Ligands for complexes for use in optoelectronic devices

Abstract

The present invention relates to tetradentate ligands of formula I, where n is an integer selected from 0, 1, 2 or 3, m is an integer selected from 0, 1, 2, 3 or 4, and the dashed line represents an N-heterocyclic group A capable of coordinating with a central ion to form a complex. 1 , A 2 , A 3 and A 4 Z represents 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 is selected from the group consisting of: [Chemical formula I] JPEG2025505564000044.jpg76170

Description

[Technical field]

[0001] The present invention relates to ligands for organic electroluminescent compounds (complexes) and their use in organic light emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]

[0002] The problem to be solved by the present invention is to provide a ligand in the form of a complex suitable for use in an optoelectronic device. The ligand forms a compound (complex) with at least one central atom. [Means for solving the problem]

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

[0004] In one aspect of the invention, the compounds according to the invention are purely organic molecules, i.e., unlike metal complexes known for use in optoelectronic devices, they do not contain any metal ions, except for metalloids, in particular B, Si, Sn, Se and / or Ge. Effect of the Invention

[0005] The compounds (complexes) containing the ligands according to the invention exhibit a maximum emission in the blue or sky blue spectral range. They in particular exhibit a maximum emission below 560 nm, preferably below 550 nm, more preferably below 545 nm or even below 540 nm. It is generally above 500 nm, preferably above 510 nm, more preferably above 515 nm or even above 520 nm. The photoluminescence quantum yield of the compounds according to the invention is in particular 50% or more. The use of the compounds according to the invention in optoelectronic devices, for example organic light-emitting diodes (OLEDs), leads to a higher efficiency of the device or a higher color purity, expressed as the full width at half maximum (FWHM) of the emission. The corresponding OLEDs have a higher stability than known emitter substances and OLEDs with similar hues. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] Ligands according to the invention In a first aspect, the present invention relates to a ligand comprising or consisting of a structure of formula I (open tetradentate ligand L):

[0007] [Chemical formula I] JPEG2025505564000002.jpg67170, where n is an integer selected from 0, 1, 2, or 3; m is an integer selected from 0, 1, 2, 3, or 4; The dashed line JPEG2025505564000003.jpg3170 is a heterocyclic group A 1 , A 2 , A 3 and A 4 indicates that the N atom of is capable of coordinating to a central ion to form a complex, Z, in each occurrence, is independently 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 is selected from the group consisting of R a , R 3 and R 4 are each independently selected from the group consisting of: Hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , O.S.O. 2 R 5 , C.F. 3 , CN, F, Cl, Br, I, C 1 -C 40 Alkyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 1 -C 40 Alkoxy, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 )2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 1 -C 40 Thioalkoxy, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 2 -C 40 Alkenyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 2 -C 40 Alkynyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by Optionally, one or more substituents R 5 C replaced with 6 -C 60 Aryl, and Optionally, one or more substituents R 5 C replaced with 2 -C 57 Heteroaryl, R 5 is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , B(R 6 ) 2 , O.S.O. 2 R 6 , C.F. 3 ,CN,F,Br,I, C 1 -C 40 Alkyl, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 1 -C 40 Alkoxy, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 1 -C 40 Thioalkoxy, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 2 -C40 Alkenyl, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by C 2 -C 40 Alkynyl, This can be optionally substituted with one or more substituents R 6 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by Optionally, one or more substituents R 6 C replaced with 6 -C 60 Aryl, and Optionally, one or more substituents R 6 C replaced with 2 -C 57 Heteroaryl, R 6 is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, OPh, CF3 ,C.N.,F. C 1 -C 5 Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 1 -C 5 Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 1 -C 5 Thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 2 -C 5 Alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 2 -C 5 Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, Optionally, 1 or more C 1 -C 5 C substituted with alkyl substituents 6 -C 18 Aryl, Optionally, 1 or more C 1 -C 5 C substituted with alkyl substituents 2 -C 17 Heteroaryl, N(C 6 -C 18 Aryl) 2 , N(C 2 -C 17 Heteroaryl) 2 , and N(C 2 -C 17 Heteroaryl)(C 6 -C18 aryl), where the optional substituent R a , R 3 , R 4 , R 5 and R 6 independently represents one or more substituents R a , R 3 , R 4 , R 5 and / or R 6 with the selective formation of monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems, Here, A 1 and A 4 are not further linked to each other to form a closed ligand, and thus the ligand is "open."

[0008] The term "open" refers to the N-heterocyclic group A 1 and A 4 are not linked to each other, and different coordination of the ligand L to the central atom is possible. In contrast, rigid ligands such as porphyrins are said to be "closed" because they are restricted in terms of coordination.

[0009] In particular, the ligand L is a tetradentate trianionic NNNN ligand.

[0010] The ligand L may be exemplified in a coordinated form according to formula I, exhibiting three coordination sites, in a neutral non-coordinated form according to formula IU, in a trivalent anionic non-coordinated form according to formula IB, and in a coordinated form to a central atom M according to formula IM:

[0011] [Chemical formula I] JPEG2025505564000004.jpg54170[Chemical formula IU] JPEG2025505564000005.jpg53170[Chemical formula IB] JPEG2025505564000006.jpg54170[Chemical formula IM] JPEG2025505564000007.jpg55170 wherein said central atom M optionally comprises further substituents or ligands.

[0012] In addition, L may be exemplified by various mesomeric boundary structures, for example, as follows: JPEG2025505564000008.jpg38170I-U-1 IU IU-2

[0013] In one embodiment, the ligand L comprises or consists of the structure of formula II:

[0014] [Chemical formula II] JPEG2025505564000009.jpg63170.

[0015] In one embodiment, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, tBu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 , where two or more adjacent substituents R a can form an attachment point for a ring system selected from the group consisting of: JPEG2025505564000010.jpg129170 where each dashed line represents one of the ring systems depicted above separated by two adjacent substituents R a and represents a direct bond connecting the ring system of the depicted group to the structure represented by formula I.

[0016] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , One or more substituents R 5 Ph selectively substituted with One or more substituents R 5 pyridinyl optionally substituted with One or more substituents R 5 pyrimidinyl optionally substituted with One or more substituents R 5 carbazolyl optionally substituted with One or more substituents R 5triazinyl optionally substituted with One or more substituents R 5 Selectively substituted N(Ph) 2 , Here, R a Any two of the groups are optionally joined together to form a ring system selected from the group consisting of: JPEG2025505564000011.jpg18170, where X 1 is S, O or NR 5 It is.

[0017] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph.

[0018] In a further embodiment of the invention, Ra are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, Me, i Pr, t Bu, CN, CF 3 and Ph optionally substituted with one or more substituents independently selected from the group consisting of Ph.

[0019] In one embodiment, the ligand L comprises or consists of the structure of formula III:

[0020] [Chemical formula III] JPEG2025505564000012.jpg81170, where R b are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , O.S.O. 2 R 5 , C.F. 3 ,CN,F,Br,I, C 1 -C 40 Alkyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2, N.R. 5 , O, S or CONR 5 is replaced by C 1 -C 40 Alkoxy, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 1 -C 40 Thioalkoxy, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 2 -C 40 Alkenyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by C 2 -C 40 Alkynyl, This can be optionally substituted with one or more substituents R 5 is replaced by Here, one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by Optionally, one or more substituents R 5 C replaced with 6 -C 60 Aryl, and Optionally, one or more substituents R 5 C replaced with 2 -C 57 Heteroaryl.

[0021] In a further embodiment of the invention, R b are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , Me, iPr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, N(Ph) 2 .

[0022] In a further embodiment of the invention, R b are, in each occurrence, independently selected from the group consisting of: Me, i Pr, t Bu, CN, CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, tBu, CN, CF 3 and Ph, N(Ph) 2 .

[0023] In one embodiment, the ligand L comprises or consists of the structure of formula IV:

[0024] [Chemical formula IV] JPEG2025505564000013.jpg73170.

[0025] A further aspect of the invention relates to compounds comprising the ligand L as defined above.

[0026] In one embodiment, the compound of the present invention is (L) v -M-(R Y ) w The structure of the compound may be: v is an integer, where v ≥ 1; w is an integer selected from 0, 1, 2, and 3; The central atom M is selected from the group consisting of B, Si, Sn, Se, Ge, Ir, Pd, Pt, Au, Eu, Ru, Re, Ag and Cu; R Y is a substituent selected from the group consisting of a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted hydrocarbon ring group; Here, if w>1, R Y is another substituent R Y is concatenated together.

[0027] In one embodiment, M is B, Ir, Pd or Pt.

[0028] In one embodiment, the compound is an organic material, where M is B, Si, Sn, Se or Ge.

[0029] In one embodiment of the invention, the compound is a tetrahedral complex.

[0030] In one embodiment, the compound of the invention comprises or consists of the structure of LB: JPEG2025505564000014.jpg66170, where B is a four-coordinate boron atom.

[0031] In one embodiment, the compound of the invention is LB X wherein said compound is a tetrahedral complex.

[0032] definition Here, the term "layer" refers to a body having a broad planar geometric structure. It forms part of the general knowledge of the person skilled in the art that optoelectronic elements are composed of a number of layers.

[0033] In the context of the present invention, an emissive layer (EML) is a layer of an optoelectronic device, where light emission from said layer is observed upon application of a voltage and current to the device. One skilled in the art will appreciate that light emission from an optoelectronic device is due to light emission from at least one EML. A skilled artisan will appreciate that light emission from an EML is typically not (predominantly) due to all materials contained in the EML, but rather due to a particular emitter material.

[0034] In the context of the present invention, an "emitter material" or "emitter compound" (also referred to as "emitter") is a material which, when included in the light-emitting layer (EML) of an optoelectronic device, emits light when a voltage and current are applied to said device (see below). Those skilled in the art will know that emitter materials are generally "emissive dopant" materials, and will understand that dopant materials (whether emissive or not) are materials that are typically incorporated into a matrix material, referred to herein as a host material. As used herein, a host material is generally a H B It is called.

[0035] In the context of the present invention, the term "cyclic group" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0036] In the context of the present invention, when referring to chemical structures, the term "ring" is understood in the broadest sense as any monocyclic moiety. In the same respect, when referring to chemical structures, the term "ring" is understood in the broadest sense as any bicyclic or polycyclic moiety.

[0037] In the context of the present invention, the term "ring system" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0038] In the context of this invention, the term "ring atom" refers to any atom that is part of the cyclic core of a ring or ring system and is not part of a non-cyclic substituent optionally attached to the cyclic core.

[0039] In the context of this invention, the term "carbocycle" is understood in its broadest sense as any cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen as well as any other substituents as defined in specific embodiments of this invention. The term "carbocyclic" is also understood as an adjective, referring to a cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen as well as any other substituents as defined in specific embodiments of this invention.

[0040] In the context of the present invention, the term "heterocycle" is understood in the broadest sense as any cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The term "heterocyclic" is also understood as an adjective and refers to a cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The heteroatoms may be the same or different in each case, unless otherwise specified in a specific embodiment, and may be individually selected from the group consisting of preferably B, Si, N, O, S and Se, more preferably B, N, O and S, most preferably N, O and S. It goes without saying that all carbon atoms or heteroatoms contained in a heterocycle in the context of the present invention can be substituted with hydrogen or any other substituent defined in a specific embodiment of the present invention.

[0041] One of ordinary skill in the art can recognize that any cyclic group (ie, any carbocyclic and heterocyclic ring) may be aliphatic, aromatic or heteroaromatic.

[0042] In the context of the present invention, when referring to a cyclic group (i.e., one ring, multiple rings, ring system, carbocyclic ring, heterocyclic ring), the term "aliphatic" means that it contains at least one ring atom that is not part of an aromatic or heteroaromatic ring or ring system of the cyclic core structure (not including any optional attached substituents). Preferably, most of the ring atoms, more preferably all of the ring atoms in the aliphatic cyclic group are not part of an aromatic or heteroaromatic ring or ring system (e.g., in cyclohexane or piperidine). In this specification, when referring to an aliphatic ring or ring system in general, no distinction is made between a carbocyclic group and a heterocyclic group, and the term "aliphatic" is also used as an adjective to describe a carbocyclic or heterocyclic ring to indicate whether a heteroatom is included in the aliphatic cyclic group.

[0043] As will be understood by the skilled artisan, the terms "aryl" and "aromatic" are understood in their broadest sense to refer to any monocyclic, bicyclic, or polycyclic aromatic moiety, 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 specification, the terms "aryl" and "aromatic" are restricted to monocyclic, bicyclic, or polycyclic aromatic moieties in which all aromatic ring atoms are carbon atoms. In contrast, in this specification, the terms "heteroaryl" and "heteroaromatic" refer to any monocyclic, bicyclic, or polycyclic aromatic moiety in which at least one aromatic carbon ring atom is replaced by a heteroatom (i.e., not carbon). Unless otherwise stated in a particular embodiment of the invention, the at least one heteroatom in a "heteroaryl" or "heteroaromatic" in each instance 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. One of ordinary skill in the art will appreciate 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., aromatic ring system) is an aryl group, and a heteroaromatic cyclic group (i.e., heteroaromatic ring system) is a heteroaryl group.

[0044] Unless otherwise specified in a particular embodiment of the present invention, herein, an aryl group preferably comprises 6 to 60 aromatic ring atoms, more preferably 6 to 40 aromatic ring atoms, even more preferably 6 to 18 aromatic ring atoms. Unless otherwise specified in a particular embodiment of the present invention, herein, a heteroaryl group preferably comprises 5 to 60 aromatic ring atoms, more preferably 5 to 40 aromatic ring atoms, 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, more preferably N, O and S. When one or more heteroatoms are included in a heteroaromatic group, all heteroatoms are preferably selected, independently of one another, from N, O, S and Se, more preferably N, O and S.

[0045] In the context of the present invention, for both aromatic and heteroaromatic groups (e.g., aryl or heteroaryl substituents), the number of aromatic ring carbon atoms is indicated by a subscript in the definition of the particular substituent, e.g., "C 6 -C 60 The term "aryl" refers to any group of aryl that is an aliphatic, aromatic, or heteroaromatic group. This means that each aryl substituent contains from 6 to 60 aromatic carbon ring atoms. The same subscript numbers are used to indicate the number of carbon atoms permitted in all other types of substituents, whether aliphatic, aromatic, or heteroaromatic. For example, "C 1 -C 40 The term "alkyl" refers to an alkyl substituent containing from 1 to 40 carbon atoms.

[0046] Preferred examples of aryl groups include groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, or combinations of such groups.

[0047] Preferred examples of heteroaryl groups are furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, These include groups derived from 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, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, 1,2,4,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or combinations of these groups.

[0048] As used throughout this specification, the term "arylene" refers to a divalent aryl substituent that possesses two attachment sites and serves as a linker structure to another molecular structure. In the same vein, the term "heteroarylene" refers to a divalent heteroaryl substituent that possesses two attachment sites and serves as a linker structure to another molecular structure.

[0049] In the context of the present invention, when referring to an aromatic or heteroaromatic ring system, the term "fused" means that the "fused" aromatic or heteroaromatic rings share at least one bond that is part of both ring systems. For example, naphthalene (or naphthyl when referred to as a substituent) or benzothiophene (or benzothiophenyl when referred to as a substituent) are considered as fused aromatic ring systems in the context of the present invention, where the two benzene rings (in the case of naphthalene) or thiophene and benzene (in the case of benzothiophene) share one bond. Sharing a bond in such a context is also understood to include sharing the two atoms that constitute each bond, and a fused aromatic or heteroaromatic ring system is also understood as one aromatic or heteroaromatic system. It is also understood that one or more bonds are shared by the aromatic or heteroaromatic rings that constitute the fused aromatic or heteroaromatic ring system (e.g., in pyrene). An aliphatic ring system may also be fused, which will be understood to have the same meaning as an aromatic or heteroaromatic ring system, except that a fused aliphatic ring system is not aromatic. An aromatic or heteroaromatic ring system may also be fused (i.e., share at least one bond) with an aliphatic ring system.

[0050] In the context of this invention the term "condensed" ring system has the same meaning as a "fused" ring system.

[0051] In certain embodiments of the invention, adjacent substituents attached to a ring or ring system can form a further monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system fused to the aromatic or heteroaromatic ring or ring system to which said substituents are attached. Optionally, the fused ring system so formed is also understood to be larger (meaning containing more ring atoms) than the aromatic or heteroaromatic ring or ring system to which the adjacent substituents are attached. In that case (and when such a number is provided), the "total" number of ring atoms contained in the fused ring system must be understood to be the sum of the ring atoms contained in the aromatic or heteroaromatic ring or ring system. Although adjacent substituents are bonded and the ring atoms of the additional ring system are formed by the adjacent substituents, the ring atoms shared by the fused rings are counted once, not twice. For example, a benzene ring can have two adjacent substituents forming yet another benzene ring, such that a naphthalene core is formed. The naphthalene core will contain 10 ring atoms, since two carbon atoms are shared by the two benzene rings and counted only once, not twice.

[0052] Generally, in the context of the present invention, the term "adjacent substituents" or "adjacent groups" means substituents or groups which are attached to the same or adjacent atoms.

[0053] In the context of the present invention, the term "alkyl group" is understood in the 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 Cyl, 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-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-Dimethyl-n-dodec-1-yl, 1,1-Dimethyl-n-tetradec-1-yl, 1,1-Dimethyl-n-hexadecit-1-yl, 1,1-Dimethyl-n-octadec-1-yl, 1,1-Diethyl-n-hex-1-yl, 1,1-Diethyl-n-hept-1-yl, 1,1-Diethyl-n-oct-1-yl, 1,1-Diethyl-n-dec-1-yl, 1,1-Diethyl-n-dodec-1-yl , 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

[0054] For example, in s-butyl, s-pentyl, and s-hexyl, the "s" means "secondary", i.e., s-butyl, s-pentyl, and s-hexyl are the same as sec-butyl, sec-pentyl, and sec-hexyl, respectively. For example, in t-butyl, t-pentyl, and t-hexyl, the "t" means "tertiary", i.e., t-butyl, t-pentyl, and t-hexyl are the same as tert-butyl, tert-pentyl, and tert-hexyl, respectively.

[0055] As used herein, the term "alkenyl" includes straight-chain, branched and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0056] As used herein, the term "alkynyl" includes straight-chain, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0057] As used herein, the term "alkoxy" includes straight chain, branched and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

[0058] As used herein, the term "thioalkoxy" includes straight chain, branched and cyclic thioalkoxy substituents, where the O in the exemplary alkoxy group is replaced with an S.

[0059] As used herein, the term "halogen" (or, when referring to a substituent in chemical nomenclature, "halo") is also understood in its broadest sense to be any atom of an element in the seventh main group (i.e., group 17) of the Periodic Table of the Elements, preferably fluorine, chlorine, bromine or iodine.

[0060] When a molecular fragment is described as being a substituent or attached to another moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above ways of describing a substituent or an attached fragment are considered equivalent.

[0061] In addition, in this specification, "C 6 -C 60 aryl" or "C 1 -C 40 Whenever a substituent such as "alkyl" is referred to without a name indicating the point of attachment within that substituent, this means that the respective substituent may be attached via any atom. For example, "C 6 -C 60 An "aryl" substituent is attached via any 6 to 60 aromatic carbon atoms and is defined as "C 1 -C 40 An "alkyl" substituent is attached via any 1 to 40 aliphatic carbon atoms, while a "2-cyanophenyl" substituent is attached only in a manner such that its CN group is adjacent to the site of attachment in a manner that allows for accurate chemical nomenclature.

[0062] In the context of the present invention, whenever a substituent such as "butyl", "biphenyl" or "terphenyl" is mentioned without further details, this means that any isomer of the respective substituent is acceptable for that particular substituent. In this regard, for example, the term "butyl" as a substituent includes n-butyl, s-butyl, t-butyl and iso-butyl 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 site of attachment of the biphenyl substituent to the respective chemical moiety carrying the biphenyl substituent. Similarly, as a substituent, the term "terphenyl" includes 3-ortho-terphenyl, 4-ortho-terphenyl, 4-meta-terphenyl, 5-meta-terphenyl, 2-para-terphenyl or 3-para-terphenyl, where ortho, meta and para indicate the positions of the two Ph moieties in the terphenyl group relative to each other, and "2-", "3-", "4-" and "5-" indicate the sites of attachment of the terphenyl substituent to the respective chemical moieties bearing the terphenyl substituent, as known to the skilled artisan.

[0063] It is understood that all of the above defined groups, and indeed all chemical moieties, whether cyclic or acyclic, aliphatic, aromatic or heteroaromatic, can be further substituted according to the specific embodiments described herein.

[0064] All hydrogen atoms (H) contained in any structure mentioned herein are also replaced with deuterium (D), in each case independently of each other, unless specifically stated otherwise. The replacement of hydrogen with deuterium is common practice and obvious to those skilled in the art. Thus, there are many well-known methods and some review articles that can achieve this.

[0065] When comparing experimental or calculated data, values ​​must be determined by the same methodology. For example, a specified method must be used to determine the experimental ΔE STis determined to be less than 0.4 eV, comparisons are only valid if the same specific method involving the same conditions is used. To take a specific example, a comparison of the photoluminescence quantum yield (PLQY) of different compounds is only valid if the determination of the PLQY values ​​is performed under the same reaction conditions (measurements at room temperature on 10% PMMA film). Similarly, calculated energy values ​​must be determined by the same calculation method (using the same functions and the same basis set).

[0066] Optoelectronic devices comprising at least one compound having a ligand according to the invention A further aspect of the present invention relates to an optoelectronic device comprising at least one compound according to the invention.

[0067] In one embodiment, the optoelectronic device comprising at least one compound according to the invention is selected from the group consisting of: Organic Light Emitting Diode (OLED), Light-emitting electrochemical cells, OLED sensors, especially gas and steam sensors that are not completely isolated from the outside, Organic diodes, ·Organic solar cells, Organic transistors, Organic field-effect transistors, Organic lasers, and Down conversion element.

[0068] The light-emitting electrochemical cell consists of three layers: a cathode, an anode and an active layer comprising a compound according to the invention.

[0069] In a preferred embodiment, the optoelectronic device comprising at least one compound according to the invention is selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic laser and a light emitting transistor.

[0070] In a more preferred embodiment, the optoelectronic device comprising at least one compound according to the invention is an organic light emitting diode (OLED).

[0071] In one embodiment, the optoelectronic device comprising at least one compound according to the invention is an OLED having the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Light-emitting layer (also called emissive layer) (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer C Here, the OLED may optionally include each layer except for the anode layer A, the cathode layer C, and the EML, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0072] Optoelectronic devices comprising at least one compound according to the present invention may also optionally include one or more protective layers to protect the device from damaging exposure to harmful substances in the environment including, for example, moisture, vapors and / or gases.

[0073] In one embodiment, the optoelectronic device comprising at least one compound according to the invention is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer C 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Light-emitting layer (also called emissive layer) (EML) 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A Here, the OLED (having an inverted stack layer structure) optionally includes each layer except for the anode layer A, the cathode layer C, and the EML, and different layers are combined, and the OLED may include one or more layers of each layer type defined above.

[0074] The compounds according to the invention (according to the above-mentioned embodiments) can be used in various layers according to their specific structure and substitution. When used, in each layer of the optoelectronic device, in particular the OLED, the proportion of the compounds according to the invention is 0.1% to 99% by weight, more particularly 1% to 80% by weight. In an alternative embodiment, in each layer, the proportion of the compounds is 100% by weight.

[0075] In one embodiment, the optoelectronic device comprising at least one compound according to the present invention is an OLED that can have a stacked structure. In said structure, individual units are stacked on top of each other, unlike the general arrangement in which OLEDs are arranged side by side. Mixed light is generated by the OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED and a red OLED. The OLED that exhibits a stacked structure may also optionally include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally configured as an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0076] In one embodiment, the optoelectronic device comprising at least one compound according to the present invention is an OLED comprising two or more light-emitting layers between an anode and a cathode.In particular, the 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 may optionally comprise additional layers between each light-emitting layer, such as a charge generation layer, a charge blocking layer, or a charge transport layer.In a further embodiment, the light-emitting layers are stacked adjacent to each other.In a further embodiment, the tandem OLED comprises a charge generation layer between each two light-emitting layers.Also, adjacent light-emitting layers or light-emitting layers separated by a charge generation layer can be merged.

[0077] In one embodiment, an optoelectronic device comprising at least one compound according to the invention is also an essentially white optoelectronic device, meaning that the device emits white light.For example, such a white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green light and / or red light.Also, as explained later in this specification, there may be selective energy transfer between two or more molecules (see below).

[0078] In the case of an optoelectronic device comprising at least one compound according to the invention, at least one compound according to the invention is included in the light-emitting layer (EML) of the optoelectronic device, most preferably in the EML of the OLED.However, the compound according to the invention is also used, for example, in the electron transport layer (ETL) and / or the electron blocking layer (EBL) or the exciton blocking layer and / or the hole transport layer (HTL) and / or the hole blocking layer (HBL).When used, the fraction of the compound according to the invention in each layer of the optoelectronic device, especially in the OLED, is 0.1% to 99% by weight, more particularly 0.5% to 80% by weight, in particular 0.5% to 10% by weight.In an alternative embodiment, in each layer, the proportion of said compound is 100% by weight.

[0079] The selection criteria of materials suitable for the individual layers of optoelectronic devices, especially OLEDs, are common knowledge for the skilled person. The prior art shows many materials used for the individual layers, which informs which materials are suitable for use together with each other. It is understood that any material used in the prior art can also be used in optoelectronic devices comprising compounds according to the invention. Below, preferred examples of materials for the individual layers will be given. It is understood that this does not mean that all types of layers listed below must be present in an optoelectronic device comprising at least one compound according to the invention. It is further understood that an optoelectronic device comprising at least one compound according to the invention comprises one or more of each of the layers listed below, such as, for example, two or more light-emitting layers (EMLs). It is also understood that two or more layers of the same type (for example, two or more EMLs, or two or more HTLs) do not necessarily comprise the same materials, or even the same materials in the same proportions. It is also understood that an optoelectronic device comprising at least one compound according to the invention does not necessarily comprise all types of layers listed below, where an anode layer, a cathode layer and a light-emitting layer are generally present in all cases.

[0080] The substrate is made of any material or composition of materials. Mostly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g. copper, gold, silver or aluminum film) or a plastic film or a plastic slide can be used, which allows a higher level of flexibility. The anode layer A is made of a material that allows obtaining a mostly (essentially) transparent film. Since at least one of the two electrodes must be (essentially) transparent to allow light emission from the OLED, one of the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such an anode layer A may comprise, 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.

[0081] Preferably, the anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO 3 ) 0.9 (SnO 2 ) 0.1 The roughness of the anode layer A due to the transparent conducting oxide (TCO) is also mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of like charge carriers (i.e. holes) in that the transport of like charge carriers from the TCO to the hole transport layer (HTL) is promoted. The hole injection layer (HIL) is made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonic acid (PSS), MoO 2 , V 2 O 5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent diffusion of metals from the anode layer A into the hole transport layer (HTL). For example, the HIL can be poly-3,4-ethylenedioxythiophene:polystyrenesulfonate (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalene-2-yl)phenylamine (NAPH), N,N'-bis ... It is also composed of N,N'-triphenyl-N,N'-bis-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0082] Adjacent to the anode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport material can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles are also used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) can also be 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) may be formed of a material selected from the group consisting of tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzeneamine] (TAPC), 4,4',4"-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-bis-(1-naphthalene)-2,2',2'-triphenylamine (TNATA ... The HTL may comprise a star-shaped heterocyclic compound such as N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also comprise a p-doped layer composed of an inorganic or organic dopant in an organic hole-transporting matrix.The inorganic dopant may be, for example, a transition metal oxide such as vanadium oxide, molybdenum oxide or tungsten oxide. The organic dopant may be, for example, tetrafluorotetracyanoquinodimethane (F. 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes can be used.

[0083] The EBL may include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), 9-phenyl-3,6-bis(9-phenyl-9H-carbazol-3-yl)-9H-carbazole (tris-Pcz), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N′-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0084] Adjacent to the hole transport layer (HTL) or (if present) the electron blocking layer (EBL) is typically the light emitting layer (EML). The light emitting layer (EML) contains at least one light emitting molecule (i.e., emitter material). The EML typically further contains one or more host materials (also called matrix materials). For example, the host material may be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). As known to those skilled in the art, host materials should 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 that is higher in energy than the first (i.e., lowest) excited triplet state (T1) and the first (i.e., lowest) excited singlet state (S1) energy level of at least one emissive molecule incorporated into the respective host material.

[0085] As mentioned above, in the context of the present invention, it is preferred that at least one EML of an optoelectronic device comprises at least one molecule according to the invention. Preferred compositions of EMLs of optoelectronic devices comprising at least one compound according to the invention are explained in more detail later in this specification (see below).

[0086] Adjacent to the light-emitting layer (EML) may be an electron-transporting layer (ETL). Any electron-transporting material may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, triazine, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron-transporting material may also be a star-shaped heterocyclic compound such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may be, for example, 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,7-di(2,2'-bipyridin-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or 4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl (BTB). Optionally, the ETL is doped with a material such as 8-hydroxyquinolinolatolithium (Liq). The electron transport layer (ETL) can also block holes. Alternatively, a hole blocking layer (HBL) is typically introduced between the EML and the ETL.

[0087] The hole blocking layer (HBL) may be, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=bathocuproine (BCP), 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 9,9'-(5-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline)(Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST), and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0088] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g. Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also comprise or consist of nanoscale silver wires.

[0089] OLEDs comprising at least one compound according to the invention may optionally further comprise a protective layer, also called an electron injection layer (EIL), between the electron transport layer (ETL) and the cathode layer C. Such layers may be selected from the group consisting of lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li 2 O, BaF 2 , MgO and / or NaF.

[0090] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may also comprise one or more host materials.

[0091] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: >380~420nm wavelength range Deep blue: wavelength range >420~480nm Sky blue: Wavelength range >480~500nm Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: Wavelength range of >620~800nm.

[0092] Associated with the emitter molecule (i.e., emitter material), such a hue indicates the maximum emission of the primary emission peak. Thus, for example, a deep blue emitter has a maximum emission in the range >420-480 nm, a sky blue emitter has a maximum emission in the range >480-500 nm, a green emitter has a maximum emission in the range >500-560 nm, and a red emitter has a maximum emission in the range >620-800 nm.

[0093] The deep blue emitter may preferably have a maximum emission below 475 nm, more preferably below 470 nm, even more preferably below 465 nm, or even less than 460 nm. It is generally above 420 nm, preferably above 430 nm, more preferably above 440 nm, or even more preferably above 450 nm. In a preferred embodiment, the compound according to the invention has a 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, typically measured at room temperature (i.e. (about) 20° C.) from a film spin-coated with 1-5% by weight, preferably 2% by weight, of the compound according to the invention in poly(methyl methacrylate) (PMMA), mCBP, or alternatively from 0.001 mg / mL of the compound according to the invention in an organic solvent, preferably DCM or toluene.

[0094] Yet another embodiment relates to an OLED comprising at least one compound according to the invention and emitting light having CIEx and CIEy color coordinates close to the CIEx (=0.131) and CIEy (=0.046) 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, e.g. UHD-TV. A further aspect of the present invention therefore relates to an OLED comprising at least one compound according to the invention, the emission of which exhibits CIEx colour 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 very preferably 0.10 to 0.15 and / or CIEy colour 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 very preferably 0.04 to 0.10.

[0095] Yet another embodiment comprises at least one compound according to the invention and has a luminance of 1000 cd / m 2 and / or an external quantum efficiency of more than 8%, preferably more than 10%, more preferably more than 13%, even more preferably more than 15%, or even more preferably more than 20%, and / or an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, and most preferably between 450 nm and 470 nm, and / or an emission maximum of less than 500 cd / m 2 In particular, the present invention relates to OLEDs exhibiting LT80 values ​​of greater than 100 h, preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, or even more preferably greater than 1000 h.

[0096] A green emitter has a maximum emission less than 560 nm, preferably less than 550 nm, more preferably less than 545 nm, or even less than 540 nm. It is generally greater than 500 nm, preferably greater than 510 nm, more preferably greater than 515 nm, or even greater than 520 nm.

[0097] The green emitter material may preferably have a maximum emission between 500 nm and 560 nm, more preferably between 510 nm and 550 nm, and even more preferably between 520 nm and 540 nm.

[0098] In further embodiments of the invention, the composition has a photoluminescence quantum yield (PLQY) at room temperature of greater than 20%, preferably greater than 30%, more preferably greater than 35%, more preferably greater than 40%, more preferably greater than 45%, more preferably greater than 50%, more preferably greater than 55%, even more preferably greater than 60%, or even more preferably greater than 70%.

[0099] Yet another preferred embodiment concerns an OLED comprising at least one compound according to the invention and emitting at a well-defined color point. Preferably, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In a preferred embodiment, the OLED comprising at least one compound according to the invention emits light with a FWHM of the main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.1 eV or less than 0.17 eV.

[0100] According to the invention, optoelectronic devices comprising at least one compound according to the invention can be used, for example, as displays, light sources for lighting applications and as light sources for medical and / or cosmetic applications (eg phototherapy).

[0101] Combination of the compound according to the invention with additional materials It forms part of the general knowledge of the person skilled in the art that any layer within an optoelectronic device, here preferably an OLED, in particular the light-emitting layer (EML), may consist of a single material or a combination of different materials.

[0102] For example, those 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 device. However, those skilled in the art will appreciate that in the EML of an optoelectronic device (here, preferably an OLED), different materials may be present, in particular one or more host materials (i.e., matrix materials; here, the host material H B It will be appreciated that it is advantageous to combine a dopant material (referred to as an emitter material) with one or more dopant materials (ie, emitter materials), at least one of which emits light upon application of a voltage and current to the device.

[0103] In a preferred embodiment of the use of the compounds according to the invention in an optoelectronic device, said optoelectronic device comprises at least one compound according to the invention in the EML, or in a layer directly adjacent to the EML, or in one or more of these layers.

[0104] In a preferred embodiment of the use of the compounds according to the invention in an optoelectronic device, said optoelectronic device is an OLED and comprises at least one compound according to the invention in the EML, or in a layer directly adjacent to the EML, or in one or more of these layers.

[0105] In a more preferred embodiment of the use of the compounds according to the invention in an optoelectronic device, said optoelectronic device is an OLED and comprises at least one compound according to the invention in the EML.

[0106] In one embodiment relating to an optoelectronic device, preferably an OLED, comprising at least one compound according to the invention, at least one, preferably each compound according to the invention is used as emitter material in an emissive layer EML, which emits light when a voltage (and current) is applied to the device.

[0107] As known to those skilled in the art, for example, in an organic light emitting diode (OLED), emission from an emitter material (i.e., an emissive 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).

[0108] Fluorescent emitter F can emit light at room temperature (i.e., (about) 20° C.) upon electronic excitation (e.g., in an optoelectronic device), and the emissive excited state is a singlet state. Fluorescent emitters generally exhibit immediate (i.e., direct) fluorescence on the nanosecond time scale when initial electronic excitation (e.g., by electron-hole recombination) provides an excited singlet state of the emitter.

[0109] In the context of the present invention, a delayed fluorescent material is a material that can reach an excited singlet state (generally, the lowest excited triplet state T1) from an excited triplet state by reverse intersystem crossing (RISC; i.e., up-intersystem crossing or reverse intersystem crossing) and can emit light when returning from the excited singlet state (generally, S1) thus reached to the electronic ground state. The time scale (generally, microsecond range) at which the observed fluorescence emission occurs after RISC from an excited triplet state (generally, T1) to an excited singlet state (generally, S1) is slower than the time scale (generally, nanosecond range) at which direct (i.e., immediate) fluorescence occurs, and is therefore referred to as delayed fluorescence (DF). When RISC from an excited triplet state (generally, T1) to an excited singlet state (generally, S1) occurs via thermal activation and the excited singlet state thus filled emits light (delayed fluorescence emission), the process is referred to as thermally activated delayed fluorescence (TADF). Therefore, a TADF material is a material that can emit thermally activated delayed fluorescence (TADF) as described above. The lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ) and the energy difference ΔE ST It is known to those skilled in the art that the switching from the lowest excited singlet state to the lowest excited triplet state by RISC occurs with high efficiency if ΔE is reduced. Therefore, TADF materials generally have a small ΔE ST It forms part of the general knowledge of the person skilled in the art that TADF materials have a value (see below). As known to the person skilled in the art, TADF materials are not simply materials capable of RISC on their own from an excited triplet state to an excited singlet state with subsequent emission of TADF as described above. TADF materials are in fact materials that are composed of two types of materials, preferably two host materials H B , more preferably, p-host material H P and n-host material H N It is known to those skilled in the art that the exciplex formed is (see below).

[0110] The (thermally activated) delayed fluorescence evolution is analyzed, for example, based on decay curves obtained from time-resolved (i.e., transient) photoluminescence (PL) measurements. For this, spin-coated films of 1-10 wt. %, in particular 10 wt. %, of each emitter (i.e., the assumed TADF material) in poly(methyl methacrylate) (PMMA) are used as samples. The analysis is performed, for example, using an FS5 fluorescence spectrometer from Edinburgh Instruments. The sample PMMA film is placed in a cuvette and a nitrogen atmosphere is maintained during the measurements. Data collection is performed using the well-established time-correlated single photon counting (TCSPC, see below) technique. Measurements can be performed and combined in four time windows (200 ns, 1 μs, 20 μs and even longer measurement periods of >80 μs) in order to collect the entire decay dynamics over several orders of magnitude in time and signal intensity (see below).

[0111] TADF materials preferably meet the following two conditions in relation to the overall damping dynamics mentioned above: (i) the decay dynamics exhibit two time domains, one in the nanosecond (ns) range and the other in the microsecond (μs) range; and (ii) The emission spectral morphology is consistent in the two time domains.

[0112] Here, the portion of the light emitted in the first decay region is considered to be immediate fluorescence, and the portion of the light emitted in the second decay region is considered to be delayed fluorescence.

[0113] The ratio of delayed to immediate fluorescence is expressed in the form of the so-called n-value, which is calculated by integrating the respective photoluminescence decays over time according to the following equation:

[0114]

number

[0115] In the context of the present invention, TADF materials preferably exhibit an n-value (ratio of delayed to immediate fluorescence) greater than 0.05 (n>0.05), more preferably greater than 0.1 (n>0.1), even more preferably greater than 0.15 (n>0.15), particularly preferably greater than 0.2 (n>0.20) or even more preferably greater than 0.25 (n>0.25).

[0116] In the context of the present invention, the TADF material E B is the lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ) corresponds to the energy difference ΔE ST The TADF material E is characterized by exhibiting a value of less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, or even less than 0.05 eV. B ΔE ST The method for determining the value is described later in this specification.

[0117] One common approach for TADF material design is to covalently link one or more HOMO-distributed (electron) donor moieties and one or more LUMO-distributed (electron) acceptor moieties to the same bridge, referred to herein as a linker group. B can, for example, contain two or three linker groups attached to the same acceptor moiety, with additional donor and acceptor moieties attached to each of the two or three linker groups.

[0118] Also, one or more donor moieties and one or more acceptor moieties can be directly bonded to one another (without the presence of a linker group).

[0119] Typical donor moieties are derivatives of diphenylamine, indole, carbazole, acridine, phenoxazine and related structures. In particular, aliphatic, aromatic or heteroaromatic ring systems can be condensed to the aforementioned donor precursors to reach, for example, indolocarbazoles.

[0120] Derivatives of benzene, biphenyl, and to some extent terphenyl, are common linker groups.

[0121] Nitrile groups are very common acceptor moieties in TADF materials, well-known examples of which include: (i) Carbazolyldicyanobenzene compounds 2CzPN (4,5-di(9H-carbazol-9-yl)phthalonitrile), DCzIPN (4,6-di(9H-carbazol-9-yl)isophthalonitrile), 4CzPN (3,4,5,6-tetra(9H-carbazol-9-yl)phthalonitrile), 4CzIPN (2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile), 4CzTPN (2,4,5,6-tetra(9H-carbazol-9-yl)terephthalonitrile) and their derivatives, (ii) Carbazolylcyanopyridine compounds 4CzCNPy (2,3,5,6-tetra(9H-carbazol-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 their derivatives, wherein in these materials, one or more of the nitrile groups may have fluorine (F) or trifluoromethyl (CF) as an acceptor moiety. 3) can also be substituted.

