Organic light-emitting device
By using the first and second compounds of a specific structure in the light emitting layer of the OLED device, the HOMO and LUMO energy levels are solved, and the problem that existing OLED devices are difficult to reduce the driving voltage while improving the luminous efficiency and extending their service life is achieved, achieving more efficient and long-lasting luminous performance.
Patent Information
- Application Number
- CN202510232400.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-02-28
- Publication Date
- 2025-05-30
AI Technical Summary
While existing OLED devices improve luminous efficiency and extend their service life, it is difficult to reduce the driving voltage, affecting device performance.
Using a light emitting layer containing the first compound and the second compound, the first compound having a specific structure and the second compound having a specific structure, the matching of the energy level with the hole transport region and the electron transport region is improved by optimizing the HOMO and LUMO energy levels in the light emitting layer.
It improves the luminous efficiency and service life of OLED devices, while reducing the driving voltage and improving the overall performance.
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Abstract
Description
Technical Field
[0001] The present invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescent device. Background Art
[0002] Organic Light-Emitting Diode (hereinafter simply referred to as OLED) has characteristics such as being thin and light in body, having a wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity, and good flexibility. It has been widely used in the fields of lighting and display, and is considered by the industry to be one of the most promising display and lighting technologies.
[0003] A classic OLED device has a "sandwich" structure, with a light-emitting layer sandwiched between two electrodes, a cathode and an anode. The light-emitting layer contains a light-emitting substance (guest material). After power is applied to the electrodes, holes and electrons are injected from the anode and the cathode respectively, reach the light-emitting layer, and then recombine to generate excitons, releasing energy. Under the action of an electric field, the excitons migrate, transfer the energy to the light-emitting substance, and the electrons in the light-emitting substance molecules transition from the ground state to the excited state. Since the excited state is unstable, the electrons return from the excited state to the ground state, thus releasing energy in the form of light and generating a light-emitting phenomenon. In general, in order to further improve the device performance, a hole transport region is also provided between the anode and the light-emitting layer, and an electron transport region is provided between the cathode and the light-emitting layer. The hole transport region mainly plays the role of injecting and transporting holes, and can include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, etc.; the electron transport region mainly plays the role of injecting and transporting electrons, and can include an electron injection layer, an electron transport layer, a hole blocking layer, etc. The energy levels between the various organic functional layers need to be well matched, so as to prevent excitons from diffusing from the light-emitting layer to other organic functional layers, thereby maintaining a high ratio of effective light emission in the light-emitting layer. This can not only improve the light-emitting efficiency of the device, but also avoid the rapid aging of organic materials due to the reduction of heat generated by interface luminescence, and thus extend the service life of the device. In addition to setting organic functional layers between the anode and the cathode, a covering layer with high refractive index and high light transmittance is also provided outside the electrode on the light-emitting side to further improve the light-emitting efficiency and color purity of the device.
[0004] In order to improve the light-emitting efficiency and service life of OLED devices and reduce the driving voltage, OLED workers need to continuously optimize the device structure, especially the energy level matching between the various organic functional layers. Developing OLED devices containing two or more host materials is one of the very effective means. Summary of the Invention
[0005] To solve the above technical problems, 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 includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the anode and the cathode. The hole transport region is located between the anode and the light-emitting layer. The electron transport region is located between the cathode and the light-emitting layer. The light-emitting layer contains a first compound and a second compound. The first compound has a structure represented by formula (I), and the second compound has a structure represented by formula (II) or formula (III):
[0006]
[0007] Each time X appears, it is the same or different and is selected from CR or a nitrogen atom, and at least three are carbon atoms connected to L 1 、L 2 、L 3 ;
[0008] The Ar 1 is selected from one of the following groups:
[0009]
[0010] Wherein, each time the a 1 appears, it is the same or different and is selected from 0, 1, 2, 3 or 4; each time the b 1 appears, it is the same or different and is selected from 0, 1, 2 or 3;
[0011] The Ar 2 is selected from one of the following groups:
[0012]
[0013] Wherein, the Y is selected from an oxygen atom, a sulfur atom or N-Ar 5 ;
[0014] The Ar 3 is selected from one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring. And, the Ar 3 is not selected from a substituted or unsubstituted triazinyl group;
[0015] The Z 1 、Z 2 are independently selected from a single bond, O, S, CR a R b or N-L 601 -Ar 601, and at least one of them is not a single bond;
[0016] The Ar described above 4 Ar, 5 Ar, 201 Ar, 301 Ar, 501 Ar, 601 R, a R, b are independently selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring. Alternatively, the R a R, b can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbocyclic ring;
[0017] The ring C, ring E, ring F, ring G, ring H, ring I, ring J, ring K are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, and a ring formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0018] The R, R 1 R, 2 each time it appears, is the same or different and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0019] The L described above 1 L, 2 L, 3 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted benzofuranyl group, and a substituted or unsubstituted benzothiophenyl group;
[0020] The L 4 L, 201 L, 301 L, 401 L, 501 L, 601Independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a divalent group formed by fusing a C3-C12 alicyclic ring and a C6-C30 aromatic ring.
[0021] Beneficial effects:
[0022] The light-emitting layer of the organic electroluminescent device provided by the present invention selects two host materials, namely a first compound represented by formula (I) and a second compound represented by formula (II) or formula (III). When used in combination, the light-emitting layer has appropriate HOMO energy levels and LUMO energy levels, can be well matched with the energy levels of the organic functional layers in the adjacent hole transport region and electron transport region, thereby improving the light-emitting efficiency and service life of the device, and reducing the driving voltage at the same time. Specific embodiments
[0023] The technical solutions of the specific embodiments of the present invention will be described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative efforts belong to the protection scope of the present invention.
[0024] In the compounds of the present invention, any atom not specified as a specific isotope includes any stable isotope of that atom, and includes atoms in both their natural isotope abundances and non-natural abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains approximately 0.0156 atom% deuterium.
[0025] In the present invention, the use of "H" and "hydrogen atom" means that the hydrogen atoms in the chemical structure contain no more than the deuterium atoms or tritium atoms in natural abundance. For example, no more than 0.0156 atom% deuterium. "D" and "deuterium atom" refer to abundances of deuterium content above natural abundance, such as any value exceeding 0.1 atom%, exceeding 1 atom%, exceeding 10 atom%, for example, about 95 atom% deuterium therein. "T" and "tritium atom" refer to abundances of tritium content above natural abundance, such as any value exceeding 0.1 atom%, exceeding 1 atom%, exceeding 10 atom%, for example, about 95 atom% tritium therein. In the present invention, the omission of hydrogen not drawn represents "H" or "hydrogen atom".
