Compound, organic electroluminescent device containing the same and application thereof

Abstract

To provide a novel compound that is applicable to OLED devices and can enhance device performance.SOLUTION: Provided is a compound having a structure represented by the following formula (III) [Formulas (A) and (B) are condensed at the positions of the dotted lines].SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to the field of organic light-emitting compounds and organic electroluminescent devices, and particularly to compounds, organic electroluminescent devices containing such compounds, and their applications.

Background Art

[0002] In recent years, optoelectronic devices based on organic materials have been gaining popularity. Due to the inherent flexibility of organic materials, they are very suitable for manufacturing on flexible substrates, and if necessary, beautiful and cool optoelectronic products can be designed and produced, obtaining incomparable advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLEDs have developed particularly rapidly and have already achieved commercial success in the field of information display. OLEDs can provide three highly saturated colors of red, green, and blue, and full-color display devices made of them do not require other backlight light sources, and have advantages such as vivid colors, thinness, and softness.

[0003] As OLEDs progress in the two fields of lighting and display, research on their core materials has also attracted attention. This is because highly efficient and long-life OLED devices are usually the result of an optimal combination of device structures and various organic materials. To prepare OLED light-emitting devices with lower driving voltages, higher luminous efficiencies, and longer device service lives and to realize the improvement of the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to research and innovate the optoelectronic functional materials in OLED devices in order to prepare more high-performance functional materials. Based on this, the OLED materials industry has been working on the development of new organic electroluminescent materials in order to achieve low turn-on voltages, high luminous efficiencies, and excellent service lives of devices.

[0004] At present, various organic materials have been developed, and by combining various unique device structures, the carrier mobility can be improved, the carrier balance can be adjusted, the electroluminescence efficiency can be broken through, and device decay can be delayed. For quantum mechanical reasons, common fluorescent phosphors mainly utilize singlet exciton emission that occurs when electrons and holes combine, and are still widely used in various OLED products at present. Metal complexes such as iridium complexes can emit light by simultaneously utilizing triplet excitons and singlet excitons, and are called phosphorescent phosphors, and their energy conversion efficiency can be improved by four times compared with conventional fluorescent phosphors. Thermally activated delayed fluorescence (TADF) technology can effectively utilize triplet excitons to achieve high luminescence efficiency without using metal complexes by promoting the transition from triplet excitons to singlet excitons. Thermally activated sensitized fluorescence (TASF) technology can also achieve high luminescence efficiency by using materials with TADF characteristics and sensitizing the phosphor through energy transfer. However, phosphorescent host materials still have much room for improvement in terms of luminescence performance such as carrier transport ability.

[0005] As OLED products gradually enter the market, the requirements for the performance of such products are becoming increasingly high. The currently used OLED materials and device structures cannot completely solve the problems in aspects such as the efficiency, lifespan, and cost of OLED products.

[0006] Therefore, in this field, in order to improve device performance, it is necessary to develop more types of OLED materials with higher performance.

Summary of the Invention

Problems to be Solved by the Invention

[0007] As described above, the currently used OLED materials and device structures are becoming increasingly difficult to meet the needs in aspects such as the efficiency, lifespan, and cost of OLED devices. Therefore, the development of new compounds applicable to OLED devices and capable of improving device performance is expected.

[0008] The inventor of the present application focused on the research of new OLED materials and developed excellent materials applicable to the hole transport layer and the electron blocking layer. Specifically, the object of the present invention is to provide a compound capable of improving the mobility of holes and achieving balance in an OLED element, an organic electroluminescence element containing the compound, and its applications. The OLED element fabricated by the compound of the present invention has a low turn-on voltage, a high luminous efficiency, and a better service life, and can meet the current requirements of panel manufacturers for high-performance materials.

Means for Solving the Problems

[0009] As a result of intensive research, the inventor found that by controlling the structure of "naphthalene triarylamine", the triplet energy level of the target molecule can be effectively controlled, thereby obtaining a new hole transport material with good hole transport performance and a high triplet energy level. The "naphthalene triarylamine" mentioned here is a tri "aryl" amine containing a naphthalene ring structure directly linked to nitrogen, and here "aryl" is a superordinate concept including a heteroaryl group, a condensed ring aryl group, and a condensed ring heteroaryl group. The three "aryl" and the central nitrogen atom of "naphthalene triarylamine" may be directly linked or linked via a linking group.

[0010] Furthermore, the inventor found that in "naphthalene triarylamine", when there is a specific substituent at the ortho position of the diarylamine group of the naphthalene ring, or when one aryl of the tri "aryl" amine is a binaphthyl group (i.e., there is a naphthyl group substituted or unsubstituted on the naphthalene ring), another aryl is a substituted or unsubstituted benzodimethylfluorenyl group, and the third aryl is a specific substituent, the target molecule has an appropriate triplet energy level. The specific substituent is a substituted or unsubstituted C6~C 30 aryl group, a substituted or unsubstituted C3~C 30 heteroaryl group.

[0011] The present invention provides a compound characterized by having a structure represented by (I). JPEG2025090627000001.jpg61170

[0012] Here, Ar 1 and Ar 2 are each independently selected from hydrogen, a substituted or unsubstituted C6-C 50 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 50 condensed aryl group, a substituted or unsubstituted C3-C 30 condensed heteroaryl group, and when Ar 1 is hydrogen, L 1 is not a single bond, and when Ar 2 is hydrogen, L 2 is not a single bond, and Ar 3 is a substituted or unsubstituted C6-C 50 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 50 condensed aryl group, a substituted or unsubstituted C3-C 30 condensed heteroaryl group.

[0013] L 1 ~L 3 are each independently selected from a single bond, a substituted or unsubstituted C1-C 10 alkylene group, a substituted or unsubstituted C6-C 50 arylene group, a substituted or unsubstituted C3-C 30 heteroarylene group.

[0014] m is an integer from 0 to 6, and n is an integer from 0 to 15.

[0015] R 1 are each independently hydrogen, halogen, carbonyl group, carboxyl group, amino group, amine group, cyano group, nitro group, ester group, hydroxyl group, silyl group, a substituted or unsubstituted C1-C 20An alkyl group, a substituted or unsubstituted C3-C 20 cycloalkyl group, a substituted or unsubstituted C2-C 20 alkenyl group, a substituted or unsubstituted C2-C 20 alkynyl group, a substituted or unsubstituted C1-C 20 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkoxy group, a substituted or unsubstituted C6-C 50 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, C6-C 50 selected from fused aryl groups.

[0016] R 2 is, Ar 1 ~Ar 3 L 1 ~L 3 R 1 or a substituent in the naphthalene ring of formula (I), each independently being hydrogen, halogen, carbonyl group, carboxyl group, cyano group, nitro group, ester group, hydroxyl group, amine group, C1-C 10 silyl group, a substituted or unsubstituted C1-C 20 alkyl group, a substituted or unsubstituted C3-C 20 cycloalkyl group, C2-C 12 alkenyl group, C2-C 12 alkynyl group, a substituted or unsubstituted C1-C 12 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkoxy group, a substituted or unsubstituted C6-C 50 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, C6-C 50 selected from fused aryl groups.

[0017] JPEG2025090627000002.jpg33170

[0018] When each of the substituted or unsubstituted groups has a substituent, the substituent is halogen, cyano group, nitro group, ester group, hydroxyl group, carbonyl group, carboxyl group, cyano group, amine group, C1-C 10 silyl group, C1-C 20 alkyl group, C3-C 20 cycloalkyl group, C2-C 20 alkenyl group, C2-C 10 alkynyl group, C1-C 20 alkoxy group or thioalkoxy group of, C6-C 30 arylamino group, C3-C 30 heteroarylamino group, C6-C 30 monocyclic aryl group or condensed ring aryl group of, C6-C 30 monocyclic heteroaryl group or condensed ring heteroaryl group of C3-C, and is one or more selected from the group consisting of.

[0019] The compound of the present invention is a tri "aryl" amine having a naphthalene ring structure directly linked to nitrogen. Here, at the ortho position of the diarylamine group in the naphthalene ring, there is a substituted or unsubstituted C6-C 30 aryl group, or a substituted or unsubstituted C3-C 30 heteroaryl group, or one aryl of the tri "aryl" amine group is a binaphthyl group, another aryl is a substituted or unsubstituted benzodimethylfluorenyl group, and the third aryl is a substituted or unsubstituted C6-C 30 aryl group, or a substituted or unsubstituted C3-C 30 heteroaryl group. The compound of the present invention has good hole transport performance, a high triplet energy level, and is suitable as a hole transport material.

[0020] In this specification, the expression "Ca~Cb" indicates that the number of carbon atoms in this group is from a to b. Generally, unless otherwise specified, the number of carbon atoms does not include the carbon atoms of substituents. The limitation of the range of the number of carbon atoms also means that the number of carbon atoms in this group can be any integer within the said numerical range. In the present invention, the expression "chemical element" includes the concept of isotopes having the same chemical properties. For example, the expression "hydrogen" includes the concepts of "deuterium" and "tritium" having the same chemical properties.

[0021] In this specification, "-" is not connected to the ring, and the expression method through the ring structure indicates that the connection position can be any bondable position of this ring structure.

[0022] In this specification, unless otherwise explained, the aryl group and heteroaryl group respectively refer to a monocyclic aryl group and a monocyclic heteroaryl group.

[0023] In this specification, a substituted or unsubstituted C6~C 50 The number of carbon atoms of the aryl group or condensed aryl group can be, for example, 6, 8, 10, 12, 14, 15, 16, 18, 20, 23, 25, 26, 28, 30, 33, 35, 38, 40, 45, 50, etc. Unless otherwise explained, a substituted or unsubstituted C6~C 50 The aryl group or condensed aryl group is preferably C6~C 30It is an aryl group or a condensed aryl group, more preferably a group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an indenyl group, a fluorenyl group and its derivatives, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a tetracenyl group. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl groups. The terphenyl group includes a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, and an m-terphenyl-2-yl group. The naphthyl group includes a 1-naphthyl group and a 2-naphthyl group. The anthracenyl group is selected from a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group. The fluorenyl group derivatives are selected from a 9,9'-dimethylfluorenyl group, a 9,9'-spirodifluorenyl group, and a benzofluorenyl group. The pyrenyl group is selected from a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group. The tetracenyl group is selected from a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group. Unless otherwise specified, preferably it is a phenyl group, biphenyl, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, etc., more preferably a phenyl group and a naphthyl group, and most preferably a phenyl group.

[0024] C6~C in this specification 50 The arylene group is obtained by removing one hydrogen from the C6~C 50 aryl group. Unless otherwise specified, C6~C 50 The number of carbon atoms and preferred examples of the arylene group correspond to those of the C6~C 50 aryl group (after removing one hydrogen). C6~C 50 Specific examples of the arylene group include, for example, a phenylene group, a naphthylene group, etc.

[0025] As used herein, a heteroatom is usually an atom or atomic group selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S, and more preferably N. As used herein, a heteroaryl group means that at least one ring carbon atom of an aryl group is substituted with a heteroatom.

[0026] As used herein, a substituted or unsubstituted C3-C 30 The number of carbon atoms of a heteroaryl group or a fused heteroaryl group may be, for example, 3, 5, 6, 8, 10, 12, 14, 15, 16, 18, 20, 23, 25, 26, 28, 30, etc. Unless otherwise specified, a substituted or unsubstituted C3-C 30 The heteroaryl group or the fused heteroaryl group is preferably a C4-C 20 heteroaryl group or a fused heteroaryl group, more preferably a nitrogen-containing heteroaryl group or a fused heteroaryl group, an oxygen-containing heteroaryl group or a fused heteroaryl group, a sulfur-containing heteroaryl group or a fused heteroaryl group, etc. Specific examples include a furanyl group, a thienyl group, a pyrrolyl group, a bipyridyl group, a benzofuranyl group, a benzothienyl group, an isobenzofuranyl group, an indolyl group, a quinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group and its derivatives. Among them, the carbazolyl group derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole. Unless otherwise specified, it is preferably a pyridyl group, a quinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, and more preferably a pyridyl group.

[0027] As used herein, C3-C 30 The heteroarylene group is obtained by removing one hydrogen from the C3-C 30 heteroaryl group. Unless otherwise specified, the number of carbon atoms of the C3-C 30 heteroarylene group and the preferred examples correspond to those of the C3-C 30 heteroaryl group (after removing one hydrogen). C3-C30 Specific examples of the heteroarylene group include, for example, a pyridylene group, a pyrrolylene group, and the like.

[0028] In this specification, the alkyl group is a chain alkyl group, and the chain alkyl group may be a straight-chain alkyl group or may contain a branched chain. C1 to C 20 In the chain alkyl group, the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 15, 18, 20, etc. Unless otherwise specified, C1 to C 20 The chain alkyl group is preferably a C1 to C 10 chain alkyl group, more preferably a C1 to C6 chain alkyl group. Examples of the chain alkyl group include, for example: methyl group, ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-octyl group, isopropyl group, isobutyl group, t-butyl group, and the like. Unless otherwise specified, the alkyl group is preferably selected from a methyl group, an ethyl group, an n-propyl group, and an isopropyl group, and more preferably a methyl group.

[0029] In this specification, the alkylene group is a chain alkylene group, and the chain alkylene group may be a straight-chain alkylene group or may contain a branched chain. Unless otherwise specified, C1 to C in this specification 10 The alkylene group may be one obtained by removing one hydrogen from the above C1 to C 10 chain alkyl group. Examples of the C1 to C 10 alkylene group include, for example: methylene group, ethylene group, propylene group, and the like.