[0122] Additionally, nitrogen heterocycles such as triazine, pyrimidine, triazole, oxadiazole, thiadiazole, heptazine, 1,4-diazatriphenylene, benzothiazole, benzoxazole, quinoxaline, and diazafluorene derivatives are well-known acceptor moieties used in TADF molecular constructions. For example, known examples of TADF molecules containing triazine acceptors include PIC-TRZ (7,7'-(6-([1,1'-biphenyl]-4-yl)-1,3,5-triazine-2,4-diyl)bis(5-phenyl-5,7-dihydroindolo[2,3-b]carbazole)), mBFCzTrz (5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl))phenyl)-5H-benzofuro[3,2-c]carbazole), and DCzTrz (9,9'-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole)).

[0123] Another group of TADF materials includes diaryl ketones such as benzophenone, or (heteroaryl)aryl ketones such as 4-benzoylpyridine, 9,10-anthraquinone, 9H-xanthen-9-one and their derivatives as acceptor moieties to which donor moieties (mainly carbazolyl substituents) are attached. Examples of such TADF molecules include BPBCz (bis(4-(9'-phenyl-9H,9'H-[3,3'-bicarbazol]-9-yl)phenyl)methanone), mDCBP ((3,5-di(9H-carbazol-9-yl)phenyl)(pyridin-4-yl)methanone), AQ-DTBu-Cz (2,6-bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)anthracene-9,10-dione), and MCz-XT (3-(1,3,6,8-tetramethyl-9H-carbazol-9-yl)-9H-xanthen-9-one), respectively.

[0124] Sulfoxides, particularly diphenyl sulfoxides, are also commonly used as acceptor moieties for the construction 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-carbazol-3-yl)-9H-thioxanthen-9-one 10,10-dioxide).

[0125] The fluorescent emitter F may also represent a TADF material as defined herein, and more particularly a TADF material E as defined herein. B As a result, a small FWHM emitter S as defined herein is understood to be B is the TADF material E as defined herein B It may or may not be so.

[0126] Phosphorescence, i.e., emission from an excited triplet state (typically the lowest excited triplet state T1), is a spin-forbidden process. As known to those skilled in the art, phosphorescence can be enhanced by utilizing (intramolecular) spin-orbit interactions (the so-called (internal) heavy atom effect). In the context of the present invention, the phosphorescent material P B is a phosphorescent emitter capable of emitting phosphorescence at room temperature (i.e., (about) 20° C.).

[0127] In this specification, the phosphorescent material P B It is preferred that the phosphorescent material P contains at least one atom of an element having a standard atomic weight greater than that of calcium (Ca). More preferably, in the context of the present invention, the phosphorescent material P B contains transition metal atoms, particularly transition metal atoms of elements having a standard atomic weight greater than that of zinc (Zn). B The transition metal atoms preferably present in exist in any oxidation state (and can also exist as ions of the respective elements).

[0128] Phosphorescent materials used in optoelectronic devices B It is common knowledge for a person 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 in ​​the context of the present invention, more preferably a complex of Ir and Pt. A person skilled in the art will understand what material is a phosphorescent material P in an optoelectronic device. B Those skilled in the art are also familiar with the principles of designing phosphorescent complexes for use as phosphorescent materials in optoelectronic devices, and know how to tune the emission of the complexes through structural changes.

[0129] Those skilled in the art will recognize that the phosphorescent material P used in the optoelectronic device B In this connection, the skilled person knows in particular what materials are suitable as phosphorescent materials P in optoelectronic devices and how to synthesize them. B He is familiar with the principles of designing phosphorescent complexes for use as photocatalysts and knows how to tune the emission of the complexes through structural changes.

[0130] Phosphorescent materials P that can be used with the compounds according to the invention B Examples of (for example in the form of compositions or in the EML of optoelectronic devices, see below) are disclosed in the prior art. For example, the following metal complexes can be used as phosphorescent materials P together with the compounds according to the invention: B Is: JPEG2025505564000016.jpg87170

[0131] In the context of the present invention, a small full width at half maximum (FWHM) emitter S Bis any emitter (i.e., emitter material) having an emission spectrum exhibiting a FWHM of 0.35 eV or less (≦0.35 eV), preferably 0.30 eV or less (≦0.30 eV), in particular 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., (about) 20° C.), typically measured at 1-5 wt %, in particular 2 wt %, of the emitter in poly(methyl methacrylate) (PMMA) or mCBP. Alternatively, a small FWHM emitter S B The emission spectrum of is typically measured at room temperature (i.e., (approximately) 20 °C) with 0.001–0.2 mg / mL of the emitter S in dichloromethane or toluene. B can be measured in a solution.

[0132] Small FWHM emitter S B are fluorescent emitters F, phosphorescent emitters (e.g., phosphorescent materials P B ) and / or TADF emitters (e.g., TADF materials E B ) The aforementioned TADF material E B and phosphorescent material P B In the case of B or P B The thickness is measured from each spin-coated film.

[0133] As known to those skilled in the art, the emitter (e.g., a small FWHM emitter S B The full width at half maximum (FWHM) of the emission spectrum (fluorescence spectrum for fluorescent emitters and phosphorescence spectrum for phosphorescent emitters) is easily determined from the respective emission spectrum (fluorescence spectrum for fluorescent emitters and phosphorescence spectrum for phosphorescent emitters). All reported FWHM values ​​generally represent the main emission peak (i.e., the peak with the highest intensity). Means for determining the FWHM (preferably reported herein in electron volts, eV) are part of the common knowledge of the skilled artisan. For example, if the main emission peak of an emission spectrum is determined by dividing the two wavelengths λ 2 , λ 3 , λ 4 , λ 5 , λ 6 , λ 7 , λ 8 , λ 9 , λ 10 , λ 11 , λ 12 , λ 13 , λ 14 , λ 15 , λ 20 , λ 25 , λ 30 , λ 40 , λ 50 , λ 16 , λ 20 , λ 30 , λ 40 , λ 50 , λ 17 , λ 20 , λ 25 , λ 30 , λ 20 , λ 30 , λ 40 , λ 50 , λ 20 , λ 30 , λ 20 , λ 30 , λ 30 , λ 40 , λ 50 , λ 20 , λ 3 ... 1 and λ 2When half the maximum emission (i.e., 50% of the maximum emission intensity) is reached at , the FWHM in electron volts (eV) is typically (and herein) determined using the following equation:

[0134]

number

[0135] In the context of the present invention, a small FWHM emitter S B is an organic emitter, which in the context of the present invention means that it does not contain any transition metal. Preferably, in the context of the present invention, a small FWHM emitter S B is composed primarily of the elements hydrogen (H), carbon (C), nitrogen (N) and boron (B), but can also contain, for example, oxygen (O), silicon (Si), fluorine (F) and bromine (Br).

[0136] Also, in the context of the present invention, a small FWHM emitter S B is preferably a fluorescent emitter F which may or may not additionally exhibit TADF.

[0137] Preferably, in the context of the present invention, a small FWHM emitter S B meets at least one of the following requirements: (i) Boron (B)-containing emitters, which have the respective small FWHM emitters S B At least one atom in the (ii) contain a polycyclic aromatic or heteroaromatic core structure, where at least two aromatic rings are fused together (eg, anthracene, pyrene or aza derivatives thereof).

[0138] As known to those skilled in the art, the host material H of the EML B is a host material that can transport electrons or positive charges through the EML. BThose skilled in the art will appreciate that the host material H contained in the EML of an optoelectronic device (e.g., an OLED) can transfer excitation energy to at least one emitter material doped in the EML. B Those skilled in the art will also appreciate that any host material H B However, the p-host H P , n-host H showing high electron mobility N or a bipolar host material H that exhibits both high hole and high electron mobility BP I know for a fact that it is.

[0139] As known to those skilled in the art, the EML also contains at least one p-host H P and one n-host H N In particular, the EML comprises exactly one emitter material according to the invention and a n-host H N 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T) as p-host H P The present invention also includes a mixed host system comprising 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.

[0140] The EML contains at least one p-host H P and one n-host H N This includes so-called mixed host systems, where the n-host H Nincludes groups derived from pyridine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine, and 1,2,3-triazine, and the p-host H P includes radicals derived from indole, isoindole and preferably carbazole.

[0141] A person skilled in the art knows what materials are suitable host materials for use in optoelectronic devices. Any host material used in the prior art is considered a suitable host material H in the context of the present invention. B It is understood that

[0142] In the context of the present invention, the p-host material H P Material H B Examples are listed below: JPEG2025505564000018.jpg87170JPEG2025505564000019.jpg103170JPEG2025505564000020.jpg12517 0JPEG2025505564000021.jpg77170JPEG2025505564000022.jpg85170JPEG2025505564000023.jpg49170

[0143] In the context of the present invention, the n-host material H N Material H B Examples are listed below: JPEG2025505564000024.jpg96170JPEG2025505564000025.jpg130170JPEG2025505564000026.jpg47170

[0144] Those skilled in the art will appreciate that any materials contained in the same layer, particularly the same EML, as well as materials in adjacent layers that are in close proximity at the interface between those adjacent layers, can form exciplexes together. P and n-host H NThe present invention relates to a method for selecting a pair of materials, and selection criteria for the two components of the material pair, including HOMO and / or LUMO energy requirements. That is, when exciplex formation is required, one component, e.g., the p-host material H P The HOMO of the n-host material H N The HOMO of the p-host material H P The LUMO of the n-host material H N The exciplex has an energy at least 0.20 eV higher than the LUMO of the exciplex. It is common knowledge for those skilled in the art that if an exciplex is present in the EML of an optoelectronic device, especially an OLED, the exciplex can function as an emitter material and emit light when voltage and current are applied to the device. As is known from the prior art and generally, an exciplex can also be non-emissive and can transfer excitation energy to an emitter material, for example, when it is included in the EML of an optoelectronic device.

