A triarylamine derivative and an organic electroluminescent device thereof

Abstract

The application provides a triarylamine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The application mainly solves the problems that the performance of most hole transport materials is not ideal, the organic electroluminescent device has low luminous efficiency and short service life and the like.The triarylamine derivative shown in formula 1 connects a group containing C, Si and Ge elements through 1, 4 positions, improves the transport efficiency of carriers, thereby obtaining high hole transport efficiency, is applied to a hole transport layer, can improve the luminous efficiency of the device, and can improve the service life of the device, thereby enhancing the durability of the device.The triarylamine derivative and the organic electroluminescent device thereof can be widely applied to the field of information display technology, such as mobile phones, tablet computers, televisions, wearable devices, VR, vehicle displays and tail lights and the like.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a triarylamine derivative and its organic electroluminescent device. Background Technology

[0002] In recent years, organic semiconductor materials have become one of the most active areas in the materials science field. Compared with inorganic semiconductor materials, they possess advantages such as good solubility, high transparency, ease of processing, fast photoelectric response, and potential biocompatibility, making them increasingly important in high-tech fields such as photoelectric conversion and photovoltaic cells. Among them, OLEDs (Organic Light Emitting Diodes) have significant advantages in display and lighting fields due to their simple structure, fast response speed, active light emission, light weight, thinness, diverse emission colors, wide viewing angle, and low energy consumption, attracting widespread attention in technological applications and scientific research.

[0003] With the development of materials for the functional layers of OLED devices, materials with various properties are constantly emerging. To adapt to the diversity of materials, the device structure is also continuously optimized. Based on the number of organic functional layers, the device structure can be simply divided into single-layer, double-layer, triple-layer, and multi-layer devices. Currently, most OLED devices adopt multi-layer sandwich dual-carrier DC injection devices, which are usually composed of a high work function anode indium tin oxide (ITO), a low work function metal cathode, and organic functional layers. The organic functional layers mainly include a hole transport layer (HTL), an emissive layer (EML), and an electron transport layer (ETL). Under the action of an external electric field, electrons and holes generated by the cathode and anode are injected into the intermediate organic thin film layer. The injected electrons and holes migrate to the emissive layer in the electron transport layer and hole transport layer, maximizing their retention in the emissive layer to increase the chance of recombination and form excitons. The excitons then transition back to the ground state through radiation, producing the phenomenon of light emission, i.e., electroluminescence. The energy level from the excited state to the ground state determines the color of the emitted light.

[0004] As one of the most important functional layers in OLED devices, the hole transport layer's fundamental function is to improve the hole transport efficiency within the device and effectively block electrons within the emissive layer, achieving maximum carrier recombination. Simultaneously, it lowers the energy barrier during hole injection, increasing injection efficiency and thus improving device brightness, efficiency, and lifetime. Therefore, excellent hole transport materials should possess good film-forming properties, excellent thermal stability, and suitable HOMO orbital energy levels to ensure effective hole injection and transport between the electrodes and organic functional layers, while also exhibiting high hole mobility. Thus, developing hole transport materials with suitable HOMO orbital energy levels, high hole mobility, and improved thermal stability and film-forming properties through structural adjustments is an urgent task. Summary of the Invention

[0005] To address the problems existing in the prior art, the present invention provides a triarylamine derivative and its organic electroluminescent device.

[0006] This invention provides a triarylamine derivative having the general formula shown in structural formula 1.

[0007]

[0008] Wherein, Ar1 is selected from the group shown in formula a or formula b.

[0009]

[0010] X is selected from C, Si, and Ge; Ra and Rb are independently selected from substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups; R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted alkylsilyl groups, substituted or unsubstituted arylsilyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 aliphatic rings, and fused cycloalkanes of C6-C30 aromatic rings; n3 is selected from 0, 1, 2, or 3; n4 is selected from 0, 1, 2, 3, or 4.

[0011] The Ar2 is selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C2-C30 heteroaryl groups;

[0012] The Ar3 is selected from substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups;

[0013] R1 and R2 are independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted arylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C60 aliphatic ring, and fused cycloalloys of C6-C30 aromatic rings; or, optionally, two adjacent R1s are bonded together to form a substituted or unsubstituted cyclic structure, or optionally, two adjacent R2s are bonded together to form a substituted or unsubstituted cyclic structure; n1 is selected from 0, 1, 2, 3, or 4; n2 is selected from 0, 1, 2, 3, or 4.

[0014] L1, L2, and L3 are independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene groups or substituted or unsubstituted C2-C30 heteroarylene groups.

[0015] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the triarylamine derivative described in the present invention.

[0016] Beneficial effects:

[0017] This invention discloses a triarylamine derivative as shown in Formula 1 and its organic electroluminescent device. By connecting groups containing elements such as C, Si, and Ge at the 1 and 4 positions, it has good hole transport and electron blocking properties. When used in an organic electroluminescent device, the device has excellent photoelectric performance, specifically, high luminous efficiency and long service life. Detailed Implementation

[0018] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0019] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0020] Examples of halogens described in this invention may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0021] In this invention, "C1-C15" in "substituted or unsubstituted C1-C15 alkyl groups" refers to the number of carbon atoms in the unsubstituted alkyl group, excluding the number of carbon atoms in the substituents. Similarly, "C6-C30" in "substituted or unsubstituted C6-C30 aryl groups" refers to the number of carbon atoms in the unsubstituted aryl group, excluding the number of carbon atoms in the substituents. And so on.

[0022] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has 1 to 15 carbon atoms, preferably 1 to 10. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0023] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0024] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group has 3 to 20 carbon atoms, preferably 3 to 15, and even more preferably 3 to 10. Examples of cycloalkyl groups include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, camphenyl, norbornyl, ferruginyl, isocamphenyl, etc.

[0025] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl, polycyclic aryl, and fused-ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, phenanthrene, triphenylene, anthracene, pyrene, fluorenyl, spirodifluorenyl, spiroanthracenefluorenyl, benzo[a]fluorenyl, benzo[a]spirodifluorenyl, etc.

[0026] The heteroaryl group described in this invention refers to a monovalent group in which at least one aromatic carbon atom is replaced by a heteroatom. The heteroaryl group has 2 to 30 carbon atoms, preferably 2 to 15, and even more preferably 2 to 10. The heteroatom includes, but is not limited to, the atoms listed below: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl and fused-ring heteroaryl groups. Examples of heteroaryl groups include, but are not limited to, the groups listed below: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, carbazole, etc.

[0027] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. The term "alkylsilyl" refers to at least one substituent R of a silyl (-SiH3) group.k It is an alkyl group, and the preferred alkylsilyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl, but are not limited thereto; the "arylsilyl" refers to at least one substituent R of the alkyl (-SiH3) group. k It is an aryl group, and preferred arylsilyl groups include triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, etc., but are not limited to these.

[0028] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon atom in an aromatic hydrocarbon molecule. The arylene group has a carbon number of C6 to C30, preferably C6 to C20, and even more preferably C6 to C10. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene groups include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, perylene, pyrene, indene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, etc.

[0029] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The number of carbon atoms in the heteroaryl group is C2 to C30, preferably C2 to C20, and even more preferably C2 to C10. The heteroatom includes, but is not limited to, the following atoms: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of heteroaryl groups include, but are not limited to, the following groups: pyridylene, pyrimidinylene, quinolineylene, isoquinolineylene, furanylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thiophenylene, benzothiophenylene, dibenzothiophenylene, benzodibenzothiophenylene, etc.

[0030] The fused cyclic group of aliphatic and aromatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0031] In the "substituted or unsubstituted" of this invention, "unsubstituted" means that the hydrogen atom on the group is not replaced by any substituent, and "substituted" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different, and the position of the hydrogen atoms replaced by the substituents may be arbitrary.

[0032] The substituted group represented by "substituted or unsubstituted" in the above-mentioned terms is selected from one of the following groups: deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and substituted or unsubstituted benzo[aliphatic]cycloalkyl. For example, the following groups are preferred: deuterium, halogen atom, cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, undecyl, dodecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, fluorenyl, 9,9-dimethylfluorenyl, 9 ,9-Diphenylfluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], spirodifluorenyl, benzo[spirodifluorenyl], dibenzofuranyl, benzo[dibenzofuranyl], dibenzothiopheneyl, benzo[dibenzothiopheneyl], benzo[cyclopropane], benzo[cyclobutane], dihydroindyl, tetrahydronaphthyl, benzo[cycloheptane], benzo[cyclooctyl], indyl, dihydronaphthyl, etc., but not limited to these, and the above substituents can be unsubstituted, partially substituted with deuterium, or completely substituted with deuterium.

[0033] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0034] In this invention, "two adjacent groups bonded together to form a substituted or unsubstituted cyclic structure" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the bonding of adjacent groups can be connected to another ring to form a spirostructure. An example is shown below:

[0035]

[0036] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, phenanthrene, triphenylene, cyclopentane, cyclohexane, cyclopentene, cyclohexene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, but not limited thereto.

[0037] This invention provides a triarylamine derivative having the general structural formula shown in Formula 1.

[0038]

[0039] Wherein, Ar1 is selected from the group shown in formula a or formula b.

[0040]

[0041] X is selected from C, Si, and Ge; Ra and Rb are independently selected from substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups; R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted alkylsilyl groups, substituted or unsubstituted arylsilyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 aliphatic rings, and fused cycloalkanes of C6-C30 aromatic rings; n3 is selected from 0, 1, 2, or 3; n4 is selected from 0, 1, 2, 3, or 4.

[0042] The Ar2 is selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C2-C30 heteroaryl groups;

[0043] The Ar3 is selected from substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups;

[0044] R1 and R2 are independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted arylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C60 aliphatic ring, and fused cycloalloys of C6-C30 aromatic rings; or, optionally, two adjacent R1s are bonded together to form a substituted or unsubstituted cyclic structure, or optionally, two adjacent R2s are bonded together to form a substituted or unsubstituted cyclic structure; n1 is selected from 0, 1, 2, 3, or 4; n2 is selected from 0, 1, 2, 3, or 4.

[0045] The L1, L2, and L3 are independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene groups or substituted or unsubstituted C2-C30 heteroarylene groups.

[0046] Preferably, R1 and R2 are independently selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, and substituted or unsubstituted quinazolinyl; or optionally, two adjacent R1s are bonded together to form a substituted or unsubstituted benzene ring, or optionally, two adjacent R2s are bonded together to form a substituted or unsubstituted benzene ring.

[0047] Preferably, the Ar1 is selected from one of the following groups:

[0048]

[0049] Ra, R b Independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted quinazolinyl;

[0050] R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted nonyl, substituted or unsubstituted decyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyldimethylsilyl, substituted or unsubstituted diphenylmethylsilyl, substituted or unsubstituted dimethylethylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted camphenyl, substituted... The substituted or unsubstituted norbornel group, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclopentane, substituted or unsubstituted benzocyclohexane, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl; in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other; n3 is selected from 0, 1, 2 or 3; n4 is selected from 0, 1, 2, 3 or 4.

[0051] More preferably, the Ar1 is selected from one of the following groups:

[0052]

[0053]

[0054]

[0055]

[0056] R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted camphenyl, substituted or unsubstituted norbornelyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, etc. The substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other;

[0057] The R5 is the same as or different from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted camphenyl, substituted or unsubstituted norbornelyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, etc. The substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other;

[0058] The n3 is selected from 0, 1, 2 or 3; the n4 is selected from 0, 1, 2, 3 or 4; the n5 is selected from 0, 1, 2, 3, 4 or 5; the n6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the n7 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0059] Preferably, the Ar2 is selected from one of the following groups:

[0060]

[0061] Wherein, the R f It is selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted arylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring fused cycloyl group;

[0062] The f1 is selected from 0, 1, 2, 3, 4 or 5;

[0063] f2 is selected from 0, 1, 2, 3 or 4;

[0064] f3 is selected from 0, 1, 2 or 3;

[0065] The f4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0066] The f5 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0067] f6 is selected from 0, 1, or 2;

[0068] The asterisk (*) indicates a binding site with an adjacent atom.

[0069] More preferably, the R f The substituent is selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, deuterated methyl, or substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, trimethylsilyl, triphenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, halogen, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, and when substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

[0070] Preferably, the Ar3 is selected from one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, and substituted or unsubstituted quinazolinyl.

[0071] More preferably, the Ar3 is selected from one of the following groups:

[0072]

[0073] Wherein, the R g It is selected from one or more of deuterium, cyano, halogen, trifluoromethyl, deuterated methyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl, wherein when substituted by multiple substituents, the multiple substituents are the same or different from each other;

[0074] The g1 is selected from 0, 1, 2, 3, 4 or 5;

[0075] The g2 is selected from 0, 1, 2, 3 or 4;

[0076] The g3 is selected from 0, 1, 2, or 3;

[0077] The g4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0078] The g5 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0079] Preferably, L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyreneylene, substituted or unsubstituted pyridylene, or substituted or unsubstituted pyrimidinylene.

[0080] More preferably, L1, L2, and L3 are independently selected from single bonds or one of the following groups:

[0081]

[0082]

[0083] Most preferably, the triarylamine derivative represented by structural formula 1 is selected from one of the structures shown below.

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] The above lists some specific chemical structures of the triarylamine derivatives of structural formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. All triarylamine derivatives based on structural formula 1 with substituents as defined above should be included.

[0103] Furthermore, the present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains a triarylamine derivative of Formula 1 as described in the present invention.

[0104] Preferably, the organic layer includes a hole transport region containing the triarylamine derivative of the present invention.

[0105] Preferably, the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole transport layer being located between the hole injection layer and the cathode, and at least one of the hole injection layer and the hole transport layer containing the triarylamine derivative described in this invention.

[0106] Preferably, the hole transport region includes a hole transport layer, and the hole transport layer contains the triarylamine derivative described in this invention.

[0107] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the second hole transport layer is located between the first hole transport layer and the cathode, and the third hole transport layer is located between the second hole transport layer and the cathode, and at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer contains the triarylamine derivative described in this invention.

[0108] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the cathode, and the second hole transport layer containing the triarylamine derivative described in this invention.

[0109] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the cathode, and the first hole transport layer containing the triarylamine derivative described in this invention.

[0110] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the cathode, and the first hole transport layer and the second hole transport layer containing the triarylamine derivative described in this invention.

[0111] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0112] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic layers and electrodes on both sides of the aforementioned organic electroluminescent device are described below:

[0113] The anode described in this invention can be made of a conductor with a high work function to facilitate hole injection. The materials used for the anode in this invention can include: metals or alloys thereof, metal oxides, multilayer materials, conductive polymers, combinations of metals and oxides, etc., such as nickel (Ni), platinum (Pt), vanadium (V), silver (Ag), gold (Au), zinc oxide (ZnO), indium tin oxide (ITO), indium zinc oxide (IZO), indium oxide (In₂O₃), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polypyrrole, polyaniline, zinc oxide:aluminum (ZnO:Al), etc., but are not limited thereto.

[0114] The cathode described in this invention can be made of a conductor with a high work function to facilitate hole injection. The materials used for the cathode in this invention can include: metals or alloys thereof, multilayer materials, etc., such as silver (Ag), aluminum (Al), magnesium (Mg), tin (Sb), magnesium silver (Mg:Ag), calcium / magnesium (Ca / Mg), etc., but are not limited thereto.

[0115] The hole injection material described in this invention is preferably a material capable of reducing the interfacial barrier between the anode and the hole transport layer. Materials such as those described below include polycyano-conjugated organic compounds, axial alkene compounds, phthalocyanine metal complexes, aromatic amine derivatives, and polymers. Specific examples may include, but are not limited to, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene (HAT-CN), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), 2,2',2''-(cyclopropane-1,2,3-tripyridyl)-tris(2-perfluorophenylacetonitrile), copper phthalocyanine (CuPC), N4,N4'-(biphenyl-4,4'-diacyl)bis(N4,N4',N4'-triphenylbiphenyl-4,4'-diamine) (TPT1), N,N-phenyl-N,N-(9-phenyl-3-carbazolyl)-1,1'-biphenyl-4,4'-diamine, poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrenesulfonic acid) (PSS), etc.

[0116] The hole transport material described in this invention preferably possesses good hole transport capability and good stability. Materials such as aromatic amine derivatives, carbazole derivatives, and polymers are included. Specific examples may include N-([1,1'-biphenyl]-4-yl)-N-(4-(dibenzo[b,d]furan-4-yl)phenyl)dibenzo[b,d]furan-4-amine, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), and N4,N4-di([ [1,1'-biphenyl]-4-yl)-N4'-([1,1':4',1”-terphenyl]-4-yl)-N4'-phenyl-[1,1'-biphenyl]-4,4'-diamine, N,N,N',N'-tetraphenylbiphenyldiamine, 9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), p-phenylenevinylene (PPV), etc., but not limited thereto. The triarylamine derivatives of Formula 1 of the present invention are preferred.

[0117] The light-emitting layer described in this invention may contain only the guest material, or it may be in the form of the guest material being dispersed in the host material, wherein the host material may be composed of one or more materials.

[0118] The main material of the light-emitting layer of the present invention may include fused aromatic ring derivatives, heterocyclic compounds, etc., such as 9,10-bis(2-naphthyl)anthracene (ADN), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 1,3,5-tris(pyrene-1-yl)benzene (TPB3), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 14,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), etc., but is not limited thereto.

[0119] As guest materials for the luminescent layer of the present invention, they may include aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., such as 4,4'-bis(4-(9H-carbazole-9-yl)styryl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenylbenzotetraphenyl (Rubrene), coumarin 545T (C-525T)tris(2-phenyl-3-methylpyridine)iridium (Ir(3mppy)3), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium(III)(Ir(npy)2acac), tris(2-phenylpyridine)iridium(III)(Ir(ppy)3), etc., but are not limited thereto.

[0120] The hole-blocking layer material described in this invention needs to have good hole-blocking ability in order to block holes within the light-emitting layer. Materials such as imidazole derivatives, phenanthroline derivatives, metal complexes, and triazine derivatives are examples. Specific examples may include, but are not limited to, 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphth-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), di(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, etc.

[0121] The electron transport layer material described in this invention preferably possesses good electron transport capability and good stability. Materials such as imidazole derivatives, phenanthroline derivatives, pyridine derivatives, triazine derivatives, quinoline derivatives, oxadiazole derivatives, triazole derivatives, and metal complexes are included. Specific examples may include 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazolium, 2-(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,4-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene, 2-(3-(phenanthroline-9-)... 1,3,5-triazine (-yl)-5-(pyridin-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 1,3,5-tris(4-(pyridin-4-yl)quinoline-2-yl)benzene (TPyQB), 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), lithium 8-hydroxyquinoline (LiQ), etc., but not limited to these.

[0122] The electron blocking layer of this invention preferably uses a material whose absolute value of the difference between the HOMO value of the electron blocking layer and that of the hole transport layer is greater than or equal to 0.07 eV and less than or equal to 0.35 eV. Specific examples may include triarylamine derivatives, spirofluorene derivatives, furan derivatives, etc., such as TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”] The following are examples of amino acids and compounds, but not limited to: [[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, etc.

[0123] The electron injection layer material described in this invention is preferably a material capable of reducing the interfacial barrier between the cathode and the electron transport layer. Materials described below include metals, metal compounds, metal oxides, etc., but are not limited thereto. Specific examples may include magnesium (Mg), rubidium (Rb), lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), rubidium fluoride (RbF), cesium carbonate (Cs₂CO₃), lithium boron oxide (LiBO₂), molybdenum oxide (MoO₃), aluminum oxide (Al₂O₃), vanadium oxide (V₂O₅), etc., but are not limited thereto.

[0124] The capping material described in this invention is preferably a material capable of improving the luminous efficiency of the device. Materials include, but are not limited to, metal compounds, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include aluminum(III)tris(8-hydroxyquinoline) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-bis(9-carbazole)biphenyl (CBP), etc., but are not limited to these.

[0125] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0126] The organic electroluminescent device of this invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, flat-screen TVs, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, etc.

[0127] Synthesis Examples

[0128] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0129] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0130] There are no particular limitations on the preparation method of the triarylamine derivative of structural formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. For example, the triarylamine derivative of structural formula 1 of the present invention can be prepared by the following synthetic route.

[0131]

[0132] X1, X2, and X3 are halogen atoms, which may be the same or different from the halogen atoms described below: I, Br, and Cl.

[0133] Synthesis Examples

[0134] Synthesis Example 1: Preparation of intermediate c-34:

[0135]

[0136] Under nitrogen protection, n-34 (25.70 g, 80.00 mmol), m-34 (12.83 g, 80.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and K2CO3 (22.11 g, 160.00 mmol) were added to a mixed solvent of 480 mL toluene, 160 mL ethanol, and 160 mL water. The mixture was stirred and refluxed for 7 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene / methanol (8:1 v / v) to give intermediate c-34 (22.84 g, 80% yield). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 356.1259 (theoretical value: 356.1270).

[0137] By substituting the raw materials accordingly and following the preparation method for intermediate c-34, intermediate c can be prepared. The raw materials are shown in the table below:

[0138]

[0139]

[0140] Synthesis Example 2: Preparation of Intermediate C-525

[0141]

[0142] Under argon protection, a'-525 (43.00 g, 110.00 mmol) was suspended in 900 mL of diethyl ether and then cooled at -30 to -40 °C. At the same temperature, 96.8 mL of a 2.5 M n-butyllithium solution in hexane was slowly added dropwise, and the mixture was stirred for 5 h after the addition was complete. Then, a diethyl ether solution of b'-525 (20.05 g, 115.50 mmol) was added dropwise at -30 to -40 °C, and the mixture was stirred for 8 h at the same temperature, then allowed to warm to room temperature. After the reaction was complete, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was washed with 800 mL of heptane to give intermediate c-525 (15.05 g, yield 41%); HPLC purity ≥ 99.81%. Mass spectrometry m / z: 333.9426 (theoretical value: 333.9412).

[0143] By substituting the raw materials accordingly, intermediate C can be prepared according to the preparation method of intermediate C-525. The raw materials are shown in the table below:

[0144]

[0145] Synthesis Example 3: Preparation of Intermediate c-602

[0146]

[0147] b'-602 (40.13 g, 150.00 mmol) was dissolved in 750 mL of THF under an Ar atmosphere and then cooled to -78 °C. 112.50 mL (180.00 mmol / 1.6 M in hexane) of n-BuLi was added dropwise at -78 °C, and the mixture was stirred at the same temperature for 60 min. Then, a solution of diethyl ether (500 mL) containing a'-602 (47.39 g, 180.00 mmol) was added dropwise at -78 °C, and the mixture was stirred at the same temperature for 5 h, then allowed to warm to room temperature. After the reaction was complete, the mixture was quenched with a saturated aqueous solution of NH4Cl. After extraction with diethyl ether (3 × 300 mL), the solution was dried over MgSO4, filtered, and then evaporated to dryness. The residue was washed with 1000 mL of heptane to give intermediate M-602 (49.24 g, yield 79%); HPLC purity ≥ 99.63%. Mass spectrometry m / z: 416.0399 (theoretical value: 416.0387).

[0148] Tetrabutylammonium iodide (35.46 g, 110.00 mmol) and tert-butyl hydroperoxide solution (66 mL / 5.5 M in decane, 3.65 mmol) were added to a toluene (800 mL) solution of M-602 (45.70 g, 110.00 mmol). After stirring at room temperature for 10 minutes, the mixture was heated to 90 °C and stirred at this temperature for 30 hours, then cooled to room temperature. The residue was purified by fractional column chromatography after filtration through a short silica pad eluted with dichloromethane (2.8 L), yielding intermediate c-602 (17.74 g, 39% yield); HPLC purity ≥ 99.75%. Mass spectrometry m / z: 414.0217 (theoretical value: 414.0231).

[0149] Synthesis Example 4: Preparation of Compound 10

[0150]

[0151] Preparation of intermediate B-10:

[0152] Under nitrogen protection, a-10 (29.10 g, 60.00 mmol), b-10 (5.59 g, 60.00 mmol), and NaOt-Bu (10.09 g, 105.00 mmol) were dissolved in 525 mL of toluene. Pd2(dba)3 (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 8 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The resulting solid was recrystallized from toluene / methanol (v / v 10:1) to give intermediate B-10 (23.73 g, 73% yield). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 541.2779 (theoretical value: 541.2770).

[0153] Preparation of compound 10:

[0154] Under nitrogen protection, B-10 (21.67 g, 40.00 mmol), c-10 (16.54 g, 40.00 mmol), and NaOt-Bu (6.92 g, 72.00 mmol) were dissolved in 325 mL of toluene. Pd(OAc)₂ (0.13 g, 0.60 mmol) and P(t-Bu)₃ (1.2 mL / 0.5 M toluene, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 9 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The resulting solid was recrystallized from toluene to give compound 10 (22.73 g, yield 65%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 873.3779 (theoretical value: 873.3791). Theoretical elemental content (%) C 65 H 51 NSi: C, 89.30; H, 5.88; N, 1.60. Measured elemental content (%): C, 89.27; H, 5.93; N, 1.58.

[0155] Synthesis Example 5: Preparation of Compound 27

[0156]

[0157] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-27, and c-10 was replaced with an equimolar amount of c-27, yielding compound 27 (19.71 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 693.2839 (theoretical value: 693.2852). Theoretical elemental content (%) C 51 H 39 NSi: C, 88.27; H, 5.66; N, 2.02. Measured elemental content (%): C, 88.24; H, 5.70; N, 2.05.

[0158] Synthesis Example 6: Preparation of Compound 34

[0159]

[0160] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-27, b-10 with an equimolar amount of b-34, and c-10 with an equimolar amount of c-34, yielding compound 34 (19.39 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 663.3272 (theoretical value: 663.3259). Theoretical elemental content (%) C 48 H 37D4NSi: C, 86.83; H, 6.83; N, 2.11. Measured elemental content (%): C, 86.78; H, 6.79; N, 2.08.

[0161] Synthesis Example 7: Preparation of Compound 48

[0162]

[0163] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-48, and c-10 with an equimolar amount of c-48, yielding compound 48 (20.46 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 751.3621 (theoretical value: 751.3634). Theoretical elemental content (%) C 55 H 49 NSi: C, 87.84; H, 6.57; N, 1.86. Measured elemental content (%): C, 87.79; H, 6.61; N, 1.88.

[0164] Synthesis Example 8: Preparation of Compound 60

[0165]

[0166] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-60, and c-10 was replaced with an equimolar amount of c-60, yielding compound 60 (20.05 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 770.3105 (theoretical value: 770.3117). Theoretical elemental content (%) C 56 H 42 N₂Si: C, 87.23; H, 5.49; N, 3.63. Measured elemental content (%): C, 87.20; H, 5.53; N, 3.59.

[0167] Synthesis Example 9: Preparation of Compound 75

[0168]

[0169] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-10, b-10 with an equimolar amount of b-75, and c-10 with an equimolar amount of c-48, yielding compound 75 (19.96 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 817.3179 (theoretical value: 817.3165). Theoretical elemental content (%) C 61 H 43NSi: C, 89.56; H, 5.30; N, 1.71. Measured elemental content (%): C, 89.58; H, 5.26; N, 1.68.

[0170] Synthesis Example 10: Preparation of Compound 89

[0171]

[0172] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-89, and c-10 with an equimolar amount of c-48, yielding compound 89 (19.68 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 702.3431 (theoretical value: 702.3417). Theoretical elemental content (%) C 51 H 30 D9NSi: C, 87.13; H, 6.88; N, 1.99. Measured elemental content (%): C, 87.11; H, 6.92; N, 1.96.

[0173] Synthesis Example 11: Preparation of Compound 96

[0174]

[0175] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-96, and c-10 with an equimolar amount of c-48, yielding compound 96 (20.70 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 749.3490 (theoretical value: 749.3478). Theoretical elemental content (%) C 55 H 47 NSi: C, 88.07; H, 6.32; N, 1.87. Measured elemental content (%): C, 88.09; H, 6.29; N, 1.91.

[0176] Synthesis Example 12: Preparation of Compound 98

[0177]

[0178] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-98, and c-10 with an equimolar amount of c-98, yielding compound 98 (19.71 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 820.3262 (theoretical value: 820.3274). Theoretical elemental content (%) C 60 H 44N₂Si: C, 87.77; H, 5.40; N, 3.41. Measured elemental content (%): C, 87.80; H, 5.36; N, 3.44.

[0179] Synthesis Example 13: Preparation of Compound 104

[0180]

[0181] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-104, and c-10 with an equimolar amount of c-104, yielding compound 104 (19.51 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 773.3431 (theoretical value: 773.3416). Theoretical elemental content (%) C 57 H 39 D4NSi: C, 88.44; H, 6.12; N, 1.81. Measured elemental content (%): C, 88.39; H, 6.08; N, 1.78.

[0182] Synthesis Example 14: Preparation of Compound 107

[0183]

[0184] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-107, and c-10 with an equimolar amount of c-48, yielding compound 107 (20.02 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 769.3153 (theoretical value: 769.3165). Theoretical elemental content (%) C 57 H 43 NSi: C, 88.91; H, 5.63; N, 1.82. Measured elemental content (%): C, 88.86; H, 5.59; N, 1.85.

[0185] Synthesis Example 15: Preparation of Compound 128

[0186]

[0187] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-128, and c-10 with an equimolar amount of c-128, yielding compound 128 (19.77 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 809.3491 (theoretical value: 809.3478). Theoretical elemental content (%) C 60 H47 NSi: C, 88.96; H, 5.85; N, 1.73. Measured elemental content (%): C, 88.94; H, 5.88; N, 1.69.

[0188] Synthetic Example 16: Preparation of Compound 146

[0189]

[0190] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-27, b-10 with an equimolar amount of b-146, and c-10 with an equimolar amount of c-48, yielding compound 146 (20.60 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 857.3492 (theoretical value: 857.3478). Theoretical elemental content (%) C 64 H 47 NSi: C, 89.57; H, 5.52; N, 1.63. Measured elemental content (%): C, 89.62; H, 5.48; N, 1.60.

[0191] Synthesis Example 17: Preparation of Compound 169

[0192]

[0193] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-169, b-10 with an equimolar amount of b-169, and c-10 with an equimolar amount of a-169, yielding compound 169 (23.56 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 997.3548 (theoretical value: 997.3560). Theoretical elemental content (%) C 73 H 51 NSi2: C, 87.82; H, 5.15; N, 1.40. Measured elemental content (%): C, 87.77; H, 5.19; N, 1.38.

[0194] Synthetic Example 18: Preparation of Compound 180

[0195]

[0196] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-180, and c-10 with an equimolar amount of a-169, yielding compound 180 (20.64 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 831.2970 (theoretical value: 831.2957). Theoretical elemental content (%) C 61 H41 NOSi: C, 88.05; H, 4.97; N, 1.68. Measured elemental content (%): C, 88.10; H, 4.93; N, 1.72.

[0197] Synthetic Example 19: Preparation of Compound 187

[0198]

[0199] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-187, and c-10 with an equimolar amount of c-128, yielding compound 187 (20.01 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 757.2819 (theoretical value: 757.2801). Theoretical elemental content (%) C 55 H 39 NOSi: C, 87.15; H, 5.19; N, 1.85. Measured elemental content (%): C, 87.20; H, 5.22; N, 1.81.

[0200] Synthesis Example 20: Preparation of Compound 202

[0201]

[0202] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-48, b-10 with an equimolar amount of b-202, and c-10 with an equimolar amount of c-48, yielding compound 202 (20.62 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 858.3416 (theoretical value: 858.3430). Theoretical elemental content (%) C 63 H 46 N₂Si: C, 88.07; H, 5.40; N, 3.26. Measured elemental content (%): C, 88.12; H, 5.37; N, 3.30.

[0203] Synthesis Example 21: Preparation of Compound 221

[0204]

[0205] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-221, b-10 with an equimolar amount of b-221, and c-10 with an equimolar amount of c-221, yielding compound 221 (19.94 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 655.3253 (theoretical value: 655.3239). Theoretical elemental content (%) C 50H 41 N: C, 91.56; H, 6.30; N, 2.14. Measured element content (%): C, 91.59; H, 6.27; N, 2.16.

[0206] Synthesis Example 22: Preparation of Compound 268

[0207]

[0208] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-268, and c-10 with an equimolar amount of c-268, yielding compound 268 (20.75 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 740.4161 (theoretical value: 740.4148). Theoretical elemental content (%) C 56 H 40 D7N: C, 90.77; H, 7.34; N, 1.89. Measured elemental content (%): C, 90.80; H, 7.31; N, 1.92.

[0209] Synthesis Example 23: Preparation of Compound 293

[0210]

[0211] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-221, b-10 with an equimolar amount of b-293, and c-10 with an equimolar amount of c-48, yielding compound 293 (19.52 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 677.3094 (theoretical value: 677.3083). Theoretical elemental content (%) C 52 H 39 N: C, 92.13; H, 5.80; N, 2.07. Measured element content (%): C, 92.09; H, 5.77; N, 2.10.

[0212] Synthesis Example 24: Preparation of Compound 424

[0213]

[0214] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-221, b-10 with an equimolar amount of b-424, and c-10 with an equimolar amount of c-128, yielding compound 424 (22.09 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 951.4792 (theoretical value: 951.4804). Theoretical elemental content (%) C 73 H61 N: C, 92.07; H, 6.46; N, 1.47. Measured element content (%): C, 92.10; H, 6.44; N, 1.50.

[0215] Synthesis Example 25: Preparation of Compound 427

[0216]

[0217] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-427, and c-10 with an equimolar amount of c-427, yielding compound 427 (20.74 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 835.3937 (theoretical value: 835.3926). Theoretical elemental content (%) C 62 H 49 N3: C, 89.07; H, 5.91; N, 5.03. Measured element content (%): C, 89.10; H, 5.88; N, 5.05.

[0218] Synthesis Example 26: Preparation of Compound 434

[0219]

[0220] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of n-427, b-10 with an equimolar amount of b-434, and c-10 with an equimolar amount of c-128, yielding compound 434 (19.10 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 691.2888 (theoretical value: 691.2875). Theoretical elemental content (%) C 52 H 37 NO: C, 90.27; H, 5.39; N, 2.02. Measured elemental content (%): C, 90.32; H, 5.43; N, 2.03.

[0221] Synthesis Example 27: Preparation of Compound 482

[0222]

[0223] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-221, b-10 with an equimolar amount of b-482, and c-10 with an equimolar amount of c-482, yielding compound 482 (19.96 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 787.3229 (theoretical value: 787.3211). Theoretical elemental content (%) C 58 H37 D4NS: C, 88.40; H, 5.75; N, 1.78. Measured elemental content (%): C, 88.37; H, 5.78; N, 1.82.

[0224] Synthesis Example 28: Preparation of Compound 499

[0225]

[0226] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-499, and c-10 with an equimolar amount of c-499, yielding compound 499 (19.99 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 846.3923 (theoretical value: 846.3912). Theoretical elemental content (%) C 64 H 42 D4N2: C, 90.74; H, 5.95; N, 3.31. Measured elemental content (%): C, 90.69; H, 5.98; N, 3.27.

[0227] Synthesis Example 29: Preparation of Compound 525

[0228]

[0229] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-525, and c-10 was replaced with an equimolar amount of c-525, yielding compound 525 (19.95 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 713.2151 (theoretical value: 713.2138). Theoretical elemental content (%) C 49 H 37 GeN: C, 82.61; H, 5.23; N, 1.97. Measured elemental content (%): C, 82.56; H, 5.19; N, 1.93.

[0230] Synthesis Example 40: Preparation of Compound 560

[0231]

[0232] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-560, b-10 with an equimolar amount of b-293, and c-10 with an equimolar amount of c-525, yielding compound 560 (20.66 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 753.2441 (theoretical value: 753.2451). Theoretical elemental content (%) C 52 H 41GeN: C, 83.00; H, 5.49; N, 1.86. Measured elemental content (%): C, 83.03; H, 5.45; N, 1.88.

[0233] Synthesis Example 41: Preparation of Compound 577

[0234]

[0235] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-577, b-10 with an equimolar amount of b-577, and c-10 with an equimolar amount of c-525, yielding compound 577 (20.65 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 820.2907 (theoretical value: 820.2921). Theoretical elemental content (%) C 57 H 38 D5GeN: C, 83.53; H, 5.90; N, 1.71. Measured elemental content (%): C, 83.48; H, 5.86; N, 1.75.

[0236] Synthesis Example 42: Preparation of Compound 602

[0237]

[0238] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-602, b-10 with an equimolar amount of b-75, and c-10 with an equimolar amount of c-602, yielding compound 602 (21.17 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 913.2752 (theoretical value: 913.2764). Theoretical elemental content (%) C 65 H 45 GeN: C, 85.54; H, 4.97; N, 1.53. Measured element content (%): C, 85.49; H, 5.01; N, 1.50.

[0239] Synthesis Example 43: Preparation of Compound 627

[0240]

[0241] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-627, and c-10 with an equimolar amount of c-627, yielding compound 627 (21.61 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 916.2860 (theoretical value: 916.2873). Theoretical elemental content (%) C 64 H46 GeN2: C, 83.95; H, 5.06; N, 3.06. Measured elemental content (%): C, 83.98; H, 5.10; N, 3.03.

[0242] Synthesis Example 44: Preparation of Compound 632

[0243]

[0244] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of a-632, b-10 with an equimolar amount of b-632, and c-10 with an equimolar amount of c-525, yielding compound 632 (21.88 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 855.2908 (theoretical value: 855.2920). Theoretical elemental content (%) C 60 H 47 GeN: C, 84.32; H, 5.54; N, 1.64. Measured elemental content (%): C, 84.27; H, 5.56; N, 1.69.

[0245] Synthetic Example 45: Preparation of Compound 644

[0246]

[0247] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-644, and c-10 with an equimolar amount of c-644, yielding compound 644 (22.59 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1027.3221 (theoretical value: 1027.3233). Theoretical elemental content (%) C 74 H 51 GeN: C, 86.56; H, 5.01; N, 1.36. Measured element content (%): C, 86.61; H, 4.98; N, 1.40.

[0248] Synthesis Example 46: Preparation of Compound 648

[0249]

[0250] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-648, and c-10 with an equimolar amount of c-525, yielding compound 648 (21.97 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 931.3245 (theoretical value: 931.3233). Theoretical elemental content (%) C 66H 51 GeN: C, 85.17; H, 5.52; N, 1.50. Measured elemental content (%): C, 85.22; H, 5.49; N, 1.54.

[0251] Synthesis Example 47: Preparation of Compound 652

[0252]

[0253] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-48, b-10 with an equimolar amount of b-652, and c-10 with an equimolar amount of c-525, yielding compound 652 (21.98 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 901.2751 (theoretical value: 901.2764). Theoretical elemental content (%) C 64 H 45 GeN: C, 85.35; H, 5.04; N, 1.56. Measured element content (%): C, 85.40; H, 5.01; N, 1.60.

[0254] Synthesis Example 48: Preparation of Compound 685

[0255]

[0256] Following the same preparation method as in Synthesis Example 4, a-10 was replaced with an equimolar amount of c-128, b-10 with an equimolar amount of b-685, and c-10 with an equimolar amount of c-525, yielding compound 685 (20.36 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 760.2539 (theoretical value: 760.2526). Theoretical elemental content (%) C 51 H 30 D7GeNO: C, 80.65; H, 5.84; N, 1.84. Measured elemental content (%): C, 80.70; H, 5.87; N, 1.80.

[0257] Device Examples

[0258] In this invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0259] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was ambient air at room temperature.

[0260] The device was fabricated using a vacuum evaporation system, with continuous evaporation under uninterrupted vacuum conditions. The materials used were housed in separate quartz crucibles containing different evaporation sources, the temperatures of which could be individually controlled. The thermal evaporation rate of organic materials was typically set at 0.1 nm / s, while the evaporation rate of electrode metals ranged from 0.4 to 0.6 nm / s. The prepared glass substrate was then placed in an OLED vacuum coating machine. During the thin film fabrication process, the system vacuum level should be maintained at 5 × 10⁻⁶. -5 Below Pa, organic layers and metal electrodes were deposited by changing the mask. The deposition rate was measured using an Inficon SQM160 quartz crystal film thickness gauge, and the film thickness was measured using a quartz crystal oscillator.

[0261] Red organic electroluminescent device

[0262] Example 1: Fabrication of Organic Electroluminescent Device 1

[0263] ITO is used as the anode on a glass substrate; a hole injection layer of 55 nm F4-TCNQ is vacuum-deposited on the anode; a first hole transport layer of the present invention compound 10 of the present invention is vacuum-deposited on the hole injection layer of 30 nm; a light-emitting layer of MCP:Ir(BT)2(acac) (mixed in a mass ratio of 95%:5%) is vacuum-deposited on the first hole transport layer of 30 nm; an electron transport layer of Alq3 of the present invention is vacuum-deposited on the light-emitting layer of 28 nm; an electron injection layer of Liq of 1.0 nm is vacuum-deposited on the electron transport layer of 1.0 nm; and a cathode of Al of 120 nm is vacuum-deposited on the electron injection layer of 120 nm.

[0264] Examples 2-35: Fabrication of Organic Electroluminescent Devices 2-35

[0265] In Example 1, compound 10 in the first hole transport layer was replaced with compounds 27, 34, 48, 60, 75, 89, 96, 98, 104, 107, 128, 146, 169, 180, 187, 202, 221, 268, 293, 409, 424, 427, 434, 482, 525, 560, 577, 602, 627, 632, 644, 648, 652, and 685, respectively. The other steps remained the same, resulting in organic electroluminescent devices 2-35.

[0266] Comparative Examples 1-3: Fabrication of Comparative Organic Electroluminescent Devices 1-3

[0267] By replacing compound 10 in the first hole transport layer of Example 1 with R-1, R-2, and R-3 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 3 were obtained.

[0268]

[0269] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1 to 35 and Comparative Examples 1 to 3 of the present invention are shown in Table 1.

[0270] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0271]

[0272]

[0273] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0274] As can be seen from Table 1, compared with Comparative Examples 1 to 3, when the triarylamine derivative of Formula 1 of the present invention is used in the first hole transport layer of an organic electroluminescent device, the luminous efficiency and lifespan of the organic electroluminescent device are improved.

[0275] Green organic light-emitting devices

[0276] Example 36: Fabrication of Organic Electroluminescent Device 36

[0277] ITO is used as the anode on a glass substrate; a hole injection layer of 58 nm HAT-CN is vacuum-deposited on the anode; a first hole transport layer of 30 nm NPB is vacuum-deposited on the hole injection layer; compound 10 of the present invention is vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 15 nm; a light-emitting layer of 35 nm BCzPh:TmCzTrz (mixed in a mass ratio of 95%:5%) is vacuum-deposited on the second hole transport layer; an electron transport layer of 25 nm Liq is vacuum-deposited on the light-emitting layer; an electron injection layer of 1.0 nm LiF is vacuum-deposited on the electron transport layer; and a cathode of 120 nm Al is vacuum-deposited on the electron injection layer.

[0278] Examples 37-70: Fabrication of Organic Electroluminescent Devices 37-70

[0279] In Example 36, compound 10 in the second hole transport layer was replaced with compounds 27, 34, 48, 60, 75, 89, 96, 98, 104, 107, 128, 146, 169, 180, 187, 202, 221, 268, 293, 409, 424, 427, 434, 482, 525, 560, 577, 602, 627, 632, 644, 648, 652, and 685, respectively. All other steps remained the same, resulting in organic electroluminescent devices 37–70.

[0280] Example 71: Fabrication of Organic Electroluminescent Device 71

[0281] By replacing compound NPB in the first hole transport layer of Example 36 with compound 75, and replacing compound 10 in the second hole transport layer with compound 75, and keeping the other steps the same, an organic electroluminescent device 71 is obtained.

[0282] Example 72: Fabrication of Organic Electroluminescent Device 72

[0283] By replacing compound NPB in the first hole transport layer of Example 36 with compound 96, and compound 10 in the second hole transport layer with compound 180, and keeping the other steps the same, an organic electroluminescent device 72 is obtained.

[0284] Example 73: Fabrication of Organic Electroluminescent Device 73

[0285] By replacing compound NPB in the first hole transport layer of Example 36 with compound 293, and compound 10 in the second hole transport layer with compound 146, and keeping the other steps the same, an organic electroluminescent device 73 is obtained.

[0286] Example 74: Fabrication of Organic Electroluminescent Device 74

[0287] By replacing compound NPB in the first hole transport layer of Example 36 with compound 10, and replacing compound 10 in the second hole transport layer with compound 75, and keeping the other steps the same, an organic electroluminescent device 74 is obtained.

[0288] Example 75: Fabrication of Organic Electroluminescent Device 75

[0289] By replacing compound NPB in the first hole transport layer of Example 36 with compound 89, and compound 10 in the second hole transport layer with compound 644, and keeping the other steps the same, an organic electroluminescent device 75 is obtained.

[0290] Comparative Examples 4-5: Fabrication of Comparative Organic Electroluminescent Devices 4-5

[0291] By replacing compound 10 in the second hole transport layer of Example 36 with R-4 and R-5 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 4-5 were obtained.

[0292]

[0293] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 36-75 and Comparative Examples 4-5 of this invention are shown in Table 2.

[0294] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0295]

[0296]

[0297] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0298] As shown in Table 2, when the triarylamine derivative of the present invention is applied to organic electroluminescent devices as the second hole transport layer material, the device performance is significantly improved compared to Comparative Examples 4-5, exhibiting advantages such as high luminous efficiency and long lifespan. When the triarylamine derivative of the present invention is applied to organic electroluminescent devices as the first and second hole transport layer materials, both luminous efficiency and lifespan are improved compared to Comparative Examples 4-5. This is because the triarylamine structure in the compound of the present invention is connected to groups containing C, Si, and Ge elements at positions 1 and 4, which improves the carrier transport efficiency. Therefore, when the triarylamine derivative of the present invention is used as a hole transport material in organic electroluminescent devices, the organic electroluminescent devices exhibit high luminous efficiency and long lifespan.

[0299] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A triarylamine derivative, characterized in that, It has a general structural formula as shown in Equation 1. Wherein, Ar1 is selected from the group shown in formula a or formula b. X is selected from Si and Ge, and Ra and R are selected from Si and Ge. b The elements are independently selected from substituted or unsubstituted C1-C10 alkyl groups and substituted or unsubstituted C6-C12 aryl groups; R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, and substituted or unsubstituted C1-C10 alkyl groups; n3 is selected from 0, 1, 2, or 3; n4 is selected from 0, 1, 2, 3, or 4. The Ar2 is selected from one of the following groups: Wherein, the R f It is selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted phenyl. The f1 is selected from 0, 1, 2, 3, 4 or 5; f2 is selected from 0, 1, 2, 3 or 4; f3 is selected from 0, 1, 2 or 3; The f4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; f6 is selected from 0, 1, or 2; The Indicates the binding site with adjacent atoms; The Ar3 is selected from one of the following groups: Wherein, the R g It is selected from one or more of deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, wherein, when substituted by multiple substituents, the multiple substituents are the same as or different from each other. The g1 is selected from 0, 1, 2, 3, 4 or 5; The g2 is selected from 0, 1, 2, 3 or 4; The g4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; R1 and R2 are independently selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl groups; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1, 2, 3 or 4. The L1 is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted pyridylene. The L2 is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene; The L3 is independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted naphthylene; The substituent group represented by "substituted or unsubstituted" is selected from one of the following groups: deuterium, halogen atom, cyano, methyl, ethyl, propyl, butyl. The substituent group can be unsubstituted, partially substituted with deuterium, or completely substituted with deuterium. Furthermore, the triarylamine derivative is not: .

2. The triarylamine derivative according to claim 1, characterized in that, The Ar1 is selected from one of the following groups: Ra, R b Independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; R3 and R4 are independently selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, and substituted or unsubstituted hexyl; in the case of being substituted by multiple substituents, the multiple substituents are the same as or different from each other.

3. The triarylamine derivative according to claim 1, characterized in that, The Ar1 is selected from one of the following groups: R3 and R4 are independently selected from one or more of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, and substituted or unsubstituted hexyl. In the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other. The R5s, whether identical or different, are selected from one or more of hydrogen, deuterium, cyano, halogen, methyl, ethyl, propyl, and butyl. When substituted by multiple substituents, the multiple substituents may be identical or different from each other. The n5 is selected from 0, 1, 2, 3, 4 or 5; the n6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n7 is selected from 0, 1, 2, 3, 4, 5 or 6.

4. The triarylamine derivative according to claim 1, characterized in that, The Ar2 is selected from one of the following groups: Wherein, the R f It is selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl groups.

5. The triarylamine derivative according to claim 1, characterized in that, The Ar3 is selected from one of the following groups: Wherein, the R g It is selected from one or more of deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other.

6. The triarylamine derivative according to claim 1, characterized in that, L1 and L2 are independently selected from single-bonded, substituted or unsubstituted phenylene oxides; L3 is selected from substituted or unsubstituted phenylene oxides.

7. A triarylamine derivative, characterized in that, The triarylamine derivative is selected from one of the structures shown below:

8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, characterized in that, The organic layer contains any one of the triarylamine derivatives according to any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole transport region, a light-emitting layer, an electron transport region, or a capping layer, characterized in that, At least one layer of the hole transport region contains any one of the triarylamine derivatives according to any one of claims 1 to 7.

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