A triarylamine derivative and an organic electroluminescent device thereof

Abstract

The application provides a triarylamine derivative and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. In order to solve the problem of low performance of an organic electroluminescent device in the prior art, the application provides a triarylamine derivative and an organic electroluminescent device thereof. The triarylamine derivative provided by the application has good hole transport capacity, a suitable HOMO energy level, a high glass transition temperature, high thermal stability, good film-forming property and the like. When the triarylamine derivative is applied to an organic electroluminescent device as a hole transport layer material, the energy barrier of holes in the transport process can be reduced, the injection and transport of holes are facilitated, the recombination probability of carriers is improved, the generation of Joule heat in the device is reduced, and the luminous efficiency and service life of the device are improved.

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] Organic light-emitting diodes (OLEDs) are a promising new flat panel display technology that has developed rapidly in recent decades. They are widely used in many fields such as display and lighting. The widespread application of OLEDs is mainly attributed to their advantages such as high efficiency, high brightness, low driving voltage, good flexibility, wide viewing angle, fast response speed, high resolution, and wide range of material selection. Based on these advantages, OLEDs have become a research focus of related industries at home and abroad.

[0003] Organic light-emitting diodes (OLEDs) operate by injecting electrons and holes from the cathode and anode into the organic layer under an applied voltage. These electrons and holes then recombine within the light-emitting layer to generate excitons. When these excitons release energy as light radiation, the OLED exhibits electroluminescence. OLEDs can be structurally classified into single-layer, double-layer, and multilayer devices. Multilayer devices consist of an anode, a cathode, and organic layers. These organic layers include functional layers such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and an electron transport layer. The multilayer structure allows for full utilization of the functions of each organic layer, balancing carrier transport and thus improving the overall performance of the device.

[0004] The development of organic light-emitting diodes (OLEDs) still faces many technical challenges, particularly in improving luminous efficiency and extending lifespan. Hole transport layer materials, as a crucial component for hole transport, play an indispensable role in OLEDs. However, current hole transport layer materials exhibit low HOMO values ​​and triplet energy levels, requiring a larger energy barrier for hole transport; low hole mobility leads to an imbalance between hole and electron transport, reducing the recombination probability of excitons within the emitting layer and lowering device luminous efficiency; low glass transition temperatures reduce device lifespan; and they are prone to crystallization and have poor film-forming properties.

[0005] Therefore, it is particularly important to develop a hole transport material with high hole mobility, good film-forming properties and thermal stability, suitable HOMO energy level and easy carrier transport, so as to obtain organic electroluminescent devices with high luminous efficiency and long lifespan. Summary of the Invention

[0006] To improve the luminous efficiency and lifespan of organic electroluminescent devices, this invention provides a triarylamine derivative and its organic electroluminescent device.

[0007] This invention provides a triarylamine derivative having the structure shown in Formula I.

[0008]

[0009] In Formula I, Ar1 and Ar2 may be the same as or different from each other, and are selected from any one of the following groups substituted by one or more R5: alkyl groups of C1 to C12, aryl groups of C6 to C30, heteroaryl groups of C2 to C30, fused ring groups of aromatic rings of C6 to C30 and aliphatic rings of C3 to C30, or Ar1 and Ar2 may be connected to each other to form substituted or unsubstituted rings;

[0010] The R5s may be the same or different from each other, wherein at least one of the R5s is selected from substituted or unsubstituted silyl groups, and the remainder is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group;

[0011] The Ar3 and Ar4 may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or Ar3 and Ar4 may be connected to each other to form substituted or unsubstituted rings;

[0012] The Ar5 is selected from any one of the following groups;

[0013]

[0014] The z atoms may be the same or different from each other and are selected from CH or N atoms. When z is bonded to other groups, the z atoms are selected from C atoms.

[0015] The t is selected from O, S, N(R) a Any one of the following;

[0016] Q is selected from O, S, C(R) x R y), N(R z Any one of the following;

[0017] The R x R y They may be identical or different from each other, and are selected from any one of the following: hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused-ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R x R y They can connect with each other to form substituted or unsubstituted rings;

[0018] The R a R z They may be the same as or different from each other, and are selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted fused ring of aromatic ring and aliphatic ring of C6-C30, and substituted or unsubstituted C2-C30 heteroaryl;

[0019] The R7 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, and substituted or unsubstituted C2-C30 heteroaryl.

[0020] The c1 is selected from 0, 1, 2, 3, 4 or 5, the c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the c3 is selected from 0, 1, 2, 3 or 4. When there are two or more R7s, the two or more R7s are the same or different from each other, or two adjacent R7s can be connected to each other to form a substituted or unsubstituted ring.

[0021] The R1-R4 may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted fused ring of aromatic ring and aliphatic ring of C6-C30, and substituted or unsubstituted C2-C30 heteroaryl.

[0022] The n1 is selected from 0, 1, 2, 3 or 4, and the n2 is selected from 0, 1, 2 or 3. When there are two or more R1, R2, R3, R4, the two or more R1, R2, R3, R4 are the same or different from each other, or two adjacent R1, R2, R3, R4 can be connected to each other to form a substituted or unsubstituted ring.

[0023] The L1-L3 may be the same as or different from each other, and are selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, divalent C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, and combinations thereof.

[0024] 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 either the anode or the cathode, and the organic layer comprises at least one or more of the triarylamine derivatives.

[0025] Beneficial effects: The triarylamine derivative of Formula I of the present invention has at least one silyl group substituted at the 9-position of the fluorene group, and the triarylamine contains at least two fluorene groups. Compared with triarylamine derivatives without silyl substitution and triarylamine derivatives with only one fluorene group, it has advantages such as suitable HOMO energy level, good hole transport capability, high glass transition temperature, high thermal stability, and good film formation. When used as a hole transport layer material in organic electroluminescent devices, it can reduce the energy barrier of holes during the transport process, which is beneficial to hole injection and transport, increases hole transport capability, increases the recombination probability of charge carriers, increases exciton utilization, reduces the generation of Joule heat inside the device, and thus improves the luminous efficiency and lifespan of the device. Detailed Implementation

[0026] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0027] In the compounds described herein, 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. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0028] In this specification, "*" indicates a portion connected to another substituent.

[0029] 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.

[0030] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent And so on.