[0030] In this specification, C3 to C 20 The number of carbon atoms of the cycloalkyl group may be, for example, 4, 5, 6, 7, 8, 9, 10, etc. C3 to C 20 Examples of the cycloalkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and the like.

[0031] In this specification, C2 to C 20The number of carbon atoms in the alkenyl group may be, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc., and is C2-C 20 Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, etc. C2-C 20 The number of carbon atoms in the alkynyl group may be, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc., and is C2-C 20 Examples of the alkynyl group include an ethynyl group, a propynyl group, a 1-butynyl group, etc.

[0032] In this specification, C1-C 20 The number of carbon atoms in the alkoxy group may be, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc. C1-C 20 Examples of the alkoxy group include the group obtained by connecting the above C1-C 20 A group obtained by connecting a linear alkyl group and -O-, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxyl group, a decyloxy group, an undecyloxy group, a dodecyloxy group, etc. Among them, a methoxy group, an ethoxy group, and a propoxy group are preferable, and a methoxy group is more preferable.

[0033] In this specification, C3-C 10 The number of carbon atoms in the cycloalkoxy group may be, for example, 4, 5, 6, 7, 8, 9, 10, etc. C3-C 10 Examples of the cycloalkoxy group include the above C3-C 20 A group obtained by connecting a cycloalkyl group and -O-, for example, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclooctyloxy group, etc.

[0034] In this specification, C1-C 20 Examples of the thioalkoxy group include the above C1-C 20 A group in which oxygen in the alkoxy group is substituted with sulfur, for example, a methylthio group, a thiooctyloxy group (octylthio group), etc.

[0035] In this specification, examples of the halogen include fluorine, chlorine, bromine, iodine, etc., and without particular explanation, fluorine is preferably used.

[0036] In this specification, unless otherwise specified, the amino group refers to the -NH2 group, and the amine group refers to a group in which at least one hydrogen of the amino group is substituted with an organic group (i.e., N and C are directly connected), including alkylamino groups, arylamino groups, heteroarylamino groups, etc. C6~C 30 The number of carbon atoms of the arylamino group may be, for example, 10, 12, 14, 16, 18, 20, 26, 28, etc. C6~C 30 Examples of the arylamino group include the group obtained by connecting the C6~C 30 group obtained by connecting an aryl group and -NH-, for example, phenylamino group, naphthylamino group, etc. C3~C 30 The number of carbon atoms of the heteroarylamino group may be, for example, 6, 8, 10, 12, 14, 16, 18, 20, 26, 28, etc. C3~C 30 Examples of the heteroarylamino group include the C3~C 30 group obtained by connecting a heteroaryl group and -NH-, for example, pyridylamino group, pyrrolylamino group, etc.

[0037] In this specification, C1~C 10 Examples of the silyl group include methylsilyl group, trimethylsilyl group, triethylsilyl group, etc.

[0038] Based on the above compounds of the present invention, by further limiting its structure (type of substituents, connection position, etc.), compounds with more excellent performance can be obtained. Hereinafter, three preferred forms will be described.

[0039] <Preferred Embodiment 1> The compound of the present invention preferably has a structure represented by (I). JPEG2025090627000003.jpg70170

[0040] JPEG2025090627000004.jpg19170

[0041] Ar 1 ~Ar 3 is each independently a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group selected from.

[0042] L 1 ~L 3 is each independently a single bond, a substituted or unsubstituted C6-C 30 arylene, or a substituted or unsubstituted C6-C 30 heteroarylene group selected from.

[0043] R 1 is independently hydrogen, C1-C 20 linear alkyl group, C3-C 20 cycloalkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 alkoxy group, halogen, cyano group, nitro group, hydroxyl group, silyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group selected from one kind.

[0044] R 2 is Ar 1 ~Ar 3 、L 1 ~L 3 、R 1 or a substituent on the naphthalene ring in formula (I), and is independently hydrogen, a substituted or unsubstituted C3-C 20 cycloalkyl group selected from one kind, and at least one R 2 is a substituted or unsubstituted C3-C 20 cycloalkyl group selected from.

[0045] m is an integer from 1 to 6, and n is an integer from 1 to 15.

[0046] When the above-mentioned substituted or unsubstituted group has a substituent, the substituent is halogen, C1-C 20 alkyl group, C3-C 20 cycloalkyl group, C2-C 20 alkenyl group, C1-C 20 alkoxy group or thioalkoxy group of, C6-C 30 monocyclic aryl group or condensed ring aryl group of, C3-C 30 monocyclic heteroaryl group or condensed ring heteroaryl group of, and is one or a combination of multiple types selected therefrom.

[0047] Since there is a specific aryl group or heteroaryl substituent at the ortho position of the "naphthalene triarylamine" of the present invention, the triplet energy level of the molecule can be effectively controlled to be high. At the same time, by introducing a cycloalkyl group into the molecule, the arrangement of the molecules adopting a planar expansion can be promoted, the carrier transport performance is increased, and the light extraction efficiency is improved, thereby improving the optoelectronic and lifespan performance of the device.

[0048] Furthermore, Ar 3 is a substituted or unsubstituted C 10 -C 30 condensed ring aryl group, or a substituted or unsubstituted C6-C 30 condensed ring heteroaryl group.

[0049] The organic compound of the present invention may specifically have a structure represented by the following (a) to (c). JPEG2025090627000005.jpg55170

[0050] The organic compound of the present invention preferably has a structure represented by (A-1) to (A-3). JPEG2025090627000006.jpg59170

[0051] Here, R 3 is independently hydrogen, C1-C20 A chain alkyl group, C3-C 20 A cycloalkyl group, C2-C 20 An alkenyl group, C2-C 20 An alkynyl group, C1-C 20 An alkoxy group, halogen, cyano group, nitro group, hydroxyl group, silyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C3-C 30 Is one selected from a heteroaryl group, and X is O, S, NR 4 , CR 5 R 6 Or SiR 7 R 8 And R 4 ~R 8 Are each independently hydrogen, a C1-C 20 Chain alkyl group, C3-C 20 Cycloalkyl group, a substituted or unsubstituted C6-C 30 Aryl group, a substituted or unsubstituted C3-C 30 Selected from heteroaryl groups, and R 5 And R 6 Are each preferably independently a methyl group. When the organic compound has a structure represented by formula (A-1), a is an integer from 1 to 7. When the organic compound has a structure represented by formula (A-2), a is an integer from 1 to 8. When the organic compound has a structure represented by formula (A-3), a is an integer from 1 to 7. In other words, the organic compound of the present invention has a structure in which Ar 3 Is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzoXheterocyclopentadiene, and X is preferably oxygen, nitrogen, sulfur, or silicon.

[0052] In the case of the above-mentioned preferred structure, the specific reason for the more excellent performance as a hole transport material is not clear, but it is presumed that when Ar 3 Of naphthalenetriarylamine is the condensed ring aryl group or condensed ring heteroaryl group, the molecular plane can be developed, which is advantageous for hole transport.

[0053] The organic compound of the present invention JPEG2025090627000007.jpg47170 JPEG2025090627000008.jpg55170 preferably has a structure represented by any of JPEG2025090627000009.jpg56170.

[0054] JPEG2025090627000010.jpg47170

[0055] In the organic compound of the present invention, R 2 is preferably independently selected from one of the following structures. JPEG2025090627000011.jpg94170 JPEG2025090627000012.jpg50170 JPEG2025090627000013.jpg42170

[0056] R 2 is more preferably independently selected from one of a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0057] The organic compound of the present invention is such that Ar 1 is a substituted or unsubstituted C 10 ~C 30 condensed ring aryl group, or a substituted or unsubstituted C6~C 30 condensed ring heteroaryl group, and Ar 2 is a substituted or unsubstituted C6~C 30 non-condensed ring aryl group, or a substituted or unsubstituted C3~C 30 non-condensed ring heteroaryl group, which can improve the transport performance of the carrier.

[0058] Ar 1 is selected from one of the following structures. JPEG2025090627000014.jpg27170

[0059] Ar 2 is one selected from the following structures. JPEG2025090627000015.jpg38170

[0060] Here, the dotted line represents the connection position of the group, and the expression method where the dotted line passes through the benzene ring indicates that the connection position of the group is any bondable position of the benzene ring.

[0061] The organic compound of the present invention is Ar 1 and Ar 2 at least one of which preferably has a substituted or unsubstituted C3 - C 20 cycloalkyl substituent. This is advantageous for adjusting the spatial stereoconformation and realizing the control of the intermolecular distance. More preferably, Ar 2 has a substituted or unsubstituted C3 - C 20 cycloalkyl substituent. By introducing a cycloalkyl group into Ar 2 , the spatial form filling of the target molecule and the molecular crystallinity can be effectively controlled, so that a new hole transport material with good hole transport performance, high triplet energy level, and stable amorphous thin film can be obtained.

[0062] In the organic compound of the present invention, L 1 and L 2 are each preferably independently selected from a single bond, a phenylene group, or a naphthylene group, and more preferably L 1 ~L 3 are all single bonds. This is advantageous for denser packing of the molecules and improvement of the hole transport performance.

[0063] The organic compound of the present invention is preferably selected from the structures represented by the following P1 - P291, but these compounds are merely exemplary.

[0064] JPEG2025090627000016.jpg195148 JPEG2025090627000017.jpg227170 JPEG2025090627000018.jpg223170 JPEG2025090627000019.jpg218170 JPEG2025090627000020.jpg222170 JPEG2025090627000021.jpg222170 JPEG2025090627000022.jpg228170 JPEG2025090627000023.jpg220170 JPEG2025090627000024.jpg218170 JPEG2025090627000025.jpg218170 JPEG2025090627000026.jpg221170 JPEG2025090627000027.jpg241170 JPEG2025090627000028.jpg226170 JPEG2025090627000029.jpg255160 JPEG2025090627000030.jpg229170 JPEG2025090627000031.jpg229170 JPEG2025090627000032.jpg218170 JPEG2025090627000033.jpg237170 JPEG2025090627000034.jpg228170 JPEG2025090627000035.jpg223170 JPEG2025090627000036.jpg230170 JPEG2025090627000037.jpg221170 JPEG2025090627000038.jpg223170 JPEG2025090627000039.jpg226170 JPEG2025090627000040.jpg62170

[0065] The present invention provides an application of the organic compound to an organic electronic device. Preferably, the specific application fields of the organic compound include, but are not limited to, technical fields such as organic electroluminescence materials, lighting members, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners, electronic paper, or organic EL panel groups, etc. More preferably, it is applied to organic electroluminescence materials, and particularly applied as a hole transport material or an electron blocking material for an organic electroluminescence device.

[0066] The present invention provides an organic electroluminescence device including a first electrode, a second electrode, and at least one organic layer inserted between the first electrode and the second electrode. Here, at least one kind of the organic compound is included in the organic layer. More specifically, the organic layer is divided into a plurality of regions. For example, the organic layer may include a hole transport region, a light emitting layer, an electron transport region, etc.

[0067] The present invention further provides an organic electroluminescence device including an anode layer, a plurality of light emitting functional layers, and a cathode layer. The plurality of light emitting functional layers include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer formed in sequence. The hole injection layer is formed on the anode layer, and the cathode layer is formed on the electron transport layer. Here, the organic compound is included in the hole transport layer and / or the electron blocking layer.

[0068] <Preferred Embodiment Two> The compound of the present invention preferably has a structure represented by the following formula (II). JPEG2025090627000041.jpg62170

[0069] Here, L 1 and L2 is independently selected from a single bond, a substituted or unsubstituted C6-C 50 arylene group, or a substituted or unsubstituted C3-C 30 heteroarylene group.

[0070] Ar 1 and Ar 2 are each independently selected from hydrogen, a substituted or unsubstituted C6-C 50 aryl group, a substituted or unsubstituted C6-C 50 condensed aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, or a substituted or unsubstituted C3-C 30 condensed heteroaryl group, and when Ar 1 is hydrogen, L 1 is not a single bond, and when Ar 2 is hydrogen, L 2 is not a single bond.

[0071] R 1 and R 2 are each independently selected from hydrogen, halogen, carbonyl group, carboxyl group, cyano group, amine group, C1-C 20 alkyl group, C3-C 20 cycloalkyl group, C2-C 12 alkenyl group, C2-C 12 alkynyl group, C1-C 12 alkoxy group, a substituted or unsubstituted C6-C 50 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, or a C6-C 50 condensed aryl group, and R 1 and R 2 are linked to the naphthalene ring via a single bond.

[0072] m is an integer from 0 to 6, and n is an integer from 0 to 7.

[0073] When the group has a substituent, the substituents are each independently selected from halogen, carbonyl group, carboxyl group, cyano group, amine group, C1-C 10An alkyl group, C3-C 10 A cycloalkyl group, C2-C 10 An alkenyl group, an alkoxy group having 1 to 6 carbon atoms, a thioalkoxy group having 1 to 6 carbon atoms, C6-C 30 A monocyclic aryl group or a condensed ring aryl group, C3-C 30 A monocyclic heteroaryl group or a condensed ring heteroaryl group, and is one or more selected therefrom.

[0074] In the present invention, in the said compound, the 1-position of the naphthalene ring is linked to another naphthalene ring, and the 2-position of the naphthalene ring is linked to a diarylamine group. When such a binaphthyl compound is used as a hole transport layer material or an electron blocking layer material of an organic electroluminescence device, compared with the prior art, the driving voltage can be further reduced, the luminous efficiency can be improved, and the service life can be extended.

[0075] In the compound of the present invention, naphthalene has its 1-position linked to another naphthalene ring, its 2-position linked to a diarylamine group, and in the two naphthalene rings, other substituents are not substituents of amines or aromatic amines. That is, R 1 and R 2 are not substituents of amines or aromatic amines.

[0076] In the said compound of the present invention, Ar 1 and Ar 2 are independently preferably selected from a substituted or unsubstituted C6-C 50 aryl group or a condensed aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, or a condensed heteroaryl group, and L 1 and L 2 are preferably a single bond, and R 1 and R 2 are preferably hydrogen.

[0077] JPEG2025090627000042.jpg24170 JPEG2025090627000043.jpg89170 JPEG2025090627000044.jpg112170

[0078] The above compound of the present invention may specifically have a structure represented by formula (II-1) or formula (II-2). JPEG2025090627000045.jpg51148 Here, L 1 、L 2 、Ar 1 、Ar 2 、R 1 、R 2 、m, and n are the same as defined in formula (II).

[0079] In the compound of the present invention, Ar 1 and Ar 2 are each independently JPEG2025090627000046.jpg57148 It is more preferably selected from

[0080] The compound having the structure represented by formula (II) of the present invention is preferably any one of the following compounds N1 to N419, but these compounds are merely exemplary. JPEG2025090627000047.jpg85148 JPEG2025090627000048.jpg212170 JPEG2025090627000049.jpg216170 JPEG2025090627000050.jpg211170 JPEG2025090627000051.jpg214170 JPEG2025090627000052.jpg216170 JPEG2025090627000053.jpg220170 JPEG2025090627000054.jpg209170 JPEG2025090627000055.jpg214170 JPEG2025090627000056.jpg216170 JPEG2025090627000057.jpg224170 JPEG2025090627000058.jpg226170 JPEG2025090627000059.jpg217170 JPEG2025090627000060.jpg204170 JPEG2025090627000061.jpg178170 JPEG2025090627000062.jpg237170

[0081] The present invention provides an organic electroluminescence element including a first electrode, a second electrode, and at least one organic layer inserted between the first electrode and the second electrode. Here, the compound is included in the organic layer.

[0082] In the organic electroluminescence element, preferably, the organic layer includes a hole transport region, the hole transport region includes the compound, more preferably, the hole transport region includes a hole transport layer and / or an electron blocking layer, and the compound is included in at least one of the hole transport layer and the electron blocking layer.

[0083] The present invention provides the application of the compound as a hole transport layer and / or an electron blocking layer in an organic electroluminescence element, but the organic layer containing the compound of the present invention is not limited to being used in the hole transport layer and the electron blocking layer.

[0084] Furthermore, the compound of the present invention can be applied to organic electronic devices, and examples of the organic electronic devices include, for example, organic electroluminescence elements, lighting members, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, large area sensors such as sheet scanners, electronic paper, and organic EL panel groups.

[0085] <Preferred Embodiment Three> The compound of the present invention preferably has the structure shown in formula (III): JPEG2025090627000063.jpg81170Formula (A) and formula (B) are condensed at the dotted line.

[0086] L 1 is a single bond, substituted or unsubstituted C1-C 10 Alkylene group, substituted or unsubstituted C6-C 30 Arylene group, substituted or unsubstituted C3-C 30 It is one selected from heteroarylene groups.

[0087] Ar 1 is a substituted or unsubstituted C6-C 30 Aryl groups, substituted or unsubstituted C3-C 30 It is one selected from heteroaryl groups.

[0088] R 1 , R 2 , R 3 , R 4 and R 5 are independently halogen, amino group, cyano group, nitro group, ester group, hydroxyl group, C1-C 10 Silyl groups, substituted or unsubstituted C1-C 10 Chain alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Alkenyl groups, substituted or unsubstituted C2-C 10 Alkynyl groups, substituted or unsubstituted C1-C 10 Chain alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkoxy groups, substituted or unsubstituted C6-C 30 Arylamino groups, substituted or unsubstituted C3-C 30 Heteroarylamino groups, substituted or unsubstituted C6-C 30 Aryl groups, substituted or unsubstituted C3-C 30 It is one selected from heteroaryl groups.

[0089] m is an integer from 0 to 6, for example, 1, 2, 3, 4, 5, etc., and when m ≥ 2, R 1 are the same or different.

[0090] n is an integer from 0 to 7, for example, 1, 2, 3, 4, 5, 6, etc., and when n ≥ 2, R 2 are the same or different.

[0091] p is an integer from 0 to 2, for example, 1, 2, 3, 4, 5, etc., and when p = 2, R 3 are the same or different.

[0092] q is an integer from 0 to 3, for example, 1, 2, 3, etc., and when q ≥ 2, R 4 are the same or different.

[0093] s is an integer from 0 to 4, and when s ≥ 2, R 5 are the same or different.

[0094] When the group has a substituent, the substituent is halogen, cyano group, C1 - C 10 linear alkyl group, C3 - C 10 cycloalkyl group, C1 - C6 alkoxy group, C1 - C6 thioalkoxy group, C6 - C 30 arylamino group, C3 - C 30 heteroarylamino group, C6 - C 30 monocyclic aryl group, C 10 - C 30 fused - ring aryl group, C3 - C 30 monocyclic heteroaryl group, C6 - C 30 is one kind or at least a combination of two kinds selected from fused - ring heteroaryl groups.

[0095] The present invention provides a new compound having a structure in which two units of binaphthyl and benzofluorene are respectively bonded to an N atom. Further, Ar 1By incorporating it, the compound has good hole injection and hole transport performance, a good refractive index, and a relatively high phase transition temperature. Therefore, the OLED device containing the compound has the characteristics of high luminous efficiency, low driving voltage, and long service life.

[0096] The compound of the present invention has three condensation positions a, b, and c, and depending on the condensation position, it can be specifically divided into three types of structures represented by the following formulas (III-1), (III-2), and (III-3). JPEG2025090627000064.jpg55170

[0097] Said R 6 is R 1 ~R 5 has the same selection range as. Said r is an integer from 0 to 6, and when r ≥ 2, R 6 are the same or different.

[0098] The compound of the present invention preferably has a structure represented by formula (III-2), that is, it is preferable that the fluorenyl and the benzene ring are condensed at the position represented by formula (III-2). This is because the molecular arrangement condensed at the 6- and 7-positions has a more preferable arrangement when forming a film, which can not only effectively reduce the energy barrier of hole injection, but also improve the hole transport ability, thereby further improving the device performance.

[0099] The compound of the present invention also preferably has a structure represented by the following formula (3-1). JPEG2025090627000065.jpg65170Formulas (A-1) and (B) are condensed at the dotted line position.

[0100] Said L 1 , Ar 1 , R 1 , R 2 , R 3 , R 4 , R 5 , s, p, n, m, q all have the same selection range as in the previous text.

[0101] In the present invention, it is preferable that the naphthyl group and the arylamine group are substituted at the ortho position. Such a specific structure not only effectively reduces the energy barrier for hole injection, but also improves the hole transport ability, thereby further improving the light emission efficiency of the device, reducing the driving voltage, and extending the service life.

[0102] In the formula (3-1) of the present invention, there are three condensation positions a, b, and c, and depending on the condensation position, it is specifically divided into three types of structures represented by the following formulas (3-1-1), (3-1-2), and (3-1-3). JPEG2025090627000066.jpg52170

[0103] Said L 1 , Ar 1 , R 1 , R 2 , R 6 , R 4 m, n, r, and q all have the same selection range as in the previous text.

[0104] It is more preferable that the above formula (3-1) is condensed at the position of b by formula (A-1) and formula (B), that is, the structure represented by formula (3-1-2) is preferable.

[0105] The compound of the present invention preferably also has a structure represented by the following formula (3-2). JPEG2025090627000067.jpg68170Formula (A-2) and formula (B) are condensed at the dotted line position.

[0106] Said L 1 , Ar 1 , R 1 , R 2 , R 3 , R 4 , R 5 s, p, n, m, and q all have the same selection range as in the previous text.

[0107] In the formula (3-2) of the present invention, there are three condensation positions of a, b, and c, and depending on the condensation position, it can be specifically divided into three types of structures represented by the following formulas (3-2-1), (3-2-2), and (3-2-3). JPEG2025090627000068.jpg51170

[0108] The above L 1 , Ar 1 , R 1 , R 2 , R 6 , R 4 , m, n, r, q all have the same selection range as described above.

[0109] It is more preferable that in the above formula (3-2), formula (A-2) and formula (B) are condensed at the position of b, that is, the structure represented by formula (3-2-2) is preferable.

[0110] In the above formulas (III), (3-1), and (3-2), it is preferable that s, p, n, m, q are all 0. In the above formulas (III-1), (III-2), (III-3), (3-1-1), (3-1-2), (3-1-3), (3-2-1), (3-2-2), and (3-2-3), it is preferable that n, m, q, and R are all 0.

[0111] The compound of the present invention preferably has a structure in which n, m, q, and R are all 0 in formula (3-2-1), formula (3-2-2), or formula (3-2-3), and more preferably has a structure in which n, m, q, and R are all 0 in formula (3-2-2).

[0112] In the compound of the present invention, L 1 is preferably selected from a single bond or a substituted or unsubstituted phenylene group, and more preferably a single bond. When there is a substituent on the group, the substituent is a halogen, a cyano group, a C1-C 10 chain alkyl group, a C3-C 10A cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 thioalkoxy group, a C6-C 30 An arylamino group, a C3-C 30 A heteroarylamino group, a C6-C 30 A monocyclic aryl group, a C 10 -C 30 A condensed-ring aryl group, a C3-C 30 A monocyclic heteroaryl group, a C6-C 30 It is one or at least a combination of two selected from a condensed-ring heteroaryl group.

[0113] In the compound of the present invention, Ar 1 is preferably one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group. When a substituent is present in the group, the substituent is a halogen, a cyano group, a C1-C 10 A chain alkyl group, a C3-C 10 A cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 thioalkoxy group, a C6-C 30 An arylamino group, a C3-C 30 A heteroarylamino group, a C6-C 30 A monocyclic aryl group, a C 10 -C 30 A condensed-ring aryl group, a C3-C 30 A monocyclic heteroaryl group, a C6-C 30 It is one or at least a combination of two selected from a condensed-ring heteroaryl group.

[0114] In the compound of the present invention, -L-Ar 1 is preferably one selected from a phenyl group, a biphenyl group, a terphenyl group, dibenzofuran, dibenzothiophene, a carbazolyl group, or a phenanthryl group.

[0115] The compound having the structure represented by the above formula (III) of the present invention is preferably any one of the following compounds T1 to T255, but these compounds are merely exemplary.

[0116] JPEG2025090627000069.jpg224170 JPEG2025090627000070.jpg236170 JPEG2025090627000071.jpg225170 JPEG2025090627000072.jpg226170 JPEG2025090627000073.jpg233170 JPEG2025090627000074.jpg233170 JPEG2025090627000075.jpg244170 JPEG2025090627000076.jpg233170 JPEG2025090627000077.jpg249170

[0117] The present invention provides an application of the above compound to an organic electroluminescence device. The compound is preferably used as an electron blocking layer material of the organic electroluminescence device.

[0118] The present invention provides an organic electroluminescence device including a substrate, a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the above compounds. Preferably, the organic layer includes an electron blocking layer, and the electron blocking layer contains the compound.

Advantages of the Invention

[0119] By designing the structure of "naphthalene triarylamine", the triplet energy level of the target molecule can be effectively controlled, so that a new hole-transporting material with good hole-transporting properties and a high triplet energy level can be obtained. Specifically, "naphthalene triarylamine" is substituted or unsubstituted at the ortho-position of the diarylamine group in the naphthalene ring with a C6~C 30 aryl group, or a substituted or unsubstituted C3~C 30 heteroaryl group, or "naphthalene triarylamine" is designed to have a structure in which one of the "aryl" amine groups is a binaphthyl group, another aryl is a substituted or unsubstituted benzodimethylfluorenyl group, and the third aryl is a substituted or unsubstituted C6~C 30 aryl group, or a substituted or unsubstituted C3~C 30 heteroaryl group. By designing in this way, the triplet energy level of the molecule can be adjusted higher, and a new hole-transporting material with good hole-transporting performance can be obtained.

[0120] When the specific substituent is present at the ortho-position of the diarylamine group in the naphthalene ring, if a cycloalkyl is introduced at a specific position of the molecule, the arrangement of the molecules adopting a planar expansion can be promoted, the carrier transport performance can be improved, the light extraction efficiency can be increased at the same time, and the optoelectronic and lifetime performance of the device can be improved. When this material is used as the hole-transporting layer material or the electron blocking layer of the organic electroluminescence device, the luminous efficiency can be improved, the turn-on voltage can be reduced, and the service life of the device can be extended. If another naphthalene ring is linked to the 1-position of the naphthalene ring of the molecule and the 2-position is linked to the diarylamine group, the compound of the present invention has a large π-plane structure, the molecular spatial structure can be effectively changed, which is beneficial to the improvement of the molecular packing in the film, and by restricting the rotation of the aromatic ring at the N atom due to the ortho-substitution, the stability of such a material is enhanced. When the compound is used as the hole-transporting layer material and / or the electron blocking layer of the organic electroluminescence device, the luminous efficiency can be improved, the turn-on voltage can be reduced, and the device can have a longer service life.

[0121] When the arylamine group contains binaphthyl, benzofluorenyl group, and specific aromatic groups linked to nitrogen, the compound has good hole injection and hole transport performance, good refractive index, and relatively high phase change temperature. If applied to devices, it can improve the luminous efficiency of OLED devices, reduce the driving voltage, and extend the service life.

Brief Description of Drawings

[0122]

Figure 1

Figure 2

Figure 3

Figure 4

Embodiments for Carrying Out the Invention

[0123] Hereinafter, the technical embodiments of the present invention will be further described by specific embodiments. Those skilled in the art can understand that the above embodiments are only for facilitating the understanding of the present invention and should not be regarded as specific limitations to the present invention.

[0124] <Configuration of the Organic Electroluminescence Device of the Present Invention> In a specific example, a substrate may be used under the first electrode or on the second electrode. The substrate is any glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Further, a thin film transistor (TFT) may also be attached to the substrate for display.

[0125] The first electrode can be formed by a method of sputtering or depositing a material used as the first electrode on a substrate. When the first electrode is used as an anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. and any combination thereof can be used.

[0126] The organic layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer may be an organic low molecule, an organic high molecule, a polymer, and any combination thereof.

[0127] The hole transport region is interposed between the anode and the light-emitting layer. The hole transport region may be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one kind of compound and a single-layer hole transport layer containing multiple kinds of compounds. The hole transport region may also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0128] In one aspect of the present invention, the electron blocking layer of the hole transport region may be selected from one or more compounds of the present invention. In this case, the hole transport layer of the hole transport region is selected from phthalocyanine derivatives such as CuPc, polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS) and other conductive polymers or polymers containing conductive dopants, aromatic amine derivatives such as the compounds shown by the following HT-1 to HT-34, or any combination thereof, but not limited thereto.

[0129] In another aspect of the present invention, the hole transport layer in the hole transport region may be selected from one or more compounds of the present invention. In this case, the electron blocking layer in the hole transport region is a phthalocyanine derivative such as CuPc, polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), a conductive polymer containing a conductive dopant, an aromatic amine derivative such as the compounds represented by the following HT-1 to HT-34, or any combination thereof, but is not limited thereto. JPEG2025090627000078.jpg44170 JPEG2025090627000079.jpg153170 JPEG2025090627000080.jpg77170 JPEG2025090627000081.jpg89170

[0130] The hole injection layer is interposed between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of multiple compounds. For example, the hole injection layer may use one or more compounds of the above HT-1 to HT-34, or one or more compounds of the following HI-1 to HI-3, or a material in which one or more compounds of the following HI-1 to HI-3 are doped into one or more compounds of HT-1 to HT-34. JPEG2025090627000082.jpg47170

[0131] The light-emitting layer contains light-emitting dyes (i.e., dopants) that emit spectra of different wavelengths, and may also contain a host material at the same time. The light-emitting layer may be a single-color light-emitting layer that emits a single color such as red, green, or blue. Multiple single-color light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or stacked to form a color light-emitting layer. When stacking light-emitting layers of different colors, they may be separated or connected to each other. The light-emitting layer may also be a single color light-emitting layer that emits different colors such as red, green, and blue simultaneously.

[0132] Depending on different technologies, the light-emitting layer material uses different materials such as fluorescent electroluminescence materials, phosphorescent electroluminescence materials, and thermally activated delayed fluorescence materials. In one OLED device, a single light-emitting technology may be adopted, or a combination of multiple different light-emitting technologies may be adopted. Different light-emitting materials classified by these technologies can emit light of the same color or different colors.

[0133] In one aspect of the present invention, the light-emitting layer adopts the technology of fluorescent electroluminescence. The fluorescent host material of the light-emitting layer may be selected from one or more combinations of BFH-1 to BFH-17 listed below, but is not limited thereto. JPEG2025090627000083.jpg117170

[0134] In one aspect of the present invention, the light-emitting layer adopts the technology of fluorescent electroluminescence. The fluorescent dopant of the light-emitting layer may be selected from one or more combinations of BFD-1 to BFD-12 listed below, but is not limited thereto. JPEG2025090627000084.jpg150170

[0135] In one aspect of the present invention, the light-emitting layer adopts the technology of phosphorescent electroluminescence. The host material of the light-emitting layer may be selected from one or more combinations of GPH-1 to GPH-80 listed below, but is not limited thereto. JPEG2025090627000085.jpg190170 JPEG2025090627000086.jpg222170 JPEG2025090627000087.jpg184170

[0136] In one aspect of the present invention, the light-emitting layer employs the technology of phosphorescent electroluminescence. The phosphorescent dopant in the light-emitting layer may be selected from one or more combinations of GPD-1 to GPD-47 listed below, but is not limited thereto. JPEG2025090627000088.jpg45159 JPEG2025090627000089.jpg234170 JPEG2025090627000090.jpg103170 Here, D is deuterium.

[0137] In one aspect of the present invention, the light-emitting layer employs the technology of phosphorescent electroluminescence. The phosphorescent dopant in the light-emitting layer may be selected from one or more combinations of RPD-1 to RPD-28 listed below, but is not limited thereto. JPEG2025090627000091.jpg235170

[0138] In one aspect of the present invention, the light-emitting layer employs the technology of phosphorescent electroluminescence. The phosphorescent dopant in the light-emitting layer may be selected from one or more combinations of YPD-1 to YPD-11 listed below, but is not limited thereto. JPEG2025090627000092.jpg65170

[0139] In one aspect of the present invention, the light-emitting layer employs the technology of thermally activated delayed fluorescence emission. The fluorescent dopant in the light-emitting layer may be selected from one or more combinations of TDE-1 to TDE-39 listed below, but is not limited thereto. JPEG2025090627000093.jpg35170 JPEG2025090627000094.jpg94170 JPEG2025090627000095.jpg134170 JPEG2025090627000096.jpg65170

[0140] In one aspect of the present invention, the light-emitting layer employs the technology of thermally activated delayed fluorescence. The main material of the light-emitting layer is selected from one or more combinations of TDH1 to TDH24, but is not limited thereto. JPEG2025090627000097.jpg186170 JPEG2025090627000098.jpg116170

[0141] The OLED organic layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one kind of compound and a single-layer electron transport layer containing multiple kinds of compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0142] In one aspect of the present invention, the electron transport layer material may be selected from one or more combinations of ET-1 to ET-57 listed below, but is not limited thereto. JPEG2025090627000099.jpg83159 JPEG2025090627000100.jpg246170 JPEG2025090627000101.jpg235170

[0143] The device may further include an electron injection layer interposed between the electron transport layer and the cathode. The electron injection layer material includes one or more combinations of LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, but is not limited thereto.

[0144] <Method for Preparing the Compounds of the Present Invention> Hereinafter, the synthesis method of the organic compounds of the present invention will be outlined by specific synthesis examples. Solvents and reagents used in the following synthesis examples, such as aryl bromides, 2-bromo-9,9'-dimethylfluorene, 2-bromodibenzofuran, 2-bromodibenzothiophene, 4-bromobiphenyl, 4-cyclohexylbromobenzene, 4-(4'-cyclohexylphenyl)bromobenzene, tris(dibenzylideneacetone)dipalladium, 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride, toluene, tetrahydrofuran, petroleum ether, n-hexane, dichloromethane, acetone, sodium sulfate, ethyl acetate, ethanol, acetic acid, potassium phosphate, tri-tert-butylphosphine, potassium / sodium tert-butoxide, aniline, 1-naphthylamine, 2-naphthylamine, 2-aminobiphenyl, 2-amino-4-methoxy-5'-methoxy-1,2'-binaphthyl, 2-amino-1,2'-binaphthyl, 2-amino-4-methoxy-5'-methoxy-1,1'-binaphthyl, 2-amino-1,1'-binaphthyl, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, triphenylphosphine and other chemical reagents can all be purchased from the domestic chemical product market or made to order, for example, they can be purchased from Sinopharm Chemical Reagent Co., Ltd., Shanghai Titan Scientific Co., Ltd., Xilong Chemical Co., Ltd., Sigma-Aldrich, and Bailingwei Reagent Co., Ltd. Also, the intermediates are made to order by reagent companies, and those skilled in the art may synthesize them by known methods.

[0145] A representative scheme of the compounds of general formula (I) of the present invention is as follows, but the synthesis method of the compounds of the present invention is not limited thereto. JPEG2025090627000102.jpg68170

[0146] Here, m, n, R 1 、R 2 、L 1 、L2 and L 3 Ar 1 Ar 2 and Ar 3 all have the same meaning as the symbols in general formula (I).

[0147] More specifically, the following synthesis examples of the present invention exemplarily show specific synthesis methods of representative compounds. The mass spectrometer used to determine the following compounds was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0148] <Synthesis of the compound of Preferred Embodiment 1> Synthesis Example 1-1: Synthesis of Compound P1 JPEG2025090627000103.jpg85170

[0149] Into a 1000 mL single-necked flask, 13.5 g (50 mmol) of M1, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder M1-1 was obtained by suction filtration.

[0150] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M1-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder P1.

[0151] Theoretical value of M / Z: 619; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 620.

[0152] Synthesis Example 1-2: Synthesis of Compound P3 JPEG2025090627000104.jpg88170

[0153] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M1, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder M1-1.

[0154] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M1-1, 16 g (100 mmol) of 4-(4-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and exchange with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a light yellow powder P3.

[0155] Theoretical value of M / Z: 695; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 696.

[0156] Synthesis Example 1-3: Synthesis of Compound P11 JPEG2025090627000105.jpg89170

[0157] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M1, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a light yellow powder M1-1.

[0158] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M1-1, 16 g (100 mmol) of 2-cyclohexyl-4-phenylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain light yellow powder P11.

[0159] Theoretical value of M / Z: 695; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 696.

[0160] Synthesis Example 1-4: Synthesis of Compound P31 JPEG2025090627000106.jpg85170

[0161] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M1, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain light yellow powder M1-1.

[0162] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M1-1, 20 g (100 mmol) of 2-phenyl-4(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder P31.

[0163] Theoretical value of M / Z: 771; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 772.

[0164] Synthesis Example 1-5: Synthesis of Compound P37 JPEG2025090627000107.jpg83170

[0165] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M1, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder M1-2.

[0166] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M1-2, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain pale yellow powder P37.

[0167] Theoretical value of M / Z: 619; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 620.

[0168] Synthesis Example 1-6: Synthesis of Compound P39 JPEG2025090627000108.jpg84170

[0169] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M1, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain pale yellow powder M1-2.

[0170] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M1-2, 16 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain pale yellow powder P39.

[0171] Theoretical value of M / Z: 695; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 696.

[0172] Synthesis Example 1-7: Synthesis of Compound P61 JPEG2025090627000109.jpg84170

[0173] Into a 1000 mL one-necked flask, add 16.5 g (50 mmol) of M2, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain pale yellow powder M2-1.

[0174] In a 1000 mL one-necked flask, 26.5 g (50 mmol) of M2-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and allowed to react for 5 h. After the reaction was complete, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder P61 was obtained by suction filtration.

[0175] Theoretical value of M / Z: 685; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 686.

[0176] Synthesis Example 1-8: Synthesis of Compound P62 JPEG2025090627000110.jpg88170

[0177] In a 1000 mL one-necked flask, 16.5 g (50 mmol) of M2, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and allowed to react for 5 h. After the reaction was complete, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder M2-1 was obtained by suction filtration.

[0178] In a 1000 mL one-necked flask, 26.5 g (50 mmol) of M2-1, 16 g (100 mmol) of 4-(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, suction filtration was performed to obtain a pale yellow powder P62.

[0179] Theoretical value of M / Z: 762; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 763.

[0180] Synthesis Example 1-9: Synthesis of Compound P73 JPEG2025090627000111.jpg85170

[0181] In a 1000 mL one-necked flask, 13.5 g (50 mmol) of M3, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, suction filtration was performed to obtain a pale yellow powder M3-1.

[0182] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M3-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain pale yellow powder P73.

[0183] Theoretical value of M / Z: 619; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 620.

[0184] Synthesis Example 1-10: Synthesis of Compound P75 JPEG2025090627000112.jpg91170

[0185] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M3, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain pale yellow powder M3-1.

[0186] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M3-1, 16 g (100 mmol) of 4-(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain light yellow powder P75.

[0187] Theoretical value of M / Z: 695; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 696.

[0188] Synthesis Example 1-11: Synthesis of Compound P97 JPEG2025090627000113.jpg92170

[0189] Into a 1000 mL one-necked flask, add 15.5 g (50 mmol) of M4, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain light yellow powder M4-1.

[0190] Into a 1000 mL one-necked flask, add 25 g (50 mmol) of M4-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder P97.

[0191] Theoretical value of M / Z: 659; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 660.

[0192] Synthesis Example 1-12: Synthesis of Compound P109 JPEG2025090627000114.jpg93170

[0193] Into a 1000 mL one-necked flask, add 16.2 g (50 mmol) of M5, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder M5-1.

[0194] Into a 1000 mL one-necked flask, 26 g (50 mmol) of M5-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and allowed to react for 5 h. After the reaction was complete, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder P109 was obtained by suction filtration.

[0195] Theoretical value of M / Z: 675; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 676.

[0196] Synthesis Example 1-13: Synthesis of Compound P121 JPEG2025090627000115.jpg89170

[0197] Into a 1000 mL one-necked flask, 19.5 g (50 mmol) of M6, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and allowed to react for 5 h. After the reaction was complete, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder M6-1 was obtained by suction filtration.

[0198] Into a 1000 mL one-necked flask, add 29 g (50 mmol) of M6-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain light yellow powder P121.

[0199] Theoretical value of M / Z: 734; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 735.

[0200] Synthesis Example 1-14: Synthesis of Compound P133 JPEG2025090627000116.jpg91170

[0201] Into a 1000 mL one-necked flask, add 19.5 g (50 mmol) of M7, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain light yellow powder M7-1.

[0202] Into a 1000 mL single-necked flask, add 29 g (50 mmol) of M7-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder P133.

[0203] Theoretical value of M / Z: 734; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 735.

[0204] Synthesis Example 1-15: Synthesis of Compound P173 JPEG2025090627000117.jpg90170

[0205] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of M8, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder M8-1.

[0206] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M8-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction mixture, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain pale yellow powder P173.

[0207] Theoretical value of M / Z: 619; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 620.

[0208] Synthesis Example 1-16: Synthesis of Compound P189 JPEG2025090627000118.jpg98170

[0209] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of M8, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction mixture, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain pale yellow powder M8-1.

[0210] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of M8-1, 20 g (100 mmol) of 2-phenyl-4-(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain pale yellow powder P189.

[0211] Theoretical value of M / Z: 771; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 772.

[0212] Synthesis Example 1-17: Synthesis of Compound P198 JPEG2025090627000119.jpg102170

[0213] Into a 1000 mL one-necked flask, add 15.5 g (50 mmol) of M9, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain pale yellow powder M9-1.

[0214] Into a 1000 mL one-necked flask, add 25 g (50 mmol) of M9-1, 16 g (100 mmol) of 4-(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the gas with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder P198.

[0215] Theoretical value of M / Z: 735; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 736.

[0216] Synthesis Example 1-18: Synthesis of Compound P209 JPEG2025090627000120.jpg100170

[0217] Into a 1000 mL one-necked flask, add 16 g (50 mmol) of M10, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the gas with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder M10-1.

[0218] Into a 1000 mL one-necked flask, add 26 g (50 mmol) of M10-1, 12 g (100 mmol) of 4-(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder P209.

[0219] Theoretical value of M / Z: 675; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 676.

[0220] Synthesis Example 1-19: Synthesis of Compound P224 JPEG2025090627000121.jpg105170

[0221] Into a 1000 mL one-necked flask, add 19 g (50 mmol) of M11, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder M11-1.

[0222] Into a 1000 mL one-necked flask, add 29 g (50 mmol) of M11-1, 16 g (100 mmol) of 2-phenyl-4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder P224.

[0223] Theoretical value of M / Z: 810; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 811.

[0224] Synthesis Example 1-20: Synthesis of Compound P229 JPEG2025090627000122.jpg97170

[0225] Into a 1000 mL one-necked flask, add 19 g (50 mmol) of M12, 16 g (50 mmol) of 4-(4-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder M12-1.

[0226] Into a 1000 mL one-necked flask, add 31 g (50 mmol) of M12-1, 12 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder P229.

[0227] Theoretical value of M / Z: 776; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 777.

[0228] Synthesis Example 1-21: Synthesis of Compound P269 JPEG2025090627000123.jpg97170

[0229] Into a 1000 mL one-necked flask, add 16 g (50 mmol) of M13, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder M13-1.

[0230] Into a 1000 mL single-necked flask, add 26.5 g (50 mmol) of M13-1, 12 g (100 mmol) of 4-(4'-cyclohexylphenyl)bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder P269.

[0231] Theoretical value of M / Z: 685; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 686.

[0232] Synthesis Example 1-22: Synthesis of Compound P179 JPEG2025090627000124.jpg105170

[0233] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of M8, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate the flask and replace the atmosphere with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder M8-1.

[0234] Into a 1000 mL one-necked flask, 23 g (50 mmol) of M8-1, 16.5 g (100 mmol) of 1-cyclohexyl-4-bromodibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 5 h. When the reaction was complete, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, suction filtration was performed to obtain a pale yellow powder P179.

[0235] Theoretical value of M / Z: 709; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 710.

[0236] Synthesis Example 1-23: Synthesis of Compound P287 JPEG2025090627000125.jpg74170

[0237] Into a 1000 mL one-necked flask, 26 g (50 mmol) of M15, 24 g (100 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 5 h. When the reaction was complete, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, suction filtration was performed to obtain a pale yellow powder P287.

[0238] Theoretical value of M / Z: 839; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 840.

[0239] JPEG2025090627000126.jpg100170

[0240] Into a 1000 mL single-necked flask, 17 g (50 mmol) of M16, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, the layers were separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The mixture was filtered by suction to obtain a pale yellow powder M16-1.

[0241] Into a 1000 mL single-necked flask, 27 g (50 mmol) of M16-1, 12 g (50 mmol) of 4-bromobiphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, the layers were separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The mixture was filtered by suction to obtain a pale yellow powder P42.

[0242] Theoretical value of M / Z: 695; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 696.

[0243] Synthesis Example 1-25: Synthesis of Compound P278 JPEG2025090627000127.jpg86170

[0244] Into a 1000 mL single-necked flask, 11 g (50 mmol) of M17, 13.6 g (50 mmol) of 3-bromo-9,9-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 g of IPr.HCl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and allowed to react for 5 h. After the reaction was complete, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder M17-1 was obtained by suction filtration.

[0245] Into a 1000 mL single-necked flask, 21 g (50 mmol) of M17-1, 12 g (50 mmol) of 4-cyclohexylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine ((t-Bu)3P), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and allowed to react for 5 h. After the reaction was complete, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder P278 was obtained by suction filtration.

[0246] Theoretical value of M / Z: 569; Measured value of M / Z by ZAB-HS type mass spectrometer (manufactured by Micromass, UK): 570.

[0247] <Synthesis of the compound of Preferred Embodiment 2> In the present invention, the synthesis method of the above compound will be briefly described. The typical scheme of the above compound is as follows. JPEG2025090627000128.jpg61170

[0248] Based on the above compound scheme and concept, those skilled in the art can determine that the substituents are Ar 1 、Ar 2 、R1 and R 2 A compound can be obtained.

[0249] Synthesis Example 2-1: Synthesis of Compound N1 JPEG2025090627000129.jpg47170

[0250] In a 1000 mL single-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 15.7 g (100 mmol) of bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder N1 was obtained by suction filtration. Theoretical value of M / Z: 421, Measured value of M / Z: 422.

[0251] Synthesis Example 2-2: Synthesis of Compound N13 JPEG2025090627000130.jpg41170

[0252] In a 1000 mL single-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 8.5 g (50 mmol) of 2-methylbromobenzene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (Pd(dppf)Cl2), 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder S0 was obtained.

[0253] Into a 1000 mL single-necked flask, add 18 g (50 mmol) of S0, 9.5 g (50 mmol) of p-bromoanisole, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 500 mL of toluene. Evacuate and replace with nitrogen three times. Add 0.5 mL of a toluene solution of tri-tert-butylphosphine (P(t-Bu)3). Heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N13 by silica gel column chromatography. Theoretical value of M / Z: 465, Measured value of M / Z: 466.

[0254] Synthesis Example 2-3: Synthesis of Compound N34 JPEG2025090627000131.jpg39170

[0255] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 12 g (50 mmol) of 2-bromobiphenyl, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (Pd(dppf)Cl2), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder S0-1.

[0256] In a 1000 mL one-necked flask, 21 g (50 mmol) of S0-1, 12 g (50 mmol) of p-bromobiphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. Then, 0.5 mL of a toluene solution of tri-tert-butylphosphine (P(t-Bu)3) was added. The temperature was raised to 110 °C and the reaction was carried out for 12 h. After the reaction was completed, the solvent was evaporated, and N34 was obtained by silica gel column chromatography. Theoretical value of M / Z: 573, Measured value of M / Z: 574.

[0257] Synthesis Example 2-4: Synthesis of Compound N63 JPEG2025090627000132.jpg53170

[0258] In a 1000 mL one-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 27 g (100 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.5 mL of tri-tert-butylphosphine (P(t-Bu)3), 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and carried out for 5 h. When the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, it was suction filtered to obtain a pale yellow powder N63. Theoretical value of M / Z: 653, Measured value of M / Z: 654.

[0259] Synthesis Example 2-5: Synthesis of Compound N93 JPEG2025090627000133.jpg86170

[0260] Into a 1000 mL single-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (Pd(dppf)Cl2), 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and allowed to react for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder S1 was obtained by suction filtration.

[0261] Into a 1000 mL single-necked flask, 23 g (50 mmol) of S1, 16.1 g (50 mmol) of 4-(4-bromo-phenyl)-dibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine (P(t-Bu)3) was added. The reaction was heated to 110 °C and allowed to react for 12 h. After the reaction was completed, the solvent was evaporated, and N93 was obtained by silica gel column chromatography. Theoretical value of M / Z: 703, Measured value of M / Z: 704.

[0262] Synthesis Example 2-6: Synthesis of Compound N94 JPEG2025090627000134.jpg73170

[0263] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S1.

[0264] Into a 1000 mL single-necked flask, add 23 g (50 mmol) of S1, 16.1 g (50 mmol) of 3-(4-bromo-phenyl)-dibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and exchange with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N94 by silica gel column chromatography. Theoretical value of M / Z: 703, Measured value of M / Z: 704.

[0265] Synthesis Example 2-7: Synthesis of Compound N100 JPEG2025090627000135.jpg66170

[0266] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 10.3 g (50 mmol) of 2-bromonaphthalene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S2.

[0267] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of S2, 8.3 g (50 mmol) of bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 500 ml of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N100 by silica gel column chromatography. Theoretical value of M / Z: 471, Measured value of M / Z: 472.

[0268] Synthesis Example 2-8: Synthesis of Compound N120 JPEG2025090627000136.jpg72170

[0269] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13 g (50 mmol) of 9-bromophenanthrene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (Pd(dppf)Cl2), 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder S0-2.

[0270] Into a 1000 mL single-necked flask, add 22 g (50 mmol) of S0-2, 15 g (50 mmol) of 3,5-diphenylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, 500 mL of toluene. Evacuate and exchange with nitrogen three times. Add 0.5 mL of a toluene solution of tri-tert-butylphosphine (P(t-Bu)3), heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N120 by silica gel column chromatography. Theoretical value of M / Z: 673, Measured value of M / Z: 674.

[0271] Synthesis Example 2-9: Synthesis of Compound N134 JPEG2025090627000137.jpg69170

[0272] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain light yellow powder S1.

[0273] Into a 1000 mL single-necked flask, add 23 g (50 mmol) of S1, 11.5 g (50 mmol) of 3-bromo-biphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N134 by silica gel column chromatography. Theoretical value of M / Z: 613, Measured value of M / Z: 614.

[0274] Synthesis Example 2-10: Synthesis of Compound N147 JPEG2025090627000138.jpg81170

[0275] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S1.

[0276] Into a 1000 mL single-necked flask, add 23 g (50 mmol) of S1, 10.4 g (50 mmol) of 2-bromonaphthalene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is complete, evaporate the solvent and obtain N147 by silica gel column chromatography. Theoretical value of M / Z: 587, Measured value of M / Z: 588.

[0277] Synthesis Example 2-11: Synthesis of Compound N170 JPEG2025090627000139.jpg52170

[0278] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 27 g (100 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder N170. Theoretical value of M / Z: 653, Measured value of M / Z: 654.

[0279] Synthesis Example 2-12: Synthesis of Compound N176 JPEG2025090627000140.jpg83170

[0280] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S1.

[0281] In a 1000 mL one-necked flask, 23 g (50 mmol) of S1, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added, and the temperature was raised to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N176 was obtained by silica gel column chromatography. Theoretical value of M / Z: 653, Measured value of M / Z: 654.

[0282] Synthesis Example 2-13: Synthesis of Compound N191 JPEG2025090627000141.jpg40170

[0283] In a 1000 mL one-necked flask, 13.5 g (50 mmol) of 2-amino-1,2'-binaphthyl, 15.7 g (100 mmol) of bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times, and the reaction was heated to 110 °C and reacted for 5 h. When the reaction was complete, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h and filtered by suction to obtain a pale yellow powder N191. Theoretical value of M / Z: 421, Measured value of M / Z: 422.

[0284] Synthesis Example 2-14: Synthesis of Compound N314 JPEG2025090627000142.jpg77170

[0285] Into a 1000 mL one-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13 g (50 mmol) of 9-bromoanthracene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (Pd(dppf)Cl2), 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. When the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, suction filtration was performed to obtain a pale yellow powder S0-3.

[0286] Into a 1000 mL one-necked flask, 22 g (50 mmol) of S0-3, 15 g (50 mmol) of 3,5-diphenylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine (P(t-Bu)3) was added. The reaction was heated to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N314 was obtained by silica gel column chromatography. Theoretical value of M / Z: 673, Measured value of M / Z: 674.

[0287] Synthesis Example 2-15: Synthesis of Compound N325 JPEG2025090627000143.jpg79170

[0288] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,2'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S2.

[0289] Into a 1000 mL single-necked flask, add 23 g (50 mmol) of S1, 11.5 g (50 mmol) of 3-bromo-biphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N325 by silica gel column chromatography. Theoretical value of M / Z: 613, Measured value of M / Z: 614.

[0290] Synthesis Example 2-16: Synthesis of Compound N331 JPEG2025090627000144.jpg79170

[0291] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,2'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol, stir for 1 h, and perform suction filtration to obtain a pale yellow powder S2.

[0292] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of S2, 12.3 g (50 mmol) of 2-bromo-dibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat the reaction to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N331 by silica gel column chromatography. Theoretical value of M / Z: 627, Measured value of M / Z: 628.

[0293] Synthesis Example 2-17: Synthesis of Compound N337 JPEG2025090627000145.jpg71170

[0294] Into a 1000 mL single-necked flask, 13.5 g (50 mmol) of 2-amino-1,2'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and allowed to react for 5 h. When the reaction was complete, the reaction was stopped. After cooling to room temperature, the reaction mixture was separated by liquid-liquid extraction. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder S2 was obtained by suction filtration.

[0295] Into a 1000 mL single-necked flask, 23 g (50 mmol) of S2, 10.4 g (50 mmol) of 2-bromonaphthalene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added. The reaction was heated to 110 °C and allowed to react for 12 h. After the reaction was completed, the solvent was evaporated, and N337 was obtained by silica gel column chromatography. Theoretical value of M / Z: 587, Measured value of M / Z: 588.

[0296] Synthesis Example 2-18: Synthesis of Compound N371 JPEG2025090627000146.jpg48170

[0297] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 32.2 g (100 mmol) of 9-(4-bromophenyl)-carbazole, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder N371. Theoretical value of M / Z: 751, Measured value of M / Z: 752.

[0298] Synthesis Example 2-19: Synthesis of Compound N372 JPEG2025090627000147.jpg54170

[0299] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 32.2 g (100 mmol) of 9-(3-bromophenyl)-carbazole, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder N372. Theoretical value of M / Z: 751, Measured value of M / Z: 752.

[0300] Synthesis Example 2-20: Synthesis of Compound N373 JPEG2025090627000148.jpg70170

[0301] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 30.9 g (100 mmol) of 3-bromoterphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder N373. Theoretical value of M / Z: 725, Measured value of M / Z: 726.

[0302] Synthesis Example 2-21: Synthesis of Compound N374 JPEG2025090627000149.jpg49170

[0303] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 24.5 g (100 mmol) of 4-bromodibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder N374. Theoretical value of M / Z: 601.31, Measured value of M / Z: 602.

[0304] Synthesis Example 2-22: Synthesis of Compound N375 JPEG2025090627000150.jpg64170

[0305] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 32.3 g (100 mmol) of 4-(4-bromophenyl)-dibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder N375. Theoretical value of M / Z: 753, Measured value of M / Z: 754.

[0306] Synthesis Example 2-23: Synthesis of Compound N376 JPEG2025090627000151.jpg40170

[0307] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino 0.5 mL-1,1'-binaphthyl, 10 g (100 mmol) of 2-bromonaphthalene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder N376. Theoretical value of M / Z: 521, Measured value of M / Z: 522.

[0308] Synthesis Example 2-24: Synthesis of Compound N377 JPEG2025090627000152.jpg58170

[0309] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 32.2 g (100 mmol) of (9-phenyl)-3-bromocarbazole, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder N377. Theoretical value of M / Z: 751, Measured value of M / Z: 752.

[0310] Synthesis Example 2-25: Synthesis of Compound N378 JPEG2025090627000153.jpg52170

[0311] Into a 1000 mL one-necked flask, add 6.7 g (25 mmol) of 2-amino-1,1'-binaphthyl, 20 g (100 mmol) of 4-bromo-9,9'-spirobifluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder N378. Theoretical value of M / Z: 898, Measured value of M / Z: 898.

[0312] Synthesis Example 2-26: Synthesis of Compound N379 JPEG2025090627000154.jpg91170

[0313] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a pale yellow powder S1.

[0314] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of S1, 32.2 g (100 mmol) of 9-(4-bromophenyl)-carbazole, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and exchange with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N379 by silica gel column chromatography. Theoretical value of M / Z: 702, Measured value of M / Z: 703.

[0315] Synthesis Example 2-27: Synthesis of Compound N380 JPEG2025090627000155.jpg84170

[0316] Into a 1000 mL one-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. When the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. Then, suction filtration was performed to obtain a pale yellow powder S1.

[0317] Into a 1000 mL one-necked flask, 23 g (50 mmol) of S1, 32.2 g (100 mmol) of 9-(3-bromophenyl)-carbazole, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added. The reaction was heated to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N380 was obtained by silica gel column chromatography. Theoretical value of M / Z: 702, Measured value of M / Z: 703.

[0318] Synthesis Example 2-28: Synthesis of Compound N381 JPEG2025090627000156.jpg77170

[0319] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain light yellow powder S1.

[0320] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of S1, 16.1 g (100 mmol) of (9-phenyl)-3-bromocarbazole, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and exchange with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N381 by silica gel column chromatography. Theoretical value of M / Z: 702, measured value of M / Z: 703.

[0321] Synthesis Example 2-29: Synthesis of Compound N382 JPEG2025090627000157.jpg40170

[0322] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-4-methoxy-5'-methoxy-1,1'-binaphthyl, 27 g (100 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, 0.5 mL of tri-tert-butylphosphine, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder N382. Theoretical value of M / Z: 713, Measured value of M / Z: 714.

[0323] Synthesis Example 2-30: Synthesis of Compound N383 JPEG2025090627000158.jpg81170

[0324] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-4-methoxy-5'-methoxy-1,2'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S2.

[0325] Into a 1000 mL one-necked flask, 23 g (50 mmol) of S2, 12.3 g (50 mmol) of 2-bromo-dibenzofuran, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added, and the temperature was raised to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N383 was obtained by silica gel column chromatography. Theoretical value of M / Z: 687, Measured value of M / Z: 688.

[0326] Synthesis Example 2-31: Synthesis of Compound N387 JPEG2025090627000159.jpg74170

[0327] Into a 1000 mL one-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 2-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times, and the reaction was heated to 90 °C and reacted for 5 h. When the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h and filtered by suction to obtain a light yellow powder S1.

[0328] Into a 1000 mL one-necked flask, 23 g (50 mmol) of S1, 13.5 g (100 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added, and the temperature was raised to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N387 was obtained by silica gel column chromatography. Theoretical value of M / Z: 653, Measured value of M / Z: 654.

[0329] Synthesis Example 2-32: Synthesis of Compound N389 JPEG2025090627000160.jpg78170

[0330] Into a 1000 mL single-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, the layers were separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder S4 was obtained by suction filtration.

[0331] Into a 1000 mL single-necked flask, 23 g (50 mmol) of S4, 12 g (100 mmol) of p-bromobiphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added. The reaction was heated to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N389 was obtained by silica gel column chromatography. Theoretical value of M / Z: 633, Measured value of M / Z: 634.

[0332] Synthesis Example 2-33: Synthesis of Compound N396 JPEG2025090627000161.jpg77170

[0333] Into a 1000 mL one-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, the layers were separated, the organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder S4 was obtained by suction filtration.

[0334] Into a 1000 mL one-necked flask, 23 g (50 mmol) of S4, 10.5 g (100 mmol) of 2-bromonaphthalene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added. The reaction was heated to 110 °C and reacted for 12 h. After the reaction was completed, the solvent was evaporated, and N396 was obtained by silica gel column chromatography. Theoretical value of M / Z: 587, Measured value of M / Z: 588.

[0335] Synthesis Example 2-34: Synthesis of Compound N405 JPEG2025090627000162.jpg77170

[0336] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S4.

[0337] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of S4, 8.7 g (100 mmol) of bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N405 by silica gel column chromatography. Theoretical value of M / Z: 537, measured value of M / Z: 538.

[0338] Synthesis Example 2-35: Synthesis of Compound N406 JPEG2025090627000163.jpg67170

[0339] Into a 1000 mL single-necked flask, 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and allowed to react for 5 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, methanol was added, and the mixture was stirred for 1 h. The resulting pale yellow powder S4 was obtained by suction filtration.

[0340] Into a 1000 mL single-necked flask, 23 g (50 mmol) of S4, 12 g (100 mmol) of 2-bromobiphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene were added. The flask was evacuated and purged with nitrogen three times. A toluene solution of 0.5 mL of tri-tert-butylphosphine was added. The reaction was heated to 110 °C and allowed to react for 12 h. After the reaction was completed, the solvent was evaporated, and N405 was obtained by silica gel column chromatography. Theoretical value of M / Z: 613, Measured value of M / Z: 614.

[0341] Synthesis Example 2-36: Synthesis of Compound N409 JPEG2025090627000164.jpg74170

[0342] Into a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and exchange with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S4.

[0343] Into a 1000 mL single-necked flask, add 23 g (50 mmol) of S4, 17.5 g (100 mmol) of 3-(2-(9,9-dimethylfluorenyl))bromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone)dipalladium, and 500 mL of toluene. Evacuate and exchange with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is completed, evaporate the solvent and obtain N409 by silica gel column chromatography. Theoretical value of M / Z: 729, measured value of M / Z: 730.

[0344] Synthesis Example 2-37: Synthesis of Compound N414 JPEG2025090627000165.jpg81170

[0345] Into a 1000 mL one-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution by liquid separation, concentrate the organic phase, add methanol and stir for 1 h, and perform suction filtration to obtain a pale yellow powder S4.

[0346] Into a 1000 mL one-necked flask, add 23 g (50 mmol) of S4, 15 g (100 mmol) of 3,5-diphenylbromobenzene, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is complete, evaporate the solvent and obtain N414 by silica gel column chromatography. Theoretical value of M / Z: 689, Measured value of M / Z: 690.

[0347] Synthesis Example 2-38: Synthesis of Compound N418 JPEG2025090627000166.jpg86170

[0348] In a 1000 mL single-necked flask, add 13.5 g (50 mmol) of 2-amino-1,1'-binaphthyl, 13.5 g (50 mmol) of 3-bromo-9,9'-dimethylfluorene, 0.7 g (1 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride, 0.5 g of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 500 mL of toluene, and 14.4 g (150 mmol) of sodium tert-butoxide. Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 5 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1 h, then perform suction filtration to obtain a light yellow powder S4.

[0349] In a 1000 mL single-necked flask, add 23 g (50 mmol) of S4, 15 g (100 mmol) of 2-phenyl-1-bromo-biphenyl, 0.9 g (1 mmol) of tris(dibenzylideneacetone) dipalladium, and 500 mL of toluene. Evacuate and replace with nitrogen three times. Add a toluene solution of 0.5 mL of tri-tert-butylphosphine, heat to 110 °C and react for 12 h. After the reaction is complete, evaporate the solvent and obtain N418 by silica gel column chromatography. Theoretical value of M / Z: 689, Measured value of M / Z: 690.

[0350] <Synthesis of the compound of Preferred Embodiment Three> The schemes of the compounds represented by formula (III-1), formula (III-2) and formula (III-3) of the present invention are as follows. JPEG2025090627000167.jpg141170

[0351] Hereinafter, several synthesis examples will be given to illustrate in detail the specific preparation method of the new compound of the present invention, but the preparation method of the present invention is not limited to these synthesis examples.

[0352] Synthesis Example 3-1: Synthesis of Compound T1 JPEG2025090627000168.jpg80170

[0353] Into a 500 mL single-necked flask, add 15 g (55.69 mmol) of compound P, 18 g (55.69 mmol) of 3-bromo-11,11-dimethyl-benzofluorene, 0.4 g (556.92 μmol) of 1,1'-bis(diphenylphosphino)ferrocene dichloride palladium (i.e., Pd(dppf)Cl2), 0.45 g (1.1 mmol) of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e., sphos), 200 mL of toluene, and 16.06 g (167.08 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 90 °C and react for 12 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, and obtain compound PM by silica gel column chromatography. Theoretical value of M / Z: 511, Measured value of M / Z: 512.

[0354] Into a 500 mL single-necked flask, add 20 g (39.09 mmol) of compound PM, 7.9 g (50.82 mmol) of bromobenzene, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone) dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 300 mL of toluene (Toluene), and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t). Evacuate and replace with nitrogen three times. Heat the reaction to 110 °C and react for 10 h. When the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, and obtain compound T1 by silica gel column chromatography. Theoretical value of M / Z: 587, Measured value of M / Z: 588.

[0355] Synthesis Example 3-2: Synthesis of Compound T2 JPEG2025090627000169.jpg59170

[0356] Into a 500 mL one-necked flask, 20 g (39.09 mmol) of compound PM, 11.85 g (50.82 mmol) of 4-bromobiphenyl, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 10 h. When the reaction was complete, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, and compound T2 was obtained by silica gel column chromatography. Theoretical value of M / Z: 663, measured value of M / Z: 664.

[0357] Synthesis Example 3-3: Synthesis of Compound T11 JPEG2025090627000170.jpg57170

[0358] Into a 500 mL one-necked flask, 20 g (39.09 mmol) of compound PM, 13.07 g (50.82 mmol) of 9-bromophenanthrene, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 10 h. When the reaction was complete, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, the organic phase was concentrated, and compound T11 was obtained by silica gel column chromatography. Theoretical value of M / Z: 687, measured value of M / Z: 688.

[0359] Synthesis Example 3-4: Synthesis of Compound T12 JPEG2025090627000171.jpg54170

[0360] Into a 500 mL one-necked flask, 20 g (39.09 mmol) of compound PM, 8.69 g (50.82 mmol) of 1-bromo-4-methylbenzene, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 10 h. When the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, and the organic phase was concentrated. Compound T12 was obtained by silica gel column chromatography. Theoretical value of M / Z: 601, measured value of M / Z: 602.

[0361] Synthesis Example 3-5: Synthesis of Compound T81 JPEG2025090627000172.jpg61170

[0362] Into a 500 mL one-necked flask, 15 g (55.69 mmol) of compound P, 18 g (55.69 mmol) of 2-bromo-11,11-dimethyl-benzofluorene, 0.4 g (556.92 μmol) of 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (i.e., Pd(dppf)Cl2), 0.45 g (1.1 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 200 mL of toluene, and 16.06 g (167.08 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 12 h. When the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was separated, and the organic phase was concentrated. Compound PN was obtained by silica gel column chromatography. Theoretical value of M / Z: 511, measured value of M / Z: 512.

[0363] Into a 500 mL single-necked flask, 20 g (39.09 mmol) of compound PN, 13.37 g (50.82 mmol) of 4-bromodibenzothiophene, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 10 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, and compound T81 was obtained by silica gel column chromatography. Theoretical value of M / Z: 693, Measured value of M / Z: 694.

[0364] Synthesis Example 3-6: Synthesis of Compound T163 JPEG2025090627000173.jpg62170

[0365] Into a 500 mL single-necked flask, 15 g (55.69 mmol) of compound PA, 18 g (55.69 mmol) of 4-bromo-11,11-dimethyl-benzofluorene, 0.4 g (556.92 μmol) of 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (i.e., Pd(dppf)Cl2), 0.45 g (1.1 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 200 mL of toluene, and 16.06 g (167.08 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 12 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, and compound PQ was obtained by silica gel column chromatography. Theoretical value of M / Z: 511, Measured value of M / Z: 512.

[0366] In a 500 mL single-necked flask, 20 g (39.09 mmol) of compound PQ, 11.85 g (50.82 mmol) of m-bromotoluene, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 10 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, the layers were separated, the organic phase was concentrated, and compound T163 was obtained by silica gel column chromatography. Theoretical value of M / Z: 663, Measured value of M / Z: 664.

[0367] Synthesis Example 3-7: Synthesis of Compound T170 JPEG2025090627000174.jpg46170

[0368] In a 500 mL single-necked flask, 20 g (39.09 mmol) of compound PQ, 10.52 g (50.82 mmol) of 2-bromonaphthalene, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110 °C and reacted for 10 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, the layers were separated, the organic phase was concentrated, and compound T170 was obtained by silica gel column chromatography. Theoretical value of M / Z: 637, Measured value of M / Z: 638.

[0369] Synthesis Example 3-8: Synthesis of Compound T232 JPEG2025090627000175.jpg53170

[0370] Into a 500 mL single-necked flask, 20 g (39.09 mmol) of compound PQ, 16.42 g (50.82 mmol) of 4-(4-bromophenyl)-dibenzofuran, 0.71 g (781.78 μmol) of tris(dibenzylideneacetone)dipalladium (i.e., Pd2(dba)3), 0.64 g (1.56 mmol) of 2-bicyclohexylphosphine-2′,6′-dimethoxybiphenyl (i.e., sphos), 300 mL of toluene, and 11.27 g (117.27 mmol) of sodium tert-butoxide (NaOBu-t) were added. The flask was evacuated and purged with nitrogen three times. The reaction was heated to 110° C. and reacted for 10 h. After the reaction was completed, the reaction was stopped. The reaction mixture was cooled to room temperature, and the layers were separated. The organic phase was concentrated, and compound T232 was obtained by silica gel column chromatography. Theoretical value of M / Z: 753, Measured value of M / Z: 754.

[0371] Hereinafter, the compounds of the present invention are specifically applied to an organic electroluminescence device to measure the actual use performance, and the technical effects and merits of the present invention are shown and verified.

[0372] <Device using the compound of Preferred Embodiment 1> Example 1-1 In this example, an organic electroluminescence device is provided, and the specific preparation process is as follows. A glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercially available cleaning agent, washed with deionized water, ultrasonically degreased with an acetone:ethanol mixed solvent, baked in a clean environment until the water was completely removed, washed with ultraviolet light and ozone, and a low-energy cation beam was collided with the surface.

[0373] The glass substrate provided with the above anode was placed in a vacuum chamber and evacuated to less than 1×10 -5 Pa. Then, a mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited as a hole injection layer on the anode layer film. The deposition rate was 0.1 nm / s, and the deposited film thickness was 10 nm.

[0374] HT-4 was vacuum deposited as the hole transport layer of the device on the positive hole injection layer. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 60 nm.

[0375] Compound P1 synthesized in Synthesis Example 1-1 was vacuum deposited as the electron blocking layer material of the device on the hole transport layer. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 60 nm.

[0376] The light-emitting layer of the device was vacuum deposited on the electron blocking layer. The light-emitting layer contained a host material and a dye material. Using the multi-source co-evaporation method, the deposition rate of the host material GPH-59 was adjusted to 0.1 nm / s, the deposition rate of the dye RPD-8 was set at a ratio of 3%, and the total deposited film thickness was 40 nm.

[0377] On the light-emitting layer, the electron transport layer material ET-46 of the device was set at a ratio of 50% and ET-57 was set at a ratio of 50% and vacuum deposited. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 25 nm.

[0378] On the electron transport layer (ETL), LiF with a thickness of 0.5 nm was used as the electron injection layer, and an Al layer with a thickness of 150 nm was vacuum deposited as the cathode of the device.

[0379] Examples 1-2 to 1-25 The manufacturing processes of Examples 1-2 to 1-25 were the same as those of Example 1-1 except that the electron blocking layer material compound P1 was changed to the compounds shown in Table 1 respectively.

[0380] Comparative Examples 1-1 to 1-2 The manufacturing processes of Comparative Examples 1-1 to 1-2 were the same as those of Example 1-1 except that the electron blocking layer material compound P1 was changed to compounds R-1 and R-2 respectively, and the structures of the compounds adopted in Comparative Examples 1-1 to 1-2 were as follows. JPEG2025090627000176.jpg55170

[0381] Performance measurements were carried out on the organic electroluminescence device prepared by the above process as follows. (1) At the same luminance, using a source meter (Keithley 2400) and a luminance meter (ST-86LA type luminance meter, Beijing Normal University Optoelectronic Instrument Factory), the driving voltage, current efficiency, and device lifetime of the organic electroluminescence devices prepared in Examples 1-1 to 1-25 and Comparative Examples 1-1 to 1-2 were measured. Specifically, the voltage was increased at a rate of 0.1 V / second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescence device reaches 5000 cd / m 2 , was measured. At the same time, the current density at this time was measured. The ratio of luminance to current density is the current efficiency. (2) The lifetime measurement of LT95 is as follows. Using a luminance meter at a luminance of 5000 cd / m 2 , a constant current was maintained, and the time until the luminance of the organic electroluminescence device decreased to 4750 cd / m 2 was measured. The unit is time.

[0382] The measurement results are shown in Table 1.

Table 1

[0383] As can be seen from the results in Table 1, when the compound of the present invention is used as the hole transport material of the organic electroluminescence device, when the device luminance reaches 5000 cd / m 2When reaching [a certain state], the driving voltage is as low as 5.0 V or less, the current efficiency is as high as 12.8 cd / A or more, and compared with Comparative Examples 1-1 to 1-2, the driving voltage can be effectively reduced and the current efficiency can be improved. This is an electron blocking material with good performance. Although the cause is not yet clear, it is speculated as follows. Compared with the compound R-1 of Comparative Example 1-1, when the compounds of Examples 1-1 to 1-25 of the present invention are used as the electron blocking material of the organic electroluminescence element, they have a cycloalkyl group substituted at a specific position and an aromatic substituent at the ortho position of the amine group on the naphthalene ring. Therefore, the unfolding of molecules on the element plane can be promoted, and then the deposited light-emitting layer molecules are also induced to perform such planar space filling. The light-emitting molecules filled in the planar unfolding mode are advantageous for improving the light extraction efficiency, so the current efficiency is improved. The compound R-2 used in Comparative Example 1-2 only lacks the aromatic substituent at the ortho position of the amine group, but still cannot achieve high efficiency and the voltage remains high. It can be seen that such molecules cannot achieve the advantageous molecular arrangement of the compounds of the present invention. From the above analysis, it can be seen that the unique molecular structure of the compounds of the present invention is the key to realizing the excellent performance shown in the examples of the device. The luminance of the organic electroluminescence element using the compound of the present invention is 5000 cd / m 2 When reaching [a certain state], the driving voltage is as low as 5.0 V or less, the current efficiency is as high as 12.8 cd / A or more, and LT95 is as long as 21 h or more.

[0384] <Device using the compound of Preferred Embodiment 2> Example 2-1 This example provides an organic electroluminescence element, and the specific preparation process is as follows. The glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercially available cleaning agent, washed with deionized water, ultrasonically degreased with an acetone:ethanol mixed solvent, baked in a clean environment until the moisture is completely removed, washed with ultraviolet rays and ozone, and a low-energy cation beam is collided with the surface.

[0385] The glass substrate provided with the above anode is placed in a vacuum chamber, <1×10-5 It was evacuated until it reached Pa, and HI-3 was vacuum-deposited as a hole injection layer on the anode layer film. The deposition rate was 0.1 nm / s, and the deposited film thickness was 10 nm.

[0386] Compound N1 prepared in Synthesis Example 2-1 was vacuum-deposited as the hole transport layer of the device on the hole injection layer. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 80 nm.

[0387] HT-14 was vacuum-deposited as the electron blocking layer of the device on the hole transport layer. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 80 nm.

[0388] The light-emitting layer of the device was vacuum-deposited on the electron blocking layer. The light-emitting layer contains a host material and a dye material. Using the multi-source co-evaporation method, the deposition rate of the host material GPH-59 was adjusted to 0.1 nm / s, the deposition rate of the dye RPD-8 was set at a ratio of 3%, and the total deposited film thickness was 30 nm.

[0389] On the light-emitting layer, the electron transport layer material ET-46 of the device was set at a ratio of 50% and ET-57 was set at a ratio of 50% and vacuum-deposited. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 30 nm.

[0390] On the electron transport layer (ETL), LiF with a thickness of 0.5 nm was used as the electron injection layer, and an Al layer with a thickness of 150 nm was vacuum-deposited as the cathode of the device.

[0391] Examples 2-2 to 2-33 and Comparative Examples 2-1 to 2-4 The production processes of Examples 2-2 to 2-33 and Comparative Examples 2-1 to 2-4 are the same as those of Example 2-1, except that compound N1 was replaced with the compounds shown in Table 2 as the hole transport material.

[0392] The structures of the hole transport materials EMT-1 to EMT-4 of Comparative Examples 2-1 to 2-4 are as follows. JPEG2025090627000178.jpg94159

[0393] For the organic electroluminescence devices prepared in Examples 2-1 to 2-33 and Comparative Examples 2-1 to 2-4, the following performance measurements were carried out.

[0394] At the same luminance, using a source meter and a luminance meter, the driving voltage, current efficiency, and device lifetime of the organic electroluminescence devices prepared in Examples 2-1 to 2-33 and Comparative Examples 2-1 to 2-4 were measured. Specifically, the voltage was increased at a rate of 0.1 V / second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescence device reached 3000 cd / m 2 was measured, and at the same time, the current density at this time was measured. The ratio of luminance to current density is the current efficiency. The LT95 lifetime measurement is as follows. Using a luminance meter at a luminance of 5000 cd / m 2 a constant current was maintained, and the time until the luminance of the organic electroluminescence device decreased to 4750 cd / m 2 was measured. The unit is time. The measurement results are shown in Table 2.

Table 2

[0395] As can be seen from the results in Table 2, when the compounds of Examples 2-1 to 2-33 of the present invention are used as the hole transport material of the organic electroluminescence device, when the device luminance reaches 3000 cd / m 2 , the driving voltage is as low as 3.5 V or less, and the current efficiency is as high as 10.5 cd / A or more. LT95 reaches 152 h or more, effectively reducing the driving voltage, improving the current efficiency, and extending the device service life. This is a hole transport material with good performance. In contrast, the compounds used in Comparative Examples 2-1 to 2-4 have various degrees of defects in terms of driving voltage, current efficiency, service life, etc. as the hole transport material of the organic electroluminescence device. The reason is not clear, but it is speculated as follows. In the molecular structures of the compounds EMT-1 and EMT-2 used in Comparative Examples 2-1 and 2-2, R 2is an arylamine group. In the molecular structures of the compounds EMT-3 and EMT-4 used in Comparative Examples 2-3 and 2-4, the arylamine group on the naphthalene ring is not in the ortho position to the naphthyl group. Since none of these compounds meet the limitations of Claim 1 of the present invention, the technical effects of the present invention cannot be achieved.

[0396] Example 2-34 This example provides an organic electroluminescent device, and the specific preparation process is as follows. A glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercially available cleaning agent, washed with deionized water, ultrasonically degreased with an acetone:ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, washed with ultraviolet light and ozone, and a low-energy cation beam was collided with the surface.

[0397] The glass substrate provided with the above anode was placed in a vacuum chamber and evacuated to <1×10 -5 Pa, and HI-3 was vacuum-deposited as a hole injection layer on the anode layer film. The deposition rate was 0.1 nm / s and the deposited film thickness was 10 nm.

[0398] HT-4 was vacuum-deposited as the hole transport layer of the device on the hole injection layer. The deposition rate was 0.1 nm / s and the total deposited film thickness was 80 nm.

[0399] The compound N1 synthesized in Synthesis Example 1 was vacuum-deposited as the electron blocking layer of the device on the hole transport layer. The deposition rate was 0.1 nm / s and the total deposited film thickness was 80 nm.

[0400] The light-emitting layer of the device was vacuum-deposited on the electron blocking layer. The light-emitting layer contains a host material and a dye material. Using the multi-source co-evaporation method, the deposition rate of the host material GPH-59 was adjusted to 0.1 nm / s, the deposition rate of the dye RPD-8 was set at a ratio of 3%, and the total deposited film thickness was 30 nm.

[0401] On the light-emitting layer, the electron transport layer material ET-46 of the device was set at a ratio of 50% and ET-57 was set at a ratio of 50%, and then vacuum deposition was carried out. The deposition rate was 0.1 nm / s and the total deposited film thickness was 30 nm.

[0402] On the electron transport layer (ETL), LiF with a thickness of 0.5 nm was used as the electron injection layer, and an Al layer with a thickness of 150 nm was vacuum deposited as the cathode of the device.

[0403] Examples 2-35 to 2-71 and Comparative Examples 2-5 to 2-8 The production processes of Examples 2-35 to 2-71 and Comparative Examples 2-5 to 2-8 are the same as those of Example 2-34, except that the compound N1 was replaced with the compounds shown in Table 3 as the electron blocking layer material.

[0404] For the organic electroluminescence devices prepared in Examples 2-34 to 2-71 and Comparative Examples 2-5 to 2-8, the following performance measurements were carried out.

[0405] At the same luminance, using a source meter and a luminance meter, the driving voltage, current efficiency, and device lifetime of the organic electroluminescence devices prepared in Examples 2-34 to 2-71 and Comparative Examples 2-5 to 2-8 were measured. Specifically, the voltage was increased at a rate of 0.1 V / second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescence device reaches 3000 cd / m 2 was measured. At the same time, the current density at this time was measured. The ratio of luminance to current density is the current efficiency. The LT95 lifetime measurement is as follows. Using a luminance meter at a luminance of 5000 cd / m 2 a constant current was maintained, and the time until the luminance of the organic electroluminescence device decreased to 4750 cd / m 2 was measured. The unit is time, and the measurement results are shown in Table 3. Table 3 JPEG2025090627000181.jpg241170 JPEG2025090627000182.jpg128170

[0406] From the data in Table 3, when the compounds of Examples 2-34 to 2-71 of the present invention are used as the electron blocking layer material of the organic electroluminescence device, when the device brightness reaches 3000 cd / m 2 , the driving voltage is as low as 3.8 V or less, and the current efficiency is as high as 12.5 cd / A or more. LT95 reaches 167 h or more, which can effectively reduce the driving voltage, improve the current efficiency, and extend the service life of the device. This is an electron blocking layer material with good performance. In contrast, the organic electroluminescence devices using the compounds of Comparative Examples 2-5 to 2-8 as the electron blocking layer material have various degrees of defects in terms of driving voltage, current efficiency, service life, etc. The reason is not clear, but it is speculated as follows. In the molecular structures of the compounds EMT-1 and EMT-2 used in Comparative Examples 2-5 and 2-6, R 2 is an arylamine group. In the molecular structures of the compounds EMT-3 and EMT-4 used in Comparative Examples 2-7 and 2-8, the arylamine group on the naphthalene ring is not ortho to the naphthyl group. None of these compounds meet the limitations of Claim 1 of the present invention and cannot achieve the technical effects of the present invention.

[0407] From the above results, the compound can be used as an HTL (hole transport) material and can also be used as an EBL (electron blocking layer) material in combination with other hole transport materials. When used as a hole transport material, the voltage of all examples decreased significantly, and the performance and lifespan were clearly improved. When used in combination with other hole transport materials as an EBL material, it can be seen that the device voltage of all examples increased slightly, but the efficiency and lifespan of the device were further significantly improved. From the comparison between the molecular structure schematic diagrams of the compounds of the present invention (Figs. 1 and 2) and the molecular structure schematic diagrams of the comparative compounds (Figs. 3 and 4), the ortho-substituted naphthyl binaphthyl compound provided by the present invention retains the large π-plane structure of the comparative example compounds (e.g., EMT-3 to EMT-4), and can effectively change the molecular spatial structure, which is advantageous for improving the molecular packing in the film. Therefore, such a material has higher efficiency compared to the comparative examples. Further Gaussian calculations show that at the same time, by restricting the rotation of the aromatic ring on the N atom due to ortho-substitution, the stability of such a material is improved, so that the material has a longer service life.

[0408] <Device using the compound of Preferred Embodiment Three> Example 3-1 In this example, an organic electroluminescence device was provided, and the specific preparation process is as follows. A glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercially available cleaning agent, washed with deionized water, ultrasonically degreased with an acetone:ethanol mixed solvent, dried in a clean environment until the moisture was completely removed, washed with ultraviolet light and ozone, and a low-energy cation beam was collided with the surface.

[0409] The glass substrate provided with the above anode was placed in a vacuum chamber and evacuated to less than 1×10 -5 Pa, and HI-3 was vacuum deposited as a hole injection layer on the anode layer film. The deposition rate was 0.1 nm / s, and the deposition film thickness was 10 nm.

[0410] On top of the positive hole injection layer, HT-4 was vacuum deposited as the hole transport layer of the device. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 60 nm.

[0411] On top of the hole transport layer, compound T1 was vacuum deposited as the electron blocking layer of the device. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 60 nm.

[0412] On top of the electron blocking layer, the light-emitting layer of the device was vacuum deposited. The light-emitting layer contained a host material and a dye material. Using the multi-source co-deposition method, the deposition rate of the host material GPH-59 was adjusted to 0.1 nm / s, the deposition rate of the dye RPD-8 was set at a ratio of 3%, and the total deposited film thickness was 40 nm.

[0413] On top of the light-emitting layer, the electron transport layer material ET-46 of the device was set at a ratio of 50% and ET-57 was set at a ratio of 50% and vacuum deposited. The deposition rate was 0.1 nm / s, and the total deposited film thickness was 25 nm.

[0414] On top of the electron transport layer (ETL), 0.5 nm thick LiF was used as the electron injection layer, and a 150 nm thick Al layer was vacuum deposited as the cathode of the device.

[0415] Examples 3-2 to 3-25 and Comparative Example 3-1 For the preparation processes of Examples 3-2 to 3-12 and Comparative Example 3-1, except that the electron blocking layer material compound T1 was replaced with the compounds shown in Table 3 respectively, they were the same as those of Example 3-1.

[0416] The structure of the electron blocking layer material of Comparative Example 3-1 is as follows (for details, refer to Patent WO2019 / 004587A1). JPEG2025090627000183.jpg49170

[0417] For the organic electroluminescence device prepared in the above process, the following performance measurements were carried out. At the same luminance, using a PR750-type optical radiometer from Photo Research, an ST-86LA-type luminance meter (Beijing Normal University Optoelectronic Instrument Factory), and a Keithley 4200 measurement system, the driving voltage, current efficiency, and device lifetime of the organic electroluminescent devices prepared in the examples and comparative examples were measured. Specifically, the voltage was increased at a rate of 0.1 V / second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent device reaches 5000 cd / m 2 was measured, and at the same time, the current density at this time was measured. The ratio of luminance to current density is the current efficiency. The lifetime measurement of LT95 is as follows. Using a luminance meter at a luminance of 5000 cd / m 2 , a constant current was maintained, and the time until the luminance of the organic electroluminescent device decreased to 4750 cd / m 2 was measured. The unit is time. Taking the lifetime of Comparative Example 3-1 as 100% of the standard, the others are the ratios to it.

[0418] The measurement results are shown in Table 4.

Table 4

[0419] As can be seen from the results in Table 4, when the compound provided by the present invention is used as the electron blocking layer material of the organic electroluminescent device, when the device luminance reaches 5000 cd / m 2 , the driving voltage is as low as 4.5 - 5.2 V, the current efficiency is 16.4 - 18.3 cd / A, effectively reducing the driving voltage, improving the current efficiency, and extending the service life of the device. This is an electron blocking material with good performance.

[0420] In the electron blocking layer material C1 used in Comparative Example 1-1, the group substituted on the naphthalene ring is phenyl, and since the binaphthyl of the present invention does not exist, the performance of the device in Comparative Example 1-1 is significantly reduced compared with the examples, the driving voltage is as high as 5.5 V, and the current efficiency is only 13 cd / A.

[0421] Obviously, the above embodiments are merely examples given for clear explanation and are not limitations on the embodiments. For those skilled in the art, based on the above description, different forms of changes or modifications can be made. Here, it is impossible and unnecessary to list all the embodiments. The obvious changes or modifications derived therefrom are also within the protection scope created by the present invention.

Claims

1. A compound represented by the following formula (III): Here, formula (A) and formula (B) are condensed at the dotted line position, L １ is a single bond, a substituted or unsubstituted C １ ~C １０ Alkylene group, substituted or unsubstituted C ６ ~C ３０ Arylene group, substituted or unsubstituted C ３ ~C ３０ heteroarylene groups, Ar １ is a substituted or unsubstituted C ６ ~C ３０ Aryl group, substituted or unsubstituted C ３ ~C ３０ is one selected from heteroaryl groups, R １ , R ２ , R ３ , R ４ and R ５ are independently a halogen, an amino group, a cyano group, a nitro group, an ester group, a hydroxyl group, １ ~C １０ Silyl group, substituted or unsubstituted C １ ~C １０ Chain alkyl group, substituted or unsubstituted C ３ ~C １０ Cycloalkyl groups, substituted or unsubstituted C ２ ~C １０ Alkenyl group, substituted or unsubstituted C ２ ~C １０ Alkynyl group, substituted or unsubstituted C １ ~C １０ A chain alkoxy group, substituted or unsubstituted C ３ ~C １０ Cycloalkoxy group, substituted or unsubstituted C ６ ~C ３０ Arylamino group, substituted or unsubstituted C ３ ~C ３０ Heteroarylamino group, substituted or unsubstituted C ６ ~C ３０ Aryl group, substituted or unsubstituted C ３ ~C ３０ is one selected from heteroaryl groups, m is an integer from 0 to 6, and when m is 2 or more, R １ are the same or different, n is an integer from 0 to 7, and when n is 2 or more, R ２ are the same or different, p is an integer from 0 to 2, and when p=2, R ３ are the same or different, q is an integer of 0 to 3, and when q is 2 or more, R ４ are the same or different, s is an integer from 0 to 4, and when s is 2 or more, R ５ are the same or different, When the group has a substituent, the substituent is a halogen, a cyano group, C １ ~C １０ Chain alkyl group, C ３ ~C １０ Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Thioalkoxy group, C ６ ~C ３０ Arylamino group, C ３ ~C ３０ Heteroarylamino group, C ６ ~C ３０ Monocyclic aryl group, C １０ ~C ３０ Fused ring aryl group, C ３ ~C ３０ Monocyclic heteroaryl group, C ６ ~C ３０ The aryl group may be one or a combination of at least two selected from the group consisting of condensed ring heteroaryl groups.

2. It is divided into three types of structures represented by the following formulas (III-1), (III-2), and (III-3): The R ６ is R １ ~R ５ wherein r is an integer of 0 to 6, and when r≧2, R ６ The compound according to claim 1, characterized in that

3. The compound according to claim 1, characterized in that it has a structure represented by the following formula (3-1), in which formula (A-1) and formula (B) are condensed at the dotted line position.

4. They are divided into three types of structures represented by the following formulas (3-1-1), (3-1-2), and (3-1-3): Said L １ , Ar １ , R １ , R ２ , R ６ , R ４ The compound according to claim 3, characterized in that m, n, r, and q each have the same selection range as in formula (3-1).

5. The compound according to claim 1, characterized in that it has a structure represented by the following formula (3-2), in which formula (A-2) and formula (B) are condensed at the dotted line position.

6. They are divided into three types of structures represented by the following formulas (3-2-1), (3-2-2), and (3-2-3): Said L １ , Ar １ , R １ , R ２ , R ６ , R ４ The compound according to claim 5, characterized in that m, n, r, and q each have the same selection range as in formula (3-2).

7. The compound according to claim 5, wherein s, p, n, m, and q are all 0.

8. The compound according to any one of claims 1 to 7, wherein the fluorenyl group and the benzene ring are condensed at position b.

9. Said L １ is selected from a single bond or a substituted or unsubstituted phenylene group; The Ar １ is one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group, Said-L １ -Ar １ is one selected from a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuran group, a dibenzothiophene group, a carbazolyl group, and a phenanthryl group, When the group has a substituent, the substituent is a halogen, a cyano group, C １ ~C １０ Chain alkyl group, C ３ ~C １０ Cycloalkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Thioalkoxy group, C ６ ~C ３０ Arylamino group, C ３ ~C ３０ Heteroarylamino group, C ６ ~C ３０ Monocyclic aryl group, C １０ ~C ３０ Fused ring aryl group, C ３ ~C ３０ Monocyclic heteroaryl group, C ６ ~C ３０ The compound according to any one of claims 1 to 4, which is one or a combination of at least two selected from the group consisting of condensed ring heteroaryl groups.

10. Said L １ The compound according to claim 9, characterized in that: is a single bond.

11. The compound according to claim 1, having a structure represented by T1 to T255.

12. Use of the compound according to any one of claims 1 to 11 in an organic electroluminescence device, a lighting component, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner, electronic paper, or an organic EL panel.

13. Use of the compound according to any one of claims 1 to 11 as a hole transport material or an electron blocking material in an organic electroluminescence device, a lighting member, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner, electronic paper or an organic EL panel.

14. An organic electroluminescence device comprising a substrate, a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the compounds according to any one of claims 1 to 11.

15. The organic electroluminescence device according to claim 14, wherein the organic layer comprises a hole transport region, and the hole transport region comprises the compound according to any one of claims 1 to 11.

16. The organic layer comprises a hole transport region, the hole transport region comprises a hole transport layer and / or an electron blocking layer, and at least one of the hole transport layer and the electron blocking layer comprises the compound according to any one of claims 1 to 11. The organic electroluminescence device according to claim 14.

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