Triarylamine derivative and organic electroluminescent device thereof

Abstract

The invention provides a triarylamine derivative and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. The triarylamine derivative provided by the invention has a proper HOMO energy level and good hole mobility, is applied to an organic electroluminescent device as a hole transport layer material or a luminescent layer main body material, has a high energy level matching degree with an adjacent functional layer, can effectively reduce an energy barrier needing to be overcome in a hole transport process, and improves the luminous efficiency of the organic electroluminescent device. The organic light-emitting device prepared by the preparation method is beneficial to hole injection and transmission, increases the recombination probability of excitons in the light-emitting layer, reduces the generation of Joule heat in the device, greatly improves the light-emitting efficiency and prolongs the service life of the organic light-emitting device, and has a good application effect and a good industrialization prospect.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescent materials, and in particular to a triarylamine derivative and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED), also known as organic light-emitting diodes, is widely used in many fields such as display and lighting due to its advantages such as fast response, wide viewing angle, light and thin body, wide operating temperature range, low energy consumption, high clarity, strong flexibility and ability to achieve large-area full-color flat panel display.

[0003] Organic electroluminescent devices are devices in which electrons and holes of organic photoelectric materials are injected and transferred from the cathode and anode to the organic layer respectively under the action of an external electric field, so that the two recombine in the light-emitting layer to produce excitons. Excitons transfer energy to organic light-emitting molecules, causing them to transition from the ground state to the excited state. The excited state molecules are in an unstable state. When the excited molecules return to the ground state from the excited state, the energy is released in the form of light, resulting in luminescence. Organic electroluminescent devices can be divided into single-layer devices, double-layer devices and multi-layer devices according to their structure. Multi-layer devices are composed of an anode, a cathode and an organic layer. The organic layer includes functional layers such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a covering layer.

[0004] As society continues to develop, people's demand for living standards is getting higher and higher, and electronic products have become an indispensable part of human life. However, the current organic electroluminescent devices generally have low luminous efficiency and short service life. For the hole transport region, the HOMO value and triplet energy level are low, which increases the energy barrier that needs to be overcome during hole injection and transport. The hole mobility is low, which reduces the balance of hole and electron injection and transport inside the device, and reduces the recombination probability in the light-emitting layer, resulting in low luminous efficiency; at the same time, the energy level matching between the host material in the light-emitting layer and the adjacent functional layer is low, which limits the injection of holes and electrons. The large difference between the singlet and triplet energy levels increases the energy consumption of the device and reduces the service life of the device; in addition, two or more independent light-emitting parts are connected in series through a charge generation layer (CGL), and the electrons and holes generated by the CGL are respectively injected into adjacent light-emitting units. The conventional n-type doped layer / p-type doped layer serves as a connecting layer between light-emitting units to increase the recombination of holes / electrons into excitons in the light-emitting unit. Therefore, it is crucial to design an organic electroluminescent material that can reduce energy consumption, improve device luminous efficiency, and extend device service life. Summary of the invention

[0005] In order to solve the problem of low performance of organic electroluminescent devices in the prior art, the present invention provides a triarylamine derivative and an organic electroluminescent device thereof.

[0006] The present invention provides a triarylamine derivative, wherein the triarylamine derivative has a structure as shown in Formula I,

[0007]

[0008] In formula I, Ar1 is selected from any one of the groups shown in formula II-1 and formula II-2;

[0009]

[0010] The Ar2 is selected from the group shown in formula III;

[0011] The Y is selected from O, S, N (R c )

[0012] The t and v are the same or different from each other and are selected from CH or N atoms. When t and v are bonded to other groups, the t and v are selected from C atoms;

[0013] The R a , R b The same as or different from each other, and any one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl;

[0014] The R c Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and aliphatic ring of C3-C30, substituted or unsubstituted C2-C30 heteroaryl;

[0015] The R1, R2, and R3 are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0016] The a is selected from 0, 1, 2, 3 or 4, the b is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the c is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 can be connected to form a substituted or unsubstituted ring; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 can be connected to form a substituted or unsubstituted ring; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 can be connected to form a substituted or unsubstituted ring;

[0017] The L is selected from any one of the following groups and combinations thereof;

[0018]

[0019] The x are the same or different from each other and are selected from CH or N atoms. When x is bonded to other groups, the x is selected from C atoms;

[0020] The t1 is selected from any one of O, S, and N(R6);

[0021] Said t2 is selected from CH or N atoms;

[0022] The ring A is selected from substituted or unsubstituted C3-C7 aliphatic rings;

[0023] The m is selected from 1, 2 or 3;

[0024] The R4 and R5 are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0025] The R6 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 C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroaryl;

[0026] 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, 1, 2, 3, 4, 5 or 6, when there are two or more R4, the two or more R4 are the same or different from each other, or two adjacent R4 can be connected to each other to form a substituted or unsubstituted ring; when there are two or more R5, the two or more R5 are the same or different from each other;

[0027] The R x , R y are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring, or R x , R y They may be bonded to each other to form a substituted or unsubstituted ring;

[0028] The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroarylene group and a combination thereof;

[0029] The L2 is selected from any one of the following groups and combinations thereof, which are substituted or unsubstituted by a single bond or one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: phenylene, biphenylene, terphenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, quinazolinylene, quinoxalylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, benzofuranylene, benzothiophenylene, indolylene, benzocyclopentylene, benzocyclohexylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, methylenefluorenylene, phenylfluorenylene, and spirofluorenylene.

[0030] 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 any one of the anode and the cathode, and the organic layer comprises any one or more of the triarylamine derivatives.

[0031] Beneficial effects: The triarylamine derivatives shown in formula I provided by the present invention have high hole mobility, are beneficial to the injection and transmission of holes, increase the effective recombination of excitons in the light-emitting layer, and are applied to organic electroluminescent devices as hole transport layer materials, which can effectively improve the luminous efficiency and service life of the device; in addition, when used as the main material of the light-emitting layer, due to its suitable HOMO energy level and high energy level matching between adjacent functional layers, the energy barrier that holes and electrons need to overcome during the transmission process is effectively reduced, and the generation of Joule heat inside the device is reduced, and a device with high performance is also obtained. DETAILED DESCRIPTION

[0032] The following will be a clear and complete description of the technical solutions in conjunction with the specific embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0033] In the compounds of the present invention, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0034] In the present specification, "*" means a portion connecting to another substituent.

[0035] In this specification, when the position of a substituent on a ring is not fixed, it means that it can be connected to any one of the corresponding optional positions of the ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0036] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.

[0037] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine or iodine.

[0038] The alkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from an alkane molecule, which may be a straight chain alkyl group or a branched chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group may be substituted or unsubstituted. Specific examples may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc., but are not limited thereto.