[0031] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0032] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but are not limited thereto.

[0033] The alkenyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl or a branched alkenyl, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms. The alkenyl group can be substituted or unsubstituted. Specific examples may include vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, 3-methyl-1-butenyl, allyl, 1-phenylvinyl-1-yl, styryl, etc., but are not limited thereto.

[0034] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule. The cycloalkyl group includes monocyclic, polycyclic, and bridged cycloalkyl groups. Preferably, it has 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0035] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(Rk )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 C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl. 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, substituted or unsubstituted C6-C30 aryl. 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 groups: 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. Preferred substituted silanes include, but are not limited to, trimethylsilane, triethylsilane, tripropylsilane, triisopropylsilane, tri-tert-butylsilane, tert-butyldimethylsilane, ethyldimethylsilane, isopropyldimethylsilane, triphenylsilane, diphenylsilane, and phenylsilane. The aforementioned substituted silanes are preferably trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane, and triphenylsilane, but are not limited to these.

[0036] The aryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, etc. It includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc.

[0037] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, and preferably have 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a] ... Phinyl, o-phenanthroline, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiaazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0038] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably with 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 7 carbon atoms. It can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0039] The fused ring of aromatic and aliphatic 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 C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused ring of aromatic and aliphatic rings can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0040] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, even more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the aforementioned arylene groups, monocyclic arylene groups can be phenylene, etc., but are not limited to these. The arylene group can be substituted or unsubstituted. Polycyclic arylene groups can be biphenylene, terphenylene, tetraphenylene, etc., but are not limited to these. Fused-ring arylene groups can be naphthylene, anthraceneene, phenanthrene, pyrene, fluorene, spirofluorene, triphenylene, perylene, fluorenyl, etc. It includes, but is not limited to, benzo[a]fluorene, spirodifluorene, etc.

[0041] The heteroaryl group described in this invention refers to the general term for a divalent group formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatoms can be one or more of N, O, S, Si, and P, and can be monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroaryl group can be substituted or unsubstituted. Examples may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, thiopheneyl, pyrroloyl, furanyl, pyranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, carbazolyl, benzocarbazolyl, acridineyl, imoxazanyl, thionazanyl, phenazinyl, phenthiazolyl, phenoxazinyl, indolyl, quinolinyl, isoquinolinyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, dibenzothiopheneyl, quinoxolinyl, quinoxolinyl, naphthinyl, purineyl, and phenanthrolineyl.

[0042] The fused ring groups of divalent aromatic and aliphatic rings described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linkage sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the fused ring groups of aromatic and aliphatic rings described above.

[0043] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of the substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.

[0044] The substituents described in the "substituted or unsubstituted" of this invention may be the same as or different from each other, and are selected from any one of deuterium, cyano, nitro, trifluoromethyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, preferably deuterium or cyano. Halogen atoms, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, silyl, C6-C30 aryl, C2-C30 heteroaryl, specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene. alkyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazoleyl, 9-phenylcarbazoleyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocyclopropane Cycloheptenyl, pyrroleyl, furanyl, thiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0045] The term "linked ring formation" as used in this specification refers to two groups linked together by chemical bonds and optionally aromatized. For example, see the following:

[0046]

[0047] In this specification, the rings formed by the linkage can be aromatic or non-aromatic rings, and can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited to these.

[0048] The term "at least one" as used in this invention includes, where permitted, one, two, three, four, or more.

[0049] In this invention, "one or more" includes, where permitted, one, two, three, four, five, six, seven, eight, nine, ten or more.

[0050] This invention provides a triarylamine derivative having the structure shown in Formula I.

[0051]

[0052] In Formula I, Ar1 and Ar2 may be the same as or different from each other, and are selected from any one of the following groups substituted by one or more R5: alkyl groups of C1 to C12, aryl groups of C6 to C30, heteroaryl groups of C2 to C30, fused ring groups of aromatic rings of C6 to C30 and aliphatic rings of C3 to C30, or Ar1 and Ar2 may be connected to each other to form substituted or unsubstituted rings;

[0053] The R5s may be the same or different from each other, wherein at least one of the R5s is selected from substituted or unsubstituted silyl groups, and the remainder is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group;

[0054] The Ar3 and Ar4 may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or Ar3 and Ar4 may be connected to each other to form substituted or unsubstituted rings;

[0055] The Ar5 is selected from any one of the following groups;

[0056]

[0057] The z atoms may be the same or different from each other and are selected from CH or N atoms. When z is bonded to other groups, the z atoms are selected from C atoms.

[0058] The t is selected from O, S, N(R) a Any one of the following;

[0059] Q is selected from O, S, C(R) x R y ), N(R z Any one of the following;

[0060] The R x R y They may be identical or different from each other, and are selected from any one of the following: hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused-ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R x R y They can connect with each other to form substituted or unsubstituted rings;

[0061] The R a R z They may be the same as or different from each other, and are selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted fused ring of aromatic ring and aliphatic ring of C6-C30, and substituted or unsubstituted C2-C30 heteroaryl;

[0062] The R7 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, and substituted or unsubstituted C2-C30 heteroaryl.

[0063] The c1 is selected from 0, 1, 2, 3, 4 or 5, the c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the c3 is selected from 0, 1, 2, 3, 4, 5 or 6. When there are two or more R7s, the two or more R7s are the same or different from each other, or two adjacent R7s can be connected to each other to form a substituted or unsubstituted ring.

[0064] The R1-R4 may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted fused ring of aromatic ring and aliphatic ring of C6-C30, and substituted or unsubstituted C2-C30 heteroaryl.

[0065] The n1 is selected from 0, 1, 2, 3 or 4, and the n2 is selected from 0, 1, 2 or 3. When there are two or more R1, R2, R3, R4, the two or more R1, R2, R3, R4 are the same or different from each other, or two adjacent R1, R2, R3, R4 can be connected to each other to form a substituted or unsubstituted ring.

[0066] The L1-L3 may be the same as or different from each other, and are selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, divalent C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, and combinations thereof.

[0067] Preferably, the Selected from any one of the following groups;

[0068]

[0069]

[0070] The R5s may be the same as or different from each other, wherein at least one of the R5s is selected from substituted or unsubstituted silyl groups, and the remainder is selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, benzothiophene, benzofuranyl, benzocyclopentyl, or benzocyclohexyl.

