Triarylamine derivative and organic electroluminescent device thereof
By using triarylamine derivatives as hole transport layer and cover layer materials in organic electroluminescent devices, the problem of low device performance in the prior art is solved, and higher luminescence efficiency and service life are achieved.
Patent Information
- Application Number
- CN202411565004.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-11-04
- Publication Date
- 2025-02-14
AI Technical Summary
The existing organic electroluminescent devices have low performance, including low luminous efficiency and service life.
A triarylamine derivative is used as the hole transport layer material and cover material. Through its suitable HOMO energy level and good hole mobility, the injection and transmission efficiency of holes are improved, and through high refractive index and high glass The transition temperature is improved to improve the light extraction efficiency and thermal stability of the device.
It effectively improves the luminous efficiency and service life of organic electroluminescent devices, reduces energy consumption, and enhances the stability and performance of the device.
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Abstract
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 electroluminescent devices (OLEDs) have the characteristics of fast response, wide viewing angle, light and thin body, wide operating temperature range, low energy consumption, good color purity, high clarity, and strong flexibility. They are widely used in many fields such as display and lighting.
[0003] Organic electroluminescence refers to the process in which, when an organic photoelectric material is driven by electric current or electric field, electrons and holes are injected and transmitted from the cathode and anode into the organic layer respectively, causing the two to recombine in the light-emitting layer to produce excitons. The excitons transfer energy to the organic luminescent 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, producing luminescence.
[0004] Organic electroluminescent devices are usually classic sandwich structures consisting of cathode, anode and organic functional layers. 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 anode, cathode and organic layer. The organic layer includes hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, covering layer and other functional layers.
[0005] With the needs of the organic light-emitting device market, the luminous efficiency and service life of organic light-emitting devices have become important issues that need to be solved at present. For hole transport layer materials, the triplet energy level is improved to obtain a suitable HOMO energy level, and the mobility of holes is improved, which is conducive to the injection and transmission balance of holes and electrons, improves the effective recombination of holes and electrons in the light-emitting layer, and improves the luminous efficiency of the device; at the same time, 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 doping layer / p-type doping layer serves as a connecting layer between light-emitting units to improve the recombination of holes / electrons into excitons in the light-emitting unit; in addition, the cover layer material needs to reduce the plasma resonance effect between the cathode material, improve the light extraction efficiency inside the device, reduce the absorption coefficient in the visible light band, reduce the accumulation of heat inside the device, and have a high glass transition temperature and strong film stability. Therefore, it is crucial to design an organic electroluminescent material that can reduce energy consumption, improve the luminous efficiency of the device, and extend the service life of the device. Summary of the invention
[0006] 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.
[0007] The present invention provides a triarylamine derivative, wherein the triarylamine derivative has a structure as shown in Formula I,
[0008]
[0009] In Formula I, Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused ring, and a substituted or unsubstituted C2-C30 heteroaryl group;
[0010] The ring A is selected from substituted or unsubstituted C3-C7 aliphatic rings;
[0011] 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;
[0012] The L1 is selected from the group shown in formula II;
[0013]
[0014] The v's are the same or different from each other and are selected from CH or N atoms. When v is bonded to other groups, the v's are selected from C atoms;
[0015] The R1, R a , R b , R c , R d The same as or different from each other, and any one selected from hydrogen, deuterium, cyano, halogen, 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 C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroaryl;
[0016] a is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, b is selected from 0, 1, 2, 3, 4, 5, 6 or 7, c is selected from 0, 1, 2 or 3, d is selected from 0, 1 or 2, e is selected from 0, 1, 2, 3 or 4, when there are two or more R a When two or more R a Same or different from each other, or two adjacent R a They can be connected to each other to form one or more substituted or unsubstituted rings; when there are two or more R b When two or more R b Same or different from each other, or two adjacent R bThey can be connected to each other to form one or more substituted or unsubstituted rings; when there are two or more R c When two or more R c Same or different from each other, or two adjacent R c They can be connected to each other to form one or more substituted or unsubstituted rings; when there are two or more R d When two or more R d are identical or different to each other; when there are two or more R1s, the two or more R1s are identical or different to each other, or two adjacent R1s may be connected to each other to form one or more substituted or unsubstituted rings;
[0017] The L2 and L3 are the same as or different from each other and are selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a divalent substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, and a combination thereof.
[0018] 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.