[0039] The alkenyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from an olefin molecule, which can be a straight chain alkenyl group or a branched chain alkenyl group, 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.

[0040] The cycloalkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group may be substituted or unsubstituted. The cycloalkyl group includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but is not limited thereto.

[0041] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R k )3 groups, wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring. Preferably, each R kThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The number of carbon atoms in the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms in the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 18, and particularly preferably 6 to 12. 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl" refers to a silyl substituted by a substituted or unsubstituted C3-C25 alkyl or aryl group, which is preferably substituted by 3 alkyl groups or 3 aryl groups. Examples of the “substituted or unsubstituted silyl group”, especially the “substituted or unsubstituted C3-C25 silyl group” may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, and the like, but are not limited thereto.

[0042] The aryl group described in the present invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon of the aromatic compound molecule, which can be a monocyclic aromatic group, a polycyclic aromatic group or a condensed aromatic group, 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 aromatic group refers to an aromatic group with only one aromatic ring in the molecule, for example, phenyl, etc., but not limited thereto; the polycyclic aromatic group refers to an aromatic group containing two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, quaterphenyl, etc., but not limited thereto; the condensed aromatic group refers to an aromatic group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, for example, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, The invention also includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, 9,9'-spirobifluorenyl and the like.

[0043] The heteroaryl group of the present invention refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to an O, S, N, Si or P atom, preferably having 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be located on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed ring heteroaryl group. The heteroaryl group may be substituted or unsubstituted. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; the condensed ring heteroaryl groups include quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, The invention also includes benzophenone, phenanthroline, naphthyridinyl, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorenyloxanthryl, spirofluorenylthioanthryl and the like, but is not limited thereto.

[0044] The aliphatic ring described in the present invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably having 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, further preferably 3 to 12 carbon atoms, and more preferably 3 to 7 carbon atoms. It can form a monocyclic hydrocarbon or a polycyclic hydrocarbon, which can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be connected in a variety of ways: two rings in the molecule can share a carbon atom to form a spirocycle; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure.

[0045] The fused ring of the aromatic ring and the aliphatic ring of the present invention refers to a ring formed by condensing one or more aromatic rings and one or more aliphatic rings in a molecule 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, and 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 the aromatic ring and the aliphatic ring 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.

[0046] The arylene group described in the present invention refers to the general term for the divalent group left after two hydrogen atoms are removed from the aromatic core carbon of the aromatic hydrocarbon molecule. It can be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the above-mentioned arylene groups, as a monocyclic arylene group, it can be a phenylene group, etc., but it is not limited to this. The arylene group can be substituted or unsubstituted. As the above-mentioned polycyclic arylene group, it can be a biphenylene group, a terphenylene group, a quaterphenylene group, etc., but it is not limited to this. As the above-mentioned condensed ring arylene group, it can be a naphthylene group, anthrylene group, phenanthrenyl group, pyrenyl group, fluorenyl group, spirofluorenyl group, triphenylene group, perylene group, fluoranthenyl group, fluoranthene group, etc. etc., but not limited thereto.

[0047] The heteroarylene group described in the present invention refers to a general term for a divalent group remaining after removing two hydrogen atoms from the core carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatom may be one or more of N, O, S, Si, and P. It may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a condensed-ring heteroarylene group, preferably having 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, further preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroarylene group may be substituted or unsubstituted. Examples may include pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, thienylene, pyrrolylene, furanylene, pyranylene, oxazolylene, thiazolylene, imidazolylene, benzoxazolylene, benzothiazolylene, benzimidazolylene, carbazolylene, benzocarbazolylene, acridinylene, xanthrenylene, thioanthrenylene, phenazinylene, phenothiazinylene, phenoxazinylene, indolylene, quinolylene, isoquinolylene, benzothienylene, benzofuranylene, dibenzofuranylene, dibenzothienylene, quinoxalylene, quinazolinylene, naphthyridinylene, purinylene, o-phenanthrolineylene, and the like, but are not limited thereto.

[0048] The fused ring group of an aromatic ring and an aliphatic ring described in the present invention refers to a sub-fused ring group of an aromatic ring and an aliphatic ring having two linking positions, i.e., a divalent group. Except that they are divalent groups, the description of the fused ring group of an aromatic ring and an aliphatic ring described above can be applied.

[0049] In the "substituted or unsubstituted" of the present invention, "unsubstituted" means that the hydrogen atom on the group is not replaced by any substituent; "substituted" means that at least one hydrogen atom on the group is replaced by a substituent, and the position of the substitution is not limited. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different.

[0050] The substituents in the "substituted or unsubstituted" of the present invention may be the same or different from each other, and are selected from any one of deuterium, cyano, nitro, trifluoromethyl, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 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, cyano, halogen atoms, trifluoromethyl, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 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. alkyl, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C25 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, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylene, 1,2-dimethyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1 The invention also includes oxadiazole, oxazolyl, thiazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, and the like, but is not limited thereto.

[0051] The term "connected to form a ring" used in the present invention refers to two groups connected to each other by a chemical bond and optionally aromatized. For example:

[0052]

[0053] In the present specification, the ring formed by connection can be an aromatic ring or a non-aromatic ring, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0054] The present invention provides a triarylamine derivative, wherein the triarylamine derivative has a structure as shown in Formula I,

[0055]

[0056] In formula I, Ar1 is selected from any one of the groups shown in formula II-1 and formula II-2;

[0057]

[0058] The Ar2 is selected from the group shown in formula III;

[0059] The Y is selected from O, S, N (R c )

[0060] The t and v are the same or different from each other and are selected from CH or N atoms. When t and v are bonded to other groups, the t and v are selected from C atoms;

[0061] The R a , R b The same as or different from each other, and any one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl;

[0062] The R c Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and aliphatic ring of C3-C30, substituted or unsubstituted C2-C30 heteroaryl;

[0063] The R1, R2, and R3 are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0064] The a is selected from 0, 1, 2, 3 or 4, the b is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the c is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 can be connected to form a substituted or unsubstituted ring; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 can be connected to form a substituted or unsubstituted ring; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 can be connected to form a substituted or unsubstituted ring;

[0065] The L is selected from any one of the following groups and combinations thereof;

[0066]

[0067] The x are the same or different from each other and are selected from CH or N atoms. When x is bonded to other groups, the x is selected from C atoms;

[0068] The t1 is selected from any one of O, S, and N(R6);

[0069] Said t2 is selected from CH or N atoms;

[0070] The ring A is selected from substituted or unsubstituted C3-C7 aliphatic rings;

[0071] The m is selected from 1, 2 or 3;

[0072] The R4 and R5 are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0073] The R6 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 C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroaryl;

[0074] 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, 1, 2, 3, 4, 5 or 6, when there are two or more R4, the two or more R4 are the same or different from each other, or two adjacent R4 can be connected to each other to form a substituted or unsubstituted ring; when there are two or more R5, the two or more R5 are the same or different from each other;

[0075] The R x , R y are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring, or R x , R y They may be bonded to each other to form a substituted or unsubstituted ring;

[0076] The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroarylene group and a combination thereof;

[0077] The L2 is selected from any one of the following groups and combinations thereof, which are substituted or unsubstituted by a single bond or one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: phenylene, biphenylene, terphenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, quinazolinylene, quinoxalylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, benzofuranylene, benzothiophenylene, indolylene, benzocyclopentylene, benzocyclohexylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, methylenefluorenylene, phenylfluorenylene, and spirofluorenylene.

