An organic compound and use thereof

Abstract

This invention relates to an organic compound and its applications, the organic compound having an H-L-Ar structure, wherein H has a structure represented by Formula 1-1 or Formula 1-2; Formula 1-1 and Formula 1-2 are represented as follows: In Formula 1-1 and Formula 1-2, A 1 and A 2 Each occurrence of Z is selected from N or CR, either identically or differently; each occurrence of Z is selected from O, S, Se, NR. N ,CR a R b or SiR a R b This organic compound can be used as the main material in electroluminescent devices, exhibiting better thermal stability and effectively reducing energy consumption, which is more beneficial to the device fabrication process. In addition, it can effectively improve device efficiency and provide better device performance.

Description

Technical Field

[0001] This invention relates to organic electroluminescent compounds and organic electroluminescent devices comprising the same. More particularly, it relates to a compound formed by bonding an indole-pyrrole fused nitrogen macrocycle to an aryl or heteroaryl group, and organic electroluminescent devices and combinations thereof comprising the compound. Background Technology

[0002] 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 (OLETs), organic photovoltaic devices (COPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-effect devices (OFQDs), luminescent electrochemical cells (LEGS), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline aluminum layer as the electron transport layer and the light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as a charge injection transport layer, a charge and exciton blocking layer, and one or more light-emitting layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and Van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet 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 small singlet-triple state gaps, making it possible for excitons to return from the doublet state to the singlet state. 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 OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing. Various OLED manufacturing methods exist. Small-molecule OLEDs are typically manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods such as spin coating, inkjet printing, and nozzle printing. Small-molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0006] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Phosphorescent materials have been successfully commercialized for green, yellow, and red OLEDs. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0007] However, many of the reported host materials still have room for improvement. For example, WO2018021841A1 discloses an organic electroluminescent compound and an organic electroluminescent device including the organic electroluminescent compound, which includes an organic layer containing one or more hosts. The structure of the organic light-emitting compound in the first host is as follows:

[0008]

[0009] However, the compound X it disclosed... 10 To X 13 Each can be represented independently as N or CR, indicating that the formed ring is a 6-membered ring. Furthermore, the current efficiency of the disclosed organic electroluminescent devices is relatively low. Therefore, in order to meet the industry's ever-increasing demands, especially for higher device efficiency and longer device lifespan, new materials still require further research and development. Summary of the Invention

[0010] The purpose of this invention is to provide a compound and electroluminescent devices, compositions and display components containing the same to solve the above problems. The compound can be used as a host material in electroluminescent devices, has better thermal stability, can effectively reduce energy consumption, is more conducive to the device manufacturing process, and can also effectively improve device efficiency and provide better device performance.

[0011] In a first aspect, the present invention provides a compound having an HL-Ar structure, wherein H has a structure represented by formula 1-1 or formula 1-2;

[0012] Equations 1-1 and 1-2 are expressed as follows:

[0013]

[0014] In Formulas 1-1 and 1-2, ring 1, ring 2 and ring 3 are selected from carbon rings having 5-18 carbon atoms or heterocarbon rings having 3-18 carbon atoms each time they appear;

[0015] R X Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0016] A 1 and A 2 Each occurrence is either identical or different and is selected from N or CR;

[0017] Z is selected from O, S, Se, NR each time it appears. N ,CR a R b and SiR a R b ;

[0018] Each time L appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0019] Ar,R,R X ,R N ,Ra and R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, 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, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0020] Adjacent substituents R,R X ,R a and R b Optional connections form a loop;

[0021] The asterisk (*) indicates the location where the L bond is formed.

[0022] In some embodiments of the present invention, the rings 1, 2 and 3 are selected from 5-membered carbon rings, aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms each time they appear.

[0023] Preferably, the rings 1, 2, and 3 are selected from 5-membered carbon rings, benzene rings, 5-membered heteroaromatic rings, or 6-membered heteroaromatic rings each time they appear.

[0024] In some embodiments of the present invention, the H is selected each time it appears from a structure represented by formulas 2-1 to 2-8:

[0025]

[0026] in,

[0027] X 1 To X 9 Each occurrence is either identically or differently selected from N or CR X ;

[0028] Each time Z and Y appear, choose freely from O, S, Se, NR. N ,CR a Rb and SiR a R b A group that is formed.

[0029] In some embodiments of the present invention, R,R X ,R N ,R a and R b Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl 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 amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0030] Preferably, R,R X ,R N ,R a and R b At least one of them is selected from deuterium, substituted or unsubstituted aryl group having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl group having 3-30 carbon atoms;

[0031] More preferably, R,R X ,R N ,R a and R b At least one of them is selected from deuterium, phenyl, biphenyl, naphthyl or pyridyl.

[0032] Based on the synthetic routes shown in Equations 2-1 and 2-2, the synthesis of Equations 2-3 to 2-8 can be achieved by changing the substrate.

[0033] In some embodiments of the present invention, A 1 and A 2 The substituents R are optionally linked to form a carbon ring having 5-18 carbon atoms, or a heterocarbon ring having 3-18 carbon atoms;

[0034] Preferably, A 1 and A 2 The substituents R are optionally linked to form an aromatic ring having a 5-membered carbon ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms;

[0035] More preferably, A 1 and A 2 The substituents R are optionally linked to form a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, furan ring, thiophene ring, fluorene ring, silylfluorene ring, and combinations thereof.

[0036] In some embodiments of the present invention, the structure of H is one of the structures shown in H-1 to H-280, or a structure obtained by partially or completely replacing hydrogen with deuterium in any of the structures shown in H-1 to H-280; wherein the structures corresponding to H-1 to H-280 are as follows:

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047] In some embodiments of the present invention, the L is selected from the group consisting of: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted furanylene, substituted or unsubstituted thiopheneylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and combinations thereof;

[0048] Preferably, the L is selected from the group consisting of the following structures each time it appears: single bond, phenylene, naphthylene, biphenylene, terphenylene, pyridylene, pyrimidinylene, pyrazinylene, furanylene, thiopheneylene, dibenzofuranylene, dibenzothiopheneylene, and combinations thereof;

[0049] More preferably, each occurrence of L is selected from the following structures and their combinations: structures numbered L-0 to L-50, structures obtained by partially or completely replacing hydrogen in any of the structures numbered L-0 to L-50 with deuterium, and combinations thereof;

[0050] The structures corresponding to numbers L-0 to L-50 are:

[0051]

[0052]

[0053] In the structures numbered L-0 to L-50, "*" indicates the position where the structure is bonded to the H shown in Equation 1-1 or Equation 1-2. Indicates the location where the structure is bonded to Ar.

[0054] In some embodiments of the invention, the Ar is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-10 carbon atoms, substituted or unsubstituted... The substituted aryloxy group having 6-20 carbon atoms, the substituted or unsubstituted alkenyl group having 2-10 carbon atoms, the substituted or unsubstituted alkynyl group having 2-10 carbon atoms, the substituted or unsubstituted aryl group having 6-20 carbon atoms, the substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, the substituted or unsubstituted alksilyl group having 3-10 carbon atoms, the substituted or unsubstituted arylsilyl group having 6-10 carbon atoms, the substituted or unsubstituted amino group having 0-10 carbon atoms, and combinations thereof.

[0055] Preferably, Ar is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted Substituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted benzopyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl.

[0056] In some embodiments of the present invention, the Ar is selected each time it appears from the following structures and groups thereof: structures numbered Ar-1 to Ar-106, structures obtained by partially or completely replacing hydrogen in any of the structures numbered Ar-1 to Ar-106 with deuterium, and combinations thereof;

[0057] The structures corresponding to numbers Ar-1 to Ar-106 are:

[0058]

[0059]

[0060]

[0061]

[0062] In some embodiments of the present invention, the compound has an HL-Ar structure, wherein H is selected from the group consisting of structures numbered H-1 to H-280, L is selected from the group consisting of structures numbered L-0 to L-50, and Ar is selected from the group consisting of structures numbered Ar-1 to Ar-106.

[0063] Alternatively, the compound has an HL-Ar structure, wherein H is selected from the group consisting of structures numbered H-1 to H-280, L is selected from the group consisting of structures numbered L-0 to L-50, and Ar is selected from the group consisting of structures numbered Ar-1 to Ar-106, wherein the structures corresponding to H-1 to H-280 are as described above, the structures corresponding to L-0 to L-50 are as described above, and the structures corresponding to Ar-1 to Ar-106 are as described above, and optionally, the hydrogen in the compound is partially or completely substituted with deuterium.

[0064] In some embodiments of the present invention, the compound is selected from the group consisting of the following structures and their components: the structures corresponding to compound numbers C1 to C1688, the structures obtained by partially or completely replacing hydrogen in any of the structures corresponding to compound numbers C1 to C1688 with deuterium, and combinations thereof; the structures represented by compound numbers C1 to C1688 have an HL-Ar structure, wherein H, L, and Ar correspond to the following respectively:

[0065] Compounds numbered C1 to C280, L is L-0, Ar is Ar-1, and H corresponds to H-1 to H-280 respectively;

[0066] Compounds numbered C281 to C560 all have L-0, Ar all have Ar-24, and H correspond to H-1 to H-280 respectively.

[0067] Compounds numbered C561 to C840 all have L-1, Ar all have Ar-97, and H correspond to H-1 to H-280 respectively.

[0068] Compound numbers C842 to C946 (excluding compound number C864) all have L-0, H all have H-6, and Ar correspond to Ar-2 to Ar-106 (excluding Ar-24) respectively.

[0069] Compound numbers C948 to C1052 (excluding compound number C970) all have L-0, H all have H-7, and Ar correspond to Ar-2 to Ar-106 (excluding Ar-24) respectively.

[0070] Compound numbers C1054 to C1158 (excluding compound number C1076) all have L-0, H all have H-16, and Ar correspond to Ar-2 to Ar-106 (excluding Ar-24) respectively.

[0071] Compound numbers C1160 to C1264 (excluding compound number C1182) all have L-0, H all have H-17, and Ar correspond to Ar-2 to Ar-106 (excluding Ar-24) respectively.

[0072] Compound numbers C1265 to C1370 (excluding compound number C1361) all have L-1, H all have H-6, and Ar correspond to Ar-1 to Ar-106 (excluding Ar-97).

[0073] Compound numbers C1371 to C1476 (excluding compound number C1467) all have L-1, H all have H-7, and Ar correspond to Ar-1 to Ar-106 (excluding Ar-97) respectively.

[0074] Compound numbers C1477 to C1582 (excluding compound number C1573) all have L-1, H all have H-16, and Ar correspond to Ar-1 to Ar-106 (excluding Ar-97).

[0075] Compound numbers C1583 to C1688 (excluding compound number C1679) all have L-1, H all have H-17, and Ar correspond to Ar-1 to Ar-106 (excluding Ar-97) respectively.

[0076] The compound numbers and corresponding structures of the compounds whose structures are not specified are shown in the table below:

[0077] Compound numbering H L Ar C841 H-6 L-2 Ar-1 C864 H-6 L-2 Ar-24 C947 H-7 L-2 Ar-1 C970 H-7 L-2 Ar-24 C1053 H-16 L-2 Ar-1 C1076 H-16 L-2 Ar-24 C1159 H-17 L-2 Ar-1 C1182 H-17 L-2 Ar-24 C1361 H-6 L-32 Ar-97 C1467 H-7 L-32 Ar-97 C1573 H-16 L-32 Ar-97 C1679 H-17 L-32 Ar-97

[0078] In a second aspect, the present invention also provides an electroluminescent device, comprising:

[0079] Anode, cathode

[0080] And an organic layer disposed between the anode and the cathode, the organic layer comprising the compounds described above.

[0081] In some embodiments of the present invention, the organic layer is a light-emitting layer, and the compound is the host material.

[0082] In some embodiments of the present invention, the light-emitting layer further comprises at least one phosphorescent material.

[0083] Thirdly, the present invention also provides a composition comprising the compound as described above.

[0084] Fourthly, the present invention also provides a display component comprising the electroluminescent device as described above.

[0085] The display components described in this invention include, but are not limited to, flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0086] It should be noted that the definitions of substituent terms in the above technical solutions are as follows:

[0087] Halogens: including fluorine, chlorine, bromine and iodine.

[0088] Alkyl group: Includes straight-chain and branched alkyl groups. The alkyl group can 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, isolaryl, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Additionally, the alkyl group may optionally be substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0089] Cycloalkyl: Contains cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups 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, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0090] Heteroalkyl: A heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and 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, aminolactone, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisolactone, tert-butyldimethylsilyl, triethylsilyl, triisolactone, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisolactone. Additionally, the heteroalkyl group may optionally be substituted.

[0091] Alkenyl: Includes straight-chain, branched, and cyclic olefin groups. Alkenyl groups can be those containing 2 to 20 carbon atoms, preferably those 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, cycloheptenyl, cycloheptanetrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0092] Alkynyl group: Contains a straight-chain alkynyl group. The alkynyl group can 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, propynyl, 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, propynyl, butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group can be optionally substituted.

[0093] Aryl or aromatic group: Consider both non-fused and fused systems. The aryl group can 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, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may optionally be substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 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-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0094] Heterocyclic groups or heterocycles: Consider non-aromatic cyclic groups. 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, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. 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 ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acrylidine, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazine, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. Additionally, the heterocyclic group may optionally be substituted.

[0095] Heteroaryl: A non-fused and fused heteroaryl group comprising 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. Isoaryl also refers to heteroaryl. Heteroaryl can 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, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, iso Quinoline, cyclophosphine, quinazolin, quinoxaline, naphthidine, phthalazine, pteridine, guarbenzine, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0096] Alkoxy group: represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can 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, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy group may optionally be substituted.

[0097] Aryloxy group: 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 can 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 biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0098] Aryl group: An alkyl group comprising an aryl group. The aryl group can be an aryl group having 7 to 30 carbon atoms, preferably an aryl group having 7 to 20 carbon atoms, and more preferably an aryl group having 7 to 13 carbon atoms. Examples of aryl groups 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 The compounds include alkyl groups, such as 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-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0099] Alkylsilyl: A silyl group comprising alkyl substitution. The alkylsilyl group can 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, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0100] Arylsilyl group: comprising at least one aryl-substituted silane group. The arylsilyl group can be an arylsilyl group having 6-30 carbon atoms, preferably an arylsilyl group having 8-20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tri-tert-butylsilyl, dimethyltert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the arylsilyl group may optionally be substituted.

[0101] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic fragment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0102] It should be noted that, in the above technical solutions, unless otherwise defined, when any one of the following groups is used, substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alksilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphinyl, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alksilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl, which can be one or more groups selected from deuterium, halogen, and unsubstituted alkane having 1-20 carbon atoms. The group includes unsubstituted cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, unsubstituted arylyl groups having 6-30 carbon atoms, unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.

[0103] It should be noted that, in the compounds of this invention, when a molecular fragment is described as a substituent or otherwise linked to another part, its name may 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 designating substituents or linking fragments are considered equivalent.

[0104] It should be noted that in the compounds of this invention, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to its ability to enhance device efficiency and stability.

[0105] It should be noted that in the compounds of this invention, multiple substitution refers to the range including disubstituted substitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this invention represents multiple substitution (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can exist at multiple available substitution positions on its linkage structure. The substituent existing at multiple available substitution positions can be of the same structure or different structures.

[0106] It should be noted that in the compounds of the present invention, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in the present invention, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring, and can be an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0107] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0108]

[0109] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0110]

[0111] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent bonds at the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0112]

[0113] Adjacent substituents R can optionally connect to form a ring, which is intended to indicate that adjacent substituents R can optionally connect to form a ring, and also to indicate that when there are multiple R on ring 1. X When, the adjacent substituent R X The loop can be arbitrarily connected to form a ring, which also indicates that when there are multiple Rs on ring 2... X When, the adjacent substituent R X The loop can be arbitrarily connected to form a ring, which also indicates that when there are multiple Rs on ring 3. X When, the adjacent substituent R X The elements can be optionally linked to form a ring, and are also intended to represent adjacent substituents R and R'. X They can be optionally linked to form a ring; obviously, to those skilled in the art, adjacent substituents R,R X Alternatively, they may not connect to form a ring. In this case, adjacent substituents R do not connect to form a ring, and / or adjacent substituents R X It also does not connect to form a ring, and / or adjacent substituents R and R X They also do not connect to form a loop.

[0114] In this paper, adjacent substituents R a ,R b They can be optionally linked to form a ring, intended to indicate the presence of substituent R. a ,R b When, adjacent substituent groups, such as substituent R a With R b One or more of them can connect to form a ring. It is obvious that when a substituent R is present... a ,R b In this case, adjacent substituent groups may not be connected to form a ring.

[0115] The compounds of this invention can be used as host materials in electroluminescent devices. These compounds have electron transport units with structures of imidazole, pyrimidine, quinazoline, quinoxaline, azinondithiophene, azinondifuran, azinondiselenophene, azinontriphenylene, triazine, and similar structures, as well as hole transport units with indole-pyrrole fused azinon macrocyclic structures connected to the electron transport units at specific positions. This molecular structure design, where hole and electron transport units are connected at specific positions, gives these compound molecules a unique spatial structure, resulting in unexpected effects. These novel compounds can effectively reduce energy consumption, are more conducive to device fabrication, and further improve device efficiency, providing better device performance. Detailed Implementation

[0116] The following examples are used to illustrate the present invention, but are not intended to limit the scope of the invention.

[0117] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including, but not limited to, Agilent liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters, fluorescence spectrophotometers, electrochemical workstations, sublimation apparatuses, etc.) in a manner well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional equipment in the art in a manner well known to those skilled in the art. Since those skilled in the art are familiar with the use of the aforementioned equipment, testing methods, and other related matters, and can obtain the inherent data of the samples definitively and unaffected, the aforementioned related matters will not be elaborated upon in this patent.

[0118] The compounds in this invention can be prepared according to one of the synthetic routes 1 to 4. During the preparation of the compounds, the corresponding raw materials are selected according to the corresponding synthetic route based on the different structures of the compounds. The process parameters during the preparation process can be appropriately adjusted according to the specific product to be obtained, but without affecting the entire synthetic route.

[0119] Synthesis Route 1:

[0120]

[0121] Reference for the synthesis of IM1-2: Shan XH, Yang B, Qu JP, et al. CuSO4-Catalyzeddual annulation to synthesize O,S or N-containing tetracyclic heteroacenes[J]. Chemical Communications, 2020, 56(29):4063-4066.

[0122] Synthesis of IM1-3:

[0123] In a dry round-bottom flask under nitrogen protection, IM1-2, S1-3, cesium carbonate, and N,N-dimethylacetamide were added sequentially, and the mixture was heated to 150°C to react. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate to separate the organic phase, dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate, IM1-3.

[0124] Synthesis of IM1-4:

[0125] In a dry round-bottom flask under nitrogen protection, IM1-3 and ultra-dry tetrahydrofuran were added sequentially, the temperature was lowered to -78°C, and then n-butyllithium was added dropwise. The reaction was continued at this temperature for 1 hour, then triisopropyl borate was added, the temperature was slowly raised to room temperature, and the reaction was allowed to proceed overnight. Then, an appropriate amount of dilute hydrochloric acid was added, and the mixture was stirred for another hour. Then, an appropriate amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with an appropriate amount of n-heptane. The mixture was filtered to obtain a milky white solid intermediate, IM1-4.

[0126] Synthesis of IM1-5:

[0127] In a dry round-bottom flask, IM1-4, S1-4, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Toluene, ethanol, and water were then added under nitrogen protection, and the mixture was heated to 95°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and then separated by column chromatography to obtain a yellow solid intermediate, IM1-5.

[0128] Synthesis of IM1-6:

[0129] In a dry round-bottom flask under nitrogen protection, IM1-5, cesium carbonate, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and xylene were added sequentially, and the mixture was heated to 150°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and the diatomaceous earth was washed with an appropriate amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate, IM1-6.

[0130] Synthesis of IM1-7:

[0131] In a dry round-bottom flask under nitrogen protection, IM1-6, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM1-7 was obtained by column chromatography.

[0132] Synthesis Route 2:

[0133]

[0134] Synthesis of IM2-1:

[0135] In a dry round-bottom flask, S2-1, S2-2, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Under nitrogen protection, tetrahydrofuran and water were added, and the mixture was refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid, IM2-1.

[0136] Synthesis of IM2-2:

[0137] In a dry round-bottom flask under nitrogen protection, IM2-1, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 6 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM2-2 was obtained by column chromatography.

[0138] Synthesis of IM2-3:

[0139] In a dry round-bottom flask under nitrogen protection, IM2-2, S2-3, cesium carbonate, and N,N-dimethylacetamide were added sequentially, and the mixture was heated to 150°C and reacted for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate to separate the organic phase, dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate, IM2-3.

[0140] Synthesis of IM2-4:

[0141] In a dry round-bottom flask under nitrogen protection, IM2-3 and ultra-dry tetrahydrofuran were added sequentially, the temperature was lowered to -78°C, and then n-butyllithium was added dropwise. The reaction was continued at this temperature for 1 hour, then triisopropyl borate was added, the temperature was slowly raised to room temperature, and the reaction was allowed to proceed overnight. Then, an appropriate amount of dilute hydrochloric acid was added, and the mixture was stirred for another 1 hour. Then, an appropriate amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with an appropriate amount of n-heptane. The mixture was filtered to obtain a milky white solid intermediate, IM2-4.

[0142] Synthesis of IM2-5:

[0143] In a dry round-bottom flask, IM2-4, S2-4, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Toluene, ethanol, and water were then added under nitrogen protection, and the mixture was heated to 95°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and then separated by column chromatography to obtain a yellow solid intermediate, IM2-5.

[0144] Synthesis of IM2-6:

[0145] In a dry round-bottom flask under nitrogen protection, IM2-5, cesium carbonate, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and xylene were added sequentially, and the mixture was heated to 150°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and the diatomaceous earth was washed with an appropriate amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate, IM2-6.

[0146] Synthesis of IM2-7:

[0147] In a dry round-bottom flask under nitrogen protection, IM2-6, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM2-7 was obtained by column chromatography.

[0148] Synthesis Route 3:

[0149]

[0150] Synthesis of IM3-1:

[0151] In a dry round-bottom flask, S3-1, S3-2, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Under nitrogen protection, tetrahydrofuran and water were added, and the mixture was refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid, IM3-1.

[0152] Synthesis of IM3-2:

[0153] In a dry round-bottom flask under nitrogen protection, IM3-1, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 6 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM3-2 was obtained by column chromatography.

[0154] Synthesis of IM3-3:

[0155] In a dry round-bottom flask under nitrogen protection, IM3-2, S3-3, cesium carbonate, and N,N-dimethylacetamide were added sequentially, and the mixture was heated to 150°C and reacted for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate to separate the organic phase, dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate, IM3-3.

[0156] Synthesis of IM3-4:

[0157] In a dry round-bottom flask under nitrogen protection, IM3-3 and ultra-dry tetrahydrofuran were added sequentially, the temperature was lowered to -78°C, and then n-butyllithium was added dropwise. The reaction was continued at this temperature for 1 hour, then triisopropyl borate was added, the temperature was slowly raised to room temperature, and the reaction was allowed to proceed overnight. Then, an appropriate amount of dilute hydrochloric acid was added, and the mixture was stirred for another 1 hour. Then, an appropriate amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with an appropriate amount of n-heptane. The mixture was filtered to obtain a milky white solid intermediate, IM3-4.

[0158] Synthesis of IM3-5:

[0159] In a dry round-bottom flask, IM3-4, S3-4, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Toluene, ethanol, and water were then added under nitrogen protection, and the mixture was heated to 95°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and then separated by column chromatography to obtain a yellow solid intermediate, IM3-5.

[0160] Synthesis of IM3-6:

[0161] In a dry round-bottom flask under nitrogen protection, IM3-5, cesium carbonate, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and xylene were added sequentially, and the mixture was heated to 150°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and the diatomaceous earth was washed with an appropriate amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate, IM3-6.

[0162] Synthesis of IM3-7:

[0163] In a dry round-bottom flask under nitrogen protection, IM3-6, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM2-7 was obtained by column chromatography.

[0164] Synthesis Route 4:

[0165]

[0166] Synthesis of IM4-1:

[0167] In a dry round-bottom flask, S4-1, S4-2, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Under nitrogen protection, tetrahydrofuran and water were added, and the mixture was refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid, IM4-1.

[0168] Synthesis of IM4-2:

[0169] In a dry round-bottom flask under nitrogen protection, IM4-1, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 6 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM4-2 was obtained by column chromatography.

[0170] Synthesis of IM4-3:

[0171] In a dry round-bottom flask under nitrogen protection, IM4-2, S4-3, cesium carbonate, and N,N-dimethylacetamide were added sequentially, and the mixture was heated to 150°C and reacted for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, a suitable amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate, IM4-3.

[0172] Synthesis of IM4-4:

[0173] In a dry round-bottom flask under nitrogen protection, IM4-3 and ultra-dry tetrahydrofuran were added sequentially, the temperature was lowered to -78°C, and then n-butyllithium was added dropwise. The reaction was continued at this temperature for 1 hour, then triisopropyl borate was added, the temperature was slowly raised to room temperature, and the reaction was allowed to proceed overnight. Then, an appropriate amount of dilute hydrochloric acid was added, and the mixture was stirred for another 1 hour. Then, an appropriate amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with an appropriate amount of n-heptane. The mixture was filtered to obtain a milky white solid intermediate, IM4-4.

[0174] Synthesis of IM4-5:

[0175] In a dry round-bottom flask, IM4-4, S4-4, potassium carbonate, and tetraphenylphosphine palladium were added sequentially, purging with nitrogen three times. Toluene, ethanol, and water were then added under nitrogen protection, and the mixture was heated to 95°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and then separated by column chromatography to obtain a yellow solid intermediate, IM4-5.

[0176] Synthesis of IM4-6:

[0177] In a dry round-bottom flask under nitrogen protection, IM4-5, cesium carbonate, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and xylene were added sequentially, and the mixture was heated to 150°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and the diatomaceous earth was washed with an appropriate amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate, IM4-6.

[0178] Synthesis of IM4-7:

[0179] In a dry round-bottom flask under nitrogen protection, IM4-6, triphenylphosphine, and o-dichlorobenzene were added sequentially, and the mixture was heated to 150°C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the yellow solid intermediate IM4-7 was obtained by column chromatography.

[0180] Material synthesis examples:

[0181] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0182] Synthesis Example 1: Synthesis of Compound C566

[0183] Step 1: Synthesis of C566-IM-1

[0184]

[0185] In a 2L dry round-bottom flask, SM2 (40g, 1.0eq, 336.78mmol), potassium carbonate (139.3g, 3.0eq, 1010.34mmol), and N,N-dimethylformamide (500mL) were added sequentially. The mixture was reacted at room temperature for 10 minutes, followed by the addition of SM1 (100g, 1.0eq, 336.78mmol), and the reaction was continued at room temperature for 20 hours. After the reaction was complete, an appropriate amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate C566-IM-1 (107g, 95% yield).

[0186] Step 2: Synthesis of C566-IM-2

[0187]

[0188] In a dry 2L round-bottom flask, potassium tert-butoxide (14.73 g, 2.2 eq, 131.3 mmol), C566-IM-1 (20 g, 1.0 eq, 59.68 mmol), and copper sulfate (476 mg, 0.05 eq, 2.98 mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 1.2 L of chlorobenzene was added, and the reaction was carried out at 90 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and washed with an appropriate amount of ethyl acetate. The filtrate was concentrated and separated by column chromatography to obtain a white solid intermediate, C566-IM-2 (12 g, 98% yield).

[0189] Step 3: Synthesis of C566-IM-3

[0190]

[0191] In a 1 L dry round-bottom flask under nitrogen protection, C566-IM-2 (10 g, 1.0 eq, 48.26 mmol), SM3 (8.45 g, 1.0 eq, 48.26 mmol), cesium carbonate (47.17 g, 3.0 eq, 48.26 mmol), and 300 mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 140 °C and reacted for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate C566-IM-3 (14 g, 80% yield).

[0192] Step 4: Synthesis of C566-IM-4

[0193]

[0194] In a 1L dry round-bottom flask under nitrogen protection, C566-IM-3 (10g, 1.0eq, 27.6mmol) and 200mL of ultra-dry tetrahydrofuran were added sequentially. The mixture was cooled to -78℃, and then n-butyllithium (2.5M, 12mL, 1.1eq, 30.36mmol) was added dropwise. The reaction was continued at this temperature for 1 hour. Then, triisopropyl borate (7.79g, 1.5eq, 41.4mmol) was added, and the mixture was slowly heated to room temperature and reacted overnight. Then, a suitable amount of dilute hydrochloric acid was added, and the mixture was stirred for another hour. Then, a suitable amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with a suitable amount of n-heptane. The mixture was filtered to obtain a white solid intermediate C566-IM-4 (7.2g, 80% yield).

[0195] Step 5: Synthesis of C566-IM-5

[0196]

[0197] In a dry 500 mL round-bottom flask, C566-IM-4 (7 g, 1.0 eq, 21.4 mmol), SM4 (5.06 g, 1.0 eq, 21.4 mmol), potassium carbonate (7.38 g, 2.5 eq, 53.5 mmol), and tetraphenylphosphine palladium (742 mg, 0.03 eq, 0.642 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 100 mL of toluene, 10 mL of ethanol, and 10 mL of water were added, and the mixture was heated to 95 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a yellow solid intermediate, C566-IM-5 (6.2 g, 66% yield).

[0198] Step 6: Synthesis of C566-IM-6

[0199]

[0200] In a dry 500 mL round-bottom flask under nitrogen protection, C566-IM-5 (6 g, 1.0 eq, 13.67 mmol), cesium carbonate (13.4 g, 3.0 eq, 41.01 mmol), palladium acetate (153 mg, 0.05 eq, 0.684 mmol), tricyclohexylphosphine tetrafluoroborate (503 mg, 0.1 eq, 1.367 mmol), and 100 mL of xylene were added sequentially. The mixture was heated to 150 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and washed with a suitable amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate C566-IM-6 (5 g, 91% yield).

[0201] Step 7: Synthesis of C566-IM-7

[0202]

[0203] In a dry round-bottom flask under nitrogen protection, C566-IM-6 (5 g, 1.0 eq, 12.43 mmol), triphenylphosphine (9.78 g, 3.0 eq, 37.29 mmol), and 100 mL of o-dichlorobenzene were added sequentially. The mixture was heated to 150 °C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the product was separated by column chromatography to obtain a yellow solid intermediate C566-IM-7 (3.7 g, yield 80%).

[0204] Step 8: Synthesis of C566

[0205]

[0206] In a dry round-bottom flask under nitrogen protection, C566-IM-7 (3.7 g, 1.0 eq, 10 mmol), SM5 (3.93 g, 1.2 eq, 12 mmol), cesium carbonate (6.52 g, 2.0 eq, 20 mmol), and 100 mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 150 °C and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and a suitable amount of water was added dropwise. A large amount of yellow solid precipitated. The crude product was filtered off and separated by column chromatography to obtain yellow solid C566 (5.15 g, yield 76%).

[0207] Product MS (m / e): 677; Elemental analysis (C) 47 H 27 N5O): Theoretical values: C: 83.29%, H: 4.02%, N: 10.33%; Measured values: C: 83.3%, H: 3.96%, N: 10.21%.

[0208] Synthesis Example 2: Synthesis of Compound C577

[0209] Step 1: Synthesis of C577-IM-1

[0210]

[0211] In a 1 L dry round-bottom flask, SM6 (25 g, 1.0 eq, 140.44 mmol), SM7 (42.6 g, 1.5 eq, 210.66 mmol), potassium carbonate (58.2 g, 3.0 eq, 421.32 mmol), and tetraphenylphosphine palladium (8.1 g, 0.05 eq, 7.02 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 300 mL of tetrahydrofuran and 100 mL of water were added, and the mixture was heated to 70 °C and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid C577-IM-1 (28.7 g, 80% yield).

[0212] Step 2: Synthesis of C577-IM-2

[0213]

[0214] In a dry 1L round-bottom flask under nitrogen protection, C577-IM-1 (20g, 1.0 eq, 78.34 mmol), triphenylphosphine (61.64g, 3.0 eq, 235.02 mmol), and 200 mL of o-dichlorobenzene were added sequentially, and the mixture was heated to 150 °C and reacted for 6 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the solid intermediate C577-IM-2 (14g, 80% yield) was obtained by column chromatography.

[0215] Step 3: Synthesis of C577-IM-3

[0216]

[0217] In a 1 L dry round-bottom flask under nitrogen protection, C577-IM-2 (14 g, 1.0 eq, 62.7 mmol), SM3 (11 g, 1.0 eq, 62.7 mmol), cesium carbonate (61.3 g, 3.0 eq, 188.1 mmol), and 300 mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 150 °C and reacted for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, and an appropriate amount of water was added. The mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid intermediate C577-IM-3 (19.7 g, yield 83%).

[0218] Step 4: Synthesis of C577-IM-4

[0219]

[0220] In a 1L dry round-bottom flask under nitrogen protection, C577-IM-3 (19g, 1.0eq, 50.23mmol) and 300mL of ultra-dry tetrahydrofuran were added sequentially. The mixture was cooled to -78℃, and then n-butyllithium (2.5M, 22mL, 1.1eq, 55.25mmol) was added dropwise. The reaction was continued at this temperature for 1 hour. Then, triisopropyl borate (14.17g, 1.5eq, 75.35mmol) was added, and the mixture was slowly heated to room temperature and reacted overnight. Then, a suitable amount of dilute hydrochloric acid was added, and the mixture was stirred for another hour. Then, a suitable amount of water was added, and the mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and then slurried with a suitable amount of n-heptane. The mixture was filtered to obtain a white solid intermediate C577-IM-4 (14g, yield 81%).

[0221] Step 5: Synthesis of C577-IM-5

[0222]

[0223] In a dry 500 mL round-bottom flask, C577-IM-4 (14 g, 1.0 eq, 40.79 mmol), SM4 (9.65 g, 1.0 eq, 40.79 mmol), potassium carbonate (14.1 g, 2.5 eq, 102 mmol), and tetraphenylphosphine palladium (1.4 g, 0.03 eq, 1.224 mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 200 mL of toluene, 20 mL of ethanol, and 20 mL of water were added, and the mixture was heated to 95 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with ethyl acetate, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a yellow solid intermediate, C577-IM-5 (13 g, 70% yield).

[0224] Step 6: Synthesis of C577-IM-6

[0225]

[0226] In a dry round-bottom flask under nitrogen protection, C577-IM-5 (13 g, 1.0 eq, 28.58 mmol), cesium carbonate (27.9 g, 3.0 eq, 85.74 mmol), palladium acetate (321 mg, 0.05 eq, 1.43 mmol), tricyclohexylphosphine tetrafluoroborate (1.05 g, 0.1 eq, 2.858 mmol), and 200 mL of xylene were added sequentially. The mixture was heated to 150 °C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and washed with a suitable amount of dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain a yellow solid intermediate C577-IM-6 (10.3 g, yield 86%).

[0227] Step 7: Synthesis of C577-IM-7

[0228]

[0229] In a dry round-bottom flask under nitrogen protection, C577-IM-6 (10 g, 1.0 eq, 24 mmol), triphenylphosphine (18.9 g, 3.0 eq, 72 mmol), and 200 mL of o-dichlorobenzene were added sequentially. The mixture was heated to 150 °C and reacted for 12 hours. After the reaction was complete, the solvent was removed by concentration under reduced pressure, and the solution was separated by column chromatography to obtain a yellow solid intermediate C577-IM-7 (7 g, yield 75%).

[0230] Step 8: Synthesis of C577

[0231]

[0232] In a dry 2L round-bottom flask under nitrogen protection, C577-IM-7 (3g, 1.0eq, 7.763mmol), SM5 (3.05g, 1.2eq, 9.315mmol), cesium carbonate (5.06g, 2.0eq, 15.53mmol), and 100mL of N,N-dimethylacetamide were added sequentially. The mixture was heated to 150℃ and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and a suitable amount of water was added dropwise. A large amount of yellow solid precipitated. The crude product was filtered off and separated by column chromatography to obtain yellow solid C577 (3.8g, 70% yield).

[0233] Product MS (m / e): 693; Elemental analysis (C) 47 H 27 N5S): Theoretical values: C: 81.36%, H: 3.92%, N: 10.09%; Measured values: C: 81.35%, H: 3.94%, N: 10.06%.

[0234] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0235] Device Example 1

[0236] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, The deposition rate is achieved sequentially on the ITO anode via thermal vacuum. Simultaneously, the deposited compounds HT and NDP-9 are used as a hole injection layer (HIL), with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the compound C566 of this invention, as the main component, and the compound RD, as a dopant, are co-deposited as an emissive layer (EML) with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL) with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0237] The material structure used in the device is shown below:

[0238]

[0239] Device Example 2

[0240] The implementation method of Device Example 2 is the same as that of Device Example 1, except that Compound C577 of the present invention is used instead of Compound C566 of the present invention as the main body in the light-emitting layer (EML).

[0241] Device Comparison Example 1

[0242] The implementation method of Comparative Example 1 is the same as that of Example 1, except that compound A is used instead of compound C566 of the present invention as the main component in the light-emitting layer (EML). The structure of compound A is as follows:

[0243]

[0244] Device Comparison Example 2

[0245] The implementation method of Comparative Example 2 is the same as that of Comparative Example 1, except that compound B is used instead of compound C566 of the present invention as the main component in the light-emitting layer (EML). The structure of compound B is as follows:

[0246]

[0247] Device Comparison Example 3

[0248] The implementation method of Comparative Example 3 is the same as that of Device Example 1, except that compound C is used instead of compound C566 of the present invention as the main component in the light-emitting layer (EML). The structure of compound C is as follows:

[0249]

[0250] The detailed device layer structures and thicknesses of Device Examples 1-2 and Comparative Examples 1-3 are shown in Table 1 below. The layers used are made of more than one material and are obtained by doping different compounds in the stated weight ratios.

[0251] Table 1. Device structures of the device embodiments and comparative examples.

[0252]

[0253]

[0254] Table 2 lists the values ​​at 15 mA / cm 2 Under the conditions, the measured current efficiency (CE) and maximum wavelength (λ) max ) and external quantum efficiency (EQE). To better illustrate the data comparison, the CE and EQE data of Comparative Example 2 were set to 100%. The CE and EQE data of Examples 1, 2, Comparative Example 1 and 3 were converted relative to the corresponding data of Comparative Example 2. The relevant data and conversion results are shown in Table 2.

[0255] Table 2 Device Data:

[0256]

[0257] discuss:

[0258] As shown in Table 2, the maximum wavelength of the comparative examples and the embodiments remained essentially unchanged. At 15 mA / cm² 2 The EQE of Examples 1 and 2, measured at current densities, was increased by 8% and 5% respectively compared to the EQE of Comparative Example 1; the CE of Examples 1 and 2 was increased by 7% and 5% respectively compared to Comparative Example 1; at 15 mA / cm 2 The EQE of Examples 1 and 2, measured at current densities, was 11% and 8% higher than that of Comparative Example 3, respectively; the CE of Examples 1 and 2 was 9% and 7% higher than that of Comparative Example 3, respectively, showing a significant improvement; at 15 mA / cm 2The EQE of Examples 1 and 2, measured at current density, was 18% and 15% higher than that of Comparative Example 2, respectively; the CE of Examples 1 and 2 was 14% and 12% higher than that of Comparative Example 2, respectively, showing a more significant improvement. The data indicate that the examples have superior luminous efficiency compared to the comparative examples. Specifically, the compounds of this invention, which are formed by connecting hole transport units with indole-pyrrole fused nitrogen macrocyclic structures to electron transport units with triazine or similar structures, exhibit different device performance compared to Comparative Examples A, B, and C due to the change in the hole transport unit core. Unexpectedly, this results in excellent device performance, leading to higher current efficiency and external quantum efficiency, and a significant improvement in device performance. This demonstrates the unique advantages of the compounds of this invention.

[0259] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

[0260] Although the present invention has been described in detail above with general descriptions and specific embodiments, modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, all such modifications or improvements made without departing from the spirit of the present invention fall within the scope of protection claimed by the present invention.

Claims

1. A compound, characterized in that, The compound has an HL-Ar structure; The structure of H is as follows, or the structure obtained by partially or completely replacing hydrogen with deuterium in any of the following structures: ， ， ， ， ， ， ， ， ， ， ， ； Each time L appears, it is selected from the following structures and groups thereof: structures numbered L-1 to L-3, structures obtained by partially or completely replacing hydrogen in any of the structures numbered L-1 to L-3 with deuterium, and combinations thereof; The structures corresponding to numbers L-1 to L-3 are: ， ， ； Each time Ar appears, it is selected from the following structures and groups thereof: the structures shown in Ar-97 to Ar-106, the structures obtained by partially or completely replacing hydrogen in any of the structures shown in Ar-97 to Ar-106 with deuterium, and combinations thereof; The structures corresponding to Ar-97 to Ar-106 are as follows: ， ， ， ， ， ， ， ， ， ； " "Indicates the position where it bonds with L.

2. The compound according to claim 1, characterized in that, The compound is selected from compounds with the following structures, wherein H, L, and Ar are respectively selected from the following structures:

3. 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 as described in claim 1 or 2; The organic layer is a light-emitting layer, and the compound is the host material.

4. The electroluminescent device according to claim 3, characterized in that, The light-emitting layer also contains at least one phosphorescent material.

5. A composition, characterized in that, It contains the compound as described in claim 1 or 2.

6. A display component, characterized in that, It includes the electroluminescent device as described in claim 3 or 4.

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