[0026] The halogen atoms described in the present invention refer to fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0027] The "silyl group" described in the present invention refers to —SiH 3The "substituted or unsubstituted silyl group" means that one or more H groups on the silyl group are substituted or unsubstituted by a substituent. The "substituted or unsubstituted silyl group" can be -Si(R k ) 3 Indicates that each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms in the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms in the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms in the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R k The same or different radicals are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinoline. Preferred substituted silyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, etc., but are not limited thereto. The above-mentioned substituted silyl groups are preferably trimethylsilyl, triethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldimethylsilyl.
[0028] As used herein, the alkyl group refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc.; the branched-chain alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc. The above alkyl groups are preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
[0029] As used herein, the cycloalkyl group refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto. The above cycloalkyl groups are preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, norbornyl.
[0030] As used herein, the cycloalkenyl group refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The above cycloalkenyl groups are preferably cyclopentenyl, cyclohexenyl.
[0031] As used herein, the heterocycloalkyl group refers to a group formed by removing one hydrogen atom from a heterocyclic molecule in which the atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, phosphorus, etc., preferably nitrogen, oxygen, sulfur. Preferably, it contains 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. Preferably, it has 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include oxiranyl, thioethyl, aziridinyl, pyrrolidinyl, piperidyl, morpholinyl, thiomorpholinyl, piperazinyl, etc., but are not limited thereto. The above heterocyclic groups are preferably pyrrolidinyl, piperidyl, morpholinyl, thiomorpholinyl, piperazinyl.
[0032] As used herein, the term "aryl" refers to the general name of a monovalent group remaining after removing a hydrogen atom from the aryl carbon of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl having only one aromatic ring in the molecule, such as phenyl, etc., but not limited thereto; the polycyclic aryl refers to an aryl having two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl having two or more aromatic rings and fused together by sharing two adjacent carbon atoms, such as naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited thereto. The above aryls are preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.
[0033] As used herein, the term "heteroaryl" refers to the general name of a group obtained by replacing one or more aryl carbon atoms in an aryl with a heteroatom. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The connection site of the heteroaryl can be located on a ring-forming carbon atom or a ring-forming nitrogen atom. The heteroaryl can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The monocyclic heteroaryl includes furyl, thienyl, pyrrolyl, imidazolyl, pyridyl, pyrimidinyl, etc., but not limited thereto; the polycyclic heteroaryl includes phenylfuryl, phenylthienyl, etc., but not limited thereto; the fused-ring heteroaryl includes benzothienyl, benzofuryl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, benzodibenzofuryl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, etc., but not limited thereto. The above heteroaryls are preferably benzothienyl, benzofuryl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, pyridyl.
[0034] The monovalent group formed by the fusion of an alicyclic ring and an aromatic ring in the present invention refers to the general term of the monovalent group remaining after removing one hydrogen atom from the fused alicyclic ring (cycloalkane, cycloalkene, cycloalkyne) and aromatic ring. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and it may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the alicyclic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, and it may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, cycloheptyne. Preferably, examples of the monovalent group formed by the fusion of an alicyclic ring and an aromatic ring may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.
[0035] The arylene group in the present invention means an aryl group having two bonding sites, that is, a divalent group. Regarding this, the description of the aryl group provided above can be applied, with the difference being that the arylene group is a divalent group.
[0036] The heteroarylene group in the present invention means a heteroaryl group having two bonding sites, that is, a divalent group. Regarding this, the description of the heteroaryl group provided above can be applied, with the difference being that the heteroarylene group is a divalent group.
[0037] The divalent group formed by the fusion of an alicyclic ring and an aromatic ring in the present invention refers to the group formed by the fusion of an alicyclic ring and an aromatic ring having two bonding sites, that is, a divalent group. Regarding this, the description of the group formed by the fusion of an alicyclic ring and an aromatic ring provided above can be applied, with the difference being that the divalent group formed by the fusion of an alicyclic ring and an aromatic ring is a divalent group.
[0038] "Substituted" in the present invention means that a hydrogen atom in certain functional groups is replaced by another atom or functional group (i.e., a substituent), and the position of substitution is not restricted as long as it is the position where the hydrogen atom is substituted, and when two or more are substituted, the two or more substituents may be the same or different from each other.
[0039] As used herein, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, halogen atom, amino group, cyano group, nitro group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted silyl group, preferably deuterium atom, halogen atom, cyano group, nitro group, C1-C12 alkyl group, C3-C12 cycloalkyl group, C3-C12 cycloalkenyl group, C3-C12 heterocycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, substituted or unsubstituted silyl group; when substituted with multiple substituents, the multiple substituents may be the same or different from each other; preferably, it means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, deuterated tert-butyl group, cyclopropyl group, methyl-substituted cyclopropyl group, ethyl-substituted cyclopropyl group, deuterated cyclopropyl group, cyclobutyl group, methyl-substituted cyclobutyl group, ethyl-substituted cyclobutyl group, deuterated cyclobutyl group, cyclopentyl group, methyl-substituted cyclopentyl group, ethyl-substituted cyclopentyl group, deuterated cyclopentyl group, cyclohexyl group, methyl-substituted cyclohexyl group, ethyl-substituted cyclohexyl group, n-propyl-substituted cyclohexyl group, n-butyl-substituted cyclohexyl group, cyclohexane-substituted cyclohexyl group, deuterated cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, adamantyl group, methyl-substituted adamantyl group, ethyl-substituted adamantyl group, deuterated adamantyl group, norbornyl group, methyl-substituted norbornyl group, ethyl-substituted norbornyl group, deuterated norbornyl group, pyrrolidinyl group, piperidinyl group, morpholinyl group, thiomorpholinyl group, methyl-substituted piperazinyl group, ethyl-substituted piperazinyl group, phenyl-substituted piperazinyl group, naphthyl-substituted piperazinyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, anthryl group, deuterated anthryl group, phenanthryl group, deuterated phenanthryl group, triphenylenyl group, pyrenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, spiro-cyclopentyl-fluorenyl group, spiro-cyclohexyl-fluorenyl group, spiro-adamantyl-fluorenyl group, spiro-cyclopentenyl-fluorenyl group, spiro-cyclohexenyl-fluorenyl group, N-phenylcarbazolyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, benzo-dibenzofuranyl group, dibenzothiophenyl group, benzo-dibenzothiophenyl group, benzoxazolyl group, benzothiazolyl group, pyridyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, trimethylsilyl group, triphenylsilyl group; when substituted with multiple substituents, the multiple substituents may be the same or different from each other, and two adjacent substituents may be linked to form a ring.
[0040] In this specification, when the position of a substituent or a linking site on a ring is not fixed, it means that it can be linked to any one of the optional sites of the ring. For example, can represent can represent can represent and so on.
[0041] In this specification, when the bond where a substituent or a linking site is located passes through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically, it can be linked to any one of the corresponding optional sites of the rings. For example, can represent or can represent can represent and so on.
[0042] The connected to form a ring structure (such as forming a saturated or unsaturated C3-C10 carbocyclic ring, forming a substituted or unsubstituted saturated or unsaturated C3-C6 alicyclic ring) as described in the present invention means that each group is connected to each other through a chemical bond, and optionally forms a double bond / triple bond, and can form an aromatic group, as exemplified below:
[0043]
[0044] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane-fused benzene, cyclohexene, cyclohexane, cyclohexane-fused benzene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but not limited thereto.
