Organic light-emitting device
By employing the hole transport region of Formula 1 and the electron transport region of Formula 2 in OLED devices, the problems of low luminous efficiency and short lifetime in existing OLED devices are solved, achieving efficient exciton recombination and improved material stability.
Patent Information
- Application Number
- CN202511565624.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-10-29
- Publication Date
- 2025-12-19
AI Technical Summary
In existing OLED devices, the mobility of hole transport materials is higher than that of electron transport materials, which leads to a decrease in the probability of exciton recombination and a decrease in luminous efficiency. At the same time, hole leakage causes device aging, poor material film formation and stability, and affects device lifespan.
The method employs a hole transport region with structure 1 and an electron transport region with structure 2, which effectively blocks the diffusion of electrons and holes, limits the recombination region within the light-emitting layer, increases the exciton recombination probability, and avoids electron and hole leakage.
It significantly improves the luminous efficiency of OLED devices, extends their lifespan, avoids device aging, and enhances the film-forming properties and stability of materials.
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Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to the technical field of organic electroluminescence, in particular to an organic electroluminescence device. BACKGROUND
[0002] OLED, organic light emitting device, has the advantages of self-luminescence, strong color contrast effect, low power consumption, flexibility, fast response speed and so on. In the past two decades, OLED is the most popular and fastest developing display and solid-state lighting technology. As one of the cores of modern information industry, the development space of OLED is very broad.
[0003] The light emission of OLED belongs to electroluminescence, which refers to the phenomenon that organic materials emit light under the excitation of electric energy. The light emission principle is as follows: under the action of an external electric field, holes generated by the anode and electrons generated by the cathode are injected into the hole transport layer and the electron transport layer respectively after overcoming the interface energy barrier, and then migrate to the light emitting layer. The electrons and holes recombine in the light emitting layer to form excited state excitons. At this time, the excited state is not stable, and the excitons return to the ground state by radiative transition, while releasing energy and generating photons. OLED is usually composed of an anode, a cathode and layers with special functions. Between the anode and the light emitting layer, a hole injection layer (HIL), a hole transport layer (HTL) and an electron blocking layer (EBL) can be inserted. Between the cathode and the light emitting layer, an electron injection layer (EIL), an electron transport layer (ETL) and a hole blocking layer (HBL) can be inserted. The injection layer and the transport layer improve the transmission of charges to the emitting layer, while the blocking layer prevents the loss of charges in the opposite direction and limits the excitons. This multi-layer structure reduces the injection barrier of holes and electrons, improves the stability, light emission efficiency and service life of OLED.
[0004] The performance of OLED device is largely limited by the hole transport type material and the electron transport type material. Therefore, developing organic hole transport type materials and electron transport type materials with energy level matching and balanced carrier transport is an effective means to improve the light emission efficiency and service life of the device. However, in the existing organic materials, the mobility of hole transport materials is generally higher than that of electron transport materials, which makes the exciton recombination region close to the electron transport layer. This problem reduces the probability of holes and electrons recombining into excitons in the light emitting layer, resulting in a decrease in the light emission efficiency of the device. At the same time, the ions produced by the leakage of holes into the electron transport layer cause serious aging of the device. On the other hand, the film-forming property and stability of the existing hole transport materials and electron transport materials are poor, which leads to a shortened service life of the device and a reduced performance of the device. These problems have been affecting the development of OLED. Therefore, it is particularly important to select more suitable and better performing OLED materials or material combinations. SUMMARY
[0005] In order to solve the above problems, the present application provides an organic electroluminescent device, which improves the low luminous efficiency and short service life of the prior art, and significantly improves the performance of the organic electroluminescent device.
[0006] Specifically, the present application provides an organic electroluminescent device, which comprises an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is between the anode and the light-emitting layer, the electron transport region is between the light-emitting layer and the cathode, the hole transport region comprises a triarylamine compound represented by Formula 1, and the electron transport region comprises a heterocyclic compound represented by Formula 2.
[0007]
[0008] In Formula 1, R1 and R2 are independently selected from any one of hydrogen, deuterium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C12 alicyclic ring and a C2-C30 heteroaromatic ring, or any one of R1 and R2 is directly bonded to L3;
[0009] W is independently selected from C(R0) or N;
[0010] R0 is independently selected from any one of hydrogen, deuterium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group; or adjacent two R0 are connected to form a substituted or unsubstituted ring;
[0011] L1, L2, and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;
[0012] Ar1 and Ar2 are independently selected from any one of the following groups:
[0013]
[0014] X is independently selected from C(R6) or N, and X bonded to L1 and L2 is selected from a C atom;
[0015] Y1is selected from O or N(R 10 )Y2is selected from O, S or N(R 11 )Y3is selected from O, S or N(R
[0016] R3is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl group;
[0017] R4, R5are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl;
[0018] R6, R7are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C2-C12alkenyl, substituted or unsubstituted C1-C12alkoxy, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or two adjacent R6are linked to form a substituted or unsubstituted ring;
[0019] m1is selected from 1 or 2;
[0020] R 10 , R 11 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl;
[0021]
[0022] Q is independently selected from C(Rd) or N; Q bonded with La is selected from C atom;
[0023] Z0is selected from O, S or N(Re);
[0024] La is independently selected from any one of single bond, substituted or unsubstituted C6-C30arylene, substituted or unsubstituted C2-C30heteroarylene;
[0025] n is selected from 1, 2, 3 or 4; when there are two or more La, the two or more La are the same or different from each other;
[0026] Ra, Rd, Reare independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or two adjacent Rdare linked to form a substituted or unsubstituted ring;
[0027] A is selected from Formula 2-1 or Formula 2-2,
[0028]
[0029] V is independently selected from C(Rf) or N atom, V bonded with La is selected from C atom;
[0030] Z1is selected from O, S, C(RgRh), or N(Ri);
[0031] Rb, Rc, Rg, Rhare independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or Rband Rcare linked to form a substituted or unsubstituted ring; or Rgand Rhare linked to form a substituted or unsubstituted ring;
[0032] Rfis independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or two adjacent Rfare linked to form a substituted or unsubstituted ring;
[0033] Riis independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl.
[0034] Advantageous effects
[0035] The organic electroluminescent device provided by the present application, the hole transport region comprises a structure of formula 1, and the electron transport region comprises a structure of formula 2, which can effectively block the diffusion of the electrons and holes transferred to the light-emitting layer to the hole / electron transport layer, significantly improve the probability of the holes and the electrons in the light-emitting layer to combine into excitons, limit the combination region of the holes and the electrons in the light-emitting layer, greatly improve the light-emitting efficiency of the organic electroluminescent device, and avoid the leakage of the electrons and the holes to the electron transport layer and the hole transport layer to cause the aging of the device, thereby prolonging the service life of the organic electroluminescent device. DETAILED DESCRIPTION
[0036] The technical solutions of the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. After reading the present application, those skilled in the art can make various modifications to the equivalent forms of the present application, which all fall within the scope defined by the present application.
[0037] In the compounds of the present application, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.
[0038] In the specification, “*-” refers to a moiety connected to another substituent. “*-” can be connected to any optional position of the connected group / fragment. For example, represents By analogy.
[0039] In the present application, when the position of a substituent on an aromatic ring is not fixed, it means that it can be connected to any one of the corresponding optional positions of the aromatic ring. For example, may represent may represent may represent By analogy.
[0040] The halogen described in the present application can include fluorine, chlorine, bromine and iodine.
[0041] The alkyl described in the present application refers to a monovalent group after removing one hydrogen atom from an alkane molecule, which can be a straight-chain alkyl group or a branched-chain alkyl group, preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, and particularly preferably has 1 to 6 carbon atoms. Examples can include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, etc., but are not limited thereto.
[0042] The alkenyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from an alkene molecule, which can be a straight-chain alkenyl group or a branched-chain alkenyl group, preferably has 2 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples can include ethenyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, phenystyryl, methylphenystyryl, 3-phenylpropenyl, 2-phenyl-1-propenyl, and the like, but are not limited thereto.
[0043] The cycloalkyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, which preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Examples can include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, and the like, but are not limited thereto.
[0044] The aryl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from an aromatic carbon of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, preferably has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples can include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthenyl, triphenylenyl, 1,2-benzophenanthryl, 2,3-benzophenanthryl, 3,4-benzophenanthryl, perylenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, benzofluorenyl, and the like, but are not limited thereto.