[0071] The m1 is selected from 1, 2, 3, 4 or 5; the m2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m3 is selected from 1, 2, 3, 4, 5, 6 or 7; the m4 is selected from 1, 2, 3 or 4; the m5 is selected from 1, 2, 3, 4, 5 or 6; the m6 is selected from 1, 2 or 3; when there are two or more R5, the two or more R5 are the same or different from each other.

[0072] R1 and R2 may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzothiophene, benzofuranyl, benzocyclopentyl, or benzocyclohexyl.

[0073] a1 is selected from 0, 1, 2, 3 or 4, and a2 is selected from 0, 1, 2 or 3. When there are two or more R1 and R2, the two or more R1 and R2 are the same or different from each other, or two adjacent R1 and R2 can be connected to each other to form a substituted or unsubstituted ring.

[0074] Preferably, the Selected from any one of the following groups;

[0075]

[0076]

[0077] The *-{Si(Rb)3} is selected from any one of the following groups;

[0078]

[0079] The R9s may be the same as or different from each other, and are selected from any one of the following groups: hydrogen, deuterium, cyano, trifluoromethyl, or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or naphthidyl;

[0080] f1 is selected from 1, 2, 3, 4 or 5; f2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; f3 is selected from 1, 2, 3, 4, 5, 6 or 7; f4 is selected from 1, 2, 3 or 4; f5 is selected from 1, 2, 3, 4, 5 or 6; and f6 is selected from 1, 2 or 3.

[0081] The g1 is selected from 1, 2, 3, 4 or 5; the g2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the g3 is selected from 1, 2, 3, 4, 5, 6 or 7; the g4 is selected from 1, 2, 3 or 4; the g5 is selected from 1, 2, 3, 4, 5 or 6; and the g6 is selected from 1, 2 or 3.

[0082] R1 and R2 may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzothiophene, benzofuranyl, benzocyclopentyl, or benzocyclohexyl.

[0083] a1 is selected from 0, 1, 2, 3 or 4, and a2 is selected from 0, 1, 2 or 3. When there are two or more R1 and R2, the two or more R1 and R2 are the same or different from each other, or two adjacent R1 and R2 can be connected to each other to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

[0084] Preferably, the Selected from any one of the following groups;

[0085]

[0086] R3, R4, and R6 may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzothiophene, benzofuranyl, benzocyclopentyl, or benzocyclohexyl.

[0087] b1 is selected from 0, 1, 2 or 3; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4 or 5; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b6 is selected from 0, 1, 2, 3, 4, 5 or 6; b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When there are two or more R3, R4, R6, the two or more R3, R4, R6 are the same as or different from each other.

[0088] Preferably, the Selected from any one of the following groups;

[0089]

[0090]

[0091] Preferably, the Ar5 is selected from any one of the following groups;

[0092]

[0093]

[0094] The R7s may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopentyl, or benzocyclohexyl.

[0095] The number e1 is selected from 0, 1, 2, 3, 4 or 5; the number e2 is selected from 0, 1, 2, 3 or 4; the number e3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the number e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the number e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the number e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the number e7 is selected from 0, 1, 2, 3, 4, 5 or 6; the number e8 is selected from 0, 1, 2 or 3; and the number e9 is selected from 0, 1 or 2.

[0096] Preferably, L1-L3 are the same or different from each other, and are selected from single bonds or any of the following groups;

[0097]

[0098] The R8 groups may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or naphthidyl;

[0099] The d1 is selected from 0, 1, 2, 3, or 4; the d2 is selected from 0, 1, 2, or 3; the d3 is selected from 0, 1, or 2; the d4 is selected from 0 or 1; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Preferably, the triarylamine derivative is selected from any one of the following structures.

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] The above lists some specific structural forms of the triarylamine derivatives represented by Formula I of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula I, with substituents as defined above, should be included.

[0118] 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 either the anode or the cathode, and the organic layer comprises at least one or more of the triarylamine derivatives.

[0119] Preferably, the organic layer of the present invention is located between the anode and the cathode, and includes at least one of the hole transport region, the light-emitting layer, and the electron transport region.

[0120] Preferably, the hole transport region of the present invention comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0121] Preferably, the hole transport region of the present invention includes a hole transport layer, and the hole transport layer includes at least one or more of the triarylamine derivatives of the present invention.

[0122] Preferably, the hole transport layer of the present invention comprises a first hole transport layer and a second hole transport layer, wherein at least one of the first hole transport layer and the second hole transport layer comprises at least one or more of the triarylamine derivatives of the present invention.

[0123] Preferably, the light-emitting layer of the present invention comprises a host material and a dopant material.

[0124] Preferably, the electron transport region of the present invention comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0125] Preferably, the organic layer is located outside either the anode or the cathode electrode, and the organic layer includes a capping layer.

[0126] 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 functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0127] The anode material described in this invention preferably uses a material with a high energy function, which improves hole injection efficiency. The anode material that can be used in this invention is selected from the following: indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0128] The hole injection layer described in this invention preferably uses a material with good hole-accepting ability. Specific examples of materials that can be used in the hole injection layer of this invention may include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, and phenazine compounds, such as copper phthalocyanine (CuPc), titanium phthalocyanine, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), and N,N,N',N'-tetra(4-methoxyphenyl)biphenyl. Amines such as MeO-TPD, diquinoxolino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), and 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA) are available, but are not limited to these.

[0129] The hole transport layer material described in this invention is preferably a material with high hole mobility. It can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc. Examples of the hole transport layer material include, but are not limited to, the following materials: N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), N,N,N',N'-tetra(3-methylphenyl)-3,3'-dimethylbiphenyldiamine (HMTPD), etc. The triarylamine derivatives described in this invention are preferred.