[0045] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.
[0046] In the present invention, a certain layer being "above" another layer or an electrode can be interpreted as being directly above the other layer or the electrode, or there may be other layer structures in between.
[0047] In the present invention, a certain layer being "between" two layers, two electrodes or one layer and an electrode can be interpreted as the only layer structure between the two, or there may be one or more layer structures between the two.
[0048] 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 includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the cathode and the light-emitting layer. The light-emitting layer contains a first compound and a second compound. The first compound has a structure represented by formula (I), and the second compound has a structure represented by formula (II) or formula (III):
[0049]
[0050] Each occurrence of X is independently selected from CR or a nitrogen atom, and at least three of them are carbon atoms connected to L 1 、L 2 、L 3 ;
[0051] Ar 1 is selected from one of the following groups:
[0052]
[0053] wherein, each occurrence of a 1 is independently selected from 0, 1, 2, 3 or 4; each occurrence of b 1 is independently selected from 0, 1, 2 or 3;
[0054] Ar 2 is selected from one of the following groups:
[0055]
[0056] wherein, Y is selected from an oxygen atom, a sulfur atom or N-Ar 5 ;
[0057] Ar 3 is selected from one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring. And, Ar 3 is not selected from a substituted or unsubstituted triazinyl group;
[0058] Z 1 、Z 2 are independently selected from a single bond, O, S, CR a R b or N-L 601 -Ar 601 , and at least one of them is not a single bond;
[0059] The described Ar 4 、Ar 5 、Ar 201 、Ar 301 、Ar 501 、Ar 601 、R a 、R b are independently selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, or the described R a 、R b can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbocyclic ring;
[0060] The described ring C, ring E, ring F, ring G, ring H, ring I, ring J, ring K are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, a ring formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0061] The described R, R 1 、R 2 each time it appears, is the same or different and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0062] The described L 1 、L 2 、L 3 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group;
[0063] The described L 4 、L 201 、L 301 、L 401 、L 501 、L 601Independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring.
[0064] Preferably, the substituents in the "substituted or unsubstituted" are independently selected from a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and one or more of a monovalent group formed by the fusion of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring. When there are multiple substituents, the multiple substituents are the same or different.
[0065] Preferably, the substituents in the "substituted or unsubstituted" are independently selected from a deuterium atom; a fluorine atom; a cyano group; a methyl group substituted or unsubstituted by a deuterium atom or a fluorine atom; an ethyl group; a n-propyl group; an isopropyl group substituted or unsubstituted by a deuterium atom or a fluorine atom; a n-butyl group; a sec-butyl group; an isobutyl group; a tert-butyl group substituted or unsubstituted by a deuterium atom or a fluorine atom; a group shown below substituted or unsubstituted by one or more of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl; a group shown below substituted or unsubstituted by one or more of a deuterium atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl: phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl; one or more of a silyl group substituted or unsubstituted by one or more of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a phenyl group substituted by a methyl group, a phenyl group substituted by a tert-butyl group, a phenyl group substituted by a fluorine atom, a phenyl group substituted by a cyano group, a phenyl group substituted by an adamantyl group, a phenyl group substituted by a norbornyl group, a naphthyl group, a deuterated naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, a pyridyl group, a pyrimidinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and 9,9-dimethylfluorenyl. When there are multiple substituents, the multiple substituents are the same or different.
[0066] Preferably, the ring C, ring E, ring F, ring G, ring H, ring I, ring J, and ring K are independently selected from one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, fluorene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring, benzocyclopropane ring, benzocyclobutane ring, benzocyclopentane ring, benzocyclohexane ring, benzocycloheptane ring.
[0067] Preferably, the Ar 2 is selected from one of the following groups:
[0068]
[0069]
[0070]
[0071] wherein each occurrence of the a 2 is independently selected from 0, 1, or 2; each occurrence of the b 2 is independently selected from 0, 1, 2, or 3; each occurrence of the c 2 is independently selected from 0, 1, 2, 3, 4, or 5; each occurrence of the d 2 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of the e 2 is independently selected from 0, 1, 2, 3, or 4; each occurrence of the f 2 is independently selected from 0 or 1; each occurrence of the g 2 is independently selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of the h 2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8;
[0072] The Y is selected from an oxygen atom, a sulfur atom, or N-Ar 5 , and the Ar 5 is selected from one of 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring.
[0073] The R 2Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusing a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring.
[0074] Preferably, the Ar 3 is selected from one of the following groups:
[0075]
[0076]
[0077]
[0078]
[0079] wherein, the a 3 each occurrence is independently selected from 0, 1, 2, 3, 4 or 5; the b 3 each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c 3 each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d 3 each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the e 3 each occurrence is independently selected from 0, 1, 2 or 3; the f 3 each occurrence is independently selected from 0, 1, 2, 3 or 4; the g 3 each occurrence is independently selected from 0, 1 or 2; the h 3 each occurrence is independently selected from 0, 1, 2, 3, 4, 5 or 6; the i 3 each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the j 3 each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the k 3 each occurrence is independently selected from 0 or 1;
[0080] The Y 1 is selected from an oxygen atom, a sulfur atom, CR 31 R 32 or NR 33 , the R31 , R 32 , R 33 is independently selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, or the R 31 , R 32 can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 ring;
[0081] The R 34 is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0082] The Y 2 is selected from O, S or NR 35 , and the R 35 is selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0083] The R 3 each time it appears, is the same or different and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0084] The R 3 ' each time it appears, is the same or different and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted silyl group.
[0085] Preferably, the Ar 4 , Ar 5, Ar 201 , Ar 301 , Ar 501 , Ar 601 , R a , R b are independently selected from methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triphenylsilyl or one of the groups shown below, or the said R a , R b can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbocyclic ring:
[0086]
[0087]
[0088] The said a 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4 or 5; the said b 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the said c 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the said d 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the said e 41 is, each time it appears, the same or different and is selected from 0, 1, 2 or 3; the said f 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3 or 4; the said g 41 is, each time it appears, the same or different and is selected from 0, 1 or 2; the said h 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4, 5 or 6; the said i 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said j 41 is, each time it appears, the same or different and is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
[0089] , the said R 41Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0090] The aforementioned R 42 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;
[0091] The aforementioned X 1 Selected from O, S, CR 43 R 44 Or NR 45 The aforementioned R 43 R 44 R 45 Are independently selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, or the aforementioned R 43 R 44 Can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 ring;
[0092] The aforementioned R 46 Is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0093] The aforementioned X 2 Is selected from O, S or NR 47 The aforementioned R 47 Is selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring.
[0094] Preferably, the R 41 Each time it occurs, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, silyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl.
