A triarylamine derivative and an organic electroluminescent device thereof

Abstract

The present invention provides a triarylamine derivative and an organic electroluminescent device thereof, specifically relating to the field of organic electroluminescence technology. To address the low performance of prior art organic electroluminescent devices, the present invention provides a triarylamine derivative and an organic electroluminescent device thereof. The triarylamine derivative provided by the present invention has a high glass transition temperature (Tg), good thermal stability, and uniform and stable film-forming properties. Its application as a cover layer material in an organic electroluminescent device can increase the efficiency of light extraction from the device, thereby improving the luminous efficiency and extending the service life of the device.

Description

Technical Field

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

[0002] With the unprecedented development of science and technology and society, computer technology and Internet technology are also developing rapidly. Human society is gradually entering a new information age. As a communication medium between people and information, people have higher and higher requirements for display technology. Organic Light-Emitting Diode (OLED) is a new flat panel display technology with great prospects that has developed rapidly in recent decades. It is widely used in many fields such as display and lighting. The reason why OLED has such a wide range of applications is mainly due to its advantages such as high efficiency, high brightness, low driving voltage, good flexibility, wide viewing angle, fast response speed, high resolution, and a wide range of material selection. Based on these advantages, OLED has become a research focus of related industries at home and abroad.

[0003] Electroluminescence refers to the physical phenomenon of organic photoelectric materials emitting light under the influence of an electric current or electric field, directly converting electrical energy into light. Organic electroluminescent devices can be categorized by structure as single-layer, double-layer, or multi-layer devices. Multi-layer devices consist of an anode, 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, and an electron injection layer. The multi-layer structure fully utilizes the functions of each organic layer, balancing the transport of charge carriers and thereby improving the overall performance of the device.

[0004] However, there are still many technical problems in the development of organic electroluminescent devices, especially how to improve the luminous efficiency and extend the service life. Due to the huge gap between the external quantum efficiency and the internal quantum efficiency of OLED, the device has a light extraction efficiency of only about 20%, which seriously affects the development of OLED. Nearly 80% of the light cannot be emitted and is confined inside the device to dissipate as heat. Excessive heat accumulation will affect the life of the material and destroy the stable transmission of carriers. In severe cases, water and oxygen in the air will enter the device, causing the device to experience a sharp drop in efficiency. Therefore, how to improve the light extraction efficiency of the device is of far-reaching significance to the development of OLED. In order to solve this problem, people have proposed adding a covering layer to the electrode. However, the development of organic electroluminescent materials is not perfect at this stage, and there is little research on covering layer materials. Therefore, most of the existing covering layer materials have poor performance and cannot meet current needs.

[0005] Therefore, it is an urgent problem to design a covering material with a high glass transition temperature, thermal stability and good film-forming properties to effectively couple out the light trapped in the device, enhance the light extraction efficiency, and thus improve the luminous efficiency of the device and extend the service life of the device. Summary of the Invention

[0006] In order to obtain an organic electroluminescent device with high luminous efficiency and long service life, the present invention provides a triarylamine derivative and an organic electroluminescent device thereof.

[0007] The present invention provides a triarylamine derivative having a structure as shown in Formula I.

[0008]

[0009] In formula I, Y is selected from any one of O, S, C(R)2, and N(R);

[0010] The R groups are the same as or different from each other and are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, or R groups may be directly bonded to L0;

[0011] The z are the same as or different from each other and are selected from CH or N atoms. When z is bonded to other groups, the z is selected from C atoms;

[0012] The R z are the same as or different from each other and are selected from F, CF3, {Si(R1)3};

[0013] The R1s are the same or different and are selected from substituted or unsubstituted C1-C12 alkyl groups;

[0014] The n is selected from 1, 2, 3, 4 or 5, when there are two or more R z When two or more R z The same or different from each other, when R z When all are selected from F, n is selected from 5;

[0015] The Ar2 is selected from any one of the following groups:

[0016]

[0017] The x are the same as 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;

[0018] The t1 is selected from any one of O, S, N(R4), and C(R5)2, and the t2 is selected from any one of CH and N atoms;

[0019] The R4 and R5 are the same as or different from each other and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or R4 and R5 can be directly bonded to L2;

[0020] The Rx and Ry are the same or different and are selected from any one of hydrogen, deuterium, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or Rx and Ry may be connected to each other to form a substituted or unsubstituted ring, or Rx and Ry may be directly bonded to L2;

[0021] R2 and R3 are the same as or different from each other and are selected from any one of hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0022] wherein m1 is selected from 0, 1, 2, 3, 4, or 5; m2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; m4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; m5 is selected from 0, 1, or 2; m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and m7 is selected from 0, 1, 2, 3, or 4. When two or more R2s are present, the two or more R2s may be the same or different from each other, or two adjacent R2s may be connected to form a substituted or unsubstituted ring.

[0023] Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0024] The L0 is selected from one or more R c Substituted or unsubstituted: any one of a C6-C30 arylene group, a C2-C30 heteroarylene group, and a divalent fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0025] The R care the same as or different from each other and are selected from any one of trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0026] The L1 and L2 are the same or different and are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a divalent substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused ring, and any combination thereof;

[0027] The R a 、R b are the same as or different from each other and are selected from any one of hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a substituted or unsubstituted fused ring of a C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0028] The n1 is selected from 0, 1 or 2, when there are two or more R a When two or more R a the same as or different from one another;

[0029] The n2 is selected from 0, 1, 2, 3 or 4, when there are two or more R b When two or more R b Same or different from each other, or two adjacent R b They can be connected to each other to form substituted or unsubstituted aromatic rings or heteroaromatic rings.

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

[0031] Beneficial effects: The triarylamine derivatives represented by formula I provided by the present invention are used as covering layer materials in organic electroluminescent devices, which can significantly improve the luminous efficiency of the device and extend the service life. This is because the triarylamine derivatives represented by formula I of the present invention have a high glass transition temperature (Tg), high thermal stability, are not easy to decompose and crystallize at high temperatures, have good film-forming properties, reduce the generation of Joule heat inside the device, and thus improve the performance of the device. DETAILED DESCRIPTION

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

[0033] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes the atom at 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 attached to any one of the corresponding optional positions of the ring. For example, Can be represented Can be represented Can be represented 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 any of the corresponding optional sites of the ring. For example, Can represent Can be represented 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. It can 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 can be substituted or unsubstituted. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, and the like.

[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 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 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 "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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, 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. 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. 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. Preferably, the "substituted or unsubstituted C1-C25 alkylsilyl" refers to a silyl group substituted by a substituted or unsubstituted C1-C25 alkyl group, preferably substituted by three alkyl groups, and examples thereof may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, etc., but are not limited thereto.

[0041] The cycloalkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms. The cycloalkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms. The cycloalkyl group may be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl.

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

[0043] The heteroaryl group of the present invention is a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, wherein the heteroatom includes but is not limited to O, S, N, Si or P atoms, and preferably has 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The attachment point of the heteroaryl group can be located on a ring-forming carbon atom or a ring-forming heteroatom, and the heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed ring heteroaryl group. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc.; the fused ring heteroaryl groups include, but are not limited to, 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, etc., but is not limited thereto.