[0019] Beneficial effects: The triarylamine derivatives shown in formula I provided by the present invention are applied to organic electroluminescent devices as hole transport layer materials, which can effectively improve the luminous efficiency and service life of the device. This is because the structure shown in formula I has a suitable HOMO energy level and good hole mobility, which can reduce the energy barrier that needs to be overcome during hole transport, is beneficial to the injection and transport of holes, and increases the effective recombination of excitons in the light-emitting layer; at the same time, when it is used as a covering layer material, it has a good refractive index, a high glass transition temperature, good film-forming properties, and high thermal stability, so that a device with high performance can also be obtained. DETAILED DESCRIPTION
[0020] 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.
[0021] In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.
[0022] In the present specification, "*" means a portion connecting to another substituent.
[0023] 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.
[0024] 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.
[0025] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine or iodine.
[0026] 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.
[0027] 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.
[0028] 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.
[0029] 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 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. 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.
[0030] 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.
[0031] 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.
[0032] 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.
[0033] 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.
[0034] 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.
[0035] 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.
[0036] The divalent fused ring group of an aromatic ring and an aliphatic ring described in the present invention refers to a 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.
[0037] 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.
[0038] 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, yl, peryl, fluoranthene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazolyl, 9-phenylcarbazolyl, 9,9'-spirobifluorenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, pyrrolidone, The invention also includes oxadiazole, oxazolyl, thiazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, and the like, but is not limited thereto.
[0039] 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:
[0040]
[0041] 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.
[0042] The present invention provides a triarylamine derivative, wherein the triarylamine derivative has a structure as shown in Formula I,
[0043]
[0044] In Formula I, Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused ring, and a substituted or unsubstituted C2-C30 heteroaryl group;
[0045] The ring A is selected from substituted or unsubstituted C3-C7 aliphatic rings;
[0046] 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;
[0047] The L1 is selected from the group shown in formula II;
[0048]
[0049] The v's are the same or different from each other and are selected from CH or N atoms. When v is bonded to other groups, the v's are selected from C atoms;
[0050] The R1, R a , R b , R c , R d The same as or different from each other, and any one selected from hydrogen, deuterium, cyano, halogen, 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 C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroaryl;
[0051] a is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, b is selected from 0, 1, 2, 3, 4, 5, 6 or 7, c is selected from 0, 1, 2 or 3, d is selected from 0, 1 or 2, e is selected from 0, 1, 2, 3 or 4, when there are two or more R a When two or more R a Same or different from each other, or two adjacent R a They can be connected to each other to form one or more substituted or unsubstituted rings; 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 one or more substituted or unsubstituted rings; when there are two or more R c When two or more R c Same or different from each other, or two adjacent R c They can be connected to each other to form one or more substituted or unsubstituted rings; when there are two or more R d When two or more R d are identical or different to each other; when there are two or more R1s, the two or more R1s are identical or different to each other, or two adjacent R1s may be connected to each other to form one or more substituted or unsubstituted rings;
[0052] The L2 and L3 are the same as or different from each other and are selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a divalent substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, and a combination thereof.
[0053] Preferably, the formula II is selected from any one of the groups shown below;
[0054]
[0055] Said R1 and R2 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzofuranyl or benzothiophenyl;
[0056] The a1 is selected from 0, 1, 2, 3 or 4, the a2 is selected from 0, 1, 2 or 3, the a3 is selected from 0, 1 or 2, the a4 is selected from 0 or 1, the a5 is selected from 0, 1, 2, 3, 4, 5 or 6, and the a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
[0057] Preferably, the Any one selected from the following groups;
[0058]
[0059] R3, R b The same as or different from each other, and are selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, or benzothiophenyl;
[0060] The b1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the b2 is selected from 0, 1, 2, 3 or 4, the b3 is selected from 0, 1, 2, 3, 4, 5 or 6, the b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, and the b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.
[0061] Preferably, the Any one selected from the following groups;
[0062]
[0063] The R c , R dThe same as or different from each other, and are selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl, or benzothiophenyl;
[0064] The c1 is selected from 0, 1, 2 or 3, the c2 is selected from 0, 1 or 2, the c3 is selected from 0 or 1, the c4 is selected from 0, 1, 2, 3, 4 or 5, the c5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the c6 is selected from 0, 1, 2, 3 or 4.
[0065] Preferably, Ar1 is selected from any one of the following groups:
[0066]
[0067] The R4 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzofuranyl or benzothiophenyl;
[0068] 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 d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, the d 10 Select from 0 or 1.
[0069] Preferably, L2 and L3 are the same or different from each other and are selected from a single bond or any one of the groups shown below;
[0070]
[0071]
[0072] The R5 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane or benzocyclohexane;
[0073] 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 or 6, the e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the e7 is selected from 0, 1, 2, 3, 4 or 5.