[0078] Preferably, Ar1 is selected from any one of the following groups:

[0079]

[0080]

[0081] The R2 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl or benzothiophenyl;

[0082] wherein a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, a2 is selected from 0, 1, 2, 3, 4 or 5, a3 is selected from 0, 1, 2, 3 or 4, a4 ​​is selected from 0, 1, 2 or 3, a5 is selected from 0, 1, 2, 3, 4, 5 or 6, a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0083] Preferably, Ar2 is selected from any one of the following groups:

[0084]

[0085] The Y is selected from O, S, NR c Any of the following;

[0086] The R cAny one of the following groups selected from hydrogen, deuterium, or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, benzocyclopentyl, benzocyclohexyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0087] The R3 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, benzocyclopentanyl, benzocyclohexanyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0088] The b1 is selected from 0, 1, 2 or 3, the b2 is selected from 0 or 1, the b3 is selected from 0, 1 or 2, the b4 is selected from 0, 1, 2, 3, 4 or 5, the b5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the b6 is selected from 0, 1, 2, 3 or 4.

[0089] Preferably, L is selected from any one of the following groups and combinations thereof;

[0090]

[0091] The R4 and R5 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane;

[0092] The c1 is selected from 0, 1, 2, 3 or 4, the c2 is selected from 0, 1, 2 or 3, the c3 is selected from 0, 1 or 2, the c4 is selected from 0, 1, 2, 3, 4, 5 or 6, the c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the c7 is selected from 0 or 1.

[0093] Preferably, L1 is selected from any one of the following groups and combinations thereof, which are substituted or unsubstituted by a single bond or one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, quinazolinylene, quinoxalylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, benzofuranylene, benzothiophenylene, indolylene, benzocyclopentylene, benzocyclohexylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, methylenefluorenylene, phenylfluorenylene, and spirofluorenylene.

[0094] Preferably, L1 is selected from a single bond or any one of the following groups and combinations thereof;

[0095]

[0096] The R7 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane;

[0097] The e1 is selected from 0, 1, 2, 3 or 4, the e2 is selected from 0, 1, 2 or 3, the e3 is selected from 0, 1 or 2, the e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the e6 is selected from 0 or 1, and the e7 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0098] Preferably, L2 is selected from a single bond or any one of the following groups and combinations thereof;

[0099]

[0100]

[0101] The R8 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane;

[0102] The f1 is selected from 0, 1, 2, 3 or 4, the f2 is selected from 0, 1, 2 or 3, the f3 is selected from 0, 1 or 2, the f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the f6 is selected from 0 or 1.

[0103] Preferably, the triarylamine derivative is selected from any one of the following structures,

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] Some specific structural forms of the triarylamine derivatives represented by Formula I of the present invention are listed above, but the present invention is not limited to these chemical structures listed, and all those based on the structure shown in Chemical Formula I and having substituents as defined above should be included.

[0134] 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 any one of the anode and the cathode, and the organic layer comprises any one or more of the triarylamine derivatives.

[0135] Preferably, the organic layer of the present invention is located between the anode and the cathode, and includes at least one layer of a hole transport region, a light emitting layer, and an electron transport region.

[0136] Preferably, the hole transport region described in the present invention comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and at least one of the hole injection layer, the hole transport layer, and the electron blocking layer comprises any one or more of the triarylamine derivatives described in the present invention.

[0137] Preferably, the hole transport layer described in the present invention comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprises any one or more of the triarylamine derivatives described in the present invention.

[0138] Preferably, the organic layer is located between the anode and the cathode, the organic layer comprises two or more light-emitting parts and a charge generation layer, the first light-emitting part is located between the anode and the cathode, the second light-emitting part is located between the first light-emitting part and the cathode, the charge generation layer is located between the first light-emitting part and the second light-emitting part, and the charge generation layer comprises any one or more of the triarylamine derivatives described in the present invention.

[0139] Preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, and the organic layer includes the P-type charge generation layer, and the P-type charge generation layer includes any one or more of the triarylamine derivatives described in the present invention.

[0140] Preferably, the light-emitting layer of the present invention comprises a host material and a doping material, and the host material comprises any one or more of the triarylamine derivatives of the present invention.

[0141] Preferably, the host material comprises a first host material and a second host material, and at least one of the first host material and the second host material comprises any one or more of the triarylamine derivatives described in the present invention.

[0142] Preferably, the electron transport region of the present invention comprises at least one layer of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0143] Preferably, the organic layer of the present invention is located outside any one of the anode and the cathode, and the organic layer includes a covering layer.

[0144] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic functional layers of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced below:

[0145] The organic electroluminescent device of the present invention is usually formed on a substrate. The substrate may be any substrate that does not change when forming electrodes or organic layers, for example, glass, plastic, polymer film, silicon, etc.

[0146] The anode material of the present invention preferably uses a material with high functional function to improve hole injection efficiency. The anode material that can be used in the present 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.

[0147] The hole injection layer of the present invention preferably uses a material with good hole acceptance ability. Specific examples of hole injection layer materials that can be used in the present invention may include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, phthalocyanine compounds, benzidine compounds, phenazine compounds, etc., but are not limited thereto.

[0148] The hole transport layer material of the present 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, diphenylene diamine derivatives, fluorene derivatives, stilbene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., but not limited thereto. The triarylamine derivative of the present invention is preferred.

[0149] The light-emitting layer material of the present invention includes a main material and a doping material. The main material of the light-emitting layer needs to have bipolar charge transport properties and a suitable energy level, and is selected from 4,4'-di(9-carbazole)biphenyl (CBP), 9,10-di(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)di-9H-carbazole (mCP), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), 9,10-di(1- In addition to the above materials and their combinations, the main material of the light-emitting layer may include other known materials suitable for the light-emitting layer, but is not limited thereto. The triarylamine derivatives described in the present invention are preferred.

[0150] The light-emitting layer doping material of the present invention is divided into a blue light-emitting material, a green light-emitting material and a red light-emitting material. The light-emitting layer doping material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials, selected from 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), bis(4,6-difluorophenylpyridine-C2,N)picolinyliridium (FIr pic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)anilino]anthracene (TPA), tris[1-phenylisoquinoline-C2,N]iridium (III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), etc., but are not limited thereto.

[0151] The hole blocking layer of the present invention preferably uses a material with strong hole blocking ability and suitable HOMO / LUMO energy levels. The hole blocking layer material of the present 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, phenanthroline derivatives, azobenzene derivatives, anthrone derivatives, etc., but not limited thereto.

[0152] The charge generation layer materials of the present invention include n-type charge generation materials and p-type charge generation materials.

[0153] The n-type charge generation material of the present invention can be selected from the following materials or one of their combinations: tris-(8-hydroxyquinolinate)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, quinoline lithium (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinate-N1,O8)-(1,1'-biphenyl-4-phenolate)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3 -(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tri(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tri(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alternating-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ) and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), the fluorene compounds described in the present invention, etc., but are not limited thereto. In addition, an auxiliary N-type charge generation material may also be included. For example, the auxiliary N-type charge generation material may be an alkali metal, such as Li, Cs, K, Rb, Na, or Fr, etc., but not limited thereto, or an alkaline earth metal, such as Be, Mg, Ca, Sr, Ba, or Ra, etc., but not limited thereto.

[0154] The p-type charge generation material of the present invention may include one of the following materials or a combination thereof: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl) -1,1'-biphenyl-4,4"-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonate (PEDOT / PSS) and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, etc., but not limited thereto. The triarylamine derivatives described in the present invention are preferred.

[0155] 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), 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 not limited thereto.

[0156] The electron injection layer material described in the present invention is preferably a material having a smaller difference in potential barrier with the adjacent organic layer material. Specific examples may include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, 8-hydroxyquinoline cesium, 8-hydroxyquinoline aluminum), organic metal salts (metal acetates, metal benzoates or metal stearates), molybdenum trioxide, metal aluminum, etc., but are not limited thereto.

[0157] 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 to reduce 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., a mixture of Ag and Mg), but is not limited thereto.

[0158] The covering layer of the present invention is provided on the outside of any one of the anode and the cathode, and preferably uses a material that can improve the light coupling efficiency inside 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 not limited thereto.

[0159] The present invention has no special limitation on the thickness of each organic layer of the organic electroluminescent device, and the thickness commonly used in the art can be adopted.

[0160] The organic electroluminescent device of the present invention can be produced by any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slit coating and dip coating.

[0161] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type or a bidirectional-emitting type.

[0162] The organic electroluminescent device of the present invention can be widely used in the fields of panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, signboard, signal lamp, etc.

[0163] The present invention provides a method for preparing a compound represented by formula I, which is prepared by a carbon-nitrogen coupling reaction well known in the art, but the preparation method of the present invention is not limited thereto. The structure of formula I can be prepared by the following reaction route (1) or (2):

[0164]

[0165] Among them, X a are the same as or different from each other and are selected from any one of Cl, Br, and I; the definitions of Ar1, Ar2, L1, L2, L, R1, t, and a are the same as above.

[0166] The present invention can bond the above-mentioned substituents by methods known in the art, and the type and position of the substituents or the number of the substituents can be changed according to techniques known in the art.

[0167] By the following examples, the present invention is explained in more detail, but it is not intended to limit the present invention. On the basis of this description, those of ordinary skill in the art will be able to implement the present invention and prepare other compounds and devices according to the present invention within the entire disclosed range without paying creative work.

[0168] Preparation and characterization of compounds

[0169] Description of raw materials, reagents and characterization equipment:

[0170] The present invention has no particular restrictions on the sources of the raw materials and reagents used in the following examples, and they can be commercially available products or prepared by preparation methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0171] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0172] The elemental analysis used the Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg;

[0173] Synthesis Example 1: Preparation of Compound 5:

[0174]

[0175] Preparation of intermediate A-5

[0176] Under nitrogen protection, a-5 (20.07 g, 60.00 mmol), b-5 (23.84 g, 60.00 mmol), Pd(OAc)2 (0.18 g, 0.80 mmol), P(t-Bu)3 (3.20 mL of 0.5 M toluene solution, 1.60 mmol), NaOt-Bu (11.53 g, 120.00 mmol) and 300 ml of toluene solvent were added to the reaction bottle, and the mixture was stirred. The mixed solution of the above reactants was heated to reflux for 5.0 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and the liquid was separated by standing. The organic layer was collected and dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The temperature was lowered for crystallization, and suction was filtered. The obtained solid was recrystallized with toluene: ethanol = 8:1 to obtain intermediate A-5 (30.07 g, yield 77%), HPLC purity ≧ 99.81%. Mass spectrum m / z: 650.2709 (theoretical value: 650.2722).

[0177] Preparation of compound 5:

[0178] Under nitrogen protection, intermediate A-5 (19.52 g, 30.00 mmol), c-5 (8.19 g, 30.00 mmol), Pd2(dba)3 (0.40 g, 0.44 mmol), BINAP (0.55 g, 0.88 mmol), NaOt-Bu (5.77 g, 60.00 mmol) and 150 ml toluene solvent were added, and the mixture was stirred. The mixed solution of the above reactants was heated to reflux for 3.5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and the liquid was separated by standing. The organic layer was collected and dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and suction was filtered. The obtained solid was recrystallized with toluene to obtain compound 5 (18.72 g, yield 74%), HPLC purity ≧99.90%. Mass spectrum m / z: 842.3420 (theoretical value: 842.3409). Theoretical element content (%) C 62 H 42 N4: C, 88.33; H, 5.02; N, 6.65. Measured element content (%): C, 88.29; H, 5.05; N, 6.68.

[0179] Synthesis Example 2: Preparation of Compound 66:

[0180]

[0181] According to the same preparation method as in Synthesis Example 1, c-5 was replaced with an equal molar amount of c-66 to obtain compound 66 (17.97 g), HPLC purity ≧99.93%. Mass spectrum m / z: 767.2950 (theoretical value: 767.2937). Theoretical element content (%) C 56 H 37 N3O: C, 87.59; H, 4.86; N, 5.47. Measured element content (%): C, 87.61; H, 4.83; N, 5.49.

[0182] Synthesis Example 3: Preparation of Compound 81:

[0183]

[0184] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-81, and c-5 was replaced by an equal mole of c-66 to obtain compound 81 (19.50 g), HPLC purity ≧99.94%. Mass spectrum m / z: 843.3262 (theoretical value: 843.3250). Theoretical element content (%) C 62 H 41 N3O: C, 88.23; H, 4.90; N, 4.98. Measured element content (%): C, 88.20; H, 4.88; N, 4.99.

