Organic molecules, compositions, photoelectronic devices, and methods for generating light

Abstract

The present invention relates to an organic molecule, in particular for application in optoelectronic devices. According to the invention, the organic molecule has the structure of the following formula I: [C98] JPEG2024517649000107.jpg7063 Chemical formula I Where: n, m, p, and q are integers selected from 0 and 1; where n+m=1 and p+q=1, Each r is an integer selected from 0, 1, 2, 3, or 4; Each s is an integer selected from 0, 1, 2, or 3; t is an integer selected from 0, 1, 2, 3, or 4; u is an integer selected from 1, 2, 3, 4, or 5; where t+u<=5, Z is a direct bond, CR 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3 , N.R. 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 are independently selected from the group consisting of R EWG , F, CF 3 , CN, substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 2 -C 57 Heteroaryl is selected from the group consisting of:

Description

[Technical Field]

[0001] This invention relates to organic light-emitting molecules, and to applications of light-emitting organic molecules in organic light-emitting diodes (OLEDs) and other optoelectronic devices. [Overview of the project] [Problems that the invention aims to solve]

[0002] The object of this invention is to provide a molecule 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 present invention, the organic molecule is a pure organic molecule, that is, unlike metal complexes known to be used in optoelectronic devices, it does not contain any metal ions. [Effects of the Invention]

[0005] According to the present invention, the organic molecules exhibit maximum emission in the blue or sky blue spectral range. The organic molecules exhibit maximum emission particularly from 420 nm to 580 nm, and especially from 440 nm to 560 nm. The photoluminescence quantum yield of the organic molecules according to the present invention is particularly 50% or more. The use of the molecules according to the present invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), results in higher efficiency of the device or higher color purity expressed by the full width at half maximum (FWHM) of the emission. The corresponding OLEDs have even higher stability than known emitter materials and OLEDs with equivalent hues. OLEDs having a light-emitting layer containing the organic molecules of the present invention together with a host material, particularly a host material in the form of a triplet-triplet annihilation material, have higher stability. [Modes for carrying out the invention]

[0006] The organic light-emitting molecule of the present invention contains or consists of the structure of the following Chemical Formula I:

Chemical formula

[0007] In one embodiment, R EWG It is selected from Group A, which consists of the following structure. [ka] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] Here, the dashed line represents a single bond connecting the substituent R EWG to an organic molecule as shown in Chemical Formula I, and here, optionally, two or more adjacent substituents R 5 can independently form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system, where one or more hydrogen atoms of the optionally formed ring system are also substituted by R 6 .

[0008] In one embodiment, the organic molecule comprises or consists of the structure of the following Chemical Formula IIa, Chemical Formula IIb or Chemical Formula IIc. [Chemistry] Chemical Formula IIa [Chemistry] Chemical formula IIb

Chem.

[0009] In one embodiment, Z is each a direct bond, NR 3 , O, or S, respectively, selected from.

[0010] CIn one embodiment, Z is each a direct bond.

[0011] In one embodiment, the organic molecule contains or consists of the structure of the following chemical formula IIIa, chemical formula IIIb, chemical formula IIIc, or chemical formula IIId:

Chem.

Chem.

Chem.

Chem.

[0012] In one embodiment, the organic molecule contains or consists of the following chemical formula IVa or chemical formula IVb.

Chem.

[0013] In one embodiment, R a Each of them is independently selected from the following groups: hydrogen, deuterium, Me, i Pr, t Bu, CN Sofa CF3, Me, i Pr, t Ph is selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Pyridinyl molecules selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Pyrimidinyl molecules selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Carbazolyl, selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Triazinyls selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and Me, i Pr, t N(Ph)2 is selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Here, two or more adjacent substituents R a It can form attachment points for ring systems selected from the group consisting of the following: [ka] Here, each dashed line represents the condensation of the ring systems of the aforementioned group into the structure shown in chemical formula I, with one of the aforementioned ring systems being connected to two adjacent substituents R. a This indicates a direct connection to the position indicated.

[0014] In one embodiment, R a Each of these is independently selected from the following group: hydrogen, deuterium, Me, i Pr, t Bu, CN Sofa CF3, Me, i Pr, t Ph is selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Pyridinyl molecules selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Pyrimidinyl molecules selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Carbazolyl, selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Triazinyls selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and Me, i Pr, t N(Ph)2 is selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0015] In one embodiment, the organic molecule includes or comprises the structure of the following chemical formulas Va, Vb, or Vc. [ka] Chemical formula Va [ka] Chemical formula Vb [ka] Chemical formula Vc Here, w are integers that are either 0 or 1, independently of each other. R b Each of these is independently selected from the following group: Hydrogen, deuterium, N(R) 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 CF3, CN, F, Br, I, C1-C 40 Alkyl, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C2-C 40 Alkinil, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively R 5C=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, SO2, NR 5 , O, S or CONR 5 Replaced by, Selectively one or more substituents R 5 C6-C replaced by 60 Aryl, and Selectively one or more substituents R 5 C2-C replaced by 57 Heteroaryl.

[0016] In one embodiment, R 6 Each of them independently consists of hydrogen (H), methyl (Me), and i-propyl (CH(CH3)2)( i Pr), t-butyl ( t Selected from the group consisting of Bu), phenyl (Ph), CN, CF3, and diphenylamine (NPh2).

[0017] In one embodiment, R 5 Each of them independently consists of hydrogen (H), methyl (Me), and i-propyl (CH(CH3)2)( i Pr), t-butyl ( t Selected from the group consisting of Bu), phenyl (Ph), CN, CF3, and diphenylamine (NPh2).

[0018] In one embodiment of the present invention, R a Each of these is independently selected from the following group: Hydrogen, deuterium, Me, i Pr, t Bu, CN Sofa CF3, Me, i Pr, tPh is selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Pyridinyl molecules selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Pyrimidinyl molecules selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Carbazolyl, selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph. Me, i Pr, t Triazinyls selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and N(Ph)2.

[0019] In one embodiment, at least one monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-condensed ring system is substituted with R a , R 3 , R 4 , R 5 and R 6 Along with one or more further substituents R a , R 3 , R 4 , R 5 and / or R 6 It is formed by.

[0020] In one embodiment, R I , R II and R III The following group is selected: Hydrogen, deuterium, Me, i Pr, t Bu, Me, i Pr, tPh is selectively substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0021] In one embodiment, R II and R III At least one substituent selected from is hydrogen.

[0022] In one embodiment, R II and R III At least one substituent selected from is not hydrogen.

[0023] In a preferred embodiment, R II It is hydrogen.

[0024] In a preferred embodiment, R III It is not hydrogen.

[0025] In a preferred embodiment, R II is hydrogen, and R III It is not hydrogen.

[0026] In one embodiment, R I It is hydrogen.

[0027] definition Here, the term "layer" refers to an object having a wide-ranging planar geometric structure. The fact that optoelectronic elements are composed of multiple layers forms part of common knowledge for those skilled in the art.

[0028] In the context of the present invention, an EML is a layer of a photoelectronic device, where light emission from the layer is observed when a voltage and current are applied to the device. Those skilled in the art will understand that light emission from a photoelectronic device is attributable to light emission from at least one EML. Those skilled in the art will understand that light emission from an EML is not typically attributable to all materials contained in the EML, but rather to a specific emitter material.

[0029] In the context of the present invention, the “emitter material” (also referred to as the “emitter”) is a material that emits light when contained in the light-emitting layer (EML) of a photoelectronic device under given voltage and current conditions (see below). Those skilled in the art will know that the emitter material is generally a “luminescent dopant” material, and that the dopant material (whether luminescent or not) is typically a material incorporated into a matrix material called a host material (as used herein). Here, the host material is generally H when contained in a photoelectronic device, preferably an OLED, that contains at least one organic molecule according to the present invention. B It is called that.

[0030] In the context of the present invention, the term "cyclic group" may be understood in its broadest sense as any monocyclic, bicyclic, or polycyclic moiety.

[0031] In the context of the present invention, when referring to a chemical structure, the term "ring" may be understood in its broadest sense as any monocyclic moiety. From the same viewpoint, when referring to a chemical structure, the term "ring" may be understood in its broadest sense as any bicyclic or polycyclic moiety.

[0032] In the context of the present invention, the term "ring system" may be understood in its broadest sense as any monocyclic, bicyclic, or polycyclic moiety.

[0033] In the context of this invention, the term "ring atom" refers to any atom that is part of a cyclic core of a ring or ring system and is not part of an acyclic substituent selectively bonded to the cyclic core.

[0034] In the context of the present invention, the term "carbocyclic" may be understood in its broadest sense as any cyclic group whose cyclic core structure consists only of carbon atoms that can be substituted with hydrogen, or any other substituents as defined in particular embodiments of the present invention. The term "carbocyclic" may be understood as an adjective referring to a cyclic group whose cyclic core structure consists only of carbon atoms that can be substituted with hydrogen, or any other substituents as defined in particular embodiments of the present invention.

[0035] In the context of the present invention, the term “heterocyclic” may be understood in its broadest sense as any cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The term “heterocyclic” may be understood as an adjective referring to a cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. Unless otherwise specifically mentioned in a particular embodiment, the heteroatoms may be identical or different and may be individually selected from the group consisting of B, Si, N, O, S, and Se, more preferably B, N, O, and S, and most preferably N, O, and S. Not to mention all carbon atoms or heteroatoms included in a heterocyclic in the context of the present invention, they may be substituted with hydrogen or any other substituent as defined in a particular embodiment of the present invention.

[0036] Those skilled in the art will understand that any cyclic group (i.e., any carbon ring and heteroring) can be aliphatic, aromatic, or heteroaromatic.

[0037] In the context of the present invention, when referring to a cyclic group (i.e., one ring, multiple rings, cyclic system, carbocyclic, heterocyclic), the term “aliphatic” means a cyclic core structure (excluding selectively attached substituents) that includes at least one ring atom that is not part of an aromatic or heteroaromatic ring or cyclic system. Preferably, most of the ring atoms, more preferably all, within the aliphatic cyclic group are not part of an aromatic or heteroaromatic ring or cyclic system (e.g., cyclohexane or piperidine). Herein, when referring to an aliphatic ring or cyclic system in general, no distinction is made between carbocyclic and heterocyclic groups, and the term “aliphatic” is also used as an adjective to describe a carbocyclic or heterocyclic to indicate whether or not a heteroatom is included within the aliphatic cyclic group.

[0038] As will be understood by those skilled in the art, the terms “aryl” and “aromatic” may be understood in their broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moisture, i.e., a ring group in which all ring atoms are part of an aromatic ring system, preferably as part of the same aromatic ring system. However, throughout this application, the terms “aryl” and “aromatic” are limited to monocyclic, bicyclic, or polycyclic aromatic moisture in which all aromatic ring atoms are carbon atoms. In contrast, in this application, the terms “heteroaryl” and “heteroaromatic” refer to any monocyclic, bicyclic, or polycyclic aromatic moisture in which at least one aromatic carbocyclic atom is substituted by a heteroatom (i.e., not carbon). Unless otherwise specifically mentioned in a particular embodiment of the present invention, at least one heteroatom in a "heteroaryl" or "heteroaromatic" group may be the same or different, and may be individually selected from the group consisting of N, O, S, and Se, more preferably N, O, and S. Those skilled in the art will understand that the adjectives "aromatic" and "heteroaromatic" are also used to describe any cyclic group (i.e., any ring system). That is, an aromatic cyclic group (i.e., an aromatic ring system) is an aryl group, and a heteroaromatic cyclic group (i.e., a heteroaromatic ring system) is a heteroaryl group.

[0039] Unless otherwise specifically mentioned in a particular embodiment of the present invention, in this application, an aryl group preferably comprises 6 to 60 aromatic ring atoms, more preferably 6 to 40 aromatic ring atoms, and even more preferably 6 to 18 aromatic ring atoms. Unless otherwise specifically mentioned in a particular embodiment of the present invention, in this application, a heteroaryl group preferably comprises 5 to 60 aromatic ring atoms, more preferably 5 to 40 aromatic ring atoms, and even more preferably 5 to 20 aromatic ring atoms, of which at least one is a heteroatom, preferably selected from N, O, S, and Se, and more preferably from N, O, and S. If one or more heteroatoms are included in the heteroaromatic group, all heteroatoms are preferably selected independently from each other from N, O, S, and Se, and more preferably from N, O, and S.

[0040] In the context of the present invention, for both aromatic groups and heteroaromatic groups (e.g., aryl substituents or heteroaryl substituents), the number of aromatic ring carbon atoms is a subscript in the definition of a particular substituent, for example, "C6-C 60 The form is given as "aryl". This means that each aryl substituent contains 6 to 60 aromatic carbon ring atoms. The same subscript is used to indicate the number of carbon atoms allowed for all other types of substituents, whether aliphatic, aromatic, or heteroaromatic. For example, "C1-C 40 The term "alkyl" refers to an alkyl substituent containing 1 to 40 carbon atoms.

[0041] Preferred examples of aryl groups include benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluorantene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, or groups derived from combinations thereof.

[0042] Preferred examples of heteroaryl groups include furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenantholidine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, This includes phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarbolin, 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, 1,2,4,5-tetrazine, purine, pteridine, indidine, and benzothiadiazole, or groups derived from combinations thereof.

[0043] As used throughout this specification, the term “arylene” refers to a divalent aryl substituent that has two binding sites to other molecular structures and acts as a linker structure. From the same viewpoint, the term “heteroarylene” refers to a divalent aryl substituent that has two binding sites to other molecular structures and acts as a linker structure.

[0044] In the context of the present invention, when referring to an aromatic ring system or a heteroaromatic ring system, the term “condensed” means that the “condensed” aromatic ring or heteroaromatic ring shares 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 condensed 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. Also, in such context, sharing a bond can be understood as including sharing two atoms that make up each bond, and a condensed aromatic ring system or heteroaromatic ring system may be understood as one aromatic system or heteroaromatic system. Alternatively, one or more bonds may be shared by the aromatic rings or heteroaromatic rings that make up a condensed aromatic ring system or heteroaromatic ring system (e.g., pyrene). Furthermore, aliphatic ring systems can also be condensed, and this may be understood as having the same meaning as aromatic ring systems or heteroaromatic ring systems, except that the condensed aliphatic ring system is not aromatic. Also, aromatic ring systems or heteroaromatic ring systems can be condensed with aliphatic ring systems (i.e., share at least one bond).

[0045] In the context of this invention, the term "condensed" ring system has the same meaning as "fused" ring system.

[0046] In certain embodiments of the present invention, adjacent substituents bonded to a ring or ring system may form further monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring systems condensed onto the aromatic or heteroaromatic ring or ring system to which the substituents are bonded. A condensed ring system selectively formed in this manner may be understood to be larger (meaning containing more ring atoms) than the aromatic or heteroaromatic ring or ring system to which the adjacent substituents are bonded. In that case (and where such figures are provided), the "total" number of ring atoms contained in the condensed ring system should be understood as the sum of the ring atoms contained in the aromatic or heteroaromatic ring or ring system. Adjacent substituents are bonded, and the ring atoms of the additional ring system are formed by the adjacent substituents, but ring atoms shared by the condensed ring are counted once, not twice. For example, a benzene ring may have two adjacent substituents that form yet another benzene ring so that a naphthalene core is formed. The naphthalene core will contain 10 ring atoms, since two carbon atoms are shared by two benzene rings and are counted only once, not twice.

[0047] Generally, in the context of the present invention, the terms “adjacent substituent” or “adjacent group” mean a substituent or group bonded to the same or adjacent atom.

[0048] In the context of the present invention, the term "alkyl group" may be understood in its broadest sense as any linear, branched, or cyclic alkyl substituent. Preferred examples of alkyl groups as substituents are methyl (Me), ethyl (Et), n-propyl ( n Pr), i-propyl( i Pr), cyclopropyl, n-butyl ( n Bu), i-butyl ( i Bu), s-butyl ( s Bu), t-butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl Syl, 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, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-octo-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-hexadequi-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-octo-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl This includes 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadequi-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.

[0049] For example, in s-butyl, s-pentyl, and s-hexyl, "s" means "secondary," that is, s-butyl, s-pentyl, and s-hexyl are identical to sec-butyl, sec-pentyl, and sec-hexyl, respectively. For example, in t-butyl, t-pentyl, and t-hexyl, "t" means "tertiary," that is, t-butyl, t-pentyl, and t-hexyl are identical to tert-butyl, tert-pentyl, and tert-hexyl, respectively.

[0050] As used herein, the term “alkenyl” includes linear, branched, and cyclic alkenyl substituents. The term “alkenyl group” includes, for example, substituents such as ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0051] As used herein, the term “alkynyl” includes linear, branched, and cyclic alkynyl substituents. The term “alkynyl group” includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octinyl.

[0052] As used herein, the term “alkoxy” includes linear, branched, and cyclic alkoxy substituents. The term “alkoxy group” includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.

[0053] As used herein, the term “thioalkoxy” includes linear, branched, and cyclic thioalkoxy substituents, where the oxygen atom O of the corresponding alkoxy group is replaced by sulfur S.

[0054] As used herein, the term “halogen” (or, in chemical nomenclature, “halo” when referring to a substituent) may be understood in its broadest sense to be any atom of the elements of the seventh major group (i.e., Group 17) of the periodic table, preferably fluorine, chlorine, bromine, or iodine.

[0055] When a molecular fragment is described as being bound to a substituent or another molecule, its name may be described as if it were the fragment itself (e.g., naphthyl, dibenzofuryl) or as the entire molecule (e.g., naphthalene, dibenzofuran). The manners used herein to describe substituents or bound fragments are considered equivalent.

[0056] Furthermore, in this application, "C6-C 60 "Aryl" or "C1-C" 40 Whenever a substituent like "alkyl" is mentioned without specifying the bonding site within that substituent, it means that each substituent is bonded via any atom. For example, "C6-C 60 The "aryl" substituent is bonded via any 6 to 60 aromatic carbon atoms, and is "C1-C 40 Alkyl substituents are bonded via any 1 to 40 aliphatic carbon atoms. On the other hand, 2-cyanophenyl substituents are bonded only in a manner that their CN group is adjacent to the bonding site, in order to allow for precise chemical nomenclature.

[0057] In the context of this invention, whenever a substituent such as “butyl,” “biphenyl,” or “terphenyl” is mentioned without further detail, this means that any isomorph of each substituent is acceptable as a particular substituent. In this regard, for example, the term “butyl” as a substituent includes n-butyl, s-butyl, t-butyl, and isobutyl as substituents. Similarly, the term “biphenyl” as a substituent includes ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined with respect to the binding site of the biphenyl substituent to each chemical molecule having the biphenyl substituent. Similarly, as substituents, the term "terphenyl" includes 3-ortho-terphenyl, 4-ortho-terphenyl, 4-meta-terphenyl, 5-meta-terphenyl, 2-para-terphenyl, or 3-para-terphenyl, where, as is known to those skilled in the art, ortho, meta, and para indicate the positions of two Ph moieties within the terphenyl group relative to each other, and "2-", "3-", "4-", and "5-" indicate the bonding positions of the terphenyl substituent to the respective chemical molecule having the terphenyl substituent.

[0058] All defined groups and indeed all chemical moieties, whether cyclic or acyclic, aliphatic, aromatic or heteroaromatic, are understood to be further substituted by the specific embodiments described herein.

[0059] All hydrogen atoms (H) in any structure referred to in this application are also substituted with deuterium (D) independently of each other, unless otherwise specified. Substituting hydrogen with deuterium is common practice and is obvious to those skilled in the art. There are therefore many well-known methods and some review articles that can achieve this.

[0060] When comparing experimental or computational data, the values ​​must be determined using the same methodology. For example, experimental ΔE obtained by a specific method STIf the energy is determined to be less than 0.4 eV, the comparison is only valid if the same identification method is used, including the same conditions. For example, a comparison of the photoluminescence quantum yield (PLQY) of different compounds is only valid if the PLQY determination is performed under the same reaction conditions (e.g., room temperature, measurement on a 10% PMMA film). Similarly, the calculated energy values ​​must be determined by the same calculation method (along with the same function and the same base set).

[0061] Photoelectronic device comprising at least one organic molecule according to the present invention A further aspect of the present invention relates to a photoelectronic device comprising at least one organic molecule according to the present invention.

[0062] In one embodiment, a photoelectronic device comprising at least one organic molecule according to the present invention is selected from the group consisting of the following: • Organic light-emitting diode (OLED) • Light-emitting electrochemical cell • OLED sensors, particularly gas and vapor sensors that are not completely isolated from the outside. • Organic diode ·Organic solar cells • Organic transistors • Organic field-effect transistor • Organic laser • Down-conversion element.

[0063] The light-emitting electrochemical cell consists of three layers: a cathode, an anode, and an active layer containing the organic molecule according to the present invention.

[0064] In a preferred embodiment, the photoelectronic device comprising at least one organic molecule according to the present invention is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), organic lasers, and light-emitting transistors.

[0065] In a more preferred embodiment, the photoelectronic device comprising at least one organic molecule according to the present invention is an organic light-emitting diode (OLED).

[0066] In one embodiment, the photoelectronic device comprising at least one organic molecule according to the present invention is an OLED having the following layer structure, 1. Circuit board 2. Anode layer A 3. Hole Injection Layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (also called emission layer) (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer C Here, the OLED selectively includes each of the layers except for the anode layer A, cathode layer C, and light-emitting layer EML, and different layers are merged, and the OLED may include one or more layers from each of the layer types defined above.

[0067] Furthermore, the photoelectronic element comprising at least one organic molecule according to the present invention may selectively include one or more protective layers to protect the element from damage exposure to harmful substances in the environment, such as moisture, vapor, and / or gas.

[0068] In one embodiment, the photoelectronic device comprising at least one organic molecule according to the present invention is an OLED having the following inverted layer structure, 1. Circuit board 2. Cathode layer C 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Emitting layer (also called emission layer) (EML) 7.Electron blocking layer (EBL) 8. Hole Transport Layer (HTL) 9. Hole Injection Layer (HIL) 10. Anode layer A Here, an OLED (having an inverted layer structure) selectively includes each of the layers except for the anode layer A, cathode layer C, and light-emitting layer EML, and different layers are merged, and the OLED may include one or more layers from each of the layer types defined above.

[0069] The organic molecules according to the present invention (as described in the embodiments above) can be used in various layers by specific structures and substitutions. When used, the fraction of the organic molecules according to the present invention in each layer of a photoelectronic device, particularly an OLED, is 0.1% to 99% by weight, more preferably 1% to 80% by weight. In an alternative embodiment, the proportion of the organic molecules in each layer is 100% by weight.

[0070] In one embodiment, a photoelectronic device comprising at least one organic molecule according to the present invention is an OLED that may have a stacked structure. In this structure, unlike the general arrangement in which OLEDs are arranged side by side, individual units are stacked on top of each other. Mixed light is produced by OLEDs exhibiting a stacked structure, and in particular, white light is produced by stacking blue OLEDs, green OLEDs, and red OLEDs. Furthermore, OLEDs exhibiting a stacked structure may selectively include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally composed of an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0071] In one embodiment, a photoelectronic device comprising at least one organic molecule according to the present invention is an OLED comprising two or more light-emitting layers between an anode and a cathode. In particular, a so-called tandem OLED comprises 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 additional layers such as charge generation layers, charge blocking layers, or charge transport layers may be selectively included between the individual light-emitting layers. In a further embodiment, the light-emitting layers are stacked adjacent to each other. In a further embodiment, the tandem OLED includes a charge generation layer between each of the two light-emitting layers. Alternatively, adjacent light-emitting layers, or light-emitting layers separated by a charge generation layer, may be merged.

[0072] In one embodiment, a photoelectronic device comprising at least one organic molecule according to the present invention is also essentially a white photoelectronic device, meaning that the device emits white light. For example, such a white photoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and / or red light. Furthermore, there may be selective energy transfer between two or more molecules, as described in later sections of this text (see below).

[0073] In the case of a photoelectronic device containing at least one organic molecule according to the present invention, at least one organic molecule according to the present invention is contained in the light-emitting layer (EML) of the photoelectronic device, most preferably the EML of an OLED. However, the organic molecule according to the present invention is also used, for example, in an electron transport layer (ETL) and / or electron blocking layer (EBL) or an exciton blocking layer and / or hole transport layer (HTL) and / or hole blocking layer (HBL). When used, the fraction of the organic molecule according to the present invention in each layer of the photoelectronic device, particularly an OLED, is 0.1% to 99% by weight, more preferably 0.5% to 80% by weight, and particularly 0.5% to 10% by weight. In an alternative embodiment, the proportion of the organic molecule in each layer is 100% by weight.

[0074] The criteria for selecting materials suitable for individual layers of optoelectronic devices, particularly OLEDs, are common knowledge to those skilled in the art. The latest technology has demonstrated many materials for use in individual layers, indicating which materials are suitable for use together. It is understood that any material used in the industry can also be used in optoelectronic devices containing organic molecules according to the present invention. Below are preferred examples of materials for individual layers. It is understood that this does not mean that all types of layers listed below must be present in the optoelectronic device containing at least one organic molecule according to the present invention. Furthermore, it is understood that the optoelectronic device containing at least one organic molecule according to the present invention includes one or more of the layers listed below, such as two or more light-emitting layers (EMLs). It may also be understood that two or more layers of the same type (e.g., two or more EMLs, or two or more HTLs) do not necessarily contain the same material, or even the same proportion of the same material. Also, the optoelectronic device containing at least one organic molecule according to the present invention does not need to contain all types of layers listed below, where the anode layer, cathode layer, and light-emitting layer are generally present in all cases.

[0075] The substrate may be formed from any material or composition of materials. Most often, 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 plastic slide may be used. This can allow for an even higher level of flexibility. The anode layer A is composed of a material from which a nearly (essentially) transparent film can be obtained. Since at least one of the two electrodes must be (essentially) transparent in order to allow light emission from the OLED, one of the anode layer A or cathode layer C is transparent. Preferably, the anode layer A contains or consists of a large amount of transparent conductive oxides (TCOs). Such an anode layer A may contain, for example, indium tin oxide, aluminum zinc oxide, fluorine-doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped SI, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene.

[0076] Preferably, the anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1The anode layer A is composed of ). The roughness of the anode layer A due to the transparent conductive oxide (TCO) may also be mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of pseudocharge carriers (i.e., holes) from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) may contain poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonic acid (PSS), MoO2, V2O5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent the diffusion of metal from the anode layer A to the hole transport layer (HTL). For example, HIL is PEDOT:PSS (poly-3,4-ethylenedioxythiophene:polystyrene sulfonic acid), PEDOT (poly-3,4-ethylenedioxythiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'-nis-(1 It may also consist of (-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonnitrile) and / or Spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0077] Adjacent to the anode layer A or hole injection layer (HIL), generally, a hole transport layer (HTL) is located. Here, any hole transport compound can be used. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles may be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the luminescence layer (EML). The hole transport layer (HTL) is also an electron blocking layer (EBL). Preferably, the hole transport compound has a lowest excited triplet state T1 at a relatively high energy level. For example, the hole transport layer (HTL) includes tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenylamine)), α-NPD (poly(4-butylphenyl-diphenylamine)), TAPC (4,4'-cyclohexyllidene-bis[N,N-bis(4-methylphenyl)benzeneamine]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)-amino]triphenylamine), Spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'- The HTL may also contain star-shaped heterocycles such as nis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine, NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonnitrile) and / or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9'H-3,3'-bicarbazole). The HTL may also contain a p-doped layer composed of inorganic or organic dopants within the organic hole transport matrix.As inorganic dopants, transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide may be used. As organic dopants, for example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoic acid (Cu(I)pFBz), or transition metal complexes may be used.

[0078] EBL may include, for example, mCP (1,3-bis(carbazole-9-yl)benzene), TCTA (tris(4-carbazoyl-9-ylphenyl)amine), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine), mCBP (3,3-di(9H-carbazole-9-yl)biphenyl), tris-Pcz (9-phenyl-3,6-bis(9-phenyl-9H-carbazole-3-yl)-9H-carbazole), CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) and / or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).

[0079] Generally, the emissive layer (EML) is located adjacent to the hole transport layer (HTL) or (if present) the electron blocking layer (EBL). The emissive layer (EML) contains at least one emissive molecule (i.e., emitter material). Generally, the EML further contains one or more host materials (also called matrix materials). For example, the host materials are CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), mCBP (3,3-di(9H-carbazole-9-yl)biphenyl), Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), Sif88 (dibenzo[b,d]thiophene-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole Selected from ruvasol, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), and / or TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine). As is known to those skilled in the art, the host material must generally be selected to exhibit a first (i.e., lowest) excited triplet state (T1) and a first (i.e., lowest) excited singlet state (S1) energy level, which is higher in energy than the first (i.e., lowest) excited triplet state (T1) and first (i.e., lowest) excited singlet state (S1) energy levels of at least one luminescent molecule incorporated into the respective host material.

[0080] As described above, in the context of the present invention, it is preferable that at least one EML of the photoelectronic device contains at least one molecule according to the present invention. Preferred compositions of EMLs of photoelectronic devices containing at least one organic molecule according to the present invention will be described in more detail in later sections of this text (see below).

[0081] An electron transport layer (ETL) may be located adjacent to the light-emitting layer (EML). Here, any electron transporter may be used. Exemplary examples include electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)phenyl (TPBi). ETL may include, for example, NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenylphosphine oxide), BPyTP2 (2,7-di(2,2'-bipyridine-5-yl)triphenyl), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene) and / or BTB (4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Selectively, the ETL may be doped with a material such as Liq(8-hydroxyquinolinolatritium). The electron transport layer (ETL) may also block holes. Alternatively, a hole blocking layer (HBL) is generally introduced between the EML and the ETL.

[0082] Hole blocking layers (HBLs) include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = basocuproin), 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 9,9'-(5-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidine-4-yl)-1,3-phenylene)bis(9H-carbazole), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline). It may also contain phosphorus, Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenylphosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazol)benzol / 1,3,5-tris(carbazole)-9-yl)benzene).

[0083] Adjacent to the electron transport layer (ETL), the cathode layer C may be located. The cathode layer C may contain or consist of, for example, 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 consist of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively or additionally, the cathode layer C may also contain graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also contain or consist of nanoscale silver wire.

[0084] An OLED comprising at least one organic molecule according to the present invention may optionally further include a protective layer (also referred to as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The EIL layer may contain lithium fluoride, cesium fluoride, silver, Liq(8-hydroxyquinolinolatritium), Li2O, BaF2, MgO and / or NaF.

[0085] Selectively, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also contain one or more host compounds.

[0086] As used herein, unless otherwise specifically defined in a particular context, the hue designation of emitted and / or absorbed light is as follows: Purple: Wavelength range of >380~420nm Deep blue: Wavelength range >420~480nm Sky blue: Wavelength range of >480~500nm Green: Wavelength range >500~560nm Yellow: Wavelength range >560~580nm Orange: Wavelength range >580~620nm Red: Wavelength range of >620~800nm.

[0087] With respect to the emitter molecule (i.e., the emitter material), such a hue indicates the maximum emission of the main emission peak. Therefore, for example, a deep blue emitter has maximum emission in the >420-480 nm range, a sky blue emitter has maximum emission in the >480-500 nm range, a green emitter has maximum emission in the >500-560 nm range, and a red emitter has maximum emission in the >620-800 nm range.

[0088] The deep blue emitter may preferably have a maximum emission of less than 475 nm, more preferably less than 470 nm, even more preferably less than 465 nm, or even less than 460 nm. It is generally 420 nm or higher, preferably 430 nm or higher, more preferably 440 nm or higher, or even more preferably 450 nm or higher. In a preferred embodiment, the organic molecule according to the present invention exhibits maximum emission at 420 to 500 nm, preferably 430 to 490 nm, more preferably 440 to 480 nm, and most preferably 450 to 470 nm, and is generally measured at room temperature (i.e., about 20°C) from a spin-coated film containing 1 to 5% by weight, preferably 2% by weight, of the organic molecule according to the present invention in poly(methyl methacrylate), PMMA, or mCBP, or alternatively, from 0.001 mg / mL of the organic molecule according to the present invention in an organic solvent, preferably DCM or toluene.

[0089] Further embodiments relate to an OLED comprising at least one organic molecule according to the present invention, which emits light having CIEx and CIEy color coordinates close to the color coordinates of primary blue (CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, such as UHD-TVs. Therefore, a further aspect of the present invention relates to an OLED comprising at least one organic molecule according to the present invention, wherein the luminescence exhibits CIEx color coordinates of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, even more preferably 0.08 to 0.18, or more preferably 0.10 to 0.15, and / or CIEy color coordinates of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, even more preferably 0.03 to 0.15, or more preferably 0.04 to 0.10.

[0090] Further embodiments include at least one organic molecule according to the present invention, and have a concentration of 1000 cd / m². 2 In this configuration, the external quantum efficiency is greater than 8%, preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even more preferably greater than 20%, and / or the maximum emission is at 420 to 500 nm, preferably greater than 430 to 490 nm, more preferably greater than 440 to 480 nm, most preferably greater than 450 to 470 nm, and / or 500 cd / m². 2 This invention relates to OLEDs exhibiting an LT80 value of 100h or more, preferably 200h or more, more preferably 400h or more, even more preferably 750h or more, or even more preferably 1000h or more.

[0091] The green emitter material can preferably have a maximum emission of 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm.

[0092] Further preferred embodiments relate to an OLED comprising at least one organic molecule according to the present invention and emitting light at distinct color points. Preferably, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In a preferred embodiment, the OLED comprising at least one organic molecule according to the present invention emits light having 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 0.1 eV, or less than 0.17 eV.

[0093] According to the present invention, a photoelectronic element comprising at least one organic molecule according to the present invention can be used, for example, as a light source in the field of displays, lighting applications, and medical and / or cosmetic applications (e.g., phototherapy).

[0094] Combination of organic molecules and additional materials according to the present invention The fact that any layer within a photoelectronic device (preferably an OLED), particularly an emissive layer (EML), consists of a single material or a combination of different materials, is part of the general knowledge of those skilled in the art.

[0095] For example, a person skilled in the art will understand that an EML is composed of a single material that emits light when a voltage (and current) is applied to the element. However, a person skilled in the art will understand that in an EML of a photoelectronic element (wherein preferably an OLED), different materials, in particular one or more host materials (i.e., matrix materials; wherein a photoelectronic element comprising at least one organic molecule according to the present invention, the host material H B It is understood that when voltage and current are applied to the element, coupling with one or more dopant materials (i.e., emitter materials) that emit light at least one of them is advantageous.

[0096] In a preferred embodiment of the use of the organic molecule according to the present invention in a photoelectronic device, the photoelectronic device includes at least one organic molecule according to the present invention in an EML, a layer directly adjacent to the EML, or one or more layers of those layers.

[0097] In a preferred embodiment of the use of the organic molecule according to the present invention in a photoelectronic device, the photoelectronic device is an OLED and contains at least one organic molecule according to the present invention in an EML, a layer directly adjacent to the EML, or one or more layers of those layers.

[0098] In a more preferred embodiment of the use of organic molecules according to the present invention in photoelectronic devices, the photoelectronic device is an OLED, and the EML contains at least one organic molecule according to the present invention.

[0099] In one embodiment relating to a photoelectronic device, preferably an OLED, comprising at least one organic molecule according to the present invention, at least one, preferably each organic molecule according to the present invention, is used as an emitter material in a light-emitting layer (EML), which emits light when a voltage (and current) is applied to the device.

[0100] As is known to those skilled in the art, for example, in an organic light-emitting diode (OLED), the emission from the emitter material (i.e., the luminescent dopant) includes fluorescence from an excited singlet state (generally the lowest excited singlet state S1) and phosphorescence from an excited triplet state (generally the lowest excited triplet state T1).

[0101] A fluorescent emitter F can emit light at room temperature (i.e., about 20°C) when electronically excited (e.g., in a photoelectronic device), and the luminescent excited state is a singlet state. Fluorescent emitters generally exhibit immediate (i.e., direct) fluorescence on a nanosecond timescale when the initial electronic excitation (e.g., by electron-hole recombination) provides the excited singlet state of the emitter.

[0102] In the context of the present invention, a delayed fluorescence material is a material that can reach an excited singlet state (generally the lowest excited singlet state S1) from an excited triplet state (generally the lowest excited singlet state S1) via reverse intersystem crossing (RISC; i.e., up-system crossing or reverse intersystem crossing), and can emit light when returning from the excited singlet state (generally S1) to the electronic ground state. The timescale (generally in the microsecond range) at which fluorescence emission occurs after RISC from the excited triplet state (generally T1) to the excited singlet state (generally S1) occurs is slower than the timescale (generally in the nanosecond range) at which direct (i.e., immediate) fluorescence occurs, and is therefore called delayed fluorescence (DF). When RISC from the excited triplet state (generally from T1) to the excited singlet state (generally up to S1) occurs via thermal activation, and the thus filled excited singlet state emits light (delayed fluorescence emission), the process is called thermally activated delayed fluorescence (TADF). Therefore, TADF materials are materials that can emit thermally activated delayed fluorescence (TADF) as described above. The lowest excited singlet state energy level E(S1) of the fluorescent emitter F E ) and the lowest excited triplet state energy level E(T1 E ) Energy difference ΔE STThose skilled in the art know that if ΔE decreases, the RISC-mediated switching from the lowest excited singlet state to the lowest excited triplet state occurs with high efficiency. Therefore, TADF materials generally have a small ΔE. ST Having a value forms part of the general knowledge of those skilled in the art (see below). As is known to those skilled in the art, TADF materials are not simply materials capable of their own RISC from an excited triplet state to an excited singlet state, along with the subsequent emission of TADF as described above. TADF materials consist of virtually two types of materials, preferably two host materials H B More preferably, p-host material H P and n-host material H N Those skilled in the art know that it is an exciplex formed from (see below).

[0103] The generation of (thermally activated) delayed fluorescence is analyzed based on decay curves obtained, for example, from time-resolved (i.e., transient) photoluminescence (PL) measurements. For this purpose, spin-coated films of 1–10 wt%, particularly 10 wt%, of each emitter (i.e., assumed TADF material) in poly(methyl methacrylate) (PMMA) are used as samples. The analysis is performed, for example, using an Edinburgh Instruments FS5 fluorescence spectrometer. A nitrogen atmosphere is maintained while the sample PMMA film is placed in a cuvette for measurement. Data acquisition is performed using the well-established time-correlated single-photon counting (TCSPC, see below) technique. To collect the overall decay dynamics over multiple orders of magnitude in time and signal intensity, measurements can be performed and coupled in four time domains (200 ns, 1 μs, 20 μs, and longer measurement periods >80 μs) (see below).

[0104] The TADF material preferably satisfies the following two conditions in relation to the overall damping mechanics described above: (i) Damping dynamics exhibit two time domains, one in the nanosecond (ns) range and the other in the microsecond (μs) range, and (ii) The morphology of the emission spectrum is identical in the two time domains.

[0105] Here, some of the light emitted in the first decay region is taken as immediate fluorescence, and some of the light emitted in the second decay region is taken as delayed fluorescence.

[0106] The ratio of delayed fluorescence to immediate fluorescence is expressed in the form of a so-called n-value, which is calculated by integrating the respective photoluminescence decays over time using the following equation:

number

[0107] In a preferred embodiment, the organic molecule according to the present invention exhibits an n value greater than 0.05 (n>0.05) (ratio of delayed fluorescence to immediate fluorescence).

[0108] In the context of the present invention, TADF material E B This is the lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ΔE corresponds to the energy difference with ) ST It 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 more preferably less than 0.05 eV. TADF material E B ΔE ST The method for determining the value is explained in a later section of this text.

[0109] One common approach to designing TADF materials is to covalently bond one or more (electron) donor mosies containing HOMOs and one or more (electron) acceptor mosies containing LUMOs to the same bridge, which is referred to in this application as a linker group. B For example, it includes two or three linker groups bonded to the same acceptor moiety, and further donor moieties and acceptor moieties may be bonded to each of those two or three linker groups.

[0110] Furthermore, one or more donor moieties and one or more acceptor moieties can be directly bonded to each other (without the presence of a linker group).

[0111] Typical donor moieties are diphenylamines, indoles, carbazoles, acridines, phenoxazines, and derivatives of related structures. In particular, aliphatic, aromatic, or heteroaromatic ring systems are condensed into the aforementioned donor precursors to reach, for example, indolocarbazole.

[0112] Benzene, biphenyl, and to some extent, derivatives of terphenyl are common linker groups.

[0113] Nitrile groups are very common acceptor moieties in TADF materials, and well-known examples include: (i) Carbazolyl dicyanobenzene compounds 2CzPN (4,5-di(9H-carbazole-9-yl)phthalonitrile), DCzIPN (4,6-di(9H-carbazole-9-yl)isophthalonitrile), 4CzPN (3,4,5,6-tetra(9H-carbazole-9-yl)phthalonitrile), 4CzIPN (2,4,5,6-tetra(9H-carbazole-9-yl)isophthalonitrile), 4CzTPN (2,4,5,6-tetra(9H-carbazole-9-yl)terephthalonitrile) and its derivatives, (ii) Carbazolylcyanopyridine compounds 4CzCNPy(2,3,5,6-tetra(9H-carbazole-9-yl)-4-cyanopyridine) and its derivatives, (iii) Carbazolylcyanobiphenyl compounds CNBPCz (4,4',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2'-dicarbonitrile), CzBPCN (4,4',6,6'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-3,3'-dicarbonitrile), DDCzIPN (3,3',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2',6,6'-tetracarbonitrile) and its derivatives, Here, in these materials, one or more nitrile groups can be replaced with fluorine (F) or trifluoromethyl (CF3) as acceptor molecules.

[0114] Furthermore, nitrogen heterocycles such as triazines, pyrimidines, triazoles, oxadiazoles, thiadiazoles, heptadine, 1,4-diazatriphenylene, benzothiazoles, benzoxazoles, quinoxalines, and diazafluorene derivatives are well-known acceptor moieties used in the construction of TADF molecules. For example, known examples of TADF molecules containing a triazine acceptor include PIC-TRZ(7,7'-(6-([1,1'-biphenyl]-4-yl)-1,3,5-triazine-2,4-diyl)bis(5-phenyl-5,7-dihydroindoro[2,3-b]carbazole)), mBFCzTrz(5-(3-(4,6-diphenyl-1,3,5-triazine-2-yl))phenyl)-5H-benzofl[3,2-c]carbazole), and DCzTrz(9,9'-(5-(4,6-diphenyl-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole)).

[0115] Another group of TADF materials includes diaryl ketones such as benzophenone, or (heteroaryl)aryl ketones and their derivatives such as 4-benzoylpyridine, 9,10-anthraquinone, and 9H-xanthene-9-one, as acceptor ketones to which a donor ketone (mainly a carbazolyl substituent) is attached. Examples of such TADF molecules include BPBCz (bis(4-(9'-phenyl-9H,9'H-[3,3'-bicarbazole]-9-yl)phenyl)methanone), mDCBP ((3,5-di(9H-carbazole-9-yl)phenyl)(pyridine-4-yl)methanone), AQ-DTBu-Cz (2,6-bis(4-(3,6-di-tert-butyl-9H-carbazole-9-yl)phenyl)anthracene-9,10-dione), and MCz-XT (3-(1,3,6,8-tetramethyl-9H-carbazole-9-yl)-9H-xanthene-9-one), respectively.

[0116] Furthermore, sulfoxides, particularly diphenyl sulfoxides, are commonly used as acceptor molecules for the composition of TADF materials. Well-known examples include 4-PC-DPS (9-phenyl-3-(4-(phenylsulfonyl)phenyl)-9H-carbazole), DitBu-DPS (9,9'-(sulfonylbis(4,1-phenylene))bis(9H-carbazole)), and TXO-PhCz (2-(9-phenyl-9H-carbazole-3-yl)-9H-thioxanthene-9-one 10,10-dioxide).

[0117] The fluorescent emitter F may also exhibit TADF as defined herein, and moreover, TADF material E as defined herein. B It is understood that this is the case. As a result, a small FWHM emitter S as defined herein B This refers to TADF material E as defined herein. B It may be so, or it may not be.

[0118] Phosphorescence, that is, emission from an excited triplet state (generally the lowest excited triplet state T1), is a spin-prohibition process. As is known to those skilled in the art, phosphorescence is promoted (enhanced) by utilizing (intramolecular) spin-orbit interactions (the so-called (internal) heavy atom effect). In the context of this invention, phosphorescent material P B This is a phosphorescent emitter that can emit phosphorescence at room temperature (i.e., approximately 20°C).

[0119] Here, phosphorescent material P B Preferably, it contains at least one atom of an element having a standard atomic weight greater than the standard atomic weight of calcium (Ca). More preferably, in the context of the present invention, phosphorescent material P B This includes transition metal atoms, particularly transition metal atoms of elements having a standard atomic weight greater than that of zinc (Zn). Phosphorescent material P B The transition metal atoms preferably included exist in any oxidation state (and can also exist as ions of each element).

[0120] Phosphorescent material P used in organic electroluminescent elements B It is common knowledge to those skilled in the art that the phosphorescent material P is Ir, Pd, Pt, Au, Os, Eu, Ru, Re, Ag, and Cu, preferably Ir, Pt, and Pd, and more preferably a complex of Ir and Pt, in the context of the present invention. Those skilled in the art will know that any material in a photoelectronic device is a phosphorescent material P B It is known whether they are suitable for use as phosphorescent materials and how to synthesize them. Furthermore, those skilled in the art are familiar with the design principles of phosphorescent complexes for use as phosphorescent materials in optoelectronic devices and know how to control the emission of the complexes through structural changes.

[0121] Those skilled in the art will know that phosphorescent material P used in photoelectronic devices B It is known what materials are suitable for this purpose and how to synthesize them. In connection with this, those skilled in the art will know, in particular, that phosphorescent material P in optoelectronic devices is suitable. B We are familiar with the design principles of phosphorescent complexes for use as such, and we know how to regulate the release of the complex through structural changes.

[0122] Phosphorescent material P usable with organic molecules according to the present invention B Examples of these (for example, in the form of a composition or in an EML of a photoelectronic device, see below) are disclosed in the latest art. For example, the following metal complexes are phosphorescent materials P that can be used with the organic molecules according to the present invention. B That is the case. [ka]

[0123] In the context of the present invention, a small half-width (FWHM) emitter S B This refers to any emitter (i.e., emitter material) having an emission spectrum exhibiting an FWHM of 0.35 eV or less (≤0.35 eV), preferably 0.30 eV or less (≤0.30 eV), and particularly 0.25 eV or less (≤0.25 eV). Unless otherwise specified, this is determined based on the emission spectrum of each emitter at room temperature (i.e., (approximately) 20°C) and is generally measured in poly(methyl methacrylate) PMMA or mCBP with 1-5 wt%, particularly 2 wt%, emitters. Alternatively, a small FWHM emitter S B The emission spectrum is generally obtained at room temperature (i.e., (approximately) 20°C) with 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene. B It can be measured in a solution containing [the specified value].

[0124] Small FWHM emitter S B These are fluorescent emitters F and phosphorescent emitters (for example, phosphorescent material P). B ) and / or TADF emitters (e.g., TADF material E B ) is the aforementioned TADF material E B and phosphorescent material P B In this case, the emission spectrum is obtained at room temperature (i.e., (approximately) 20°C) for each material E in poly(methyl methacrylate) PMMA at 10 wt%. B or P B Measurements are taken from each of the spin-coated films.

[0125] As is known to those skilled in the art, emitters (for example, small FWHM emitters S B The full width at half maximum (FWHM) of the emission spectrum can be easily determined from the respective emission spectra (fluorescence spectrum for a fluorescent emitter and phosphorescence spectrum for a phosphorescent emitter). All recorded FWHM values ​​generally indicate the main emission peak (i.e., the peak with the highest intensity). The means of determining the FWHM (where preferably recorded in electron volts eV) are part of the common sense of those skilled in the art. For example, if the main emission peak of the emission spectrum reaches half of the maximum emission (i.e., 50% of the maximum emission intensity) at two wavelengths λ1 and λ2 obtained from the emission spectrum in nanometers (nm), the FWHM in electron volts (eV) is generally (and here) determined using the following equation.

number

[0126] In the context of the present invention, a small FWHM emitter S B This is an organic emitter, which in the context of the present invention means that it does not contain any transition metals. Preferably, in the context of the present invention, a small FWHM emitter S B It is mainly composed of the elements hydrogen (H), carbon (C), nitrogen (N), and boron (B), but may also contain, for example, oxygen (O), silicon (SI), fluorine (F), and bromine (Br).

[0127] Furthermore, in the context of the present invention, a small FWHM emitter S B It is preferable that the fluorescent emitter F may or may not exhibit TADF.

[0128] Preferably, in the context of the present invention, a small FWHM emitter S B It must satisfy at least one of the following requirements: (i) Boron (B) containing emitters, which are each small FWHM emitters S B This means that at least one atom inside is boron (B), (ii) comprising a polycyclic aromatic or heteroaromatic core structure in which at least two aromatic rings are condensed together (e.g., anthracene, pyrene, or aza derivatives thereof).

[0129] As is known to those skilled in the art, the host material H of EML B It can pass through EML and transport electrons or positive charges, and the host material H B It is possible to transfer excitation energy to at least one emitter material doped with H. Those skilled in the art will know that the host material H included in the EML of a photoelectronic device (e.g., OLED) B However, it is understood that when voltage and current are applied, they do not significantly affect the light emission from the element. Those skilled in the art will also understand that any host material H B However, p-host H exhibits high hole mobility. P n-host H exhibits high electron mobility N , or bipolar host material H exhibiting both high hole mobility and high electron mobility BP It is known that this is the case.

[0130] As is known to those skilled in the art, EML also has at least one p-host H P and one n-host H N This includes a so-called mixed host system having exactly one emitter material and n-host H according to the present invention. N T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine) as p-host H PThe system comprises a mixed host system containing a host selected from CBP, mCP, mCBP, 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 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.

[0131] EML is at least one p-host H P and one n-host H N This includes a so-called mixed host system having n-host H. N It contains groups derived from pyridine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine and 1,2,3-triazine, and p-host H P The group comprises indole, isoindole, and preferably a group derived from carbazole.

[0132] Those skilled in the art know what materials are suitable host materials for use in organic electroluminescent devices. Any host material used in the art is a suitable host material H in the context of the present invention. B It is understood to be that.

[0133] p-host material H in the context of the present invention P Material H B Examples are listed below: [ka] [ka] [ka] [ka] [ka] [ka]

[0134] n-host material H in the context of the present invention N Material H B Examples are listed below: [ka] [ka] [ka]

[0135] Those skilled in the art will understand that not only any material contained in the same layer, particularly the same EML, but also materials in adjacent layers that are in very close proximity at the interface between those adjacent layers can form an exciplex together. Those skilled in the art will understand that a pair of material that forms an exciplex, particularly p-host H P and n-host H N The method for selecting a pair of materials, as well as the selection criteria for the two components of the material pair, including the HOMO and / or LUMO energy requirements, are known. That is, when exciplex formation is required, one component, for example, p-host material H P The HOMO is other components, for example, n-host material H N The energy is at least 0.20 eV higher than the HOMO, and it is a single component, for example, p-host material H P The LUMO is other components, for example, n-host material H NThe energy is at least 0.20 eV higher than the LUMO. It is common knowledge to those skilled in the art that if an exciplex is present in a photoelectronic device, particularly in the EML of an OLED, the exciplex functions as an emitter material and can emit light when voltage and current are applied to the device. As is known in the art and generally, exciplexes can also be non-luminescent and, for example, if included in the EML of a photoelectronic device, can transfer excitation energy to the emitter material.

[0136] As is known to those skilled in the art, TTA (triplet-triplet annihilation) materials are host materials H B It is also used as a TTA material. TTA materials enable triplet-triplet annihilation. Triplet-triplet annihilation can preferably cause photon upconversion. Therefore, two, three or more photons can be converted into TTA material H TTA The lowest excited triplet state (T1 TTA ) to the first excited singlet state (S1 TTA Facilitates photon upconversion to ). In a preferred embodiment, two photons are converted to T1 TTA From S1 TTA This facilitates photon upconversion to triplet annihilation. Therefore, triplet annihilation is also a process in which two (or more selectively two) low-frequency photons can be coupled into one high-frequency photon through multiple energy transfer steps.

[0137] Selectively, the TTA material may contain an absorbing moisture, a sensing moisture, and an emitter moisture (or a disappearing moisture). In this regard, the emitter moisture is also a polycyclic aromatic moisture such as, for example, benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene. In a preferred embodiment, the polycyclic aromatic moisture includes anthracene moisture or a derivative thereof. The sensing moisture and the emitter moisture may be located in two different chemical compounds (i.e., separate chemical entities) or may be two moistures contained in one chemical compound.

[0138] According to the present invention, triplet-triplet annihilation (TTA) materials undergo triplet-triplet annihilation to reach the first excited triplet state T1 N From the first excited singlet state S1 N It converts energy into [something].

[0139] According to the present invention, the TTA material is in the lowest excited triplet state (T1 N ) then exhibits triplet-triplet annihilation, resulting in the first excited singlet state S1 after triplet-triplet annihilation. N Generate T1 N It is characterized by having up to twice the energy of [the other element].

[0140] In one embodiment of the present invention, the TTA material is T1 N From there, we show triplet and triplet annihilation, S1 N Generate T1 N It is characterized by having energy 1.01 to 2 times, 1.1 to 1.9 times, 1.2 to 1.5 times, 1.4 to 1.6 times, or 1.5 to 2 times the energy of the original.

[0141] In this specification, the terms "TTA material" and "TTA compound" may be used interchangeably.

[0142] Typical "TTA materials" can be found in cutting-edge technologies related to blue fluorescent OLEDs, as described by Kondakov (Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, 2015, 373: 20140321). Such blue fluorescent OLEDs use aromatic hydrocarbons, such as anthracene derivatives, as the main component (host) of the EML.

[0143] In a preferred embodiment, the TTA material enables sensitized triplet-triplet elimination. Selectively, the TTA material may contain one or more polycyclic aromatic structures. In a preferred embodiment, the TTA material contains at least one polycyclic aromatic structure and at least one further aromatic residue.

[0144] In a preferred embodiment, the TTA material has a larger singlet-triplet energy split, i.e., at least 1.1 times, at least 1.2 times, at least 1.3 times, at least 1.5 times, preferably 2 times or less, for the first excited singlet state S1 N and the lowest excited triplet state T1 N It has an energy difference with respect to

[0145] In a preferred embodiment of the present invention, TTA material H TTA It is an anthracene derivative of the chemical formula shown in chemical formula 4 below.

[0146] In one embodiment, TTA material H TTA It is an anthracene derivative of the following chemical formula 4, [ka] chemical formula 4 Here, Each Ar is independently selected from the following group: C6-C 60 Ariel, C3-C 57Heteroaryls, halogens, and C1-C 40 C6-C 60 Aryl, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C3-C 57 Heteroaryl, Each A1 is independently selected from the following group: hydrogen, deuterium, C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C6-C 60 Ariel, C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C3-C 57 Heteroaryls, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C1-C11 is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 40 (Hetero)alkyl.

[0147] In one embodiment, TTA material H TTA It is an anthracene derivative of the following chemical formula 4, Here, Each Ar is independently selected from the following group: C6-C 20 Ariel, C3-C 20 Heteroaryls, halogens, and C1-C 210C6-C 20 Aryl, and C6-C 20 Ariel, C3-C 20 Heteroaryls, halogens, and C1-C 10 C3-C 20 Heteroaryl, Each A1 is independently selected from the following group: hydrogen, deuterium, C6-C 20 Ariel, C3-C 20 Heteroaryls, halogens, and C1-C 10 C6-C 20 Ariel, C6-C 20 Ariel, C3-C 20 Heteroaryls, halogens, and C1-C 10 C3-C 20 Heteroaryls, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C1-C11 is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 10 (Hetero)alkyl.

[0148] In one embodiment, H TTA is an anthracene derivative of the following chemical formula 4, where at least one A1 is hydrogen. In one embodiment, H TTA is an anthracene derivative of the following chemical formula 4, where at least two A1s are hydrogen. In one embodiment, H TTA is an anthracene derivative of the following chemical formula 4, where at least three A1s are hydrogen. In one embodiment, H TTAThis is an anthracene derivative of the chemical formula 4 below, where all A1s are hydrogen atoms.

[0149] In one embodiment, H TTA This is an anthracene derivative of the following chemical formula 4, where at least one Ar is a residue selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, triphenylenyl, dibenzoanthracenyl, fluorenyl, benzofluorenyl, anthracenyl, phenantrenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofuranyl, and dibenzothiophenyl, which is C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 It can be selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups.

[0150] In one embodiment, H TTA This is an anthracene derivative of the chemical formula 4 below, where the two Ar groups are each independently selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, triphenylenyl, dibenzoanthracenyl, fluorenyl, benzofluorenyl, anthracenyl, phenantrenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofuranyl, and dibenzothiophenyl, and this is C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 It can be selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups.

[0151] In one embodiment, TTA material H TTA This is an anthracene derivative selected from the following: [ka] [ka] [ka] [ka]

[0152] A composition comprising at least one organic molecule according to the present invention One aspect of the present invention relates to a composition comprising at least one organic molecule according to the present invention. Another aspect of the present invention relates to the use of the composition in optoelectronic devices, preferably OLEDs, and particularly in EMLs of the devices.

[0153] In describing the aforementioned compositions, the content of specific materials in each composition will, where applicable, be referred to in the form of a percentage. It should be noted that, unless otherwise specified in a particular embodiment, all percentages refer to weight percentages, which are synonymous with weight % ((weight / weight), (w / w), wt%). For example, if the content of one or more organic molecules according to the present invention is mentioned as 30% in a particular composition, this is understood to mean that the total weight of one or more organic molecules according to the present invention (i.e., all of those molecules combined) is 30% by weight, i.e., 30% of the total weight of each composition. By providing preferred content of components in weight %, it is understood that, each time a composition is specified, the total content of all components will be summed up to 100% by weight (i.e., the total weight of the composition).

[0154] In the following description of embodiments of the present invention relating to compositions comprising at least one organic molecule according to the present invention, when the composition is used in a photoelectronic device, preferably in an EML of a photoelectronic device, most preferably in an EML of an OLED, we will refer to the energy transfer process that occurs between the components in the composition. Those skilled in the art will understand that such excitation energy transfer processes can improve the luminescence efficiency when the composition is used in an EML of a photoelectronic device.

[0155] When describing a composition comprising at least one organic molecule according to the present invention, it will also be noted that certain materials are "different" from other materials. This means that materials that are "different" from each other do not have the same chemical structure.

[0156] In one embodiment, the composition comprises or consists of the following: (a) One or more organic molecules according to the present invention (b) One or more host materials H different from the organic molecules in (a) B , and (c) One or more solvents selectively.

[0157] In one embodiment, the composition comprises or consists of the following: (a) One or more organic molecules according to the present invention, and (b) One or more host materials H different from the organic molecules in (a) B , Here, the host material H in the composition B The fraction (weight %) of is higher than the fraction (weight %) of organic molecules according to the present invention, and preferably the host material H in the composition. B The fraction (weight %) of this molecule is more than twice as high as the fraction (weight %) of the organic molecule according to the present invention.

[0158] In one embodiment, the composition comprises or consists of the following: (a) 0.1 to 30% by weight, preferably 0.8 to 15% by weight, and particularly 1.5 to 5% by weight of the organic molecule according to the present invention, (b) Host material H according to the following chemical formula 4 B TTA material as such. [ka] chemical formula 4

[0159] In one embodiment, the composition comprises or consists of the following: (a) Organic molecule according to the present invention, (b) The organic molecule in (a) and a different host material HB , and (c) TADF material E B and / or phosphorescent material P B .

[0160] In one embodiment, the composition comprises or consists of the following: (a) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, and especially 1 to 5% by weight of the organic molecule according to the present invention. (b) 0-98.8% by weight, preferably 35-94% by weight, and particularly 60-88% by weight, of one or more host materials H different from the organic molecules according to the present invention. B , (c) 0.1 to 20% by weight, preferably 0.5 to 10% by weight, and especially 1 to 3% by weight, one or more phosphorescent materials P different from the organic molecules in (a). B , (d) 1 to 99.8% by weight, preferably 5 to 50% by weight, and especially 10 to 30% by weight, of one or more TADF materials E different from the organic molecules of (a). B , and (e) One or more solvents in an amount of 0 to 98.8% by weight, preferably 0 to 59% by weight, and especially 0 to 28% by weight.

[0161] In further aspects, the present invention relates to photoelectronic devices comprising the types of organic molecules or compositions described herein, more preferably to organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED sensors, in particular to devices selected from the group consisting of gas sensors and vapor sensors not completely isolated from the outside, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion devices.

[0162] In a preferred embodiment, the photoelectronic element is an element selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0163] In one embodiment of the photoelectronic device of the present invention, the organic molecule E according to the present invention is used as an emitter material in the light-emitting layer EML.

[0164] In one embodiment of the photoelectronic device of the present invention, the light-emitting layer EML comprises the composition according to the present invention as described herein.

[0165] If the optoelectronic element is an OLED, it can have, for example, the following layer structure: 1. Circuit board 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 C Here, the OLED selectively includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are merged, and the OLED may include one or more layers from each of the layer types defined above.

[0166] In one embodiment, the photoelectronic element may selectively include one or more protective layers to protect the element from damage exposure to harmful substances in the environment, such as moisture, vapor, and / or gases.

[0167] In one embodiment of the present invention, the optoelectronic element is an OLED having the following inverted layer structure, 1. Circuit board 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. 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 selectively includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are merged, and the OLED may include one or more layers from each of the layer types defined above.

[0168] In one embodiment of the present invention, the optoelectronic element is an OLED that may have a stacked structure. In this structure, unlike the general arrangement in which OLEDs are arranged side by side, individual units are stacked on top of each other. Mixed light is generated by OLEDs exhibiting a stacked structure, and in particular, white light is generated by stacking blue OLEDs, green OLEDs, and red OLEDs. The OLED exhibiting a stacked structure may also include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally composed of an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0169] In one embodiment of the present invention, the optoelectronic element is an OLED including two or more light-emitting layers between the anode and the cathode. In particular, a 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 additional layers such as charge generation layers, charge blocking layers, or charge transport layers may be selectively included between the individual light-emitting layers. In a further embodiment, the light-emitting layers are stacked adjacent to each other. In a further embodiment, the tandem OLED includes a charge generation layer between each of the two light-emitting layers. Also, adjacent light-emitting layers, or light-emitting layers separated by a charge generation layer, may be merged.

[0170] The substrate may be formed from any material or composition of materials. Most often, 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 plastic slide may be used. This can allow for an even higher level of flexibility. The anode layer A is mostly composed of a material from which a (essentially) transparent film can be obtained. Since at least one of the two electrodes must be (essentially) transparent in order to allow light emission from the OLED, one of the anode layer A or cathode layer C is transparent. Preferably, the anode layer A contains or consists of a large amount of transparent conductive oxides (TCOs). Such an anode layer A may include, for example, indium tin oxide, aluminum zinc oxide, fluorine-doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene.

[0171] Anode layer A is made of indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1The anode layer A is (essentially) composed of ). The roughness of the anode layer A due to the transparent conductive oxide (TCO) may be mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of pseudocharge carriers in that it promotes the transport of pseudocharge carriers (i.e., holes) from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) may contain poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonic acid (PSS), MoO2, V2O5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) may also prevent the diffusion of metal from the anode layer A to the hole transport layer (HTL). For example, HIL is PEDOT:PSS (poly-3,4-ethylenedioxythiophene:polystyrene sulfonic acid), PEDOT (poly-3,4-ethylenedioxythiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'-nis-(1 It may also be composed of (-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonnitrile) and / or Spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0172] Adjacent to the anode layer A or hole injection layer (HIL), generally, a hole transport layer (HTL) is located. Here, any hole transport compound may be used. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles may be used as hole transport compounds. The HTL may reduce the energy barrier between the anode layer A and the luminescence layer (EML). The hole transport layer (HTL) may also be 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) is tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenylamine)), α-NPD (poly(4-butylphenyl-diphenylamine)), TAPC (4,4'-cyclohexyllidene-bis[N,N-bis(4-methylphenyl)benzeneamine]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)-amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN and / or TrisPcz(9,9'-diphenyl-6-(9 The HTL may also contain a star-shaped heterocycle such as (phenyl-9H-carbazole-3-yl)-9H,9'H-3,3'-bicarbazole). The HTL may also contain a p-doped layer composed of inorganic or organic dopants within the organic hole transport matrix. Examples of inorganic dopants include transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide. Examples of organic dopants include tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoic acid (Cu(I)pFBz), or transition metal complexes.

[0173] EBL may include, for example, mCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazole-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0174] The luminescent layer (EML) is generally located adjacent to the hole transport layer (HTL). The luminescent layer (EML) contains at least one luminescent molecule. In particular, the EML contains at least one organic molecule E according to the present invention. In one embodiment, the luminescent layer contains only the organic molecule according to the present invention. Generally, the EML further contains one or more host materials H. For example, host material H is CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(di The following are selected: benzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), and / or TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine). The host material H must generally be selected to exhibit first triplet (T1) and first singlet (S1) energy levels that are energetically higher than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0175] In one embodiment of the present invention, the EML comprises a so-called mixed host system having at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises exactly one luminescent organic molecule according to the present invention, T2T as the electron-dominant host, and a mixed host system comprising one selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as the hole-dominant host. In further embodiments, the EML comprises 50-80% by weight, preferably 60-75% by weight, of CBP, mCP, mCBP, a host selected from 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 the luminescent molecule according to the present invention.

[0176] An electron transport layer (ETL) may be located adjacent to the light-emitting layer (EML). Here, any electron transporter may be used. Exemplary examples include electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)phenyl (TPBi). ETL may include, for example, NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenylphosphine oxide), BPyTP2 (2,7-di(2,2'-bipyridine-5-yl)triphenyl), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene) and / or BTB (4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Selectively, the ETL may be doped with a substance such as Liq. The electron transport layer (ETL) may also block holes, or a hole blocking layer (HBL) may be introduced.

[0177] HBLs include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = basocuproin), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl- It may also contain phosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine), and / or TCB / TCP (1,3,5-tris(N-carbazol)benzene / 1,3,5-tris(carbazole)-9-yl)benzene).

[0178] A cathode layer C may be located adjacent to the electron transport layer (ETL). The cathode layer C may contain or consist of, for example, 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 consist of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively, or additionally, the cathode layer C may also contain graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also contain or consist of nanoscale silver wire.

[0179] The OLED may optionally further include a protective layer (also referred to as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The EIL layer may contain lithium fluoride, cesium fluoride, silver, Liq(8-hydroxyquinoline tritium), Li2O, BaF2, MgO and / or NaF.

[0180] Selectively, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also contain one or more host compounds H.

[0181] To further modify the emission and / or absorption spectra of the emissive layer EML, the emissive layer EML may further contain one or more additional emitter molecules F. Such emitter molecules F may be any emitter molecules known in the art. Preferably, such emitter molecules F are molecules having a different structure from that of molecule E according to the present invention. The emitter molecule F may selectively be a TADF emitter. Alternatively, the emitter molecule F may selectively be a fluorescent and / or phosphorescent emitter molecule that can shift the emission and / or absorption spectra of the emissive layer EML. For example, triplet and / or singlet excitons may be transferred from the organic emitter molecule according to the present invention to emitter molecule F before relaxing to the ground state S0, and typically emit light that is red-shifted compared to the light emitted by the organic molecule. Selectively, the emitter molecule F may also induce a two-photon effect (i.e., absorption of two photons that are half of the maximum absorption energy).

[0182] Selectively, the photoelectronic element (e.g., OLED) may be, for example, essentially a white photoelectronic element. For example, such a white photoelectronic element may include at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and / or red light. Selectively, as described above, there may be energy transfer between two or more molecules. ss

[0183] In further embodiments of the present invention, the composition has a photoluminescence quantum yield (PLQY) of more than 20%, preferably more than 30%, more preferably more than 35%, more preferably more than 40%, more preferably more than 45%, more preferably more than 50%, more preferably more than 55%, even more preferably more than 60%, or more preferably more than 70% at room temperature.

[0184] In a further aspect, the present invention relates to a method for manufacturing optoelectronic components. In this case, the organic molecules of the present invention are used.

[0185] In a further aspect, the present invention relates to a method for generating light in the wavelength range of 440 nm to 560 nm, preferably 440 nm to 470 nm, or 510 nm to 550 nm, comprising the following steps: (i) A step of providing an organic electroluminescent element containing the organic molecule of the present invention, and (ii) The step of applying an electric current to the organic electroluminescent element.

[0186] Optoelectronic devices, in particular OLEDs according to the present invention, can be manufactured by vapor deposition and / or solution processing of any means. Therefore, at least one layer is - Manufactured by the sublimation process, - Manufactured by an organic vapor deposition process, - Manufactured by a carrier gas sublimation process, - Processed with a solution or printed.

[0187] Methods used to manufacture optoelectronic devices, particularly OLEDs, according to the present invention are known in the art. Different layers are individually and sequentially deposited on a suitable substrate by a subsequent deposition process. The individual layers may be identical or deposited using different deposition methods.

[0188] For example, vapor deposition processes include thermal (co)deposition, chemical vapor deposition, and physical vapor deposition. In the case of active-matrix OLED displays, an AMOLED backplane is used as the substrate. Individual layers may also be processed from solutions or dispersions using a suitable solvent. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is selectively carried out in an inert atmosphere (e.g., a nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art.

[0189] In another aspect, the present invention also relates to an organic luminescent molecule comprising or consisting of the structure of the following chemical formula 100, [ka] chemical formula 100 Here, n=0 or 1, Each X is independently, directly joined, and CR. 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3 , NR 3 , O, SiR 3 R 4 Selected from the group consisting of S, S(O), and S(O)2, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R V The group is selected from the following: Hydrogen, deuterium, N(R) 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 CF3, CN, F, Br, I, C1-C 40 Alkyl, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR5 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C2-C40 Alkinil, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, Selectively one or more substituents R 5 C6-C replaced by 60 Aryl, and Selectively one or more substituents R 5 C2-C replaced by 57 Heteroaryl, R d and R e They are selected independently from the following groups: Hydrogen, deuterium, CF3, CN, F, Br, I, C1-C 40 Alkyl, This selectively involves one or more substituents R a Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, Selectively one or more substituents R a C6-C replaced by 60 Aryl, and Selectively one or more substituents R a C2-C replaced by 57 Heteroaryl, R a Each of them is independently selected from the following groups: Hydrogen, deuterium, N(R) 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 CF3, CN, F, Br, I, C1-C 40 Alkyl, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, C2-C 40 Alkinil, This selectively involves one or more substituents R 5 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 5 , O, S or CONR 5 Replaced by, Selectively one or more substituents R 5 C6-C replaced by 60 Aryl, and Selectively one or more substituents R 5 C2-C replaced by 57 Heteroaryl, R 5Each of them is independently selected from the following groups: Hydrogen, deuterium, N(R) 6 )2, OR 6 , Si(R 6 )3, B(OR 6 )2, B(R 6 )2, OSO2R 6 CF3, CN, F, Br, I, C1-C 40 Alkyl, This selectively involves one or more substituents R 6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 6 , O, S or CONR 6 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R 6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 6 , O, S or CONR 6 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R 6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R 6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 6 , O, S or CONR 6 Replaced by, C2-C 40 Alkinil, This selectively involves one or more substituents R 6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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, SO2, NR 6 , O, S or CONR 6 Replaced by, Selectively one or more substituents R 6 C6-C replaced by 60 Aryl, and Selectively one or more substituents R 6 C2-C replaced by 57 Heteroaryl, R 6 Each of them is independently selected from the following groups: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C6-C molecules selectively substituted with one or more C1-C5 alkyl substituents 18 Ariel, C2-C molecules selectively substituted with one or more C1-C5 alkyl substituents 17 Heteroaryl, N(C6-C 18 Ariel) 2, N(C2-C 17 Heteroaryl)2, and N(C2-C 17 (Heteroaryl)(C6-C 18 Ariel), Here, substituent R a , R d , R e and R 5 These are, independently of each other, one or more substituents R a , R d , R e and R 5 Along with selectively forming monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-condensed ring systems, Here, substituent R 1 , R 2 , R 3 , R 4 , R 5 , RI , R II , R III , R IV and R V These are, independently of each other, one or more substituents R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV and R V Along with this, it selectively forms monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-condensed ring systems. [Examples]

[0190] General synthesis method I

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] General procedure for synthesis: AAV1: I-1 (1.0 equivalent), I-2 (1.0 equivalent), Tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalent; Pd2(dba)3; CAS-No. 51364-51-3), Tri-tert-butylphosphonium tetrafluoroborate (0.04 equivalent; (tBu)3PH + BF4 - (CAS-No.131274-22-1) and sodium tert-butoxide (NaO t A suspension of Bu (CAS-No. 865-48-5, 3.0 equivalents) was stirred at 80°C for 4 hours. After cooling, the mixture was extracted between water and ethyl acetate, and the combined organic phase was dried over MgSO4, filtered, and concentrated.

[0197] AAV2: A suspension of I-3 (1.0 equivalent), I-4 (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalent; Pd2(dba)3; CAS-No. 51364-51-3), X-Phos (0.04 equivalent, CAS-No. 564483-18-7), and K3PO4 (CAS-No. 7778-53-2, 1.5 equivalents) in a degassed mixture of dioxane and water (volume ratio 4:1) was stirred under reflux for 2 hours. After cooling to room temperature, an aqueous workup was performed, and the crude product was purified by recrystallization or column chromatography. The desired compound I-5 was obtained as a solid.

[0198] At AAV3:0°C, a solution of I-5 (1.0 equivalent) in anhydrous chlorobenzene (35 mL per 1 mmol of I-5) was added to boron tribromide (99%, CAS-No. 10294-33-4, 4.0 equivalents). The mixture was warmed to room temperature and then heated at 70°C for 3.5 hours. The mixture was allowed to cool to room temperature. The mixture was then extracted between water and ethyl acetate, and the combined organic layer was dried over MgSO4, filtered, and concentrated. After purification by recrystallization or column chromatography, compound I-6 was obtained as a solid.

[0199] AAV4: I-6 (1.0 equivalent), I-7 (1.5 equivalent), tetrakis(triphenylphosphine)palladium(0) (CAS-No. 14221-01-3, 0.04 equivalent), and K3PO4 (CAS-No. 7778-53-2, 2.5 equivalents) were mixed with a degassed mixture of dioxane and water (volume ratio 5:1) and stirred under reflux for 16 hours. After cooling to room temperature, an aqueous workup was performed, and the crude product was purified by recrystallization or column chromatography. The desired target compound P-1 was obtained as a solid.

[0200] AAV10c: A suspension of E12 (1.0 equivalent), I-12 (1.1 equivalent), tris(dibenzylideneacetone)-dipalladium(0) (CAS-No. 51364-51-3, 0.06 equivalent), tri-tert-butylphosphine (CAS-No. 13716-12-6, 0.12 equivalents), and sodium tert-butoxide (CAS-No. 865-48-5, 5.0 equivalents) in degassed toluene was stirred at 100°C for 24 hours. After cooling to room temperature (rt), an aqueous workup was performed, and the crude product was purified by recrystallization or column chromatography. The desired compound I-13 was obtained as a solid.

[0201] AAV10d: A suspension of E13 (1.0 equivalent), I-14 (1.0 equivalent), tris(dibenzylideneacetone)-dipalladium(0) (CAS-No. 51364-51-3, 0.01 equivalent), tri-tert-butylphosphine (CAS-No. 13716-12-6, 0.04 equivalent), and sodium tert-butoxide (CAS-No. 865-48-5, 3.0 equivalent) in degassed toluene was stirred at 80°C for 18 hours. After cooling to room temperature (rt), an aqueous workup was performed, and the crude product was purified by recrystallization or column chromatography. The desired compound I-15 was obtained as a solid.

[0202] AAV12c:15 (1.2 equivalents), E3 (1.0 equivalent), Tris(dibenzylideneacetone)dipalladium(0) (CAS-No. 51364-51-3, 0.01 equivalents), S-PHOS (CAS-No. 657408-07-6, 0.04 equivalents), and K3PO4 (CAS-No. 7778-53-2, 2.0 equivalents) are reacted under reflux for 4 hours in a mixture of dioxane and water (4:1 volume ratio). After cooling to room temperature, the reaction mixture is extracted with ethyl acetate and water. The combined organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure. After purification by recrystallization or column chromatography, compound I-16 is obtained as a solid.

[0203] AAV13b: At 0°C, a solution of I-8b (1.0 equivalent) in anhydrous chlorobenzene (20 mL per 1 mmol of I-8b) was added to boron tribromide (99%, CAS-No. 10294-33-4, 4.0 equivalents). The mixture was warmed to room temperature and then heated at 50°C for 24 hours. The mixture was allowed to cool to room temperature. The mixture was then extracted between water and ethyl acetate, and the combined organic layer was dried over MgSO4, filtered, and concentrated. After purification by recrystallization or column chromatography, the target compound P-2 was obtained as a solid.

[0204] AAV17: I-17 (1.0 equivalent), E13 (1.5 equivalent), Tris(dibenzylideneacetone)dipalladium(0) (CAS-No. 51364-51-3, 0.02 equivalent), X-PHOS (CAS-No. 564483-18-7, 0.08 equivalent), and K3PO4 (CAS-No. 7778-53-2, 1.5 equivalent) are reacted under reflux for 4 hours in a mixture of dioxane and water (4:1 volume ratio). After cooling to room temperature, the reaction mixture is extracted with ethyl acetate and water. The combined organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure. After purification by recrystallization or column chromatography, compound P-2 is obtained as a solid.

[0205] The cyclic voltammetry circulating voltage-current is measured in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) when the concentration of the organic molecule is 10 -3 The measurement is performed using a mol / L solution. The measurement is carried out at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and relative electrode: Pt wire, reference electrode: Pt wire), with FeCp2 / FeCp2 as the internal standard. + The data was corrected using ferrocene as an internal standard for saturated calomel electrodes (SCE). HOMO data was corrected using ferrocene.

[0206] Density function theory calculation The molecular structure was optimized using the BP86 function and the Resolution of Identity (RI) approach. Excitation energies were calculated using the (BP86) optimized structure with the Time-Dependent DFT (TD-DFT) method. Orbital energies and excited state energies were calculated using the B3LYP function. The Def2-SVP basic set and m4-grid were used for numerical integration. The Turbomole program package was used for all calculations.

[0207] photophysical measurements Sample preparation: Spin coating Equipment: Spin150, SPS euro The sample concentration is 10 mg / ml when dissolved in a suitable solvent.

[0208] Program: 1) 400 U / min for 3 seconds, then 1000 U / min for 20 seconds (1000 Upm / s). 3) 4000 U / min for 10 seconds (1000 Upm / s). After coating, the film was dried at 70°C for 1 minute.

[0209] Photoluminescence spectroscopy and time-correlated single-photon counting (TCSPC) Steady-state emission spectroscopy is performed using a Model FluoroMax-4 (Horiba Scientific) equipped with a 150W xenon-Arc lamp, excitation and emission monochromator, Hamamatsu R928 photomultiplier tube, and time-correlated single-photon counting option. Standard correction fits are used to correct the emission and excitation spectra.

[0210] The excited state lifetime is determined using the same system employing the TCSPC method, along with the FM-2013 equipment and the Horiba Yvon TCSPC hub.

[0211] Excitation light source: NanoLED 370 (Wavelength: 371nm, Pulse duration: 1.1ns) NanoLED 290 (Wavelength: 294nm, Pulse duration: <1ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm)

[0212] Data analysis (exponential fitting) is performed using the DataStation and DAS6 analysis software suites. The fit is determined using the chi-squared test.

[0213] Photoluminescence quantum yield measurement For photoluminescence quantum yield (PLQY) measurements, the Absolute PL quantum yield measurement system C9920-03G (Hamamatsu Photonics) is used. Quantum yield and CIE coordinates are determined using software U6039-05 version 3.6.0.

[0214] The maximum emission is expressed in nm, the quantum yield Φ is expressed in %, and the CIE coordinates are expressed in x,y values.

[0215] PLQY is determined using the following protocol: 1) Quality Assurance: Anthracene in ethanol (existing concentration) will be used as the standard. 2) Excitation wavelength: The maximum absorption of the organic molecule is determined, and the wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured for a solution or film sample in a nitrogen atmosphere. The yield is calculated using the following equation:

number

[0216] Manufacturing and characterization of optoelectronic devices Optoelectronic elements, such as OLED elements containing organic molecules according to the present invention, can also be manufactured by a vacuum deposition method. When a layer contains one or more compounds, the weight percentage of one or more compounds is expressed in %. Since the total weight percentage value is 100%, if no value is specified, the fraction of the compound is the same as the difference between the specified value and 100%.

[0217] Unoptimized OLEDs are characterized by measuring their electroluminescence spectrum using standard methods and determining their brightness and current-dependent external quantum efficiency (%), which is calculated using the light and current detected by the photodiode. The lifetime of the OLED element is extracted from the change in brightness while operating at a constant current density. The LT50 value corresponds to the time when the measured brightness has decreased to 50% of the initial brightness, similarly, LT80 corresponds to the time when the measured brightness has decreased to 80% of the initial brightness, and LT95 corresponds to the time when the measured brightness has decreased to 95% of the initial brightness.

[0218] Accelerated lifetime measurements are performed (e.g., by applying increased current density). For example, 500 cd / m². 2 In this case, the LT80 value is determined using the following formula.

number

[0219] The value represents the average of multiple pixels (typically 2 to 8), and the standard deviation between pixels is provided.

[0220] HPLC-MS HPLC-MS analysis is performed using an Agilent HPLC (1100 series) equipped with an MS detector (Thermo LTQ XL).

[0221] A typical HPLC method is as follows: An Agilent reverse-phase column (4.6 mm × 150 mm) and a particle size of 3.5 μm (ZORBAX Eclipse Plus 95 Å C18, 4.6 × 150 mm, 3.5 μm HPLC column) are used for HPLC. HPLC-MS measurements are performed at room temperature (rt) according to the following gradient.

[0222] [Table 1]

[0223] The following solvent mixture was used: [Table 2]

[0224] Take a 5 μL injection volume from a 0.5 mg / mL concentration analyte solution for measurement.

[0225] The ionization of the probe is positive (APCI + ) Ionization mode or negative (APCI - In ionization mode, this is performed using an APCI (Atmospheric Pressure Chemical Ionization) source.

[0226] Example 1 [ka]

[0227] Example 1 was synthesized as follows: AAV1 (yield 78%), where I-1 and I-2 are represented by 5-bromo-1,3-dichloro-2-methylbenzene (CAS-No. 204930-37-0) and bis(4-tert-butylphenyl)amine (CAS-No. 4627-22-9), AAV2 (yield 56%), where I-4 is represented as 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS-No. 1510810-80-6), AAV3 (yield 76%), and AAV4 (45% yield), where I-7 was represented by 3-cyanophenylboronic acid (CAS-No. 150255-96-2).

[0228] MS (LC-MS, APCI ion source): rt (residence time): 7.997 mins at 758 m / z.

[0229] In Example 1, the maximum luminescence (at toluene of 0.001 mg / mL) was at 450 nm, with a CIEx coordinate of 0.14 and a CIEy coordinate of 0.07.

[0230] Example 2 [ka]

[0231] Example 2 was synthesized as follows: AAV1 (yield 78%), where I-1 and I-2 are represented by 5-bromo-1,3-dichloro-2-methylbenzene (CAS-No. 204930-37-0) and bis(4-tert-butylphenyl)amine (CAS-No. 4627-22-9), AAV2 (yield 56%), where I-4 is represented as 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS-No. 1510810-80-6), AAV3 (yield 76%), and AAV4 (yield 48%), where I-7 was represented as 4-cyanophenylboronic acid (CAS-No. 126747-14-6).

[0232] MS (LC-MS, APCI ion source): rt: 7.997 mins at 758 m / z.

[0233] In Example 2, the maximum luminescence (at toluene of 0.001 mg / mL) was 457 nm, the CIEx coordinate was 0.14, and the CIEy coordinate was 0.10.

[0234] Example 3 [ka]

[0235] Example 3 was synthesized as follows: AAV1 (yield 78%), where I-1 and I-2 are represented by 5-bromo-1,3-dichloro-2-methylbenzene (CAS-No. 204930-37-0) and bis(4-tert-butylphenyl)amine (CAS-No. 4627-22-9), AAV2 (yield 56%), where I-4 is represented as 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS-No. 1510810-80-6), AAV3 (yield 76%), and AAV4 (yield 48%), where I-7 was represented as (4-(1-phenyl-1H-benzo[d]imidazole-2-yl)phenyl)boronic acid (CAS-No. 952514-79-3).

[0236] MS (LC-MS, APPI ion source): rt: 926 m / z at 8.00 min.

[0237] In Example 3, the maximum emission (at toluene of 0.001 mg / mL) was at 452 nm, with a CIEx coordinate of 0.14 and a CIEy coordinate of 0.08. The photoluminescence quantum yield (PLQY) was 85%.

[0238] Example 4 [ka]

[0239] Example 4 was synthesized as follows: AAV1 (yield 78%), where I-1 and I-2 are represented by 5-bromo-1,3-dichloro-2-methylbenzene (CAS-No. 204930-37-0) and bis(4-tert-butylphenyl)amine (CAS-No. 4627-22-9), AAV2 (yield 56%), where I-4 is represented as 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS-No. 1510810-80-6), AAV3 (yield 76%), and AAV4 (yield 34%), where I-7 was represented as 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (CAS-No. 1219956-23-6).

[0240] MS (LC-MS, APPI ion source): rt: 9.6 mins at 965 m / z.

[0241] In Example 4 (0.001 mg / mL in toluene), the maximum emission was 499 nm, the CIEx coordinate was 0.24, and the CIEy coordinate was 0.43.

[0242] Example 5 [ka]

[0243] Example 5 was synthesized as follows: AAV10c (47% yield), where I-12 and E12 are represented by 1-bromo-3,5-diphenylbenzene (CAS: 103068-20-8) and 2',4',6'-trimethyl-[1,1'-biphenyl]-4-amine, respectively. AAV10d (48% yield), where I-14 and E13 are represented as 5-bromo-1,3-dichloro-2-methylbenzene (CAS:204930-37-0) and N-(2',4',6'-trimethyl-[1,1'-biphenyl]-4-yl)-[1,1':3',1”-terphenyl]-5'-amine, AAV12c (32% yield), where I-15 and E3 are represented as N-(3,5-dichloro-4-methylphenyl)-N-(2',4',6'-trimethyl-[1,1'-biphenyl]-4-yl)-[1,1':3',1”-terphenyl]-5'-amine and 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]carbazole, AAV13b (65% yield), where I-8b is represented as N-(3-(7H-benzo[c]carbazole-8-yl)-5-chloro-4-methylphenyl)-N-(2',4',6'-trimethyl-[1,1'-biphenyl]-4-yl)-[1,1':3',1”-terphenyl]-5'-amine, AAV17 (yield 52%), where I-17 and E13 were represented as 5-([1,1':3,1”-terphenyl]-5'-yl)-7-chloro-2-mesityl-8-methyl-5H-5,17b-diaza-17c-borabenzo[gh]benzo[6,7]indeno[1,2,3-no]tetrafen and 3-cyanophenylboronic acid (CAS:150255-96-2), respectively.

[0244] MS (LC-MS, APPI ion source): rt: 7.41 mins at 855 m / z.

[0245] In Example 5, the maximum emission (at toluene of 0.001 mg / mL) was 452 nm, the full width at half maximum (FWHM) was 32 nm, the CIEx coordinate was 0.14, the CIEy coordinate was 0.08, and the PLQY was 82%.

[0246] Example OLED element D1 Stacking materials [ka] Liq [ka] nBPhen [ka] HAT-CN [ka] ETM1 (electron transport material) [ka] HTL2 (Hole Transport Material) [ka] HTL1 (Hole Transport Material) [ka] Host1 (Host Materials)

[0247] Example 1 was tested with an OLED D1 fabricated with the following layer structure. [Table 3]

[0248] OLED D1 has a brightness of 1000 cd / m². 2 An external quantum efficiency (EQE) of 8.4% was calculated. The maximum emission was at 456 nm, and the FWHM was 34 nm at 3.9 V. The CIEx value was 0.138, and the CIEy value was 0.082.

[0249] Additional examples of organic molecules / oligomers of the present invention

[0250] [ka]

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Claims

1. An organic molecule consisting of the structure represented by the following chemical formula IIIa: 【Chemistry 1】 Chemical formula IIIa In chemical formula IIIa, r is an integer independently selected from 0, 1, 2, 3, or 4. s is an integer independently selected from 0, 1, 2, or 3. t is an integer selected from 0, 1, 2, 3, or 4. u is an integer selected from 1, 2, 3, 4, or 5. Here, t + u ≤ 5, R I, R ＩＩ and R ＩＩＩ Each of them is independently selected from the following groups: hydrogen, deuterium, C １ -C ６ Alkyl, and Selectively 1 or more C １ -C ６ C substituted with alkyl substituents ６ -C １２ Ariel, R ＥＷＧ is selected from the group consisting of F, CF ３ , CN, substituted or unsubstituted C ６ -C ６０ -aryl, and substituted or unsubstituted C ２ -C ５７ -heteroaryl, Ra is selected independently from the following group: Hydrogen, deuterium, N(R) ５ ) ２ , OR ５ , Si(R ５ ) ３ , B (OR ５ ) ２ , B (R ５ ) ２ OSO ２ R ５ CF ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This selectively involves one or more substituents R ５ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ５ , O, S or CONR ５ Replaced by, C １ -C ４０ Alkoxy, This selectively involves one or more substituents R ５ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ５ , O, S or CONR ５ Replaced by, C １ -C ４０ Thioalkoxy, This selectively involves one or more substituents R ５ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ５ , O, S or CONR ５ Replaced by, C ２ -C ４０ Alkenil, This selectively involves one or more substituents R ５ Replaced by, Here, one or more non-adjacent CH ２ groups are selectively R ５ C═CR ５ groups, C≡C, Si(R ５ ) ２ groups, Ge(R ５ ) ２ groups, Sn(R ５ ) ２ groups, C═O, C═S, C═Se, C═NR ５ groups, P(═O)(R ５ ) ２ groups, NR ５ groups, O, S or CONR ５ groups and are replaced by C ２ -C ４０ Alkinil, This is selectively substituted with one or more substituents R ５ and Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ５ , O, S or CONR ５ Replaced by, Selectively one or more substituents R ５ C replaced by ６ -C ６０ Aryl, and Selectively one or more substituents R ５ C replaced by ２ -C ５７ Heteroaryl, R ５ Each of them is independently selected from the following groups: Hydrogen, deuterium, N(R) ６ ) ２ , OR ６ , Si(R ６ ) ３ , B (OR ６ ) ２ , B (R ６ ) ２ OSO ２ R ６ CF ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This selectively involves one or more substituents R ６ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ６ , O, S or CONR ６ Replaced by, C １ -C ４０ Alkoxy, This selectively involves one or more substituents R ６ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ６ , O, S or CONR ６ Replaced by, C １ -C ４０ Thioalkoxy, This selectively involves one or more substituents R ６ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ６ , O, S or CONR ６ Replaced by, C ２ -C ４０ Alkenil, This selectively involves one or more substituents R ６ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ６ , O, S or CONR ６ Replaced by, C ２ -C ４０ Alkinil, This selectively involves one or more substituents R ６ Replaced by, Here, one or more non-adjacent CHs ２ The base is selectively 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 , NR ６ , O, S or CONR ６ Replaced by, Selectively one or more substituents R ６ C replaced by ６ -C ６０ Aryl, and Selectively one or more substituents R ６ C replaced by ２ -C ５７ Heteroaryl, R ６ Each of them is independently selected from the following groups: Hydrogen, deuterium, OPh, CF ３ , CN, F, C １ -C ５ Alkyl, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, and CF. ３ Or it is replaced with F, C １ -C ５ Alkoxy, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, and CF. ３ Or it is replaced with F, C １ -C ５ Thioalkoxy, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, and CF. ３ Or it is replaced with F, C ２ -C ５ Alkenil, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, and CF. ３ Or it is replaced with F, C ２ -C ５ Alkinil, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, and CF. ３ Or it is replaced with F, Selectively 1 or more C １ -C ５ C substituted with alkyl substituents ６ -C １８ Ariel, Selectively 1 or more C １ -C ５ C substituted with alkyl substituents ２ -C １７ Heteroaryl, N(C) ６ -C １８ Ariel) ２ , N(C) ２ -C １７ (Heteroaryl) ２ , and N(C) ２ -C １７ (Heteroaryl) (C ６ -C １８ Ariel), Here, any substituent R ａ , R 5 and R ６ Independently, one or more substituents R ａ , R 5 and / or R ６ Together, they form monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-condensed ring systems.

2. R ＥＷＧ The organic molecule according to claim 1, selected from the group consisting of the following: F、CF ３ ,CN, Group E, Group E consists of aryl groups having 6 to 14 aromatic ring atoms, or heteroaryl groups having 6 to 14 aromatic ring atoms, each having one or more substituents R ５ Substituted by, containing one or more group V as components of the aromatic ring, Here, one or more groups V are independently selected from the groups consisting of =N-, =C(F)-, =C(CN)-, and =C(CF3)-, respectively. Here, the heteroaryl group is not bonded via a nitrogen atom.

3. R ＥＷＧ The organic molecule according to claim 1, selected from the following structures. 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 Here, The dashed line represents substituent R. ＥＷＧ This shows a single bond connecting to the remaining part of the organic molecule represented by chemical formula I. Here, selectively, two or more adjacent substituents R ５ These can independently form monocyclic or polycyclic, aliphatic, aromatic and / or benzo-condensed ring systems, where one or more hydrogen atoms in the selectively formed ring system are R ６ It will be replaced with.

4. The organic molecule according to claim 1, wherein in chemical formula IIIa, R I is hydrogen and REWG is bonded to the para or meta position of the phenyl group.

5. The organic molecule according to claim 1, wherein R II is hydrogen and R III is a C1-C6 alkyl group.

6. R ａ Each of these is an organic molecule according to claim 1, independently selected from the group consisting of the following: Me, ｉ Pr、 ｔ This, CN, CF ３ 、 Me, ｉ Pr, ｔ Bu, CN, CF ３ A Ph selectively substituted with one or more substituents independently selected from the group consisting of and Ph, Me, ｉ Pr, ｔ Bu, CN, CF ３ Pyridinyl, selectively substituted with one or more substituents independently selected from the group consisting of and Ph, Me, ｉ Pr, ｔ Bu, CN, CF ３ Pyrimidinyl, selectively substituted with one or more substituents independently selected from the group consisting of and Ph, Me, ｉ Pr, ｔ Bu, CN, CF ３ Carbazolyl, selectively substituted with one or more substituents independently selected from the group consisting of and Ph, Me, ｉ Pr, ｔ Bu, CN, CF ３ Triazinyls selectively substituted with one or more substituents independently selected from the group consisting of and Ph, and Me, Ｉ Pr, ｔ Bu, CN, CF ３ N(Ph) selectively substituted with one or more substituents independently selected from the group consisting of and Ph. ２ , Here, two or more adjacent substituents R ａ It can form attachment points for ring systems selected from the group consisting of the following: 【Chemistry 10】 Here, each dashed line represents the condensation of the ring systems of the aforementioned group into the structure shown in chemical formula I, by condensing one of the aforementioned ring systems with two adjacent substituents R. ａ This indicates a direct connection to the position indicated.

7. Composition including the following: (a) The organic molecule according to claim 1 in emitter form, (b) A host material different from the organic molecule, and (c) Selectively, dyes and / or solvents.

8. The composition according to claim 7, comprising 0.1 to 30% by weight of the aforementioned organic molecule.

9. A photoelectronic device comprising the organic molecule described in claim 1, or the composition described in claim 7.

10. The photoelectronic element is selected from the group consisting of the following, as described in claim 9: Organic diodes Organic light-emitting diode (OLED) • Light-emitting electrochemical cell OLED sensor ・Organic solar cells Organic transistors Organic field-effect transistor • Organic lasers, and - Down-conversion element.

11. -substrate, - Anode, and - The cathode, the anode, or the cathode is disposed on the substrate, and - Includes a light-emitting layer, The photoelectronic element according to claim 9, wherein the light-emitting layer is disposed between the anode and the cathode and contains the organic molecule or the composition.

12. (i) the step of providing the optoelectronic element according to claim 10, (ii) A method for generating light in the wavelength range of 440 nm to 560 nm, comprising the step of applying an electric current to the photoelectronic element.

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