[0074] Preferably, the triarylamine derivative is selected from any one of the following structures,
[0075]
[0076]
[0077]
[0078]
[0079]
[0080]
[0081]
[0082]
[0083]
[0084]
[0085]
[0086] 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.
[0087] 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.
[0088] 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.
[0089] 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.
[0090] Preferably, the hole transport layer described in the present invention comprises a first hole transport layer, a second hole transport layer and / or a third 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, the third hole transport layer is located between the second hole transport layer and the light-emitting layer, and at least one of the first hole transport layer, the second hole transport layer and / or the third hole transport layer comprises any one or more of the triarylamine derivatives described in the present invention.
[0091] 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.
[0092] 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.
[0093] 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.
[0094] Preferably, the organic layer described in the present invention is located outside any one of the anode and the cathode, and the organic layer comprises a covering layer, and the covering layer comprises any one or more of the triarylamine derivatives described in the present invention.
[0095] 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:
[0096] 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.
[0097] 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.
[0098] 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.
[0099] 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.
[0100] 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-naphthyl)anthracene ( α-AND), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1":4",1"'-quadrphenyl]-4,4"'-diamino (4PNPB), 1,3,5-tri(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 the like. The doping material of the light-emitting layer 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)picolinyl Iridium (FIrpic), 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 not limited to these.
[0101] 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.
[0102] 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.
[0103] 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.
[0104] 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.
[0105] 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. The triarylamine derivative of the present invention is preferred.
[0106] 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.
[0107] 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.
[0108] The organic light emitting device of the present invention may be a top emission type, a bottom emission type or a bidirectional emission type.
[0109] 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.
[0110] 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 specific synthetic route is as follows:
[0111]
[0112] Among them, X a are the same as or different from each other and are selected from any one of Cl, Br, and I; Ring A, x, Ar1, L1-L3, R a -R d , the limitations of ad are the same as above.
[0113] 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.
[0114] 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.
[0115] Preparation and characterization of compounds
[0116] Description of raw materials, reagents and characterization equipment:
[0117] 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.
[0118] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;
[0119] The elemental analysis used the Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg;
[0120] Synthesis Example 1: Preparation of Intermediate c-261:
[0121]
[0122] Under nitrogen protection, m-261 (16.04 g, 100.00 mmol), n-261 (21.31 g, 100.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), K2CO3 (24.88 g, 180 mmol) and 450 mL (toluene: ethanol: water = 2:1:1) mixed solvent were added to the reaction bottle, the mixture was stirred, and the mixed solution of the above reactants was heated to reflux for 4.5 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 obtained solid was recrystallized with toluene: methanol = 10:1, and dried to obtain the raw material c-261 (19.40 g, yield 78%), HPLC purity ≧99.79%. Mass spectrum m / z: 248.0350 (theoretical value: 248.0365).
[0123] Synthesis Example 2: Preparation of Intermediate c-276:
[0124]
[0125] According to the same preparation method as in Synthesis Example 1, m-261 was replaced with an equal molar amount of m-276 to obtain intermediate c-276 (22.11 g) with HPLC purity ≧99.75%. Mass spectrum m / z: 294.0257 (theoretical value: 294.0270).
[0126] Synthesis Example 3: Preparation of Intermediate C-289:
[0127]
[0128] According to the same preparation method as in Synthesis Example 1, m-261 was replaced by an equal mole of m-289, and n-261 was replaced by an equal mole of n-289 to obtain intermediate c-289 (20.79 g) with HPLC purity ≧99.80%. Mass spectrum m / z: 284.0442 (theoretical value: 284.0426).
[0129] Synthesis Example 4: Preparation of Intermediate c-313:
[0130]
[0131] According to the same preparation method as in Synthesis Example 1, m-261 was replaced by an equal mole of m-313, and n-261 was replaced by an equal mole of n-313 to obtain intermediate c-313 (20.19 g) with HPLC purity ≧99.73%. Mass spectrum m / z: 272.0416 (theoretical value: 272.0426).
[0132] Synthesis Example 5: Preparation of Intermediate c-314:
[0133]
[0134] According to the same preparation method as in Synthesis Example 1, m-261 was replaced by an equal mole of m-313, and n-261 was replaced by an equal mole of n-314 to obtain intermediate c-314 (23.10 g) with HPLC purity ≧99.76%. Mass spectrum m / z: 320.0445 (theoretical value: 320.0426).
[0135] Synthesis Example 6: Preparation of Compound 37:
[0136]
[0137] Preparation of intermediate A-37
[0138] Under nitrogen protection, a-37 (29.80 g, 75.00 mmol), b-37 (17.65 g, 75.00 mmol), Pd(OAc)2 (0.22 g, 1.00 mmol), P(t-Bu)3 (4.00 mL of 0.5 M toluene solution, 2.00 mmol), NaOt-Bu (14.41 g, 150.00 mmol) and 350 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 5.5 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 distillation under reduced pressure. The temperature was lowered for crystallization, and suction was filtered. The obtained solid was recrystallized with toluene: ethanol = 12:1 to obtain intermediate A-37 (31.86 g, yield 77%), HPLC purity ≧ 99.87%. Mass spectrum m / z: 551.2626 (theoretical value: 551.2613).
[0139] Preparation of compound 37:
[0140] Under nitrogen protection, intermediate A-37 (24.83 g, 45.00 mmol), c-37 (13.01 g, 45.00 mmol), Pd2(dba)3 (0.61 g, 0.67 mmol), BINAP (0.56 g, 0.90 mmol), NaOt-Bu (8.65 g, 90.00 mmol) and 250 ml toluene solvent were added, and the mixture was stirred. The mixed solution of the above reactants was heated to reflux for 4.5 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 37 (27.02 g, yield 79%), HPLC purity ≧99.95%. Mass spectrum m / z: 759.2950 (theoretical value: 759.2960). Theoretical element content (%) C 56 H 41 NS: C, 88.50; H, 5.44; N, 1.84. Measured element content (%): C, 88.48; H, 5.39; N, 1.87. Synthesis Example 7: Preparation of Compound 38:
[0141]
[0142] According to the same preparation method as in Synthesis Example 6, c-37 was replaced by an equal molar amount of c-38 to obtain compound 38 (26.33 g), HPLC purity ≧99.96%. Mass spectrum m / z: 759.2948 (theoretical value: 759.2960). Theoretical element content (%) C 56 H 41 NS: C, 88.50; H, 5.44; N, 1.84. Measured element content (%): C, 88.47; H, 5.40; N, 1.86.
[0143] Synthesis Example 8: Preparation of Compound 83:
[0144]
[0145] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal molar amount of a-83 to obtain compound 83 (26.81 g), HPLC purity ≧99.92%. Mass spectrum m / z: 815.3570 (theoretical value: 815.3586). Theoretical element content (%) C 60 H 49 NS: C, 88.30; H, 6.05; N, 1.72. Measured element content (%): C, 88.28; H, 6.08; N, 1.69.
[0146] Synthesis Example 9: Preparation of Compound 100:
[0147]
[0148] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal molar amount of a-100 to obtain compound 100 (26.44 g), HPLC purity ≧99.90%. Mass spectrum m / z: 815.3598 (theoretical value: 815.3586). Theoretical element content (%) C 60 H 49 NS: C, 88.30; H, 6.05; N, 1.72. Measured element content (%): C, 88.28; H, 6.08; N, 1.69.
[0149] Synthesis Example 10: Preparation of Compound 127:
[0150]
[0151] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal molar amount of b-127 to obtain compound 127 (26.34 g), HPLC purity ≧ 99.91%. Mass spectrum m / z: 835.3290 (theoretical value: 835.3273). Theoretical element content (%) C 62 H 45 NS: C, 89.07; H, 5.43; N, 1.68. Measured element content (%): C, 89.10; H, 5.39; N, 1.70.
[0152] Synthesis Example 11: Preparation of Compound 130:
[0153]
[0154] According to the same preparation method as in Synthesis Example 6, b-37 was replaced with an equal molar amount of b-130 to obtain compound 130 (27.52 g), HPLC purity ≧99.98%. Mass spectrum m / z: 773.3105 (theoretical value: 773.3116). Theoretical element content (%) C 57 H 43 NS: C, 88.45; H, 5.60; N, 1.81. Measured element content (%): C, 88.48; H, 5.57; N, 1.79.
[0155] Synthesis Example 12: Preparation of Compound 131:
[0156]
[0157] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal molar amount of a-131, b-37 was replaced by an equal molar amount of b-130, and c-37 was replaced by an equal molar amount of c-38 to obtain compound 131 (26.82 g), HPLC purity ≧99.96%. Mass spectrum m / z: 773.3103 (theoretical value: 773.3116). Theoretical element content (%) C 57 H 43 NS: C, 88.45; H, 5.60; N, 1.81. Measured element content (%): C, 88.47; H, 5.58; N, 1.78.
[0158] Synthesis Example 13: Preparation of Compound 148:
[0159]
[0160] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-148 to obtain compound 148 (27.17 g), HPLC purity ≧99.97%. Mass spectrum m / z: 773.3106 (theoretical value: 773.3116). Theoretical element content (%) C 57 H 43 NS: C, 88.45; H, 5.60; N, 1.81. Measured element content (%): C, 88.49; H, 5.59; N, 1.80.
[0161] Synthesis Example 14: Preparation of Compound 163:
[0162]
[0163] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal molar amount of a-163, b-37 was replaced by an equal molar amount of b-130, and c-37 was replaced by an equal molar amount of c-163 to obtain compound 163 (26.26 g), HPLC purity ≧99.94%. Mass spectrum m / z: 777.3349 (theoretical value: 777.3367). Theoretical element content (%) C 57 H 39 D4NS: C, 87.99; H, 6.09; N, 1.80. Measured element content (%): C, 87.95; H, 6.11; N, 1.77.
[0164] Synthesis Example 15: Preparation of Compound 203:
[0165]
[0166] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-203, and b-37 was replaced by an equal mole of b-130 to obtain compound 203 (26.33 g), HPLC purity ≧99.92%. Mass spectrum m / z: 823.3258 (theoretical value: 823.3273). Theoretical element content (%) C 61 H 45 NS: C, 88.91; H, 5.50; N, 1.70. Measured element content (%): C, 88.88; H, 5.47; N, 1.73.
[0167] Synthesis Example 16: Preparation of Compound 224:
[0168]
[0169] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-224, and b-37 was replaced by an equal mole of b-130 to obtain compound 224 (25.59 g), HPLC purity ≧99.91%. Mass spectrum m / z: 778.3447 (theoretical value: 778.3430). Theoretical element content (%) C 57 H 38 D5NS: C, 87.88; H, 6.21; N, 1.80. Measured element content (%): C, 87.90; H, 6.17; N, 1.78.
[0170] Synthesis Example 17: Preparation of Compound 225:
[0171]
[0172] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-225, and b-37 was replaced by an equal mole of b-130 to obtain compound 225 (26.60 g), HPLC purity ≧99.96%. Mass spectrum m / z: 787.3286 (theoretical value: 787.3273). Theoretical element content (%) C 58 H 45 NS: C, 88.40; H, 5.76; N, 1.78. Measured element content (%): C, 88.37; H, 5.80; N, 1.81.
[0173] Synthesis Example 18: Preparation of Compound 231:
[0174]
[0175] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-231, and b-37 was replaced by an equal mole of b-130 to obtain compound 231 (27.04 g), HPLC purity ≧99.93%. Mass spectrum m / z: 845.3523 (theoretical value: 845.3511). Theoretical element content (%) C 60 H 51 NSSi: C, 85.16; H, 6.08; N, 1.66. Measured element content (%): C, 85.20; H, 6.11; N, 1.62.
[0176] Synthesis Example 19: Preparation of Compound 244:
[0177]
[0178] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-244, and b-37 was replaced by an equal mole of b-130 to obtain compound 244 (27.81 g), HPLC purity ≧99.95%. Mass spectrum m / z: 823.3285 (theoretical value: 823.3273). Theoretical element content (%) C 61 H 45 NS: C, 88.91; H, 5.50; N, 1.70. Measured element content (%): C, 88.87; H, 5.48; N, 1.75.
[0179] Synthesis Example 20: Preparation of Compound 261:
[0180]
[0181] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-261 to obtain compound 261 (26.61 g), HPLC purity ≧99.92%. Mass spectrum m / z: 777.3351 (theoretical value: 777.3367). Theoretical element content (%) C 57 H 39 D4NS: C, 87.99; H, 6.09; N, 1.80. Measured element content (%): C, 87.96; H, 6.11; N, 1.77.
[0182] Synthesis Example 21: Preparation of Compound 271:
[0183]
[0184] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-271 to obtain compound 271 (28.69 g), HPLC purity ≧99.95%. Mass spectrum m / z: 849.3443 (theoretical value: 849.3429). Theoretical element content (%) C 63 H 47 NS: C, 89.01; H, 5.57; N, 1.65. Measured element content (%): C, 89.05; H, 5.60; N, 1.62.
[0185] Synthesis Example 22: Preparation of Compound 276:
[0186]
[0187] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-276 to obtain compound 276 (26.70 g), HPLC purity ≧99.93%. Mass spectrum m / z: 823.3257 (theoretical value: 823.3273). Theoretical element content (%) C 61 H 45 NS: C, 88.91; H, 5.50; N, 1.70. Measured element content (%): C, 88.89; H, 5.47; N, 1.74.
[0188] Synthesis Example 23: Preparation of Compound 289:
[0189]
[0190] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal molar amount of a-131, b-37 was replaced by an equal molar amount of b-130, and c-37 was replaced by an equal molar amount of c-289 to obtain compound 289 (25.64 g), HPLC purity ≧99.91%. Mass spectrum m / z: 813.3443 (theoretical value: 813.3429). Theoretical element content (%) C 60 H 47 NS: C, 88.52; H, 5.82; N, 1.72. Measured element content (%): C, 88.49; H, 5.85; N, 1.78.
[0191] Synthesis Example 24: Preparation of Compound 313:
[0192]
[0193] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-313 to obtain compound 313 (25.27 g), HPLC purity ≧99.93%. Mass spectrum m / z: 801.3414 (theoretical value: 801.3429). Theoretical element content (%) C 59 H 47 NS: C, 88.35; H, 5.91; N, 1.75. Measured element content (%): C, 88.31; H, 5.89; N, 1.78.
[0194] Synthesis Example 25: Preparation of Compound 314:
[0195]
[0196] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-314 to obtain compound 314 (26.40 g), HPLC purity ≧99.95%. Mass spectrum m / z: 849.3448 (theoretical value: 849.3429). Theoretical element content (%) C 63 H 47 NS: C, 89.01; H, 5.57; N, 1.65. Measured element content (%): C, 89.06; H, 5.60; N, 1.61.
[0197] Synthesis Example 26: Preparation of Compound 321:
[0198]
[0199] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-321 to obtain compound 321 (25.46 g), HPLC purity ≧99.94%. Mass spectrum m / z: 774.3050 (theoretical value: 774.3069). Theoretical element content (%) C 56 H 42 N2S: C, 86.79; H, 5.46; N, 3.61. Measured element content (%): C, 86.82; H, 5.42; N, 3.58.
[0200] Synthesis Example 27: Preparation of Compound 334:
[0201]
[0202] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-334 to obtain compound 334 (25.96 g), HPLC purity ≧99.92%. Mass spectrum m / z: 823.3257 (theoretical value: 823.3273). Theoretical element content (%) C 61 H 45 NS: C, 88.91; H, 5.50; N, 1.70. Measured element content (%): C, 88.89; H, 5.46; N, 1.73.
[0203] Synthesis Example 28: Preparation of Compound 354:
[0204]
[0205] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal molar amount of a-354, b-37 was replaced by an equal molar amount of b-130, and c-37 was replaced by an equal molar amount of c-354 to obtain compound 354 (26.70 g), HPLC purity ≧99.90%. Mass spectrum m / z: 823.3291 (theoretical value: 823.3273). Theoretical element content (%) C 61 H 45 NS: C, 88.91; H, 5.50; N, 1.70. Measured element content (%): C, 88.89; H, 5.53; N, 1.68.
[0206] Synthesis Example 29: Preparation of Compound 356:
[0207]
[0208] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-356, and b-37 was replaced by an equal mole of b-130 to obtain compound 356 (27.16 g), HPLC purity ≧99.92%. Mass spectrum m / z: 849.3412 (theoretical value: 849.3429). Theoretical element content (%) C 63 H 47 NS: C, 89.01; H, 5.57; N, 1.65. Measured element content (%): C, 89.05; H, 5.61; N, 1.64.
[0209] Synthesis Example 30: Preparation of Compound 362:
[0210]
[0211] According to the same preparation method as in Synthesis Example 6, a-37 was replaced with an equal molar amount of a-362 to obtain compound 362 (25.68 g), HPLC purity ≧99.96%. Mass spectrum m / z: 760.2926 (theoretical value: 760.2912). Theoretical element content (%) C 55 H 40 N2S: C, 86.81; H, 5.30; N, 3.68. Measured element content (%): C, 86.79; H, 5.27; N, 3.71.
[0212] Synthesis Example 31: Preparation of Compound 364:
[0213]
[0214] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-364 to obtain compound 364 (24.50 g), HPLC purity ≧99.94%. Mass spectrum m / z: 697.2823 (theoretical value: 697.2803). Theoretical element content (%) C 51 H 39 NS: C, 87.77; H, 5.63; N, 2.01. Measured element content (%): C, 87.80; H, 5.59; N, 2.05.
[0215] Synthesis Example 32: Preparation of Compound 411:
[0216]
[0217] According to the same preparation method as in Synthesis Example 6, a-37 was replaced by an equal mole of a-411, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-411 to obtain compound 411 (26.12 g), HPLC purity ≧99.92%. Mass spectrum m / z: 773.3132 (theoretical value: 773.3116). Theoretical element content (%) C 57 H 43 NS: C, 88.45; H, 5.60; N, 1.81. Measured element content (%): C, 88.48; H, 5.57; N, 1.79.
[0218] Synthesis Example 33: Preparation of Compound 420:
[0219]
[0220] According to the same preparation method as in Synthesis Example 6, b-37 was replaced by an equal mole of b-130, and c-37 was replaced by an equal mole of c-420 to obtain compound 420 (23.41 g), HPLC purity ≧99.93%. Mass spectrum m / z: 702.3134 (theoretical value: 702.3117). Theoretical element content (%) C 51 H 34 D5NS: C, 87.14; H, 6.31; N, 1.99. Measured element content (%): C, 87.17; H, 6.28; N, 1.96.
[0221] [Device Example 1]
[0222] 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.
[0223] The vacuum evaporation method is used to sequentially evaporate a hole injection layer HI (60 nm); a hole transport layer compound 37 (80 nm); a light-emitting layer RH:RD=98:2 (mass ratio, 40 nm); a hole blocking layer HB (45 nm); an electron transport layer ET:Liq=1:1 (mass ratio, 30 nm); an electron injection layer LiF (1.0 nm); and a cathode Al (120 nm) on a cleaned ITO substrate to prepare an organic electroluminescent device.
[0224]
[0225] [Device Example 2-28]
[0226] The compound 38, compound 83, compound 100, compound 127, compound 130, compound 131, compound 148, compound 163, compound 203, compound 224, compound 225, compound 231, compound 244, compound 261, compound 271, compound 276, compound 289, compound 313, compound 314, compound 321, compound 334, compound 354, compound 356, compound 362, compound 364, compound 411 or compound 420 of the present invention are used to replace compound 37 in device example 1 as the hole transport layer material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 1.
[0227] [Comparative Device Examples 1-3]
[0228] An organic electroluminescent device was prepared by the same preparation method as in Device Example 1 except that Comparative Compound 1, Comparative Compound 2 or Comparative Compound 3 was used to replace Compound 37 in Device Example 1 as the hole transport layer material.
[0229] 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.
[0230] The test results of the luminescent characteristics of the organic electroluminescent devices obtained in device embodiments 1 to 28 of the present invention and comparative embodiments 1 to 3 are shown in Table 1 below.
[0231]
[0232]
[0233] [Device Example 29]
[0234] 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.
[0235] The vacuum evaporation method is used to sequentially evaporate the hole injection layer HI (55nm); the first hole transport layer HT (20nm); the second hole transport layer compound 37 (60nm); the light-emitting layer GH:GD=92:8 (mass ratio, 40nm); the hole blocking layer HB (35nm) the electron transport layer ET:Liq=1:1 (mass ratio, 35nm); the electron injection layer LiF (0.8nm); and the cathode Al (130nm) on the cleaned ITO substrate to prepare an organic electroluminescent device.
[0236]
[0237] [Device Examples 29-56]
[0238] Compound 38, compound 83, compound 100, compound 127, compound 130, compound 131, compound 148, compound 163, compound 203, compound 224, compound 225, compound 231, compound 244, compound 261, compound 271, compound 276, compound 289, compound 313, compound 314, compound 321, compound 334, compound 354, compound 356, compound 362, compound 364, compound 411 or compound 420 of the present invention are used to replace compound 37 in device example 29 as the second hole transport layer material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 29.
[0239] [Comparative Device Examples 4-6]
[0240] An organic electroluminescent device was prepared by the same preparation method as Device Example 29, except that Comparative Compound 1, Comparative Compound 2 or Comparative Compound 3 was used to replace Compound 37 in Device Example 29 as the second hole transport layer material.
[0241] The test results of the luminescent characteristics of the organic electroluminescent devices obtained in device embodiments 29 to 56 of the present invention and comparative embodiments 4 to 6 are shown in Table 2 below.
[0242]
[0243]
[0244] 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.
[0245] [Device Example 57]
[0246] First, the ITO / Ag / 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.
[0247] The method of vacuum evaporation was used to sequentially deposit a hole injection layer HI (60 nm); a hole transport layer HT (80 nm); a light-emitting layer RH:RD=97:3 (mass ratio, 40 nm); a hole blocking layer HB (45 nm); an electron transport layer ET-3:Liq=1:1 (mass ratio, 35 nm); an electron injection layer LiF (0.8 nm); a cathode Mg:Ag=1:9 (mass ratio, 12 nm); and a covering layer compound 37 (80 nm) on a cleaned ITO / Ag / ITO substrate, thereby preparing an organic electroluminescent device.
[0248]
[0249] [Device Examples 58-74]
[0250] Using Compound 38, Compound 130, Compound 131, Compound 148, Compound 163, Compound 225, Compound 244, Compound 261, Compound 271, Compound 276, Compound 314, Compound 321, Compound 334, Compound 354, Compound 356, Compound 364 or Compound 411 of the present invention respectively instead of Compound 37 in Device Example 57 as the covering layer material, except that the above-mentioned materials are used, an organic electroluminescent device is prepared by the same preparation method as Device Example 57.
[0251] [Comparative Device Example 7]
[0252] An organic electroluminescent device was prepared by the same preparation method as Device Example 57, except that Comparative Compound 4 was used instead of Compound 37 in Device Example 57 as the covering layer material.
[0253] The test results of the luminescent characteristics of the organic electroluminescent devices obtained in device embodiments 57 to 74 of the present invention and comparative example 7 are shown in Table 3 below.
[0254]
[0255] According to the data results in Table 3, it can be seen that the triarylamine derivative represented by formula I of the present invention is applied to an organic electroluminescent device as a covering layer material, which can effectively couple the light inside the device out, reduce the accumulation of Joule heat inside the device, thereby improving the luminous efficiency of the device and extending the service life.
[0256] 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 a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused ring, and a substituted or unsubstituted C2-C30 heteroaryl group; The ring A is selected from substituted or unsubstituted C3-C7 aliphatic rings; 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 L1 is selected from the group shown in formula II; The v's are the same or different from each other and are selected from CH or N atoms. When v is bonded to other groups, the v's are selected from C atoms; The R1, R a , R b , R c , R d The same as or different from each other, and any one selected from hydrogen, deuterium, cyano, halogen, 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 C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroaryl; a is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, b is selected from 0, 1, 2, 3, 4, 5, 6 or 7, c is selected from 0, 1, 2 or 3, d is selected from 0, 1 or 2, e is selected from 0, 1, 2, 3 or 4, when there are two or more R a When two or more R a Same or different from each other, or two adjacent R a They can be connected to each other to form one or more substituted or unsubstituted rings; 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 one or more substituted or unsubstituted rings; when there are two or more R c When two or more R c Same or different from each other, or two adjacent R c They can be connected to each other to form one or more substituted or unsubstituted rings; when there are two or more R d When two or more R d are identical or different to each other; when there are two or more R1s, the two or more R1s are identical or different to each other, or two adjacent R1s may be connected to each other to form one or more substituted or unsubstituted rings; The L2 and L3 are the same as or different from each other and are selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a divalent substituted or unsubstituted fused ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, and a combination thereof.
2. A triarylamine derivative according to claim 1, characterized in that: The formula II is selected from any one of the groups shown below; Said R1 and R2 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzofuranyl or benzothiophenyl; The a1 is selected from 0, 1, 2, 3 or 4, the a2 is selected from 0, 1, 2 or 3, the a3 is selected from 0, 1 or 2, the a4 is selected from 0 or 1, the a5 is selected from 0, 1, 2, 3, 4, 5 or 6, and the a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
3. A triarylamine derivative according to claim 1, characterized in that: Said Any one selected from the following groups; R3, R b The same as or different from each other, and are selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, or benzothiophenyl; The b1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the b2 is selected from 0, 1, 2, 3 or 4, the b3 is selected from 0, 1, 2, 3, 4, 5 or 6, the b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, and the b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.
4. A triarylamine derivative according to claim 1, characterized in that: Said Any one selected from the following groups; The R c , R d The same as or different from each other, and are selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl, or benzothiophenyl; The c1 is selected from 0, 1, 2 or 3, the c2 is selected from 0, 1 or 2, the c3 is selected from 0 or 1, the c4 is selected from 0, 1, 2, 3, 4 or 5, the c5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the c6 is selected from 0, 1, 2, 3 or 4.
5. A triarylamine derivative according to claim 1, characterized in that: The Ar1 is selected from any one of the following groups; The R4 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, halogen, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzofuranyl or benzothiophenyl; 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 d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, the d 10 Select from 0 or 1.
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. The organic electroluminescent device according to claim 7, wherein the organic layer is located between the anode and the cathode, wherein: The organic layer comprises a hole transport region, and 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 contains any one or more of the triarylamine derivatives according to any one of claims 1 to 6.
10. The organic electroluminescent device according to claim 7, wherein the organic layer is located outside any one of the anode and the cathode, wherein: The organic layer comprises a covering layer, and the covering layer comprises any one or more of the triarylamine derivatives according to any one of claims 1 to 6.