[0095] Preferably, the R 41 Each occurrence is identically or differently selected from one of the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tri-tert-butylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group, a phenyldiphenylsilyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a benzocyclopropyl group, a benzocyclobutane group, a benzocyclopentane group, a benzocyclohexane group, a benzocycloheptyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, and an isoquinolyl group.
[0096] Preferably, the R 3 '、R 42 Each time it occurs, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, and silyl.
[0097] Preferably, the R 3 '、R 42 Each time it occurs, it is identically or differently selected from one of the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, and a tri-tert-butylsilyl group.
[0098] Preferably, the R 31 , R 32 , R 33 , R43 , R 44 , R 45 Each time it appears, it is independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, silyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, fluorenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, or the R 31 , R 32 are linked to form a ring, or the R 43 , R 44 are linked to form a ring.
[0099] Preferably, the R 31 , R 32 , R 33 , R 43 , R 44 , R 45 Each time it appears, it is independently selected from methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldiphenylsilyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, or the R 31 , R 32 are linked to form a ring, or the R 43 , R 44 are linked to form a ring.
[0100] Preferably, the R 34 , R 46Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, silyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl.
[0101] Preferably, the R 34 , R 46 Each occurrence is identically or differently selected from one of methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldiphenylsilyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyridyl, pyrimidinyl, quinolyl and isoquinolyl.
[0102] Preferably, the R 35 , R 47 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, silyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl.
[0103] Preferably, the R 35 , R 47Each occurrence is independently selected from methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldiphenylsilyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, which may be the same or different each time it appears.
[0104] Preferably, the R, R 1 , R 2 , R 3 Each occurrence is independently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, silyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, fluorenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, which may be the same or different each time it appears.
[0105] Preferably, the R, R 1 , R 2 , R 3 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldiphenylsilyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, which may be the same or different each time it appears.
[0106] Preferably, the L 1 , L 2 , L 3 are independently selected from a single bond, a group as shown below, or a combination thereof:
[0107]
[0108] The a101 Each occurrence is independently selected from 0, 1, 2, 3 or 4; said b 101 Each occurrence is independently selected from 0, 1, 2 or 3; said c 101 Each occurrence is independently selected from 0, 1 or 2; said d 101 Each occurrence is independently selected from 0, 1, 2, 3, 4, 5 or 6; said e 101 Each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f 101 Each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
[0109] Said R 101 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0110] Said R 102 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group.
[0111] Preferably, said L 4 L 201 L 301 L 401 L 501 L 601 Are independently selected from a single bond, a group as shown below, or a combination thereof:
[0112]
[0113] Said a 401 Each occurrence is independently selected from 0, 1, 2, 3 or 4; said b 401 Each occurrence is independently selected from 0, 1, 2 or 3; said c 401 Each occurrence is independently selected from 0, 1 or 2; said d 401 Each occurrence is independently selected from 0, 1, 2, 3, 4, 5 or 6; said e 401Each occurrence is the same as or different from and is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said f 401 Each occurrence is the same as or different from and is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
[0114] the said R 401 Each occurrence is the same as or different from and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring;
[0115] the said R 402 Each occurrence is the same as or different from and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group.
[0116] Preferably, the said R 101 and R 401 Each occurrence is the same as or different from and is selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, silyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, fluorenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl.
[0117] Preferably, the said R 101 and R 401 Each occurrence is the same as or different from and is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldiphenylsilyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl.
[0118] Preferably, the R 102 , R 402 Each time it occurs, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, and silyl.
[0119] Preferably, the R 102 , R 402 Each time it occurs, it is identically or differently selected from one of the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, and a tri-tert-butylsilyl group.
[0120] Preferably, the first compound is selected from one of the following compounds:
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143] Preferably, the second compound is selected from one of the following compounds:
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164] Preferably, the second compound is selected from one of the following compounds:
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180] Preferably, based on the total mass of the first compound and the second compound, the mass percentage of the first compound is 1-99%, preferably 1%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 99%, and more preferably 30-70%.
[0181] The first compound represented by formula (I) of the present invention can be prepared by one of the following synthetic routes:
[0182] Synthetic route 1:
[0183]
[0184] Synthetic route 2:
[0185]
[0186] Synthetic route 3:
[0187]
[0188] Synthetic route 4:
[0189]
[0190] Synthetic route 5:
[0191]
[0192] Synthetic route 6:
[0193]
[0194] In the above synthetic routes, the said Ar 1 、Ar 2 、Ar 3 、L 1 、L 2 、L 3 are all as described in the present invention.
[0195] One of the above-mentioned Q 1 、Q 2 is selected from a chlorine atom, a bromine atom or an iodine atom, and the other is selected from B(OH) 2 or
[0196] In each of the above synthetic routes, the compound (y1) and the compound (y2) can obtain the first compound shown in formula (I) through a C-C coupling reaction.
[0197] Each of the above synthetic routes adopts reaction types commonly used in organic synthesis, and there are no particular restrictions on the reaction conditions (for example, the selection, dosage, and addition sequence and method of reaction solvents, catalysts, ligands, bases, etc.). The raw materials for the above preparation method are easily available, the preparation process is simple, and the yield is excellent. The present invention can also be synthesized using other conventional reaction types in organic synthesis without particular restrictions. The above is only an example of the synthetic route.
[0198] The hole transport region described in the present invention includes at least one of a hole injection layer, a hole transport layer, and a light-emission assisting layer. Preferably, the hole transport region includes a hole injection layer and a hole transport layer. The hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emission assisting layer. The hole injection layer is located between the anode and the light-emitting layer, the hole transport layer is located between the hole injection layer and the light-emitting layer, and the light-emission assisting layer is located between the hole transport layer and the light-emitting layer.
[0199] The hole injection layer described in the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, [n]cumulene compounds, and other substances with high hole injection properties can be used. For example, 4,4',4”-tris[2-(naphthalen-1-yl)phenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT-17, compounds p-1 to p-3, but not limited thereto.
[0200]
[0201] The hole transport layer described in the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds can be used, or other substances with a hole mobility of 10 -6 cm 2 / Vs or more can be used. For example, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(naphthalen-1-yl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), compounds HT-1 to HT-17 as shown above, but not limited thereto.
[0202] The light-emitting auxiliary layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives can be used, and other substances with appropriate HOMO and T1 energy levels can also be used. Examples include TPD, NPB, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl-N4'-[1,1':4',1''-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenz[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, compounds HT-1 to HT-17 as shown above, but not limited thereto.
[0203] The light-emitting layer described in the present invention includes a guest material and a host material, and a double-host material formed by using two host materials can be used. Fluorescent compounds such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. can be used as the guest material. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolvinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials such as iridium complexes, osmium complexes, platinum complexes and other metal complexes can also be used. Examples include bis(4,6-difluorophenylpyridine-N,C2)picolyliridium(III) (FIrpic), tris(2-phenylpyridine)iridium(III) (Ir(ppy) 3 ), bis(2-phenylpyridine)iridium(III) acetylacetonate (Ir(ppy) 2 (acac)), etc. The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material, such as metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives, benzoxazole derivatives, benzothiazole derivatives or benzimidazole derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives. Examples include Alq 3, BAlq, TPBI, TPD, 4,4'-bis(9-carbazolyl)biphenyl (CBP), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), 9,10-bis(2-naphthyl)anthracene (ADN), the compound shown in formula (I), the compound shown in formula (II), the compound shown in formula (III), but not limited thereto.