[0044] The aliphatic ring described herein 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 even more preferably 3 to 7 carbon atoms. It can form a monocyclic hydrocarbon or a polycyclic hydrocarbon and can be fully unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, and cycloheptene. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in a 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; and several rings can be connected to form a cage-like structure.

[0045] The fused ring of an aromatic ring and an aliphatic ring described in 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. 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 an aromatic ring and an 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 group, as a monocyclic arylene group, it can be a phenylene group, etc., but it is not limited thereto. 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 thereto. 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, fluoren ... 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, even more 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, furylene, pyranylene, oxazolylene, thiazolylene, imidazolylene, benzoxazolylene, benzothiazolylene, benzimidazolylene, carbazolylene, benzocarbazolylene, acridinylene, xanthenylene, thioanthenylene, phenazinylene, phenothiazinylene, phenoxazinylene, indolylene, quinolylene, isoquinolylene, benzothienylene, benzofuranylene, dibenzofuranylene, dibenzothienylene, quinoxalinylene, quinazolinylene, naphthyridinylene, purinylene, o-phenanthrolineylene, and the like, but are not limited thereto.

[0048] The divalent fused aromatic and aliphatic ring groups described herein are those with two linking sites, i.e., divalent groups. The description of the fused aromatic and aliphatic ring groups described above applies to these groups, except that they are divalent groups.

[0049] In the context of "substituted or unsubstituted" herein, "unsubstituted" means that no hydrogen atom on the group is 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 as 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 C1-C25 alkylsilyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, preferably Deuterium, cyano, halogen atoms, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C25 alkylsilyl, C6-C30 aryl, C2-C30 heteroaryl, specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, 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-1,2-diphenyl-1,2-diphenyl-1 The invention also includes oxazolyl, oxazolyl, thiazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, and the like, but is not limited thereto.

[0051] The term "linked to form a ring" as used herein refers to two groups being linked to each other via a chemical bond and optionally aromatized. For example:

[0052]

[0053] In this 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 thereto.

[0054] The present invention provides a triarylamine derivative having a structure as shown in Formula I.

[0055]

[0056] In formula I, Y is selected from any one of O, S, C(R)2, and N(R);

[0057] The R groups are the same as or different from each other and are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, or R groups may be directly bonded to L0;

[0058] The z are the same as or different from each other and are selected from CH or N atoms. When z is bonded to other groups, the z is selected from C atoms;

[0059] The R z are the same as or different from each other and are selected from F, CF3, {Si(R1)3};

[0060] The R1s are the same or different and are selected from substituted or unsubstituted C1-C12 alkyl groups;

[0061] The n is selected from 1, 2, 3, 4 or 5, when there are two or more R z When two or more R z The same or different from each other, when R z When all are selected from F, n is selected from 5;

[0062] The Ar2 is selected from any one of the following groups:

[0063]

[0064] The x are the same as 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;

[0065] The t1 is selected from any one of O, S, N(R4), and C(R5)2, and the t2 is selected from any one of CH and N atoms;

[0066] The R4 and R5 are the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or R4 and R5 may be directly bonded to L2;

[0067] The Rx and Ry are the same or different and are selected from any one of hydrogen, deuterium, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or Rx and Ry may be connected to each other to form a substituted or unsubstituted ring, or Rx and Ry may be directly bonded to L2;

[0068] R2 and R3 are the same as or different from each other and are selected from any one of hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0069] wherein m1 is selected from 0, 1, 2, 3, 4, or 5; m2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; m4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; m5 is selected from 0, 1, or 2; m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and m7 is selected from 0, 1, 2, 3, or 4. When two or more R2s are present, the two or more R2s may be the same or different from each other, or two adjacent R2s may be connected to form a substituted or unsubstituted ring.

[0070] The Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0071] The L0 is selected from one or more R c Substituted or unsubstituted: any one of a C6-C30 arylene group, a C2-C30 heteroarylene group, and a divalent fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0072] The R care the same as or different from each other and are selected from any one of trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0073] The L1 and L2 are the same or different and are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a divalent substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused ring, and any combination thereof;

[0074] The R a 、R b are the same as or different from each other and are selected from any one of hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a substituted or unsubstituted fused ring of a C6-C30 aromatic ring and a C3-C30 aliphatic ring;

[0075] The n1 is selected from 0, 1 or 2, when there are two or more R a When two or more R a the same as or different from one another;

[0076] The n2 is selected from 0, 1, 2, 3 or 4, when there are two or more R b When two or more R b Same or different from each other, or two adjacent R b They can be connected to each other to form substituted or unsubstituted aromatic rings or heteroaromatic rings.

[0077] Preferably, R1 are the same as or different from each other and are selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl.

[0078] More preferably, R1 are the same as or different from each other and are selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl.

[0079] Preferably, Si(R1)3 is selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, and tri-tert-butylsilyl.

[0080] Preferably, the Any one selected from the following groups;

[0081]

[0082]

[0083] Said Y is selected from any one of O, S, C(R)2, and N(R);

[0084] The R groups are the same as or different from each other and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentanyl, cyclohexanyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzothiophenyl, benzofuranyl, benzocyclopentanyl, or benzocyclohexanyl, or R may be directly bonded to L0;

[0085] The a1 is selected from 0, 1 or 2, the a2 is selected from 0, 1, 2, 3 or 4, the a3 is selected from 0, 1, 2 or 3, and the a4 is selected from 0 or 1.

[0086] Preferably, the Any one selected from the following groups;

[0087]

[0088]

[0089] Said Y is selected from any one of O, S, C(R)2, and N(R);

[0090] The R groups are the same as or different from each other and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentanyl, cyclohexanyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzothiophenyl, benzofuranyl, benzocyclopentanyl, or benzocyclohexanyl, or R may be directly bonded to L0;

[0091] The R a 、R bthe same as or different from each other, and any one of the following groups selected from hydrogen, deuterium, trifluoromethyl, fluorine, or substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzothienyl, benzofuranyl, benzocyclopentanyl, or benzocyclohexyl;

[0092] The b1 is selected from 0, 1 or 2, the b2 is selected from 0, 1, 2, 3 or 4, the b3 is selected from 0 or 1, the b4 is selected from 0, 1, 2, 3, 4, 5 or 6, the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the b6 is selected from 0, 1, 2, 3, 4 or 5, the b7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the b8 is selected from 0, 1, 2 or 3.

[0093] Preferably, the *-Ar1-(Rz)n is selected from any one of the groups shown below;

[0094]

[0095]

[0096] The R6 groups are the same as or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tri-tert-butylsilyl;

[0097] wherein c1 is selected from 0, 1, 2, 3 or 4, c2 is selected from 0, 1, 2 or 3, c3 is selected from 0, 1 or 2, c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, c6 is selected from 0, 1, 2, 3, 4 or 5, c7 is selected from 0 or 1, and c8 is selected from 0, 1, 2, 3, 4, 5 or 6. When two or more R6 are present, the two or more R6 are the same or different from each other, or two adjacent R6 can be connected to form a substituted or unsubstituted ring;

[0098] The q1 is selected from 1, 2, 3, 4 or 5, the q2 is selected from 1, 2, 3 or 4, the q3 is selected from 1, 2 or 3, the q4 is selected from 1, 2, 3, 4, 5, 6 or 7, the q5 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9, and the q6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0099] Preferably, the *-Ar1-(Rz)n is selected from any one of the groups shown below;

[0100]

[0101] The g1 is selected from 1, 2, 3 or 4, the g2 is selected from 1, 2, 3, 4, 5 or 6, and the g3 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the p1 is selected from 1, 2, 3, 4 or 5, the p2 is selected from 1, 2, 3 or 4, and the p3 is selected from 1, 2 or 3. Preferably, the Ar2 is selected from any one of the following groups:

[0102]

[0103]

[0104]

[0105] The t1 is selected from any one of O, S, N(R4), and C(R5)2, and the t2 is selected from any one of CH and N atoms;

[0106] R4 and R5 are the same as or different from each other and are selected from any one of the following groups, which are substituted or unsubstituted with one or more deuterium, trifluoromethyl, fluorine, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or naphthyridinyl, or R4 and R5 may be directly bonded to L2;

[0107] R2 and R3 are the same as or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, or tri-tert-butylsilyl;

[0108] The d1 is selected from 0, 1, 2, 3, 4 or 5, the d2 is selected from 0, 1, 2, 3 or 4, the d3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, the d6 is selected from 0, 1, 2 or 3, the d7 is selected from 0, 1 or 2, the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the d 10 Selected from 0, 1, 2, 3, 4, 5 or 6.

[0109] Preferably, L1 and L2 are the same or different from each other and are selected from a single bond or any one of the groups shown below;

[0110]

[0111]

[0112] The R7 are the same as or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl;

[0113] 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, 1, 2, 3, 4 or 5, the e7 is selected from 0 or 1, and the e8 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0114] Preferably, the L0 is selected from any one of the groups shown below;

[0115]

[0116] The v are the same as or different from each other and are selected from CH or N atoms. When v is bonded to other groups, the v is selected from C atoms;

[0117] The R cthe same as or different from each other, and selected from any one of the following groups which are substituted or unsubstituted by one or more trifluoromethyl, fluorine, or C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, or tri-tert-butylsilyl;

[0118] The f1 is selected from 0, 1, 2, 3 or 4, the f2 is selected from 0, 1 or 2, the f3 is selected from 0, 1, 2 or 3, the f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, the f7 is selected from 0 or 1, and the f8 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0119] Preferably, L0 is selected from any one of the following groups and combinations thereof;

[0120]

[0121]

[0122] Preferably, the triarylamine derivative is selected from any one of the following structures,

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] The above lists some specific structural forms of the triarylamine derivatives represented by Formula I of the present invention, but the present invention is not limited to these chemical structures listed. All those based on the structure shown in Chemical Formula I and having substituents as defined above are included.

[0149] The present invention provides a method for preparing the structure shown in Formula I, which is prepared by carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc., which are well known in the art, but the present invention is not limited thereto:

[0150] The structure shown in Formula 1 is prepared using the following synthetic route:

[0151] Preparation of raw material a:

[0152]

[0153] Preparation of raw material b:

[0154]

[0155] Preparation of raw material c:

[0156]

[0157] Preparation of compounds of formula I:

[0158]

[0159] Among them, X a 、X b The same as or different from each other, any one selected from Cl, Br, I; Ar1, Ar2, L0, L2, R a 、R b The limitations of , z, Y, n1, and n2 are the same as above.

[0160] The present invention also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic layer comprises at least one or more of the triarylamine derivatives.

[0161] 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.

[0162] Preferably, the hole transport region of the present invention comprises at least one of a hole injection layer and a hole transport layer.

[0163] Preferably, the hole transport layer of the present invention comprises a first hole transport layer and a second hole transport layer.

[0164] Preferably, the light-emitting layer of the present invention comprises a host material and a doping material.

[0165] Preferably, the electron transport region of the present invention comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0166] Preferably, the organic layer is located outside of any one of the anode and the cathode, and the organic layer comprises a covering layer, and the covering layer comprises at least one or more of the triarylamine derivatives described in the present invention.

[0167] Depending on the light emission direction, the organic electroluminescent device provided by the present invention can be any one of a top-emitting device, a bottom-emitting device, and a double-sided emitting device;

[0168] The present invention does not particularly limit the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The following is an introduction to the organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device:

[0169] The anode material of the present invention preferably uses a material with a high functional function to improve the 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 multi-layer 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.

[0170] The hole injection layer of the present invention preferably uses a material with good hole-accepting 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, and other materials, such as copper phthalocyanine (CuPc), phthalocyanine titanium oxide, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)biphenyl amine (MeO-TPD), diquinoxalino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), etc., but are not limited thereto.

[0171] The hole transport layer material of the present invention preferably has a high hole mobility and can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, diphenylenediamine derivatives, fluorene derivatives, stilbene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc. Examples of the hole transport layer material include the following materials, N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), N,N,N',N'-tetrakis(3-methylphenyl)-3,3'-dimethylbenzenediamine (HMTPD), etc., but are not limited thereto.

[0172] 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(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (α-AND), N,N'-di-(1-naphthyl)-N,N'-di Phenyl-[1,1':4',1":4",1"'-tetraphenyl]-4,4"'-diamino (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), etc. In addition to the above materials and their combinations, the main material of the light-emitting layer may also include other known materials suitable for the light-emitting layer, but is not limited thereto. The light-emitting layer doping materials of the present invention are divided into blue light-emitting materials, green light-emitting materials and red light-emitting materials. The light-emitting layer doping material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. From (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine))(DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)phenyl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)phenyl]biphenyl (DPAVBi), bis(2-hydroxyphenylpyridinium)beryllium (Bepp2), bis(4,6-difluorophenylpyridinium-C2,N)picolinyliridium (FIrpic), tris(2-phenylpyridinium) pyridine) iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)anilino]anthracene (TPA), 4-(dicyanomethylidene)-2-methyl-6-(4-dimethylaminophenyl)-4H-pyran (DCM), 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.

[0173] The doping ratio of the host material and the guest material in the light-emitting layer of the present invention is determined by the materials used. The amount of the dopant material used is preferably 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, further preferably 1 to 30% by mass, even more preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass.

[0174] 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 is not limited thereto.

[0175] The electron transport layer material of the present invention preferably has 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-hydroxyquinolinolate)aluminum(III) (Alq3), 8-hydroxyquinolinolate-lithium (Liq), bis(2-methyl-8-hydroxyquinolinolate)(4-phenylphenolate)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 is not limited thereto.

[0176] The electron injection layer material described in the present invention is preferably a material with a smaller potential barrier difference than 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, metallic aluminum, etc., but are not limited thereto.

[0177] 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. The cathode material 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.

[0178] The cover layer described herein is provided on the outside of either the anode or cathode, and is preferably made of a material that improves the light coupling efficiency within the device. The cover layer 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, and phthalocyanine derivatives, but is not limited thereto. The triarylamine derivatives described herein are preferred.

[0179] 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.

[0180] 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.

[0181] 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 light, etc.

[0182] The present invention is explained in more detail by the following examples, but it is not intended that the present invention be limited thereby. Based on 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 disclosed entire range without inventive effort.

[0183] Preparation and characterization of compounds

[0184] Description of raw materials, reagents and characterization equipment:

[0185] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples, and they can be commercially available products or prepared using methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0186] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0187] Elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5–10 mg;

[0188] Synthesis Example 1: Preparation of raw material a-186:

[0189]

[0190] Under nitrogen, d-186 (27.92 g, 90.00 mmol), e-186 (15.48 g, 90.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), K2CO3 (20.73 g, 150 mmol), and 450 mL of a 2:1:1 mixture of toluene, ethanol, and water were added to a reaction flask. The mixture was stirred and heated under reflux for 4 h. After the reaction, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The resulting solid was recrystallized from toluene and dried to afford the starting material a-186 (18.59 g, 75% yield); HPLC purity ≥99.72%. Mass spectrum: m / z: 275.0781 (theoretical value: 275.0769).

[0191] The raw materials are replaced accordingly, and the raw material a can be prepared according to the preparation method of the raw material a-186 in Synthesis Example 1. The raw materials are shown in the following table:

[0192]

[0193]

[0194] Synthesis Example 2: Preparation of raw material b-323:

[0195]

[0196] Under nitrogen, d-323 (33.32 g, 90.00 mmol), g-323 (17.23 g, 90.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), K2CO3 (20.73 g, 150 mmol), and 450 mL of a 2:1:1 mixture of toluene, ethanol, and water were added to a reaction flask. The mixture was stirred and heated under reflux for 3.5 h. After the reaction, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The resulting solid was recrystallized from a 10:1 mixture of toluene and ethanol and dried to give raw material b-323 (24.59 g, 77% yield) with an HPLC purity of ≥99.81%. Mass spectrum m / z: 354.0826 (theoretical value: 354.0811).

[0197] The raw materials are replaced accordingly, and the raw materials b / c can be prepared according to the preparation method of the raw material b-323 in Synthesis Example 2. The raw materials are shown in the following table:

[0198]

[0199]

[0200] Synthesis Example 3: Preparation of Compound 34

[0201]

[0202] Synthetic intermediate A-34:

[0203] Under nitrogen, a-34 (14.72 g, 60.00 mmol), b-34 (17.95 g, 60.00 mmol), Pd(OAc)2 (0.18 g, 0.80 mmol), P(t-Bu)3 (3.20 mL of a 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 a reaction flask. The mixture was stirred and heated under reflux for 5 h. After completion of the reaction, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The temperature was lowered for crystallization, and the resulting solid was filtered with suction. The resulting solid was recrystallized from toluene:methanol (12:1) to obtain intermediate A-34 (21.14 g, 76% yield) with HPLC purity ≥99.86%. Mass spectrum m / z: 463.2317 (theoretical value: 463.2300).

[0204] Synthesis of compound 34:

[0205] Under nitrogen, intermediate A-34 (13.91 g, 30.00 mmol), c-34 (10.36 g, 30.00 mmol), Pd2(dba)3 (0.41 g, 0.45 mmol), X-Phos (0.43 g, 0.90 mmol), NaOt-Bu (5.77 g, 60.00 mmol), and 150 ml of toluene were stirred and heated under reflux for 7 h. After completion of the reaction, the mixture was cooled to room temperature, added with distilled water, extracted with dichloromethane, and allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and the resulting solid was filtered with suction. The resulting solid was recrystallized from toluene to obtain compound 34 (16.16 g, 74% yield) with HPLC purity ≥99.97%. Mass spectrum: m / z: 727.3646 (theoretical value: 727.3634). Theoretical element content (%) C 53 H 49 NSi: C, 87.43; H, 6.78; N, 1.92. Measured element content (%): C, 87.41; H, 6.80; N, 1.89. Synthesis Example 4: Preparation of Compound 48

[0206]

[0207] Following the same preparation method as in Synthesis Example 3, compound 48 (15.37 g, 73%) was obtained by replacing a-34 with an equal molar amount of a-48, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 673.2667 (theoretical value: 673.2655). Theoretical element content (%): C 44 H 43 NSSi2: C, 78.40; H, 6.43; N, 2.08. Measured element content (%): C, 78.38; H, 6.42; N, 2.11.

[0208] Synthesis Example 5: Preparation of Compound 96

[0209]

[0210] Following the same preparation method as in Synthesis Example 3, compound 96 (15.56 g) was obtained by replacing a-34 with an equal molar amount of a-96, b-34 with an equal molar amount of b-96, and c-34 with an equal molar amount of c-96. HPLC purity ≥ 99.96%. Mass spectrum m / z: 710.0861 (theoretical value: 710.0875). Theoretical element content (%): C 37 H 16 F 10 N2S: C, 62.54; H, 2.27; N, 3.94. Measured element content (%): C, 62.56; H, 2.30; N, 3.92.

[0211] Synthesis Example 6: Preparation of Compound 123

[0212]

[0213] According to the same preparation method as in Synthesis Example 3, a-34 was replaced by an equal mole of a-123, b-34 was replaced by an equal mole of b-123, and c-34 was replaced by an equal mole of c-123 to obtain compound 123 (15.32 g, HPLC purity ≧99.95%. Mass spectrum m / z: 699.1984 (theoretical value: 699.1997). Theoretical element content (%) C 44 H 27 F6NO: C, 75.53; H, 3.89; N, 2.00. Measured element content (%): C, 75.56; H, 3.91; N, 2.01.

[0214] Synthesis Example 7: Preparation of Compound 138

[0215]

[0216] Following the same preparation method as in Synthesis Example 3, compound 138 (15.20 g) was obtained by replacing a-34 with an equal molar amount of a-138, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 657.1969 (theoretical value: 657.1980). Theoretical element content (%): C 43 H 35 NS2Si: C, 78.50; H, 5.36; N, 2.13. Measured element content (%): C, 78.47; H, 5.38; N, 2.15.

[0217] Synthesis Example 8: Preparation of Compound 186

[0218]

[0219] Following the same preparation method as in Synthesis Example 3, compound 186 (15.14 g) was obtained by replacing a-34 with an equal molar amount of a-186, b-34 with an equal molar amount of b-186, and c-34 with an equal molar amount of c-186. HPLC purity ≥ 99.96%. Mass spectrum m / z: 681.1971 (theoretical value: 681.1980). Theoretical element content (%): C 45 H 35 NS2Si: C, 79.25; H, 5.17; N, 2.05. Measured element content (%): C, 79.23; H, 5.20; N, 2.08.

[0220] Synthesis Example 9: Preparation of Compound 216

[0221]

[0222] Following the same preparation method as in Synthesis Example 3, compound 216 (14.08 g) was obtained by replacing a-34 with an equal molar amount of a-216, b-34 with an equal molar amount of b-216, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 625.2452 (theoretical value: 625.2437). Theoretical element content (%): C 43 H 35 NO2Si: C, 82.52; H, 5.64; N, 2.24. Measured element content (%): C, 82.49; H, 5.66; N, 2.26.

[0223] Synthesis Example 10: Preparation of Compound 237

[0224]

[0225] Following the same preparation method as in Synthesis Example 3, compound 237 (16.76 g) was obtained by replacing a-34 with an equal molar amount of a-237, b-34 with an equal molar amount of b-237, and c-34 with an equal molar amount of c-237. HPLC purity ≥ 99.94%. Mass spectrum m / z: 775.2915 (theoretical value: 775.2907). Theoretical element content (%): C 55 H 41 NO2Si: C, 85.13; H, 5.33; N, 1.80. Measured element content (%): C, 85.14; H, 5.34; N, 1.78.

[0226] Synthesis Example 11: Preparation of Compound 265

[0227]

[0228] Following the same preparation method as in Synthesis Example 3, compound 265 (15.00 g) was obtained by replacing a-34 with an equal molar amount of a-138, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-96. The HPLC purity was ≥99.97%. Mass spectrum: m / z: 675.1128 (theoretical value: 675.1114). Theoretical element content (%): C 40 H 22 F5NS2: C, 71.10; H, 3.28; N, 2.07. Measured element content (%): C, 71.06; H, 3.31; N, 2.11. Synthesis Example 12: Preparation of Compound 288

[0229]

[0230] Following the same preparation method as in Synthesis Example 3, a-34 was replaced with an equal molar amount of a-138, b-34 was replaced with an equal molar amount of b-48, and c-34 was replaced with an equal molar amount of c-288 to obtain compound 288 (15.84 g). HPLC purity was ≥99.94%. Mass spectrum m / z: 694.1345 (theoretical value: 694.1360). Theoretical element content (%): C 42 H 25 F3N2OS2: C, 72.61; H, 3.63; N, 4.03. Measured element content (%): C, 72.59; H, 3.65; N, 4.06.

[0231] Synthesis Example 13: Preparation of Compound 323

[0232]

[0233] Following the same preparation method as in Synthesis Example 3, compound 323 (18.81 g) was obtained by replacing a-34 with an equal molar amount of a-323, b-34 with an equal molar amount of b-323, and c-34 with an equal molar amount of c-96. HPLC purity ≥ 99.92%. Mass spectrum m / z: 895.2522 (theoretical value: 895.2510). Theoretical element content (%): C 60 H 34 F5NO2: C, 80.44; H, 3.83; N, 1.56. Measured element content (%): C, 80.41; H, 3.79; N, 1.58.

[0234] Synthesis Example 14: Preparation of Compound 340

[0235]

[0236] Following the same preparation method as in Synthesis Example 3, compound 340 (14.51 g) was obtained by replacing a-34 with an equal molar amount of a-138, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-123. HPLC purity ≥ 99.97%. Mass spectrum m / z: 653.1443 (theoretical value: 653.1459). Theoretical element content (%): C 41 H 26 F3NS2: C, 75.32; H, 4.01; N, 2.14. Measured element content (%): C, 75.29; H, 4.03; N, 2.17.

[0237] Synthesis Example 15: Preparation of Compound 412

[0238]

[0239] Following the same preparation method as in Synthesis Example 3, compound 412 (15.27 g) was obtained by replacing a-34 with an equal molar amount of a-216, b-34 with an equal molar amount of b-412, and c-34 with an equal molar amount of c-412. HPLC purity ≥ 99.91%. Mass spectrum m / z: 726.2716 (theoretical value: 726.2703). Theoretical element content (%): C 50 H 38 N2O2Si: C, 82.61; H, 5.27; N, 3.85. Measured element content (%): C, 82.59; H, 5.30; N, 3.83.

[0240] Synthesis Example 16: Preparation of Compound 413

[0241]

[0242] Following the same preparation method as in Synthesis Example 3, compound 413 (14.44 g) was obtained by replacing a-34 with an equal molar amount of a-216, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 641.2219 (theoretical value: 641.2209). Theoretical element content (%): C 43 H 35 NOSSi: C, 80.46; H, 5.50; N, 2.18. Measured element content (%): C, 80.50; H, 5.49; N, 2.21.

[0243] Synthesis Example 17: Preparation of Compound 452

[0244]

[0245] Following the same preparation method as in Synthesis Example 3, compound 452 (14.83 g) was obtained by replacing a-34 with an equal molar amount of a-452, b-34 with an equal molar amount of b-452, and c-34 with an equal molar amount of c-452. HPLC purity ≥ 99.94%. Mass spectrum m / z: 658.2872 (theoretical value: 658.2855). Theoretical element content (%): C 45 H 30 D7NSSi: C, 82.02; H, 6.73; N, 2.13. Measured element content (%): C, 82.05; H, 6.70; N, 2.09.

[0246] Synthesis Example 18: Preparation of Compound 476

[0247]

[0248] Following the same preparation method as in Synthesis Example 3, compound 476 (16.88 g) was obtained by replacing a-34 with an equal molar amount of a-476, b-34 with an equal molar amount of b-476, and c-34 with an equal molar amount of c-476. HPLC purity ≥ 99.93% was obtained. Mass spectrum m / z: 803.2438 (theoretical value: 803.2454). Theoretical element content (%): C 48 H 36 F7NOSi: C, 71.72; H, 4.51; N, 1.74. Measured element content (%): C, 71.69; H, 4.48; N, 1.76.

[0249] Synthesis Example 19: Preparation of Compound 482

[0250]

[0251] Following the same preparation method as in Synthesis Example 3, compound 482 (14.86 g) was obtained by replacing a-34 with an equal molar amount of a-482, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 651.2431 (theoretical value: 651.2416). Theoretical element content (%): C 45 H 37 NSSi: C, 82.91; H, 5.72; N, 2.15. Measured element content (%): C, 82.88; H, 5.69; N, 2.17.

[0252] Synthesis Example 20: Preparation of Compound 489

[0253]

[0254] Following the same preparation method as in Synthesis Example 3, compound 489 (16.62 g) was obtained by replacing a-34 with an equal molar amount of a-489, b-34 with an equal molar amount of b-489, and c-34 with an equal molar amount of b-489. HPLC purity ≥ 99.90%. Mass spectrum m / z: 779.2546 (theoretical value: 779.2532). Theoretical element content (%): C 50 H 45 NS2Si2: C, 76.97; H, 5.81; N, 1.80. Measured element content (%): C, 76.95; H, 5.79; N, 1.81.

[0255] Synthesis Example 21: Preparation of Compound 502

[0256]

[0257] Following the same preparation method as in Synthesis Example 3, compound 502 (15.51 g) was obtained by replacing a-34 with an equal molar amount of a-482, b-34 with an equal molar amount of b-216, and c-34 with an equal molar amount of c-502. HPLC purity ≥ 99.96%. Mass spectrum m / z: 707.3032 (theoretical value: 707.3040). Theoretical element content (%): C 48 H 45 NOSi2: C, 81.42; H, 6.41; N, 1.98. Measured element content (%): C, 81.45; H, 6.37; N, 1.97.

[0258] Synthesis Example 22: Preparation of Compound 512

[0259]

[0260] Following the same preparation method as in Synthesis Example 3, compound 512 (15.07 g) was obtained by replacing a-34 with an equal molar amount of a-482, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-96. HPLC purity ≥ 99.97%. Mass spectrum m / z: 669.1533 (theoretical value: 669.1550). Theoretical element content (%): C 42 H 24 F5NS: 75.33; H, 3.61; N, 2.09. Measured element content (%): 75.35; H, 3.59; N, 2.12. Synthesis Example 23: Preparation of Compound 522

[0261]

[0262] Following the same preparation method as in Synthesis Example 3, compound 522 (14.97 g) was obtained by replacing a-34 with an equal molar amount of a-522, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-522. HPLC purity ≥ 99.96%. Mass spectrum m / z: 647.2482 (theoretical value: 647.2498). Theoretical element content (%): C 42 H 41 NSSi2: C, 77.85; H, 6.38; N, 2.16. Measured element content (%): C, 77.81; H, 6.40; N, 2.20.

[0263] Synthesis Example 24: Preparation of Compound 544

[0264]

[0265] Following the same preparation method as in Synthesis Example 3, compound 544 (15.10 g) was obtained by replacing a-34 with an equal molar amount of a-544, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-544. HPLC purity ≥ 99.96%. Mass spectrum m / z: 689.1625 (theoretical value: 689.1612). Theoretical element content (%): C 42 H 25 F6NS: C, 73.14; H, 3.65; N, 2.03. Measured element content (%): C, 73.11; H, 3.68; N, 2.05. Synthesis Example 25: Preparation of Compound 556

[0266]

[0267] Following the same preparation method as in Synthesis Example 3, compound 556 (16.65 g) was obtained by replacing a-34 with an equal molar amount of a-556, b-34 with an equal molar amount of b-556, and c-34 with an equal molar amount of c-556. HPLC purity ≥ 99.94%. Mass spectrum m / z: 781.2578 (theoretical value: 781.2592). Theoretical element content (%): C 55 H 34 F3NO: C, 84.49; H, 4.38; N, 1.79. Measured element content (%): C, 84.51; H, 4.34; N, 1.81.

[0268] Synthesis Example 26: Preparation of Compound 562

[0269]

[0270] Following the same preparation method as in Synthesis Example 3, compound 562 (15.55 g) was obtained by replacing a-34 with an equal molar amount of a-562, b-34 with an equal molar amount of b-562, and c-34 with an equal molar amount of c-562. HPLC purity ≥ 99.92%. Mass spectrum m / z: 709.9622 (theoretical value: 709.9640). Theoretical element content (%): C 51 H 39 NOSi: C, 86.28; H, 5.54; N, 1.97. Measured element content (%): C, 86.30; H, 5.57; N, 1.96.

[0271] Synthesis Example 27: Preparation of Compound 564

[0272]

[0273] Following the same preparation method as in Synthesis Example 3, compound 564 (15.29 g) was obtained by replacing a-34 with an equal molar amount of a-564, b-34 with an equal molar amount of b-564, and c-34 with an equal molar amount of c-564. HPLC purity ≥ 99.95%. Mass spectrum m / z: 707.1535 (theoretical value: 707.1518). Theoretical element content (%): C 42 H 24 F7NS: C, 71.28; H, 3.42; N, 1.98. Measured element content (%): C, 71.30; H, 3.39; N, 1.96.

[0274] Synthesis Example 28: Preparation of Compound 574

[0275]

[0276] Following the same preparation method as in Synthesis Example 3, compound 574 (16.27 g) was obtained by replacing a-34 with an equal molar amount of a-574, b-34 with an equal molar amount of b-574, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.93%. Mass spectrum m / z: 752.2692 (theoretical value: 752.2681). Theoretical element content (%): C 52 H 40 N2SSi: C, 82.94; H, 5.35; N, 3.72. Measured element content (%): C, 82.98; H, 5.37; N, 3.69.

[0277] Synthesis Example 29: Preparation of Compound 580

[0278]

[0279] Following the same preparation method as in Synthesis Example 3, compound 580 (16.38 g) was obtained by replacing a-34 with an equal molar amount of a-580, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-96. HPLC purity ≥ 99.96%. Mass spectrum m / z: 747.1755 (theoretical value: 747.1768). Theoretical element content (%): C 46 H 26 F5N3S: C, 73.89; H, 3.50; N, 5.62. Measured element content (%): C, 73.92; H, 3.49; N, 5.64.

[0280] Synthesis Example 30: Preparation of Compound 582

[0281]

[0282] Following the same preparation method as in Synthesis Example 3, compound 582 (14.33 g) was obtained by replacing a-34 with an equal molar amount of a-582, b-34 with an equal molar amount of b-582, and c-34 with an equal molar amount of c-582. HPLC purity ≥ 99.95%. Mass spectrum m / z: 645.1287 (theoretical value: 645.1298). Theoretical element content (%): C 38 H 20 F5N3S: C, 70.69; H, 3.12; N, 6.51. Measured element content (%): C, 70.72; H, 3.09; N, 6.48.

[0283] Synthesis Example 31: Preparation of Compound 592

[0284]

[0285] Following the same preparation method as in Synthesis Example 3, compound 592 (14.28 g) was obtained by replacing a-34 with an equal molar amount of a-592, b-34 with an equal molar amount of b-592, and c-34 with an equal molar amount of c-123. HPLC purity ≥ 99.97%. Mass spectrum m / z: 634.1993 (theoretical value: 634.1980). Theoretical element content (%): C 40 H 25 F3N4O: C, 75.70; H, 3.97; N, 8.83. Measured element content (%): C, 75.69; H, 3.95; N, 8.85.

[0286] Synthesis Example 32: Preparation of Compound 602

[0287]

[0288] Following the same preparation method as in Synthesis Example 3, compound 602 (14.47 g) was obtained by replacing a-34 with an equal molar amount of a-602, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 642.2175 (theoretical value: 642.2161). Theoretical element content (%): C 42 H 34 N2OSSi: C, 78.47; H, 5.33; N, 4.36. Measured element content (%): C, 78.51; H, 5.35; N, 4.33.

[0289] Synthesis Example 33: Preparation of Compound 611

[0290]

[0291] Following the same preparation method as in Synthesis Example 3, compound 611 (13.29 g) was obtained by replacing a-34 with an equal molar amount of a-611, b-34 with an equal molar amount of b-48, and c-34 with an equal molar amount of c-186. HPLC purity ≥ 99.95%. Mass spectrum m / z: 582.1635 (theoretical value: 582.1620). Theoretical element content (%): C 36 H 30 N2S2Si: C, 74.19; H, 5.19; N, 4.81. Measured element content (%): C, 74.22; H, 5.17; N, 4.78.

[0292] Synthesis Example 34: Preparation of Compound 618

[0293]

[0294] Following the same preparation method as in Synthesis Example 3, compound 618 (14.10 g) was obtained by replacing a-34 with an equal molar amount of a-602, b-34 with an equal molar amount of b-216, and c-34 with an equal molar amount of c-48. HPLC purity ≥ 99.98%. Mass spectrum m / z: 626.2399 (theoretical value: 626.2390). Theoretical element content (%): C 42 H 34 N2O2Si: C, 80.48; H, 5.47; N, 4.47. Measured element content (%): C, 80.51; H, 5.44; N, 4.50.

[0295] Synthesis Example 35: Preparation of Compound 664

[0296]

[0297] Following the same preparation method as in Synthesis Example 3, compound 664 (16.39 g) was obtained by replacing a-34 with an equal molar amount of a-664, b-34 with an equal molar amount of b-216, and c-34 with an equal molar amount of c-664. HPLC purity ≥ 99.96%. Mass spectrum m / z: 718.2459 (theoretical value: 718.2474). Theoretical element content (%): C 48 H 38 N2OSSi: C, 80.19; H, 5.33; N, 3.90. Measured element content (%): C, 80.21; H, 5.35; N, 3.87.

[0298] Synthesis Example 36: Preparation of Compound 684

[0299]

[0300] Following the same preparation method as in Synthesis Example 3, compound 684 (16.19 g) was obtained by replacing a-34 with an equal molar amount of a-684, b-34 with an equal molar amount of b-684, and c-34 with an equal molar amount of c-684. HPLC purity ≥ 99.94%. Mass spectrum m / z: 781.1848 (theoretical value: 781.1833). Theoretical element content (%): C 49 H 30 F3N3S2: C, 75.27; H, 3.87; N, 5.37. Measured element content (%): C, 75.27; H, 3.87; N, 5.37.

[0301] Synthesis Example 37: Preparation of Compound 702

[0302]

[0303] Following the same preparation method as in Synthesis Example 3, compound 702 (15.99 g) was obtained by replacing a-34 with an equal molar amount of a-702, b-34 with an equal molar amount of b-702, and c-34 with an equal molar amount of c-702. HPLC purity ≥ 99.91%. Mass spectrum m / z: 739.3616 (theoretical value: 739.3606). Theoretical element content (%): C 51 H 45 D4NSSi: C, 82.76; H, 7.22; N, 1.89. Measured element content (%): C, 82.75; H, 7.20; N, 1.91.

[0304] Synthesis Example 38: Preparation of Compound 730

[0305]

[0306] Following the same preparation method as in Synthesis Example 3, compound 730 (13.23 g) was obtained by replacing a-34 with an equal molar amount of a-730, b-34 with an equal molar amount of b-730, and c-34 with an equal molar amount of c-730. HPLC purity ≥ 99.93%. Mass spectrum m / z: 612.1496 (theoretical value: 612.1483). Theoretical element content (%): C 38 H 23 F3N2OS: C, 74.50; H, 3.78; N, 4.57. Measured element content (%): C, 74.48; H, 3.81; N, 4.60.

[0307] Synthesis Example 39: Preparation of Compound 736

[0308]

[0309] Following the same preparation method as in Synthesis Example 3, compound 736 (16.44 g) was obtained by replacing a-34 with an equal molar amount of a-736, b-34 with an equal molar amount of b-736, and c-34 with an equal molar amount of c-736. HPLC purity ≥ 99.97%. Mass spectrum m / z: 750.1732 (theoretical value: 750.1718). Theoretical element content (%): C 44 H 23 F9N2: C, 70.40; H, 3.09; N, 3.73. Measured element content (%): C, 70.39; H, 3.11; N, 3.75.

[0310] Synthesis Example 40: Preparation of Compound 753

[0311]

[0312] Following the same preparation method as in Synthesis Example 3, compound 753 (15.18 g) was obtained by replacing a-34 with an equal molar amount of a-753, b-34 with an equal molar amount of b-753, and c-34 with an equal molar amount of c-753. HPLC purity ≥ 99.95%. Mass spectrum m / z: 683.2822 (theoretical value: 683.2834). Theoretical element content (%): C 45 H 40 F3NS: C, 79.03; H, 5.90; N, 2.05. Measured element content (%): C, 79.05; H, 5.87; N, 2.09.

[0313] Synthesis Example 41: Preparation of Compound 775

[0314]

[0315] Following the same preparation method as in Synthesis Example 3, compound 775 (17.30 g) was obtained by replacing a-34 with an equal molar amount of a-775, b-34 with an equal molar amount of b-775, and c-34 with an equal molar amount of c-123. HPLC purity ≥ 99.93%. Mass spectrum m / z: 789.2690 (theoretical value: 789.2677). Theoretical element content (%): C 54 H 38 F3NS: C, 82.10; H, 4.85; N, 1.77. Measured element content (%): C, 82.08; H, 4.83; N, 1.80.

[0316] Synthesis Example 42: Preparation of Compound 790

[0317]

[0318] Following the same preparation method as in Synthesis Example 3, compound 790 (12.56 g) was obtained by replacing a-34 with an equal molar amount of a-790, b-34 with an equal molar amount of b-790, and c-34 with an equal molar amount of c-790. HPLC purity ≥ 99.90%. Mass spectrum m / z: 606.2170 (theoretical value: 606.2154). Theoretical element content (%): C 36 H 20 D5F6NO: C, 71.28; H, 4.98; N, 2.31. Measured element content (%): C, 71.30; H, 4.95; N, 2.29.

[0319] [Device Example 1]

[0320] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water, each time for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in isopropyl alcohol, acetone, methanol and other solvents in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0321] By vacuum evaporation, HI-1 and P-1 (doping mass ratio of 97:3) were evaporated on the cleaned ITO / Ag / ITO substrate as a hole injection layer with a deposition thickness of 12 nm; HT-1 was evaporated on the hole injection layer as a hole transport layer with a deposition thickness of 80 nm; RH:RD = 98:2 (mass ratio) was evaporated on the hole transport layer as a light-emitting layer with a deposition thickness of 40 nm; ET-1 and Liq (doping mass ratio of 1:1) were evaporated on the light-emitting layer as an electron transport layer with a deposition thickness of 35 nm; LiF was evaporated on the electron transport layer as an electron injection layer with a deposition thickness of 0.8 nm; Mg:Ag = 1:9 (doping mass ratio of 1:1) was evaporated on the electron injection layer as a cathode with a deposition thickness of 13 nm, and then compound 34 was evaporated on the cathode as a covering layer with a deposition thickness of 80 nm, thereby preparing an organic electroluminescent device.

[0322]

[0323] [Device Example 2-40]

[0324] An organic electroluminescent device was prepared by the same preparation method as in Device Example 1, except that Compound 48, Compound 96, Compound 123, Compound 138, Compound 186, Compound 216, Compound 237, Compound 265, Compound 288, Compound 323, Compound 340, Compound 412, Compound 413, Compound 452, Compound 476, Compound 482, Compound 489, Compound 502, Compound 512, Compound 522, Compound 544, Compound 556, Compound 562, Compound 564, Compound 574, Compound 580, Compound 582, Compound 592, Compound 602, Compound 611, Compound 618, Compound 664, Compound 684, Compound 702, Compound 730, Compound 736, Compound 753, Compound 775 or Compound 790 of the present invention was used to replace Compound 34 in Device Example 1 as the covering layer material.

[0325] [Comparative Device Examples 1-5]

[0326] An organic electroluminescent device was prepared by the same preparation method as in Device Example 1, except that Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4 or Comparative Compound 5 was used to replace Compound 34 in Device Example 1 as the covering layer material.

[0327] A combined IVL test system, comprised of test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to measure the luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System. The test environment was atmospheric and room temperature.

[0328] The test results of the luminescence characteristics of the organic electroluminescent devices obtained in device embodiments 1 to 40 of the present invention and comparative embodiments 1 to 5 are shown in Table 1 below.

[0329]

[0330]

[0331] According to the data results in Table 1, it can be seen that the triarylamine derivative represented by formula I of the present invention is used as a cover layer material in an organic electroluminescent device, which can effectively improve the luminous efficiency of the device and extend the service life of the device.

[0332] 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, Any one selected from the following groups; Said Y is selected from O, S, C(R)2, N(R A ) The R groups are the same or different and are selected from any one of the following groups which are substituted or unsubstituted with one or more deuterium groups: methyl, ethyl, propyl, isopropyl, and tert-butyl; The R A The same as or different from each other, any one of the following groups which are substituted or unsubstituted by one or more deuterium groups: phenyl, biphenyl, naphthyl; The R a the same as or different from each other, and selected from hydrogen, deuterium, or any one of the following groups which are substituted or unsubstituted by one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl; The R b the same as or different from each other, and are selected from hydrogen, deuterium, or the following groups which are substituted or unsubstituted by one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl; b1 is selected from 0, 1 or 2, b2 is selected from 0, 1, 2, 3 or 4, b3 is selected from 0 or 1, b4 is selected from 0, 1, 2, 3, 4, 5 or 6, b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and b6 is selected from 0, 1, 2, 3, 4 or 5; The *-Ar1-(Rz)n is selected from any one of the groups shown below; wherein the R6 are the same or different and are selected from any one of hydrogen and deuterium, and the R z are identically selected from F, CF3, {Si(R1)3}; when Rz is selected from F, q1 is selected from 5, and c1 is selected from 0; when Rz is selected from CF3, {Si(R1)3}, q1 is selected from 1 or 2, and c1 is selected from 3 or 4; 6a are the same as or different from each other and are selected from any one of hydrogen, deuterium and fluorine, wherein the c 1a Selected from 0, 1, 2, 3 or 4, when R 6a When selected from fluorine, the c 1a Selected from 4; wherein the R6 are the same or different and are selected from any one of hydrogen, deuterium and fluorine. z are identically selected from F, CF3, {Si(R1)3}; when Rz is selected from F, q1 is selected from 4, c1 is selected from 0, R6 is selected from fluorine, and c2 is selected from 3; when Rz is selected from CF3, {Si(R1)3}, q1 is selected from 1, c1 is selected from 0, 1, 2, 3 or 4, c2 is selected from 0, 1, 2 or 3, and R6 is selected from any one of hydrogen and deuterium; wherein the R6 are the same or different and are selected from any one of hydrogen and deuterium, and the R z Selected from CF3, {Si(R1)3}, said q1 is selected from 1, said q2 is selected from 1, said q3 is selected from 1, said c1 is selected from 0, 1, 2, 3 or 4, said c2 is selected from 0, 1, 2 or 3, said c3 is selected from 0, 1 or 2, and said c7 is selected from 0 or 1; The R1 are the same or different and are selected from substituted or unsubstituted C1 to C6 alkyl groups; The Ar2 is selected from any one of the groups shown below; The t1 is selected from any one of O, S, N(R4), and C(R5)2, and the t2 is selected from any one of CH and N atoms; The R4 are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted by one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl; The R5 is selected from any one of the following groups which are substituted or unsubstituted with one or more deuterium groups: phenyl, biphenyl, naphthyl; The R 2a are the same as or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine or any one of the following groups which may be substituted or unsubstituted by one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, trimethylsilyl, triethylsilyl, triisopropylsilyl or tri-tert-butylsilyl; The R 2b are the same as or different from each other and are selected from hydrogen, deuterium, and fluorine; The R 2c are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted by one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, naphthyl; The R 2d are the same as or different from each other and are selected from hydrogen, deuterium, trifluoromethyl or any one of the following groups which may be substituted or unsubstituted by one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl or tri-tert-butylsilyl; The R2 are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted with one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, and phenyl; The R3 are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted with one or more deuterium groups: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, and naphthyl; The d1 is selected from 0, 1, 2, 3, 4 or 5, the d2 is selected from 0, 1, 2, 3 or 4, the d3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, the d6 is selected from 0, 1, 2 or 3, the d7 is selected from 0, 1 or 2, the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the d 10 Selected from 0, 1, 2, 3, 4, 5 or 6; for When R 2a When selected from fluorine, the d1 is selected from 5, the R 2b is selected from fluorine, said d2 is selected from 4; when R 2a When d1 is selected from 1 or 2, the R 2b Any one selected from hydrogen and deuterium; for When R 2d When d2 is selected from 1 and d3 is selected from 1, the group is selected from trifluoromethyl or any one of the following groups which are substituted or unsubstituted by one or more deuteriums: trimethylsilyl, triethylsilyl, triisopropylsilyl or tri-tert-butylsilyl; The L0 is selected from any one of the following groups; The L1 and L2 are the same or different from each other and are selected from a single bond or any one of the groups shown below; The R7 are the same as or different from each other and are selected from any one of hydrogen, deuterium, or the following groups which are substituted or unsubstituted with one or more deuterium groups: methyl; The e1 is selected from 0, 1, 2, 3 or 4, and the e2 is selected from 0, 1, 2 or 3.

2. A triarylamine derivative according to claim 1, characterized in that: described Any one selected from the following groups; The R a 、R b are the same as or different from each other and are selected from hydrogen and deuterium.

3. A triarylamine derivative according to claim 1, characterized in that: The *-Ar1-(Rz)n is selected from any one of the groups shown below; 4. A triarylamine derivative according to claim 1, characterized in that: The Ar2 is selected from any one of the groups shown below; 5. A triarylamine derivative according to claim 1, characterized in that: The L1 and L2 are the same or different from each other and are selected from a single bond or any one of the groups shown below; The R7 are the same as or different from each other and are selected from hydrogen and deuterium.

6. A triarylamine derivative, characterized in that The triarylamine derivative is selected from any one of the following structures; 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 of either the anode or the cathode, characterized in that: The organic layer comprises at least one or more triarylamine derivatives according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic layer is located outside of any one of the anode and the cathode, The organic layer includes a covering layer, and the covering layer includes at least one or more triarylamine derivatives according to any one of claims 1 to 6.

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