[0130] The light-emitting layer material of this invention includes a host material and a dopant material. The host material of the light-emitting layer needs to possess bipolar charge transport properties and have suitable energy levels, and is selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-AND), N,N'-bis-(1-naphthyl)-N,N'-bis(2-naphthyl)anthracene (α-AND), and N,N'-bis-(1-naphthyl)-N,N'-bis(2-naphthyl)anthracene (α-AND). Phenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), etc. Besides the above materials and combinations thereof, the host material of the luminescent layer may also include other known materials suitable for use as the luminescent layer, but is not limited thereto. The luminescent layer doping materials of this invention are divided into blue luminescent materials, green luminescent materials, and red luminescent materials. The luminescent layer doping material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials, selected... (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine)(DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(2-hydroxyphenylpyridine)beryllium (Bepp2), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxyiridium (FIrpic), tris(2-phenylpyridine) Iridium(Pyr)3, bis(2-phenylpyridine)iridium(Pyr)2(acac), 9,10-bis[N-(p-tolyl)anilino]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), tris[1-phenylisoquinoline-C2,N]iridium(III)(Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetone)iridium(Ir(piq)2(acac)), etc., but not limited to these.

[0131] The doping ratio of the host material and the guest material in the light-emitting layer of the present invention is determined according to the materials used. The amount of dopant material is preferably 0.1–70% by mass, more preferably 0.1–30% by mass, further preferably 1–30% by mass, even more preferably 1–20% by mass, and particularly preferably 1–10% by mass.

[0132] The hole blocking layer of this invention preferably uses a material with strong hole blocking capability and suitable HOMO / LUMO energy levels. The hole blocking layer material of this invention can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc., but is not limited thereto.

[0133] The electron transport layer material of the present invention is preferably a material with high electron mobility. It can be selected from any one or more of the following structures: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 8-hydroxyquinoline-lithium (Liq), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), and 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but is not limited thereto.

[0134] The electron injection layer material described in this invention is preferably a material with a small barrier difference to the adjacent organic layer material. Specific examples may include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, cesium 8-hydroxyquinoline, 8-hydroxyquinoline aluminum), organometallic salts (metal acetate, metal benzoate, or metal stearate), molybdenum trioxide, aluminum, etc., but are not limited to these.

[0135] The cathode material of the present invention preferably uses a material with a low work function that can promote electron injection into the organic layer, thereby reducing the electron injection barrier. It can be selected from any one or more of the following materials: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0136] The capping layer of this invention is provided on the outside of either the anode or the cathode electrode, and preferably uses a material that can improve the internal optical coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., but is not limited thereto.

[0137] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0138] The organic electroluminescent device of the present invention can be applied using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating.

[0139] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0140] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0141] This invention provides a method for preparing the compound represented by Formula I, but the preparation method of this invention is not limited thereto. The specific synthetic route is shown below:

[0142]

[0143] Wherein, Xa may be the same or different from each other, and is selected from any one of Cl, Br, and I; Ar1-Ar5, R1-R4, L1-L3, and n1-n2 are the same as those defined above.

[0144] Description of raw materials, reagents, and characterization equipment:

[0145] The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; 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 the present invention are of reagent purity.

[0146] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0147] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0148] Synthesis Example 1: Preparation of raw material a-202:

[0149]

[0150] Preparation of intermediate M-202:

[0151] Under nitrogen protection, X-202 (27.50 g, 120 mmol) was dissolved in 300 mL of anhydrous tetrahydrofuran. The solution temperature was maintained at -78 °C. A hexane solution of n-butyllithium (48 mL of 2.5 M n-hexane solution, 120 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred for 30 minutes. Y-202 (12.90 g, 120 mmol) was then dissolved in 200 mL of tetrahydrofuran and slowly added... The reaction mixture was added dropwise, and the reaction solution was stirred at -78°C for 1 hour. Then, dilute hydrochloric acid was added to terminate the reaction. The mixture was extracted with dichloromethane, and the organic phase was dried with anhydrous magnesium sulfate. The mixture was filtered, the solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (petroleum ether: dichloromethane = 8:1) to obtain intermediate M-202 (23.11 g, yield 87%); HPLC purity ≥ 99.79%, mass spectrometry m / z: 221.1224 (theoretical value: 221.1236).

[0152] Preparation of raw material a-202:

[0153] Under nitrogen protection, Z-202 (10.31 g, 95 mmol) dissolved in 120 mL of anhydrous tetrahydrofuran was added to the reaction flask. The solution temperature was maintained at -78 °C. A hexane solution of n-butyllithium (36 mL of 2.5 M hexane solution, 90 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred for 30 minutes. M-202 (19.92 g, 90 mmol) was then dissolved in 90 mL of anhydrous tetrahydrofuran. The reaction solution was slowly added dropwise, and the temperature was raised from -78℃ to 0℃ while stirring. The reaction was then terminated by adding dilute hydrochloric acid. The solution was extracted with dichloromethane, and the organic phase was dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the solution was purified by silica gel column chromatography (n-hexane:ethyl acetate = 10:1) to obtain the starting material a-202 (19.69 g, yield 67%). The HPLC purity was ≥99.83%, and the mass spectrometry m / z was 326.1538 (theoretical value: 326.1522).

[0154] Synthesis Example 2: Preparation of raw material a-211:

[0155]

[0156] Following the same preparation method as in Synthesis Example 1, x-202 was replaced with an equimolar amount of x-211, and z-202 was replaced with an equimolar amount of z-211 to obtain raw material a-211 (15.34 g, 65%) with HPLC purity ≥ 99.85%. Mass spectrometry m / z: 262.0615 (theoretical value: 262.0630).

[0157] Synthesis Example 3: Preparation of raw material a-253:

[0158]

[0159] Following the same preparation method as in Synthesis Example 1, x-202 was replaced with an equimolar amount of x-253, and z-202 was replaced with an equimolar amount of z-253 to obtain raw material a-253 (24.88 g, 68%), with an HPLC purity ≥ 99.79%. Mass spectrometry m / z: 406.1766 (theoretical value: 406.1753).

[0160] Synthesis Example 4: Preparation of raw material a-582:

[0161]

[0162] Following the same preparation method as in Synthesis Example 1, x-202 was replaced with an equimolar amount of x-582, and z-202 was replaced with an equimolar amount of z-582, yielding raw material a-582 (19.40 g, 66%) with an HPLC purity ≥ 99.88%. Mass spectrometry m / z: 326.1542 (theoretical value: 326.1522).

[0163] Synthesis Example 5: Preparation of Compound 3:

[0164]

[0165] Preparation of intermediate A-3:

[0166] Dissolve a-3 (19.60 g, 60 mmol) in 115 mL of anhydrous tetrahydrofuran. Under nitrogen atmosphere, maintain the solution temperature at -78 °C. Slowly add a hexane solution of n-butyllithium (24 mL of 2.5 M hexane solution, 60 mmol) dropwise to the solution. After the addition is complete, stir for 1 hour. Then, dissolve b-3 (21.54 g, 60 mmol) in 75 mL of tetrahydrofuran and add it dropwise. Maintain the reaction solution at -78 °C and stir for 1 hour. Then allow it to reach room temperature and stir overnight. Remove the solvent under reduced pressure. Dissolve the residue in glacial acetic acid (90 mL). Add concentrated hydrochloric acid solution (31%, 9 mL). React the mixture under reflux for 4 hours and stir overnight at 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 by vacuum distillation. The mixture was recrystallized from isopropanol to give A-3 (23.73 g, yield 73%); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 540.1323 (theoretical value: 540.1304).

[0167] Preparation of intermediate B-3:

[0168] Under nitrogen protection, A-3 (21.67 g, 40 mmol), c-3 (10.06 g, 41 mmol), palladium acetate (89.80 mg, 0.4 mmol), P(t-Bu)3 (1.6 mL of 0.5 M toluene solution, 0.8 mmol), sodium tert-butoxide (7.69 g, 80 mmol), and 350 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 5 h. After the reaction was completed, 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, filtered, and the resulting solid was recrystallized from toluene:methanol = 12:1 to give intermediate B-3 (21.95 g, yield 76%); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 721.3545 (theoretical value: 721.3560).

[0169] Preparation of compound 3:

[0170] Under nitrogen protection, B-3 (14.44 g, 20 mmol), d-3 (5.46 g, 20 mmol), Pd2(dba)3 (183 mg, 0.2 mmol), P(t-Bu)3 (0.8 mL of 0.5 M toluene solution, 0.4 mmol), sodium tert-butoxide (3.84 g, 40 mmol), and 200 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 6 h. After the reaction was completed, 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. Crystals were then precipitated by cooling and filtration. The resulting solid was recrystallized from toluene to give compound 3 (14.01 g, yield 78%); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 897.4177 (theoretical value: 897.4186). Theoretical element content (%) C 64 H 59 NSi2: C, 85.57; H, 6.62; N, 1.56. Measured elemental content (%): C, 85.58; H, 6.61; N, 1.54.

[0171] Synthesis Example 6: Preparation of Compound 5:

[0172]

[0173] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-5, b-3 with an equimolar amount of b-5, c-3 with an equimolar amount of c-5, and d-3 with an equimolar amount of d-5, yielding compound 5 (14.82 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 949.4118 (theoretical value: 949.4104). Theoretical elemental content (%) C 71 H 55 NSi: C, 89.74; H, 5.83; N, 1.47. Measured elemental content (%): C, 89.72; H, 5.84; N, 1.50.

[0174] Synthesis Example 7: Preparation of Compound 26:

[0175]

[0176] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-5, c-3 with an equimolar amount of c-26, and d-3 with an equimolar amount of A-26, yielding compound 26 (14.28 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 926.4452 (theoretical value: 926.4469). Theoretical elemental content (%) C 66 H 50 D7NSi2: C, 85.48; H, 6.95; N, 1.51. Analyzed elemental composition (%): C, 85.50; H, 6.94; N, 1.49. Synthesis Example 8: Preparation of Compound 39:

[0177]

[0178] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-39, c-3 with an equimolar amount of c-39, and d-3 with an equimolar amount of d-39, yielding compound 39 (13.50 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 887.3963 (theoretical value: 887.3947). Theoretical elemental content (%) C 66 H 53 NSi: C, 89.25; H, 6.01; N, 1.58. Measured elemental composition (%): C, 89.24; H, 6.03; N, 1.60. Synthesis Example 9: Preparation of Compound 41:

[0179]

[0180] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-41, and d-3 with an equimolar amount of d-41, yielding compound 41 (13.09 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 797.3490 (theoretical value: 797.3478). Theoretical elemental content (%) C 59 H 47 NSi: C, 88.79; H, 5.94; N, 1.76. Measured elemental composition (%): C, 88.80; H, 5.92; N, 1.77. Synthesis Example 10: Preparation of Compound 107:

[0181]

[0182] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-107, c-3 with an equimolar amount of c-41, and d-3 with an equimolar amount of d-41, yielding compound 107 (13.46 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 921.3779 (theoretical value: 921.3791). Theoretical elemental content (%) C 69 H 51 NSi: C, 89.86; H, 5.57; N, 1.52. Measured elemental composition (%): C, 89.87; H, 5.60; N, 1.50. Synthesis Example 11: Preparation of Compound 109:

[0183]

[0184] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-41, and d-3 with an equimolar amount of A-41, yielding compound 109 (14.10 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 869.3858 (theoretical value: 869.3873). Theoretical elemental content (%) C 62 H 55 NSi2: C, 85.57; H, 6.37; N, 1.61. Measured elemental composition (%): C, 85.60; H, 6.35; N, 1.59. Synthesis Example 12: Preparation of Compound 129:

[0185]

[0186] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-5, c-3 with an equimolar amount of c-129, and d-3 with an equimolar amount of A-41, yielding compound 129 (13.97 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 883.4015 (theoretical value: 883.4030). Theoretical elemental content (%) C 63 H 57 NSi2: C, 85.57; H, 6.50; N, 1.58. Measured elemental composition (%): C, 85.60; H, 6.49; N, 1.60. Synthesis Example 13: Preparation of Compound 164:

[0187]

[0188] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-164, and d-3 with an equimolar amount of d-164, yielding compound 164 (14.17 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 919.4559 (theoretical value: 919.4573). Theoretical elemental content (%) C 68 H 61 NSi: C, 88.75; H, 6.68; N, 1.52. Measured elemental composition (%): C, 88.76; H, 6.70; N, 1.51. Synthesis Example 14: Preparation of Compound 184:

[0189]

[0190] Preparation of intermediate A-26:

[0191] Following the same preparation method as A-3 in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-5 to obtain intermediate A-26 (22.54 g, yield 80%); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 468.0922 (theoretical value: 468.0909).

[0192] Preparation of intermediate A1-184:

[0193] Under nitrogen protection, A-26 (48 mmol, 26.97 g), e-184 (48 mmol, 22.95 g), Pd(PPh3)4 (0.48 mmol, 1.85 g), K2CO3 (120.00 mmol, 21.56 g), 200 mL toluene, 80 mL ethanol, and 80 mL water were added to a reaction flask. The mixture was stirred and heated under reflux for 4 h. After the reaction was completed, 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 and dried over anhydrous magnesium sulfate. The filtrate was concentrated by vacuum distillation, cooled to allow crystals to form, filtered, and recrystallized from toluene / ethanol at a ratio of 4:1 to obtain intermediate A1-184 (20.61 g, yield 85%); HPLC purity ≥ 99.73%. Mass spectrometry m / z: 504.1965 (theoretical value: 504.1978). Preparation of compound 184:

[0194] Following the same preparation method as in Synthesis Example 5, A-3 was replaced with an equimolar amount of A1-184, c-3 with an equimolar amount of c-184, and d-3 with an equimolar amount of d-184, yielding compound 184 (13.55 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 927.5137 (theoretical value: 927.5137). Theoretical elemental content (%) C 68 H 61 D4NSi: C, 87.98; H, 7.49; N, 1.51. Measured elemental content (%): C, 87.97; H, 7.50; N, 1.49.

[0195] Synthesis Example 15: Preparation of Compound 202:

[0196]

[0197] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-202, c-3 with an equimolar amount of c-202, and d-3 with an equimolar amount of d-202, yielding compound 202 (12.78 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 874.4169 (theoretical value: 874.4187). Theoretical elemental content (%) C 62 H 50 D5NSi2: C, 85.07; H, 6.91; N, 1.60. Analyzed elemental composition (%): C, 85.10; H, 6.89; N, 1.59. Synthesis Example 16: Preparation of Compound 211:

[0198]

[0199] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-211, c-3 with an equimolar amount of c-41, and d-3 with an equimolar amount of A-41, yielding compound 211 (13.17 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 877.3390 (theoretical value: 877.3376). Theoretical elemental content (%) C 63 H 47 NO2Si: C, 86.17; H, 5.39; N, 1.60. Measured elemental composition (%): C, 86.20; H, 5.40; N, 1.58. Synthesis Example 17: Preparation of Compound 226:

[0200]

[0201] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-41, and d-3 with an equimolar amount of d-226, yielding compound 226 (13.64 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 873.3780 (theoretical value: 873.3791). Theoretical elemental content (%) C 65 H 51 NSi: C, 89.30; H, 5.88; N, 1.60. Measured elemental composition (%): C, 89.28; H, 5.90; N, 1.59. Synthesis Example 18: Preparation of Compound 253:

[0202]

[0203] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-253, c-3 with an equimolar amount of c-41, and d-3 with an equimolar amount of d-41, yielding compound 253 (14.06 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 949.4118 (theoretical value: 949.4104). Theoretical elemental content (%) C 71 H 55 NSi: C, 89.74; H, 5.83; N, 1.47. Measured elemental composition (%): C, 89.76; H, 5.82; N, 1.50. Synthesis Example 19: Preparation of Compound 266:

[0204]

[0205] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-266, and d-3 with an equimolar amount of d-41, yielding compound 266 (14.51 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 873.3781 (theoretical value: 873.3791). Theoretical elemental content (%) C 65 H 51 NSi: C, 89.30; H, 5.88; N, 1.60. Measured elemental composition (%): C, 89.29; H, 5.90; N, 1.58. Synthesis Example 20: Preparation of Compound 331:

[0206]

[0207] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-266, and d-3 with an equimolar amount of A-41, yielding compound 331 (15.14 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 945.4169 (theoretical value: 945.4186). Theoretical elemental content (%) C 68 H 59 NSi2: C, 86.30; H, 6.28; N, 1.48. Measured elemental composition (%): C, 86.28; H, 6.30; N, 1.50. Synthesis Example 21: Preparation of Compound 376:

[0208]

[0209] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-376, and d-3 with an equimolar amount of d-376, yielding compound 376 (12.15 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 749.3467 (theoretical value: 749.3478). Theoretical elemental content (%) C 55 H 47 NSi: C, 88.07; H, 6.32; N, 1.87. Measured elemental composition (%): C, 88.10; H, 6.31; N, 1.88. Synthesis Example 22: Preparation of Compound 442:

[0210]

[0211] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-442, and d-3 with an equimolar amount of d-41, yielding compound 442 (13.89 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 878.4105 (theoretical value: 878.4105). Theoretical elemental content (%) C 65 H 46 D5NSi: C, 88.79; H, 6.42; N, 1.59. Measured elemental composition (%): C, 88.80; H, 6.44; N, 1.60. Synthesis Example 23: Preparation of Compound 443:

[0212]

[0213] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, b-3 with an equimolar amount of b-443, c-3 with an equimolar amount of c-443, and d-3 with an equimolar amount of d-41, yielding compound 443 (14.71 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 954.4770 (theoretical value: 954.4751). Theoretical elemental content (%) C 68 H 50 D9NSi2: C, 85.48; H, 7.17; N, 1.47. Measured elemental content (%): C, 85.50; H, 7.20; N, 1.45.

[0214] Synthesis Example 24: Preparation of Compound 456:

[0215]

[0216] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, b-3 with an equimolar amount of b-5, c-3 with an equimolar amount of c-456, and d-3 with an equimolar amount of A-456, yielding compound 456 (14.84 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 950.4511 (theoretical value: 950.4500). Theoretical elemental content (%) C 68 H 54 D5NSi2: C, 85.84; H, 6.78; N, 1.47. Measured elemental content (%): C, 85.83; H, 6.80; N, 1.48.

[0217] Synthesis Example 25: Preparation of Compound 463:

[0218]

[0219] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-463, and d-3 with an equimolar amount of d-41, yielding compound 463 (14.70 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 929.4436 (theoretical value: 929.4417). Theoretical elemental content (%) C 69 H 59 NSi: C, 89.08; H, 6.39; N, 1.51. Measured elemental composition (%): C, 89.10; H, 6.40; N, 1.48. Synthesis Example 26: Preparation of Compound 467:

[0220]

[0221] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-467, and d-3 with an equimolar amount of d-467, yielding compound 467 (14.14 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 905.4369 (theoretical value: 905.4355). Theoretical elemental content (%) C 67 H 51 D4NSi: C, 88.79; H, 6.56; N, 1.55. Analyzed elemental composition (%): C, 88.80; H, 6.4; N, 1.53. Synthesis Example 27: Preparation of Compound 486:

[0222]

[0223] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-486, b-3 with an equimolar amount of b-5, c-3 with an equimolar amount of c-486, and d-3 with an equimolar amount of d-486, yielding compound 486 (14.41 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 947.3963 (theoretical value: 947.3947). Theoretical elemental content (%) C 71 H 53 NSi: C, 89.93; H, 5.63; N, 1.48. Measured elemental content (%): C, 89.92; H, 5.65; N, 1.50.

[0224] Synthesis Example 28: Preparation of Compound 502:

[0225]

[0226] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-502, c-3 with an equimolar amount of c-502, and d-3 with an equimolar amount of d-502, yielding compound 502 (13.10 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 872.3575 (theoretical value: 872.3587). Theoretical elemental content (%) C 64 H 48 N₂Si: C, 88.03; H, 5.54; N, 3.21. Measured elemental composition (%): C, 88.05; H, 5.56; N, 3.19. Synthesis Example 29: Preparation of Compound 517:

[0227]

[0228] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-517, c-3 with an equimolar amount of c-517, and d-3 with an equimolar amount of d-41, yielding compound 517 (12.95 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 862.3761 (theoretical value: 862.3743). Theoretical elemental content (%) C 63 H 50 N₂Si: C, 87.66; H, 5.84; N, 3.25. Measured elemental composition (%): C, 87.68; H, 5.85; N, 3.23. Synthesis Example 30: Preparation of Compound 524:

[0229]

[0230] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-524, and d-3 with an equimolar amount of d-41, yielding compound 524 (13.71 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 925.3838 (theoretical value: 925.3852). Theoretical elemental content (%) C 67 H 51 N3Si: C, 86.88; H, 5.55; N, 4.54. Measured elemental composition (%): C, 86.90; H, 5.54; N, 4.52. Synthesis Example 31: Preparation of Compound 545:

[0231]

[0232] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-545, and d-3 with an equimolar amount of d-41, yielding compound 545 (14.26 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 913.4115 (theoretical value: 913.4104). Theoretical elemental content (%) C 68 H 55 NSi: C, 89.33; H, 6.06; N, 1.53. Measured elemental composition (%): C, 89.31; H, 6.07; N, 1.50. Synthesis Example 32: Preparation of Compound 563:

[0233]

[0234] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, b-3 with an equimolar amount of b-443, c-3 with an equimolar amount of c-563, and d-3 with an equimolar amount of A-41, yielding compound 563 (14.26 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 959.3966 (theoretical value: 959.3979). Theoretical elemental content (%) C 68 H 57 NOSi2: C, 85.04; H, 5.98; N, 1.46. Measured elemental content (%): C, 85.05; H, 5.97; N, 1.50.

[0235] Synthesis Example 33: Preparation of Compound 573:

[0236]

[0237] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-573, and d-3 with an equimolar amount of d-41, yielding compound 573 (14.06 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 962.4075 (theoretical value: 962.4056). Theoretical elemental content (%) C 71 H 54 N₂Si: C, 88.53; H, 5.65; N, 2.91. Measured elemental composition (%): C, 88.51; H, 5.66; N, 2.89. Synthesis Example 34: Preparation of Compound 576:

[0238]

[0239] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-576, and d-3 with an equimolar amount of d-576, yielding compound 576 (14.25 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 924.4340 (theoretical value: 924.4320). Theoretical elemental content (%) C 66 H 40 D 10 N₂OSi: C, 85.67; H, 6.53; N, 3.03. Analyzed elemental composition (%): C, 85.70; H, 6.49; N, 3.05. Synthesis Example 35: Preparation of Compound 582:

[0240]

[0241] Following the same preparation method as in Synthesis Example 14, a-3 was replaced with an equimolar amount of a-582, e-184 with an equimolar amount of e-528, c-184 with an equimolar amount of c-582, and d-184 with an equimolar amount of d-376, yielding compound 582 (14.26 g); HPLC purity ≥ 99.91. Mass spectrometry m / z: 989.4181 (theoretical value: 989.4197). Theoretical elemental content (%) C 68 H 59 N3OSi2: C, 82.47; H, 6.00; N, 4.24. Measured elemental content (%): C, 82.50; H, 6.01; N, 4.22.

[0242] Synthesis Example 36: Preparation of Compound 593:

[0243]

[0244] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-5, c-3 with an equimolar amount of c-593, and d-3 with an equimolar amount of d-593, yielding compound 593 (12.70 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 857.3246 (theoretical value: 857.3260). Theoretical elemental content (%) C 59 H 47 N3SSi: C, 82.57; H, 5.52; N, 4.90. Measured elemental composition (%): C, 82.60; H, 5.49; N, 4.89. Synthesis Example 37: Preparation of Compound 598:

[0245]

[0246] Following the same preparation method as in Synthesis Example 5, a-3 was replaced with an equimolar amount of a-41, c-3 with an equimolar amount of c-598, and d-3 with an equimolar amount of A-41, yielding compound 598 (14.20 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 909.4173 (theoretical value: 909.4186). Theoretical elemental content (%) C 65 H 59 NSi2: C, 85.76; H, 6.53; N, 1.54. Measured elemental content (%): C, 85.77; H, 6.51; N, 1.56.

[0247] [Device Example 1]

[0248] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0249] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate. HI-1 was deposited as a hole injection layer with a thickness of 10 nm. HT-1 was deposited as a first hole transport layer with a thickness of 20 nm on the hole injection layer. Compound 3 was deposited as a second hole transport layer with a thickness of 50 nm on the first hole transport layer. RH:RD = 97:3 (mass ratio) was deposited as a light-emitting layer with a thickness of 42 nm on the second hole transport layer. ET-1 and Liq (doping mass ratio of 1:1) were deposited as an electron transport layer with a thickness of 30 nm on the light-emitting layer. LiF was deposited as an electron injection layer with a thickness of 1.0 nm on the electron transport layer. Mg:Ag = 1:9 (doping mass ratio of 1:1) was deposited as a cathode with a thickness of 12 nm on the electron injection layer. Finally, CP-1 was deposited as a capping layer with a thickness of 80 nm on the cathode.