[0204] The electron transport region described in the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. Preferably, the electron transport region includes an electron injection layer and an electron transport layer. The electron injection layer is located between the cathode and the light-emitting layer, and the electron transport layer is located between the electron injection layer and the light-emitting layer. Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer. The electron injection layer is located between the cathode and the light-emitting layer, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.
[0205] The electron injection layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. One or more of the following substances can be selected: 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, other substances with high electron injection properties. Examples can include Li, Ca, Sr, LiF, CsF, CaF 2 , BaO, Li 2 CO 3 , CaCO 3 , Li 2 C 2 O 4 , Cs 2 C 2 O 4 , CsAlF 4 , LiOx, Yb, Tb, etc., but not limited thereto.
[0206] The electron transport layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, etc. with high electron transport properties can be used. Examples can include tris(8-hydroxyquinoline)aluminum (Alq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (BeBq 2) (bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq)), 2-(4-biphenylyl)-5-phenyloxadiazole (PBD), but not limited thereto.
[0207] The hole blocking layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The selected material is required to have a T1 energy level higher than that of the light-emitting layer, so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material should be lower than that of the host material of the light-emitting layer to play a role in blocking holes. Further, the electron mobility of the hole blocking layer material used is above 10 -6 cm 2 / Vs, which is conducive to the transmission of electrons. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, high molecular compounds, etc. Examples can include 1,3,5-tris(1-phenyl-1H-benzoimidazol-2-yl)benzene (TPBI), BAlq, etc., but not limited thereto.
[0208] The anode described in the present invention can be a reflective anode, such as a reflective film formed by silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb) or their alloys, or a layer structure that is highly work function and transparent or semi-transparent, such as indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In 2 O 3 ) or tin oxide (SnO 2 ) formed layer structure, specifically determined according to the type of device to be prepared. For example, if the device to be prepared is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be made. If the device to be prepared is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be made.
[0209] The cathode described in the present invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. A reflective electrode, a transparent electrode or a semi-transparent electrode can be made by adjusting the thickness of the film. If a bottom-emitting device needs to be prepared, a reflective cathode needs to be made. If a top-emitting device needs to be prepared, a transparent or semi-transparent cathode needs to be made.
[0210] Preferably, the organic electroluminescent device further includes a covering layer on the side of the cathode facing away from the anode.
[0211] The covering layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The covering layer material can use organic or inorganic substances with appropriate refractive indices. For example, it can be metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic hydrocarbon compounds, heteroaromatic hydrocarbon compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF 2 、CaF 2 、CsCl、CuI、V 2 O 5 、WO 3 、MoO 3 、TiO 2 、ZrO, ZnO, SiO 2 、SiN, ZnS, Alq 3 、Compound CP-1, Compound CP-2, Compound CP-3, Compound CP-4, but not limited thereto.
[0212]
[0213] Each of the above-mentioned organic layers, the cathode, and the anode can be prepared by any one of the methods such as vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc. There is no special limitation on the film thickness of each layer, as long as good device performance can be obtained.
[0214] Each of the above-mentioned organic layers is preferably prepared by vacuum evaporation, inkjet printing or spin coating.
[0215] The thickness of each of the above-mentioned organic layers is usually 5 nm to 100 μm, preferably 10 nm to 200 nm. The thicknesses of the anode and the cathode are adjusted according to the required transparency.
[0216] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display. Specifically, it can be listed as smartphone displays, tablet computer displays, smart wearable device displays, large-size displays such as televisions, VR, and automobile tail lights, etc.
[0217] The technical solutions and technical effects of the present invention will be further described below with reference to examples and comparative examples.
[0218] The mass spectrometry of the compounds of the present invention uses a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK, with chloroform as the solvent;
[0219] Elemental analysis uses a Vario EL cube type organic elemental analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.
[0220] Synthesis Example 1: Synthesis of Compound I-217
[0221]
[0222] Under nitrogen protection, add I-A-217 (2.87 g, 10 mmol), I-B-217 (5.76, 10 mmol), Pd(PPh 3 ) 4 (0.05 g, 0.04 mmol), aqueous potassium carbonate solution (2.9 g, 21 mmol), and toluene (65 mL) to the reaction flask, and reflux for 7 hours. After the reaction is completed, cool to room temperature, quench the reaction with water, extract with dichloromethane, combine the organic phases, dry the organic phases with anhydrous magnesium sulfate, filter, evaporate the filtrate under reduced pressure, and recrystallize from toluene to obtain Compound I-217 (5.39 g, yield 73%); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 737.1945 (theoretical value: 737.1959). Theoretical elemental content (%) C 50 H 31 N 3 S 2 : C, 81.38; H, 4.23; N, 5.69. Measured elemental content (%): C, 81.37; H, 4.26; N, 5.67.
[0223] Synthesis Example 2: Synthesis of Compound I-263
[0224]
[0225] Replace I-A-217 with an equimolar amount of I-A-263, replace I-B-217 with an equimolar amount of I-B-263, and the other steps are the same as those in Synthesis Example 1 to obtain Compound I-263 (4.96 g, yield 75%), and the solid purity detected by HPLC is ≧ 99.94%. Mass spectrometry m / z: 661.1664 (theoretical value: 661.1646). Theoretical elemental content (%) C 44 H 27 N 3 S 2 : C, 79.85; H, 4.11; N, 6.35. Measured elemental content (%): C, 79.88; H, 4.13; N, 6.31.
[0226] Synthesis Example 3: Synthesis of Compound I-292
[0227]
[0228] Replace I-A-217 with an equimolar amount of I-A-292 and I-B-217 with an equimolar amount of I-B-292. All other steps are the same as in Synthesis Example 1, and then Compound I-292 (4.91 g, yield 78%) can be obtained. The solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 629.2119 (theoretical value: 629.2103). Theoretical elemental content (%) C 44 H 27 N 3 O 2 : C, 83.92; H, 4.32; N, 6.67. Measured elemental content (%): C, 83.94; H, 4.33; N, 6.64.
[0229] Synthesis Example 4: Synthesis of Compound I-299
[0230]
[0231] Replace I-A-217 with an equimolar amount of I-A-299 and I-B-217 with an equimolar amount of I-B-299. All other steps are the same as in Synthesis Example 1, and then Compound I-299 (4.91 g, yield 76%) can be obtained. The solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 645.1889 (theoretical value: 645.1875). Theoretical elemental content (%) C 44 H 27 N 3 OS: C, 81.84; H, 4.21; N, 6.51. Measured elemental content (%): C, 81.81; H, 4.20; N, 6.54.
[0232] Synthesis Example 5: Synthesis of Compound I-331
[0233]
[0234] Replace I-A-217 with an equimolar amount of I-A-331 and I-B-217 with an equimolar amount of I-B-263. All other steps are the same as in Synthesis Example 1, and then Compound I-331 (4.96 g, yield 75%) can be obtained. The solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 661.1632 (theoretical value: 661.1646). Theoretical elemental content (%) C 44 H 27 N 3 S 2 : C, 79.85; H, 4.11; N, 6.35. Measured elemental content (%): C, 79.83; H, 4.13; N, 6.34.
[0235] Synthesis Example 6: Synthesis of Compound I-490
[0236]
[0237] Replace I-B-217 with an equimolar amount of I-B-490, and keep other steps the same as those in Synthesis Example 1, then Compound I-490 (4.30 g, yield 68%) can be obtained. The solid purity detected by HPLC is ≥ 99.91%. Mass spectrometry m / z: 632.1971 (theoretical value: 632.1961). Theoretical elemental content (%) C 41 H 24 N 6 O 2 : C, 77.84; H, 3.82; N, 13.28. Measured elemental content (%): C, 77.83; H, 3.84; N, 13.25.
[0238] Synthesis Example 7: Synthesis of Compound I-528
[0239]
[0240] Replace I-A-217 with an equimolar amount of I-A-528, and replace I-B-217 with an equimolar amount of I-B-528. Keep other steps the same as those in Synthesis Example 1, then Compound I-528 (4.94 g, yield 70%) can be obtained. The solid purity detected by HPLC is ≥ 99.92%. Mass spectrometry m / z: 705.2433 (theoretical value: 705.2416). Theoretical elemental content (%) C 50 H 31 N 3 O 2 : C, 85.09; H, 4.43; N, 5.95. Measured elemental content (%): C, 85.07; H, 4.45; N, 5.94.
[0241] Synthesis Example 8: Synthesis of Compound I-535
[0242]
[0243] Replace I-A-217 with an equimolar amount of I-A-535, and replace I-B-217 with an equimolar amount of I-B-535. Keep other steps the same as those in Synthesis Example 1, then Compound I-535 (4.71 g, yield 67%) can be obtained. The solid purity detected by HPLC is ≥ 99.91%. Mass spectrometry m / z: 702.2321 (theoretical value: 702.2307). Theoretical elemental content (%) C 51 H 30 N 2 O 2: C, 87.16; H, 4.30; N, 3.99. Measured elemental content (%): C, 87.15; H, 4.34; N, 3.96.
[0244] Synthesis Example 9: Synthesis of Compound 565
[0245]
[0246] Under nitrogen protection, to the reaction flask were successively added toluene (375 ml), I-a-565 (6.76 g, 25 mmol), I-b-565 (11.95 g, 50 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), sodium tert-butoxide (9.6 g, 100 mmol) and BINAP (0.6 g, 1 mmol). The mixture was stirred and heated under reflux for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. Recrystallization was carried out with toluene / methanol (volume ratio 9:1) to obtain Intermediate I-B-565 (9.98 g, yield 80%). The purity of the solid was detected by HPLC to be ≥99.93%. Mass spectrometry m / z: 498.1152 (theoretical value: 498.1135).
[0247] Under nitrogen protection, to the reaction flask were added I-A-565 (2.91 g, 10 mmol), I-B-565 (4.99 g, 10 mmol), Pd(PPh 3 ) 4 (0.05 g, 0.04 mmol), aqueous potassium carbonate solution (2.90 g, 21 mmol), and toluene (65 mL). The mixture was refluxed for 7 hours. After the reaction was completed, it was cooled to room temperature, the reaction was quenched with water, and the mixture was extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated. Recrystallization was carried out with toluene to obtain Compound I-565 (5.25 g, yield 74%); HPLC purity ≥99.91%. Mass spectrometry m / z: 709.2686 (theoretical value: 709.2667). Theoretical elemental content (%) C 50 H 27 D 4 N 3 O 2 : C, 84.60; H, 4.97; N, 5.92. Measured elemental content (%): C, 84.63; H, 4.95; N, 5.91.
[0248] Synthesis Example 10: Synthesis of Compound 567
[0249]
[0250] Under nitrogen protection, toluene (250 ml), I-a-567 (5.79 g, 25 mmol), I-b-567 (4.18 g, 25 mmol), Pd 2 (dba) 3 (0.23 g, 0.25 mmol), sodium tert-butoxide (4.8 g, 50 mmol) and BINAP (0.3 g, 0.5 mmol) were successively added to the reaction flask, and the mixture was stirred and heated under reflux for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. Recrystallization was carried out with toluene / methanol (volume ratio 9:1) to obtain intermediate I-B-567 (6.52 g, yield 82%), and the purity of the solid detected by HPLC was ≧99.94%. Mass spectrometry m / z: 317.0979 (theoretical value: 317.0971).
[0251] Under nitrogen protection, I-A-567 (3.56 g, 10 mmol), I-B-567 (3.18 g, 10 mmol), Pd(PPh 3 ) 4 (0.05 g, 0.04 mmol), aqueous potassium carbonate (2.90 g, 21 mmol) solution, and toluene (65 mL) were added to the reaction flask and refluxed for 7 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The combined organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated. Recrystallization was carried out with toluene to obtain compound I-567 (4.22 g, 71%); HPLC purity ≥99.92%. Mass spectrometry m / z: 593.2123 (theoretical value: 593.2103). Theoretical elemental content (%) C 41 H 27 N 3 O 2 : C, 82.95; H, 4.58; N, 7.08. Measured elemental content (%): C, 82.96; H, 4.59; N, 7.05.
[0252] Synthesis Example 11: Synthesis of Compound I-568
[0253]
[0254] Replace I-A-217 with an equimolar amount of I-A-568 and replace I-B-217 with an equimolar amount of I-B-292. All other steps are the same as in Synthesis Example 1, then compound I-568 (4.35 g, yield 72%) can be obtained. The solid purity detected by HPLC is ≧99.93%. Mass spectrometry m / z: 603.1931 (theoretical value: 603.1947). Theoretical elemental content (%) C 42 H 25 N 3 O 2 : C, 83.56; H, 4.17; N, 6.96. Measured elemental content (%): C, 83.53; H, 4.18; N, 6.97.
[0255] Synthesis Example 12: Synthesis of Compound I-576
[0256]
[0257] Replace I-A-217 with an equimolar amount of I-A-576 and replace I-B-217 with an equimolar amount of I-B-576. All other steps are the same as in Synthesis Example 1, then compound I-576 (4.36 g, yield 74%) can be obtained. The solid purity detected by HPLC is ≧99.94%. Mass spectrometry m / z: 588.2210 (theoretical value: 588.2202). Theoretical elemental content (%) C 42 H 25 N 3 O 2 : C, 87.73; H, 4.79; N, 4.76. Measured elemental content (%): C, 87.76; H, 4.77; N, 4.75.
[0258] Synthesis Example 13: Synthesis of Compound I-579
[0259]
[0260] Replace I-A-217 with an equimolar amount of I-A-579 and replace I-B-217 with an equimolar amount of I-B-292. All other steps are the same as in Synthesis Example 1, then compound I-579 (4.72 g, yield 75%) can be obtained. The solid purity detected by HPLC is ≧99.92%. Mass spectrometry m / z: 629.2121 (theoretical value: 629.2103). Theoretical elemental content (%) C 44 H 27 N 3 O 2 : C, 83.92; H, 4.32; N, 6.67. Measured elemental content (%): C, 83.93; H, 4.36; N, 6.64.
[0261] Synthesis Example 14: Synthesis of Compound I-592
[0262]
[0263] Replace I-A-217 with an equimolar amount of I-A-592, replace I-B-217 with an equimolar amount of I-B-263, and keep other steps the same as in Synthesis Example 1, then Compound I-592 (4.77 g, yield 72%) can be obtained. The solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 661.1636 (theoretical value: 661.1646). Theoretical elemental content (%) C 44 H 27 N 3 S 2 : C, 79.85; H, 4.11; N, 6.35. Measured elemental content (%): C, 79.84; H, 4.15; N, 6.32.
[0264] Synthesis Example 15: Synthesis of Compound I-613
[0265]
[0266] Replace I-A-217 with an equimolar amount of I-A-613, replace I-B-217 with an equimolar amount of I-B-292, and keep other steps the same as in Synthesis Example 1, then Compound I-613 (4.69 g, yield 70%) can be obtained. The solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 669.2431 (theoretical value: 669.2416). Theoretical elemental content (%) C 47 H 31 N 3 O 2 : C, 84.28; H, 4.67; N, 6.27. Measured elemental content (%): C, 84.27; H, 4.69; N, 6.25.
[0267] Synthesis Example 16: Synthesis of Compound I-614
[0268]
[0269] Replace I-A-217 with an equimolar amount of I-A-579, replace I-B-217 with an equimolar amount of I-B-614, and keep other steps the same as in Synthesis Example 1, then Compound I-614 (4.37 g, yield 69%) can be obtained. The solid purity detected by HPLC is ≥99.91%. Mass spectrometry m / z: 632.1978 (theoretical value: 632.1961). Theoretical elemental content (%) C 41 H 24 N6 O 2 : C, 77.84; H, 3.82; N, 13.28. Measured elemental content (%): C, 77.82; H, 3.83; N, 13.26.
[0270] Synthesis Example 17: Synthesis of Compound I-615
[0271]
[0272] Replace I-A-217 with an equimolar amount of I-A-615, and replace I-B-217 with an equimolar amount of I-B-615. All other steps are the same as in Synthesis Example 1, then Compound I-615 (4.71 g, yield 71%) can be obtained. The solid purity detected by HPLC is ≧99.92%. Mass spectrometry m / z: 662.1580 (theoretical value: 662.1599). Theoretical elemental content (%) C 43 H 26 N 4 S 2 : C, 77.92; H, 3.95; N, 8.45. Measured elemental content (%): C, 77.93; H, 3.97; N, 8.44.
[0273] The following are other compounds used in the device preparation examples except for the first compound shown in formula (I) and the second compound shown in formula (II) or formula (III) of the present invention:
[0274]
[0275] A combined IVL test system is composed of a test software, a computer, a K2400 digital source meter from Keithley Instruments, Inc. in the United States, and a PR788 spectral scanning luminance meter from Photo Research, Inc. in the United States. At atmospheric pressure and room temperature, the device prepared by the present invention is tested for luminous efficiency, driving voltage, etc. at a current density of 15 mA / cm 2 At this time. The lifetime (luminance decays to 95% of the initial luminance) of the device prepared by the present invention is tested using the M6000 OLED lifetime test system from McScience Co., Ltd. at atmospheric pressure and room temperature. The test results are shown in Table 1.
[0276] Comparative Device Preparation Example 1: Comparative Device 1
[0277] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned with deionized water twice for 20 minutes each time, then ultrasonically cleaned with isopropanol, acetone, and methanol for 20 minutes each in turn, then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
[0278] The following layers are sequentially evaporated on the above ITO / Ag / ITO glass substrate: a. HT-12 and p-1 (mass ratio 100:1) as the hole injection layer, with a thickness of 10 nm; b. HT-2 as the hole transport layer, with a thickness of 120 nm; c. HT-10 as the light-emitting auxiliary layer, with a thickness of 10 nm; d. Compound I-292 and Ir(dpm)PQ 2 (mass ratio 94:6) as the light-emitting layer, with a thickness of 20 nm; e. TPBi as the hole blocking layer, with a thickness of 5 nm; f. BCP and Liq (mass ratio 5:5) as the electron transport layer, with a thickness of 30 nm; g. LiF as the electron injection layer, with a thickness of 1 nm; h. Mg and Ag (mass ratio 1:9) as the cathode, with a thickness of 15 nm; h: CP-4 as the capping layer, with a thickness of 70 nm.
[0279] Comparative device preparation examples 2 to 15: Comparative devices 2 to 15
[0280] Replace compound I-292 in the light-emitting layer with the following compounds respectively: I-528, I-565, I-579, I-592, I-614, II-12, II-35, II-81, II-272, III-272, III-324, III-387, III-443, III-585. Other steps are the same as those in Comparative device preparation example 1, and Comparative devices 2 to 15 can be obtained.
[0281] Comparative device preparation example 16: Comparative device 16
[0282] Replace compound I-292 in the light-emitting layer with compound RH and compound II-35, and their mass ratio to Ir(dpm)PQ 2 is 47:47:6. Other steps are the same as those in Comparative device preparation example 1, and Comparative device 16 can be obtained.
[0283] Comparative device preparation examples 17 to 23: Comparative devices 17 to 23
[0284] Replace compound II-35 in the light-emitting layer with the following compounds respectively: II-81, II-272, III-272, III-324, III-387, III-443, III-585. Other steps are the same as those in Comparative device preparation example 16, and Comparative devices 17 to 23 can be obtained.
[0285] Device preparation examples 1 to 41: Light-emitting devices 1 to 41
[0286] Replace the compounds RH and II-35 in the light-emitting layer with the following combinations of compounds: I-11 and II-93, I-217 and II-509, I-263 and II-447, I-292 and II-81, I-331 and II-12, I-490 and II-128, I-565 and II-35, I-567 and II-439, I-568 and II-499, I-576 and II-272, I-579 and II-81, I-579 and II-272, I-592 and II-93, I-592 and II-128, I-613 and II-482, I-614 and II-81, I-615 and II-35, I-142 and III-174, I-292 and III-495, I-292 and III-585, I-299 and III-7, I-331 and III-272, I-331 and III-615, I-490 and III-481, I-528 and III-233, I-535 and III-348, I-565 and III-324, I-565 and III-444, I-567 and III-639, I-568 and III-444, I-579 and III-272, I-579 and III-387, I-579 and III-443, I-592 and III-324, I-592 and III-443, I-613 and III-481, I-614 and III-542, I-614 and III-387, I-614 and III-585, I-615 and III-443, I-615 and III-495. The other steps are the same as those in Comparative Device Preparation Example 17, and thus light-emitting devices 1 to 41 can be obtained.
[0287] Table 1
[0288]
[0289]
[0290]
[0291] The device data in Table 1 show that for the organic electroluminescent device provided by the present invention, by selecting the first compound represented by formula (I) and the second compound represented by formula (II) or formula (III) as the dual host materials, the driving voltage of the device is reduced, the luminous efficiency of the device is improved, and the service life of the device is extended.
[0292] It should be noted that the present invention has been specifically described with individual embodiments. However, without departing from the principle of the present invention, those of ordinary skill in the art can make various improvements in the form or details of the present invention, and these improvements also fall within the protection scope of the present invention.
Claims
1. An organic electroluminescent device, comprising 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, wherein the light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the cathode and the light-emitting layer, and the light-emitting layer contains a first compound and a second compound, characterized in that: The first compound has a structure shown in formula (I), and the second compound has a structure shown in formula (II) or formula (III): Each time X appears, it is selected from CR or nitrogen atoms, the same or different, and at least three of them are carbon atoms connected to L1, L2, and L3; The Ar1 is selected from one of the following groups: Wherein, each time a1 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time b1 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; The Ar2 is selected from one of the following groups: Wherein, the Y is selected from oxygen atom, sulfur atom or N-Ar5; The Ar3 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C12 aliphatic ring fused with a C6-C30 aromatic ring, and the Ar3 is not selected from a substituted or unsubstituted triazine group; The Z1 and Z2 are independently selected from a single bond, O, S, CR a R b or NL 601 -Ar 601 , and at least one of them is not a single bond; The Ar4, Ar5, Ar 201 ,Ar 301 ,Ar 501 ,Ar 601 , R a , R b independently selected from 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, a substituted or unsubstituted C3-C12 aliphatic ring fused with a C6-C30 aromatic ring, or the R a , R b Can bond to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbon ring; The ring C, ring E, ring F, ring G, ring H, ring I, ring J, and ring K are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, or a ring formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time when R, R1, and R2 appear, they are identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, a substituted or unsubstituted benzofuranyl group, and a substituted or unsubstituted benzothiophenyl group; The L4 and L 201 , L 301 , L 401 , L 501 , L 601 One independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a divalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.
2. The organic electroluminescent device according to claim 1, characterized in that: The ring C, ring E, ring F, ring G, ring H, ring I, ring J, and ring K are independently selected from one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, fluorene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring, benzocyclopropane ring, benzocyclobutane ring, benzocyclopentane ring, benzocyclohexane ring, and benzocycloheptane ring.
3. The organic electroluminescent device according to claim 1, characterized in that: The Ar2 is selected from one of the following groups: wherein each time a2 appears, it is selected from 0, 1 or 2 in the same or different manner; each time b2 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time c2 appears, it is selected from 0, 1, 2, 3, 4 or 5 in the same or different manner; each time d2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6 or 7 in the same or different manner; each time e2 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time f2 appears, it is selected from 0 or 1 in the same or different manner; each time g2 appears, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time h2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; The Y is selected from an oxygen atom, a sulfur atom or N-Ar5, and the Ar5 is selected from 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, a substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time R2 appears, it is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.
4. The organic electroluminescent device according to claim 1, characterized in that: The Ar3 is selected from one of the following groups: wherein each time a3 appears, it is selected from 0, 1, 2, 3, 4 or 5 in the same or different manner; each time b3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6 or 7 in the same or different manner; each time c3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9 in the same or different manner; each time d3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11 in the same or different manner; each time e3 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time f 3 is selected from 0, 1, 2, 3 or 4 at each occurrence; g3 is selected from 0, 1 or 2 at each occurrence; h3 is selected from 0, 1, 2, 3, 4, 5 or 6 at each occurrence; i3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 at each occurrence; j3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 at each occurrence; k3 is selected from 0 or 1 at each occurrence; The Y1 is selected from oxygen atom, sulfur atom, CR 31 R 32 or NR 33 , the R 31 , R 32 , R 33 independently selected from 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, a substituted or unsubstituted C3-C12 aliphatic ring fused with a C6-C30 aromatic ring, or the R 31 , R 32 Can bond to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 ring; The R 34 One selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The Y2 is selected from O, S or NR 35 , the R 35 One selected from 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, and a monovalent group formed by condensation of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time the R3 appears, it is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring with a C6-C30 aromatic ring; Each occurrence of R3' is identically or differently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group.
5. The organic electroluminescent device according to claim 1, characterized in that: The Ar4, Ar5, Ar 201 ,Ar 301 ,Ar 501 ,Ar 601 , R a , R b independently selected from methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triphenylsilyl or one of the groups shown below, or said R a , R b Can bond to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbon ring: The a 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said e 41 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 41 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said g 41 Each time it occurs, it is selected from 0, 1 or 2 identically or differently; 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said i 41 Each time it occurs, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the same or different; 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 41 Each occurrence is the same or different one selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R 42 Each occurrence is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group; The X1 is selected from O, S, CR 43 R 44 or NR 45 , the R 43 , R 44 , R 45 independently selected from 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, a substituted or unsubstituted C3-C12 aliphatic ring fused with a C6-C30 aromatic ring, or the R 43 , R 44 Can bond to each other to form a substituted or unsubstituted saturated or unsaturated C3-C10 ring; The R 46 One selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The X2 is selected from O, S or NR 47 , the R 47 One selected from 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, and a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.
6. The organic electroluminescent device according to claim 1, characterized in that: The L1, L2, and L3 are independently selected from a single bond, the following groups, or a combination thereof: The a 101 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 101 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 101 Each occurrence is identically or differently selected from 0, 1 or 2; said d 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 101 Each occurrence is the same or different one selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R 102 Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group.
7. The organic electroluminescent device according to claim 1, characterized in that: The L4 and L 201 , L 301 , L 401 , L 501 , L 601 Independently selected from a single bond, a group as shown below, or a combination thereof: The a 401 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 401 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 401 Each occurrence is identically or differently selected from 0, 1 or 2; said d 401 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 401 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f 401 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 401 Each occurrence is the same or different one selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R 402 Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group.
8. The organic electroluminescent device according to claim 1, characterized in that: The first compound is selected from one of the following compounds:
9. The organic electroluminescent device according to claim 1, characterized in that: The second compound is selected from one of the following compounds:
10. The organic electroluminescent device according to claim 1, characterized in that: The second compound is selected from one of the following compounds: