CN116813600A

CN116813600A - Organic electroluminescent material and device thereof

Info

Publication number: CN116813600A
Application number: CN202210261277.4A
Authority: CN
Inventors: 王阳; 李锋; 姚剑飞; 杨刚; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Xiahe Technology Jiangsu Co ltd
Priority date: 2022-03-18
Filing date: 2022-03-18
Publication date: 2023-09-29

Abstract

An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is a compound having the structure of formula 1, which is useful in an organic electroluminescent device, for example, as a host material, a transport material, or the like. The compounds can improve the electron and hole transmission balance capability of the material, so that the organic electroluminescent device has longer service life and can provide better device performance. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Organic electroluminescent material and device thereof

Technical Field

The present invention relates to compounds for use in organic electronic devices, such as organic electroluminescent devices. And more particularly, to a compound having a structure of formula 1, and an organic electroluminescent device and a compound composition including the compound.

Background

Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

In 1987, tang and Van Slyke of Isomandah reported a double-layered organic electroluminescent device comprising 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 biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced OLEDs may 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. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.

OLEDs can be divided into three different types according to their light emission mechanism. The OLED of the Tang and van Slyke invention is a fluorescent OLED. It uses only singlet light emission. The triplet states generated in the device are wasted through non-radiative decay channels. Thus, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation prevents commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters. Thus, both singlet and triplet states can be harvested, achieving a 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.

OLEDs can also be classified into small molecule and polymeric OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecules can be large as long as they have a precise structure. Dendrimers with a defined structure are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers having pendant luminescent groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during fabrication.

Various methods of OLED fabrication exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymeric OLEDs are manufactured by solution processes such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be fabricated by solution processes if the material can be dissolved or dispersed in a solvent.

The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.

US2016293853A1 discloses an organic compound having the following formula and an organic light emitting device comprising the compound:wherein G may be selected from the following structures:Wherein n is ₂ Selected from 0 or 1, when n ₂ When 0, L ³ Absence of; z is Z ¹ 、Z ² And Z ⁴ To Z ⁸ 、Z ¹⁷ To Z ³² Each independently selected from N and CR ₆ ；Ar ² Selected from aryl and heteroaryl. The application discloses in specific structures the following compounds: this application does not disclose and teach hexapenta-hexafused ring-dicarbazole compounds having specific substitutions and their impact on device performance.

CN112961145a discloses an organic compound having the following formula and an organic light emitting device comprising the compound:wherein X is O or S; z is Z ₁ -Z ₆ Identical or different, each independently CH or CR ₁ ；R ₁ Is a group represented by formula 2:And Z is ₁ -Z ₆ At least one of which contains a group represented by formula 2; r is R ₃ Is a C6-C30 aryl or a C5-C30 heteroaryl; r is R ₂ And R is ₄ The same or different, each independently is hydrogen, a C6-C30 aryl group or a C5-C30 heteroaryl group; l is a single bond or phenylene; y is Y ₁ -Y ₄ And is independently CH or CD. The application discloses in specific structures the following compounds:the application discloses compounds in which a dicarbazole structure is attached to a specific fused ring structure, andthe application of the organic light-emitting diode is in an organic light-emitting diode. This application does not disclose and teach hexapenta-hexafused ring-dicarbazole compounds having specific substitutions and their impact on device performance.

WO2018230860A1 discloses an organic light emitting device comprising an organic compound having the formula:wherein R is a substituted or unsubstituted C _6-60 An aryl group; cy has a fused ring structure as follows:A is the following structure fused to two adjacent rings:B has a ring structure as shown below:The following compounds are disclosed in this application:The application does not disclose and teach hexapenta-hexafused ring-dicarbazole compounds with specific substitutions and their impact on device performance.

WO2015178732A1 discloses an organic electroluminescent device in which the light-emitting layer comprises a first host compound having the formula:wherein X is O or S; ar (Ar) ₁ Represents a substituted or unsubstituted (C6-C30) aryl group; l (L) ₁ Represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group. The application discloses in specific structures the following compounds:The application does not disclose and teach hexapenta-hexafused ring-bicarbazoles with specific substitutionsCompounds and their effect on device performance.

WO2018174679A1 discloses an organic electroluminescent device wherein at least one organic layer comprises an organic compound having the formula:wherein N-Het is a substituted or unsubstituted mono-or polycyclic heterocyclic group containing at least one N; l is a direct bond, a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene; a is selected from integers from 1 to 3. The application discloses in specific structures the following compounds: / >This application does not disclose and teach the combination of hexapenta-hexafused ring-dicarbazole compounds having specific substitutions and their effect on device performance.

The currently reported bicarbazole organic semiconductor material has certain limitations on the carrier transmission capability and service life in photoelectric devices. Therefore, the application potential of the material is worth continuing to be deeply researched and developed.