[0250]

[0251] [Device Examples 2-33]

[0252] Compound 5, 26, 39, 41, 107, 109, 129, 164, 184, 202, 211, 226, 253, 266, 331, 376, 442, 443, 456, 463, 467, 486, 502, 517, 524, 545, 563, 573, 576, 582, 593, or 598 of the present invention are used to replace compound 3 in device example 1 as the second hole transport layer material. Otherwise, an organic electroluminescent device is prepared using the same preparation method as in device example 1.

[0253] [Comparative Device Examples 1-2]

[0254] The organic electroluminescent device was prepared by replacing compound 3 in device example 1 with either comparative compound 1 or comparative compound 2 as the second hole transport layer material, except that the organic electroluminescent device was prepared by the same preparation method as device example 1.

[0255] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0256] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 1 to 33 of the present invention and Comparative Examples 1 to 2 are shown in Table 1 below.

[0257]

[0258]

[0259] As can be seen from the data results in Table 1, the triarylamine derivative shown in Formula I of this invention, when used as the second hole transport layer material in organic electroluminescent devices, can significantly increase the luminous efficiency and extend the lifespan of the device due to its good hole transport capability and increased exciton recombination probability.

[0260] [Device Example 34]

[0261] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0262] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate. HI-1 was deposited as a hole injection layer with a thickness of 10 nm. Compound 3 was deposited as a hole transport layer with a thickness of 70 nm on the hole injection layer. A GH:GD mixture with a mass ratio of 92:8 (electron emission ratio) was deposited as a light-emitting layer with a thickness of 42 nm on the hole transport layer. ET-1 and Liq (doping mass ratio of 1:1) were deposited as an electron transport layer with a thickness of 30 nm on the light-emitting layer. LiF was deposited as an electron injection layer with a thickness of 1.0 nm on the electron transport layer. Mg:Ag with a mass ratio of 1:9 (doping mass ratio of 1:1) was deposited as a cathode with a thickness of 12 nm on the electron injection layer. Finally, CP-1 was deposited as a capping layer with a thickness of 80 nm on the cathode.

[0263] [Device Examples 35-66]

[0264] Compound 5, 26, 39, 41, 107, 109, 129, 164, 184, 202, 211, 226, 253, 266, 331, 376, 442, 443, 456, 463, 467, 486, 502, 517, 524, 545, 563, 573, 576, 582, 593, or 598 of the present invention are used to replace compound 3 in device example 34 as the hole transport layer material. Otherwise, an organic electroluminescent device is prepared by the same preparation method as device example 34.

[0265] [Comparative Device Examples 3-4]

[0266] The organic electroluminescent device was prepared by replacing compound 3 in device example 34 with either comparative compound 1 or comparative compound 2 as the hole transport layer material, except that the organic electroluminescent device was prepared by the same preparation method as device example 34.

[0267] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 34 to 66 of the present invention and Comparative Examples 3 to 4 are shown in Table 2 below.

[0268]

[0269]

[0270] As can be seen from the data results in Table 2, applying the triarylamine derivative shown in Formula I of the present invention as a hole transport layer material in organic electroluminescent devices can effectively improve the luminous efficiency of the devices and extend their service life.

[0271] 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, The triarylamine derivative has the structure shown in Formula I. In Equation I, the Selected from any one of the following groups; ； The Selected from any one of the following groups; ； The R9s may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl. f1 is selected from 1 or 2, f2 is selected from 1 or 2, f3 is selected from 1 or 2, and f4 is selected from 1 or 2; The g1 is selected from 1, 2, 3, 4 or 5; the g2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the g3 is selected from 1, 2, 3, 4, 5, 6 or 7; and the g4 is selected from 1, 2, 3 or 4. R1 and R2 may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl. a1 is selected from 0, 1, 2, 3 or 4, and a2 is selected from 0, 1, 2 or 3. When there are two or more R1 and R2, the two or more R1 and R2 are the same or different from each other, or two adjacent R1 and R2 can be connected to each other to form substituted or unsubstituted benzene rings. The Selected from any one of the following groups; ； R3 and R4 may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, adamantyl, phenyl. The R6 groups may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl; b1 is selected from 0, 1, 2 or 3; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4 or 5; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b6 is selected from 0, 1, 2, 3, 4, 5 or 6; b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When there are two or more R3, R4, R6, the two or more R3, R4, R6 are the same as or different from each other. The Ar5 is selected from any one of the following groups; ； The R7s may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl. The following values ​​are selected: e1 is 0, 1, 2, 3, 4 or 5; e2 is 0, 1, 2, 3 or 4; e3 is 0, 1, 2, 3, 4, 5, 6 or 7; e4 is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; e5 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; e6 is 0, 1, 2, 3, 4, 5, 6, 7 or 8; e7 is 0, 1, 2, 3, 4, 5 or 6; e8 is 0, 1, 2 or 3; and e9 is 0, 1 or 2. The L1-L3 may be the same as or different from each other, and are selected from single bonds or any of the groups shown below; ； The R8s may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C6 alkyl groups: methyl, ethyl, isopropyl, tert-butyl; The d1 is selected from 0, 1, 2, 3 or 4, the d2 is selected from 0, 1, 2 or 3, and the d3 is selected from 0, 1 or 2.

2. The triarylamine derivative according to claim 1, characterized in that, The Selected from any one of the following groups; 。 3. A triarylamine derivative according to claim 1, characterized in that, The Selected from any one of the following groups; 。 4. A triarylamine derivative according to claim 1, characterized in that, The Selected from any one of the following groups; 。 5. A triarylamine derivative according to claim 1, characterized in that, The Ar5 is selected from any one of the following groups; 。 6. A triarylamine derivative according to claim 1, characterized in that, The L1-L3 may be the same as or different from each other, and are selected from single bonds or any of the groups shown below; 。 7. A triarylamine derivative, characterized in that, The triarylamine derivative is selected from any one of the following structures; 。 8. 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 either the anode or the cathode, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, which includes at least one or more of the triarylamine derivatives according to any one of claims 1 to 7.

Images