[0145] As known to those skilled in the art, TTA (triplet-triplet annihilation) materials are compounds that react with a host material H B The TTA material also allows triplet-triplet annihilation. Triplet-triplet annihilation can preferably cause photon upconversion. Thus, two, three or more photons can be converted into the TTA material H TTA The lowest excited triplet state (T1 TTA ) to the first excited singlet state S1 TTA In a preferred embodiment, the two photons are TTA From S1 TTA Thus, triplet-triplet annihilation may be the step by which two (or, alternatively, more than two) low frequency photons can be combined into one high frequency photon by multiple energy transfer steps.

[0146] Alternatively, the TTA material may include an absorbing moiety, a sensitizer moiety, and an emitter moiety (or a quenching moiety). In this regard, the emitter moiety may be a polycyclic aromatic moiety, such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, or azulene. In a preferred embodiment, the polycyclic aromatic moiety includes an anthracene moiety or a derivative thereof. The sensitizer moiety and the emitter moiety may be located in two different chemical compounds (i.e., separate chemical entities) or may be two moieties contained in one chemical compound.

[0147] According to the present invention, a triplet-triplet annihilation (TTA) material is a material that is capable of converting an excited triplet state T1 N to the first excited singlet state S1 N Converts energy into

[0148] According to the present invention, the TTA material is a material having a lowest excited triplet state (T1 N ) to the first excited singlet state S1 N Generate T1 N It is characterized by having up to twice the energy of

[0149] In one embodiment of the present invention, the TTA material is T1 N From triplet-triplet annihilation, S1 N Generate T1 N The energy of the compound is 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 compound.

[0150] In this specification, the terms "TTA material" and "TTA compound" may be used interchangeably.

[0151] Exemplary "TTA materials" can be found in the prior art 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.

[0152] In a preferred embodiment, the TTA material allows for sensitized triplet-triplet annihilation. Optionally, the TTA material may comprise one or more polycyclic aromatic structures. In a preferred embodiment, the TTA material comprises at least one polycyclic aromatic structure and at least one further aromatic moiety.

[0153] In a preferred embodiment, the TTA material has a larger singlet-triplet energy splitting, 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, of the first excited singlet state S1 N and the lowest excited triplet state T1 N has an energy difference with

[0154] In a preferred embodiment of the present invention, the TTA material H TTA is an anthracene derivative.

[0155] In one embodiment, the TTA material H TTA is an anthracene derivative represented by the following chemical formula 4:

[0156] [Chemical formula 4] JPEG2025505564000027.jpg39170, where Each Ar is independently selected from the group consisting of: C 6 -C 60 Aryl, C 3 -C 57Heteroaryl, halogen and C 1 -C 40 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 6 -C 60 Aryl, and C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 3 -C 57 Heteroaryl, Each A 1 are independently selected from the group consisting of: hydrogen, deuterium, C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 6 -C 60 Aryl, C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 3 -C 57 Heteroaryl, and C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 1 -C 40 (Hetero)alkyl.

[0157] In one embodiment, the TTA material H TTA is an anthracene derivative of the above-mentioned Chemical Formula 4, Where: Each Ar is independently selected from the group consisting of: C 6 -C 20 Aryl, C 3 -C 20 Heteroaryl, halogen and C 1 -C 10 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 6 -C 20 Aryl, and C 6 -C 20 Aryl, C 3 -C 20 Heteroaryl, halogen and C 1 -C 10 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 3 -C 20 Heteroaryl, Each A 1 are independently selected from the group consisting of: hydrogen, deuterium, C 6 -C 20 Aryl, C 3 -C 20 Heteroaryl, halogen and C 1 -C 10 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 6 -C 20 Aryl, C 6 -C 20 Aryl, C 3 -C 20 Heteroaryl, halogen and C 1 -C 10 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 3 -C 20 Heteroaryl, and C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 C optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl 1 -C 10 (Hetero)alkyl.

[0158] In one embodiment, H TTA is an anthracene derivative of the above formula 4, wherein at least one A 1 is hydrogen. In one embodiment, H TTA is an anthracene derivative of the above formula 4, wherein at least two A 1 is hydrogen. In one embodiment, H TTA is an anthracene derivative of the above formula 4, wherein at least three A 1 is hydrogen. In one embodiment, H TTA is an anthracene derivative of the above formula 4, wherein all A 1 are hydrogen.

[0159] In one embodiment, H TTA is an anthracene derivative of the formula 4, wherein one Ar is a residue selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, triphenylenyl, dibenzoanthracenyl, fluorenyl, benzofluorenyl, anthracenyl, phenanthrenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofuranyl, and dibenzothiophenyl, which is C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 It may be optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl.

[0160] In one embodiment, H TTAis an anthracene derivative of the formula 4, wherein the two Ar are each independently a residue selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, triphenylenyl, dibenzoanthracenyl, fluorenyl, benzofluorenyl, anthracenyl, phenanthrenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofuranyl, and dibenzothiophenyl, which is C 6 -C 60 Aryl, C 3 -C 57 Heteroaryl, halogen and C 1 -C 40 It may be optionally substituted with one or more residues selected from the group consisting of (hetero)alkyl.

[0161] Compositions containing compounds according to the present invention One aspect of the present invention relates to a composition comprising at least one compound according to the invention. Another aspect of the present invention relates to the use of said composition in an optoelectronic device, preferably an OLED, in particular in the EML of said device.

[0162] Hereinafter, when describing the above compositions, the content of a specific material in each composition may be referred to in the form of percentage. It should be noted that unless otherwise specified in a specific embodiment, all percentages refer to weight percentages, which have the same meaning as weight percentages or weight % ((weight / weight), (w / w), wt%). For example, when the content of one or more compounds according to the present invention is illustratively referred to as 30% in a specific composition, this is understood to mean that the total weight of one or more compounds according to the present invention (i.e., all of their molecules combined) is 30% by weight, i.e., 30% of the total weight of the respective composition. By providing the preferred content of a component in weight %, it is understood that each time a composition is specified, the total content of all components adds up to 100% by weight (i.e., the total weight of the composition).

[0163] In the following description of the embodiments of the present invention relating to compositions comprising at least one compound according to the present invention, reference will be made to energy transfer processes occurring between components in said compositions when they are used in optoelectronic devices, preferably in the EML of an optoelectronic device, most preferably in the EML of an OLED. Those skilled in the art will understand that such excitation energy transfer processes can improve the luminous efficiency when the compositions are used in the EML of an optoelectronic device.

[0164] When describing a composition that includes at least one compound according to the invention, it will also be noted that the particular material is "different" from other materials, meaning that the materials that are "different" from each other do not have the same chemical structure.

[0165] In one embodiment, the composition comprises or consists of: (a) one or more compounds according to the invention; (b) one or more host materials H different from the compound of (a); B , and (c) optionally one or more solvents.

[0166] In one embodiment, the composition comprises or consists of: (a) one or more compounds according to the invention, and (b) one or more host materials H different from the compound of (a); B , Here, the host material H B is higher than the fraction (wt%) of the compound according to the invention, and preferably the host material H B is more than twice as high as the fraction (wt. %) of the compound according to the invention.

[0167] In one embodiment, the composition comprises or consists of: (a) 0.1 to 30% by weight, preferably 0.8 to 15% by weight, in particular 1.5 to 5% by weight, of a compound according to the invention, and (b) a host material H represented by the following chemical formula 4: B TTA materials as:

[0168] [Chemical formula 4] JPEG2025505564000028.jpg40170.

[0169] In one embodiment, the composition comprises or consists of: (a) a compound according to the present invention, (b) A host material H different from the compound in (a) B , and (c)TADF material E B and / or phosphorescent material P B .

[0170] In one embodiment, the composition comprises or consists of: (a) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, in particular 1 to 5% by weight, of a compound according to the invention, (b) 0 to 98.8% by weight, preferably 35 to 94% by weight, in particular 60 to 88% by weight, of one or more host materials H different from the compounds according to the invention. B , (c) 0.1 to 20% by weight, preferably 0.5 to 10% by weight, in particular 1 to 3% by weight, of one or more phosphorescent materials P different from the compounds of (a). B , (d) 1 to 99.8% by weight, preferably 5 to 50% by weight, in particular 10 to 30% by weight, of one or more TADF materials E different from the compounds of (a). B , and (e) 0 to 98.8% by weight, preferably 0 to 59% by weight, in particular 0 to 28% by weight, of one or more solvents.

[0171] In a further aspect, the present invention relates to an optoelectronic device comprising a compound or composition of the type described herein, in particular in the form of a device selected from the group consisting of organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, in particular gas and vapor sensors that are not completely sealed off from the outside, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and down conversion devices.

[0172] In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC) and a light emitting transistor.

[0173] In one embodiment of the inventive optoelectronic device, the compound E according to the invention is used as emitter material in the light-emitting layer EML.

[0174] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the inventive composition described herein.

[0175] When the optoelectronic device is an OLED, it can have, for example, the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer Here, the OLED optionally includes layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0176] Additionally, in one embodiment, the optoelectronic device may optionally include one or more protective layers that protect the device from damaging exposure to harmful substances in the environment including, for example, moisture, steam and / or gases.

[0177] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Light-emitting layer B 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A Here, the OLED optionally includes layers selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0178] In one embodiment of the present invention, the optoelectronic element is an OLED that can have a stacked structure. In this structure, individual units are stacked on top of each other, unlike the common arrangement in which OLEDs are arranged side by side. Mixed light is generated by an OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED, and a red OLED. An OLED that exhibits a stacked structure may also include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally configured as an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0179] In one embodiment of the present invention, the optoelectronic device is an OLED that includes two or more light-emitting layers between an anode and a cathode. In particular, the so-called tandem OLED includes three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and may optionally include additional layers between each light-emitting layer, such as a charge generation layer, a charge blocking layer, or a charge transport layer. In a further embodiment, the light-emitting layers are stacked adjacently. In a further embodiment, the tandem OLED includes a charge generation layer between each two light-emitting layers. Also, adjacent light-emitting layers or light-emitting layers separated by a charge generation layer can be merged.

[0180] The substrate is made of any material or composition of materials. Mostly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g. copper, gold, silver or aluminum film) or a plastic film or a plastic slide can be used, which allows a higher level of flexibility. The anode layer A is made of a material that allows obtaining a mostly (essentially) transparent film. Since at least one of the two electrodes must be (essentially) transparent to allow light emission from the OLED, one of the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such an anode layer A may comprise, 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.

[0181] The anode layer A is made of (essentially) indium tin oxide (ITO) (e.g., InO 3 ) 0.9 (SnO 2 )0.1 The roughness of the anode layer A due to the transparent conducting oxide (TCO) is also mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of like charge carriers (i.e. holes) in that the transport of like charge carriers from the TCO to the hole transport layer (HTL) is promoted. The hole injection layer (HIL) is made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonic acid (PSS), MoO 2 , V 2 O 5 , CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent diffusion of metals from the anode layer A into the hole transport layer (HTL). For example, the HIL can be poly-3,4-ethylenedioxythiophene:polystyrenesulfonate (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalene-2-yl)phenylamine (NAPH), N,N'-bis ... It is also composed of N,N'-triphenyl-N,N'-bis-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0182] Adjacent to the anode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles are also used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) can 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) may be tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′,4″-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or 9, The HTL may comprise a star-shaped heterocycle such as 9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also comprise a p-doped layer consisting of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopants may be transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide. The organic dopants may be tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes can be used.

[0183] The EBL may include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0184] Adjacent to the hole transport layer (HTL) is generally located an emissive layer (EML). The emissive layer (EML) comprises at least one emissive molecule. In particular, the EML comprises at least one compound E according to the present invention. In one embodiment, the emissive layer comprises only compounds according to the present invention. Generally, the EML further comprises one or more host materials H. For example, the host material H may be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), mCP, mCBP, dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), CzSi, dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(diphenylphosphino ... benzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). The host material H should generally be selected to exhibit a first triplet (T1) and a first singlet (S1) energy level that is energetically higher than the first triplet (T1) and the first singlet (S1) energy level of the organic molecule.

[0185] In one embodiment of the present invention, the EML comprises a so-called mixed host system, which has at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises a mixed host system comprising exactly one emissive compound according to the present invention, T2T as an electron-dominant host, and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as a hole-dominant host. In a further embodiment, the EML comprises 50-80% by weight, preferably 60-75% by weight, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 10-45% by weight, preferably 15-30% by weight, of T2T, and 5-40% by weight, preferably 10-30% by weight, of an emissive molecule according to the present invention.

[0186] Adjacent to the light-emitting layer (EML) may be an electron-transporting layer (ETL). Any electron transporter may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxides, and sulfones may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may be 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,7-di(2,2'-bipyridin-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) and / or 4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl (BTB). Optionally, the ETL is also doped with a material such as Liq. The electron transport layer (ETL) can also block holes. Alternatively, a hole blocking layer (HBL) is introduced.

[0187] Examples of HBL include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine (BCP), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), and aluminum-tris(8-hydroxyquinoline) (Alq 3), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST), and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0188] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g. Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also comprise or consist of nanoscale silver wires.

[0189] The OLED may optionally further include a protective layer (also called an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The layer may be any of lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li 2 O, BaF 2 , MgO and / or NaF.

[0190] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may also comprise one or more host compounds H.

[0191] To additionally modify the emission and / or absorption spectrum of the emissive layer EML, the emissive layer EML may further comprise one or more additional emitter molecules F. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F are molecules having a structure different from that of the molecules E according to the invention. The emitter molecules F may optionally be TADF emitters. Alternatively, the emitter molecules F may optionally be fluorescent and / or phosphorescent emitter molecules capable of shifting the emission and / or absorption spectrum of the emissive layer EML. For example, triplet and / or singlet excitons may be induced in the ground state S 0 before being relaxed to , the compound according to the invention can be transferred to the emitter molecule F, which can emit light that is typically red-shifted compared to the light emitted by the compound according to the invention. Optionally, the emitter molecule F can also induce a two-photon effect (i.e. the absorption of two photons that are half the maximum absorbed energy).

[0192] Alternatively, the optoelectronic device (e.g., an OLED) may be, for example, an essentially white optoelectronic device. For example, such a white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and / or red light. And, optionally, there may be energy transfer between two or more molecules, as described above.

[0193] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: >380~420nm wavelength range Deep blue: wavelength range >420~480nm Sky blue: Wavelength range >480~500nm Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: Wavelength range of >620~800nm.

[0194] Associated with the emitter molecule, such hues exhibit maximum emission, so for example, a deep blue emitter has a maximum emission in the range >420-480 nm, a sky blue emitter has a maximum emission in the range >480-500 nm, a green emitter has a maximum emission in the range >500-560 nm, and a red emitter has a maximum emission in the range >620-800 nm.

[0195] Deep blue emitters can preferably have a maximum emission less than 480 nm, more preferably less than 470 nm, even more preferably less than 465 nm, or even less than 460 nm. It is generally greater than 420 nm, preferably greater than 430 nm, more preferably greater than 440 nm, or even greater than 450 nm.

[0196] A green emitter has a maximum emission less than 560 nm, more preferably less than 550 nm, even more preferably less than 545 nm, or even less than 540 nm. It is generally greater than 500 nm, more preferably greater than 510 nm, even more preferably greater than 515 nm, or even more preferably greater than 520 nm.

[0197] Thus, a further aspect of the present invention is 2 and / or an external quantum efficiency of more than 8%, preferably more than 10%, more preferably more than 13%, even more preferably more than 15%, or even more than 20%; and / or an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm; and / or an emission maximum of less than 500 cd / m 2and preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, or even more preferably greater than 1000 h. Accordingly, a further aspect of the invention relates to an OLED whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20, even more preferably less than 0.15, or even more preferably less than 0.10.

[0198] A further aspect of the present invention relates to an OLED emitting light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD displays, e.g., UHD-TVs. In this specification, the term "close" refers to the CIEx and CIEy ranges provided at the end of the paragraph. While in commercial applications, a top light-emitting element (where the top electrode is transparent) is typically used, the test element used throughout the present invention shows a bottom light-emitting element (where the bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx colour coordinates of 0.15 to 0.45, preferably 0.15 to 0.35, more preferably 0.15 to 0.30, even more preferably 0.15 to 0.25 or even more preferably 0.15 to 0.20, and / or CIEy colour coordinates of 0.60 to 0.92, preferably 0.65 to 0.90, more preferably 0.70 to 0.88, even more preferably 0.75 to 0.86 or even more preferably 0.79 to 0.84.

[0199] Thus, a further aspect of the present invention is 2and / or an external quantum efficiency of more than 8%, preferably more than 10%, more preferably more than 13%, even more preferably more than 15%, or even more preferably more than 17%, or even more preferably more than 20%, and / or an emission maximum between 485 nm and 560 nm, preferably between 500 nm and 560 nm, more preferably between 510 nm and 550 nm, even more preferably between 515 nm and 540 nm, and / or an emission maximum of 14500 cd / m 2 In particular, the present invention relates to OLEDs exhibiting LT97 values ​​of greater than 100 h, preferably greater than 250 h, more preferably greater than 500 h, even more preferably greater than 750 h, or even more preferably greater than 1000 h.

[0200] A further aspect of the present invention relates to an OLED that emits light at a well-defined color point. According to the present invention, the OLED emits light with a narrow emission band (small FWHM). In one aspect, the OLED according to the present invention emits light with a FWHM of the main emission peak less than 0.25 eV, preferably less than 0.20 eV, more preferably less than 0.17 eV, even more preferably less than 0.15 eV, or even less than 0.13 eV.

[0201] In further embodiments of the invention, the composition has a photoluminescence quantum yield (PLQY) at room temperature of greater than 20%, preferably greater than 30%, more preferably greater than 35%, more preferably greater than 40%, more preferably greater than 45%, more preferably greater than 50%, more preferably greater than 55%, even more preferably greater than 60%, or even more preferably greater than 70%.

[0202] In a further aspect, the invention relates to a method for producing an optoelectronic component, in which the compound of the invention is used.

[0203] In a further aspect, the present invention relates to a method for generating light in the wavelength range of 510 nm to 550 nm, preferably 520 nm to 540 nm, comprising the steps of: (i) providing an optoelectronic device comprising a compound of the invention; and (ii) applying a current to the optoelectronic device;

[0204] The optoelectronic device, in particular the OLED according to the invention, may be produced by any means of vapor deposition and / or liquid processes. Thus, at least one layer may be - Produced by the sublimation process; -Manufactured by organic vapor phase deposition process, - Produced by a carrier gas sublimation process; - Solution processed or printed.

[0205] The methods used to manufacture optoelectronic devices, in particular OLEDs, according to the present invention are known in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition steps. The individual layers may be deposited using the same or different deposition methods.

[0206] For example, the vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. The individual layers are also processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art.

[0207] Working Example General synthesis method: JPEG2025505564000029.jpg97170

[0208] General procedure for synthesis: AAV1: E1 (1.00 equivalents, e.g., bis(6-bromopyridin-2-yl)amine, CAS: 1195970-59-2), E2 (2.30 equivalents, e.g., 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, CAS: 1219637-88-3), tris(dibenzylideneacetone)dipalladium(0) (0.03 equivalents; CAS: 51364-51-3), X-Phos (0.1 equivalents; CAS: 564483-18-7) and potassium acetate (KOAc; CAS: 127-08-2, 4.00 equivalents) were stirred in a mixture of dehydrated dioxane and degassed water (10:1) under nitrogen atmosphere at 90° C. for 24 hours. After cooling to room temperature (rt), the reaction mixture was extracted between ethyl acetate and water. The organic phase was collected and diluted with MgSO 4 The mixture was dried at 40° C., treated with Celite® and Charcoal, stirred for 1 h, and filtered. The combined organic layers were concentrated under reduced pressure. The crude product was purified by column chromatography or recrystallization to give E3 as a solid.

[0209] AAV2: E3 (1.00 equiv.) was stirred in anhydrous chlorobenzene under nitrogen atmosphere and the solution was cooled to 0° C. Boron tribromide (E4, 1.50 equiv.; CAS: 10294-33-4) was added dropwise and stirred under nitrogen atmosphere for 15 minutes. The reaction mixture was then heated to 60° C. for 16 hours.

[0210] The reaction mixture was allowed to cool to room temperature. DIPEA was added to the mixture until the mixture was basic. Methanol was added to the mixture and the crude product P1 was filtered as a solid and washed with methanol.

[0211] Cyclic Voltammetry Cyclic voltammograms are performed at concentrations of 10 -3The measurement is performed at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and FeCp 2 / FeCp 2 + The HOMO data were corrected using ferrocene as an internal standard relative to a saturated calomel electrode (SCE).

[0212] Density functional theory calculations The molecular structures were optimized using the BP86 function and the Resolution of Identity (RI) approach. The excitation energies were calculated with the Time-Dependent DFT (TD-DFT) method using the (BP86) optimized structures. The orbital energies and excited state energies were calculated with the B3LYP function. For numerical integration, the Def2-SVP basis set and m4-grid were used. The Turbomole program package was used for all calculations.

[0213] optical physical measurements Sample preparation: spin coating Equipment: Spin150, SPS euro Sample concentration is 10 mg / ml dissolved in an appropriate solvent.

[0214] Program: 1) 400 U / min for 3 sec, 1000 U / min for 20 sec (1000U / min). 3) 4000 U / min for 10 sec (1000U / min). After coating, the film was dried at 70° C. for 1 min.

[0215] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC) Steady-state emission spectroscopy is measured using a Model FluoroMax-4 (Horiba Scientific) equipped with a 150 W Xenon-Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and time-correlated single photon counting options. Standard correction fits are used to correct the emission and excitation spectra.

[0216] The excited state lifetimes are determined using the same system using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub.

[0217] Excitation light source: NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns) NanoLED 290 (wavelength: 294nm, pulse duration: <1ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm) Data analysis (exponential fit) is performed using the software suite DataStation and DAS6 analysis software. The fit is determined using the chi-squared test.

[0218] Photoluminescence quantum yield measurement For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0219] Emission maxima are given in nm, quantum yields Φ are given in %, and CIE coordinates are given as x,y values.

[0220] The PLQY is determined using the following protocol: 1) Quality assurance: Anthracene (known concentration) in ethanol is used as the standard.

[0221] 2) Excitation wavelength: The absorption maximum of the compound is determined and that wavelength is used to excite the molecule.

[0222] 3) Measurement The quantum yield is measured on solution or film samples in a nitrogen atmosphere. The yield is calculated using the following equation:

[0223]

number

[0224] Fabrication and characterization of optoelectronic devices The optoelectronic device, especially the OLED device, containing the compound according to the invention can also be manufactured by vacuum deposition method. When a layer contains one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so when no value is specified, the fraction of the compound is the same as the difference between the specified value and 100%.

[0225] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance, similarly LT80 corresponds to the point when the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the point when the measured luminance has decreased to 95% of the initial luminance.

[0226] Accelerated lifetime measurements are performed (e.g. by applying increased current densities), e.g. 500cd / m 2 In the present invention, the LT80 value is determined using the following formula:

[0227]

number

[0228] The value corresponds to the average of several pixels (typically 2-8) and the standard deviation across the pixels is provided.

[0229] HPLC-MS: HPLC-MS analysis is performed on an Agilent HPLC (1100 series) equipped with an MS-detector (Thermo LTQ XL).

[0230] For example, a typical HPLC method is as follows: A reversed phase column 4.6 mm×150 mm, particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6×150 mm, 3.5 μm HPLC column) is used for the HPLC. The HPLC-MS measurements are performed at room temperature (rt) with the following gradient:

[0231] [Table 1]

[0232] The following solvent mixtures were used:

[0233] [Table 2]

[0234] From the analyte solution at a concentration of 0.5 mg / mL, an injection volume of 5 μL is taken for the measurement.

[0235] The ionization of the probe is by cation (APCI + ) ionization mode or negative (APCI - ) ionization mode using an APCI (atmospheric pressure chemical ionization) source.

[0236] Example 1 JPEG2025505564000034.jpg48170(Ligand L1 JPEG2025505564000035.jpg49170 (complex containing

[0237] Example 1 was synthesized by:

[0238] AAV1-1 (49% yield), in which 6-bromo-N-pyridin-2-ylpyridin-2-amine: JPEG2025505564000036.jpg25170(1195970-59-2) is used as material E-1, JPEG2025505564000037.jpg33170(CAS 1219637-88-3) is used as material E-2, and AAV2 (yield 76%).

[0239] MS (LC-MS, APCI ion source): 510 m / z at rt: 7.04 min Example 1 (0.001 mg / mL in dichloromethane) has an emission maximum of 529 nm with a CIEx coordinate of 0.28 and a CIEy coordinate of 0.58.

Claims

1. A ligand comprising the structure of Formula I: [Chemical formula I] where: n is an integer selected from the group consisting of 0, 1, 2, and 3; m is an integer selected from the group consisting of 0, 1, 2, 3, and 4; A １ is an N-heterocycle optionally substituted with one or more substituents; A ２ is an N-heterocycle optionally substituted with one or more substituents; A ３ is an N-heterocycle optionally substituted with one or more substituents; A ４ is an N-heterocycle optionally substituted with one or more substituents; The dashed line is the N-heterocyclic group A １ , A ２ , A ３ and A ４ wherein the N atom of is capable of coordinating to a central ion to form a complex; Z, in each occurrence, is independently 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 is selected from the group consisting of R ａ , R ３ and R ４ are each independently selected from the group consisting of: Hydrogen, deuterium, N(R ５ ) ２ , OR ５ , Si(R ５ ) ３ , B(OR ５ ) ２ , B(R ５ ) ２ , OSO ２ R ５ , C.F. ３ ,CN,F,Cl,Br,I, C １ -C ４０ Alkyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C １ -C ４０ Alkoxy, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C １ -C ４０ thioalkoxy, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C ２ -C ４０ alkenyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C ２ -C ４０ Alkynyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by Optionally, one or more substituents R ５ C substituted with ６ -C ６０ aryl, and Optionally, one or more substituents R ５ C substituted with ２ -C ５７ heteroaryl, R ５ is, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R ６ ) ２ , OR ６ , Si(R ６ ) ３ , B(OR ６ ) ２ , B(R ６ ) ２ , OSO ２ R ６ , C.F. ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C １ -C ４０ Alkoxy, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C １ -C ４０ thioalkoxy, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C ２ -C ４０ alkenyl, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by C ２ -C ４０ Alkynyl, This may optionally be one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by Optionally, one or more substituents R ６ C substituted with ６ -C ６０ aryl, and Optionally, one or more substituents R ６ C substituted with ２ -C ５７ heteroaryl, R ６ is, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh, CF ３ ,C.N.,F. C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, Optionally, one or more C １ -C ５ C substituted with alkyl substituents ６ -C １８ aryl, Optionally, one or more C １ -C ５ C substituted with alkyl substituents ２ -C １７ heteroaryl, N (C ６ -C １８ aryl) ２ , N (C ２ -C １７ Heteroaryl) ２ , and N (C ２ -C １７ Heteroaryl) (C ６ -C １８ aryl), where any substituent R ａ , R ３ , R ４ , R ５ and R ６ independently represents one or more substituents R ａ , R ３ , R ４ , R ５ and / or R ６ with the selective formation of monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic and / or benzo-fused ring systems, Here, A １ and A ４ Is A ２ and A ３ They are not connected to each other except through

2. The ligand of claim 1 , wherein the ligand comprises the structure of Formula II: [Chemical formula II]

3. R ａ is, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, and Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph) ２ , In particular, where two or more adjacent substituents R ａ forms an attachment point for a ring system selected from the group consisting of: where each dashed line separates one of the ring systems depicted above from two adjacent substituents R ａ and represents a direct bond connecting the ring system of the group represented above to the structure represented by Formula I.

4. N-heterocycle A １ and N-heterocycle A ２ 2. The ligand of claim 1, wherein at least one N-heterocycle selected from the group consisting of: is a substituted or unsubstituted pyridine.

5. The ligand of claim 1 , wherein the ligand comprises the structure of Formula III: [Chemical formula III] Here, R ｂ is, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R ５ ) ２ , OR ５ , Si(R ５ ) ３ , B(OR ５ ) ２ , OSO ２ R ５ , C.F. ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C １ -C ４０ Alkoxy, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C １ -C ４０ thioalkoxy, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C ２ -C ４０ alkenyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by C ２ -C ４０ Alkynyl, This may optionally be one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by Optionally, one or more substituents R ５ C substituted with ６ -C ６０ aryl, and Optionally, one or more substituents R ５ C substituted with ２ -C ５７ Heteroaryl.

6. R ｂ is, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me、 ｉ Pr、 ｔ Bu、CN、CF ３ 、 Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, and N(Ph) ２ .

7. The ligand of claim 1 , wherein the ligand comprises the structure of Formula IV: [Chemical formula IV]

8. 2. The ligand of claim 1, wherein the ligand is coordinated to a central atom selected from the group consisting of B, Si, Sn, Se, Ge, Ir, Pd, Pt, Au, Eu, Ru, Re, Ag, and Cu to form a complex.

9. 10. Use of a ligand according to any one of claims 1 to 8 for the preparation of a complex, in particular a boron complex.

10. A complex having a central atom and at least one ligand comprising a ligand according to any one of claims 1 to 8.

11. A composition comprising: (a) a complex according to claim 10, in particular in emitter form, (b) a host material different from the complex; and (c) optionally, a dye and / or a solvent.

12. An optoelectronic device comprising, in particular as a light emitter, a complex according to claim 10.

13. 13. The optoelectronic device of claim 12, wherein the optoelectronic device is selected from the group consisting of: - organic diodes, Organic Light Emitting Diodes (OLEDs), - light-emitting electrochemical cells, OLED sensors, ・Organic solar cells, - organic transistors, - organic field effect transistors, organic lasers, and - Down conversion element.

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

15. (i) providing an optoelectronic device according to claim 12; (ii) applying an electric current to said optoelectronic device.

16. A consumer product comprising an optoelectronic device according to claim 12, in particular in the form of an organic light emitting device (OLED).

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