[0185] Synthesis Example 4: Preparation of Compound 150:

[0186]

[0187] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-150, and c-5 was replaced by an equal mole of c-150 to obtain compound 150 (16.85 g), HPLC purity ≧99.96%. Mass spectrum m / z: 719.2922 (theoretical value: 719.2937). Theoretical element content (%) C 52 H 37 N3O: C, 86.76.; H, 5.18; N, 5.84. Measured element content (%): C, 86.79; H, 5.14; N, 5.87.

[0188] Synthesis Example 5: Preparation of Compound 227:

[0189]

[0190] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-227, b-5 was replaced by an equal mole of b-227, and c-5 was replaced by an equal mole of c-227 to obtain compound 227 (17.59 g), HPLC purity ≧99.95%. Mass spectrum m / z: 802.3699 (theoretical value: 802.3689). Theoretical element content (%) C 58 H 34 D7N3O: C, 86.75; H, 6.02; N, 5.23. Measured element content (%): C, 86.72; H, 6.05; N, 5.22. Synthesis Example 6: Preparation of Compound 268:

[0191]

[0192] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-150, and c-5 was replaced by an equal mole of c-268 to obtain compound 268 (17.67 g), HPLC purity ≧99.96%. Mass spectrum m / z: 795.3238 (theoretical value: 795.3250). Theoretical element content (%) C 58 H 41 N3O: C, 87.52; H, 5.19; N, 5.28. Measured element content (%): C, 87.49; H, 5.21; N, 5.30.

[0193] Synthesis Example 7: Preparation of Compound 330:

[0194]

[0195] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-330, b-5 was replaced by an equal mole of b-330, and c-5 was replaced by an equal mole of c-150 to obtain compound 330 (17.77 g), HPLC purity ≧99.90%. Mass spectrum m / z: 845.3417 (theoretical value: 845.3406). Theoretical element content (%) C 62 H 43 N3O: C, 88.02; H, 5.12; N, 4.97. Measured element content (%): C, 88.04; H, 5.09; N, 4.96. Synthesis Example 8: Preparation of Compound 350:

[0196]

[0197] According to the same preparation method as in Synthesis Example 1, c-5 was replaced with an equal molar amount of c-150 to obtain compound 350 (20.00 g), HPLC purity ≧99.93%. Mass spectrum m / z: 843.3268 (theoretical value: 843.3250). Theoretical element content (%) C 62 H 41 N3O: C, 88.23; H, 4.90; N, 4.98. Measured element content (%): C, 88.19; H, 4.93; N, 4.96.

[0198] Synthesis Example 9: Preparation of Compound 368:

[0199]

[0200] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-368, and c-5 was replaced by an equal mole of c-150 to obtain compound 368 (20.52 g), HPLC purity ≧99.95%. Mass spectrum m / z: 899.3885 (theoretical value: 899.3876). Theoretical element content (%) C 66 H 49 N3O: C, 88.07; H, 5.49; N, 4.67. Measured element content (%): C, 88.10; H, 5.51; N, 4.65.

[0201] Synthesis Example 10: Preparation of Compound 420:

[0202]

[0203] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-420, b-5 was replaced by an equal mole of b-420, and c-5 was replaced by an equal mole of c-150 to obtain compound 420 (19.36 g), HPLC purity ≧99.94%. Mass spectrum m / z: 848.3550 (theoretical value: 848.3563). Theoretical element content (%) C 62 H 36 D5N3O: C, 87.71; H, 5.46; N, 4.95. Measured element content (%): C, 87.68H, 5.44; N, 4.93. Synthesis Example 11: Preparation of Compound 475:

[0204]

[0205] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-475, and c-5 was replaced by an equal mole of c-150 to obtain compound 475 (17.05 g), HPLC purity ≧99.96%. Mass spectrum m / z: 767.2927 (theoretical value: 767.2937). Theoretical element content (%) C 56 H 37 N3O: C, 87.59; H, 4.86; N, 5.47. Measured element content (%): C, 87.61; H, 4.83; N, 5.50.

[0206] Synthesis Example 12: Preparation of Compound 531:

[0207]

[0208] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal molar amount of a-475, b-5 was replaced by an equal molar amount of b-531, and c-5 was replaced by an equal molar amount of c-531 to obtain compound 531 (18.53 g), HPLC purity ≧99.93%. Mass spectrum m / z: 857.3419 (theoretical value: 857.3406). Theoretical element content (%) C 63 H 43 N3O: C, 88.19; H, 5.05; N, 4.90. Measured element content (%): C, 88.22; H, 5.07; N, 4.88. Synthesis Example 13: Preparation of Compound 545:

[0209]

[0210] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-545, b-5 was replaced by an equal mole of b-545, and c-5 was replaced by an equal mole of c-150 to obtain compound 545 (18.51 g), HPLC purity ≧99.91%. Mass spectrum m / z: 844.3216 (theoretical value: 844.3202). Theoretical element content (%) C 61 H 40 N4O: C, 86.70; H, 4.77; N, 6.63. Measured element content (%): C, 86.68; H, 4.75; N, 6.65. Synthesis Example 14: Preparation of Compound 547:

[0211]

[0212] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-547, and c-5 was replaced by an equal mole of c-150 to obtain compound 547 (16.53 g), HPLC purity ≧99.94%. Mass spectrum m / z: 775.3422 (theoretical value: 775.3439). Theoretical element content (%) C 56 H 29 D8N3O: C, 86.68; H, 5.84; N, 5.42. Measured element content (%): C, 86.70; H, 5.82; N, 5.45.

[0213] Synthesis Example 15: Preparation of Compound 556:

[0214]

[0215] According to the same preparation method as in Synthesis Example 1, c-5 was replaced with an equal molar amount of c-556 to obtain compound 556 (19.31 g), HPLC purity ≧99.92%. Mass spectrum m / z: 857.3420 (theoretical value: 857.3406). Theoretical element content (%) C 63 H 43 N3O: C, 88.19; H, 5.05; N, 4.90. Measured element content (%): C, 88.21; H, 5.08; N, 4.48.

[0216] Synthesis Example 16: Preparation of Compound 566:

[0217]

[0218] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-566, b-5 was replaced by an equal mole of b-566, and c-5 was replaced by an equal mole of c-566 to obtain compound 566 (16.61 g), HPLC purity ≧99.94%. Mass spectrum m / z: 768.2872 (theoretical value: 768.2889). Theoretical element content (%) C 55 H 36 N4O: C, 85.91; H, 4.72; N, 7.29. Measured element content (%): C, 85.89; H, 4.70; N, 7.31. Synthesis Example 17: Preparation of Compound 575:

[0219]

[0220] According to the same preparation method as in Synthesis Example 1, c-5 was replaced with an equal molar amount of c-575 to obtain compound 575 (18.83 g), HPLC purity ≧99.91%. Mass spectrum m / z: 847.3520 (theoretical value: 847.3501). Theoretical element content (%) C 62 H 37 D4N3O: C, 87.81; H, 5.35; N, 4.95. Measured element content (%): C, 87.78; H, 5.32; N, 4.99.

[0221] Synthesis Example 18: Preparation of Compound 577:

[0222]

[0223] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal molar amount of a-475, b-5 was replaced by an equal molar amount of b-577, and c-5 was replaced by an equal molar amount of c-150 to obtain compound 577 (18.48 g), HPLC purity ≧99.92%. Mass spectrum m / z: 843.3265 (theoretical value: 843.3250). Theoretical element content (%) C 62 H 41 N3O: C, 88.23; H, 4.90; N, 4.98. Measured element content (%): C, 88.19; H, 4.88; N, 4.95. Synthesis Example 19: Preparation of Compound 578:

[0224]

[0225] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal molar amount of a-545, b-5 was replaced by an equal molar amount of b-578, and c-5 was replaced by an equal molar amount of c-150 to obtain compound 578 (20.37 g), HPLC purity ≧99.94%. Mass spectrum m / z: 955.4519 (theoretical value: 955.4502). Theoretical element content (%) C 70 H 57 N3O: C, 87.92; H, 6.01; N, 4.39. Measured element content (%): C, 87.89; H, 6.04; N, 4.41. Synthesis Example 20: Preparation of Compound 580:

[0226]

[0227] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal molar amount of a-545, b-5 was replaced by an equal molar amount of b-580, and c-5 was replaced by an equal molar amount of c-150 to obtain compound 580 (18.23 g), HPLC purity ≧99.96%. Mass spectrum m / z: 867.3239 (theoretical value: 867.3250). Theoretical element content (%) C 64 H 41 N3O: C, 88.56; H, 4.76; N, 4.84. Measured element content (%): C, 88.59; H, 4.73; N, 4.80. Synthesis Example 21: Preparation of Compound 588:

[0228]

[0229] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-588, and c-5 was replaced by an equal mole of c-150 to obtain compound 588 (19.20 g), HPLC purity ≧99.95%. Mass spectrum m / z: 841.3080 (theoretical value: 841.3093). Theoretical element content (%) C 62 H 39 N3O: C, 88.44; H, 4.67; N, 4.99. Measured element content (%): C, 88.39; H, 4.66; N, 4.96.

[0230] Synthesis Example 22: Preparation of Compound 604:

[0231]

[0232] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal molar amount of a-475, b-5 was replaced by an equal molar amount of b-604, and c-5 was replaced by an equal molar amount of c-150 to obtain compound 604 (18.97 g), HPLC purity ≧99.92%. Mass spectrum m / z: 877.4046 (theoretical value: 877.4032). Theoretical element content (%) C 64 H 51 N3O: C, 87.54; H, 5.85; N, 4.79. Measured element content (%): C, 87.52; H, 5.84; N, 4.81. Synthesis Example 23: Preparation of Compound 613:

[0233]

[0234] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-613, b-5 was replaced by an equal mole of b-613, and c-5 was replaced by an equal mole of c-150 to obtain compound 613 (16.19 g), HPLC purity ≧99.93%. Mass spectrum m / z: 781.3082 (theoretical value: 781.3093). Theoretical element content (%) C 57 H 39 N3O: C, 87.55; H, 5.03; N, 5.37. Measured element content (%): C, 87.52; H, 5.00; N, 5.40. Synthesis Example 24: Preparation of Compound 627:

[0235]

[0236] According to the same preparation method as in Synthesis Example 1, c-5 was replaced with an equal molar amount of c-627 to obtain compound 627 (18.99 g), HPLC purity ≧99.96%. Mass spectrum m / z: 843.3268 (theoretical value: 843.3250). Theoretical element content (%) C 62 H 41 N3O: C, 88.23; H, 4.90; N, 4.98. Measured element content (%): C, 88.25; H, 4.88; N, 4.96.

[0237] Synthesis Example 25: Preparation of Compound 632:

[0238]

[0239] According to the same preparation method as in Synthesis Example 1, c-5 was replaced with an equal molar amount of c-632 to obtain compound 632 (20.13 g), HPLC purity ≧99.92%. Mass spectrum m / z: 859.3034 (theoretical value: 859.3021). Theoretical element content (%) C 62 H 41 N3S: C, 86.58; H, 4.81; N, 4.89. Measured element content (%): C, 86.60; H, 4.79; N, 4.92.

[0240] Synthesis Example 26: Preparation of Compound 642:

[0241]

[0242] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-642, and c-5 was replaced by an equal mole of c-632 to obtain compound 642 (19.67 g), HPLC purity ≧99.95%. Mass spectrum m / z: 873.3163 (theoretical value: 873.3178). Theoretical element content (%) C 63 H 43 N3S: C, 86.57; H, 4.96; N, 4.81. Measured element content (%): C, 86.60; H, 4.92; N, 4.79.

[0243] Synthesis Example 27: Preparation of Compound 709:

[0244]

[0245] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-709, and c-5 was replaced by an equal mole of c-632 to obtain compound 709 (16.93 g), HPLC purity ≧99.93%. Mass spectrum m / z: 783.2725 (theoretical value: 783.2708). Theoretical element content (%) C 56 H 37 N3S: C, 85.79; H, 4.76; N, 5.36. Measured element content (%): C, 85.83; H, 4.79; N, 5.33.

[0246] Synthesis Example 28: Preparation of Compound 756:

[0247]

[0248] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-756, and c-5 was replaced by an equal mole of c-632 to obtain compound 756 (17.89 g), HPLC purity ≧99.91%. Mass spectrum m / z: 863.3289 (theoretical value: 863.3272). Theoretical element content (%) C 62 H 37 D4N3S: C, 86.18; H, 5.25; N, 4.86. Measured element content (%): C, 86.20; H, 5.23; N, 4.89.

[0249] Synthesis Example 29: Preparation of Compound 772:

[0250]

[0251] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-475, and c-5 was replaced by an equal mole of c-772 to obtain compound 772 (16.01 g), HPLC purity ≧99.95%. Mass spectrum m / z: 784.2651 (theoretical value: 784.2661). Theoretical element content (%) C 55 H 36 N4S: C, 84.16; H, 4.62; N, 7.14. Measured element content (%): C, 84.19; H, 4.59; N, 7.16.

[0252] Synthesis Example 30: Preparation of Compound 800:

[0253]

[0254] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-150, and c-5 was replaced by an equal mole of c-800 to obtain compound 800 (16.57 g), HPLC purity ≧99.92%. Mass spectrum m / z: 735.2726 (theoretical value: 735.2708). Theoretical element content (%) C 52 H 37 N3S: C, 84.87; H, 5.07; N, 5.71. Measured element content (%): C, 84.90; H, 5.11; N, 5.69.

[0255] Synthesis Example 31: Preparation of Compound 835:

[0256]

[0257] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-835, b-5 was replaced by an equal mole of b-835, and c-5 was replaced by an equal mole of c-835 to obtain compound 835 (16.19 g), HPLC purity ≧99.94%. Mass spectrum m / z: 759.2719 (theoretical value: 759.2708). Theoretical element content (%) C 54 H 37 N3S: C, 85.34; H, 4.91; N, 5.53. Measured element content (%): C, 85.30; H, 4.94; N, 5.55. Synthesis Example 32: Preparation of Compound 882:

[0258]

[0259] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-150, and c-5 was replaced by an equal mole of c-882 to obtain compound 882 (17.05 g), HPLC purity ≧99.93%. Mass spectrum m / z: 811.3012 (theoretical value: 811.3021). Theoretical element content (%) C 58 H 41 N3S: C, 85.79; H, 5.09; N, 5.17. Measured element content (%): C, 85.81; H, 5.06; N, 5.20.

[0260] Synthesis Example 33: Preparation of Compound 910:

[0261]

[0262] According to the same preparation method as in Synthesis Example 1, b-5 was replaced by an equal mole of b-150, and c-5 was replaced by an equal mole of c-910 to obtain compound 910 (16.42 g), HPLC purity ≧99.91%. Mass spectrum m / z: 759.2721 (theoretical value: 759.2708). Theoretical element content (%) C 54 H 37 N3S: C, 85.34; H, 4.91; N, 5.53. Measured element content (%): C, 85.30; H, 4.88; N, 5.56.

[0263] Synthesis Example 34: Preparation of Compound 955:

[0264]

[0265] According to the same preparation method as in Synthesis Example 1, a-5 was replaced by an equal mole of a-955, b-5 was replaced by an equal mole of b-955, and c-5 was replaced by an equal mole of c-955 to obtain compound 955 (18.03 g), HPLC purity ≧99.96%. Mass spectrum m / z: 811.3002 (theoretical value: 811.3021). Theoretical element content (%) C 58 H 41 N3S: C, 85.79; H, 5.09; N, 5.17. Measured element content (%): C, 85.81; H, 5.05; N, 5.20.

[0266] [Device Example 1]

[0267] First, the ITO substrate was ultrasonically cleaned in distilled water for 3 times, each time for 15 minutes. After the distilled water cleaning, isopropanol, acetone, methanol and other solvents were used for ultrasonic cleaning in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0268] The vacuum evaporation method was used to sequentially evaporate the hole injection layer HI (60 nm); the hole transport layer compound 5 (80 nm); the light-emitting layer RH:RD=98:2 (mass ratio, 40 nm); the electron transport layer ET-1:Liq=1:1 (mass ratio, 30 nm); the electron injection layer LiF (0.8 nm); and the cathode Al (120 nm) on the cleaned ITO substrate to prepare an organic electroluminescent device.

[0269]

[0270] [Device Example 2-34]

[0271] The compound 66, compound 81, compound 150, compound 227, compound 268, compound 330, compound 350, compound 368, compound 420, compound 475, compound 531, compound 545, compound 547, compound 556, compound 566, compound 575, compound 577, compound 578, compound 580, compound 588, compound 604, compound 613, compound 627, compound 632, compound 642, compound 709, compound 756, compound 772, compound 800, compound 835, compound 882, compound 910 or compound 955 of the present invention are used to replace compound 5 in device example 1 as a hole transport layer material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 1.

[0272] [Comparative Device Examples 1-2]

[0273] An organic electroluminescent device was prepared by the same preparation method as in Device Example 1 except that Comparative Compound 1 or Comparative Compound 2 was used to replace Compound 5 in Device Example 1 as the hole transport layer material.

[0274] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the luminous efficiency of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is atmospheric environment and the temperature is room temperature.

[0275] The test results of the luminescent characteristics of the organic electroluminescent devices obtained in device embodiments 1-34 of the present invention and comparative embodiments 1-2 are shown in Table 1 below.

[0276]

[0277]

[0278] [Device Example 35]

[0279] First, the ITO substrate was ultrasonically cleaned in distilled water for 3 times, each time for 15 minutes. After the distilled water cleaning, isopropanol, acetone, methanol and other solvents were used for ultrasonic cleaning in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0280] The vacuum evaporation method was used to sequentially evaporate the hole injection layer HI (60 nm); the first hole transport layer HT (20 nm); the second hole transport layer compound 5 (60 nm); the light-emitting layer BH:BD=96:4 (mass ratio, 40 nm); the electron transport layer ET-2:Liq=1:1 (mass ratio, 35 nm); the electron injection layer LiF (1.0 nm); and the cathode Al (110 nm) on the cleaned ITO substrate to prepare an organic electroluminescent device.

[0281]

[0282] [Device Examples 36-68]

[0283] The compound 66, compound 81, compound 150, compound 227, compound 268, compound 330, compound 350, compound 368, compound 420, compound 475, compound 531, compound 545, compound 547, compound 556, compound 566, compound 575, compound 577, compound 578, compound 580, compound 588, compound 604, compound 613, compound 627, compound 632, compound 642, compound 709, compound 756, compound 772, compound 800, compound 835, compound 882, compound 910 or compound 955 of the present invention are used to replace compound 5 in device example 35 as the second hole transport layer material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 35.

[0284] [Comparative Device Examples 3-4]

[0285] An organic electroluminescent device was prepared by the same preparation method as that of Device Example 35, except that Comparative Compound 1 or Comparative Compound 2 was used to replace Compound 5 in Device Example 35 as the second hole transport layer material.

[0286] The test results of the luminescent characteristics of the organic electroluminescent devices obtained in device embodiments 35-68 of the present invention and comparative embodiments 3-4 are shown in Table 2 below.

[0287]

[0288] According to the data in Table 1 and Table 2, the triarylamine derivatives shown in Formula I of the present invention are applied to organic electroluminescent devices. Since the triarylamine derivatives have good hole transport ability and strong electron donating ability, they can balance the transport of carriers and increase the recombination probability of excitons in the light-emitting layer. As hole transport layer materials and second hole transport layer materials, the luminous efficiency and service life of the device are effectively improved.

[0289] [Device Example 69]

[0290] First, the ITO substrate was ultrasonically cleaned in distilled water for 3 times, each time for 15 minutes. After the distilled water cleaning, isopropanol, acetone, methanol and other solvents were used for ultrasonic cleaning in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0291] The vacuum evaporation method is used to sequentially evaporate the hole injection layer HI (60nm); the hole transport layer HT-1 (80nm); the light-emitting layer compound 5:GH:GD=49:49:2 (mass ratio, 40nm); the electron transport layer ET-3:Liq=1:1 (mass ratio, 35nm); the electron injection layer LiF (0.9nm); and the cathode Al (120nm) on the cleaned ITO substrate to prepare an organic electroluminescent device.