Disclosure of Invention

The present invention aims to provide a series of compounds having the structure of formula 1 to solve at least part of the above problems. The compounds are useful in organic electroluminescent devices, for example, as host materials, transport materials, and the like. These novel compounds improve the electron and hole transport balance of the material and provide better device performance.

According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:

wherein,,

x is selected from O, S or Se;

X ₁ -X ₆ is selected from CR, identically or differently at each occurrence _x Or N;

U ₁ -U ₈ is selected identically or differently on each occurrence from C, CR _u Or N; wherein U is ₅ -U ₈ One of which is selected from C and is L ₁ Are connected;

V ₁ -V ₈ is selected identically or differently on each occurrence from C, CR _v Or N; wherein V is ₁ -V ₄ One of which is selected from C and is L ₁ Are connected;

R _y each occurrence, identically or differently, represents mono-, poly-or unsubstituted;

L ₁ And L ₂ Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, or a combination thereof;

R _x 、R _y 、R _u and R is _v And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms Germanium groups, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R _x Can optionally be linked to form a ring;

adjacent substituents R _y Can optionally be linked to form a ring;

adjacent substituents R _u And R is _v Can optionally be linked to form a ring.

According to another embodiment of the present invention, an organic electroluminescent device is disclosed, comprising an anode, a cathode, an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the compound of the previous embodiment.

According to yet another embodiment of the present invention, a compound composition comprising the compounds of the previous embodiments is also disclosed.

Disclosed is a novel compound having the structure of formula 1, which has a hexapenta-hexafused ring-bicarbazole skeleton and a substituted phenyl group at a specific position of the hexa-penta-hexafused ring group. The compound can be applied to an organic electroluminescent device, can improve the balance of electron and hole transmission, and provides better device performance, such as device efficiency improvement and device service life improvement.

Drawings

Fig. 1 is a schematic diagram of an organic light emitting device that may contain the compounds and compound compositions disclosed herein.

Fig. 2 is a schematic view of another organic light emitting device that may contain the compounds and compound compositions disclosed herein.

Detailed Description

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings may be omitted as desired. 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 may be fabricated by sequentially depositing the layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.

There are more instances 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 doped with F in a 50:1 molar ratio ₄ m-MTDATA of TCNQ as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Pat. 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 in 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. Examples of cathodes are disclosed in U.S. Pat. nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, including composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically 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, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

The above-described hierarchical structure is provided by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sublayers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.

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

The OLED also requires an encapsulation layer, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.

Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.

The materials and structures described herein may also be used in other organic electronic devices as listed above.

As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.

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.

A ligand may be referred to as "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.

It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.

Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe _S-T ). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally results in a small Δe _S-T . These states may include CT states. Typically, donor-acceptor hairThe optical material is constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

Definition of terms for substituents

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

Alkyl-as used herein, includes straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. 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, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

Cycloalkyl-as used herein, includes cyclic alkyl. Cycloalkyl groups may be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl are preferred. In addition, cycloalkyl groups may be optionally substituted.

Heteroalkyl-as used herein, a heteroalkyl comprises an alkyl chain in which one or more carbons is replaced by a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl. In addition, heteroalkyl groups may be optionally substituted.

Alkenyl-as used herein, covers straight chain, branched chain, and cyclic alkylene groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. In addition, alkenyl groups may be optionally substituted.

Alkynyl-as used herein, straight chain alkynyl is contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-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- (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-tetrabiphenyl. In addition, aryl groups may be optionally substituted.

Heterocyclyl or heterocycle-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. In addition, the heterocyclic group may be optionally substituted.

Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-boron, 1, 3-aza-boron, 1-aza-boron-4-aza, boron-doped compounds, and the like. In addition, heteroaryl groups may be optionally substituted.

Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.

Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenoxy. In addition, the aryloxy group may be optionally substituted.

Aralkyl-as used herein, encompasses aryl-substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. 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, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, cyano, o-cyanobenzyl, o-chlorobenzyl, 1-chlorophenyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, aralkyl groups may be optionally substituted.

Alkyl-as used herein, alkyl-substituted silicon groups are contemplated. The silyl group may be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of the alkyl silicon group include trimethyl silicon group, triethyl silicon group, methyldiethyl silicon group, ethyldimethyl silicon group, tripropyl silicon group, tributyl silicon group, triisopropyl silicon group, methyldiisopropyl silicon group, dimethylisopropyl silicon group, tri-t-butyl silicon group, triisobutyl silicon group, dimethyl-t-butyl silicon group, and methyldi-t-butyl silicon group. In addition, the alkyl silicon group may be optionally substituted.

Arylsilane-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenyl silyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, arylsilane groups may be optionally substituted.

Alkyl germanium group-as used herein, alkyl substituted germanium groups are contemplated. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkyl germanium groups include trimethyl germanium group, triethyl germanium group, methyl diethyl germanium group, ethyl dimethyl germanium group, tripropyl germanium group, tributyl germanium group, triisopropyl germanium group, methyl diisopropyl germanium group, dimethyl isopropyl germanium group, tri-t-butyl germanium group, triisobutyl germanium group, dimethyl-t-butyl germanium group, methyl-di-t-butyl germanium group. In addition, alkyl germanium groups may be optionally substituted.

Arylgermanium group-as used herein, encompasses at least one aryl or heteroaryl substituted germanium group. The arylgermanium group may be an arylgermanium group having 6-30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of aryl germanium groups include triphenylgermanium group, phenylbiphenyl germanium group, diphenylbiphenyl germanium group, phenyldiethyl germanium group, diphenylethyl germanium group, phenyldimethyl germanium group, diphenylmethyl germanium group, phenyldiisopropylgermanium group, diphenylisopropylgermanium group, diphenylbutylgermanium group, diphenylisobutylglycol group, and diphenyltert-butylgermanium group. In addition, the arylgermanium group may be optionally substituted.

The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.

In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, which may be substituted with one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted cycloalkyl having 1 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof.

It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may 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 specifying substituents or linking fragments are considered equivalent.

In the compounds mentioned in this disclosure, the 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. Substitution of other stable isotopes in the compounds may be preferred because of their enhanced efficiency and stability of the device.

In the compounds mentioned in this disclosure, multiple substitution is meant to encompass double substitution up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.

In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (including spiro, bridged, fused, etc.), as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

The expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that the two substituents bound to further distant carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

furthermore, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the adjacent two substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

wherein,,

x is selected from O, S or Se;

R _x 、R _y 、R _u and R is _v And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstitutedAn unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl 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 silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R _x Can optionally be linked to form a ring;

adjacent substituents R _y Can optionally be linked to form a ring;

adjacent substituents R _u And R is _v Can optionally be linked to form a ring.

Herein, "adjacent substituent R _x Can optionally be linked to form a ring ", intended to mean any two adjacent substituents R therein _x Can be connected to form a ring. Obviously, any adjacent R _x Neither may be connected to form a ring.

Herein, "adjacent substituent R _y Can optionally be linked to form a ring ", intended to mean any two adjacent substituents R therein _y Can be connected to form a ring. Obviously, any adjacent R _y Neither may be connected to form a ring.

Herein, "adjacent substituent R _u ，R _v Can optionally be linked to form a ring ", is intended to mean groups of adjacent substituents therein, e.g. two adjacent substituents R _u Between two adjacent substituents R _v Between, and adjacent substituents R _u And R is _v Between theseAny one or more of the substituent groups can be linked to form a ring. It will be apparent to those skilled in the art that none of these adjacent groups of substituents may be joined to form a ring.

According to one embodiment of the invention, wherein X is selected from O or S.

According to one embodiment of the invention, wherein X is O.

According to one embodiment of the invention, wherein X ₁ -X ₆ Is selected from CR, identically or differently at each occurrence _x 。

According to one embodiment of the invention, wherein U ₁ -U ₈ Is selected identically or differently on each occurrence from C or CR _u And U is as follows ₅ -U ₈ One of which is selected from C and is L ₁ Are connected.

According to one embodiment of the invention, wherein V ₁ -V ₈ Is selected identically or differently on each occurrence from C or CR _v And V is ₁ -V ₄ One of which is selected from C and is L ₁ Are connected.

According to one embodiment of the present invention, wherein the first compound has a structure represented by formula 1-a:

wherein,,

x is selected from O, S or Se;

U ₁ -U ₅ 、U ₇ and U ₈ Is selected from CR, identically or differently at each occurrence _u Or N;

V ₁ 、V ₂ and V ₄ -V ₈ Is selected from CR, identically or differently at each occurrence _v Or N;

L ₁ and L ₂ Each timeAnd are selected, identically or differently, from single bonds, substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof;

R _x 、R _y 、R _u and R is _v And is selected identically or differently on each occurrence 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 heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;

Adjacent substituents R _x Can optionally be linked to form a ring;

adjacent substituents R _y Can optionally be linked to form a ring;

adjacent substituents R _u And R is _v Can optionally be linked to form a ring.

According to one embodiment of the invention, wherein U ₁ -U ₈ Is selected identically or differently on each occurrence from C, CR _u Or N, and U ₁ -U ₈ At least one of which is selected from N, e.g. U ₁ -U ₈ One or both of which are selected from N.

According to one embodiment of the invention, wherein V ₁ -V ₈ Is selected identically or differently on each occurrence from C, CR _v Or N, and V ₁ -V ₈ At least one of which is selected from N, e.g. V ₁ -V ₈ One or both of which are selected from N.

According to one embodiment of the invention, wherein X ₁ -X ₆ Is selected from CR, identically or differently at each occurrence _x Or N, and X ₁ -X ₆ At least one of which is selected from N, e.g. X ₁ -X ₆ One or both of which are selected from N.

According to one embodiment of the invention, wherein Ar is identically or differently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the present invention, wherein Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, or a combination thereof.

According to one embodiment of the invention, wherein Ar is selected identically or differently on each occurrence from substituted or unsubstituted biphenyl.

According to one embodiment of the invention, wherein Ar is selected identically or differently on each occurrence from a substituted or unsubstituted meta-biphenyl.

According to one embodiment of the invention, wherein L ₁ And L ₂ The groups are selected, identically or differently, on each occurrence from single bonds, substituted or unsubstituted arylene groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.

According to one embodiment of the invention, wherein L ₁ And L ₂ Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a combination thereof.

According to one embodiment of the invention, wherein L ₁ And L ₂ And is selected identically or differently on each occurrence from a single bond, phenylene, biphenylene or naphthylene.

According to one embodiment of the invention, wherein R _u ，R _v ，R _x And R is _y And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein R _u ，R _v ，R _x And R is _y And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted aryl groups having from 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 20 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein R _u ，R _v ，R _x And R is _y And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, and combinations thereof.

According to one embodiment of the invention, wherein X ₁ -X ₃ Is selected from CR, identically or differently at each occurrence _x 。

According to one embodiment of the invention, wherein R _x And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted alkenyl having 3 to 20 carbon atoms, substituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted germyl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 carbon atoms, substituted or unsubstituted carbon atoms, having 6 to 20 carbon atoms.

According to one embodiment of the invention, wherein R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof.

According to one embodiment of the invention, wherein R _x And is selected identically or differently on each occurrence from hydrogen or deuterium.

According to an embodiment of the invention, wherein the compound is selected from the group consisting of compound a-1 to compound a-399, the specific structure of the compound a-1 to compound a-399 is seen in claim 10.

According to one embodiment of the present invention, wherein the hydrogen energy in the a-1 to a-399 structure is partially or fully replaced by deuterium.

According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising a compound as described in any of the embodiments above.

According to one embodiment of the invention, wherein the organic layer comprising the compound is a light emitting layer and the compound is a first host compound, the light emitting layer further comprises at least a first metal complex.

According to one embodiment of the invention, wherein the first metal complex has M (L _a ) _m (L _b ) _n (L _c ) _q Is of the general formula (I);

the metal M is selected from metals with relative atomic mass of more than 40;

L _a 、L _b and L _c A first ligand, a second ligand and a third ligand coordinated with the metal M, L _a 、L _b 、L _c May be the same or different;

L _a 、L _b and L _c Can optionally be linked to form a multidentate ligand;

m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of M, n, q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L _a May be the same or different; when n is 2, two L _b May be the same or different; when q is 2, two L _c May be the same or different;

ligand L _a Has a structure as shown in formula 2:

ring C ₁ And ring C ₂ The same or different at each occurrence is selected from a substituted or unsubstituted aromatic ring having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;

Q ₁ and Q ₂ Selected identically or differently on each occurrence from C or N;

R ₁ and R is ₂ Each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;

R ₁ and R is ₂ And is selected identically or differently on each occurrence 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 heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;

Adjacent substituents R ₁ 、R ₂ Can optionally be linked to form a ring;

ligand L _b And L _c The same or different at each occurrence is selected from monoanionic bidentate ligands.

In this embodiment, "adjacent substituent R ₁ 、R ₂ Can optionally be linked to form a ring ", is intended to mean groups of adjacent substituents therein, e.g., adjacent substituents R ₁ Between adjacent substituents R ₂ Between, and adjacent substituents R ₁ And R is ₂ In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not be all linked to form a ring。

According to one embodiment of the invention, wherein the ligand L _b And L _c And is selected identically or differently on each occurrence from the group consisting of:

wherein,,

R _a and R is _b Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;

X _b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR _N1 And CR (CR) _C1 R _C2 ；

X _c And X _d And is selected identically or differently on each occurrence from the group consisting of: o, S, se and NR _N2 ；

R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 to 20 carbon atoms An atomic arylsilyl group, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 Can optionally be linked to form a ring.

In this embodiment, "adjacent substituent R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 Can optionally be linked to form a ring ", is intended to mean groups of adjacent substituents therein, e.g. two adjacent substituents R _a Between two adjacent substituents R _b Between adjacent substituents R _a And R is _b Between adjacent substituents R _a And R is _c Between adjacent substituents R _b And R is _c Between adjacent substituents R _a And R is _N1 Between adjacent substituents R _b And R is _N1 Between adjacent substituents R _a And R is _C1 Between adjacent substituents R _a And R is _C2 Between adjacent substituents R _b And R is _C1 Between adjacent substituents R _b And R is _C2 Between adjacent substituents R _a And R is _N2 Between, and adjacent substituents R _b And R is _N2 In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.

According to one embodiment of the invention, wherein the metal M is selected, identically or differently, for each occurrence, from the group consisting of Cu, ag, au, ru, rh, pd, os, ir and Pt.

According to one embodiment of the invention, the metal M is chosen, identically or differently, for each occurrence, from Pt or Ir.

According to one embodiment of the inventionEmbodiments wherein the first metal complex has Ir (L _a ) _m (L _b ) _3-m And a structure represented by formula 3:

wherein,,

m is 0, 1, 2 or 3; when m is 2 or 3, a plurality of L _a The same or different; when m is 0 or 1, a plurality of L _b The same or different;

T ₁ -T ₆ each occurrence is identically or differently selected from CR _t Or N;

R _a 、R _b and R is _d Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;

R _a 、R _b 、R _d and R is _t And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxy, sulfinyl, sulfonyl, phosphino And combinations thereof;

adjacent substituents R _a ，R _b Can optionally be linked to form a ring;

adjacent substituents R _d ，R _t Can optionally be linked to form a ring.

In this embodiment, "adjacent substituent R _a ，R _b Can optionally be linked to form a ring ", is intended to mean groups of adjacent substituents therein, e.g. two adjacent substituents R _a Between two adjacent substituents R _b Between, and adjacent substituents R _a And R is _b In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.

In this embodiment, "adjacent substituent R _d ，R _t Can optionally be linked to form a ring ", is intended to mean groups of adjacent substituents therein, e.g. two adjacent substituents R _t Between two adjacent substituents R _d In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.

According to one embodiment of the invention, wherein T ₁ -T ₆ At least one of them is selected from CR _t And said R _t Selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to one embodiment of the invention, wherein T ₁ -T ₆ At least one of them is selected from CR _t And said R _t Is fluorine or cyano.

According to one embodiment of the invention, wherein T ₁ -T ₆ At least two of them are selected from CR _t And one of R _t Is fluoro or cyano, another R _t Selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted alkyl groups having 3 to 20 carbon atomsCycloalkyl of ring carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms.

According to one embodiment of the invention, wherein T ₁ -T ₆ Is selected from CR, identically or differently at each occurrence _t Or N, and T ₁ -T ₆ At least one of which is selected from N, e.g. T ₁ -T ₆ One or both of which are selected from N.

According to one embodiment of the invention, wherein the first metal complex is selected from the group consisting of:

according to an embodiment of the present invention, wherein the light emitting layer further comprises a second host compound having a structure represented by formula 4:

wherein,,

E ₁ -E ₆ is selected identically or differently on each occurrence from C, CR _e Or N, and E ₁ -E ₆ At least two of them are N, E ₁ -E ₆ At least one of which is C and is linked to formula 5;

Wherein,,

z is the same or different at each occurrence and is selected from the group consisting of O, S, se, N, NR ', CR ' R ', siR ' R ', geR ' R ' and R ' C=CR '; when two R's are present at the same time, the two R's may be the same or different;

p is 0 or 1, r is 0 or 1;

when Z is selected from N, p is 0, r is 1;

when Z is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ', geR ' R ' and R ' c=cr ', p is 1 and R is 0;

l is, identically or differently, selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Z ₁ -Z ₈ is selected identically or differently on each occurrence from C, CR _z Or N;

R _e r' and R _z And is selected, identically or differently, on each occurrence, 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 heterocyclyl having 3 to 20 ring 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 groups having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R _e ，R’，R _z Can optionally be linked to form a ring;

"onium" represents the position of the linkage of formula 4 with formula 5.

In this embodiment, "adjacent substituent R _e ，R’，R _z Can optionally be linked to form a ring ", is intended to mean groups of adjacent substituents therein, e.g., adjacent substituents R _e Between adjacent substituents R', between adjacent substituents R _z Between, and adjacent substituents R' and R _z In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.

According to one embodiment of the invention, wherein E ₁ -E ₆ Is selected identically or differently on each occurrence from C, CR _e Or N, and E ₁ -E ₆ Wherein three are N, E ₁ -E ₆ At least one is CR _e And said R _e And is selected identically or differently on each occurrence from the group consisting of: substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof;

and/or Z is selected identically or differently on each occurrence from O, S, N or NR';

and/orZ ₁ -Z ₈ At least one or at least two of them are selected from CR _z And said R _z Selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 5 to 30 carbon atoms, or combinations thereof;

and/or L is, identically or differently, selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein Z ₁ -Z ₈ Is selected identically or differently on each occurrence from C, CR _z Or N, and Z ₁ -Z ₈ At least one of which is selected from N, e.g. Z ₁ -Z ₈ One or both of which are selected from N.

According to one embodiment of the invention, wherein the second host compound is selected from the group consisting of:

according to one embodiment of the invention, the hydrogen energy in the H-1 to H-99 structures is partially or completely replaced by deuterium.

According to one embodiment of the present invention, the first metal complex is doped in the first host compound and the second host compound, and the weight of the first metal complex accounts for 1% -30% of the total weight of the light emitting layer.

According to one embodiment of the present invention, the first metal complex is doped in the first host compound and the second host compound, and the weight of the first metal complex is 3% -13% of the total weight of the light emitting layer.

According to one embodiment of the present invention, a compound composition is disclosed comprising a compound as described in any of the embodiments above.

Combined with other materials

The materials described herein for specific layers in an organic light emitting device may 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 2016/0359122A1, 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 may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

Materials described herein as useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

In the examples of material synthesis, all reactions were carried out under nitrogen protection, unless otherwise indicated. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bei Yi g sublimator, etc.), in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.

Material synthesis examples:

the preparation method of the compound of the present invention is not limited, and the following compounds are typically taken as examples, but not limited to, the synthetic route and preparation method are as follows:

synthesis example 1: synthesis of Compound A-1

Step 1: synthesis of intermediate B

In a 100mL three-necked round bottom flask, intermediate A (6.0 g,16.2 mmol) and CuBr were added ₂ (11.94 g,53.5 mmol), 1, 4-dioxane (20 mL), DMF (20 mL) and water (10 mL), with N ₂ Ventilation is performed three times, at N ₂ Under protection, heat reflux overnight. TLC plate confirmed the end of the reaction, stopped heating, cooled to room temperature, the reaction was filtered through celite, the filtrate concentrated under reduced pressure, and the crude product was chromatographed on silica gel (PE/dcm=50:1) to give intermediate B (3.5 g,10.8 mmol) as a white solid in 66.7% yield.

Step 2: synthesis of Compound A-1

In a 100mL three-necked round bottom flask, intermediate B (3.9 g,12.0 mmol), intermediate C (4.1 g,10.0 mmol), pd were charged ₂ (dba) ₃ (0.92 g,1.0 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl (S-phos, 0.41g,1.0 mmol), ^t BuONa (1.9 g,20.0 mmol) and xylene (50 mL), with N ₂ Ventilation is performed three times, at N ₂ Under protection, heat reflux overnight. TLC plate confirmed the end of the reaction, stopped heating, cooled to room temperature, the reaction was filtered through celite, the filtrate concentrated under reduced pressure, and the crude product was chromatographed on silica gel (PE/dcm=5:1) to give compound a-1 (4.0 g,6.2 mmol) as a white solid in 62.0% yield. The product was identified as the target product and had a molecular weight of 650.2.

Synthesis example 2: synthesis of Compound A-6

In a 100mL three-necked round bottom flask, was charged intermediate B (2.3 g,7.2 mmol), intermediate D (2.8 g,8.7 mmol), pd ₂ (dba) ₃ (0.66 g,0.7 mmol), 2-dicyclohexyl2',6' -dimethoxy-biphenyl (S-phos, 0.30g,0.7 mmol), ^t Buona (1.4 g,14.4 mmol) and xylene (40 mL), with N ₂ Ventilation is performed three times, at N ₂ Under protection, heat reflux overnight. TLC plate confirmed the end of the reaction, stopped heating, cooled to room temperature, the reaction was filtered through celite, the filtrate concentrated under reduced pressure, and the crude product was chromatographed on silica gel (PE/dcm=5:1) to give compound a-16 (3.4 g,4.7 mmol) as a white solid in 65.3% yield. The product was identified as the target product and had a molecular weight of 726.3.

Synthesis example 3: synthesis of Compound A-95

Step 1: synthesis of intermediate G

In a 250mL three-necked round bottom flask, intermediate E (8.0 g,22.9 mmol), intermediate F (5.9 g,29.7 mmol), pd (PPh) ₃ ) ₄ (1.3g,1.1mmol)、K ₂ CO ₃ (9.5 g,68.7 mmol), 1, 4-dioxane (100 mL), and H ₂ O (25 mL), nitrogen blanket, heat reflux overnight. Stopping heating, cooling to room temperature, separating, extracting the aqueous phase with DCM, mixing the organic phases, anhydrous Na ₂ SO ₄ Drying, filtering, and concentrating under reduced pressure. The crude product was chromatographed on silica gel (PE/dcm=15:1) to give intermediate G (7.0G, 19.7 mmol) as a white solid in 86.1% yield.

Step 2: synthesis of Compound A-95

In a 100mL three-necked round bottom flask, intermediate G (4.3G, 12.0 mmol), intermediate C (4.1G, 10.0 mmol), pd were added ₂ (dba) ₃ (0.92 g,1.0 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl (S-phos, 0.41g,1.0 mmol), ^t BuONa (1.9 g,20.0 mmol) and xylene (50 mL), with N ₂ Ventilation is performed three times, at N ₂ Under protection, heat reflux overnight. TLC plate confirmed the end of the reaction, stop addingThe reaction was cooled to room temperature, filtered through celite, and the filtrate concentrated under reduced pressure to give the crude product by silica gel column chromatography (PE/dcm=5:1) as a white solid compound a-95 (4.6 g,6.3 mmol) in 63.0% yield. The product was identified as the target product and had a molecular weight of 726.3.

Device embodiment

Example 1

First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was baked in a glove box to remove moisture. The substrate is then mounted on a substrate support and loaded into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 ^-8 In the case of the support, vapor deposition was sequentially performed on the ITO anode by thermal vacuum vapor deposition at a rate of 0.2 to 2 Angstrom/sec. The compound HI is used as a Hole Injection Layer (HIL). The compound HT serves as a Hole Transport Layer (HTL). Compound H1 acts as an Electron Blocking Layer (EBL). Then, the compound GD1 was doped in the compound H-1 and the compound A-1 of the present invention, and co-evaporation was used as an emitting layer (EML). Compound H2 was used as a Hole Blocking Layer (HBL). On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1nm was evaporated as an electron injection layer, and 120nm of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.

Example 2

The preparation of example 2 was the same as in example 1, except that compound A-6 was used in place of compound A-1 in the light-emitting layer (EML).

Comparative example 1

Comparative example 1 was prepared in the same manner as in example 1 except that compound C-1 was used in place of compound A-1 in the light-emitting layer (EML).

Comparative example 2

Comparative example 2 was prepared in the same manner as in example 1 except that compound C-2 was used in place of compound A-1 in the light-emitting layer (EML).

Comparative example 3

Comparative example 3 was prepared in the same manner as in example 1 except that compound C-3 was used in place of compound A-1 in the light-emitting layer (EML).

Comparative example 4

Comparative example 4 was prepared as in example 1, except that compound C-4 was used in place of compound A-1 in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.

Table 1 partial device structures of examples 1 to 2 and comparative examples 1 to 4

The material structure used in the device is as follows:

table 2 shows the results at 15mA/cm ² CIE data, driving voltage, external Quantum Efficiency (EQE), current Efficiency (CE), and Power Efficiency (PE) measured at constant current; at 80mA/cm ² Device lifetime measured at constant current (LT 95).

Table 2 device data for examples 1 to 2 and comparative examples 1 to 4

Discussion:

as can be seen from the data in table 2, the voltage of example 1 remains substantially comparable to that of comparative example 1, EQE is increased by 25.1%, CE is increased by 26.6%, PE is increased by 27.7%, and device lifetime is greatly increased by 3.40 times. The above results show that, in the compound having a hexapenta-hexafused ring-bicarbazole skeleton, compared with comparative example 1 in which the 9-position of the hexa-penta-hexafused ring group is a substituted triazinyl group, example 1 in which the 9-position of the hexa-penta-hexafused ring group is a phenyl substituent group of the present invention can greatly improve the efficiency (EQE, PE and CE) and lifetime of the device, and overall improve the overall performance of the device.

The device efficiency (EQE, PE and CE) of example 1 was improved compared to comparative example 2, and more importantly, example 1 was significantly improved by 337.5 times compared to comparative example 2 in terms of device lifetime. The above results indicate that, in the compound having a hexapenta-hexafused ring-bicarbazole skeleton, example 1 in which the 9-position of the hexapenta-hexafused ring group of the present invention is a phenyl substituent can greatly improve the device lifetime as compared with comparative example 2 in which the hexapenta-hexafused ring group is further fused with a phenyl group.

The voltage of example 1 was slightly reduced compared to comparative example 3, the device efficiency (EQE, PE and CE) remained substantially equivalent, but the device lifetime was improved by a factor of 1.88. The above results indicate that, in the compound having a hexapenta-hexafused ring-bicarbazole skeleton, example 1 in which the 9-position of the hexa-penta-hexafused ring group of the present invention is an aryl substituent can significantly improve the device lifetime as compared with comparative example 3 in which the hexa-penta-hexa-fused ring group is unsubstituted.

Compared to comparative example 4, the voltage of example 1 was reduced by 4.4%, EQE and CE remained substantially equivalent, PE increased by 5.2%, and device lifetime increased by 12%. The above results indicate that, in the compound having a hexapenta-hexafused ring-bicarbazole skeleton, example 1 in which the 9-position of the hexapenta-hexafused ring group of the present invention is a phenyl substituent can significantly improve the device lifetime as compared with comparative example 4 in which the 3-position of the hexapenta-hexafused ring group is a phenyl substituent.

From the above, it is understood that the compound A-1 of the present invention used in example 1 provides more excellent device performance, on the basis of which the compound structure is further improved, and the compound A-6 of the present invention used in example 2 having different substituents on the dicarbazole group is obtained, example 2 has the same excellent device efficiency (EQE, PE and CE) as in example 1, and on the basis of the higher device lifetime of example 1, the device lifetime of example 2 is further improved by 35.1%.

The above results show that the compound with specific substitution at specific positions of the hexakis-pentakis-hexafused ring-dicarbazole skeleton can improve the device performance, particularly remarkably prolong the service life of the device and finally improve the comprehensive performance of the device compared with the prior art with heteroaryl or fused structure at the specific positions, no substitution at the specific positions or aryl substitution at other substituted positions.

In conclusion, the compound disclosed by the invention is applied to an organic electroluminescent device, can improve the balance capacity of electron and hole transmission, improves the comprehensive performance of the device, particularly greatly prolongs the service life of the device, and has a wider application prospect.

It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.

Claims

1. A compound having a structure represented by formula 1:

wherein,,

x is selected from O, S or Se;

R _x 、R _y 、R _u and R is _v And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms An alkyl germanium group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl germanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R _x Can optionally be linked to form a ring;

adjacent substituents R _y Can optionally be linked to form a ring;

adjacent substituents R _u And R is _v Can optionally be linked to form a ring.

2. The compound of claim 1, wherein X is selected from O or S; preferably, X is O.

3. The compound of claim 1 or 2, wherein X ₁ -X ₆ Is selected from CR, identically or differently at each occurrence _x 。

4. A compound according to any one of claims 1 to 3 wherein U ₁ -U ₈ Is selected identically or differently on each occurrence from C or CR _u And U is as follows ₅ -U ₈ One of which is selected from C and is L ₁ Are connected; and/or V ₁ -V ₈ Is selected identically or differently on each occurrence from C or CR _v And V is ₁ -V ₄ One of which is selected from C and is L ₁ Are connected.

5. The compound of any one of claims 1-4, wherein U ₆ Selected from C and at L ₁ Are connected; and V is ₃ Selected from C and at L ₁ Are connected.

6. The compound of any one of claims 1-5, wherein Ar is, identically or differently, selected from a substituted or unsubstituted aryl group having 6-20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, or a combination thereof;

Preferably, ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, or a combination thereof.

7. The compound of any one of claims 1-6, wherein L ₁ And L ₂ Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

preferably L ₁ And L ₂ Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a combination thereof.

8. The compound of any one of claims 1-7, wherein R _u ，R _v ，R _x And R is _y And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;

Preferably, R _u ，R _v ，R _x And R is _y And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted aryl groups having from 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 20 carbon atoms, and combinations thereof.

9. The compound of any one of claims 1-8, wherein X ₁ -X ₃ Is selected from CR, identically or differently at each occurrence _x The method comprises the steps of carrying out a first treatment on the surface of the The R is _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof;

preferably, said R _x And is selected identically or differently on each occurrence from hydrogen or deuterium.

10. The compound of claim 1, wherein the compound is selected from the group consisting of:

optionally, the hydrogen energy in the a-1 to a-399 structures is partially or fully replaced by deuterium.

11. An organic electroluminescent device, comprising:

an anode is provided with a cathode,

a cathode electrode, which is arranged on the surface of the cathode,

an organic layer disposed between the anode and cathode, at least one of the organic layers comprising the compound of claims 1-10.

12. The organic electroluminescent device of claim 11, wherein the organic layer comprising the compound is a light-emitting layer, and the compound is a first host compound, the light-emitting layer further comprising at least a first metal complex.

13. The organic electroluminescent device of claim 12, wherein the first metal complex has M (L _a ) _m (L _b ) _n (L _c ) _q Is of the general formula (I);

the metal M is selected from metals with relative atomic mass of more than 40;

L _a 、L _b and L _c Can optionally be linked to form a multidentate ligand;

ligand L _a Has a structure as shown in formula 2:

R ₁ and R is ₂ And is selected identically or differently on each occurrence 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 heterocyclyl having 3 to 20 ring 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 aryl having 6 to 30 carbon atoms Alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

adjacent substituents R ₁ 、R ₂ Can optionally be linked to form a ring;

ligand L _b And L _c The same or different at each occurrence is selected from monoanionic bidentate ligands;

preferably, the ligand L _b And L _c And is selected identically or differently on each occurrence from the group consisting of:

wherein,,

R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstitutedSubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 0 to 20 carbon atoms, substituted or unsubstituted aminoyl having 0 to 20 carbon atoms, carbonyl, sulfonyl, cyano, sulfonyl, and combinations thereof;

14. The organic electroluminescent device of claim 12, wherein the light emitting layer further comprises a second host compound having a structure represented by formula 4:

wherein,,

p is 0 or 1, r is 0 or 1;

when Z is selected from N, p is 0, r is 1;

R _e r' and R _z And is selected, identically or differently, on each occurrence, 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 heterocyclyl having 3 to 20 ring 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 alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 3 to 20 carbon atomsAn alkyl germanium group of atoms, a substituted or unsubstituted aryl germanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

"onium" represents the position of the linkage of formula 4 with formula 5.

15. A compound composition comprising a compound of any one of claims 1-10.