Seven-membered fused boron-nitrogen heterocyclic compound and electroluminescent device comprising same

Abstract

The invention relates to a compound, an electroluminescent device comprising the same, a composition and a display assembly. The compound has a structure represented by a formula 1-1, a formula 1-2 or a formula 1-3. Formula 1-1, Formula 1-2, and Formula 1-3 are represented by the following structure: wherein X is selected from the group consisting of B, N, CRa, SiRa, P, P = O, or P = S at each occurrence; y1 and Y2, identical or different at each occurrence, are selected from the group consisting of a single bond, O, S, Se, NRN, BRM, CRaRb, or SiRaRb; z is selected from O, S, Se, NRN, CRaRb or SiRaRb at each occurrence. The composition comprises the compound, the compound can be used as a luminescent material in an electroluminescent device, and the device applying the compound has higher device efficiency, color purity and service life. # imgabs0 #

Description

Background Art

[0002] Technical Field Description Paragraph. Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (COPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LEGS), organic laser diodes, and organic plasmonic light emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced can include multiple layers, such as charge injection transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and Van Slyke is a fluorescent OLED. It uses only singlet states to emit light. The triplet states generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet emission from heavy metals containing complexes as emitters. Therefore, singlets and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet states to singlet states. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs based on the form of the material used. Small molecules refer to any organic or organometallic material that is not a polymer. The molecular weight of a small molecule can be large as long as it has a precise structure. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process. There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.

[0006] The luminescent color of OLED can be achieved by designing the structure of luminescent materials. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLED, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, pure organic small molecule OLED materials can also achieve full-color display of red, yellow, green and blue.

[0007] Although the current commercial OLED phosphorescent materials can achieve relatively high efficiency and lifespan, the emission spectra of these phosphorescent OLED materials have shoulder peaks, resulting in a wide half-peak width and low color purity. The spectrum of pure organic MR-TADF devices has a narrow half-peak width and high color purity, which can achieve a wider display color gamut. In addition, compared with phosphorescent materials containing precious metals, the production cost of pure organic TADF materials is lower. In addition, OLED devices are expected to have a more saturated emission spectrum, higher efficiency and longer lifespan.

[0008] CN105431439 discloses the following compound and an organic electroluminescent device comprising the compound: It further disclosed Further public The application focuses on the substituents on the boron nitrogen skeleton, and does not disclose the expansion method of the boron nitrogen π ring. The following two structures are disclosed in Adv.Opt.Mater.2022,10,2102513: There are two similar papers: Angew.Chem.Int.Ed.2022,61,e202209984; Chem.Commun.2023,59,2489-2492. These articles expand the boron nitrogen π ring to a five-membered ring. The six-membered boron nitrogen π ring is expanded in the following papers: Angew.Chem.Int.Ed.2020,59,17499-17503; Angew.Chem.Int.Ed.2023,62,202300934; Angew.Chem.Int.Ed.2022,61,e202204652; Angew.Chem.Int.Ed.2023,62,e202301930; Adv.Mater.2023,n / a,2305125.

[0009] The above prior arts do not disclose any example of extending the boron nitrogen π ring to a seven-membered ring. However, the seven-membered ring has a distinct difference in material properties from the five-membered and six-membered aromatic rings due to its unique spatial configuration.

[0010] These documents disclose some compounds containing boron-nitrogen heterocyclic skeletons, but the structures of these compounds still need to be further improved to obtain better device performance. Summary of the invention

[0011] Technical field description paragraph. The object of the present invention is to provide a compound and an electroluminescent device, composition and display assembly containing the same to solve the above problems. The compound can be used as a luminescent material in an electroluminescent device, can effectively improve the efficiency of the device, has better color purity and thermal stability, and can also provide better device stability.

[0012]

[0013] Ring A and Ring B are identically or differently selected from carbocyclic rings having 5 to 30 carbon atoms or heterocarbocyclic rings having 3 to 30 carbon atoms at each occurrence;

[0014] R X Each occurrence of the same or different means mono-, poly- or no-substitution;

[0015] Each time X appears, it is selected from B, N, CR a ,SiR a ,P,P=O or P=S;

[0016] Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CRa R b or SiR a R b ;

[0017] Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ;

[0018] R X ,R N ,R M ,R a ,R b ,R 1 To R 5 is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0019] Adjacent substituent R X , R N , R M , R a , R b , R 1 to R 5 They may optionally be linked to form a ring.

[0020] In some embodiments of the present invention, the compound has a structure represented by any one of Formula 1-1, Formula 2-1 and Formula 3-1, and Formula 1-1, Formula 2-1 and Formula 3-1 are represented as follows:

[0021]

[0022] in,

[0023] Ring A, Ring B, Ring C and Ring D are identically or differently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms at each occurrence;

[0024] R X Each occurrence of the same or different means mono-, poly- or no-substitution;

[0025] Each time X appears, it is selected from B, N, CR a ,SiR a ,P,P=O or P=S;

[0026] Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b ;

[0027] Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ;

[0028] R X ,R N ,R M ,R a ,R b and R 5is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0029] Adjacent substituent R X , R N , R M , R a , R b and R 5 They may optionally be linked to form a ring.

[0030] In some embodiments of the present invention, the ring A, ring B, ring C and ring D are selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms, the same or different when each occurs;

[0031] Preferably, the ring A, ring B, ring C and ring D are selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms, the same or different when each appears;

[0032] More preferably, the ring A, ring B, ring C and ring D are selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring, the same or different when they appear each time.

[0033] In some embodiments of the present invention, the compound has a structure represented by any one of Formula 1-2, Formula 2-2 and Formula 3-2, and Formula 1-2, Formula 2-2 and Formula 3-2 are represented as:

[0034]

[0035] in,

[0036] A 1 To A 8Each occurrence is selected from N or CR, either identically or differently X ;

[0037] Each time X appears, it is selected from B, N, CR a ,SiR a ,P,P=O or P=S;

[0038] Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b ;

[0039] Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ;

[0040] R X ,R N ,R M ,R a ,R b and R 5 is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0041] Adjacent substituent R X ,R N ,R M ,R a ,Rb and R 5 They may optionally be linked to form a ring.

[0042] In some embodiments of the present invention, a compound according to claim 1-3 is characterized in that each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ;

[0043] Preferably, each occurrence of Z is selected from O, S, Se, NR N ;

[0044] More preferably, each occurrence of Z is selected from NR N .

[0045] In some embodiments of the present invention, the compound has a structure represented by any one of Formula 1-3-1 to Formula 1-3-5, Formula 2-3-1 to Formula 2-3-5, Formula 3-3-1 to Formula 3-3-3, and Formula 1-3-1 to Formula 1-3-5, Formula 2-3-1 to Formula 2-3-5, Formula 3-3-1 to Formula 3-3-3 are represented as:

[0046]

[0047] in,

[0048] Each occurrence of W is selected from O, S, SO, SO2, Se, NR N ,BR M ,CR a R b ,C=O or SiR a R b ;

[0049] Preferably, each occurrence of W is selected from O, S, Se, NR N ,BR M ,CR a R b ,C=O or SiR a R b ;

[0050] More preferably, W at each occurrence is selected from O, S, Se, NR N ,CR a R b or SiR a R b ;

[0051] R X ,R N ,RM ,R a and R b is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0052] Adjacent substituent R X ,R N ,R M ,R a and R b They may optionally be linked to form a ring.

[0053] In some embodiments of the present invention, the Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b ;

[0054] Preferably, Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,CR a R b or SiR a R b ;

[0055] More preferably, Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N.

[0056] In some embodiments of the present invention, the compound is selected from the following structures and the group consisting thereof: structures corresponding to compound numbers C1 to C281, structures obtained after hydrogen in any structure corresponding to compound numbers C1 to C281 is partially or completely replaced by deuterium, and combinations thereof; the structures represented by compound numbers C1 to C281 are respectively selected from the following structures:

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068] In a second aspect, the present invention further provides an electroluminescent device, comprising:

[0069] anode,

[0070] cathode,

[0071] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises any one of the compounds described above.

[0072] In some embodiments of the present invention, the organic layer is a light-emitting layer, and the compound is a light-emitting material.

[0073] In some embodiments of the present invention, one or more of the organic layers are formed by a deposition method or a solution method.

[0074] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122M, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0075] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273M, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0076] In a third aspect, the present invention also provides a composition comprising the compound as described above.

[0077] In a fourth aspect, the present invention further provides a display assembly comprising the electroluminescent device as described above.

[0078] The display components described in the present invention include, but are not limited to, flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays and taillights.

[0079] The compounds of the present invention can be used as the main material in the electroluminescent device. These compounds have an electron transport unit of imidazole, pyrimidine, quinazoline, quinoxaline, azabenzodithiophene, azabenzodifuran, azabenzodiselenophene, azatriphenylene, triazine and similar structures, and a hole transport unit having an indolepyrrole fused aza macrocyclic structure connected to the electron transport unit by a specific position. The molecular structure design in which the hole transport unit and the electron transport unit are connected by a specific position gives these compound molecules a special spatial structure, bringing unexpected effects, so that this new type of compound has a significantly reduced evaporation temperature, has better thermal stability, and can effectively reduce energy consumption, is more conducive to the device manufacturing process, and can effectively improve the device efficiency and provide better device performance.

[0080] It should be noted that in the above technical solution, the definitions of the substituent terms are as follows:

[0081] Halogens or halides: include fluorine, chlorine, bromine and iodine.

[0082] Alkyl: Contains straight chain and branched chain alkyl. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isobutyl, 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. In addition, the alkyl group may be optionally substituted. 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.

[0083] Cycloalkyl: Contains cyclic alkyl. The cycloalkyl may be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl may be optionally substituted.

[0084] Assorted alkyl: Assorted alkyl comprises that one or more carbons in alkyl chain are substituted by heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminoindole, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisoindole, tert-butyldimethylsilyl, triethylsilyl, triisoindole, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisoindole. In addition, assorted alkyl can be optionally substituted.

[0085] Alkenyl: includes straight chain, branched chain and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexenyl, cyclohexatenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0086] Alkynyl: straight chain alkynyl is included. The alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, the alkynyl may be optionally substituted.

[0087] Aryl or aromatic group: Both 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, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, biphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.

[0088] Heterocyclic group or heterocycle: non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. In addition, the heterocyclic group may be optionally substituted.

[0089] Heteroaryl: A non-fused and fused heteroaromatic group containing 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoxazole, benzothiazole, quinoline, isoxazole, benzofuran, benzothi ...furan, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran Quinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and aza analogs thereof. In addition, the heteroaryl group may be optionally substituted.

[0090] Alkoxy: represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclic. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclic are the same as above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy may be optionally substituted.

[0091] Aryloxy: represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy may be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy may be optionally substituted.

[0092] Aralkyl: an alkyl group containing aryl substitution. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 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, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0093] Alkylsilyl: Silicon groups substituted with alkyl groups. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methylditert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0094] Arylsilyl: silicon radical containing at least one aryl substitution. The arylsilyl can be an arylsilyl having 6 to 30 carbon atoms, preferably an arylsilyl having 8 to 20 carbon atoms. Examples of arylsilyl include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tritert-butylsilyl, dimethyltert-butylsilyl, methylditert-butylsilyl. In addition, the arylsilyl can be optionally substituted.

[0095] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0096] It should be noted that in the above technical scheme, unless otherwise defined, when any one of the terms in the group consisting of the following is used, 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 amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be replaced by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms. The invention also includes an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclyl group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an 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.

[0097] It should be noted that, in the compounds of the present invention, when a molecular fragment is described as a substituent or otherwise connected to another part, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or connecting fragments are considered equivalent.

[0098] It should be noted that in the compounds of the present invention, 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. Due to its enhanced efficiency and stability of the device, the replacement of other stable isotopes in the compound may be preferred.

[0099] It should be noted that in the compounds of the present invention, multiple substitution refers to the range including disubstitution up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.

[0100] It should be noted that, in the compounds of the present invention, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0101] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken 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:

[0102]

[0103] The expression that adjacent substituents can be optionally 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:

[0104]

[0105] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other 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:

[0106]

[0107] Adjacent substituents R, R can be optionally connected to form a ring, which is intended to indicate that adjacent substituents R can be optionally connected to form a ring, and also intended to indicate that when there are multiple R on the ring 1 X When the adjacent substituent R X can be optionally connected to form a ring, and is also intended to mean that when there are multiple R X When the adjacent substituent R X can be optionally connected to form a ring, and is also intended to mean that when there are multiple R X When the adjacent substituent R X can be optionally linked to form a ring, and is also intended to represent adjacent substituents R and R X can be optionally connected to form a ring; it is obvious to those skilled in the art that adjacent substituents R, R X Alternatively, they may not be connected to form a ring. In this case, adjacent substituents R are not connected to form a ring, and / or adjacent substituents R X nor are they connected to form a ring, and / or adjacent substituents R and R X They also do not connect to form a ring.

[0108] In this context, adjacent substituents R a ,R b , which can be optionally connected to form a ring, is intended to indicate that when there is a substituent R a ,R b When the adjacent substituent groups, such as the substituent R a With R b Any one or more of the groups can be linked to form a ring. Obviously, when there is a substituent R a ,R b When the adjacent substituent groups are not connected to form a ring. BRIEF DESCRIPTION OF THE DRAWINGS

[0109] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulation compositions disclosed herein.

[0110] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulation compositions disclosed herein.

[0111] Figures 3 to 18 are the H-NMR and C-NMR spectra of the compounds disclosed herein. DETAILED DESCRIPTION

[0112] The following examples are used to illustrate the present invention but are not intended to limit the scope of the present invention.

[0113] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure can be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0114] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. Examples of cathodes include composite cathodes having a thin layer of metal, such as Mg:Ag, and an overlying transparent, conductive, sputter-deposited ITO layer, as disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety. 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 injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated by reference in its entirety.

[0115] The above layered structure is provided by way of non-limiting example. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be omitted completely. It can also include other layers that are not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, the light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0116] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.

[0117] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0118] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0119] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in a liquid medium 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 property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photosensitive property of the emissive material, but the ancillary ligand may modify the properties of the photosensitive ligand.

[0120] The internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0121] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0122] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE ST ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE ST These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0123] The technical scheme of the present invention is described in detail below through specific examples. The following examples are used to illustrate the present invention, but are not used to limit the scope of the present invention. Any other equivalent changes or modifications completed without departing from the spirit disclosed by the present invention should be included in the scope of the claims.

[0124] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Agilent's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to the evaporation machine produced by Suzhou Fangsheng, the optical test system and life test system produced by Suzhou Fushida, the ellipsometer produced by Beijing Liangtuo, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents will not be elaborated in this patent.

[0125] Material synthesis example:

[0126] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0127]

[0128] Synthesis Example 1: Synthesis of Compound C82

[0129] Step 1: Synthesis of intermediate C82-A

[0130]

[0131] In a dry 2L two-necked flask, diphenylamine (100g, 1.0eq), sodium tert-butoxide (114g, 2.0eq), palladium acetate (663mg, 0.5%) and tri-tert-butylphosphine tetrafluoroborate (2.14g, 1.25%) were added in sequence. After replacing nitrogen three times, o-bromoiodobenzene (200g, 1.2eq) and toluene 500mL were added, and the mixture was heated to reflux for overnight reaction. After the reaction was completed, the mixture was cooled to room temperature, and appropriate amount of water and ethyl acetate were added for extraction. The organic phase was separated, dried over anhydrous magnesium sulfate, concentrated, and subjected to column chromatography to obtain white solid C82-A (180g, yield 94%).

[0132] Step 2: Synthesis of intermediate C82-B

[0133]

[0134] In a dry 1L two-necked flask, C82-A (52g, 1.0eq) was added in sequence. After replacing nitrogen three times, 500mL of ultra-dry tetrahydrofuran was added, the temperature was lowered to -78°C, and then n-butyl lithium (1.6M, 110mL, 1.1eq) was added dropwise. The reaction was continued for 1h at this temperature, and then triisopropyl borate (56mL, 1.5eq) was added dropwise, and the temperature was slowly raised to room temperature. An appropriate amount of dilute hydrochloric acid was added, and stirring was continued for 1h. After monitoring the reaction by thin layer chromatography (TLC), an appropriate amount of ethyl acetate was added for extraction, and the organic phase was separated and concentrated to an appropriate volume. Petroleum ether was added for pulping to obtain a white solid C82-B (37g, yield 80%).

[0135] Step 3: Synthesis of intermediate C82-C

[0136]

[0137] In a dry 1L two-necked flask, C82-B (15g, 1.0eq), 2,4-difluoro-6-bromoiodobenzene (16.54g, 1.0eq), potassium carbonate (17.9g, 2.5eq) and tetrakistriphenylphosphine palladium (600mg, 1%) were added in sequence. After replacing nitrogen three times, 300mL of tetrahydrofuran and 150mL of water were added, heated to reflux, and reacted overnight. After the reaction was completed, the temperature was cooled to room temperature, and an appropriate amount of ethyl acetate was added for extraction, and the organic phase was separated, dried over anhydrous magnesium sulfate, concentrated, and column chromatography was performed to obtain a white solid C82-C (12.5g, yield 55%).

[0138] Step 4: Synthesis of intermediate C82-D

[0139]

[0140] In a dry 500mL two-necked flask, C82-C (12g, 1.0eq), potassium carbonate (11.4g, 3eq), palladium acetate (123mg, 2%) and tri-tert-butylphosphine tetrafluoroborate (400mg, 5%) were added in sequence, and after replacing nitrogen three times, 200mL of N,N-dimethylacetamide was added, heated to reflux, and reacted overnight. After the reaction was completed, the temperature was cooled to room temperature, and an appropriate amount of ethyl acetate was added for extraction, and the organic phase was separated, dried over anhydrous magnesium sulfate, concentrated, and column chromatography was performed to obtain a white solid C82-D (7.9g, yield 80%).

[0141] Step 5: Synthesis of intermediate C82-E

[0142]

[0143] In a dry 500mL two-necked flask, add C82-D (6g, 1.0eq) to replace nitrogen three times, then add 100mL of ultra-dry tetrahydrofuran, cool to -78°C, then drop n-butyl lithium (2.5M, 8mL, 1.2eq), continue to react at this temperature for 2h, then drop bromine (5.4g, 2.0eq), slowly warm to room temperature. After the reaction is completed, monitor by thin layer chromatography (TLC), cool to room temperature, add saturated sodium sulfite solution, extract with appropriate amount of ethyl acetate, separate the organic phase, dry with anhydrous magnesium sulfate, concentrate and column chromatography to obtain off-white solid C82-E (6.6g, yield 90%).

[0144] Step 6: Synthesis of intermediate C82-F

[0145]

[0146] In a dry 250mL two-necked flask, add C82-E (5g, 1.0eq), 3,6-di-tert-butylcarbazole (8.05g, 2.5eq) and cesium carbonate (18.76g, 5eq), replace nitrogen three times, add 50mL of N,N-dimethylacetamide, heat to reflux, and react overnight. After the reaction is completed, monitor the reaction by thin layer chromatography (TLC), cool to room temperature, add an appropriate volume of water, precipitate a large amount of white solid, filter out the crude product, heat and beat with 50mL of methanol twice, cool to room temperature and filter out the off-white product C82-F (9g, yield 82%).

[0147] Step 7: Synthesis of intermediate C82

[0148]

[0149] In a dry 250mL two-necked flask, add C82-F (5g, 1.0eq), replace nitrogen three times, add 100mL of ultra-dry xylene, cool to -30°C, then drop n-butyl lithium (2.5M, 2.5mL, 1.2eq), warm to room temperature for 2h, then cool to -30°C, add boron tribromide (0.75mL, 1.5eq), warm to room temperature for 2h, then cool to 0°C, add diisopropylethylamine (1.85mL, 2.0eq), warm to 130°C for overnight reaction. After the reaction is completed, monitor the reaction by thin layer chromatography (TLC), cool to room temperature, filter the reaction solution with diatomaceous earth, concentrate the filtrate and column chromatograph to obtain yellow solid C82 (2g, yield 43%).

[0150] Synthesis Example 2: Synthesis of Compound C87

[0151] Step 1: Synthesis of intermediate C87-A

[0152]

[0153] In a dry 1L two-necked flask, carbazole (30g, 1.0eq) and cesium carbonate (146g, 2.5eq) were added in sequence, nitrogen was replaced three times, then o-fluorobromobenzene (47g, 1.5eq) and 350mL of N,N-dimethylacetamide were added, heated to reflux, and reacted overnight. After the reaction was completed, the temperature was cooled to room temperature, and an appropriate volume of water was added to precipitate a large amount of white solid, and the crude product was filtered out and the intermediate C87-A (52g, yield 90%) was obtained by column chromatography.

[0154] Step 2: Synthesis of intermediate C87-B

[0155]

[0156] In a dry 1L two-necked flask, C87-A (30g, 1.0eq) was added in sequence. After replacing nitrogen three times, 200mL of ultra-dry tetrahydrofuran was added, the temperature was lowered to -78°C, and then n-butyl lithium (1.6M, 64mL, 1.1eq) was added dropwise. The reaction was continued for 1h at this temperature, and then triisopropyl borate (33mL, 1.5eq) was added dropwise, and the temperature was slowly raised to room temperature. An appropriate amount of dilute hydrochloric acid was added, and stirring was continued for 1h. After monitoring the reaction by thin layer chromatography (TLC), an appropriate amount of ethyl acetate was added for extraction, and the organic phase was separated and concentrated to an appropriate volume. Petroleum ether was added for pulping to obtain a white solid C87-B (23g, yield 86%).

[0157] Step 3: Synthesis of intermediate C87-C

[0158]

[0159] In a dry 1L two-necked flask, C87-B (15g, 1.0eq), 2,4-difluoro-6-bromoiodobenzene (20g, 1.2eq), potassium carbonate (18g, 2.5eq) and tetrakistriphenylphosphine palladium (604mg, 1%) were added in sequence. After replacing nitrogen three times, 300mL of tetrahydrofuran and 150mL of water were added, heated to reflux, and reacted overnight. After the reaction was completed, the temperature was lowered to room temperature, and an appropriate amount of ethyl acetate was added for extraction, and the organic phase was separated, dried over anhydrous magnesium sulfate, concentrated, and column chromatography was performed to obtain a white solid C87-C (18.8g, yield 83%).

[0160] Step 4: Synthesis of intermediate C87-D

[0161]

[0162] In a dry 500mL two-necked flask, C82-C (12g, 1.0eq), potassium carbonate (11.5g, 3eq), palladium acetate (125mg, 2%) and tri-tert-butylphosphine tetrafluoroborate (400mg, 5%) were added in sequence, and after replacing nitrogen three times, 200mL of N,N-dimethylacetamide was added, heated to reflux, and reacted overnight. After the reaction was completed, the temperature was cooled to room temperature, and an appropriate amount of ethyl acetate was added for extraction, and the organic phase was separated, dried over anhydrous magnesium sulfate, concentrated, and column chromatography was performed to obtain a white solid C87-D (8g, yield 82%).

[0163] Step 5: Synthesis of intermediate C87-E

[0164]

[0165] In a dry 500mL two-necked flask, add C87-D (20g, 1.0eq) to replace nitrogen three times, then add 200mL of ultra-dry tetrahydrofuran, cool to -78°C, then drop n-butyl lithium (2.5M, 27.2mL, 1.2eq), continue to react at this temperature for 2h, then drop bromine (18g, 2.0eq), slowly warm to room temperature. After the reaction is completed, monitor by thin layer chromatography (TLC), cool to room temperature, add saturated sodium sulfite solution, extract with appropriate amount of ethyl acetate, separate the organic phase, dry with anhydrous magnesium sulfate, concentrate and column chromatography to obtain off-white solid C87-E (20g, yield 82%).

[0166] Step 6: Synthesis of intermediate C87-F

[0167]

[0168] In a dry 250mL two-necked flask, add C87-E (5g, 1.0eq), 3,6-di-tert-butylcarbazole (8.1g, 2.5eq) and cesium carbonate (19g, 5eq), replace nitrogen three times, add 50mL of N,N-dimethylacetamide, heat to reflux, and react overnight. After the reaction is completed, monitor the reaction by thin layer chromatography (TLC), cool to room temperature, add an appropriate volume of water, precipitate a large amount of white solid, filter out the crude product, heat and slurry with 50mL of methanol twice, cool to room temperature and filter out the off-white product C87-F (9.35g, yield 85%).

[0169] Step 7: Synthesis of intermediate C87

[0170]

[0171] In a dry 250mL two-necked flask, add C87-F (5g, 1.0eq), replace nitrogen three times, add 100mL of ultra-dry xylene, cool to -30°C, then drop n-butyl lithium (2.5M, 2.5mL, 1.2eq), warm to room temperature for 2h, then cool to -30°C, add boron tribromide (0.75mL, 1.5eq), warm to room temperature for 2h, then cool to 0°C, add diisopropylethylamine (1.85mL, 2.0eq), warm to 130°C for overnight reaction. After the reaction is completed, monitor the reaction by thin layer chromatography (TLC), cool to room temperature, filter the reaction solution with diatomaceous earth, concentrate the filtrate and column chromatograph to obtain yellow solid C87 (2.8g, yield 60%).

[0172] Synthesis Example 3: Synthesis of Compound C92

[0173] The specific synthesis steps refer to the synthesis of compound C87. In the third step, 1-bromo-2-chloro-3,5-difluorobenzene is used to replace 2,4-difluoro-6-bromoiodobenzene. The other steps are the same to obtain compound C92.

[0174] Synthesis Example 4: Synthesis of Compound C107

[0175] The specific synthesis steps refer to the synthesis of compound C82, and phenothiazine is used to replace diphenylamine in the first step. The other steps are the same, and compound C107 can be obtained.

[0176] Synthesis Example 5: Synthesis of Compound C112

[0177] The specific synthesis steps refer to the synthesis of compound C107, and 1-bromo-2-chloro-3,5-difluorobenzene is used to replace 2,4-difluoro-6-bromoiodobenzene in the third step. The other steps are the same, and compound C112 can be obtained.

[0178] Synthesis Example 6: Synthesis of Compound C117

[0179] The specific synthesis steps refer to the synthesis of compound C107, and phenothiazine is replaced by phenothiazine in the first step. The other steps are the same, and compound C117 can be obtained.

[0180] Synthesis Example 7: Synthesis of Compound C122

[0181] The specific synthesis steps refer to the synthesis of compound C112, and phenothiazine is replaced by phenothiazine in the first step. The other steps are the same, and compound C122 can be obtained.

[0182] Synthesis Example 8: Synthesis of Compound C243

[0183] The specific synthesis steps refer to the synthesis of compound C92, and 3,6-di-tert-butylcarbazole is used instead of carbazole in the first step. The other steps are the same, and compound C243 can be obtained.

[0184] Synthesis Example 9: Synthesis of Compound C244

[0185] The specific synthesis steps refer to the synthesis of compound C87, and 3,6-di-tert-butylcarbazole is used instead of carbazole in the first step. The other steps are the same, and compound C244 can be obtained.

[0186] Synthesis Example 10: Synthesis of Compound C245

[0187] The specific synthesis steps refer to the synthesis of compound C87. In the first step, 10H-benzofurano[3,2-B]indole is used instead of carbazole. The other steps are the same to obtain compound C245.

[0188] Device Example 1:

[0189] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 Torr's case The ITO anode was deposited sequentially by thermal vacuum deposition at a rate of . At the same time, the deposited compounds HT and NDP-9 were used as hole injection layers (HIL) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then GH-P, GH-N and the compound C82 of the present invention as a dopant were co-evaporated to form an emitting layer (EML) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL) with a thickness of Finally, evaporation 8-Hydroxyquinoline-lithium (Liq) was used as an electron injection layer (EIL) and evaporated The device is then transferred back to the glove box and encapsulated with a glass lid to complete the device. The material structure used in the device is shown below:

[0190]

[0191] Device Example 2:

[0192] The implementation of Device Example 2 is the same as that of Device Example 1, except that the present compound C87 is used as the host in the emissive layer (EML) instead of the present compound C82.

[0193] Device Example 3:

[0194] The implementation of Device Example 2 is the same as that of Device Example 1, except that the inventive compound C92 is used as the host in the emissive layer (EML) instead of the inventive compound C82.

[0195] Device Example 4:

[0196] The implementation of Device Example 2 is the same as that of Device Example 1, except that the inventive compound C107 is used as the host in the emissive layer (EML) instead of the inventive compound C82.

[0197] Device Example 5:

[0198] The implementation of Device Example 2 is the same as that of Device Example 1, except that the present compound C112 is used as the host in the emissive layer (EML) instead of the present compound C82.

[0199] Device Example 6:

[0200] The implementation of Device Example 2 is the same as that of Device Example 1, except that the present compound C117 is used as the host in the emissive layer (EML) instead of the present compound C82.

[0201] Device Example 7:

[0202] The implementation of Device Example 2 is the same as that of Device Example 1, except that the present compound C122 is used as the host in the emissive layer (EML) instead of the present compound C82.

[0203] Device Example 8:

[0204] The implementation of Device Example 2 is the same as that of Device Example 1, except that the inventive compound C244 is used as the host in the emissive layer (EML) instead of the inventive compound C82.

[0205] Device Example 9:

[0206] The implementation of Device Example 2 is the same as that of Device Example 1, except that the inventive compound C243 is used as the host in the emissive layer (EML) instead of the inventive compound C82.

[0207] Device Example 10:

[0208] The implementation of Device Example 2 is the same as that of Device Example 1, except that the inventive compound C245 is used as the host in the emissive layer (EML) instead of the inventive compound C82.

[0209] The detailed device layer structures and thicknesses of device embodiments 1 to 10 are shown in Table 1. The layers using more than one material are obtained by doping different compounds in the recorded weight ratio.

[0210] Table 1 Device structures of device embodiments and comparative examples

[0211]

[0212] Table 2 lists the 2 Under these conditions, the maximum wavelength (λ max ) and external quantum efficiency (EQE).

[0213] Table 2 Device data:

[0214]

[0215]

[0216] discuss:

[0217] As shown in Table 2, the compound of the present invention has a 1000 cd / m 2 The external quantum efficiency (EQE) measured under the conditions is higher than that of the compound AZA-BN disclosed in the literature (Angew. Chem. Int. Ed. 2020, 59, 17499-17503.). AZA-BN has a 1000 cd / m 2 The external quantum efficiency (EQE) measured under the conditions was 19.1%. By expanding the boron nitrogen mother core to a seven-membered ring or a seven-membered heterocyclic ring, on the one hand, the emission wavelength can be red-shifted to 525nm, and the CIE y can reach 0.76, which is very close to the green light standard displayed by BT.2020. On the other hand, due to the spatial stereo configuration of the seven-membered ring or the seven-membered heterocyclic ring, and the higher triplet energy level, this type of compound has a smaller ΔE ST , thus having a faster intersystem crossing rate and showing higher efficiency on the device. Device Example 9 has an initial brightness of 6500cd / m 2 , LT measured at constant current 90 The initial brightness of the AZA-BN phosphorescent device is 100 h, which is much higher than that of the AZA-BN compound disclosed in the literature (AZA-BN phosphorescent sensitizer, with an initial brightness of 2000 cd / m 2 , device life LT 90 The above data demonstrate the unique advantages of the compounds of the present invention.

[0218] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

[0219] Although the present invention has been described in detail above with general descriptions and specific embodiments, it is obvious to those skilled in the art that some modifications or improvements may be made thereto based on the present invention. Therefore, these modifications or improvements made without departing from the spirit of the present invention all fall within the scope of protection claimed by the present invention.

Claims

1. A compound, characterized in that The compound has a structure represented by any one of Formula 1, Formula 2 and Formula 3, and Formula 1, Formula 2 and Formula 3 are represented as follows: Ring A and Ring B are identically or differently selected from carbocyclic rings having 5 to 30 carbon atoms or heterocarbocyclic rings having 3 to 30 carbon atoms at each occurrence; R X Each occurrence of the same or different means mono-, poly- or no-substitution; Each time X appears, it is selected from B, N, CR a ,SiR a ,P,P=O or P=S; Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b ; Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ; R X ,R N ,R M ,R a ,R b ,R 1 To R 5 is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R X , R N , R M , R a , R b , R 1 To R 5 They may optionally be linked to form a ring.

2. A compound according to claim 1, characterized in that The compound has a structure represented by any one of Formula 1-1, Formula 2-1 and Formula 3-1, and Formula 1-1, Formula 2-1 and Formula 3-1 are represented by: in, Ring A, Ring B, Ring C and Ring D are identically or differently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms at each occurrence; R X Each occurrence of the same or different means mono-, poly- or no-substitution; Each time X appears, it is selected from B, N, CR a ,SiR a ,P,P=O or P=S; Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b ; Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ; R X ,R N ,R M ,R a ,R b and R 5 is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R X , R N , R M , R a , R b and R 5 They may optionally be linked to form a ring.

3. A compound according to claim 1 or 2, characterized in that The ring A, ring B, ring C and ring D are selected from 5-membered unsaturated carbocyclic rings, aromatic rings with 6 to 30 carbon atoms, or heteroaromatic rings with 3 to 30 carbon atoms, the same or different when they appear each time; Preferably, the ring A, ring B, ring C and ring D are selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms, the same or different when each appears; More preferably, the ring A, ring B, ring C and ring D are selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring, the same or different when they appear each time.

4. A compound according to claims 1 to 3, characterized in that The compound has a structure represented by any one of Formula 1-2, Formula 2-2 and Formula 3-2, and Formula 1-2, Formula 2-2 and Formula 3-2 are represented by: in, A 1 To A 8 Each occurrence is selected from N or CR, either identically or differently X ; Each time X appears, it is selected from B, N, CR a ,SiR a ,P,P=O or P=S; Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b ; Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ; R X ,R N ,R M ,R a ,R b and R 5 is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R X ,R N ,R M ,R a ,R b and R 5 They may optionally be linked to form a ring.

5. A compound according to claims 1 to 4, characterized in that Each occurrence of Z is selected from O, S, Se, NR N ,CR a R b or SiR a R b ; Preferably, each occurrence of Z is selected from O, S, Se, NR N ; More preferably, each occurrence of Z is selected from NR N .

6. A compound according to claims 1 to 5, characterized in that The compound has a structure represented by any one of Formula 1-3-1 to Formula 1-3-5, Formula 2-3-1 to Formula 2-3-5, Formula 3-3-1 to Formula 3-3-3, and Formula 1-3-1 to Formula 1-3-5, Formula 2-3-1 to Formula 2-3-5, Formula 3-3-1 to Formula 3-3-3 are represented by: in, Each occurrence of W is selected from O, S, SO, SO2, Se, NR N ,BR M ,CR a R b ,C=O or SiR a R b ; Preferably, each occurrence of W is selected from O, S, Se, NR N ,BR M ,CR a R b ,C=O or SiR a R b ; More preferably, W at each occurrence is selected from O, S, Se, NR N ,CR a R b or SiR a R b ; R X ,R N ,R M ,R a and R b is selected, at each occurrence, identically or differently, 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 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R X ,R N ,R M ,R a and R b They may optionally be linked to form a ring.

7. A compound according to any one of claims 1 to 6, characterized in that The Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,BR M ,CR a R b or SiR a R b Preferably, Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N ,CR a R b or SiR a R b ; More preferably, Y 1 and Y 2 Each occurrence is identically or differently selected from the group consisting of: single bond, O, S, Se, NR N .

8. A compound according to any one of claims 1 to 7, characterized in that The compound is selected from the following structures and the group consisting of them: structures corresponding to compound numbers C1 to C281, structures obtained after hydrogen in any structure corresponding to compound numbers C1 to C281 is partially or completely replaced by deuterium, and combinations thereof; the structures represented by compound numbers C1 to C281 are respectively selected from the following structures:

9. An electroluminescent device, characterized in that: include: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 8.

10. An electroluminescent device according to claim 9, characterized in that: The organic layer is a light-emitting layer, and the compound is a light-emitting material.

11. An electroluminescent device according to claim 9, characterized in that: One or more of the organic layers are formed by a deposition method or a solution method.

12. A composition, characterized in that Comprising the compound as claimed in any one of claims 1 to 8.

13. A display component, characterized in that: Comprising the electroluminescent device according to any one of claims 9 to 12.

Images