Compound containing thick furan and organic electroluminescent device thereof
By using condensed furan compounds as both the capping layer and the host material, the problems of light extraction efficiency and stability in existing organic electroluminescent devices have been solved, resulting in higher luminous efficiency and longer lifespan.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- CHANGCHUN HYPERIONS TECH CO LTD
- Filing Date
- 2026-02-10
- Publication Date
- 2026-05-19
AI Technical Summary
Existing organic electroluminescent devices suffer from low light extraction efficiency and insufficient stability in their capping layer materials, as well as inadequate energy levels in the main material, which negatively impacts device performance.
Compounds containing condensed furan are used as both the capping and host materials, and energy level matching is optimized to improve energy transfer efficiency and stability.
It effectively reduces total internal reflection loss and waveguide loss, improves luminous efficiency, extends device lifespan, and enhances device performance.
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Abstract
Description
Technical Field
[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a compound containing condensed furan and its organic electroluminescent device. Background Technology
[0002] Since achieving a key breakthrough in the 1980s, OLED technology has moved from the laboratory to large-scale commercial applications, becoming a core technology for next-generation display devices. Compared to traditional liquid crystal display technology, OLED devices are structurally stable, ultra-thin, and lightweight, and inherently possess flexible, foldable, and bendable characteristics, bringing revolutionary innovation to the form factor of end products. In addition, OLED also has advantages such as wide viewing angle, high color gamut, and the ability to be fabricated using low-temperature solution processes, establishing its leading position in the high-end display market and future flexible electronics.
[0003] Organic light-emitting diodes (OLEDs) are solid-state electroluminescent devices based on organic semiconductor materials. The essence of their light emission is the direct conversion of electrical energy into light energy. The light-emitting process is as follows: When a voltage is applied between the cathode and anode of the device, free electrons are generated on the cathode side, and holes are generated on the anode side. Electrons and holes are injected from the cathode and anode respectively, and migrate towards each other under the influence of an applied electric field. Electrons pass through the electron injection layer and transport layer, and holes pass through the hole injection layer and transport layer, eventually meeting and recombinating in the light-emitting layer to form excitons. The excited excitons return to the ground state through radiative relaxation, releasing their excess energy as photons, thus producing visible light. OLED devices are typically constructed using a finely stacked multilayer functional structure. A common device structure includes: a substrate, anode, hole injection layer, hole transport layer, light-emitting layer (usually composed of a host material and dopants), electron transport layer, electron injection layer, cathode, and an outermost capping layer. The material properties of each layer and the energy level matching between layers play a crucial role in the final performance of the device.
[0004] Among these, the capping layer (CPL) and the emissive layer (EML) are two crucial core materials, whose performance directly determines the device's efficiency and lifetime. The capping layer utilizes optical interference effects to modulate light output; the emissive layer's host material carries energy and efficiently transfers it to the doped luminescent guest. Its triplet energy level must be significantly higher than that of the dopant to effectively limit exciton energy backflow and prevent energy quenching. Its highest occupied molecular orbital (HOMO) / lowest unoccupied molecular orbital (LUMO) energy levels must match those of the adjacent transport layer to reduce the injection barrier. However, currently, traditional capping layer materials have light extraction efficiencies of only around 20%, insufficient refractive index, or poor stability under high-energy light illumination; and commonly used host materials suffer from insufficient energy levels. Therefore, developing novel capping layer and host materials has become a key focus of research in the industry. Summary of the Invention
[0005] To address the issue of low performance in existing organic electroluminescent devices, this invention provides a compound containing condensed furan and its organic electroluminescent device.
[0006] This invention provides a compound containing condensed furan, the compound having the structure shown in Formula I.
[0007] The Ar2 and Ar3 are independently selected from the following groups:
[0008]
[0009]
[0010]
[0011] X is selected from O or S; The v is independently selected from C (R2) or N, and when v is bonded to other groups, the v is selected from C atoms; The R2 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted silyl. The x is independently selected from C(R4) or N; The R4 is selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent R4s can be interconnected to form one or more substituted or unsubstituted C5 or more rings; The Ar1 is selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or any one of the following groups:
[0012]
[0013]
[0014] The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms; W1 is selected from O, S or N (Rz); Q1 is selected from O, S, N (Rz) or C (RxRy); The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings; The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings; The Rd1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; The L1 is selected from single bonds, substituted or unsubstituted C6~C30 arylene groups, substituted or unsubstituted C2~C30 heteroarylene groups, substituted or unsubstituted C3~C30 alicyclic and C6~C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3~C30 alicyclic and C2~C30 heteroaromatic rings with fused cycloyl groups. The L2 and L3 are independently selected from single bonds or any of the following groups:
[0015]
[0016] The u is independently selected from CH or N; The V is selected from O or S; The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rm is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, and substituted or unsubstituted silyl. The Rp and Rq are independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rp and Rq can be connected to each other to form substituted or unsubstituted rings; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6.
[0017] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode and / or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the compound containing condensed furan.
[0018] Beneficial effects: The compound containing condensed furan shown in Formula I provided by this invention, when used as a capping material in organic electroluminescent devices, can effectively reduce total internal reflection loss and waveguide loss in the device, and improve the luminous efficiency and lifespan of the device; when used as a host material, it can efficiently transfer energy to the doped light-emitting guest and has a suitable triplet energy level, giving the device excellent performance. Detailed Implementation
[0019] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.
[0020] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.
[0021] In this specification, " "This refers to the portion that is connected to another substituent."
[0022] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.
[0023] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent or ; Can represent , , And so on.
[0024] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.
[0025] The alkyl group described in this invention refers to a monovalent group obtained 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, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc., but are not limited thereto.
[0026] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.
[0027] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R... kThe same or different groups are selected from the following: 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 norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl" refers to a silyl group substituted with a substituted or unsubstituted C3-C25 alkyl or aryl group, preferably substituted with 3 alkyl or 3 aryl groups. Examples of “substituted or unsubstituted silyl groups”, especially “substituted or unsubstituted C3-C25 silyl groups”, may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, etc.
[0028] The aryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.
[0029] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, and preferably have 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a] ... Phinyl, o-phenanthroline, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiaazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.
[0030] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably with 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 7 carbon atoms. It can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropylene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.
[0031] The fused ring of aromatic and aliphatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused ring of aromatic and aliphatic rings can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.
[0032] The arylene group described in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, even more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the aforementioned arylene groups, monocyclic arylene groups can be phenylene, etc., but are not limited to these. The arylene group can be substituted or unsubstituted. Polycyclic arylene groups can be biphenylene, terphenylene, tetraphenylene, etc., but are not limited to these. Fused-ring arylene groups can be naphthylene, anthraceneene, phenanthrene, pyrene, fluorene, spirofluorene, triphenylene, perylene, fluorenyl, phenanthrene, etc., but are not limited to these.
[0033] The heteroaryl group described in this invention refers to the general term for a divalent group formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatoms can be one or more of N, O, S, Si, and P, and can be monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroaryl group can be substituted or unsubstituted. Examples may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, thiopheneyl, pyrroloyl, furanyl, pyranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, carbazolyl, benzocarbazolyl, acridineyl, imoxazanyl, thionazanyl, phenazinyl, phenthiazolyl, phenoxazinyl, indolyl, quinolinyl, isoquinolinyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, dibenzothiopheneyl, quinoxolinyl, quinoxolinyl, naphthinyl, purineyl, and phenanthrolineyl.
[0034] The fused ring groups of aromatic and aliphatic rings described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linking sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the fused ring groups of aromatic and aliphatic rings described above.
[0035] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.
[0036] The substituents described in "substituted or unsubstituted" in this invention may be the same as or different from each other, and are selected from deuterium, cyano, nitro, trifluoromethyl, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted Any one of the fused ring groups of C6-C30 aromatic rings and C3-C30 aliphatic rings, preferably deuterium, cyano, halogen atom, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C25 silyl, C6-C30 aryl, or C2-C30 heteroaryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. alkyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene, phenyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, Benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, pyrroleyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.
[0037] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below: .
[0038] In this specification, the rings formed by the linkage can be aromatic or non-aromatic rings, and can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited to these.
[0039] This invention provides a compound containing condensed furan, the compound having the structure shown in Formula I.
[0040] The Ar2 and Ar3 are independently selected from the following groups:
[0041]
[0042]
[0043]
[0044] X is selected from O or S; The v is independently selected from C (R2) or N, and when v is bonded to other groups, the v is selected from C atoms; The R2 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted silyl. The x is independently selected from C(R4) or N; The R4 is selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent R4s can be interconnected to form one or more substituted or unsubstituted C5 or more rings; The Ar1 is selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or any one of the following groups:
[0045]
[0046]
[0047] The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms; W1 is selected from O, S or N (Rz); Q1 is selected from O, S, N (Rz) or C (RxRy); The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings; The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings; The Rd1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; The L1 is selected from single bonds, substituted or unsubstituted C6~C30 arylene groups, substituted or unsubstituted C2~C30 heteroarylene groups, substituted or unsubstituted C3~C30 alicyclic and C6~C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3~C30 alicyclic and C2~C30 heteroaromatic rings with fused cycloyl groups. The L2 and L3 are independently selected from single bonds or any of the following groups:
[0048]
[0049] The u is independently selected from CH or N; The V is selected from O or S; The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rm is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, and substituted or unsubstituted silyl. The Rp and Rq are independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rp and Rq can be connected to each other to form substituted or unsubstituted rings; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6.
[0050] Preferably, Ar2 and Ar3 are independently selected from any one of the following structures.
[0051]
[0052]
[0053]
[0054]
[0055]
[0056]
[0057]
[0058]
[0059]
[0060]
[0061]
[0062]
[0063]
[0064]
[0065]
[0066]
[0067]
[0068]
[0069]
[0070]
[0071]
[0072]
[0073]
[0074]
[0075]
[0076]
[0077]
[0078]
[0079]
[0080]
[0081]
[0082]
[0083]
[0084]
[0085]
[0086]
[0087]
[0088]
[0089]
[0090]
[0091]
[0092]
[0093]
[0094]
[0095] R2 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthalene. alkyl, phenanthrene, phenylene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocyclopentane, benzocyclopentenyl, benzocycloheptane, benzocycloheptenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl; The b0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b1 is selected from 0, 1, or 2; the b2 is selected from 0, 1, 2, or 3; the b3 is selected from 0, 1, 2, 3, 4, 5, or 6; the b4 is selected from 0, 1, 2, 3, 4, or 5; the b5 is selected from 0, 1, 2, 3, or 4; the b6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. Preferably, the... Selected from any one of the following groups:
[0096]
[0097] X1 is selected from O, S, C (RsRr) or N (Rg); The x is independently selected from C(R4), or in each group, one, two, three, four, five, or six x are selected from N, and the rest are selected from C(R4). When x is bonded to other groups, the x is selected from C atoms. The R4 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rg is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rs and Rr are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. adamantyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or Rs and Rr can be interconnected to form one or more substituted or unsubstituted rings.
[0098] Preferably, the Ar1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, or any one of the structures shown below.
[0099]
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106]
[0107]
[0108]
[0109]
[0110]
[0111]
[0112]
[0113]
[0114]
[0115] The t is independently selected from CH, or one, two or three ts in each group are selected from N, and the rest are selected from CH. When t is bonded to other groups, the t is selected from C atoms. The Rz is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd1 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rds may be connected to each other to form one or more substituted or unsubstituted rings; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a7 is selected from 0, 1, 2, 3, 4, 5, or 6; a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; a 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; a 12 Select from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.
[0116] Preferably, when Ar2 is selected from one or more preferred groups derived from N, Ar1 is not selected from... (or a preferred group derived from this group).
[0117] Preferably, L1 is selected from a single bond or any of the structures shown below.
[0118]
[0119] The i is independently selected from CH or N; The Y is selected from O, S, or N (Re); The ring Q is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rt is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rt can be interconnected to form one or more substituted or unsubstituted rings; The Rt1 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted silyl. The Rp0 and Rq0 are independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rw and Rz can be connected to each other to form substituted or unsubstituted rings; The Re is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, and substituted or unsubstituted silyl. The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2 or 3; the t3 is selected from 0, 1 or 2; and the t4 is selected from 0, 1, 2, 3, 4, 5 or 6.
[0120] Preferably, L1 is selected from a single bond or any of the structures shown below.
[0121]
[0122]
[0123]
[0124]
[0125]
[0126] The Rt is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, benzocyclopropane. , benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocycloheptyl, benzocycloheptenyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophenyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, or two adjacent Rts may be linked together to form one or more substituted or unsubstituted rings; Rt1 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthalene. alkyl, phenanthrene, phenylene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocyclopentane, benzocyclopentenyl, benzocycloheptane, benzocycloheptenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl; The Re group is independently selected from hydrogen, deuterium, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, phenylenetriene. Benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocyclopentane, benzocyclopentenyl, benzocycloheptane, benzocycloheptenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl; The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2 or 3; the t3 is selected from 0, 1 or 2; the t4 is selected from 0, 1, 2, 3, 4, 5 or 6; the t5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and the t6 is selected from 0, 1, 2, 3, 4 or 5.
[0127] Preferably, when Selected from
[0128] In this case, Ar1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, and triphenylsilyl, and L1 is selected from single bonds.
[0129] Preferably, L2 and L3 are independently selected from single bonds or any of the structures shown below.
[0130]
[0131]
[0132]
[0133]
[0134]
[0135] The Rm is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, benzocyclopropane. Benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocycloheptyl, benzocycloheptenyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophenyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, or two adjacent Rm may be connected to each other to form one or more substituted or unsubstituted rings; Rm1 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthalene. alkyl, phenanthrene, phenylene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocyclopentane, benzocyclopentenyl, benzocycloheptane, benzocycloheptenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p6 is selected from 0, 1, 2, 3, 4 or 5.
[0136] Preferably, the compound containing condensed furan is selected from any one of the structures shown below;
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181]
[0182]
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225]
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232]
[0233]
[0234]
[0235]
[0236]
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265]
[0266]
[0267]
[0268]
[0269]
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286]
[0287]
[0288]
[0289]
[0290]
[0291]
[0292]
[0293]
[0294] .
[0295] The above lists some specific structural forms of compounds containing condensed furan represented by Formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula I, with substituents as defined above, should be included.
[0296] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode and / or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the compounds containing condensed furan described in the present invention.
[0297] Preferably, the organic functional layer is located between the anode and the cathode. The organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is located between the anode and the light-emitting layer. The light-emitting layer is located between the electron transport region and the hole transport region. The electron transport region is located between the light-emitting layer and the cathode. The light-emitting layer contains any one or more of the compounds containing condensed furan described in this invention.
[0298] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the host material comprises any one or more of the compounds containing condensed furan described in this invention.
[0299] Preferably, the organic functional layer is located outside either the anode or the cathode electrode, and the organic functional layer includes a capping layer, which contains any one or more of the compounds containing condensed furan described in this invention.
[0300] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below: The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged when forming electrodes or organic layers, such as glass, plastic, polymer films, silicon, etc.
[0301] The anode material described in this invention preferably uses a material with a high energy function, which improves hole injection efficiency. It can be selected from any one or more of the following structures: indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure comprising two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.
[0302] The hole injection layer described in this invention preferably uses a material with good hole-accepting ability. It can be selected from any one or more of the following structures: metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide; phthalocyanine compounds; benzidine compounds; phenazine compounds; etc., but is not limited thereto.
[0303] The hole-blocking layer of the present invention is preferably made of a material with good electron transport capability and hole-blocking capability. It can be selected from any one or more of the following structures: bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc., but is not limited thereto.
[0304] The electron transport layer described in this invention is preferably made of a material with good stability and high electron mobility. It can be selected from any one or more of the following structures: aluminum 8-hydroxyquinoline (Alq3), zinc(II) bis(8-hydroxyquinoline) (Znq), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3,3,5,5-tetra[m-pyridyl]benzene- [3-yl]biphenyl (BP4mPy), 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-phenyl)-1-phenyl)-1H-phenanthrene[9,10-d]imidazole (ADN-PAimi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl (BTB), etc., but not limited to these.
[0305] The light-emitting layer material described in this invention includes a host material and a doped material. The host material of the light-emitting layer needs to have bipolar charge transport properties and a suitable energy level. The material can be selected from any one or more of the following structures: 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-AND), N,N'-bis-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazole)benzene (TCP), etc. In addition to the above materials and combinations thereof, the main material of the luminescent layer may also include other known materials suitable for serving as the luminescent layer, or compounds containing condensed furan as described in this invention, but are not limited thereto.
[0306] The light-emitting layer doping materials of this invention are classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials. The light-emitting layer doping materials can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. It can be selected from any one or more of the following structures: 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxylic iridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), etc., but not limited to these.
[0307] The hole-blocking layer described in this invention preferably uses a material with strong hole-blocking capability and suitable HOMO / LUMO energy levels. It can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirmonene derivatives, anthrone derivatives, etc., but is not limited thereto.
[0308] The hole-blocking layer material described in this invention is preferably a material that can effectively block hole transport, causing excitons to recombine in the luminescent layer rather than the electron transport layer. It can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc., but is not limited thereto.
[0309] The electron transport layer material of the present invention is preferably a material with high electron mobility. It can be selected from any one or more of the following structures: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 8-hydroxyquinoline-lithium (Liq), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), and 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but is not limited thereto.
[0310] The electron injection layer material described in this invention is preferably a material with a small barrier difference to the adjacent organic layer material. It can be selected from any one or more of the following structures: alkali metal compounds (e.g., lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, cesium 8-hydroxyquinoline, aluminum 8-hydroxyquinoline), organometallic salts (metal acetate, metal benzoate, or metal stearate), molybdenum trioxide, aluminum, etc., but is not limited thereto.
[0311] The cathode material of the present invention preferably uses a material with a low work function that can promote electron injection into the organic layer, thereby reducing the electron injection barrier. It can be selected from any one or more of the following structures: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.
[0312] The capping layer of this invention is provided on the outside of either the anode or the cathode electrode, and preferably uses a material that can improve the internal optical coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., or compounds containing condensed furan as described in this invention, but are not limited thereto.
[0313] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.
[0314] The organic electroluminescent device of the present invention can be applied using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating.
[0315] The organic electroluminescent device described in this invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.
[0316] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.
[0317] This invention provides a method for preparing compounds represented by Formula I, which are prepared via the Suzuki and Buchwald coupling reactions well known in the art. However, the preparation method of this invention is not limited to these methods, and the structure of Formula I can be prepared via the reaction route shown below: 1. Preparation of intermediate c:
[0318] 2. Preparation of Formula I:
[0319] Among them, Xa, Xb, Xc, Xd are the same or different from each other, and are selected from any one of Cl, Br, I; the restrictions on Ar1~Ar3, L1~L3, and x are the same as those above.
[0320] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.
[0321] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.
[0322] Preparation and characterization of compounds
[0323] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; they can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent purity.
[0324] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg. Synthesis Example 1: Preparation of Intermediate c-103
[0325] Under nitrogen protection, starting materials e-103 (27.54 g, 80.00 mmol), f-103 (15.64 g, 80.00 mmol), K2CO3 (16.59 g, 120.00 mmol), and 400 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. After purging the air with nitrogen three times, Pd(PPh3)4 (0.92 g, 0.80 mmol) was added. The mixture was stirred and heated under reflux for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol in a 5:1 ratio to obtain intermediate c-103 (20.24 g, yield 76%) with an HPLC purity ≥99.88%. Mass spectrometry m / z: 332.0919 (theoretical value: 332.0906).
[0326] Other intermediates required for the present invention were synthesized using the above-described synthesis method. The relevant raw materials are shown in Table 1. Table 1:
[0327] Synthesis Example 2: Preparation of Compound 10
[0328] Preparation of intermediate B-10
[0329] Under nitrogen protection, a-10 (12.31 g, 50.00 mmol), e-103 (17.21 g, 50.00 mmol), and K2CO3 (13.82 g, 100.00 mmol) were dissolved in 250 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (0.73 g, 1.00 mmol) was added with stirring, and the mixture was heated under reflux for 4.8 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in a 7:1 ratio to give intermediate B-10 (14.95 g, 78% yield); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 383.1321 (theoretical value: 383.1310).
[0330] Preparation of compound 10
[0331] Under nitrogen protection, B-10 (11.50 g, 30.00 mmol), c-10 (8.91 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 10 (13.13 g, 73% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 599.1893 (theoretical value: 599.1885). Theoretical elemental content (%) C 44 H 25 NO2: C, 88.13; H, 4.20; N, 2.34; Measured element content (%): C, 88.16; H, 4.15; N, 2.39.
[0332] Synthesis Example 3: Preparation of Compound 33
[0333] According to the preparation method in Synthesis Example 2, c-10 was replaced with an equimolar amount of c-33 to obtain compound 33 (12.95 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 599.1897 (theoretical value: 599.1885). Theoretical elemental content (%) C 44 H 25NO2: C, 88.13; H, 4.20; N, 2.34; Measured element content (%): C, 88.12; H, 4.27; N, 2.30.
[0334] Synthesis Example 4: Preparation of Compound 34
[0335] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-34, and c-10 was replaced with an equimolar amount of c-34 to obtain compound 34 (13.34 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 600.1830 (theoretical value: 600.1838). Theoretical elemental content (%) C 43 H 24 N2O2: C, 85.98; H, 4.03; N, 4.66; Measured element content (%): C, 85.97; H, 4.05; N, 4.69.
[0336] Synthesis Example 5: Preparation of Compound 35
[0337] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-35, e-103 was replaced with an equimolar amount of e-788, and c-10 was replaced with an equimolar amount of c-35, yielding compound 35 (13.13 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 599.1894 (theoretical value: 599.1885). Theoretical elemental content (%) C 44 H 25 NO2: C, 88.13; H, 4.20; N, 2.34; Measured element content (%): C, 88.15; H, 4.17; N, 2.36.
[0338] Synthesis Example 6: Preparation of Compound 103
[0339] According to the preparation method in Synthesis Example 2, c-10 was replaced with an equimolar amount of c-103 to obtain compound 103 (14.48 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 679.2440 (theoretical value: 679.2449). Theoretical elemental content (%) C 50 H 25 D4NO2: C, 88.34; H, 4.89; N, 2.06; Measured element content (%): C, 88.37; H, 4.91; N, 2.01.
[0340] Synthesis Example 7: Preparation of Compound 120
[0341] According to the preparation method in Synthesis Example 2, c-10 was replaced with an equimolar amount of c-120 to obtain compound 120 (14.64 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 677.2120 (theoretical value: 677.2103). Theoretical elemental content (%) C 48 H 27 N3O2: C, 85.06; H, 4.02; N, 6.20; Measured element content (%): C, 85.11; H, 4.03; N, 6.15.
[0342] Synthesis Example 8: Preparation of Compound 123
[0343] According to the preparation method in Synthesis Example 2, c-10 was replaced with an equimolar amount of c-123 to obtain compound 123 (16.11 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 725.2365 (theoretical value: 725.2355). Theoretical elemental content (%) C 54 H 31 NO2: C, 89.36; H, 4.31; N, 1.93; Measured element content (%): C, 89.32; H, 4.35; N, 1.96.
[0344] Synthesis Example 9: Preparation of Compound 171
[0345] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-171 to obtain compound 171 (12.74 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 606.2310 (theoretical value: 606.2325). Theoretical elemental content (%) C 44 H 18 D7NO2: C, 87.10; H, 5.31; N, 2.31; Measured elemental content (%): C, 87.12; H, 5.34; N, 2.30.
[0346] Synthetic Example 10: Preparation of Compound 177
[0347] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-177 to obtain compound 177 (13.97 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 655.2526 (theoretical value: 655.2511). Theoretical elemental content (%) C 48 H 33 NO2: C, 87.91; H, 5.07; N, 2.14; Measured element content (%): C, 87.88; H, 5.05; N, 2.13.
[0348] Synthesis Example 11: Preparation of Compound 189
[0349] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-189, and e-103 was replaced with an equimolar amount of e-788, yielding compound 189 (14.80 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 675.2190 (theoretical value: 675.2198). Theoretical elemental content (%) C 50 H 29 NO2: C, 88.87; H, 4.33; N, 2.07; Measured element content (%): C, 88.84; H, 4.35; N, 2.09.
[0350] Synthesis Example 12: Preparation of Compound 246
[0351] Preparation of intermediate B-246
[0352] Under nitrogen protection, a-246 (19.64 g, 70 mmol), e-103 (24.10 g, 70.00 mmol), and K2CO3 (19.35 g, 140.00 mmol) were dissolved in 350 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.02 g, 1.40 mmol) was added with stirring, and the mixture was heated under reflux for 5.0 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in a 7:1 ratio to give intermediate B-246 (22.82 g, 78% yield); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 417.0929 (theoretical value: 417.0920).
[0353] Preparation of intermediate C-246
[0354] Under argon protection, B-246 (20.89 g, 50.00 mmol), d-246 (12.20 g, 50.00 mmol), K2CO3 (10.37 g, 75.00 mmol), and 420 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with argon, Pd(PPh3)4 (0.58 g, 0.50 mmol) was added. The mixture was stirred and heated under reflux for 4.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol in a 9:1 ratio to obtain intermediate C-246 (18.98 g, yield 76%) with an HPLC purity ≥99.86%. Mass spectrometry m / z: 499.1587 (theoretical value: 499.1572).
[0355] Preparation of compound 246
[0356] Under nitrogen protection, C-246 (14.99 g, 30.00 mmol), C-10 (8.91 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were then added. The mixture of the above reactants was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 246 (15.46 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 715.2159 (theoretical value: 715.2147). Theoretical elemental content (%) C 52 H 29 NO3: C, 87.25; H, 4.08; N, 1.96; Measured element content (%): C, 87.27; H, 4.05; N, 1.97.
[0357] Synthetic Example 13: Preparation of Compound 436
[0358] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-436 to obtain compound 436 (15.70 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 716.2114 (theoretical value: 716.2100). Theoretical elemental content (%) C 51 H 28N2O3: C, 85.46; H, 3.94; N, 3.91; Measured element content (%): C, 85.48; H, 3.91; N, 3.95.
[0359] Synthesis Example 14: Preparation of Compound 437
[0360] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-437 to obtain compound 437 (16.89 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 792.2430 (theoretical value: 792.2413). Theoretical elemental content (%) C 57 H 32 N2O3: C, 86.35; H, 4.07; N, 3.53; Measured element content (%): C, 86.30; H, 4.06; N, 3.50.
[0361] Synthesis Example 15: Preparation of Compound 437
[0362] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-475 to obtain compound 475 (17.70 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 842.2560 (theoretical value: 842.2569). Theoretical elemental content (%) C 57 H 32 N2O3: C, 86.92; H, 4.07; N, 3.32; Measured element content (%): C, 86.90; H, 4.05; N, 3.35.
[0363] Synthetic Example 16: Preparation of Compound 476
[0364] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-476 to obtain compound 476 (16.91 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 793.2350 (theoretical value: 793.2365). Theoretical elemental content (%) C 56 H 31 N3O3: C, 84.72; H, 3.94; N, 5.29; Measured element content (%): C, 84.75; H, 3.98; N, 5.24.
[0365] Synthesis Example 17: Preparation of Compound 488
[0366] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-488 to obtain compound 476 (15.07 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 717.2040 (theoretical value: 717.2052). Theoretical elemental content (%) C 50 H 27 N3O3: C, 83.67; H, 3.79; N, 5.85; Measured element content (%): C, 83.64; H, 3.77; N, 5.80.
[0367] Synthesis Example 18: Preparation of Compound 501
[0368] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-501 to obtain compound 501 (17.70 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 842.2560 (theoretical value: 842.2569). Theoretical elemental content (%) C 61 H 34 N2O3: C, 86.92; H, 4.07; N, 3.32; Measured element content (%): C, 86.90; H, 4.03; N, 3.36.
[0369] Synthetic Example 19: Preparation of Compound 576
[0370] Preparation of intermediate B-576
[0371] Under nitrogen protection, a-576 (11.80 g, 50.00 mmol), e-103 (34.42 g, 100.00 mmol), and K2CO3 (20.73 g, 150.00 mmol) were dissolved in 350 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (0.88 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to give intermediate B-576 (23.39 g, 78% yield); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 599.1896 (theoretical value: 599.1885).
[0372] Preparation of compound 576
[0373] Under nitrogen protection, B-576 (17.99 g, 30.00 mmol), c-10 (8.91 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added, and the mixture was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 576 (17.62 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 815.2468 (theoretical value: 815.2460). Theoretical elemental content (%) C 60 H 33 NO3: C, 88.32; H, 4.08; N, 1.72; Measured element content (%): C, 88.36; H, 4.01; N, 1.76.
[0374] Synthesis Example 20: Preparation of Compound 625
[0375] According to the preparation method in Synthesis Example 12, a-246 was replaced with an equimolar amount of a-625, e-103 was replaced with an equimolar amount of e-788, d-246 was replaced with an equimolar amount of d-625, and c-10 was replaced with an equimolar amount of c-625, yielding compound 625 (17.00 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 765.2312 (theoretical value: 765.2304). Theoretical elemental content (%) C 56 H 31 NO3: C, 87.82; H, 4.08; N, 1.83; Measured element content (%): C, 87.86; H, 4.05; N, 1.88.
[0376] Synthesis Example 21: Preparation of Compound 643
[0377] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-643 to obtain compound 643 (13.84 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 649.2057 (theoretical value: 649.2042). Theoretical elemental content (%) C 48H 27 NO2: C, 88.73; H, 4.19; N, 2.16; Measured element content (%): C, 88.77; H, 4.16; N, 2.21.
[0378] Synthesis Example 22: Preparation of Compound 663
[0379] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-663 to obtain compound 663 (16.11 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 715.2525 (theoretical value: 715.2511). Theoretical elemental content (%) C 53 H 33 NO2: C, 88.93; H, 4.65; N, 1.96; Measured element content (%): C, 88.95; H, 4.63; N, 1.98.
[0380] Synthesis Example 23: Preparation of Compound 676
[0381] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-676 to obtain compound 676 (15.31 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 689.1999 (theoretical value: 689.1991). Theoretical elemental content (%) C 50 H 27 NO3: C, 87.07; H, 3.95; N, 2.03; Measured element content (%): C, 87.09; H, 3.95; N, 2.05.
[0382] Synthesis Example 24: Preparation of Compound 693
[0383] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-693 to obtain compound 693 (16.52 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 764.2475 (theoretical value: 764.2464). Theoretical elemental content (%) C 56 H 32 N2O2: C, 87.94; H, 4.22; N, 3.66; Measured element content (%): C, 87.90; H, 4.27; N, 3.69.
[0384] Synthesis Example 25: Preparation of Compound 713
[0385] According to the preparation method in Synthesis Example 12, d-246 was replaced with an equimolar amount of d-713, and c-10 was replaced with an equimolar amount of c-713 to obtain compound 713 (17.36 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 781.2990 (theoretical value: 781.2981). Theoretical elemental content (%) C 58 H 39 NO2: C, 89.09; H, 5.03; N, 1.79; Measured element content (%): C, 89.07; H, 5.06; N, 1.78.
[0386] Synthesis Example 26: Preparation of Compound 717
[0387] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-717, and c-10 was replaced with an equimolar amount of c-717, yielding compound 717 (16.01 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 730.2660 (theoretical value: 730.2669). Theoretical elemental content (%) C 54 H 26 D5NO2: C, 88.74; H, 4.96; N, 1.92; Measured element content (%): C, 88.72; H, 4.99; N, 1.96.
[0388] Synthesis Example 27: Preparation of Compound 725
[0389] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-725, and d-246 was replaced with an equimolar amount of d-725, yielding compound 725 (17.20 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 818.3850 (theoretical value: 818.3859). Theoretical elemental content (%) C 60 H 34 D9NO2: C, 87.99; H, 6.40; N, 1.71; Measured element content (%): C, 87.98; H, 6.45; N, 1.75.
[0390] Synthesis Example 28: Preparation of Compound 738
[0391] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-738 to obtain compound 738 (13.52 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 600.1850 (theoretical value: 600.1838). Theoretical elemental content (%) C 43 H 24 N2O2: C, 85.98; H, 4.03; N, 4.66; Measured element content (%): C, 85.96; H, 4.07; N, 4.62.
[0392] Synthesis Example 29: Preparation of Compound 747
[0393] According to the preparation method in Synthesis Example 12, a-246 was replaced with an equimolar amount of a-747, e-103 was replaced with an equimolar amount of b-747, d-246 was replaced with an equimolar amount of d-747, and c-10 was replaced with an equimolar amount of c-747, yielding compound 747 (18.76 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 833.2120 (theoretical value: 833.2137). Theoretical elemental content (%) C 58 H 31 N3O2S: C, 83.53; H, 3.75; N, 5.04; Measured element content (%): C, 83.56; H, 3.77; N, 5.09.
[0394] Synthesis Example 30: Preparation of Compound 752
[0395] According to the preparation method in Synthesis Example 2, e-103 was replaced with an equimolar amount of b-752 to obtain compound 752 (13.67 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 615.1670 (theoretical value: 615.1657). Theoretical elemental content (%) C 44 H 25 NOS: C, 85.83; H, 4.09; N, 2.27; Measured element content (%): C, 85.86; H, 4.11; N, 2.25.
[0396] Synthesis Example 31: Preparation of Compound 787
[0397] According to the preparation method in Synthesis Example 2, e-103 was replaced with an equimolar amount of b-787, and c-10 was replaced with an equimolar amount of c-787 to obtain compound 787 (15.15 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 691.1982 (theoretical value: 691.1970). Theoretical elemental content (%) C 50 H 29 NOS: C, 86.80; H, 4.23; N, 2.02; Measured element content (%): C, 86.82; H, 4.25; N, 1.98.
[0398] Synthesis Example 32: Preparation of Compound 788
[0399] According to the preparation method in Synthesis Example 2, e-103 was replaced with an equimolar amount of b-787, and c-10 was replaced with an equimolar amount of c-788, yielding compound 788 (16.36 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 767.2299 (theoretical value: 767.2283). Theoretical elemental content (%) C 56 H 33 NOS: C, 87.59; H, 4.33; N, 1.82; Measured element content (%): C, 87.57; H, 4.37; N, 1.80.
[0400] Synthesis Example 33: Preparation of Compound 797
[0401] Following the preparation method of Synthesis Example 12, c-10 was replaced with an equimolar amount of c-797, and d-246 was replaced with an equimolar amount of b-787, yielding compound 797 (20.45 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 908.2480 (theoretical value: 908.2497). Theoretical elemental content (%) C 65 H 36 N2O2S: C, 85.88; H, 3.99; N, 3.08; Measured element content (%): C, 85.85; H, 3.98; N, 3.04.
[0402] Synthesis Example 34: Preparation of Compound 819
[0403] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, and d-246 was replaced with an equimolar amount of d-819, yielding compound 819 (17.91 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 817.2449 (theoretical value: 817.2439). Theoretical elemental content (%) C 60 H 35 NOS: C, 88.10; H, 4.31; N, 1.71; Measured element content (%): C, 88.15; H, 4.32; N, 1.74.
[0404] Synthesis Example 35: Preparation of Compound 820
[0405] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, and d-246 was replaced with an equimolar amount of d-820, yielding compound 820 (16.47 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 731.2296 (theoretical value: 731.2283). Theoretical elemental content (%) C 53 H 33 NOS: C, 86.98; H, 4.54; N, 1.91; Measured element content (%): C, 86.95; H, 4.56; N, 1.95.
[0406] Synthesis Example 36: Preparation of Compound 879
[0407] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 with an equimolar amount of d-879, and c-10 with an equimolar amount of c-879, yielding compound 879 (16.16 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 747.1698 (theoretical value: 747.1691). Theoretical elemental content (%) C 52 H 29 NOS2: C, 83.51; H, 3.91; N, 1.87; Measured element content (%): C, 83.55; H, 3.90; N, 1.85.
[0408] Synthesis Example 37: Preparation of Compound 958
[0409] According to the preparation method in Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 with an equimolar amount of d-958, and c-10 with an equimolar amount of c-958, yielding compound 958 (17.76 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 810.2080 (theoretical value: 810.2089). Theoretical elemental content (%) C 55 H 30 N4O2S: C, 81.46; H, 3.73; N, 6.91; Measured elemental content (%): C, 81.44; H, 3.76; N, 6.95.
[0410] Synthesis Example 38: Preparation of Compound 1057
[0411] According to the preparation method in Synthesis Example 2, e-103 was replaced with an equimolar amount of b-1057, and c-10 was replaced with an equimolar amount of c-1057 to obtain compound 1057 (13.85 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 615.1646 (theoretical value: 615.1657). Theoretical elemental content (%) C 44 H 25 NOS: C, 85.83; H, 4.09; N, 2.27; Measured element content (%): C, 85.85; H, 4.04; N, 2.29.
[0412] Synthesis Example 39: Preparation of Compound 1065
[0413] According to the preparation method in Synthesis Example 2, a-10 was replaced with an equimolar amount of a-1065, e-103 was replaced with an equimolar amount of b-1065, and c-10 was replaced with an equimolar amount of c-1057, yielding compound 1065 (14.32 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 691.1978 (theoretical value: 691.1970). Theoretical elemental content (%) C 50 H 29 NOS: C, 86.80; H, 4.23; N, 2.02; Measured element content (%): C, 86.81; H, 4.25; N, 2.05.
[0414] Synthesis Example 40: Preparation of Compound 1091
[0415] According to the preparation method in Synthesis Example 2, e-103 was replaced with an equimolar amount of b-1091, and c-10 was replaced with an equimolar amount of c-1091 to obtain compound 1091 (15.36 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 691.1979 (theoretical value: 691.1970). Theoretical elemental content (%) C 50 H 29 NOS: C, 86.80; H, 4.23; N, 2.02; Measured element content (%): C, 86.75; H, 4.20; N, 2.03.
[0416] Synthesis Example 41: Preparation of Compound 1091
[0417] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 with an equimolar amount of d-1194, and c-10 with an equimolar amount of c-958, yielding compound 1194 (16.31 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 776.2450 (theoretical value: 776.2464). Theoretical elemental content (%) C 57 H 32 N2O2: C, 88.12; H, 4.15; N, 3.61; Measured element content (%): C, 88.10; H, 4.14; N, 3.63.
[0418] Synthesis Example 42: Preparation of Compound 1249
[0419] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-1249, and c-10 was replaced with an equimolar amount of c-1249, yielding compound 1249 (16.18 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 748.1655 (theoretical value: 748.1643). Theoretical elemental content (%) C 51 H 28 N2OS2: C, 81.79; H, 3.77; N, 3.74; Measured element content (%): C, 81.75; H, 3.74; N, 3.78.
[0420] Synthesis Example 43: Preparation of Compound 1281
[0421] Following the preparation method of Synthesis Example 12, d-246 was replaced with an equimolar amount of d-1281, and c-10 was replaced with an equimolar amount of c-1281 to obtain compound 1281 (17.27 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 810.2070 (theoretical value: 810.2089). Theoretical elemental content (%) C 55 H 30 N4O2S: C, 81.46; H, 3.73; N, 6.91; Measured elemental content (%): C, 81.44; H, 3.70; N, 6.94.
[0422] Synthesis Example 44: Preparation of Compound 1289
[0423] According to the preparation method in Synthesis Example 12, a-246 was replaced with an equimolar amount of a-1289, d-246 was replaced with an equimolar amount of d-1289, and c-10 was replaced with an equimolar amount of c-1057, yielding compound 1289 (17.72 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 797.1862 (theoretical value: 797.1847). Theoretical elemental content (%) C 56 H 31 NOS2: C, 84.29; H, 3.92; N, 1.76; Measured element content (%): C, 84.26; H, 3.96; N, 1.71.
[0424] Synthesis Example 45: Preparation of Compound 1401
[0425] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 with an equimolar amount of e-103, and c-10 with an equimolar amount of c-1057, yielding compound 1401 (18.83 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 847.2024 (theoretical value: 847.2004). Theoretical elemental content (%) C 60 H 33 NOS2: C, 84.98; H, 3.92; N, 1.65; Measured element content (%): C, 84.95; H, 3.96; N, 1.61.
[0426] Synthesis Example 46: Preparation of Compound 1477
[0427] According to the preparation method in Synthesis Example 19, c-10 was replaced with an equimolar amount of c-958 to obtain compound 1477 (17.89 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 816.2426 (theoretical value: 816.2413). Theoretical elemental content (%) C 59 H 32 N2O3: C, 86.75; H, 3.95; N, 3.43; Measured element content (%): C, 86.74; H, 3.93; N, 3.45.
[0428] Synthesis Example 47: Preparation of Compound 1558
[0429] According to the preparation method in Synthesis Example 12, e-103 was replaced with an equimolar amount of b-1558, d-246 was replaced with an equimolar amount of d-1558, and c-10 was replaced with an equimolar amount of c-958, yielding compound 1558 (20.98 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 984.2825 (theoretical value: 984.2810). Theoretical elemental content (%) C 71 H 40 N2O2S: C, 86.56; H, 4.09; N, 2.84; Measured element content (%): C, 86.51; H, 4.08; N, 2.86.
[0430] Synthesis Example 48: Preparation of Compound 1681
[0431] According to the preparation method in Synthesis Example 12, a-246 was replaced with an equimolar amount of a-1681, e-103 was replaced with an equimolar amount of b-1681, and d-246 was replaced with an equimolar amount of d-1681, yielding compound 1681 (17.37 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 826.2629 (theoretical value: 826.2620). Theoretical elemental content (%) C 61 H 34 N2O2: C, 88.60; H, 4.14; N, 3.39; Measured elemental content (%): C, 88.64; H, 4.17; N, 3.35.
[0432] Synthesis Example 49: Preparation of Compound 1697
[0433] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-1697, and d-246 was replaced with an equimolar amount of d-1697, yielding compound 1697 (18.15 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 876.2787 (theoretical value: 876.2777). Theoretical elemental content (%) C 65 H 36 N2O2: C, 89.02; H, 4.14; N, 3.19; Measured element content (%): C, 89.05; H, 4.18; N, 3.18.
[0434] Synthesis Example 50: Preparation of Compound 2096
[0435] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 with an equimolar amount of d-2096, and c-10 with c-958, yielding compound 2096 (18.51 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 868.2540 (theoretical value: 868.2548). Theoretical elemental content (%) C 63 H 36 N2OS: C, 87.07; H, 4.18; N, 3.22; Measured element content (%): C, 87.05; H, 4.14; N, 3.26.
[0436] Synthesis Example 51: Preparation of Compound 2119
[0437] Following the preparation method of Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 with an equimolar amount of d-2119, and c-10 with c-2119, yielding compound 2119 (17.16 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 816.2249 (theoretical value: 816.2235). Theoretical elemental content (%) C 59 H 32 N2OS: C, 86.74; H, 3.95; N, 3.43; Measured element content (%): C, 86.70; H, 3.90; N, 3.46.
[0438] Synthesis Example 52: Preparation of Compound 2253
[0439] According to the preparation method in Synthesis Example 12, e-103 was replaced with an equimolar amount of b-787, d-246 was replaced with an equimolar amount of d-2253, and c-10 was replaced with c-2253, yielding compound 2253 (18.24 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 893.2514 (theoretical value: 893.2501). Theoretical elemental content (%) C 64 H 35 N3OS: C, 85.98; H, 3.95; N, 4.70; Measured element content (%): C, 85.94; H, 3.90; N, 4.73.
[0440] [Device Example 1]
[0441] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.
[0442] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate. The deposition process included: hole injection layer P-1:HT-1 = 5:95 (mass ratio, 10 nm); HT-1 (100 nm); light-emitting layer BH-1:BD = 97:3 (mass ratio, 35 nm); electron transport layer ET-1:Liq = 1:1 (mass ratio, 35 nm); electron injection layer LiF (0.8 nm); cathode Mg:Ag = 1:9 (mass ratio, 12 nm); and compound 10 (80 nm).
[0443]
[0444]
[0445] [Device Examples 2-51]
[0446] Using compounds 33, 34, 35, 103, 120, 123, 171, 177, 189, 246, 436, 437, 475, 476, 488, 501, 576, 625, 643, 663, 676, 693, 713, 717, 725, 738, 747, 752, 787, and 788 of the present invention. Compounds 797, 819, 820, 879, 958, 1057, 1065, 1091, 1194, 1249, 1281, 1289, 1401, 1477, 1558, 1681, 1697, 2096, 2119, and 2253 were used to replace compound 10 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.
[0447] [Comparative Device Examples 1-3]
[0448] Comparative compounds 1, 2, and 3 were used to replace compound 10 in device example 1 as the capping material, and an organic electroluminescent device was prepared using the same preparation method as device example 1.
[0449] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 1-51 and Comparative Examples 1-3 of the present invention are shown in Table 1 below.
[0450]
[0451]
[0452] As can be seen from the data in Table 1, applying the compound containing condensed furan shown in Formula I of the present invention as a capping material in organic electroluminescent devices can effectively improve the luminous efficiency and lifespan of the devices.
[0453] [Device Example 52]
[0454] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.
[0455] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO substrate, in which the following layers were deposited sequentially: hole injection layer HI-1 (60 nm); first hole transport layer HT-2 (100 nm); light-emitting layer compound 10:BD-2 = 96:4 (mass ratio, 40 nm); electron transport layer ET-2:Liq = 1:1 (mass ratio, 35 nm); electron injection layer LiF (1.0 nm); and cathode Al (100 nm).
[0456]
[0457] [Device Examples 53-102]
[0458] Using compounds 33, 34, 35, 103, 120, 123, 171, 177, 189, 246, 436, 437, 475, 476, 488, 501, 576, 625, 643, 663, 676, 693, 713, 717, 725, 738, 747, 752, 787, and 788 of the present invention, Compounds 797, 819, 820, 879, 958, 1057, 1065, 1091, 1194, 1249, 1281, 1289, 1401, 1477, 1558, 1681, 1697, 2096, 2119, and 2253 were used to replace compound 10 in device example 52 as the main material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 52.
[0459] [Comparative Device Examples 4-5]
[0460] Comparative compounds 4 and 5 were used to replace compound 10 in device example 52 as the main material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 52.
[0461] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 51-102 and Comparative Examples 4-5 of the present invention are shown in Table 2 below.
[0462]
[0463]
[0464] As can be seen from the data in Table 2, the compound containing condensed furan shown in Formula I of this invention can reduce the driving voltage of the device and effectively improve the luminous efficiency and lifespan of the device.
[0465] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.
Claims
1. A compound containing condensed furan, characterized in that, The compound containing condensed furan is shown in Formula I. The Ar2 and Ar3 are independently selected from the following groups: X is selected from O or S; The v is independently selected from C (R2) or N, and when v is bonded to other groups, the v is selected from C atoms; The R2 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted silyl. The x is independently selected from C(R4) or N; The R4 is selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent R4s can be interconnected to form one or more substituted or unsubstituted C5 or more rings; The Ar1 is selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or any one of the following groups: The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms; W1 is selected from O, S or N (Rz); Q1 is selected from O, S, N (Rz) or C (RxRy); The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings; The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings; The Rd1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; The L1 is selected from single bonds, substituted or unsubstituted C6~C30 arylene groups, substituted or unsubstituted C2~C30 heteroarylene groups, substituted or unsubstituted C3~C30 alicyclic and C6~C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3~C30 alicyclic and C2~C30 heteroaromatic rings with fused cycloyl groups. The L2 and L3 are independently selected from single bonds or any of the following groups: The u is independently selected from CH or N; The V is selected from O or S; The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rm is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, and substituted or unsubstituted silyl. The Rp and Rq are independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rp and Rq can be connected to each other to form substituted or unsubstituted rings; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6.
2. The compound containing condensed furan according to claim 1, characterized in that, Ar2 and Ar3 are independently selected from any one of the structures shown below. R2 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthalene. alkyl, phenanthrene, phenylene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocyclopentane, benzocyclopentenyl, benzocycloheptane, benzocycloheptenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl; The number b0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the number b1 is selected from 0, 1, or 2; the number b2 is selected from 0, 1, 2, or 3; the number b3 is selected from 0, 1, 2, 3, 4, 5, or 6; the number b4 is selected from 0, 1, 2, 3, 4, or 5; the number b5 is selected from 0, 1, 2, 3, or 4; the number b6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the number b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.
3. The compound containing condensed furan, characterized in that, The Selected from any one of the following groups: X1 is selected from O, S, C (RsRr) or N (Rg); The x is independently selected from C(R4), or in each group, one, two, three, four, five, or six x are selected from N, and the rest are selected from C(R4). When x is bonded to other groups, the x is selected from C atoms. The R4 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rg is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rs and Rr are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. adamantyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or Rs and Rr can be interconnected to form one or more substituted or unsubstituted rings.
4. A compound containing condensed furan according to claim 1, characterized in that, The Ar1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, or any of the structures shown below. The t is independently selected from CH, or one, two or three ts in each group are selected from N, and the rest are selected from CH. When t is bonded to other groups, the t is selected from C atoms. The Rz is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd1 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rds may be connected to each other to form one or more substituted or unsubstituted rings; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a7 is selected from 0, 1, 2, 3, 4, 5, or 6; a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; a 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; a 12 Select from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.
5. A compound containing condensed furan according to claim 1, characterized in that, The L1 is selected from a single bond or any of the structures shown below. The i is independently selected from CH or N; The Y is selected from O, S, or N (Re); The ring Q is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rt is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rt can be interconnected to form one or more substituted or unsubstituted rings; The Rt1 is independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted silyl. The Rp0 and Rq0 are independently selected from any one of hydrogen, deuterium, halogen, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, substituted or unsubstituted silyl, or adjacent Rw and Rz can be connected to each other to form substituted or unsubstituted rings; The Re is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, and substituted or unsubstituted silyl. The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2 or 3; the t3 is selected from 0, 1 or 2; and the t4 is selected from 0, 1, 2, 3, 4, 5 or 6.
6. A compound containing condensed furan according to claim 1, characterized in that, L2 and L3 are independently selected from single bonds or any of the structures shown below. The Rm is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, benzocyclopropane. Benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocycloheptyl, benzocycloheptenyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophenyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, or two adjacent Rm may be connected to each other to form one or more substituted or unsubstituted rings; Rm1 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyano, nitro, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthalene. alkyl, phenanthrene, phenylene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocyclopentane, benzocyclopentenyl, benzocycloheptane, benzocycloheptenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p6 is selected from 0, 1, 2, 3, 4 or 5.
7. A compound containing condensed furan according to claim 1, characterized in that, The compound containing condensed furan is selected from any one of the structures shown below: 。 8. An organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode and / or outside either the anode or the cathode, characterized in that, The organic functional layer comprises any one or more of the compounds containing condensed furans as described in any one of claims 1 to 7.
9. An organic electroluminescent device according to claim 8, wherein the organic functional layer is located between the anode and the cathode, the organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the light-emitting layer is located between the electron transport region and the hole transport region, and the electron transport region is located between the light-emitting layer and the cathode, characterized in that, The light-emitting layer comprises any one or more of the compounds containing condensed furan as described in any one of claims 1 to 7.
10. An organic electroluminescent device according to claim 8, wherein the organic functional layer is located outside either the anode or the cathode electrode, and the organic functional layer includes a capping layer, characterized in that, The coating layer comprises any one or more of the compounds containing condensed furan as described in any one of claims 1 to 7.