[0045] The heteroaryl group according to the present application refers to a monovalent group obtained by replacing one or more aromatic ring carbon atoms in an aromatic hydrocarbon molecule with a heteroatom, including but not limited to oxygen, sulfur, selenium, nitrogen, silicon, or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, most preferably 2 to 12 carbon atoms. Examples can include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidyl, phenylpyridyl, phenylpyrimidyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolyl, quinoxalyl, benzoquinazolyl, benzoquinoxalyl, phenanthrolinyl, naphthrydinyl, indolyl, benzothienyl, benzofuranyl, N-heterobenzothienyl, N-heterobenzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxadiazolyl, benzothiadiazolyl, benzotriazolyl, dibenzofuranyl, N-heterodibenzofuranyl, benzo-dibenzofuranyl, dibenzothienyl, N-heterodibenzothienyl, benzo-dibenzothienyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, N-heterocarbazolyl, benzo-carbazolyl, indeno-carbazolyl, indolo-carbazolyl, benzofurano-carbazolyl, benzothieno-carbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, spirofluoreno-xanthenyl, spirofluoreno-thioxanthenyl, and the like, but are not limited thereto.
[0046] The silyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a silane molecule, which can be represented by — Si(Rs)(Rs)(Rs), wherein Rs is selected from hydrogen, deuterium, cyano, halogen, or any one or more selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl as described above, preferably having 1 to 30 carbon atoms, preferably having 1 to 25 carbon atoms, more preferably having 1 to 22 carbon atoms, most preferably 1 to 18 carbon atoms, examples can include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethyl-t-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylenylsilyl, and the like, but are not limited thereto.
[0047] The fused ring group of the alicyclic and aromatic ring according to the present application means a monovalent group in which an alicyclic ring and an aromatic ring are fused together and one hydrogen atom is lost. The number of carbon atoms of the alicyclic ring is C3 to C15, preferably C3 to C12, and more preferably C3 to C8. The number of carbon atoms of the aromatic ring is C6 to C30, preferably C6 to C18, and more preferably C6 to C15. Examples of the fused ring group of the C3 to C12 alicyclic ring and C6 to C30 aromatic ring include, but are not limited to, groups such as benzcyclopropane group, benzcyclobutane group, benzcyclopentane group, indene group, benzcyclohexane group, benzcycloheptane group, benzcyclobutene group, benzcyclopentene group, benzcyclohexene group, acenaphthene group, naphthocyclohexane group, and the like.
[0048] The fused ring group of the alicyclic and aromatic ring according to the present application means a monovalent group in which an alicyclic ring and an aromatic ring are fused together and one hydrogen atom is lost. The number of carbon atoms of the alicyclic ring is C3 to C15, preferably C3 to C12, and more preferably C3 to C8. The number of carbon atoms of the aromatic ring is C6 to C30, preferably C6 to C18, and more preferably C6 to C15. Examples of the fused ring group of the C3 to C12 alicyclic ring and C6 to C30 aromatic ring include, but are not limited to, groups such as benzcyclopropane group, benzcyclobutane group, benzcyclopentane group, indene group, benzcyclohexane group, benzcycloheptane group, benzcyclobutene group, benzcyclopentene group, benzcyclohexene group, acenaphthene group, naphthocyclohexane group, and the like.
[0049] The arylene group according to the present application means a divalent group in which two binding sites are present on an aromatic group. They can be applied to the above-mentioned description of the aromatic group except that they are divalent groups, respectively.
[0050] The heteroarylene group according to the present application means a divalent group in which two binding sites are present on a heteroaromatic group. They can be applied to the above-mentioned description of the heteroaromatic group except that they are divalent groups, respectively.
[0051] The "substituted" of the present application, such as "substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted silyl, substituted aryl, substituted heteroaryl, substituted fused ring group of C3 to C12 alicyclic and C6 to C30 aromatic ring, substituted fused ring group of C3 to C12 alicyclic and C2 to C30 heteroaromatic ring, substituted arylene, substituted heteroarylene" means independently mono- or poly-substituted with deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C2 to C12 alkenyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C1 to C12 alkylthio, substituted or unsubstituted C1 to C12 alkylamino, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C6 to C30 arylamino, and the like, but not limited thereto, and when two or more substituents are present, two adjacent substituents can be linked to form a ring. Preferably, mono- or poly-substituted with deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclopentadiene, cyclohexadiene, adamantane, norbornane, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, anthryl, phenanthryl, triphenylene, perylene, pyrene, benzyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, tert-butyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, diphenylamino, pyridyl, pyrimidyl, triazinyl, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl, and the like, but not limited thereto.
[0052] In the present invention, "connected to form a ring between adjacent groups" means that the adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocyclic ring. The "adjacent groups" means two substituents on two atoms directly connected, substituents disposed to be spatially closest to the corresponding substituents, another substituent on an atom having the corresponding substituent, for example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an alicyclic ring can be considered to be "adjacent" to each other; as exemplified below:
[0053]
[0054] In the present invention, the ring formed by the connection can be a five-membered ring or a six-membered ring or a fused ring, for example, benzene, naphthalene, cyclopentane, cyclohexane, cyclopentene, cyclohexene, tetrahydronaphthalene, dihydroindene, dihydronaphthalene, indene, phenanthrene, triphenylene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, but not limited thereto.
[0055] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region being between the anode and the light-emitting layer, the electron transport region being between the light-emitting layer and the cathode, the hole transport region comprising a triarylamine compound represented by Formula 1, and the electron transport region comprising a heterocyclic compound represented by Formula 2,
[0056]
[0057] In Formula 1, R1, R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, a fused ring group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaromatic ring; or any one of R1, R2 is directly bonded to L3;
[0058] W is independently selected from C(R0) or N;
[0059] R0is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or adjacent two R0are linked to form a substituted or unsubstituted ring;
[0060] L1, L2, L3are independently selected from any one of single bond, substituted or unsubstituted C6-C30arylene, substituted or unsubstituted C2-C30heteroarylene;
[0061] Ar1, Ar2are independently selected from any one of the following groups:
[0062]
[0063] X is independently selected from C(R6) or N, X bonded with L1, L2is selected from C atom;
[0064] Y1is selected from O or N(R6); Y2is selected from O, S or N(R6); 10 11
[0065] R3is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl;
[0066] R4, R5are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl;
[0067] R6, R7are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C2-C12alkenyl, substituted or unsubstituted C1-C12alkoxy, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or adjacent two R6are linked to form a substituted or unsubstituted ring;
[0068] m1is selected from 1 or 2;
[0069] R 10 , R 11 independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0070]
[0071] Q is independently selected from C(Rd) or N; Q bonded with La is selected from C atom;
[0072] Z0is selected from O, S or N(Re);
[0073] La is independently selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene;
[0074] n is selected from 1, 2, 3 or 4; when there are two or more La, the two or more La are the same or different from each other;
[0075] Ra, Rd, Re are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rd are connected to form a substituted or unsubstituted ring;
[0076] A is selected from formula 2-1 or formula 2-2,
[0077]
[0078] V is independently selected from C(Rf) or N atom, V bonded with La is selected from C atom;
[0079] Z1is selected from O, S, C(RgRh) or N(Ri);
[0080] Rb, Rc, Rg, Rh are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or Rb and Rc are connected to form a substituted or unsubstituted ring; or Rg and Rh are connected to form a substituted or unsubstituted ring;
[0081] Rf is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rf are linked to form a substituted or unsubstituted ring;
[0082] Ri is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl.
[0083] Preferably, the hole transport region comprises at least one of a hole injection layer and a hole transport layer; at least one of the hole injection layer and the hole transport layer comprises the triarylamine compound represented by Formula 1; the electron transport region comprises at least one of a hole blocking layer and an electron transport layer, and at least one of the hole blocking layer and the electron transport layer comprises the heterocyclic compound represented by Formula 2.
[0084] More preferably, the hole transport region comprises a hole transport layer, and the hole transport layer comprises the triarylamine compound represented by Formula 1; the electron transport region comprises a hole blocking layer, and the hole blocking layer comprises the heterocyclic compound represented by Formula 2.
[0085] Further preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprises the triarylamine compound represented by Formula 1.
[0086] Preferably, the thickness of the hole transport layer is 30 nm to 200 nm.
[0087] Preferably, the thickness of the first hole transport layer is 30 nm to 200 nm, and the thickness of the second hole transport layer is 3 nm to 100 nm.
[0088] Preferably, the thickness of the first hole transport layer is 60 nm to 180 nm.
[0089] Further preferably, the thickness of the first hole transport layer is 80 nm to 140 nm.
