Heterocyclic compounds containing boron and nitrogen

Abstract

Disclosed is a heterocyclic compound containing boron and nitrogen. The compound adopts a novel heterocyclic structure containing boron and nitrogen, and can be used as a light-emitting material, a host material, a charge blocking material, a charge transporting material, etc. in an electroluminescent device. The compound can provide a very narrow light-emitting spectrum, and realize high saturation deep blue light-emitting. Also disclosed are an organic light-emitting device and a compound formulation.

Description

[0001] This application claims priority to U.S. Provisional Application No. 62 / 614,353, filed January 5, 2018, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a heterocyclic compound containing boron and nitrogen, and an organic electroluminescent device and compound formulation containing the compound. Background Art

[0003] Organic electronic devices include, but are not limited to, the following categories: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photoreceptors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmonic light-emitting devices.

[0004] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0005] OLEDs can be categorized into three different types based on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. Triplet states generated in the device are wasted through non-radiative decay channels. As a result, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metal complexes as the emitter. This allows for the harvesting of both singlet and triplet states, achieving an IQE of 100%. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0006] OLEDs can also be categorized based on the form of the materials used, into small molecule and polymer OLEDs. A small molecule is any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers, with their well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0007] Various OLED manufacturing methods exist. Small molecule OLEDs are typically produced by vacuum thermal evaporation. Polymer OLEDs are produced using solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be produced using solution methods if the material can be dissolved or dispersed in a solvent.

[0008] The luminescent color of OLEDs can be achieved through the structural design of luminescent materials. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life, and high operating voltage. Commercial full-color OLED displays generally adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which remains a problem. In addition, it is expected to have a more saturated luminescent spectrum, higher efficiency, and longer device life.

[0009] Currently, phosphorescent blue OLEDs have a short lifespan and struggle to achieve deep blue. Fluorescent blue OLEDs, while having a longer lifespan than phosphorescent blue OLEDs, have low efficiency. Therefore, there is a great need to improve the lifespan and efficiency of blue OLEDs. Blue luminescent materials with thermally activated delayed fluorescence (TADF) properties have been used to achieve high external quantum efficiency (EQE). However, most TADF luminescent materials exhibit very broad emission spectra, making them undesirable for display applications. Therefore, there is a great need for new TADF materials with narrow emission spectra. Summary of the Invention

[0010] The present invention aims to provide a series of novel boron- and nitrogen-containing heterocyclic compounds to address at least some of the aforementioned issues. These compounds can be used as luminescent materials, host materials, charge blocking materials, charge transport materials, and other materials in organic light-emitting devices. In particular, as luminescent materials, these novel compounds can provide a very narrow emission spectrum, achieving highly saturated deep-blue luminescence.

[0011] According to one embodiment of the present invention, a compound having a structure of Formula I is disclosed:

[0012]

[0013] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0014] R is each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0015] Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14At least one of the four groups is carbon and connected by a C-C single bond;

[0016] Furthermore, the compound is not a fullerene-type compound.

[0017] According to another embodiment of the present invention, an organic light-emitting device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes a compound having a structure of Formula I:

[0018]

[0019] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0020] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0021] Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14 At least one of the four groups is carbon and is connected by a C-C single bond;

[0022] Furthermore, the compound is not a fullerene-type compound.

[0023] According to another embodiment of the present invention, a compound formulation is also disclosed, which contains the compound having the structure of Formula I.

[0024] The novel boron- and nitrogen-containing heterocyclic compounds disclosed in this invention can be used as luminescent materials, host materials, charge blocking materials, charge transport materials, and other materials in electroluminescent devices. In particular, as luminescent materials, these novel compounds can provide a very narrow luminescence spectrum, achieving highly saturated deep-blue emission. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compound or compound formulation disclosed herein.

[0026] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compound or compound formulation disclosed herein. DETAILED DESCRIPTION

[0027] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0028] There are many more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entireties. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0029] The above layered structures are provided by way of non-limiting examples. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired emission spectrum.

[0030] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.

[0031] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is shown schematically and non-limitingly. Figure 1The difference is that an encapsulation layer 102 can also be included above cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0032] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0033] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0034] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, the cathode may be described as being "disposed on" the anode even if various organic layers are present between the cathode and the anode.

[0035] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0036] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is not believed to contribute to the photoactive properties of the emissive material, but the ancillary ligand may modify the properties of the photoactive ligand.

[0037] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0038] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the inverse intersystem crossing (IRISC) rate is fast enough to minimize the non-radiative decay by the triplet, the fraction of backfilling the singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the electrically generated excitons.

[0039] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0040] Definition of Substituent Terms

[0041] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0042] Alkyl groups include both straight-chain and branched alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Additionally, alkyl groups may be optionally substituted. Carbon atoms in the alkyl chain may be replaced by other heteroatoms. Of the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, and neopentyl are preferred.

[0043] Cycloalkyl - as used herein, encompasses cyclic alkyl groups. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. In addition, cycloalkyl groups may be optionally substituted. The carbon atoms in the ring may be substituted with other heteroatoms.

[0044] Alkenyl - as used herein, encompasses both straight and branched alkene groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl. In addition, alkenyl groups may be optionally substituted.

[0045] Alkynyl - as used herein, encompasses both straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Additionally, alkynyl groups may be optionally substituted.

[0046] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. Preferred aryl groups are those containing 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. In addition, aryl groups may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl.

[0047] Heterocyclyl or heterocycle - As used herein, both aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclyl groups are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, and sulfur. The heterocyclyl group may also be an aromatic heterocyclyl group having at least one heteroatom selected from nitrogen, oxygen, sulfur, and selenium.

[0048] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups that may contain from 1 to 5 heteroatoms are contemplated. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...

[0049] Alkoxy groups are represented by -O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, include methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy. Alkoxy groups having 3 or more carbon atoms may be linear, cyclic, or branched.

[0050] Aryloxy is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. Examples of aryloxy having 6 to 40 carbon atoms include phenoxy and biphenyloxy.

[0051] Aralkyl - As used herein, an alkyl group having an aryl substituent. In addition, an aralkyl group may be optionally substituted. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl Benzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-2-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred.

[0052] The term "aza" in azadibenzofuran, aza-dibenzothiophene, etc., means that one or more CH groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives will readily occur to one of ordinary skill in the art, and all such analogs are intended to be included within the terminology described herein.

[0053] The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclyl, aryl and heteroaryl groups may be unsubstituted or substituted with one or more groups selected from deuterium, halogen, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0054] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attaching a fragment are considered equivalent.

[0055] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in compounds may be preferred because it enhances device efficiency and stability.

[0056] In the compounds mentioned in this disclosure, poly(twice) substitution refers to a range including di(twice) substitution up to the maximum number of available substitutions.

[0057] According to one embodiment of the present invention, a compound having formula I is disclosed:

[0058]

[0059] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0060] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkyl having 2 to 20 carbon atoms substituted or unsubstituted alkenyl groups having 6 to 30 carbon atoms, substituted or unsubstituted aryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, thio groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0061] Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14 At least one of the four groups is carbon and is connected by a CC single bond; and the compound is not a fullerene-type compound.

[0062] Fullerene is a class of compounds composed of carbon and having a cage structure. Cage structures include spherical cages, ellipsoidal cages, tubular cages, onion-shaped cages, and clusters containing the above four cage structures. Typical fullerene family members include C 20 、C24 、C 26 、C 28 、C 32 、C 50 、C 60 、C 70 ...C 540 Etc. In the present application, fullerene-type compounds refer to compounds containing carbon and partially substituted carbon heteroatoms and having a cage structure. Its structure is similar to that of fullerene, including spherical cage type, ellipsoidal cage type, tubular, onion-shaped, and clusters containing the above four cage structures. The compounds of multiple structures disclosed in this application are not fullerene-type compounds. The key point is that the compound molecules containing the structure represented by any of the multiple formulas disclosed in this application do not constitute a spatially closed structure, such as spherical cage type, ellipsoidal cage type, tubular, onion-shaped, and clusters containing the above four cage structures.

[0063] According to one embodiment of the present invention, the compound has a structure of Formula II or Formula III:

[0064]

[0065] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0066] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof,

[0067] And the compound is not a fullerene-type compound.

[0068] According to one embodiment of the present invention, wherein Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10, Y 13 and Y 14 Of the four groups, at least two are carbon and connected by C—C single bonds.

[0069] According to one embodiment of the present invention, the compound has a structure of Formula IV, Formula V, Formula VI or Formula VII:

[0070]

[0071] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0072] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof,

[0073] And the compound is not a fullerene-type compound.

[0074] According to one embodiment of the present invention, wherein Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14 At least three of the four groups are carbon and connected by CC single bonds.

[0075] According to one embodiment of the present invention, the compound has a structure of Formula VIII or Formula IX:

[0076]

[0077] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0078] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof,

[0079] And the compound is not a fullerene-type compound.

[0080] According to one embodiment of the present invention, wherein Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14 All four groups are carbon and connected by C—C single bonds.

[0081] According to one embodiment of the present invention, the compound has a structure of Formula X:

[0082]

[0083] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0084] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof,

[0085] And the compound is not a fullerene-type compound.

[0086] According to a preferred embodiment of the present invention, the compound is selected from the group consisting of Compound 1 to Compound 648, the specific structures of Compound 1 to Compound 197 are shown in Claim 5, the specific structures of Compound 198 to Compound 611 are shown in Claim 6, and the specific structures of Compound 612 to Compound 648 are shown in Claim 7.

[0087] According to one embodiment of the present invention, at least one R comprises a substituent selected from the group consisting of phenyl, biphenyl, polyphenyl, diarylamine, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, dibenzoselenophene, azadibenzoselenophene, triphenylene, azatriphenylene, tetra-o-phenylene, diarylsilyl and triarylsilyl.

[0088] For the above multiple embodiments disclosed in this application, as long as Y in the structure of the compound shown is 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14 If any of the four groups are connected, all such connections must be directly connected via C-C single bonds. In other words, the connection is not formed by connecting other atoms or groups. This is clearly confirmed by the structures described in the examples of this application.

[0089] In the above-mentioned embodiments disclosed in this application, when Y 1 -Y 18 When there are multiple CRs, each R may be the same or different. This can be clearly determined from the structures described in the embodiments of the present application.

[0090] According to one embodiment of the present invention, there is further disclosed a first organic light-emitting device, comprising:

[0091] anode,

[0092] cathode,

[0093] and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of Formula I:

[0094]

[0095] where Y 1 -Y 18 are each independently selected from C, CR or N;

[0096] wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0097] Y 1 and Y 18 , Y 4 and Y 5 , Y 9 and Y 10 , Y 13 and Y 14 At least one of the four groups is carbon and is connected by a CC single bond; and the compound is not a fullerene-type compound.

[0098] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the compound is a light-emitting material.

[0099] According to one embodiment of the present invention, the organic layer further comprises a host material.

[0100] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the compound is a host material.

[0101] According to one embodiment of the present invention, wherein the organic layer is a charge carrier blocking layer, the compound is a charge carrier blocking material in the organic layer.

[0102] According to one embodiment of the present invention, wherein the organic layer is a charge carrier transport layer, the compound is a charge carrier transport material in the organic layer.

[0103] According to one embodiment of the present invention, the first organic light emitting device is incorporated into a device selected from the group consisting of: a consumer product, an electronic component module, an organic light emitting device, and a lighting panel

[0104] According to another embodiment of the present invention, a compound formulation is also disclosed, which comprises a compound represented by Formula I. The specific structure of the compound is shown in any of the aforementioned embodiments.

[0105] Combination with other materials

[0106] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0107] The materials described herein as being useful for specific layers in an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0108] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection.All reaction solvents are anhydrous and are used as is from commercial sources. Synthetic product uses one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator etc.), with methods well known to those skilled in the art, carried out structure confirmation and characteristic test. Because those skilled in the art are aware of the related contents such as the use of above-mentioned equipment, testing method, it is possible to obtain the inherent data of sample with certainty and without being affected, so above-mentioned related contents are no longer expanded and repeated in this patent.

[0109] Material synthesis example:

[0110] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0111] Synthesis Example 1: Synthesis of Compound 395

[0112] Step 1: Synthesis of Intermediate 1

[0113]

[0114] To a 500mL three-necked flask, add 1-bromo-9H-carbazole (20g, 81mmol), o-fluoronitrobenzene (22g, 162mmol), cesium carbonate (80g, 243mmol), and DMSO (160mL). Stir at room temperature for 48h. Add saturated brine (50mL) and extract the organic matter with PE / DCM (3 / 1, 500mL). Separate the layers, combine the organic phases, and wash with saturated brine until the aqueous phase is colorless. Concentrate and separate by column chromatography (PE / DCM = 3 / 1) to obtain Intermediate 1 (15.86g, 54% yield) as a yellow solid.

[0115] Step 2: Synthesis of Intermediate 2

[0116]

[0117] To a 2L three-necked flask, add Intermediate 1 (13 g, 35.7 mmol), N₂H₄·H₂O (5 mL, 85.8 mmol), FeCl₃ (347 mg, 2.14 mmol), activated carbon (1.3 g), and toluene / ethanol (1 / 1, 900 mL). Heat to 90°C with stirring. Add 5 mL (85.8 mmol) of N₂H₄·H₂O ten times until the reaction is complete as determined by TLC. Filter and concentrate to obtain Intermediate 2 (12 g, 99% yield) as a yellow solid.

[0118] Step 3: Synthesis of Intermediate 3

[0119]

[0120] Take a 250mL single-necked bottle, add intermediate 2 (12g, 35.7mmol), dissolve it in acetonitrile (80mL), add concentrated hydrochloric acid (excess) and stir. After ten minutes, move the reaction to an ice-water bath and stir. Add an aqueous solution of sodium nitrite (5g, 71.4mmol) dropwise to the reaction. After half an hour, add an aqueous solution of potassium iodide (18g, 107.1mmol) dropwise to the reaction, maintaining stirring in an ice-water bath. Monitor the reaction by TLC. Filter through celite at low temperature. Extract the organic matter with ethyl acetate three times, combine the organic phases, concentrate, and separate the crude product by column chromatography, eluting with PE / DCM = 30 / 1 to obtain intermediate 3 as a white solid (9g, yield 57%).

[0121] Step 4: Synthesis of compound 395

[0122]

[0123] In a 50 mL single-necked flask, add intermediate 3 (1 g, 2.2 mmol). Replace the air with nitrogen three times, add tetrahydrofuran (11 mL), and stir in a dry ice-ethanol bath for half an hour. Add n-butyl lithium (5 mL, 8 mmol) and stir for half an hour. Then add trimethyl borate (0.75 mL, 6.6 mmol) and continue stirring for 0.5 h. In another single-necked flask, add o-chloroiodobenzene (2.8 mL, 22 mmol) and tetrahydrofuran (11 mL). Stir in an ice-water bath for half an hour. Add a solution of iPrMgCl·LiCl in tetrahydrofuran (17 mL, 22 mmol) and stir for half an hour. Add the borate solution in tetrahydrofuran to the reaction mixture. Stir for 2 hours, then add distilled water (0.5 mL). Concentrate, and extract the organic matter with dichloromethane three times. The organic phases were combined and concentrated, and the resulting crude product was separated by column chromatography using PE as the eluent to obtain compound 395 (455 mg, 57% yield). The product was confirmed to be the target product with a molecular weight of 364.

[0124] Synthesis Example 2: Synthesis of Compound 247

[0125]

[0126] To a single-necked flask, compound 395 (40 mg, 0.11 mmol), diphenylamine (22 mg, 0.13 mmol), Pd(OAc)2 (3.3 mol%, 1 mg), Xphos (6 mol%, 3 mg), tBuONa (21 mg, 0.22 mmol), and toluene (1 mL) were added. The mixture was bubbled with nitrogen and stirred at 120°C for 4 hours. The mixture was concentrated and the resulting crude product was separated by column chromatography using PE as the eluent to obtain compound 247 (3 mg, 5% yield). The product was confirmed to be the desired product with a molecular weight of 496.

[0127] Synthesis Example 3: Synthesis of Compound 396

[0128]

[0129] In a 50 mL single-necked flask, add 1-bromo-9-(2-iodophenyl)-9H-carbazole (1 g, 2.2 mmol). The air was replaced with nitrogen three times, and tetrahydrofuran (11 mL) was added. The mixture was stirred in a dry ice-ethanol bath for half an hour. n-Butyl lithium (3.5 mL, 8 mmol) was added and stirred for half an hour. Trimethyl borate (0.75 mL, 6.6 mmol) was added and stirring continued for 0.5 h. In another single-necked flask, o-bromoiodobenzene (2.5 mL, 22 mmol) and tetrahydrofuran (11 mL) were added. The mixture was stirred in an ice-water bath for half an hour. A solution of iPrMgCl·LiCl in tetrahydrofuran (16 mL, 22 mmol) was added and stirred for half an hour. The borate solution in tetrahydrofuran was added to the reaction mixture. The mixture was stirred for 2 hours, and distilled water (0.5 mL) was added. The mixture was concentrated, and the organic matter was extracted with dichloromethane three times. The organic phases were combined and concentrated, and the resulting crude product was separated by column chromatography using PE as the eluent to obtain compound 396 (400 mg, 45% yield). The product was confirmed to be the target product with a molecular weight of 408.

[0130] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0131] In the structure of the compound of the present invention, the nitrogen atom contains an unbonded lone pair of electrons, and the boron atom contains an empty orbital. By designing the molecular structure, the electron donor (nitrogen atom) and the electron acceptor (boron atom) in the molecule play a synergistic role in the polyaromatic ring system, thereby achieving a small energy level difference between the S1 state and the T1 state. For example, the ΔEst of compound 395 is 0.11eV, while the ΔEst of compound 396 is only 0.03eV. It can be seen that this type of compound meets the candidate compound requirements of TADF materials. In addition, through the characteristics of Formula IX of the present invention, while maintaining the polyaromatic ring system, the rigidity of the molecular skeleton is improved. For example, the emission wavelength of the fluorescence spectrum of compounds 395 and 396 is in the deep blue light region, the half-peak width of the emission spectrum of compound 395 is 31.9nm, and the half-peak width of the emission spectrum of compound 396 is 28.9nm, which has a very narrow half-peak width value. Compared with the TADF material (general half-peak width>100nm) in which the electron donor and the electron acceptor are placed at both ends of the molecule, the advantage is obvious. The half-peak width of 35 nm of comparative compound 1 (US Pat. No. 9,073,948 B2) is also narrower.

[0132]

[0133] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. Compounds of formula II: Wherein in Formula II, Y 1 -Y 3 、Y 6 -Y 18 Each independently selected from CR; wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; And the compound is not a fullerene-type compound.

2. The compound according to claim 1, wherein the compound has the structure of Formula II: Wherein in Formula II, Y 1 -Y 3 、Y 6 -Y 18 Each is independently selected from CR; wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted amine group having 0-20 carbon atoms, and combinations thereof.

3. The compound of claim 1, wherein each R is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, nitrile, and combinations thereof.

4. The compound according to claim 1, wherein the compound is selected from the group consisting of: In the above compound structure, Ph is Cz is NPh2 is N(3-BP)2 is N(4-BP)2 is N(2-Fl)2 is N(3-Fl)2 is N(4-Fl)2 is NPh(4-BP) is N(2-Fl)(4-BP) is N(3-Fl)(4-BP) is NPh(2-Fl) is NPh(3-Fl) is NPh(3-BP) is 5. The compound of claim 1 , wherein at least one R comprises a substituent selected from the group consisting of phenyl, biphenyl, polyphenyl, diarylamine, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, dibenzoselenophene, azadibenzoselenophene, triphenylene, azatriphenylene, tetra-o-phenylene, diarylsilyl, and triarylsilyl.

6. A first organic light-emitting device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 5. The first organic light-emitting device according to claim 6 , wherein the organic layer is a light-emitting layer, and the compound is a light-emitting material. The first organic light-emitting device according to claim 7 , wherein the organic layer is a light-emitting layer, wherein the organic layer further comprises a host material.

9. The first organic light-emitting device according to claim 6, wherein the organic layer is a light-emitting layer and the compound is a host material; or wherein the organic layer is a charge carrier blocking layer and the compound is a charge carrier blocking material in the organic layer; or wherein the organic layer is a charge carrier transport layer and the compound is a charge carrier transport material in the organic layer.

10. The first organic light emitting device of claim 6, wherein the first organic light emitting device is incorporated into a device selected from the group consisting of: a consumer product.

11. The first organic light emitting device according to claim 6, wherein the first organic light emitting device is incorporated into a device selected from the group consisting of: an electronic component module, an organic light emitting device, and a lighting panel.

12. A compound formulation comprising the compound according to any one of claims 1 to 5.

Images