[0292]

[0293] [Device Examples 70-102]

[0294] The compound 163, compound 1730, compound 180, compound 198, compound 210, compound 233, compound 241, compound 266, compound 337, compound 350, compound 456, compound 460, compound 465, compound 468, compound 535, compound 566, compound 620, compound 650, compound 677, compound 681, compound 688, compound 710, compound 784 or compound 864 of the present invention are used to replace compound 92 in device example 69 as the first main material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 69.

[0295] [Comparative Device Examples 5-7]

[0296] An organic electroluminescent device is prepared by the same preparation method as Device Example 69, except that Comparative Compound 3, Comparative Compound 4 or Comparative Compound 5 is used to replace Compound 5 in Device Example 69 as the first host material.

[0297] The test results of the luminescent characteristics of the organic electroluminescent devices obtained in device embodiments 69-102 of the present invention and comparative embodiments 5-7 are shown in Table 3 below.

[0298]

[0299]

[0300] According to the data results in Table 3, it can be seen that when the triarylamine derivatives of the present invention are used as the first host material of an organic electroluminescent device, the luminous efficiency and service life of the device can be significantly improved. This is because the triarylamine derivatives of the present invention have a higher triplet energy level, which can reduce the energy barrier for hole injection and transmission, improve the hole transmission capacity, and increase the recombination probability of carriers.

[0301] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A triarylamine derivative, characterized in that: The triarylamine derivative has a structure as shown in Formula I, In formula I, Ar1 is selected from any one of the groups shown in formula II-1 and formula II-2; The Ar2 is selected from the group shown in formula III; The Y is selected from O, S, N (R c ) The t and v are the same or different from each other and are selected from CH or N atoms. When t and v are bonded to other groups, the t and v are selected from C atoms; The R a , R b The same as or different from each other, and any one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; The R c Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and aliphatic ring of C3-C30, substituted or unsubstituted C2-C30 heteroaryl; The R1, R2, and R3 are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring; The a is selected from 0, 1, 2, 3 or 4, the b is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the c is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 can be connected to form a substituted or unsubstituted ring; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 can be connected to form a substituted or unsubstituted ring; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 can be connected to form a substituted or unsubstituted ring; The L is selected from any one of the following groups and combinations thereof; The x are the same or different from each other and are selected from CH or N atoms. When x is bonded to other groups, the x is selected from C atoms; The t1 is selected from any one of O, S, and N(R6); Said t2 is selected from CH or N atoms; The ring A is selected from substituted or unsubstituted C3-C7 aliphatic rings; The m is selected from 1, 2 or 3; The R4 and R5 are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring; The R6 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 C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroaryl; 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, 1, 2, 3, 4, 5 or 6, when there are two or more R4, the two or more R4 are the same or different from each other, or two adjacent R4 can be connected to each other to form a substituted or unsubstituted ring; when there are two or more R5, the two or more R5 are the same or different from each other; The R x , R y are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring, or R x , R y They may be bonded to each other to form a substituted or unsubstituted ring; The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring condensed ring group, a substituted or unsubstituted C2-C30 heteroarylene group and a combination thereof; The L2 is selected from any one of the following groups and combinations thereof, which are substituted or unsubstituted by a single bond or one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: phenylene, biphenylene, terphenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, quinazolinylene, quinoxalylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, benzofuranylene, benzothiophenylene, indolylene, benzocyclopentylene, benzocyclohexylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, methylenefluorenylene, phenylfluorenylene, and spirofluorenylene.

2. A triarylamine derivative according to claim 1, characterized in that: The Ar1 is selected from any one of the following groups; The R2 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl or benzothiophenyl; wherein a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, a2 is selected from 0, 1, 2, 3, 4 or 5, a3 is selected from 0, 1, 2, 3 or 4, a4 ​​is selected from 0, 1, 2 or 3, a5 is selected from 0, 1, 2, 3, 4, 5 or 6, a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

3. A triarylamine derivative according to claim 1, characterized in that: The Ar2 is selected from any one of the following groups; The Y is selected from O, S, NR c Any of the following: The R c Any one of the following groups selected from hydrogen, deuterium, or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, benzocyclopentyl, benzocyclohexyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The R3 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, benzocyclopentanyl, benzocyclohexanyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The b1 is selected from 0, 1, 2 or 3, the b2 is selected from 0 or 1, the b3 is selected from 0, 1 or 2, the b4 is selected from 0, 1, 2, 3, 4 or 5, the b5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the b6 is selected from 0, 1, 2, 3 or 4.

4. A triarylamine derivative according to claim 1, characterized in that: The L is selected from any one of the following groups and combinations thereof; The R4 and R5 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane; The c1 is selected from 0, 1, 2, 3 or 4, the c2 is selected from 0, 1, 2 or 3, the c3 is selected from 0, 1 or 2, the c4 is selected from 0, 1, 2, 3, 4, 5 or 6, the c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the c7 is selected from 0 or 1.

5. A triarylamine derivative according to claim 1, characterized in that: The L1 is selected from any one of the following groups and combinations thereof, which are substituted or unsubstituted by a single bond or one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, quinazolinylene, quinoxalylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, benzofuranylene, benzothiophenylene, indolylene, benzocyclopentylene, benzocyclohexylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, methylenefluorenylene, phenylfluorenylene, and spirofluorenylene.

6. A triarylamine derivative according to claim 1, characterized in that: The triarylamine derivative is selected from any one of the structures shown below; 7. 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 any one of the anode and the cathode, characterized in that: The organic layer comprises any one or more of the triarylamine derivatives described in any one of claims 1 to 6.

8. An organic electroluminescent device according to claim 7, wherein the organic layer is located between the anode and the cathode, the organic layer comprises a hole transport region, a light emitting layer, and an electron transport region, the hole transport region is located between the anode and the light emitting layer, and characterized in that: The hole transport region comprises any one or more of the triarylamine derivatives described in any one of claims 1 to 6.

9. An organic electroluminescent device according to claim 7, wherein the organic layer is located between the anode and the cathode, the organic layer comprises two or more light-emitting parts and a charge generation layer, the first light-emitting part is located between the anode and the cathode, the second light-emitting part is located between the first light-emitting part and the cathode, and the charge generation layer is located between the first light-emitting part and the second light-emitting part, characterized in that: The charge generating layer comprises any one or more of the triarylamine derivatives described in any one of claims 1 to 6.

10. An organic electroluminescent device according to claim 7, wherein the organic layer is located between the anode and the cathode, the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, the light-emitting layer is located between the hole transport region and the electron transport region, and characterized in that: The light-emitting layer comprises any one or more of the triarylamine derivatives described in any one of claims 1 to 6.

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