[0090] More preferably, the thickness of the first hole transport layer is 100 nm to 120 nm.
[0091] Preferably, the thickness of the second hole transport layer is 5 nm to 90 nm.
[0092] Further preferably, the thickness of the second hole transport layer is 40 nm to 80 nm (red light); the thickness of the second hole transport layer is 20 nm to 60 nm (green light); the thickness of the second hole transport layer is 5 nm to 30 nm (blue light).
[0093] More preferably, the thickness of the second hole transport layer is 40 nm to 70 nm (red light); the thickness of the second hole transport layer is 30 nm to 50 nm (green light); the thickness of the second hole transport layer is 5 nm to 25 nm (blue light).
[0094] Preferably, the thickness of the third hole transport layer is 5 nm to 150 nm.
[0095] More preferably, the thickness of the third hole transport layer is 10 nm to 100 nm.
[0096] Preferably, the compound of Formula 1 is selected from Formula 1-1 or Formula 1-2:
[0097]
[0098] In Formula 1-1, Formula 1-2,
[0099] R1', R2' are independently selected from hydrogen, deuterium, cyano, halogen, nitro, any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, ethenyl, propenyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutene, benzocyclopentene, benzocyclohexene, naphthyl, anthryl, phenanthryl, triphenylene, pyrene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl 9-phenylfluorenyl, 9,9'-spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, indenyl, indolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, carbazolyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
[0100] The "substituted" group is selected from any one of deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0101] The definitions of W, L1-L3, Ar1, Ar2 are the same as those in Formula 1.
[0102] More preferably, R1', R2' are independently selected from any one of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated iso-propyl, deuterated n-butyl, deuterated iso-butyl, deuterated sec-butyl, deuterated tert-butyl, trifluoromethyl, cyclopropanyl, cyclobutanyl, cyclopentanoyl, cyclohexanoyl, cycloheptanoyl, adamantoyl, norbornanoyl, trimethylsilyl, triethylsilyl, triphenylsilyl, or the following groups:
[0103]
[0104] m2 is independently selected from 1, 2, 3, 4, or 5, and m3 is independently selected from 1, 2, 3, 4, 5, 6, or 7.
[0105] Preferably, R1' is independently selected from any one of the following groups:
[0106]
[0107] Preferably, Ar1, Ar2 are independently selected from any one of the following groups:
[0108]
[0109]
[0110]
[0111]
[0112] R6, R7 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl;
[0113] R 12 , R 12independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0114] said R 10 , R 11 independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl;
[0115] said a1 is independently selected from 1, 2, 3, 4 or 5, said a2 is independently selected from 1, 2, 3 or 4, said a3 is independently selected from 1, 2 or 3, said a4 is independently selected from 1 or 2, said a5 is independently selected from 1, 2, 3, 4, 5 or 6, said a6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, and said a8 is independently selected from 1, 2, 3, 4, 5, 6 or 7.
[0116] More preferably, said Ar1 is selected from any one of the following groups:
[0117]
[0118]
[0119] said R6, R7, R 10 , R 11 , R 12 , R6', a1-a6, a8 are defined as above.
[0120] Preferably, said L1, L2, L3 are independently selected from a single bond or any one of the following groups:
[0121]
[0122] said R 13 , R 13 independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl;
[0123] said Y3 is selected from O, S or C(R 14 R 15 );
[0124] said R 14 , R15 independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0125] said b1 is independently selected from 1, 2, 3, or 4, said b2 is independently selected from 1 or 2, said b3 is independently selected from 1, 2, 3, 4, 5, or 6, said b4 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8, and said b5 is independently selected from 1, 2, or 3.
[0126] Preferably, said is selected from any one of the following groups:
[0127] said Z0 is selected from O, S, or N(Re);
[0128] independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0129] independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0130] independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0131] said q1 is independently selected from 1, 2, 3, or 4, said q2 is independently selected from 1, 2, or 3, said q3 is independently selected from 1 or 2, said q4 is independently selected from 1, 2, 3, 4, 5, or 6, said q5 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8, said q6 is independently selected from 1, 2, 3, 4, 5, 6, or 7, and said q7 is independently selected from 1, 2, 3, 4, or 5.
[0132] More preferably, said Ra is independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, trimethylsilyl, triethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl.
[0133] Preferably, said A is independently selected from the group consisting of any one of the following groups:
[0134]
[0135]
[0136] said Rb', Rc' is independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, adamantane, norbornane, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentene, benzocyclohexene, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, benzofuranyl, benzothiophenyl, indenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-spiro-bifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
[0137] said Rf, Rf' is independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, quinolyl, isoquinolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
[0138] said Z1is independently selected from O, S, C(RgRh), or N(Ri);
[0139] said Rg, Rh, Ri are independently selected from hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexananyl, adamantanyl, norbornanyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
[0140] said pi is independently selected from 1, 2, 3, 4, 5, 6, or 7, said p2 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9, said p3 is independently selected from 1, 2, or 3, said p4 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8, said p5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, said p6 is independently selected from 1, 2, 3, 4, 5, or 6, said p7 is independently selected from 1, 2, 3, 4, or 5, said p8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, said p9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, said p 10 is independently selected from 1, 2, 3, or 4, said p 11 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.
[0141] Preferably, said Ra’, Rb’ are independently selected from any one of the following groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated i-propyl, deuterated n-butyl, deuterated t-butyl, cyclopentananyl, cyclohexananyl, adamantanyl, norbornanyl, trimethylsilyl, triethylsilyl, triphenylsilyl; or from any one of the following groups:
[0142]
[0143] Rw, Rw' are independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups substituted or non-substituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, quinolyl, isoquinolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
[0144] g1 is independently selected from 1, 2, 3, 4 or 5, g2 is independently selected from 1, 2, 3 or 4, g3 is independently selected from 1, 2, 3, 4, 5, 6 or 7, g4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9, g5 is independently selected from 1, 2 or 3, g6 is independently selected from 1, 2, 3, 4, 5 or 6, g7 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8.
[0145] More preferably, Rb' is independently selected from any one of the following groups:
[0146]
[0147]
[0148] m2 is independently selected from 1, 2, 3, 4 or 5, m3 is independently selected from 1, 2, 3 or 4.
[0149] Preferably, La is selected from a single bond or any one of the following groups:
[0150]
[0151] E is independently selected from C(Rj) or N;
[0152] Rj is independently selected from any one of the following groups: hydrogen, deuterium, cyano, halogen, nitro, substituted or non-substituted C1-C12 alkyl, substituted or non-substituted C3-C12 cycloalkyl, substituted or non-substituted silyl, substituted or non-substituted C6-C30 aryl, substituted or non-substituted C2-C30 heteroaryl;
[0153] Z2 is selected from O, S or C(RkRl), Z3 is selected from O, S, C(RmRn) or N(Rp);
[0154] The Rk, Rl, Rm, Rn, and Rp are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or adjacent Rk and Rl are connected to form a substituted or unsubstituted ring.
[0155] More preferably, the "*-(La)n-*" is selected from any one of the following groups:
[0156]
[0157]
[0158] Rj and Rj' are independently selected from any one of the following groups, which are hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl;
[0159] The c1 is independently selected from 1, 2, 3, or 4; the c2 is independently selected from 1, 2, or 3; the c3 is independently selected from 1 or 2; the c4 is independently selected from 1, 2, 3, 4, 5, or 6; the c5 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8; the c6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and the c7 is independently selected from 1, 2, 3, 4, or 5.
[0160] Most preferably, the triarylamine compound represented by Formula 1 is selected from any one of the following structures:
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181]
[0182] Most preferably, the heterocyclic compound of Formula 2 is selected from any one of the following structures:
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213] The above lists some specific structural forms of the compound of formula 1 and the compound of formula 2 according to the present application, but the present application is not limited to the listed chemical structures, and any structure based on the structures of formula 1 and formula 2 and having substituents as defined above should be included.
[0214] The material of each layer thin film in the organic electroluminescent device according to the present application is not particularly limited, and any material known in the art can be used. The following describes each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device, respectively:
[0215] As the anode of the present application, a transmissive electrode, a reflective electrode or a semi-transmissive electrode can be selected, and when the anode is a transmissive electrode, the anode material can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof; and when the anode is a semi-transmissive electrode or a reflective electrode, the anode material can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof.
