and a 495 nm filter was used for the measurement.

[0173] Fabrication and characterization of optoelectronic devices Optoelectronic devices, particularly OLED devices, comprising the organic molecules according to the present invention can also be manufactured by vacuum deposition methods. When a layer comprises one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so that when no value is specified, the fraction of the compound is the same as the difference between the specified value and 100%.

[0174] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance, similarly LT80 corresponds to the point when the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the point when the measured luminance has decreased to 95% of the initial luminance.

[0175] Accelerated lifetime measurements are performed (e.g. by applying increased current densities), e.g. 500cd / m 2 In the present invention, the LT80 value is determined using the following formula:

[0176]

number

[0177] The value corresponds to the average of several pixels (typically 2-8) and the standard deviation across the pixels is provided.

[0178] HPLC-MS HPLC-MS analysis is performed on an Agilent HPLC (1260 series) equipped with an MS detector (Thermo LTQ XL).

[0179] For example, a typical HPLC method is as follows: A reverse phase column 3.0 mm x 100 mm, particle size 2.7 μm from Agilent (Poroshell 120EC-C18, 3.0 x 100 mm, 2.7 μm HPLC column) is used for HPLC. HPLC-MS measurements are performed at room temperature (rt) with the following gradient:

[0180] [Table 1]

[0181] The following solvent mixtures containing 0.1% formic acid were used:

[0182] [Table 2]

[0183] From the analyte solution at a concentration of 0.5 mg / mL, an injection volume of 2 μL is taken for the measurement.

[0184] The ionization of the probe is by cation (APCI + ) ionization mode or negative (APCI - ) ionization mode, this is performed using an APCI (atmospheric pressure chemical ionization) source or an APPI (atmospheric pressure photoionization) source.

[0185] Example 1 [ka]

[0186] Example 1 was synthesized according to the general synthetic scheme and as follows: AAV1 (46% yield), in which 5-bromo-N1,N1,N3,N3-tetraphenyl-1,3-benzenediamine (CAS 1290039-73-4) was used as reactant E1 and (10-phenylanthracen-9-yl)boronic acid (CAS 1290039-73-4) was used as reactant E2, and AAV2 (2% yield). MS (HPLC-MS), m / z (residence time): 681 (6.63 minutes).

[0187] Emission maximum (λ) of Example 1 (0.005 mg / mL in toluene) max ) is 658 nm, the full width at half maximum (FWHM) is 82 nm (0.22 eV), and the photoluminescence quantum yield (PLQY) is 38%.

[0188] Additional Examples of Organic Molecules of the Invention

[0189] [ka] TIFF2024540879000056.tif224158TIFF2024540879000057.tif202157TIFF2024540879000058.tif252152TIFF2024540879000059.tif205159

Claims

1. An organic molecule comprising the structure of Formula I: 【Chemical 1】 Z in each occurrence independently represents a direct bond, NR ａ , O and S; R ａ and R ｂ is, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R ５ ) ２ , OR ５ , Si(R ５ ) ３ , B(OR ５ ) ２ , B(R ５ ) ２ , OSO ２ R ５ , C.F. ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C １ -C ４０ Alkoxy, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C １ -C ４０ thioalkoxy, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C ２ -C ４０ alkenyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C ２ -C ４０ Alkynyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by Optionally, one or more substituents R ５ C substituted with ６ -C ６０ aryl, and Optionally, one or more substituents R ５ C substituted with ２ -C ５７ heteroaryl, R ５ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R ６ ) ２ , OR ６ , Si(R ６ ) ３ , B(OR ６ ) ２ , B(R ６ ) ２ , OSO ２ R ６ , C.F. ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C １ -C ４０ Alkoxy, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C １ -C ４０ thioalkoxy, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C ２ -C ４０ alkenyl, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C ２ -C ４０ Alkynyl, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by Optionally, one or more substituents R ６ C substituted with ６ -C ６０ aryl, and Optionally, one or more substituents R ６ C substituted with ２ -C ５７ heteroaryl, R ６ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh, CF ３ ,C.N.,F. C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, Optionally, one or more C １ -C ５ C substituted with alkyl substituents ６ -C １８ aryl, Optionally, one or more C １ -C ５ C substituted with alkyl substituents ２ -C １７ heteroaryl, N (C ６ -C １８ aryl) ２ , N (C ２ -C １７ Heteroaryl) ２ , and N (C ２ -C １７ Heteroaryl) (C ６ -C １８ aryl), where any substituent R ａ , R ｂ , R ５ and R ６ independently represents one or more substituents R ａ , R ｂ , R ５ and / or R ６ with the selective formation of mono- or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems.

2. The organic molecule of claim 1 , wherein the organic molecule comprises a structure of the following formula II-1 or II-2: 【Chemistry 2】 【change】

3. R ５ are, in each occurrence independently of one another, selected from the group consisting of: hydrogen, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, and N(Ph) ２ 。

4. R ５ are, in each occurrence independently of one another, selected from the group consisting of: hydrogen, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, and N(Ph) ２ 。

5. The organic molecule of claim 1 , wherein the organic molecule comprises the structure of Formula IIa-1: 【Chemistry 3】 Here, adjacent R ａ The substituents may independently form mono- or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems.

6. The organic molecule of claim 1, wherein the organic molecule comprises a structure of the following formula V-1, V-2, or V-3: 【Chemistry 4】 【change】 【change】

7. R ｂ are, in each occurrence independently of one another, selected from the group consisting of: hydrogen, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, and N(Ph) ２ 。

8. The organic molecule according to claim 1 is included as a unit, wherein each unit comprises or consists of a structure represented by Formula VI: 【Chemistry 5】 Here, m is an integer from 2 to 6.

9. 9. Use of an organic molecule according to any one of claims 1 to 8 as a light emitter in an optoelectronic device.

10. The use of claim 9, wherein the optoelectronic device is selected from the group consisting of: ・Organic light-emitting diode (OLED) ・Light-emitting electrochemical cells ・OLED sensor ・Organic diode ・Organic solar cells ・Organic transistor ・Organic field-effect transistor organic lasers, and - Down conversion element.

11. A composition comprising: (a) an organic molecule according to claim 1, in particular in emitter and / or host form; (b) an emitter material and / or a host material different from the organic molecule; and (c) optionally, a dye and / or a solvent.

12. 12. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 8 or a composition according to claim 11, in particular in the form of a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell, an OLED sensor, an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser and a down conversion device.

13. -substrate, -anode, a cathode, and - comprises a light-emitting layer, the anode or the cathode is disposed on the substrate; The optoelectronic device of claim 12 , wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or the composition.

14. 12. A method for producing an optoelectronic device, in which an organic molecule according to any one of claims 1 to 8 or a composition according to claim 11 is used.

15. 15. A method for manufacturing an optoelectronic device according to claim 14, comprising processing the organic molecules by a vacuum evaporation method or from a solution.

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