[0216] As the hole injection layer of the present application, in addition to the compound of Formula 1 provided by the present application, a material having good hole-accepting ability is preferred. Metalloporphyrin, oligothiophene, arylamine, hexacyno hexaazatriphenylene, quinacridone, perylene material, etc. can be selected, and specific examples can include 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), copper phthalocyanine (CuPC), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyano dimethyl p-benzoquinone (F4-TCNQ), etc., but are not limited thereto.
[0217] As the hole transport layer of the present application, in addition to the compound of Formula 1 provided by the present application, a material having high hole mobility is also preferred. Diphenylamine compounds, fluorene compounds and carbazole compounds, biphenyldiamine compounds, etc. can be selected, and specific examples can include N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl) aniline] (TAPC), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc., but are not limited thereto.
[0218] As the light emitting layer material of the present application, red, green or blue light emitting materials, generally containing guest (dopant) materials and host materials, can be used. The guest materials can be simple fluorescent materials or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. The host materials of the light emitting layer not only need to have bipolar charge transport properties, but also need to have appropriate energy levels to effectively transfer excitation energy to the guest light emitting materials. Such materials can be selected from diphenylstyryl aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives, and specific examples can include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9,9'-(2,6-pyridinediylbis-3,1-phenylene)bis-9H-carbazole (26DCZPPY), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazolyl)benzene (MCP), 9,10-bis(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (TBADN), etc., but are not limited thereto.
[0219] The guest materials can be selected from metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., and specific examples can include bis(2-(naphthalen-2-yl)pyridine)(acetylacetonate)iridium (Ir(npy)2acac), bis(2-phenylpyridine)iridium di(acetylacetonate) (Ir(ppy)2(acac)), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetonate)iridium (Ir(bzq)2(acac)), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 1,4-bis(4-(9H-carbazol-9-yl)styryl)benzene (BCzSB), etc., but are not limited thereto.
[0220] As the electron transport layer material of the present application, in addition to the compound of formula 2 provided by the present application, materials having high electron mobility are preferred. Specific examples can include quinoline-based, imidazole-based, phenanthroline-based, triazole-based, metal chelates, azabenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano-based, benzimidazole-based, etc., but are not limited thereto.
[0221] As the hole blocking layer material of the present application, in addition to the compound of formula 2 provided by the present application, a material having a good electron transport ability and a hole blocking ability can be selected from metal complexes, quinoline derivatives, imidazole derivatives, phenanthroline derivatives, triazole derivatives, azabenzene derivatives, etc., and specific examples can include bis(2-methyl-8-hydroxyquinoline-N1, O8)-(1,1'-biphenyl-4-hydroxy) aluminum (BAlq), 1,3,5-tris(N-phenyl-2-benzimidazole) benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]dipyridine (TmPyPB), etc., but are not limited thereto.
[0222] As the electron injection layer material of the present application, a material having a low work function is preferred. Specific examples can include metals, alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, alkali metal salts, alkaline earth metal salts, metal complexes, etc. Examples can include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline) aluminum, etc., but are not limited thereto.
[0223] As the cathode of the present application, a transmissive electrode, a semi-reflective electrode, or a reflective electrode can be selected. When the cathode is a transmissive electrode, the cathode material can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the cathode material can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including the same, or mixtures thereof (e.g., a mixture of Ag and Mg), but are not limited thereto.
[0224] The organic layer of the organic electroluminescent device described above can be deposited by a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, etc., and when a vacuum deposition method is used, the conditions for vacuum deposition can vary depending on the compound.
[0225] The organic electroluminescent device of the present application is mainly applied to the field of information display technology and the field of lighting, and is widely used in various information displays in the field of information display, such as mobile phones, tablet computers, flat panel televisions, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices, etc.
[0226] The production of the above-mentioned organic electroluminescent device is specifically described in the following examples. However, the following examples are only used for illustrating the present specification, and the scope of the present specification is not limited to the examples.
[0227] Meanwhile, the present application also provides a preparation method of the compound of formula 1 and the compound of formula 2, and the specific synthesis route is shown as follows, but is not limited thereto:
[0228] [Synthesis route of compound of formula 1]
[0229]
[0230] The Xa, Xb are independently selected from any one of Cl, Br and I.
[0231] [Synthesis route of compound of formula 2]
[0232]
[0233] The Xc, Xd, Xe, Xf are independently selected from any one of Cl, Br and I.
[0234] Explanation of raw materials, reagents and characterization equipment:
[0235] The raw materials used in the following examples of the present application are not particularly limited, and can be commercially available products or prepared by using the preparation method known to those skilled in the art.
[0236] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the United Kingdom, and chloroform is used as the solvent.
[0237] Elemental analysis uses a Vario EL cube organic elemental analyzer of Elementar Company in Germany, and the sample mass is 5-10 mg.
[0238] Synthesis Example 1: Preparation of compound 1-84
[0239]
[0240] Preparation of intermediate A84:
[0241] To a reaction flask, under nitrogen protection, were added a84 (30.57 g, 60 mmol), b84 (12.56 g, 60 mmol), sodium tert-butoxide (11.53 g, 120 mmol), Pd(PPh3)4(0.69 g, 0.60 mmol) successively, dissolved by adding 500 mL of toluene, heated to reflux for 6 hours. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, the organic phase was washed with distilled water three times, allowed to stand and separate, the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by distillation under reduced pressure, crystallized by cooling, filtered, the obtained solid was recrystallized with ethyl acetate to obtain intermediate A84 (32.53 g, yield 85%), the solid purity was detected by HPLC to be ≧99.89%. Mass spectrum m / z: 637.3701 (theoretical value: 637.3709).
[0242] Preparation of compound 1-84:
[0243] To a reaction flask, under nitrogen protection, were added intermediate A84 (19.14 g, 30 mmol), c84 (4.71 g, 30 mmol), Pd2(dba)3(0.27 g, 0.30 mmol), X-phos (0.29 g, 0.60 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) successively, 300 mL of toluene was added, stirred and dissolved, heated to reflux for 8 hours, after the reaction was completed, it was cooled to room temperature, filtered, the filter cake was washed with a small amount of toluene, the obtained solid was recrystallized with toluene to obtain compound 1-84 (17.14 g, yield 80%), the solid purity was detected by HPLC to be ≧99.97%. Mass spectrum m / z: 713.4011 (theoretical value: 713.4022). Theoretical elemental content (%) 54 H 51 N: C, 90.84; H, 7.20; N, 1.96. Found elemental content (%): C, 90.82; H, 7.23; N, 1.95.
[0244] Synthesis example 2: Preparation of compound 1-138
[0245]
[0246] According to the preparation method of synthesis example 1, equimolar a84 was replaced by equimolar a138 to obtain compound 1-138 (17.02 g, 82%), the HPLC purity was ≧99.96%. Mass spectrum m / z: 691.3223 (theoretical value: 691.3239). Theoretical elemental content (%) 53 H 41 N: C, 92.00; H, 5.97; N, 2.02. Found elemental content (%): C, 92.03; H, 5.91; N, 2.05.
[0247] Synthesis Example 3: Preparation of compound 1-159
[0248]
[0249] According to the preparation method of synthesis example 1, replace equal moles of a84, c84 with equal moles of a159, c159 respectively, to obtain compound 1-159 (17.72 g, 86%), HPLC purity ≧ 99.94%. Mass spectrum m / z: 686.3658 (theoretical value: 686.3647). Theoretical elemental content (%) C 52 H 30 D9N: C, 90.92; H, 7.04; N, 2.04. Measured elemental content (%) : C, 90.93; H, 7.05; N, 2.02.
[0250] Synthesis Example 4: Preparation of compound 1-171
[0251]
[0252] According to the preparation method of synthesis example 1, replace equal moles of a84, c84 with equal moles of a171, c171 respectively, to obtain compound 1-171 (17.44 g, 84%), HPLC purity ≧ 99.93%. Mass spectrum m / z: 691.3232 (theoretical value: 691.3239). Theoretical elemental content (%) C 53 H 41 N: C, 92.00; H, 5.97; N, 2.02. Measured elemental content (%) : C, 92.04; H, 5.92; N, 2.03.
[0253] Synthesis Example 5: Preparation of compound 1-189
[0254]
[0255] According to the preparation method of synthesis example 1, replace equal moles of a84, c84 with equal moles of a189, c189 respectively, to obtain compound 1-189 (18.72 g, 85%), HPLC purity ≧ 99.95%. Mass spectrum m / z: 733.3718 (theoretical value: 733.3709). Theoretical elemental content (%) C 56 H 47 N: C, 91.64; H, 6.45; N, 1.91. Measured elemental content (%) : C, 91.63; H, 6.44; N, 1.93.
[0256] Synthesis Example 6: Preparation of compound 1-214
[0257]
[0258] According to the preparation method of synthetic example 1, replace equal moles of a84, c84 with equal moles of a214, c171 respectively, to obtain compound 1-214 (18.10 g, 80%), HPLC purity≧99.92%. Mass spectrum m / z: 753.3384 (theoretical value: 753.3396). Theoretical elemental content (%) C 58 H 43 N: C, 92.39; H, 5.75; N, 1.86. Actual elemental content (%) : C, 92.34; H, 5.78; N, 1.88.
[0259] Synthetic example 7: preparation of compound 1-269
[0260]
[0261] According to the preparation method of synthetic example 1, replace equal moles of a84, b84, c84 with equal moles of a171, b269, c269 respectively, to obtain compound 1-269 (19.12 g, 83%), HPLC purity≧99.94%. Mass spectrum m / z: 767.3563 (theoretical value: 767.3552). Theoretical elemental content (%) C 59 H 45 N: C, 92.27; H, 5.91; N, 1.82. Actual elemental content (%) : C, 92.24; H, 5.93; N, 1.83.
[0262] Synthetic example 8: preparation of compound 1-283
[0263]
[0264] According to the preparation method of synthetic example 1, replace equal moles of a84, c84 with equal moles of a283, c283 respectively, to obtain compound 1-283 (17.13 g, 84%), HPLC purity≧99.93%. Mass spectrum m / z: 679.3221 (theoretical value: 679.3239). Theoretical elemental content (%) C 52 H 41 N: C, 91.86; H, 6.08; N, 2.06. Actual elemental content (%) : C, 91.83; H, 6.09; N, 2.08.
[0265] Synthetic example 9: preparation of compound 1-339
[0266]
[0267] Following the procedure of the preparation of synthesis example 1, replacing a84, b84, c84 with a159, b596, c596, respectively, in equal molar amounts, compound 1-596 (15.78 g, 82%) was obtained with HPLC purity > 99.95%. Mass spectrum m / z: 657.3005 (calcd 657.3013). Theoretical elemental content (%) C 54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Found elemental content (%) : C, 90.37; H, 5.47; N, 1.93.
[0268] Synthesis Example 10: Preparation of compound 1-397
[0269]
[0270] Following the procedure of the preparation of synthesis example 1, replacing a84, b84, c84 with a397, b269, c397, respectively, in equal molar amounts, compound 1-397 (17.02 g, 82%) was obtained with HPLC purity > 99.95%. Mass spectrum m / z: 691.3227 (calcd 691.3239). Theoretical elemental content (%) C 53 H 41 N: C, 92.00; H, 5.97; N, 2.02. Found elemental content (%) : C, 92.07; H, 5.91; N, 2.01.
[0271] Synthesis Example 11: Preparation of compound 1-505
[0272]
[0273] Following the procedure of the preparation of synthesis example 1, replacing a84, b84, c84 with a159, b505, c505, respectively, in equal molar amounts, compound 1-505 (15.78 g, 83%) was obtained with HPLC purity > 99.96%. Mass spectrum m / z: 633.2863 (calcd 633.2852). Theoretical elemental content (%) C 46 H 39 NSi: C, 87.16; H, 6.20; N, 2.21. Found elemental content (%) : C, 87.12; H, 6.22; N, 2.23.
[0274] Synthesis Example 12: Preparation of compound 1-596
[0275]
[0276] According to the preparation method of synthesis example 1, replace equal moles of a84 with equal moles of a596 to obtain compound 1-596 (17.08 g, 84%), HPLC purity ≧ 99.94%. Mass spectrum m / z: 677.3071 (theoretical value: 677.3083). Theoretical elemental content (%) C 52 H 39 N: C, 92.13; H, 5.80; N, 2.07. Actual elemental content (%) C, 92.15; H, 5.84; N, 2.01.
[0277] Synthesis Example 13: Preparation of compound 1-611
[0278]
[0279] According to the preparation method of synthesis example 1, replace equal moles of a84, b84, c84 with equal moles of a159, b611, c171 to obtain compound 1-611 (19.23 g, 85%), HPLC purity ≧ 99.97%. Mass spectrum m / z: 753.3381 (theoretical value: 753.3396). Theoretical elemental content (%) C 58 H 43 N: C, 92.39; H, 5.75; N, 1.86. Actual elemental content (%) C, 92.37; H, 5.74; N, 1.89.
[0280] Synthesis Example 14: Preparation of compound 2-15
[0281]
[0282] Preparation of intermediate A-2-15: Under nitrogen protection, a-2-15 (49.39 g, 150.00 mmol), bis(pinacolato)diboron (38.09 g, 150.00 mmol), K2CO3(41.46 g, 300.00 mmol), Pd(PPh3)4(1.73 g, 1.5 mmol), 900 mL dimethylformamide were added to a reaction bottle, the reaction was stirred under reflux condition for 6 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added thereto, then extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, then recrystallized with toluene / ethanol=10:3 to obtain intermediate A-2-15 (43.47 g, yield 77%), HPLC purity ≧ 99.86%. Mass spectrum m / z: 376.2588 (theoretical value: 376.2574).
[0283] Preparation of Intermediate B-2-15: To a reaction flask was added A-2-15 (37.63 g, 100.00 mmol), b-2-15 (26.76 g, 100.00 mmol), K2CO3 (20.73 g, 150.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), 750 mL of toluene / ethanol / water (3:1:1) under nitrogen protection, the reaction was stirred under reflux condition for 5 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, suction filtration was performed, rinsed with ethanol, then the obtained solid was recrystallized with toluene to obtain Intermediate B-2-15 (34.52 g, yield 79%), HPLC purity ≧ 99.88%. Mass spectrum m / z: 436.1969 (theoretical value: 436.1958).
[0284] Preparation of Intermediate C-2-15: To a reaction flask was added B-2-15 (28.41 g, 65.00 mmol), bis(pinacolato)diboron (16.51 g, 65.00 mmol), KOAc (10.80 g, 110.00 mmol), Pd(dppf)Cl2 (0.48 g, 0.65 mmol), 600 mL of 1,4-dioxane under nitrogen protection, the reaction was stirred under reflux condition for 4.5 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto, then extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, rotary evaporation was performed to remove the solvent, then recrystallized with toluene to obtain Intermediate C-2-15 (27.83 g, yield 81%), HPLC purity ≧ 99.90%. Mass spectrum m / z: 528.3211 (theoretical value: 528.3200).
[0285] Preparation of Compound 2-15: To a reaction flask was added C-2-15 (18.50 g, 35.00 mmol), c-2-15 (6.93 g, 35.00 mmol), K2CO3 (8.29 g, 60.00 mmol), Pd2(dba)3 (0.32 g, 0.35 mmol), tri-tert-butylphosphine (1.4 mL of 0.50 M toluene solution, 0.70 mmol), 250 mL of tetrahydrofuran under nitrogen protection, the reaction was stirred under reflux condition for 5 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, suction filtration was performed to obtain a filter cake, rinsed with a small amount of toluene, then the obtained filter cake was recrystallized with toluene to obtain Compound 2-15 (14.37 g, yield 79%), HPLC purity ≧ 99.95%. Mass spectrum m / z: 519.2574 (theoretical value: 519.2562). Theoretical elemental content (%) 38 H 33C, 87.83; H, 6.40; N, 2.70. Actual elemental content (%) found: C, 87.85; H, 6.38; N, 2.70.
[0286] Synthesis Example 15: Preparation of compound 2-86
[0287]
[0288] According to the preparation method of Synthesis Example 14, replace the equal moles of a-2-15 with equal moles of a-2-86 and the equal moles of b-2-15 with equal moles of b-2-86 to obtain compound 2-86 (15.25 g) with HPLC purity ≧ 99.91%. Mass spectrum m / z: 588.2211 (theoretical value: 588.2202). Theoretical elemental content (%) C 43 H 28 N2O: C, 87.73; H, 4.79; N, 4.76. Actual elemental content (%) found: C, 87.76; H, 4.75; N, 4.77.
[0289] Synthesis Example 16: Preparation of compound 2-214
[0290]
[0291] According to the preparation method of Synthesis Example 14, replace the equal moles of a-2-15 with equal moles of a-2-214 to obtain compound 2-214 (16.49 g) with HPLC purity ≧ 99.94%. Mass spectrum m / z: 612.2212 (theoretical value: 612.2202). Theoretical elemental content (%) C 45 H 28 N2O: C, 88.21; H, 4.61; N, 4.57. Actual elemental content (%) found: C, 88.25; H, 4.57; N, 4.59.
[0292] Synthesis Example 17: Preparation of compound 2-263
[0293]
[0294] According to the preparation method of Synthesis Example 14, replace the equal moles of a-2-15 with equal moles of a-2-263 to obtain compound 2-263 (15.80 g) with HPLC purity ≧ 99.97%. Mass spectrum m / z: 601.2420 (theoretical value: 601.2406). Theoretical elemental content (%) C 45 H 31 NO: C, 89.82; H, 5.19; N, 2.33. Actual elemental content (%) found: C, 89.80; H, 5.20; N, 2.31.
[0295] Synthesis Example 18: Preparation of compound 2-281
[0296]
[0297] According to the preparation method of Synthesis Example 14, replace equal moles of a-2-15 with equal moles of a-2-281 to obtain compound 2-281 (15.95 g) with HPLC purity ≧ 99.95%. Mass spectrum m / z: 615.2577 (theoretical value: 615.2562). Theoretical elemental content (%) C 46 H 33 NO: C, 89.73; H, 5.40; N, 2.27. Measured elemental content (%) : C, 89.76; H, 5.42; N, 2.24.
[0298] Synthesis Example 19: Preparation of compound 2-292
[0299]
[0300] According to the preparation method of Synthesis Example 14, replace equal moles of a-2-15 with equal moles of a-2-292 to obtain compound 2-292 (17.12 g) with HPLC purity ≧ 99.98%. Mass spectrum m / z: 643.2865 (theoretical value: 643.2875). Theoretical elemental content (%) C 48 H 37 NO: C, 89.55; H, 5.79; N, 2.18. Measured elemental content (%) : C, 89.57; H, 5.82; N, 2.17.
[0301] Synthesis Example 20: Preparation of compound 2-307
[0302]
[0303] According to the preparation method of Synthesis Example 14, replace equal moles of a-2-15 with equal moles of a-2-307 to obtain compound 2-307 (16.86 g) with HPLC purity ≧ 99.93%. Mass spectrum m / z: 659.2633 (theoretical value: 659.2644). Theoretical elemental content (%) C 47 H 37 NOSi: C, 85.55; H, 5.65; N, 2.12. Measured elemental content (%) : C, 85.57; H, 5.67; N, 2.10.
[0304] Synthesis Example 21: Preparation of compound 2-327
[0305]
[0306] According to the preparation method of synthesis example 14, replace equal moles of a-2-15 with equal moles of a-2-365 to obtain compound 2-365 (16.46 g) with HPLC purity ≧ 99.96%. Mass spectrum m / z: 588.2209 (theoretical value: 588.2202). Theoretical elemental content (%) C 45 H 28 N2O: C, 88.21 ; H, 4.61 ; N, 4.57. Found elemental content (%) : C, 88.17; H, 4.62; N, 4.58.
[0307] Synthesis example 22: preparation of compound 2-365
[0308]
[0309] According to the preparation method of synthesis example 14, replace equal moles of a-2-15 with equal moles of a-2-365 to obtain compound 2-365 (16.46 g) with HPLC purity ≧ 99.96%. Mass spectrum m / z: 588.2209 (theoretical value: 588.2202). Theoretical elemental content (%) C 43 H 28 N2O: C, 87.73; H, 4.79; N, 4.76. Found elemental content (%) : C, 87.77; H, 4.80; N, 4.73.
[0310] Synthesis example 23: preparation of compound 2-378
[0311]
[0312] According to the preparation method of synthesis example 14, replace equal moles of a-2-15 with equal moles of a-2-378 to obtain compound 2-378 (17.32 g) with HPLC purity ≧ 99.94%. Mass spectrum m / z: 677.2710 (theoretical value: 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Found elemental content (%) : C, 90.39; H, 5.18; N, 2.05.
[0313] Synthesis example 24: preparation of compound 2-400
[0314]
[0315] Following the procedure of the preparation of synthesis example 14, replace the equal moles of a-2-15 with equal moles of a-2-530, and equal moles of b-2-15 with equal moles of b-2-530, to obtain compound 2-530 (14.22 g) with HPLC purity > 99.95%. Mass spectrum m / z: 588.2213 (calcd: 588.2202). Theoretical elemental content (%) C 47 H 30 N2O: C, 87.73; H, 4.79; N, 4.76. Found elemental content (%) C, 87.70; H, 4.81; N, 4.75.
[0316] Synthesis Example 25: Preparation of compound 2-463
[0317]
[0318] Following the procedure of the preparation of synthesis example 14, replace the equal moles of a-2-15 with equal moles of a-2-463, and equal moles of b-2-15 with equal moles of b-2-463, to obtain compound 2-463 (16.61 g) with HPLC purity > 99.91%. Mass spectrum m / z: 611.2232 (calcd: 611.2249). Theoretical elemental content (%) C 46 H 29 NO: C, 90.32; H, 4.78; N, 2.29. Found elemental content (%) C, 90.35; H, 4.74; N, 2.27.
[0319] Synthesis Example 26: Preparation of compound 2-530
[0320]
[0321] Following the procedure of the preparation of synthesis example 14, replace the equal moles of a-2-15 with equal moles of a-2-530, and equal moles of b-2-15 with equal moles of b-2-530, to obtain compound 2-530 (14.22 g) with HPLC purity > 99.95%. Mass spectrum m / z: 588.2213 (calcd: 588.2202). Theoretical elemental content (%) C 43 H 28 N2O: C, 87.73; H, 4.79; N, 4.76. Found elemental content (%) C, 87.70; H, 4.81; N, 4.75.
[0322] Synthesis Example 27: Preparation of compound 2-607
[0323]
[0324] According to the preparation method of synthesis example 14, replace equal moles of a-2-15 with equal moles of a-2-742 to obtain compound 2-742 (13.22 g) with HPLC purity > 99.96%. Mass spectrum m / z: 503.2261 (theoretical value: 503.2249). Theoretical elemental content (%) C 44 H 29 NO: C, 88.24; H, 5.80; N, 2.78. Found elemental content (%): C, 88.27; H, 5.78; N, 2.77.
[0325] Synthesis Example 28: Preparation of compound 2-742
[0326]
[0327] According to the preparation method of synthesis example 14, replace equal moles of a-2-15 with equal moles of a-2-742 to obtain compound 2-742 (13.22 g) with HPLC purity > 99.96%. Mass spectrum m / z: 503.2261 (theoretical value: 503.2249). Theoretical elemental content (%) C 37 H 29 NO: C, 88.24; H, 5.80; N, 2.78. Found elemental content (%): C, 88.27; H, 5.78; N, 2.77.
[0328] Synthesis Example 29: Preparation of compound 2-879
[0329]
[0330] According to the preparation method of synthesis example 14, replace equal moles of a-2-15 with equal moles of a-2-879 and equal moles of b-2-15 with equal moles of b-2-879 to obtain compound 2-879 (16.42 g) with HPLC purity > 99.92%. Mass spectrum m / z: 627.2546 (theoretical value: 627.2562). Theoretical elemental content (%) C 47 H 33 NO: C, 89.92; H, 5.30; N, 2.23. Found elemental content (%): C, 89.95; H, 5.33; N, 2.24.
[0331] Synthesis Example 30: Preparation of compound 2-1095
[0332]
[0333] According to the preparation method of Synthesis Example 14, replace equal moles of a-2-15 with equal moles of a-2-1095 to obtain compound 2-1095 (18.49 g) with an HPLC purity of ≧99.97%. Mass spectrum m / z: 713.3126 (theoretical value: 713.3116). Theoretical elemental content (%) C 52 H 43 NS: C, 87.48; H, 6.07; N, 1.96. Actual elemental content (%) C, 87.51; H, 6.04; N, 1.98.
[0334] Device Example:
[0335] Test conditions: The test software, computer, K2400 digital source meter produced by Keithley Company of the United States, and PR788 spectral scanning luminance meter of Photo Research Company of the United States are combined into a joint IVL test system to test the driving voltage and luminous efficiency of the organic electroluminescent device. The OLED lifetime test system M6000 of McScience Company is used to test the lifetime of the organic electroluminescent device.
[0336] The test environment is atmospheric environment, and the temperature is room temperature; the driving voltage, luminous efficiency, and the time required for the luminance to decrease to 95% of the initial luminance (T95) are measured at a current density of 10 mA / cm 2 .
[0337] Test preparation: The ITO (10 nm) / Ag (100 nm) / ITO (10 nm) glass substrate is cleaned in distilled water for 2 times, ultrasonic washing for 30 minutes, and then cleaned in distilled water for 2 times, ultrasonic washing for 10 minutes. After the distilled water cleaning is completed, the solvents of isopropyl alcohol, acetone, and methanol are sequentially subjected to ultrasonic washing, and then dried on a hot plate heated to 120°C. The dried substrate is transferred to a plasma cleaning machine for washing for 5 minutes.
[0338] The functional layer compounds required for preparing the organic electroluminescent device are as follows:
[0339]
[0340] Device Example 1: Preparation of a blue organic electroluminescent device
[0341] The cleaned ITO / Ag / ITO substrate was transferred into an evaporation machine, and 10 nm of HI-1 and HT-1 as a hole injection layer (mass ratio of HI-1 to HT-1 was 3:97) were evaporated on the ITO / Ag / ITO substrate, 120 nm of HT-1 as a first hole transport layer was evaporated on the hole injection layer, 5 nm of the compound 1-4 of the present application as a second hole transport layer was vacuum evaporated on the hole transport layer, a light-emitting layer containing BH-1 as a host material and BD-1 as a dopant material (mass ratio of BH-1 to BD-1 was 98:2) was vacuum evaporated on the second hole transport layer, and then 5 nm of the compound 2-163 of the present application as a hole blocking layer was vacuum evaporated on the light-emitting layer, 30 nm of ET-1 and Liq as an electron transport layer (mass ratio of ET-1 to Liq was 1:1) was evaporated on the hole blocking layer, 1 nm of LiF as an electron injection layer was evaporated on the electron transport layer, and then 13 nm of Mg:Ag (Mg:Ag = 1:9, mass ratio) as a cathode was evaporated on the electron injection layer, and then 70 nm of CP-1 as a cover layer was evaporated on the cathode, thereby preparing an organic electroluminescent device.
[0342] Device Examples 2 to 47: Preparation of a blue organic electroluminescent device
[0343] The compounds in Table 1 were used to replace the compound 1-4 in Device Example 1 as a second hole transport layer material, and the compound 2-163 was used to replace the compound 2-163 in Device Example 1 as a hole blocking layer material, and an organic electroluminescent device was prepared by the same preparation method as in Device Example 1.
[0344] Comparative Examples 1 to 8:
[0345] Ref-1 in Table 1 was used to replace the compound 1-4 in Device Example 1 as a second hole transport layer material, and 2-182, 2-263, 2-281, 2-292, 2-307, 2-333, 2-378, and Ref-2 were used to replace the compound 2-163 in Device Example 1 as a hole blocking layer material, and an organic electroluminescent device was prepared by the same preparation method as in Device Example 1.
[0346] Comparative Examples 9 to 15:
[0347] 1-84, 1-138, 1-181, 1-189, 1-269, 1-438, and 1-514 in Table 1 were used to replace the compound 1-4 in Device Example 1 as a second hole transport material, and Ref-2 was used to replace the compound 2-163 in Device Example 1 as a hole blocking layer material, and an organic electroluminescent device was prepared by the same preparation method as in Device Example 1.
[0348] Comparative Example 16:
[0349] The cleaned ITO / Ag / ITO substrate was transferred to an evaporation machine, and 10 nm-thick HI-1 and HT-1 were evaporated on the ITO / Ag / ITO substrate as a hole injection layer (mass ratio of HI-1 to HT-1 was 3:97), 125 nm-thick HT-1 was evaporated on the hole injection layer as a first hole transport layer, a light-emitting layer was vacuum-evaporated on the first hole transport layer, the light-emitting layer contained BH-1 as a host material and BD-1 as a dopant material (mass ratio of BH-1 to BD-1 was 98:2), the thickness of the light-emitting layer was 25 nm, then 5 nm-thick compound 2-182 of the present application was vacuum-evaporated on the light-emitting layer as a hole blocking layer, 30 nm-thick ET-1 and Liq were evaporated on the hole blocking layer as an electron transport layer (mass ratio of ET-1 to Liq was 1:1), 1 nm-thick LiF was evaporated on the electron transport layer as an electron injection layer, then 13 nm-thick Mg:Ag (Mg:Ag = 1:9, mass ratio) was evaporated on the electron injection layer as a cathode, and then 70 nm-thick CP-1 was evaporated on the cathode as a capping layer, thereby preparing an organic electroluminescent device.
[0350] Comparative Examples 17 to 20:
[0351] An organic electroluminescent device was prepared by the same preparation method as in Comparative Example 16, except that compound 2-240, 2-292, 2-652, and 2-815 in Table 1 were used instead of compound 2-182 in Comparative Example 16 as a hole blocking layer material, respectively.
[0352] Comparative Example 21:
[0353] The cleaned ITO / Ag / ITO substrate was transferred to an evaporation machine, and 10 nm-thick HI-1 and HT-1 were evaporated on the ITO / Ag / ITO substrate as a hole injection layer (mass ratio of HI-1 to HT-1 was 3:97), 120 nm-thick HT-1 was evaporated on the hole injection layer as a first hole transport layer, 5 nm-thick Compound 1-5 of the present application was vacuum evaporated on the first hole transport layer as a second hole transport layer, a light-emitting layer containing BH-1 as a host material and BD-1 as a dopant material (mass ratio of BH-1 to BD-1 was 98:2) was vacuum evaporated on the second hole transport layer to a thickness of 25 nm, then 35 nm-thick ET-1 and Liq were vacuum evaporated on the light-emitting layer as an electron transport layer (mass ratio of ET-1 to Liq was 1:1), 1 nm-thick LiF was evaporated on the electron transport layer as an electron injection layer, then 13 nm-thick Mg:Ag (Mg:Ag = 1:9, mass ratio) was evaporated on the electron injection layer as a cathode, and then 70 nm-thick CP-1 was evaporated on the cathode as a capping layer, thereby preparing an organic electroluminescent device.
[0354] Comparative Examples 22 to 25:
[0355] An organic electroluminescent device was prepared by the same preparation method as in Comparative Example 21, except that Compound 1-51, 1-146, 1-171, and 1-505 in Table 1 were used instead of Compound 1-5 in Comparative Example 21 as a second hole transport layer material, respectively.
[0356] Table 1: Test results of the luminescent properties of the organic electroluminescent devices 1 to 47 and Comparative Examples 1 to 25
[0357]
[0358]
[0359] According to the results in Table 1 of the present application, it can be seen that when the compounds of the present application are applied to the second hole transport layer and the hole blocking layer of an organic electroluminescent device, the device exhibits low driving voltage, high luminous efficiency, and long lifetime.
[0360] Device Example 48: Preparation of a green organic electroluminescent device
[0361] The cleaned ITO / Ag / ITO substrate was transferred to an evaporation machine, and 10 nm of HI-1 and HT-2 were evaporated on the ITO / Ag / ITO substrate as a hole injection layer (mass ratio of HI-1 to HT-2 was 3:97), 120 nm of the compound 1-4 of the present application was evaporated on the hole injection layer as a hole transport layer, a light-emitting layer was vacuum evaporated on the hole transport layer, the light-emitting layer contained GH-1 and GH-2 as host materials, and GD-1 as a dopant material (mass ratio of GH-1, GH-2 to GD-1 was 48:48:2), then 30 nm of the compound 2-15 of the present application was vacuum evaporated on the light-emitting layer as an electron transport layer, 1 nm of LiF was evaporated on the electron transport layer as an electron injection layer, then 13 nm of Mg:Ag (Mg:Ag = 1:9, mass ratio) was evaporated on the electron injection layer as a cathode, then 70 nm of CP-2 was evaporated on the cathode as a cover layer, thereby preparing an organic electroluminescent device.
[0362]
[0363] Device Examples 49 to 80: Preparation of green organic electroluminescent devices
[0364] An organic electroluminescent device was prepared by the same preparation method as in Device Example 48, using the compounds in Table 1 instead of the compound 1-4 in Device Example 1 as a hole transport layer material, and the compound 2-15 as an electron transport layer material, respectively.
[0365] Comparative Examples 26 to 31:
[0366] An organic electroluminescent device was prepared by the same preparation method as in Device Example 48, using HT-2 instead of the compound 1-4 in Device Example 48 as a hole transport material, and the compounds 2-182, 2-240, 2-263, 2-292, 2-815, 2-952 instead of the compound 2-15 in Device Example 48 as an electron transport layer material, respectively.
[0367] Comparative Examples 32 to 37:
[0368] An organic electroluminescent device was prepared by the same preparation method as in Device Example 48, using the compounds 1-84, 1-146, 1-171, 1-189, 1-382, 1-514 instead of the compound 1-4 in Device Example 48 as a hole transport material, and ET-2 instead of the compound 2-15 in Device Example as an electron transport layer material, respectively.
[0369] Comparative Example 38:
[0370] An organic electroluminescent device was produced in the same manner as in Device Example 48, except for using compound HT-2 instead of compound 1-4 in Device Example 48 as a hole transport material, and using ET-2 instead of compound 2-15 in Device Example as an electron transport layer material.
[0371] Comparative Example 39:
[0372] An organic electroluminescent device was produced in the same manner as in Device Example 48, except for using compound Ref-1 instead of compound 1-4 in Device Example 48 as a hole transport material, and using Ref-2 instead of compound 2-15 in Device Example as an electron transport layer material.
[0373] Comparative Example 40:
[0374] An organic electroluminescent device was produced in the same manner as in Device Example 48, except for using compound Ref-3 instead of compound 1-4 in Device Example 48 as a hole transport material, and using Ref-4 instead of compound 2-15 in Device Example as an electron transport layer material.
[0375] Table 2: Test results of the luminescent properties of the organic electroluminescent devices 48-80, Comparative Examples 26-40
[0376]
[0377]
[0378] According to the results of Table 2, it can be seen that when the compounds of the present application are used in the hole transport layer and the electron transport layer of the organic electroluminescent device, the device exhibits low driving voltage, high luminescent efficiency and long lifetime.
[0379] It should be noted that the present application is described in particular with individual embodiments, but those skilled in the art can make various forms or details of improvements to the present application without departing from the principles of the present application, and these improvements also fall within the scope of protection of the present application.
Claims
1. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode, characterized in that, The hole transport region comprises a triarylamine compound represented by Formula 1, and the electron transport region comprises a heterocyclic compound represented by Formula 2. In Formula 1, R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloyl group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic rings, fused cycloyl group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl rings; or any one of R1 and R2 is directly bonded to L3; The W is independently selected from C(R0) or N; The R0 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R0s are connected to form a substituted or unsubstituted ring; L1, L2, and L3 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene. The Ar1 and Ar2 are independently selected from any one of the following groups: The X is independently selected from C(R6) or N, and the X bonded to L1 and L2 is selected from C atoms; The Y1 is selected from O or N(R) 10 The Y2 is selected from O, S, or N(R). 11 ); The R3 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted silyl. R4 and R5 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R6 are connected to form a substituted or unsubstituted ring; m1 is selected from 1 or 2; The R 10 R 11 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The Q atoms independently are selected from C(Rd) or N; the Q atoms bonded to La are selected from C atoms; Z0 is selected from O, S, or N (Re); The La is independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene; The n is selected from 1, 2, 3 or 4; when there are two or more La, the two or more La are the same or different from each other; The Ra, Rd, and Re are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rd are connected to form a substituted or unsubstituted ring; A is selected from formula 2-1 or formula 2-2. The V atoms are independently selected from C (Rf) or N atoms, and the V atoms bonded to La are selected from C atoms; Z1 is selected from O, S, C (RgRh) or N (Ri); The Rb, Rc, Rg, and Rh are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or Rb is connected to Rc to form a substituted or unsubstituted ring; or Rg is connected to Rh to form a substituted or unsubstituted ring. The Rf is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rf are connected to form a substituted or unsubstituted ring; The Ri is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.
2. The organic electroluminescent device according to claim 1, characterized in that, The compound of Formula 1 is selected from Formula 1-1 or Formula 1-2: In Equations 1-1 and 1-2, R1' and R2' are independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, vinyl, propenyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutene. The following are all of the following: benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthraceneyl, phenanthreneyl, triphenylene, pyreneyl, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, dibenzofuranyl, dibenzothiopheneyl, benzofuranyl, benzothiopheneyl, indoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, o-phenanthrolinel, carbazoleyl, oxazolyl, thiazolyl, imidazoleyl, benzooxazolyl, benzothiazolyl, and benzimidazolyl; The "substituted" group is selected from any one of deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The definitions of W, L1 to L3, Ar1, and Ar2 are the same as those in Equation 1.
3. The organic electroluminescent device according to claim 1, characterized in that, The Ar1 and Ar2 are independently selected from any one of the following groups: R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C6-C30 aryl. The R 12 R 12 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The R 10 R 11 The independent group is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C6-C30 aryl. The a1 is independently selected from 1, 2, 3, 4 or 5; the a2 is independently selected from 1, 2, 3 or 4; the a3 is independently selected from 1, 2 or 3; the a4 is independently selected from 1 or 2; the a5 is independently selected from 1, 2, 3, 4, 5 or 6; the a6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; and the a8 is independently selected from 1, 2, 3, 4, 5, 6 or 7.
4. The organic electroluminescent device according to claim 1, characterized in that, The L1, L2, and L3 are independently selected from single bonds or any one of the following groups: The R 13 R 13 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; The Y3 is selected from O, S, or C(R). 14 R 15 ); The R 14 R 15 Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; or R 14 R 15 The links between them form substituted or unsubstituted rings; The b1 is independently selected from 1, 2, 3 or 4; the b2 is independently selected from 1 or 2; the b3 is independently selected from 1, 2, 3, 4, 5 or 6; the b4 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; and the b5 is independently selected from 1, 2 or 3.
5. The organic electroluminescent device according to claim 1, characterized in that, The Selected from any one of the following groups: Z0 is selected from O, S, or N (Re); The Ra is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The Rd is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The Re is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The q1 is independently selected from 1, 2, 3 or 4; the q2 is independently selected from 1, 2 or 3; the q3 is independently selected from 1 or 2; the q4 is independently selected from 1, 2, 3, 4, 5 or 6; the q5 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; the q6 is independently selected from 1, 2, 3, 4, 5, 6 or 7; and the q7 is independently selected from 1, 2, 3, 4 or 5.
6. The organic electroluminescent device according to claim 1, characterized in that, The A group is independently selected from any one of the following groups: The Rb' and Rc' are independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutenyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, trimethylsilane, triethylsilane, triphenylsilane, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzo[] Cyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, o-phenanthrolinel, benzofuranyl, benzothiophene, indyl, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl; The Rf and Rf' are independently selected from any one of the following groups, which are hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophene, dibenzofuran, dibenzothiophene, benzoxazolyl, benzothiazolyl, and benzimidazolyl. Z1 is independently selected from O, S, C (RgRh) or N (Ri); The Rg, Rh, and Ri are independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothiophene, benzoxazolyl, benzothiazolyl, and benzimidazolyl. The p1 is independently selected from 1, 2, 3, 4, 5, 6, or 7; the p2 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the p3 is independently selected from 1, 2, or 3; the p4 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8; the p5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the p6 is independently selected from 1, 2, 3, 4, 5, or 6; the p7 is independently selected from 1, 2, 3, 4, or 5; the p8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the p9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the p 10 The p is independently selected from 1, 2, 3, or 4. 11 The independent selection is from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.
7. The organic electroluminescent device according to claim 1, characterized in that, The La is selected from a single bond or any one of the following groups: The E is independently selected from C(Rj) or N; The Rj is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. Z2 is selected from O, S or C (RkRl), and Z3 is selected from O, S, C (RmRn) or N (Rp); The Rk, Rl, Rm, Rn, and Rp are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or adjacent Rk and Rl are connected to form a substituted or unsubstituted ring.
8. The organic electroluminescent device according to claim 1, characterized in that, The L1, L2, and L3 are independently selected from single bonds or any one of the following groups: The R 13 R 13 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; The Y3 is selected from O, S, or C(R). 14 R 15 ); The R 14 R 15 The independent group is selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C6-C30 aryl. The b1 is independently selected from 1, 2, 3 or 4; the b2 is independently selected from 1 or 2; the b3 is independently selected from 1, 2, 3, 4, 5 or 6; the b4 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; and the b5 is independently selected from 1, 2 or 3.
9. The organic electroluminescent device according to claim 1, characterized in that, The triarylamine compound represented by Formula 1 is selected from any of the following structures:
10. The organic electroluminescent device according to claim 1, characterized in that, The heterocyclic compound represented by Formula 2 is selected from any of the following structures: