Organic compound and organic electroluminescent devices comprising same

Abstract

The present invention relates to an organic compound, and also relates to a single-junction organic electroluminescent device comprising the compound and a tandem organic electroluminescent device comprising the compound. The compound of the present invention has a structure represented by the following formula. Q is selected from a substituted or unsubstituted structure represented by formula (Q-1) or (Q-2) below. When the compound of the present invention is used as the material of an electron injection layer of a single-junction organic electroluminescent device or used as the material of an n-type doped layer and an electron injection layer in a stacked organic electroluminescent device connecting layer (an n-type doped layer / n-type layer / p-type layer), the device prepared shows excellent stability and high efficiency.

Description

An organic compound and an organic electroluminescent device containing the same Technical Field

[0001] The present invention relates to a class of organic compounds and also to single-junction and tandem organic electroluminescent devices using the compounds. Background Art

[0002] Organic light-emitting diodes (OLEDs) are a type of organic electroluminescent device consisting primarily of a cathode, an anode, and a light-emitting unit located between the two electrodes, with the light-emitting unit primarily composed of organic semiconductor materials. As an electro-injection light-emitting device, when voltage is applied to the electrodes of an OLED device, holes and the anode are injected into the organic functional layer, while electrons are injected from the cathode into the organic functional layer. The electrons and holes recombine in the light-emitting layer to form excitons, ultimately generating radiative light. Due to their numerous advantages, such as high brightness, fast response, wide viewing angle, low energy consumption, and flexibility, OLED devices have garnered widespread attention in the fields of solid-state display and lighting technology and are considered one of the most promising display technologies of the 21st century. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, tablets, and other products, and is expected to expand into large-scale display products such as televisions. It is a rapidly developing, technically demanding, and promising new display technology.

[0003] The combination and research of organic functional layers in OLED devices have a crucial impact on device performance. After years of development and research, common functional organic materials currently include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as luminescent host materials and luminescent guest materials (dyes). Currently, the LUMO energy levels of commonly used electron transport materials in OLEDs are mostly between -2.7eV and -3.4eV. However, the work functions of metal cathodes such as Al and Ag are all greater than 4.0eV. Therefore, electrons need to overcome a large injection barrier when injecting from the metal cathode into the LUMO energy level of the electron transport layer, resulting in a high device driving voltage and a carrier imbalance between electrons and holes, which significantly reduces device efficiency and lifetime. To reduce the electron injection barrier and improve device efficiency and lifetime, alkali metal compounds such as Liq are currently widely used as n-type dopants in OLED devices, combined with nitrogen-heteroaromatic electron transport materials and Al electrodes to improve device efficiency and operating life. According to the currently available literature, the mechanism by which alkali metal compound n-type dopants such as LiF and Liq reduce the electron injection barrier is mainly due to the presence of Al and nitrogen heteroaromatic electron transport materials (ETM) during the deposition of Al electrodes. Liq reacts with Al and ETM to produce Li+ ETM - , due to Li + ETM - The presence of greatly reduces the work function on the cathode side, improving the electron injection performance of OLED devices. Therefore, OLED devices using alkali metal compounds such as LiF and Liq as n-type dopants have low operating voltage and high luminous efficiency. However, alkali metal compound electron injection materials such as LiF and Liq often need to be combined with Al electrodes and nitrogen-heteroaromatic ring electron transport materials to achieve good electron injection performance, which greatly limits their application in top-emitting devices and inverted devices. At the same time, the life of the device still needs to be improved, so its application in industrial production is relatively limited. In order to further improve and expand the application of OLED devices, it is of great significance to develop new high-performance electron injection materials.

[0004] In recent years, an OLED device with a tandem structure has received widespread attention. The light-emitting principle of a tandem OLED device is similar to that of a traditional single-layer OLED device. The difference is that a tandem OLED device is composed of multiple light-emitting units connected in series via a connecting layer. The connecting layer acts like an electrode, generating carriers in pairs under the drive of an external electric field. These generated carriers can be further separated and injected into adjacent light-emitting units. Due to this tandem device structure, each light-emitting unit can generate photons and achieve radiative luminescence for each injected electron or hole. Therefore, for a tandem OLED device containing N light-emitting units, its current efficiency is approximately N times that of a single-layer OLED device. To achieve the same brightness, the current density required for a tandem OLED device is greatly reduced, which helps to improve the efficiency roll-off and lifespan of the OLED device.

[0005] Currently, a commonly used interconnect layer structure in tandem OLED devices is n-type doped layer / n-type layer / p-type layer. The energy difference between the LUMO level of the n-type layer and the HOMO level of the p-type layer is small, enabling efficient carrier generation at relatively low drive voltages. The dopant guest in the n-type doped layer primarily consists of alkali metals or alkaline earth metals with low work functions (WF < 3.0 eV), including lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), magnesium (Mg), and calcium (Ca). However, these alkali metal or alkaline earth metal n-type dopants readily diffuse toward the p-type doped layer under the action of an external electric field, leading to an increase in the device's drive voltage during operation and a significant decrease in device lifetime, severely impacting device efficiency and stability.

[0006] In recent years, a transition-metal-coordinated n-type doping strategy has provided a new solution for developing efficient and stable electron injection materials and connecting layers for tandem devices. This n-type doping strategy can be used to construct the electron injection layer of OLED devices and the connecting layer of tandem OLEDs, producing high-efficiency, long-life OLED devices with broad development prospects. By doping transition metals (such as Ag and Cu) into phenanthroline-based organic materials with coordination capabilities (represented by B-Phen), the coordination reaction between the phenanthroline-based material and the transition metal promotes the process of metal electron loss. Therefore, phenanthroline-based organic materials can be used in conjunction with transition metals (such as Ag and Cu) as the electron injection layer of OLED devices, significantly reducing the cathode work function and electron injection barrier, thereby significantly improving the efficiency and life of the device and reducing the device's driving voltage.

[0007] Summary of the Invention

[0008] Research has found that the structure, coordination, and transport properties of o-phenanthroline-based electron injection materials have a significant impact on the performance and application of OLED devices. The present invention aims to provide an organic compound and apply it as an organic functional material in single-junction and tandem organic electroluminescent devices, thereby effectively reducing the driving voltage, improving the device's luminous efficiency and lifespan, and addressing the problems existing in the prior art.

[0009] Specifically, the present invention provides an organic compound having a structure shown in the following formula (1):

[0010] In formula (1), ring C represents a benzene ring that is absent or fused with ring A and ring B. When ring C is absent, ring A and ring B are connected by a single bond.

[0011] R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 chain alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C4-C30 alkylsilyl, unsubstituted or R'-substituted C2-C30 One of an alkylamino group, an unsubstituted or R'-substituted C4-C30 cycloalkylamino group, an unsubstituted or R'-substituted C6-C30 arylamino group, an unsubstituted or R'-substituted C3-C30 heteroarylamino group, an unsubstituted or R'-substituted C6-C30 aryloxy group, an unsubstituted or R'-substituted C6-C60 aromatic boron group, an unsubstituted or R'-substituted C6-C60 aryl group, and an unsubstituted or R'-substituted C3-C60 heteroaryl group;

[0012] R' is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl;

[0013] Q represents a bridging group, and n is an integer from 2 to 8;

[0014] Q is selected from the substituted or unsubstituted structure represented by the following formula (Q-1) or (Q-2):

[0015] In formula (Q-1) and (Q-2), X is selected from C, Si or B, and Y is selected from C or N;

[0016] “—*” represents the attachment site of Q in formula (1), and the number of “—*” is consistent with the selected value of n;

[0017] The expression of “—” crossing over a ring structure indicates that the connection site is at any position on the ring structure that can form a bond;

[0018] When the above-mentioned Q has a substituent, the substituent group is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl.

[0019] Further preferably, the Q is selected from one of the following substituted or unsubstituted groups:

[0020] Further preferably, Q is selected from the substituted or unsubstituted structures shown below:

[0021] When Q has a substituent, the substituent is selected from deuterium, halogen, cyano, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0022] Still more preferably, n is 2, 3 or 4; most preferably, n is 2.

[0023] In the general formula compound of the present invention, preferably, R1, R2, R3, R4, and R5 are independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C4-C10 cycloalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl.

[0024] More preferably, R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, dimethylamino, tetrahydropyrrolyl, piperidinyl, cyclohexylimino, cycloheptylimino, cyclooctylimido, methoxy, ethoxy, propoxy, 1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-1 , thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, tert-butylcarbazolyl, indenocarbazolyl, tetrahydroacridinyl, phenylthio, phenol, naphthylthio, naphthol, anthracenthio, anthracenol, indazolyl, oxazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthracenol, benzoxazolyl, naphthoxazolyl, anthracenol, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, 1,5-diazolyl one or a combination of two of heteroanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, purinyl, pteridinyl, indolizinyl, 1,5,7-triazabicyclo[4.4.0]dec-5-enyl, and 4-methoxyphenyl.

[0025] It should be noted that, unless otherwise defined below, all technical and scientific terms used herein are intended to have the same meaning as those commonly understood by those skilled in the art. References to the technologies used herein are intended to refer to technologies commonly understood in the art, including those modifications or equivalent technologies that are obvious to those skilled in the art.

[0026] In this specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms in the substituent is generally not included. When describing C1 to C30, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc. Other numerical ranges are not repeated here.

[0027] The terms "comprises," "comprising," "having," "containing," or "involving," and other variations thereof herein, are inclusive or open-ended and do not exclude additional unrecited elements or method steps.

[0028] In this specification, “each independently” means that when there are multiple subjects, they may be the same or different.

[0029] The heteroatom in the present invention generally refers to an atom or an atomic group selected from B, N, O, S, P, Si and Se, preferably selected from B, N, O and Si.

[0030] As used herein, the terms "heterocyclyl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and / or triple bonds within the ring) cyclic group having at least one ring atom that is a heteroatom selected from N, O, and S and the remaining ring atoms being C.

[0031] As used herein, the terms "(ylidene)aryl" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "(ylidene)heteroaryl" and "heteroaromatic ring" refer to a monocyclic, bicyclic, or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably refers to an alkyl group substituted with an aryl or heteroaryl group, wherein the aryl, heteroaryl, and alkyl groups are as defined herein.

[0032] In this specification, unless otherwise specified, the description of chemical elements generally includes the concept of isotopes with the same chemical properties. For example, carbon (C) includes 12C, 13C, etc., which will not be repeated here.

[0033] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogen atoms on the designated atom are replaced with a group selected from the indicated group, provided that the designated atom's normal valency in the present context is not exceeded and that the substitution results in a stable compound. Combinations of substituents and / or variables are permissible only if such combinations result in stable compounds.

[0034] If substituents are described as being "independently selected" from a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another (other) substituent.

[0035] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0036] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0037] When a bond to a substituent is shown to pass through a bond connecting two atoms in a ring, then such substituent may be bonded to any ring atom in the substitutable ring.

[0038] The term "about" means within ±10%, preferably within ±5%, and more preferably within ±2% of the stated numerical value.

[0039] In the structural formula disclosed in this specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0040] The above-mentioned monocyclic aromatic group refers to a molecule containing one or at least two phenyl groups. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; a fused-ring aromatic group refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing a ring edge, such as naphthyl, anthracenyl, etc.; a monocyclic heteroaromatic group refers to a molecule containing at least one heteroaromatic group. When the molecule contains one heteroaromatic group and other groups (such as aromatic groups, heteroaromatic groups, alkyl groups, etc.), the heteroaromatic group and other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a fused-ring heteroaromatic group refers to a molecule composed of at least one phenyl group and at least one heteroaromatic group fused together, or a molecule composed of at least two heteroaromatic rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0041] The above-mentioned C6-C60 aromatic ring (or C6-C50 aromatic ring) and C3-C60 heteroaromatic ring (or C3-C50 heteroaromatic ring) in the present invention, unless otherwise specified, are aromatic groups that satisfy the π conjugated system, including monocyclic residues and condensed ring residues. The so-called monocyclic residue refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; a fused ring residue refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing the ring edge, such as naphthyl, anthracenyl, phenanthrenyl, etc.; a monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a fused heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or composed of at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0042] In the present specification, the substituted or unsubstituted C6-C60 aromatic ring (or C6-C50 aromatic ring) is preferably a C6-C30 aromatic ring, more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aromatic ring in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, perylenyl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacene group is selected from the group consisting of 1-naphthacene, 2-naphthacene and 9-naphthacene.

[0043] In the present specification, the substituted or unsubstituted C6-C60 aryl group (or C6-C50 aryl group) is preferably a C6-C30 aryl group, and more preferably a group selected from the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, a benzanthryl group, a phenanthrenyl group, a triphenyl group, a pyrene group, a chrysene group, a peryl group, a fluoranthene group, a tetraphenyl group, a pentacene group, a benzopyrenyl group, a biphenyl group, an aphenyl group, a terphenyl group, a triphenyl group, a tetraphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthrenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis- or trans-indenofluorenyl group, a trimerized indenyl group, an isotrimerized indenyl group, a spirotrimerized indenyl group, and a spiroisotrimerized indenyl group. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene, and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; and the naphthacene group is selected from the group consisting of 1-naphthacene, 2-naphthacene, and 9-naphthacene. The C6-C60 aryl group (or C6-C50 aryl group) of the present invention may also be a group formed by combining the above groups connected by single bonds or / and fused.

[0044] In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring (or C3-C50 heteroaromatic ring) is preferably a C3-C30 heteroaromatic ring, which can be a nitrogen-containing heteroaromatic group, an oxygen-containing heteroaromatic group, a sulfur-containing heteroaromatic group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrrol ... oxazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthioimidazolyl, phenanthroimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthioxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, heteroaromatic rings formed by naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, and benzothiadiazole. Preferred examples of the heteroaromatic ring in the present invention include furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole or indolocarbazole.

[0045] In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group (or C3-C50 heteroaryl group) is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, quinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthioimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthioxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzo pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3 -oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole. The C3-C60 heteroaryl group (or C3-C50 heteroaryl group) of the present invention may also be a combination of the above groups connected by single bonds or / and fused.

[0046] In the present invention, examples of aryloxy and heteroaryloxy groups include groups formed by the aforementioned aryl and heteroaryl groups and oxygen. In the present invention, examples of arylamino and heteroarylamino groups include groups formed by the aforementioned aryl and heteroaryl groups replacing one or two H groups in the -NH2 group.

[0047] In this specification, examples of C1-C20 linear or branched alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, and 2-ethylhexyl. Examples of C1-C20 chain haloalkyl groups include trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl.

[0048] In the present specification, the C3-C20 cycloalkyl group includes monocyclic alkyl groups and polycyclic alkyl groups, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups.

[0049] In the present specification, an alkoxy group refers to a group consisting of the above-mentioned straight-chain or branched alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

[0050] Examples of C1-C20 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy groups. Preferred groups include methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, and isopentyloxy groups, and more preferred groups include methoxy.

[0051] In this specification, examples of C1-C20 alkylsilyl groups include silyl groups substituted with the groups listed above for the C1-C20 alkyl groups, i.e., groups formed by replacing one, two, or three hydrogen atoms on the silyl group with the above-mentioned linear or branched alkyl or cycloalkyl groups. Specific examples include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, and tert-butyldiphenylsilyl groups.

[0052] Furthermore, among the general formula compounds of the present invention, the following specific structural compounds E-1 to E-765 can be preferably selected, and these compounds are only representative:

[0053] Another object of the present invention is to protect the use of the compound of the general formula (1) as an electron injection material in a single-junction organic electroluminescent device, and as an n-type doped layer material and electron injection material in the connecting layer (n-type doped layer / n-type layer / p-type layer) in a tandem organic electroluminescent device. In addition, the application field of the compound of the present invention is not limited to organic electroluminescent materials, but can be further expanded to the technical fields of perovskite and quantum dot light-emitting diodes, optical sensors, solar cells, organic thin film transistors, etc.

[0054] The present invention provides a single-junction organic electroluminescent device, comprising a substrate and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate, wherein the light-emitting functional layer comprises a compound represented by the general formula (1):

[0055] In formula (1), ring C represents a benzene ring that is absent or fused with ring A and ring B. When ring C is absent, ring A and ring B are connected by a single bond.

[0056] R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 chain alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C4-C30 alkylsilyl, unsubstituted or R'-substituted C2-C30 One of an alkylamino group, an unsubstituted or R'-substituted C4-C30 cycloalkylamino group, an unsubstituted or R'-substituted C6-C30 arylamino group, an unsubstituted or R'-substituted C3-C30 heteroarylamino group, an unsubstituted or R'-substituted C6-C30 aryloxy group, an unsubstituted or R'-substituted C6-C60 aromatic boron group, an unsubstituted or R'-substituted C6-C60 aryl group, and an unsubstituted or R'-substituted C3-C60 heteroaryl group;

[0057] R' is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl;

[0058] n is an integer of 2-8; Q is selected from the structure represented by the following formula (Q-1) or (Q-2) which is substituted or unsubstituted:

[0059] In formula (Q-1) and (Q-2), X is selected from C, Si or B, and Y is selected from C or N;

[0060] “—*” represents the attachment site of Q in formula (1), and the number of “—*” is consistent with the selected value of n;

[0061] The expression of “—” crossing over a ring structure indicates that the connection site is at any position on the ring structure that can form a bond;

[0062] When the above-mentioned Q has a substituent, the substituent group is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl.

[0063] Specifically, the light-emitting functional layer includes a light-emitting layer and an electron injection layer, and also includes one or more layers of a hole injection layer, a hole transport layer, and an electron transport layer. The hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the light-emitting layer is formed on the hole transport layer, the electron transport layer is formed on the light-emitting layer, the electron injection layer is formed on the electron transport layer, and the cathode layer is formed on the electron injection layer, wherein the electron injection layer includes at least one compound of the general formula of the present invention shown above and a preferred specific compound;

[0064] The present invention provides a tandem organic electroluminescent device comprising the following structure: an anode, a cathode, at least two electroluminescent units disposed between the anode and cathode, and a connecting layer disposed between adjacent electroluminescent units. Each electroluminescent unit comprises at least an electron transport layer and an organic light-emitting layer. The connecting layer is characterized in that it has a multi-layer structure comprising an n-type doped layer, an n-type layer, and a p-type layer; the n-type doped layer comprises at least one compound of the general formula and preferred specific compounds of the present invention shown above. The electron injection layer is formed on the last light-emitting unit, i.e., below the cathode.

[0065] Further preferably, in the single junction and tandem organic electroluminescent devices of the present invention, the n-type doping layer and the electron injection layer both comprise the compound of the present invention and an n-type dopant. Wherein, the n-type dopant is mainly composed of alkali metals, alkaline earth metals and some transition metals and their salts, including but not limited to lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), magnesium (Mg), calcium (Ca), iron (Fe), chromium (Cr), niobium (Nb), cobalt (Co), manganese (Mn), nickel (Ni), copper (Cu), zinc (Zn), silver (Ag), palladium (Pd), rhodium (Rh), ruthenium (Ru), iridium (Ir), tungsten (W), rhenium (Re), platinum (Pt), gold (Au), ytterbium (Yb) one or more of the mixture. Further preferably, the n-type dopant is Zn, Ag, Cu, Au, Yb.

[0066] In the organic electroluminescent device of the present invention, the n-type doping layer in the electron injection layer and the connecting layer includes an n-dopant and the compound of the present invention in a doping ratio of 0.1 wt % to 50 wt %, and the corresponding doping ratio (volume fraction) is 0.01 vol % to 5 vol %;

[0067] Preferably, the doping ratio of the n-dopant to the compound of the present invention is 0.05 wt % to 20 wt %.

[0068] In the single-junction and tandem organic electroluminescent devices of the present invention, the thickness of the electron injection layer and the n-type doped layer in the connecting layer is 0.1nm-20nm; preferably, the thickness of the electron injection layer is 3-5nm, and the thickness of the n-type doped layer in the connecting layer is 1-10nm.

[0069] When the compounds of the present invention are used in the electron injection layer of an organic electroluminescent device and the connecting layer of a stacked device, the device can achieve higher luminous efficiency and longer life. The following are speculations by the inventors, but these speculations do not limit the scope of protection of the present invention.

[0070] First, the molecular weight of the bridging group Q in the specific compound of the present invention is relatively large, which helps to increase the glass transition temperature of the organic ligand. Further, by incorporating metals such as Ag and Yb, the morphological stability during long-term device operation can be effectively enhanced, thereby improving the device life. Secondly, when the bridging group in the present invention adopts a group with good electron transport properties such as spirofluorene, it can effectively improve the transport properties of the organic ligand. Thirdly, in the compound of the present invention, the presence of nitrogen atoms in rings A and B can effectively coordinate with n-type dopants, achieve efficient n-type doping, and improve electron injection and transport performance.

[0071] Furthermore, in the compounds of the present invention, R1, R2, R3, R4, and R5 are preferably designed as electron-donating substituents, which can significantly enhance the electron cloud density and electrostatic potential near the nitrogen atom in structures such as bipyridine (ring A and ring B are connected by a single bond) or o-phenanthroline (ring A and ring B are jointly connected to ring P), thereby helping to improve its coordination ability with the n-type dopant and achieve more excellent electron injection and transport performance.

[0072] The synergistic effects of the structural design innovations of the compounds described above ensure that OLED devices fabricated with these compounds possess numerous advantages, including low driving voltage, high device efficiency, and long operating life. These advantages meet the current requirements of OLED panel manufacturers for high-performance electron injection layer materials and interconnecting layers for laminated devices. Furthermore, the raw materials required for the preparation of these compounds are readily available, and the synthesis, post-processing, and purification processes are simple and reliable, making them suitable for both scientific research and industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0073] FIG1 is a schematic structural diagram of a tandem organic electroluminescent device according to the present invention. DETAILED DESCRIPTION

[0074] The specific preparation method of the above-mentioned novel compound of the present invention will be described in detail below using a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0075] Various chemicals used in the present invention, such as petroleum ether, dichloromethane, ethyl acetate, ethanol, toluene, sodium carbonate and other basic chemical raw materials, were purchased from Shanghai Titan Technology Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS mass spectrometer (manufactured by Micromass, UK).

[0076] The synthetic method of the compound of the present invention will be briefly described below. First, commercially available 4,7-dichloro-1,10-phenanthroline is used as a raw material, and the 4,7 positions of o-phenanthroline are substituted and modified by Suzuki coupling (as shown in representative synthetic route 1). Subsequently, after multi-step transformation, chlorination is carried out at the 2-position of the o-phenanthroline skeleton, and finally multiple o-phenanthroline skeletons are connected to a bridging group by Suzuki coupling to obtain the target product. For the target product in which the 4,7 positions of o-phenanthroline are directly bonded to heteroatoms (O, N, S, etc.), 4,7-dichloro-1,10-phenanthroline can be modified by base-catalyzed nucleophilic substitution (as shown in representative synthetic route 2), and the corresponding target product can be obtained by a similar process.

[0077] Synthesis Example

[0078] Representative synthetic route 1:

[0079] Representative synthetic route 2:

[0080] More specifically, the synthesis methods of representative compounds of the present invention are shown below.

[0081] Synthesis Example

[0082] Synthesis Example 1: Synthesis of Compound E-1

[0083] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-1, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 672.85. Elemental analysis showed theoretical values ​​(%): C, 87.48; H, 4.20; N, 8.33. Expected values ​​(%): C, 87.49; H, 4.20; N, 8.32.

[0084] Synthesis Example 2: Synthesis of Compound E-6

[0085] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-6, was obtained using conventional methods (70% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 89.73; H, 4.54; N, 5.73. Expected values ​​(%): C, 89.75; H, 4.53; N, 5.72.

[0086] Synthesis Example 3: Synthesis of Compound E-7

[0087] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-3-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-7, was obtained using conventional methods (71% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1177.25. Elemental analysis showed theoretical values ​​(%): C, 90.79; H, 4.45; N, 4.76. Exp. value (%): C, 90.77; H, 4.45; N, 4.78.

[0088] Synthesis Example 4: Synthesis of Compound E-8

[0089] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-4-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-8, was obtained using conventional methods (73% yield, 99.54% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1177.45. Elemental analysis showed theoretical values ​​(%): C, 90.79; H, 4.45; N, 4.76. Exp. value (%): C, 90.78; H, 4.46; N, 4.76.

[0090] Synthesis Example 5: Synthesis of Compound E-9

[0091] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-9, was obtained using conventional methods (71% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 949.25. Elemental analysis: theoretical (%): C, 82.25; H, 5.95; N, 11.81. Exp. values ​​(%): C, 82.26; H, 5.94; N, 11.81.

[0092] Synthesis Example 6: Synthesis of Compound E-16

[0093] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-6-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-16, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1005.25. Elemental analysis showed theoretical values ​​(%): C, 82.44; H, 6.41; N, 11.15. Exp. value (%): C, 82.43; H, 6.41; N, 11.16.

[0094] Synthesis Example 7: Synthesis of Compound E-17

[0095] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-7-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-17, was obtained using conventional methods (72% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 729.25. Elemental analysis showed theoretical values ​​(%): C, 87.33; H, 4.98; N, 7.69. Expected values ​​(%): C, 87.32; H, 4.99; N, 7.69.

[0096] Synthesis Example 8: Synthesis of Compound E-18

[0097] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-8-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-18, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 793.05. Elemental analysis showed theoretical values ​​(%): C, 80.29; H, 4.58; N, 7.07; O, 8.07. Expected values ​​(%): C, 80.28; H, 4.58; N, 7.08; O, 8.07.

[0098] Synthesis Example 9: Synthesis of Compound E19-

[0099] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-19, was obtained using conventional methods (72% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 672.85. Elemental analysis showed theoretical values ​​(%): C, 87.48; H, 4.20; N, 8.32. Exp. value (%): C, 87.47; H, 4.21; N, 8.32.

[0100] Synthesis Example 10: Synthesis of Compound E-24

[0101] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-24, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 89.73; H, 4.54; N, 5.73. Expected values ​​(%): C, 89.75; H, 4.53; N, 5.72.

[0102] Synthesis Example 11: Synthesis of Compound E-25

[0103] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-3-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-25, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1177.25. Elemental analysis showed theoretical values ​​(%): C, 90.79; H, 4.45; N, 4.76. Exp. value (%): C, 90.77; H, 4.47; N, 4.76.

[0104] Synthesis Example 12: Synthesis of Compound E-26

[0105] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-4-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-26, was obtained using conventional methods (70% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1177.25. Elemental analysis showed theoretical values ​​(%): C, 90.79; H, 4.45; N, 4.76. Exp. value (%): C, 90.77; H, 4.47; N, 4.76.

[0106] Synthesis Example 13: Synthesis of Compound E-27

[0107] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-27, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 82.25; H, 5.95; N, 11.80. Expected values ​​(%): C, 82.24; H, 5.95; N, 11.81.

[0108] Synthesis Example 14: Synthesis of Compound E-34

[0109] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-6-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-34, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1005.25. Elemental analysis showed theoretical values ​​(%): C, 82.44; H, 6.42; N, 11.14. Expected values ​​(%): C, 82.43; H, 6.42; N, 11.15.

[0110] Synthesis Example 15: Synthesis of Compound E-35

[0111] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-7-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-36, was obtained using conventional methods (69% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 729.25. Elemental analysis showed theoretical values ​​(%): C, 87.33; H, 4.98; N, 7.69. Exp. value (%): C, 87.31; H, 4.98; N, 7.71.

[0112] Synthesis Example 16: Synthesis of Compound E-36

[0113] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-8-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-36, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 793.25. Elemental analysis: theoretical (%): C, 80.29; H, 4.58; N, 7.07; O, 8.06. Expected values ​​(%): C, 80.28; H, 4.58; N, 7.07; O, 8.07.

[0114] Synthesis Example 17: Synthesis of Compound E-37

[0115] A 500 mL round-bottom flask was charged with E-3-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-37, was obtained using conventional methods (72% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 689.25. Elemental analysis showed theoretical values ​​(%): C, 83.69; H, 4.10; N, 8.13; Si, 4.08. Experimen tal values ​​(%): C, 83.68; H, 4.11; N, 8.13; Si, 4.08.

[0116] Synthesis Example 18: Synthesis of Compound E-42

[0117] A 500 mL round-bottom flask was charged with E-3-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-42, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 993.25. Elemental analysis: theoretical (%): C, 87.07; H, 4.47; N, 5.64; Si, 2.83. Experimental values ​​(%): C, 87.08; H, 4.47; N, 5.63; Si, 2.83.

[0118] Synthesis Example 19: Synthesis of Compound E-45

[0119] A 500 mL round-bottom flask was charged with E-3-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-45, was obtained using conventional methods (72% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 79.63; H, 5.85; N, 11.61; Si, 2.91. Experimen tal values ​​(%): C, 79.62; H, 5.85; N, 11.62; Si, 2.91.

[0120] Synthesis Example 20: Synthesis of Compound E-55

[0121] A 500 mL round-bottom flask was charged with E-4-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-55, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 689.25. Elemental analysis showed theoretical values ​​(%): C, 83.69; H, 4.10; N, 8.13; Si, 4.08. Experimen tal values ​​(%): C, 83.68; H, 4.10; N, 8.14; Si, 4.08.

[0122] Synthesis Example 21: Synthesis of Compound E-60

[0123] A 500 mL round-bottom flask was charged with E-4-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-60, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 993.25. Elemental analysis: theoretical (%): C, 87.07; H, 4.47; N, 5.64; Si, 2.82. Experimen tal values ​​(%): C, 87.08; H, 4.46; N, 5.64; Si, 2.82.

[0124] Synthesis Example 22: Synthesis of Compound E-63

[0125] A 500 mL round-bottom flask was charged with E-4-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-63, was obtained using conventional methods (71% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 965.25. Elemental analysis: theoretical (%): C, 79.63; H, 5.85; N, 11.61; Si, 2.91. Expected values ​​(%): C, 79.64; H, 5.85; N, 11.60; Si, 2.91.

[0126] Synthesis Example 23: Synthesis of Compound E-73

[0127] A 500 mL round-bottom flask was charged with E-5-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-73, was obtained using conventional methods (72% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 673.25. Elemental analysis: theoretical (%): C, 83.81; H, 4.19; B, 1.60; N, 10.40. Experimental values ​​(%): C, 83.80; H, 4.19; B, 1.60; N, 10.41.

[0128] Synthesis Example 24: Synthesis of Compound E-78

[0129] A 500 mL round-bottom flask was charged with E-5-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-78, was obtained using conventional methods (70% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 978.25. Elemental analysis: theoretical (%): C, 87.20; H, 4.54; B, 1.11; N, 7.16. Experimental values ​​(%): C, 87.21; H, 4.54; B, 1.11; N, 7.15.

[0130] Synthesis Example 25: Synthesis of Compound E-81

[0131] A 500 mL round-bottom flask was charged with E-5-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-81, was obtained using conventional methods (72% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 950.25. Elemental analysis: theoretical (%): C, 79.65; H, 5.94; B, 1.14; N, 13.27. Experimental values ​​(%): C, 79.66; H, 5.94; B, 1.14; N, 13.26.

[0132] Synthesis Example 26: Synthesis of Compound E-91

[0133] A 500 mL round-bottom flask was charged with E-6-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-91, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 83.81; H, 4.19; B, 1.60; N, 10.40. Experimental values ​​(%): C, 83.80; H, 4.20; B, 1.60; N, 10.40.

[0134] Synthesis Example 27: Synthesis of Compound E-96

[0135] A 500 mL round-bottom flask was charged with E-6-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-96, was obtained using conventional methods (72% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 978.25. Elemental analysis: theoretical (%): C, 87.20; H, 4.54; B, 1.11; N, 7.15. Experimental values ​​(%): C, 87.20; H, 4.53; B, 1.12; N, 7.15.

[0136] Synthesis Example 28: Synthesis of Compound E-99

[0137] A 500 mL round-bottom flask was charged with E-6-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-99, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 950.25. Elemental analysis: theoretical (%): C, 79.65; H, 5.94; B, 1.14; N, 13.27. Experimental values ​​(%): C, 79.65; H, 5.95; B, 1.13; N, 13.27.

[0138] Synthesis Example 29: Synthesis of Compound E-109

[0139] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-109, was obtained using conventional methods (69% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 625.05. Elemental analysis showed theoretical values ​​(%): C, 86.51; H, 4.52; N, 8.97. Expected values ​​(%): C, 86.50; H, 4.53; N, 8.97.

[0140] Synthesis Example 30: Synthesis of Compound E-112

[0141] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-10-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-112, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 88.12; H, 4.67; N, 7.21. Expected values ​​(%): C, 88.12; H, 4.66; N, 7.22.

[0142] Synthesis Example 31: Synthesis of Compound E-115

[0143] A 500 mL round-bottom flask was charged with E-1-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-115, was obtained using conventional methods (68% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 901.25. Elemental analysis showed theoretical values ​​(%): C, 81.31; H, 6.26; N, 12.43. Exp. value (%): C, 81.32; H, 6.26; N, 12.42.

[0144] Synthesis Example 32: Synthesis of Compound E-125

[0145] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-125, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 625.25. Elemental analysis showed theoretical values ​​(%): C, 86.51; H, 4.52; N, 8.97. Expected values ​​(%): C, 86.50; H, 4.52; N, 8.98.

[0146] Synthesis Example 33: Synthesis of Compound E-128

[0147] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-10-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-128, was obtained using conventional methods (71% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 777.25. Elemental analysis showed theoretical values ​​(%): C, 88.12; H, 4.67; N, 7.21. Expected values ​​(%): C, 88.11; H, 4.67; N, 7.22.

[0148] Synthesis Example 34: Synthesis of Compound E-132

[0149] A 500 mL round-bottom flask was charged with E-2-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-132, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 901.25. Elemental analysis: theoretical (%): C, 81.30; H, 6.26; N, 12.44. Exp. value (%): C, 81.30; H, 6.27; N, 12.43.

[0150] Synthesis Example 35: Synthesis of Compound E-142

[0151] A 500 mL round-bottom flask was charged with E-3-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-142, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 641.25. Elemental analysis: theoretical (%): C, 82.47; H, 4.40; N, 8.74; Si, 4.39. Experimen tal values ​​(%): C, 82.47; H, 4.41; N, 8.74; Si, 4.38.

[0152] Synthesis Example 36: Synthesis of Compound E-145

[0153] A 500 mL round-bottom flask was charged with E-3-1 (8.48 mmol, 1 eq) and E-10-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-145, was obtained using conventional methods (70% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 793.25. Elemental analysis: theoretical (%): C, 84.82; H, 4.58; N, 7.07; Si, 3.53. Experimental values ​​(%): C, 84.82; H, 4.58; N, 7.06; Si, 3.54.

[0154] Synthesis Example 37: Synthesis of Compound E-148

[0155] A 500 mL round-bottom flask was charged with E-3-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-148, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 917.25. Elemental analysis: theoretical (%): C, 78.57; H, 6.15; N, 12.22; Si, 3.06. Expected values ​​(%): C, 78.58; H, 6.15; N, 12.21; Si, 3.06.

[0156] Synthesis Example 38: Synthesis of Compound E-158

[0157] A 500 mL round-bottom flask was charged with E-4-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-158, was obtained using conventional methods (70% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 641.25. Elemental analysis: theoretical value (%): C, 82.47; H, 4.40; N, 8.75; Si, 4.38. Experimental values ​​(%): C, 82.47; H, 4.40; N, 8.74; Si, 4.39.

[0158] Synthesis Example 39: Synthesis of Compound E-162

[0159] A 500 mL round-bottom flask was charged with E-4-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-162, was obtained using conventional methods (71% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 945.25. Elemental analysis: theoretical (%): C, 86.41; H, 4.69; N, 5.93; Si, 2.97. Experimental values ​​(%): C, 86.42; H, 4.68; N, 5.93; Si, 2.97.

[0160] Synthesis Example 40: Synthesis of Compound E-165

[0161] A 500 mL round-bottom flask was charged with E-4-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-165, was obtained using conventional methods (69% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 917.25. Elemental analysis showed theoretical values ​​(%): C, 78.57; H, 6.15; N, 12.22; Si, 3.06. Expected values ​​(%): C, 78.58; H, 6.14; N, 12.22; Si, 3.06.

[0162] Synthesis Example 41: Synthesis of Compound E-175

[0163] A 500 mL round-bottom flask was charged with E-5-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-175, was obtained using conventional methods (67% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 625.25. Elemental analysis: theoretical (%): C, 82.56; H, 4.51; B, 1.73; N, 11.20. Experimental values ​​(%): C, 82.55; H, 4.52; B, 1.73; N, 11.20.

[0164] Synthesis Example 42: Synthesis of Compound E-179

[0165] A 500 mL round-bottom flask was charged with E-5-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-179, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 930.15. Elemental analysis: theoretical (%): C, 86.54; H, 4.77; B, 1.16; N, 7.53. Experimental values ​​(%): C, 86.55; H, 4.77; B, 1.16; N, 7.52.

[0166] Synthesis Example 43: Synthesis of Compound E-182

[0167] A 500 mL round-bottom flask was charged with E-5-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-182, was obtained using conventional methods (71% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 902.25. Elemental analysis: theoretical (%): C, 78.56; H, 6.26; B, 1.20; N, 13.98. Experimental values ​​(%): C, 78.57; H, 6.25; B, 1.20; N, 13.98.

[0168] Synthesis Example 44: Synthesis of Compound E-192

[0169] A 500 mL round-bottom flask was charged with E-6-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-192, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 625.25. Elemental analysis: theoretical (%): C, 82.56; H, 4.51; B, 1.73; N, 11.20. Experimental values ​​(%): C, 82.55; H, 4.52; B, 1.73; N, 11.20.

[0170] Synthesis Example 45: Synthesis of Compound E-196

[0171] A 500 mL round-bottom flask was charged with E-6-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-196, was obtained using conventional methods (72% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 86.54; H, 4.77; B, 1.16; N, 7.53. Experimental values ​​(%): C, 86.55; H, 4.77; B, 1.16; N, 7.52.

[0172] Synthesis Example 46: Synthesis of Compound E-199

[0173] A 500 mL round-bottom flask was charged with E-6-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-199, was obtained using conventional methods (70% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 902.25. Elemental analysis: theoretical (%): C, 78.56; H, 6.26; B, 1.20; N, 13.98. Experimental values ​​(%): C, 78.55; H, 6.27; B, 1.20; N, 13.98.

[0174] Synthesis Example 47: Synthesis of Compound E-209

[0175] A 500 mL round-bottom flask was charged with E-7-1 (8.48 mmol, 1 eq) and E-1-2 (29.68 mmol, 3.5 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (101.76 mmol, 12 eq) and Pd(PPh₃)₄ (2.12 mmol, 0.25 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-209, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 851.25. Elemental analysis showed theoretical values ​​(%): C, 86.10; H, 4.02; N, 9.88. Exp. value (%): C, 86.11; H, 4.01; N, 9.88.

[0176] Synthesis Example 48: Synthesis of Compound E-279

[0177] A 500 mL round-bottom flask was charged with E-8-1 (8.48 mmol, 1 eq) and E-1-2 (38.16 mmol, 4.5 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (135.68 mmol, 16 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-279, was obtained using conventional methods (61% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 1029.25. Elemental analysis showed theoretical values ​​(%): C, 85.19; H, 3.92; N, 10.89. Exp. value (%): C, 85.20; H, 3.91; N, 10.89.

[0178] Synthesis Example 49: Synthesis of Compound E-349

[0179] A 500 mL round-bottom flask was charged with E-9-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-349, was obtained using conventional methods (68% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 677.25. Elemental analysis showed theoretical values ​​(%): C, 86.96; H, 4.76; N, 8.28. Exp. value (%): C, 86.95; H, 4.77; N, 8.28.

[0180] Synthesis Example 50: Synthesis of Compound E-354

[0181] A 500 mL round-bottom flask was charged with E-9-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-354, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 981.25. Elemental analysis showed theoretical values ​​(%): C, 89.36; H, 4.93; N, 5.71. Expected values ​​(%): C, 89.36; H, 4.92; N, 5.72.

[0182] Synthesis Example 51: Synthesis of Compound E-357

[0183] A 500 mL round-bottom flask was charged with E-9-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-357, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 953.25. Elemental analysis: theoretical (%): C, 81.90; H, 6.34; N, 11.76. Exp. values ​​(%): C, 81.90; H, 6.33; N, 11.77.

[0184] Synthesis Example 52: Synthesis of Compound E-421

[0185] A 500 mL round-bottom flask was charged with E-9-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-421, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 629.25. Elemental analysis showed theoretical values ​​(%): C, 85.96; H, 5.13; N, 8.91. Expected values ​​(%): C, 85.97; H, 5.13; N, 8.90.

[0186] Synthesis Example 53: Synthesis of Compound E-424

[0187] A 500 mL round-bottom flask was charged with E-9-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-424, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 781.05. Elemental analysis showed theoretical values ​​(%): C, 87.67; H, 5.16; N, 7.17. Experimental values ​​(%): C, C, 87.66; H, 5.17; N, 7.17.

[0188] Synthesis Example 54: Synthesis of Compound E-427

[0189] A 500 mL round-bottom flask was charged with E-9-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-427, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 905.25. Elemental analysis: theoretical (%): C, 80.94; H, 6.68; N, 12.38. Exp. value (%): C, 80.94; H, 6.69; N, 12.37.

[0190] Synthesis Example 55: Synthesis of Compound E-626

[0191] A 500 mL round-bottom flask was charged with E-10-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-626, was obtained using conventional methods (65% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 673.25. Elemental analysis showed theoretical values ​​(%): C, 87.48; H, 4.20; N, 8.32. Exp. value (%): C, 87.47; H, 4.20; N, 8.33.

[0192] Synthesis Example 56: Synthesis of Compound E-631

[0193] A 500 mL round-bottom flask was charged with E-10-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-631, was obtained using conventional methods (72% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 977.25. Elemental analysis: theoretical (%): C, 89.73; H, 4.54; N, 5.73. Expected values ​​(%): C, 89.74; H, 4.54; N, 5.72.

[0194] Synthesis Example 57: Synthesis of Compound E-634

[0195] A 500 mL round-bottom flask was charged with E-10-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-634, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 949.25. Elemental analysis showed theoretical values ​​(%): C, 82.25; H, 5.95; N, 11.80. Expected values ​​(%): C, 82.24; H, 5.95; N, 11.81.

[0196] Synthesis Example 58: Synthesis of Compound E-644

[0197] A 500 mL round-bottom flask was charged with E-11-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-644, was obtained using conventional methods (64% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 677.25. Elemental analysis showed theoretical values ​​(%): C, 86.96; H, 4.76; N, 8.28. Exp. value (%): C, 86.95; H, 4.77; N, 8.28.

[0198] Synthesis Example 59: Synthesis of Compound E-649

[0199] A 500 mL round-bottom flask was charged with E-11-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-649, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 981.25. Elemental analysis showed theoretical values ​​(%): C, 89.36; H, 4.93; N, 5.71. Expected values ​​(%): C, 89.37; H, 4.93; N, 5.70.

[0200] Synthesis Example 60: Synthesis of Compound E-652

[0201] A 500 mL round-bottom flask was charged with E-11-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-652, was obtained using conventional methods (62% yield, 99.66% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 953.25. Elemental analysis: theoretical (%): C, 81.90; H, 6.34; N, 11.76. Exp. values ​​(%): C, 81.90; H, 6.35; N, 11.75.

[0202] Synthesis Example 61: Synthesis of Compound E-662

[0203] A 500 mL round-bottom flask was charged with E-12-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-662, was obtained using conventional methods (63% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 689.25. Elemental analysis showed theoretical values ​​(%): C, 83.69; H, 4.10; N, 8.13; Si, 4.08. Experimental values ​​(%): C, 83.67; H, 4.10; N, 8.15; Si, 4.08.

[0204] Synthesis Example 62: Synthesis of Compound E-667

[0205] A 500 mL round-bottom flask was charged with E-12-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-667, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 993.25. Elemental analysis: theoretical (%): C, 87.07; H, 4.47; N, 5.64; Si, 2.82. Experimental values ​​(%): C, 87.07; H, 4.47; N, 5.63; Si, 2.83.

[0206] Synthesis Example 63: Synthesis of Compound E-670

[0207] A 500 mL round-bottom flask was charged with E-12-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-670, was obtained using conventional methods (60% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 965.25. Elemental analysis: theoretical (%): C, 79.63; H, 5.85; N, 11.61; Si, 2.91. Experimen tal values ​​(%): C, 79.63; H, 5.84; N, 11.62; Si, 2.91.

[0208] Synthesis Example 64: Synthesis of Compound E-680

[0209] A 500 mL round-bottom flask was charged with E-13-1 (8.48 mmol, 1 eq) and E-1-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-680, was obtained using conventional methods (63% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 693.25. Elemental analysis showed theoretical values ​​(%): C, 83.20; H, 4.66; N, 8.09; Si, 4.05. Experimen tal values ​​(%): C, 83.21; H, 4.66; N, 8.09; Si, 4.04.

[0210] Synthesis Example 65: Synthesis of Compound E-685

[0211] A 500 mL round-bottom flask was charged with E-13-1 (8.48 mmol, 1 eq) and E-2-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-685, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 997.25. Elemental analysis: theoretical (%): C, 86.71; H, 4.85; N, 5.62; Si, 2.82. Experimental values ​​(%): C, 86.72; H, 4.84; N, 5.62; Si, 2.82.

[0212] Synthesis Example 66: Synthesis of Compound E-688

[0213] A 500 mL round-bottom flask was charged with E-13-1 (8.48 mmol, 1 eq) and E-5-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-688, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 969.25. Elemental analysis: theoretical (%): C, 79.30; H, 6.24; N, 11.56; Si, 2.90. Expected values ​​(%): C, 79.30; H, 6.25; N, 11.55; Si, 2.90.

[0214] Synthesis Example 67: Synthesis of Compound E-698

[0215] A 500 mL round-bottom flask was charged with E-10-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-698, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 624.85. Elemental analysis showed theoretical values ​​(%): C, 86.51; H, 4.52; N, 8.97. Exp. value (%): C, 86.52; H, 4.52; N, 8.96.

[0216] Synthesis Example 68: Synthesis of Compound E-702

[0217] A 500 mL round-bottom flask was charged with E-10-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-702, was obtained using conventional methods (62% yield, 99.46% purity by HPLC analysis). MALDI-TOF-MS results revealed m / z: 929.25. Elemental analysis revealed theoretical values ​​(%): C, 89.20; H, 4.77; N, 6.03. Expected values ​​(%): C, 89.20; H, 4.76; N, 6.04.

[0218] Synthesis Example 69: Synthesis of Compound E-705

[0219] A 500 mL round-bottom flask was charged with E-10-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-705, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 901.25. Elemental analysis showed theoretical values ​​(%): C, 81.30; H, 6.27; N, 12.43. Exp. value (%): C, 81.30; H, 6.26; N, 12.44.

[0220] Synthesis Example 70: Synthesis of Compound E-715

[0221] A 500 mL round-bottom flask was charged with E-11-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-715, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 629.25. Elemental analysis showed theoretical values ​​(%): C, 85.96; H, 5.13; N, 8.91. Exp. value (%): C, 85.96; H, 5.14; N, 8.90.

[0222] Synthesis Example 71: Synthesis of Compound E-719

[0223] A 500 mL round-bottom flask was charged with E-11-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-719, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 933.25. Elemental analysis showed theoretical values ​​(%): C, 88.81; H, 5.18; N, 6.00. Exp. value (%): C, 88.81; H, 5.18; N, 6.00.

[0224] Synthesis Example 72: Synthesis of Compound E-722

[0225] A 500 mL round-bottom flask was charged with E-11-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-722, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 905.25. Elemental analysis showed theoretical values ​​(%): C, 80.94; H, 6.68; N, 12.38. Expected values ​​(%): C, 80.92; H, 6.69; N, 12.39.

[0226] Synthesis Example 73: Synthesis of Compound E-732

[0227] A 500 mL round-bottom flask was charged with E-12-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-732, was obtained using conventional methods (60% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 641.25. Elemental analysis showed theoretical values ​​(%): C, 82.47; H, 4.40; N, 8.75; Si, 4.38. Experimen tal values ​​(%): C, 82.48; H, 4.40; N, 8.74; Si, 4.38.

[0228] Synthesis Example 74: Synthesis of Compound E-736

[0229] A 500 mL round-bottom flask was charged with E-12-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-736, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results: m / z: 945.25. Elemental analysis: theoretical (%): C, 86.41; H, 4.69; N, 5.93; Si, 2.97. Experimen tal values ​​(%): C, 86.41; H, 4.69; N, 5.92; Si, 2.98.

[0230] Synthesis Example 75: Synthesis of Compound E-739

[0231] A 500 mL round-bottom flask was charged with E-12-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-739, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results revealed m / z: 917.25. Elemental analysis revealed theoretical values ​​(%): C, 78.57; H, 6.15; N, 12.22; Si, 3.06. Expected values ​​(%): C, 78.58; H, 6.14; N, 12.22; Si, 3.06.

[0232] Synthesis Example 76: Synthesis of Compound E-749

[0233] A 500 mL round-bottom flask was charged with E-13-1 (8.48 mmol, 1 eq) and E-9-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-749, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 645.25. Elemental analysis showed theoretical values ​​(%): C, 81.95; H, 5.00; N, 8.69; Si, 4.36. Experimental values ​​(%): C, 81.94; H, 5.00; N, 8.69; Si, 4.37.

[0234] Synthesis Example 77: Synthesis of Compound E-753

[0235] A 500 mL round-bottom flask was charged with E-13-1 (8.48 mmol, 1 eq) and E-12-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated brine and then ethanol. The final product, E-753, was obtained using conventional methods (61% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 949.25. Elemental analysis showed theoretical values ​​(%): C, 86.04; H, 5.10; N, 5.90; Si, 2.96. Experimental values ​​(%): C, 86.05; H, 5.10; N, 5.90; Si, 2.95.

[0236] Synthesis Example 78: Synthesis of Compound E-756

[0237] A 500 mL round-bottom flask was charged with E-13-1 (8.48 mmol, 1 eq) and E-11-2 (19.08 mmol, 2.25 eq). A mixture of toluene (160 mL), ethanol (60 mL), and deionized water (100 mL) was used as the solvent. Na₂CO₃ (67.84 mmol, 8 eq) and Pd(PPh₃)₄ (1.27 mmol, 0.15 eq) were added as catalysts. The mixture was heated under reflux under nitrogen for 36 hours. After cooling, the reaction mixture was filtered, and the filter cake was rinsed with saturated sodium chloride solution and then ethanol. The final product, E-756, was obtained using conventional methods (62% yield, 99.56% purity by HPLC analysis). MALDI-TOF-MS results showed m / z: 921.25. Elemental analysis showed theoretical values ​​(%): C, 78.22; H, 6.56; N, 12.16; Si, 3.06. Experimen tal values ​​(%): C, 78.22; H, 6.56; N, 12.17; Si, 3.05.

[0238] The technical features and advantages of the present invention are verified and demonstrated by applying the organic materials of the present invention to single-junction OLED devices and tandem OLED devices, respectively, and testing the performance and properties of the devices.

[0239] Preparation of single-junction OLED devices:

[0240] Application examples of the compounds of the present invention, namely, examples of preparing single-junction OLED devices

[0241] An OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material layer can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0242] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate used for the display can also be provided with thin film transistors (TFTs).

[0243] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0244] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0245] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0246] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0247] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds.

[0248] The light-emitting layer includes a luminescent dye (i.e., a dopant) that can emit light at different wavelengths, and may also include a host material. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0249] Depending on the technology, the light-emitting layer material can be made of fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, and other materials. An OLED device can use a single light-emitting technology or a combination of multiple technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0250] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. This region may be a single-layer electron transport layer (ETL), including those containing only one compound and those containing multiple compounds. The region may also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0251] The electron injection layer of the present invention uses an n-type dopant and the o-phenanthroline electron injection material described in the present invention. The n-type dopant is mainly composed of alkali metals, alkaline earth metals and some transition metals and their salts, including but not limited to lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), magnesium (Mg), calcium (Ca), iron (Fe), chromium (Cr), niobium (Nb), cobalt (Co), manganese (Mn), nickel (Ni), copper (Cu), zinc (Zn), silver (Ag), palladium (Pd), rhodium (Rh), ruthenium (Ru), iridium (Ir), tungsten (W), rhenium (Re), platinum (Pt), gold (Au), and ytterbium (Yb). The doping ratio of the metal n-type dopant in the electron injection layer is 0.1wt% to 50wt%, the corresponding doping ratio is 0.01vol%-5vol%, and the preferred doping ratio is 0.05wt% to 20wt%. Its total thickness is 0.1 nm to 20 nm, more preferably 3-5 nm.

[0252] The preparation process of the single-junction organic electroluminescent device in the embodiment is as follows:

[0253] Glass plates coated with an ITO transparent conductive layer were ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0254] Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~5×10 -4 Pa, vacuum evaporating HATCN as a hole injection layer on the above anode layer film, the evaporation rate is 0.05nm / s, and the evaporation film thickness is 5nm;

[0255] NPB was vacuum evaporated on the hole injection layer as the hole transport layer of the device at a deposition rate of 0.1 nm / s and a total film thickness of 30 nm.

[0256] The electron blocking layer and light-emitting layer of the device are vacuum-deposited on top of the hole transport layer. The light-emitting layer of the present invention includes a host material and a dye material. Multi-source co-evaporation is used for doping, and the rate and doping concentration are controlled using high and low crystal oscillator probes. The evaporation rate of the host material is adjusted to 0.1 nm / s, and the evaporation rate of the dye in the light-emitting layer is adjusted to 1%-5% of the host evaporation rate to achieve the desired doping ratio. The total thickness of the light-emitting layer is 20-50 nm.

[0257] Vacuum-deposit the hole blocking layer and electron transport layer materials of the device on the light-emitting layer at a rate of 0.1 nm / s and a total film thickness of 20-60 nm;

[0258] Metal Ag and the o-phenanthroline compound of the specific structure of the present invention are simultaneously evaporated on the electron transport layer (ETL) to form an electron injection layer. In-situ doping is achieved by adjusting the evaporation rates of each, wherein the evaporation rate ratio of metal Ag and organic material is 1%-10% (i.e., the volume fraction is between 0.1 vol% and 1 vol%), and the total thickness of the electron injection layer is controlled to be 5 nm.

[0259] Finally, 150 nm of Al was vacuum evaporated on the electron injection layer as the cathode of the device.

[0260] Device Example 1

[0261] In this embodiment, a 5nm thick Ag:E-1 (the evaporation rate ratio of the two is 3%) is used as the electron injection layer, and a 150nm thick Al layer is used as the cathode of the device. The structure is as follows:

[0262] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-1(5nm) / Al(150nm).

[0263] Device Example 2

[0264] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-6 instead of E-1, and the Ag:E-6 evaporation rate ratio is 3%. The device structure is as follows:

[0265] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-6(5nm) / Al(150nm).

[0266] Device Example 3

[0267] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-7 instead of E-1, and the evaporation rate ratio of Ag:E-7 is 3%. The device structure is as follows:

[0268] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-7(5nm) / Al(150nm).

[0269] Device Example 4

[0270] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-8 instead of E-1, and the Ag:E-8 evaporation rate ratio is 3%. The device structure is as follows:

[0271] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-8(5nm) / Al(150nm).

[0272] Device Example 5

[0273] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-9 instead of E-1, and the evaporation rate ratio of Ag:E-9 is 3%. The device structure is as follows:

[0274] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-9(5nm) / Al(150nm).

[0275] Device Example 6

[0276] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-16 instead of E-1, and the evaporation rate ratio of Ag:E-16 is 3%. The device structure is as follows:

[0277] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-16(5nm) / Al(150nm).

[0278] Device Example 7

[0279] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-17 instead of E-1, and the evaporation rate ratio of Ag:E-17 is 3%. The device structure is as follows:

[0280] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-17(5nm) / Al(150nm).

[0281] Device Example 8

[0282] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-18 instead of E-1, and the evaporation rate ratio of Ag:E-18 is 3%. The device structure is as follows:

[0283] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-18(5nm) / Al(150nm).

[0284] Device Example 9

[0285] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-19 instead of E-1, and the evaporation rate ratio of Ag:E-19 is 3%. The device structure is as follows:

[0286] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-19(5nm) / Al(150nm).

[0287] Device Example 10

[0288] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-37 instead of E-1, and the evaporation rate ratio of Ag:E-37 is 3%. The device structure is as follows:

[0289] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-37(5nm) / Al(150nm).

[0290] Device Example 11

[0291] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-42 instead of E-1, and the evaporation rate ratio of Ag:E-42 is 3%. The device structure is as follows:

[0292] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-42(5nm) / Al(150nm).

[0293] Device Example 12

[0294] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-45 instead of E-1, and the evaporation rate ratio of Ag:E-45 is 3%. The device structure is as follows:

[0295] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-45(5nm) / Al(150nm).

[0296] Device Example 13

[0297] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-55 instead of E-1, and the evaporation rate ratio of Ag:E-55 is 3%. The device structure is as follows:

[0298] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-55(5nm) / Al(150nm).

[0299] Device Example 14

[0300] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-73 instead of E-1, and the evaporation rate ratio of Ag:E-73 is 3%. The device structure is as follows:

[0301] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-73(5nm) / Al(150nm).

[0302] Device Example 15

[0303] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-91 instead of E-1, and the evaporation rate ratio of Ag:E-91 is 3%. The device structure is as follows:

[0304] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-91(5nm) / Al(150nm).

[0305] Device Example 16

[0306] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-109 instead of E-1, and the evaporation rate ratio of Ag:E-109 is 3%. The device structure is as follows:

[0307] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-109(5nm) / Al(150nm).

[0308] Device Example 17

[0309] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-115, and the Ag:E-115 evaporation rate ratio is 3%. The device structure is as follows:

[0310] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-115(5nm) / Al(150nm).

[0311] Device Example 18

[0312] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-125 instead of E-1, and the evaporation rate ratio of Ag:E-125 is 3%. The device structure is as follows:

[0313] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-125(5nm) / Al(150nm).

[0314] Device Example 19

[0315] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-142, and the evaporation rate ratio of Ag:E-142 is 3%. The device structure is as follows:

[0316] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-142(5nm) / Al(150nm).

[0317] Device Example 20

[0318] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-148, and the Ag:E-148 evaporation rate ratio is 3%. The device structure is as follows:

[0319] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-148(5nm) / Al(150nm).

[0320] Device Example 21

[0321] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-158, and the evaporation rate ratio of Ag:E-158 is 3%. The device structure is as follows:

[0322] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-158(5nm) / Al(150nm).

[0323] Device Example 22

[0324] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-175 instead of E-1, and the evaporation rate ratio of Ag:E-175 is 3%. The device structure is as follows:

[0325] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-175(5nm) / Al(150nm).

[0326] Device Example 23

[0327] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-192 instead of E-1, and the evaporation rate ratio of Ag:E-192 is 3%. The device structure is as follows:

[0328] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-192(5nm) / Al(150nm).

[0329] Device Example 24

[0330] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-209 instead of E-1, and the evaporation rate ratio of Ag:E-209 is 3%. The device structure is as follows:

[0331] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-209(5nm) / Al(150nm).

[0332] Device Example 25

[0333] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-279 instead of E-1, and the evaporation rate ratio of Ag:E-279 is 3%. The device structure is as follows:

[0334] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-279(5nm) / Al(150nm).

[0335] Device Example 26

[0336] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-349 instead of E-1, and the evaporation rate ratio of Ag:E-349 is 3%. The device structure is as follows:

[0337] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-349(5nm) / Al(150nm).

[0338] Device Example 27

[0339] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-357 instead of E-1, and the evaporation rate ratio of Ag:E-357 is 3%. The device structure is as follows:

[0340] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-357(5nm) / Al(150nm).

[0341] Device Example 28

[0342] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-421 instead of E-1, and the evaporation rate ratio of Ag:E-421 is 3%. The device structure is as follows:

[0343] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-421(5nm) / Al(150nm).

[0344] Device Example 29

[0345] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-427 instead of E-1, and the evaporation rate ratio of Ag:E-427 is 3%. The device structure is as follows:

[0346] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-427(5nm) / Al(150nm).

[0347] Device Example 30

[0348] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-626 instead of E-1, and the evaporation rate ratio of Ag:E-626 is 3%. The device structure is as follows:

[0349] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-626(5nm) / Al(150nm).

[0350] Device Example 31

[0351] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-631 instead of E-1, and the evaporation rate ratio of Ag:E-631 is 3%. The device structure is as follows:

[0352] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-631(5nm) / Al(150nm).

[0353] Device Example 32

[0354] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-634 instead of E-1, and the evaporation rate ratio of Ag:E-634 is 3%. The device structure is as follows:

[0355] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-634(5nm) / Al(150nm).

[0356] Device Example 33

[0357] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-644 instead of E-1, and the evaporation rate ratio of Ag:E-644 is 3%. The device structure is as follows:

[0358] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-644(5nm) / Al(150nm).

[0359] Device Example 34

[0360] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-652 instead of E-1, and the evaporation rate ratio of Ag:E-652 is 3%. The device structure is as follows:

[0361] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-652(5nm) / Al(150nm).

[0362] Device Example 35

[0363] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-662 instead of E-1, and the evaporation rate ratio of Ag:E-662 is 3%. The device structure is as follows:

[0364] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-662(5nm) / Al(150nm).

[0365] Device Example 36

[0366] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-667 instead of E-1, and the evaporation rate ratio of Ag:E-667 is 3%. The device structure is as follows:

[0367] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%, 30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-667(5nm) / Al(150nm).

[0368] Device Example 37

[0369] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-670 instead of E-1, and the evaporation rate ratio of Ag:E-670 is 3%. The device structure is as follows:

[0370] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-670(5nm) / Al(150nm).

[0371] Device Example 38

[0372] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-680 instead of E-1, and the evaporation rate ratio of Ag:E-680 is 3%. The device structure is as follows:

[0373] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-680(5nm) / Al(150nm).

[0374] Device Example 39

[0375] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-698 instead of E-1, and the evaporation rate ratio of Ag:E-698 is 3%. The device structure is as follows:

[0376] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-698(5nm) / Al(150nm).

[0377] Device Example 40

[0378] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-705 instead of E-1, and the evaporation rate ratio of Ag:E-705 is 3%. The device structure is as follows:

[0379] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-705(5nm) / Al(150nm).

[0380] Device Example 41

[0381] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-715 instead of E-1, and the evaporation rate ratio of Ag:E-715 is 3%. The device structure is as follows:

[0382] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-715(5nm) / Al(150nm).

[0383] Device Example 42

[0384] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-722 instead of E-1, and the evaporation rate ratio of Ag:E-722 is 3%. The device structure is as follows:

[0385] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-722(5nm) / Al(150nm).

[0386] Device Example 43

[0387] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-732 instead of E-1, and the evaporation rate ratio of Ag:E-732 is 3%. The device structure is as follows:

[0388] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-732(5nm) / Al(150nm).

[0389] Device Example 44

[0390] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-739 instead of E-1, and the evaporation rate ratio of Ag:E-739 is 3%. The device structure is as follows:

[0391] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-739(5nm) / Al(150nm).

[0392] Device Example 45

[0393] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by E-749 instead of E-1, and the evaporation rate ratio of Ag:E-749 is 3%. The device structure is as follows:

[0394] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:E-749(5nm) / Al(150nm).

[0395] Device Example 46

[0396] The preparation method is the same as that of Example 1, except that the doping metal is replaced by Yb instead of Ag, and the Yb:E-1 evaporation rate ratio is 3%. The device structure is as follows:

[0397] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Yb:E-1(5nm) / Al(150nm).

[0398] Device Example 47

[0399] The preparation method is the same as that of Example 1, except that the doping metal is replaced by Zn instead of Ag, and the Zn:E-1 evaporation rate ratio is 3%. The device structure is as follows:

[0400] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Zn:E-1(5nm) / Al(150nm).

[0401] Device Example 48

[0402] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by Yb:E-9 instead of Ag:E-1, and the Yb:E-9 evaporation rate ratio is 3%. The device structure is as follows:

[0403] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Yb:E-9(5nm) / Al(150nm).

[0404] Device Example 49

[0405] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by Zn:E-9 instead of Ag:E-1, and the Zn:E-9 evaporation rate ratio is 3%. The device structure is as follows:

[0406] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Zn:E-9(5nm) / Al(150nm).

[0407] Device Example 50

[0408] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by Yb:E-626 instead of Ag:E-1, and the Yb:E-626 evaporation rate ratio is 3%. The device structure is as follows:

[0409] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Yb:E-626(5nm) / Al(150nm).

[0410] Device Example 51

[0411] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by Zn:E-626 instead of Ag:E-1, and the Zn:E-626 evaporation rate ratio is 3%. The device structure is as follows:

[0412] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Zn:E-626(5nm) / Al(150nm).

[0413] Device Example 52

[0414] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by Yb:E-634 instead of Ag:E-1, and the Yb:E-634 evaporation rate ratio is 3%. The device structure is as follows:

[0415] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Yb:E-634(5nm) / Al(150nm).

[0416] Device Example 53

[0417] The preparation method is the same as that of Example 1, except that the electron injection layer material is replaced by Zn:E-634 instead of Ag:E-1, and the Zn:E-634 evaporation rate ratio is 3%. The device structure is as follows:

[0418] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Zn:E-634(5nm) / Al(150nm).

[0419] Comparative Device Example 1

[0420] The preparation method is the same as that of Example 1, except that the electron injection material is replaced by Ag:E-1 with the compound Cs2CO3 in the prior art, that is, the electron injection layer adopts Cs2CO3:E-1 (5nm) where the evaporation rate ratio of Cs2CO3:E-1 is 10%.

[0421] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%, 30nm) / HBL(10nm) / DPPyA(20nm) / Cs2CO3:E-1(10%, 5nm) / Al(150nm).

[0422] Comparative Device Example 2

[0423] The preparation method is the same as that of Example 1, except that the electron injection layer is replaced by Ag:E-1 (5 nm) with the compound LiF (1 nm) in the prior art.

[0424] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / LiF(1nm) / Al(150nm).

[0425] Comparative Device Example 3

[0426] The preparation method is the same as that of Example 1, except that the electron injection layer is replaced by Ag:E-1 (5 nm) with the compound Liq (1 nm) in the prior art.

[0427] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Liq(1nm) / Al(150nm).

[0428] Comparative Device Example 4

[0429] The preparation method is the same as that of Example 1, except that the electron injection layer is replaced by Ag:E-1 (5 nm) with the prior art compound Ag:D-1. The Ag:D-1 evaporation rate ratio is 10%. The device structure is as follows:

[0430] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:D-1(5nm) / Al(150nm).

[0431] Comparative Device Example 5

[0432] The preparation method is the same as that of Example 1, except that the electron injection layer is replaced by the prior art compound D-2 instead of Ag:E-1 (5 nm). The Ag:D-2 evaporation rate ratio is 10%, and the thickness is 5 nm. The device structure is as follows:

[0433] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Ag:D-2(5nm) / Al(150nm).

[0434] Comparative Device Example 6

[0435] The preparation method is the same as that of Example 1, except that the electron injection layer is replaced with the prior art compound Yb:D-2 instead of Ag:E-1 (5 nm). The Yb:D-2 evaporation rate ratio is 10%. The device structure is as follows:

[0436] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Yb:D-2(5nm) / Al(150nm).

[0437] Comparative Device Example 7

[0438] The preparation method is the same as that of Example 1, except that the electron injection layer is replaced by the prior art compound Zn:D-2 instead of Ag:E-1 (5 nm). The Zn:D-2 evaporation rate ratio is 10%. The device structure is as follows:

[0439] ITO / HATCN(5nm) / NPB(30nm) / EBL(10nm) / t-DABNA:α,β-ADN(2%,30nm) / HBL(10nm) / DPPyA(20nm) / Zn:D-2(5nm) / Al(150nm).

[0440] The performance of the organic electroluminescent devices prepared in the above device examples and comparative device examples is shown in Table 1 below.

[0441] Table 1:

[0442] From Table 1, it can be found by Examples 5, 6, 8, 46, 47 and Comparative Examples 1 to 3 that, in the case of the same other materials in the organic electroluminescent device structure, the voltage of the OLED device prepared by the compound of the present invention compared to the prior art compound in Comparative Examples 1 to 3 is all reduced, and the efficiency of the device is significantly improved, and the life-span of the device is correspondingly improved. It is speculated that the present invention should be when using alkali metal compounds as injection materials, in the process of heating evaporation and in the device operation, alkali metal ions may migrate or diffuse, thereby causing the exciton quenching in the luminescent layer, thereby causing efficiency and life-span to decline. And transition metal n-type dopants such as Ag and o-phenanthroline organic ligands have stronger interactions, which contribute to suppressing the migration or diffusion of metal. In addition, the injection performance of the electron injection layer prepared by the doping strategy based on transition metal coordination is better, thereby helping to improve the efficiency and life-span of exciton utilization and OLED devices.

[0443] The prior art compound D1 used in Comparative Example 4 is 4,7-diphenylphenanthroline (Bphen), a commonly used electron transport material. It has excellent coordination properties and, after being doped with Ag, can serve as a highly efficient electron injection layer in conventional techniques. However, this compound has a molecular weight of only 332.41, resulting in a glass transition temperature of only 62°C. This poorly stabilizes the film, resulting in a relatively short lifetime in Comparative Example 4.

[0444] The prior art compound D2 used in comparative example 5 is a commonly used electron transmission material. By comparing with Example 1 using compound E-1 of the present invention, it can be found that since E1 replaces the bridging group by a benzene ring with a spirofluorene group having stronger transmission performance, it is more conducive to electron transmission. The electron injection performance of Ag:E1, Yb:E1, Zn:E1, etc. as electron injection layer materials is significantly better than that of Ag:D2, Yb:D2, and Zn:D2. Compared to D2, the driving voltage of the device using E1 as an organic ligand is lower, and current efficiency is higher, and the life of the device is also improved. Further comparing Example 1 and Example 2 to Example 8, it can be found that when the skeleton groups are consistent, the electron-donating performance of R1 and R2 is stronger, and the coordination performance of the corresponding phenanthroline ligand is stronger, and the performance of the electron injection layer prepared accordingly is better, and then significantly reduces the driving voltage of the device, improves the efficiency and life of the device. This also reflects that the selection of R1 and R2 in the core structure of the compound of the present invention has an important influence on the performance of this type of phenanthroline material in combination with transition metal as an electron injection layer.

[0445] In summary, the poly-o-phenanthroline electron injection material of the present invention has a large molecular weight and exhibits good film stability after being doped with n-type dopants such as Ag, Yb, and Zn. By optimizing the molecular structure, its coordination properties can be regulated. When used with n-type dopants such as Ag, Yb, and Zn as an electron injection layer, it can achieve a low work function and excellent electron injection performance. Therefore, it can be used in OLED devices to achieve both high efficiency and a long life.

[0446] Preparation of tandem OLED devices:

[0447] The technical features and advantages of the present invention will be demonstrated and verified below by applying the actual application effect of the connecting layer described in the present invention in a tandem organic electroluminescent device and by testing the performance and properties of the device.

[0448] A tandem OLED device consists of an anode, a cathode, and an organic material layer between the two electrodes. This organic material layer can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0449] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate used for the display can also be provided with thin film transistors (TFTs).

[0450] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0451] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0452] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0453] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0454] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds.

[0455] The light-emitting layer includes a luminescent dye (i.e., dopant) that can emit light at different wavelengths, and may also include a host material. Depending on the technology, the light-emitting layer material can be made of different materials, such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. In a tandem OLED device, a single light-emitting technology or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials, classified by technology, can emit light of the same color or different colors.

[0456] The OLED organic material layer also includes an electron transport region. This region can be a single-layer electron transport layer (ETL), i.e., a single-layer ETL containing only one compound or a single-layer ETL containing multiple compounds. Alternatively, the ETL can be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0457] In the tandem OLED device described herein, each light-emitting unit comprises a hole transport region, a light-emitting layer, and an electron transport region. Multiple light-emitting units are connected in series via a connecting layer. Each light-emitting unit can be a single-color light-emitting unit emitting a single color, such as red, green, or blue; a single-color light-emitting unit emitting different colors, such as red, green, and blue; or a single-color light-emitting layer capable of emitting different colors, such as red, green, and blue, simultaneously.

[0458] The connecting layer in the tandem OLED device described in the present invention is shown in Figure 1. The first light-emitting unit is prepared on the anode of the device, and the connecting layer 1 of the device is prepared between the first light-emitting unit and the second light-emitting unit. The connecting layer structure is n-type doped layer / n-type layer / p-type layer. Then, the connecting layer 2 and the third light-emitting unit are prepared on the second light-emitting unit. According to the design requirements of the device structure, N-1 connecting layers can be prepared accordingly until the Nth light-emitting unit is prepared, and finally the cathode of the device is completed.

[0459] The n-type doping layer mainly uses an n-type dopant and the o-phenanthroline electron injection material described in the present invention. The n-type dopant is mainly composed of alkali metals, alkaline earth metals and some transition metals and their salts, including but not limited to lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), magnesium (Mg), calcium (Ca), iron (Fe), chromium (Cr), niobium (Nb), cobalt (Co), manganese (Mn), nickel (Ni), copper (Cu), zinc (Zn), silver (Ag), palladium (Pd), rhodium (Rh), ruthenium (Ru), iridium (Ir), tungsten (W), rhenium (Re), platinum (Pt), gold (Au), ytterbium (Yb) or a mixture of several thereof. The doping ratio of the metal n-type dopant in the n-type doping layer is 0.1wt% to 50wt%, the corresponding doping ratio is 0.01vol%-5vol%, and the preferred doping ratio is 0.05wt% to 20wt%. The total thickness thereof is 0.1 nm to 20 nm, more preferably 1-10 nm.

[0460] The n-type layer includes but is not limited to HATCN etc.

[0461] The p-type layer mainly uses organic materials with hole transport properties, including but not limited to NPB, TAPC, TCTA, spiro-TAD, mCP, TPTE, BFA-IT, TDAB, TDAPB, PTDATA, 2-TNATA, mCBP, etc.

[0462] The preparation process of the tandem organic electroluminescent device in the embodiment of the present invention is as follows:

[0463] Specifically, the tandem OLED device used in this experiment is a dual-emission layer device with a connecting layer. The device preparation process is as follows: a glass plate coated with an ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixture, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0464] Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~5×10 -4 Pa, vacuum evaporating HATCN as a hole injection layer on the above-mentioned anode layer film at a evaporation rate of 0.05 nm / s and a film thickness of 5 to 10 nm;

[0465] Vacuum evaporate NPB on the hole injection layer as the hole transport layer of the device at a deposition rate of 0.1 nm / s and a total film thickness of 30 to 50 nm;

[0466] The light-emitting layer of the device is vacuum-deposited on top of the hole transport layer. The light-emitting layer of the present invention includes the host material Be(bq)2 and the phosphorescent dye Ir(mphmq)2(tmd). Multi-source co-evaporation is used for doping, and the rate and doping concentration are controlled using high and low crystal oscillator probes. The evaporation rate of the host material is adjusted to 0.1 nm / s, and the evaporation rate of the dye in the light-emitting layer is adjusted to 1% to 5% of the host evaporation rate to achieve the desired doping ratio. The total thickness of the light-emitting layer is 20 to 50 nm.

[0467] Vacuum-deposit DPPyA as an electron transport layer material on the light-emitting layer at a rate of 0.1 nm / s and a total film thickness of 20 to 60 nm;

[0468] A connecting layer with a total thickness of 20 to 10 nm is vacuum-evaporated on the electron transport layer (ETL). The n-type doping layer includes metallic Ag and a phenanthroline compound of the specific structure of the present invention. In-situ doping is achieved by adjusting the respective evaporation rates. The evaporation rate ratio of the metallic Ag to the organic material is 1%-10% (i.e., the volume fraction is between 0.1 vol% and 1 vol%). The thickness is 10 nm. The n-type layer is HATCN with a thickness of 10 nm, and the p-type layer is NPB with a thickness of 75 nm.

[0469] On the connecting layer, a light-emitting layer with a total thickness of 20 to 50 nm and an electron transport layer with a thickness of 20 to 60 nm are vacuum-deposited. On the electron transport layer (ETL), metallic Ag and a phenanthroline compound of the present invention with a specific structure are simultaneously evaporated to form an electron injection layer. In-situ doping is achieved by adjusting the respective evaporation rates. The ratio of the evaporation rates of metallic Ag and the organic material is 1%-10% (i.e., the volume fraction is between 0.1 vol% and 1 vol%). The total thickness of the electron injection layer is controlled to be 5 nm. Finally, 150 nm of Al is vacuum-evaporated on the electron injection layer as the device's cathode. A dual-light-emitting layer tandem OLED device is then fabricated.

[0470] Table 2 below lists the organic compounds and structural formulas used in the tandem OLED devices prepared in the embodiments of the present invention.

[0471] Table 2:

[0472] Device Example 54

[0473] In this embodiment, 10 nm of Ag:E-1 (the evaporation rate ratio of the two is 3%) is used as the n-type doping layer in the connection layer, and 5 nm of Ag:E-1 (the evaporation rate ratio of the two is 3%) is used as the electron injection layer. The structure is as follows:

[0474] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-1(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-1(3%,5nm) / / Al(150nm)

[0475] Device Example 55

[0476] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-6, and the Ag:E-6 evaporation rate ratio is 3%. The device structure is as follows:

[0477] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-6(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-6(3%,5nm) / Al(150nm)

[0478] Device Example 56

[0479] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-7, and the Ag:E-7 evaporation rate ratio is 3%. The device structure is as follows:

[0480] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-7(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Ag:E-7(3%, 5nm) / Al(150nm).

[0481] Device Example 57

[0482] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-8, and the Ag:E-8 evaporation rate ratio is 3%. The device structure is as follows:

[0483] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-8(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-8(3%,5nm) / Al(150nm)

[0484] Device Example 58

[0485] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-9, and the Ag:E-9 evaporation rate ratio is 3%. The device structure is as follows:

[0486] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-9(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-9(3%,5nm) / Al(150nm)

[0487] Device Example 59

[0488] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-16, and the Ag:E-16 evaporation rate ratio is 3%. The device structure is as follows:

[0489] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-16(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-16(3%,5nm) / Al(150nm)

[0490] Device Example 60

[0491] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-17, and the Ag:E-17 evaporation rate ratio is 3%. The device structure is as follows:

[0492] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-17(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-17(3%,5nm) / Al(150nm)

[0493] Device Example 61

[0494] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-18, and the Ag:E-18 evaporation rate ratio is 3%. The device structure is as follows:

[0495] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-18(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-18(3%,5nm) / Al(150nm)

[0496] Device Example 62

[0497] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-19, and the Ag:E-19 evaporation rate ratio is 3%. The device structure is as follows:

[0498] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-19(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-19(3%,5nm) / Al(150nm)

[0499] Device Example 63

[0500] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-37, and the Ag:E-37 evaporation rate ratio is 3%. The device structure is as follows:

[0501] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-37(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-37(3%,5nm) / Al(150nm)

[0502] Device Example 64

[0503] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-42 and the deposition rate ratio is 3%. The device structure is as follows:

[0504] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-42(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-42(3%,5nm) / Al(150nm)

[0505] Device Example 65

[0506] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-45, and the Ag:E-45 evaporation rate ratio is 3%. The device structure is as follows:

[0507] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-45(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-45(3%,5nm) / Al(150nm)

[0508] Device Example 66

[0509] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-55 and Ag:E-6 at a 3% evaporation rate ratio. The device structure is as follows:

[0510] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-55(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-55(3%,5nm) / Al(150nm)

[0511] Device Example 57

[0512] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-73, and the Ag:E-73 evaporation rate ratio is 3%. The device structure is as follows:

[0513] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-73(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-73(3%,5nm) / Al(150nm)

[0514] Device Example 68

[0515] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-91, and the Ag:E-91 evaporation rate ratio is 3%. The device structure is as follows:

[0516] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-91(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-91(3%,5nm) / Al(150nm)

[0517] Device Example 69

[0518] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-109, and the Ag:E-109 evaporation rate ratio is 3%. The device structure is as follows:

[0519] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-109(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-109(3%,5nm) / Al(150nm)

[0520] Device Example 70

[0521] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-115, and the Ag:E-115 evaporation rate ratio is 3%. The device structure is as follows:

[0522] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-115(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-115(3%,5nm) / Al(150nm)

[0523] Device Example 71

[0524] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-125, and the Ag:E-125 evaporation rate ratio is 3%. The device structure is as follows:

[0525] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-125(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-125(3%,5nm) / Al(150nm)

[0526] Device Example 72

[0527] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-142, and the Ag:E-142 evaporation rate ratio is 3%. The device structure is as follows:

[0528] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-142(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-142(3%,5nm) / Al(150nm)

[0529] Device Example 73

[0530] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-148, and the Ag:E-148 evaporation rate ratio is 3%. The device structure is as follows:

[0531] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-148(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-148(3%,5nm) / Al(150nm)

[0532] Device Example 74

[0533] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-158, and the Ag:E-158 evaporation rate ratio is 3%. The device structure is as follows:

[0534] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-158(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-158(3%,5nm) / Al(150nm)

[0535] Device Example 75

[0536] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-175, and the Ag:E-175 evaporation rate ratio is 3%. The device structure is as follows:

[0537] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-175(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-175(3%,5nm) / Al(150nm)

[0538] Device Example 76

[0539] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-192, and the Ag:E-192 evaporation rate ratio is 3%. The device structure is as follows:

[0540] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-192(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-192(3%,5nm) / Al(150nm)

[0541] Device Example 77

[0542] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-209, and the Ag:E-209 evaporation rate ratio is 3%. The device structure is as follows:

[0543] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-209(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-209(3%,5nm) / Al(150nm)

[0544] Device Example 78

[0545] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-279, and the Ag:E-279 evaporation rate ratio is 3%. The device structure is as follows:

[0546] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-279(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-279(3%,5nm) / Al(150nm)

[0547] Device Example 79

[0548] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-349, and the Ag:E-349 evaporation rate ratio is 3%. The device structure is as follows:

[0549] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-349(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-349(3%,5nm) / Al(150nm)

[0550] Device Example 80

[0551] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-357, and the Ag:E-357 evaporation rate ratio is 3%. The device structure is as follows:

[0552] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-357(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-357(3%,5nm) / Al(150nm)

[0553] Device Example 81

[0554] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-421, and the Ag:E-421 evaporation rate ratio is 3%. The device structure is as follows:

[0555] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-421(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-421(3%,5nm) / Al(150nm)

[0556] Device Example 82

[0557] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-427, and the Ag:E-427 evaporation rate ratio is 3%. The device structure is as follows:

[0558] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-427(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-427(3%,5nm) / Al(150nm)

[0559] Device Example 83

[0560] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-626, and the Ag:E-626 evaporation rate ratio is 3%. The device structure is as follows:

[0561] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-626(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-626(3%,5nm) / Al(150nm)

[0562] Device Example 84

[0563] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-631, and the Ag:E-631 evaporation rate ratio is 3%. The device structure is as follows:

[0564] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-631(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-631(3%,5nm) / Al(150nm)

[0565] Device Example 85

[0566] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-634, and the Ag:E-634 evaporation rate ratio is 3%. The device structure is as follows:

[0567] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-634(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-634(3%,5nm) / Al(150nm)

[0568] Device Example 86

[0569] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-644, and the Ag:E-644 evaporation rate ratio is 3%. The device structure is as follows:

[0570] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-644(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-644(3%,5nm) / Al(150nm)

[0571] Device Example 87

[0572] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-652, and the Ag:E-652 evaporation rate ratio is 3%. The device structure is as follows:

[0573] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-652(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-652(3%,5nm) / Al(150nm)

[0574] Device Example 88

[0575] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-662, and the Ag:E-662 evaporation rate ratio is 3%. The device structure is as follows:

[0576] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-662(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-662(3%,5nm) / Al(150nm)

[0577] Device Example 89

[0578] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-667, and the Ag:E-667 evaporation rate ratio is 3%. The device structure is as follows:

[0579] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-667(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-667(3%,5nm) / Al(150nm)

[0580] Device Example 90

[0581] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-670, and the Ag:E-670 evaporation rate ratio is 3%. The device structure is as follows:

[0582] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-670(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-670(3%,5nm) / Al(150nm)

[0583] Device Example 91

[0584] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-680, and the Ag:E-680 evaporation rate ratio is 3%. The device structure is as follows:

[0585] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-680(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-680(3%,5nm) / Al(150nm)

[0586] Device Example 92

[0587] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-698. The deposition rate ratio of Ag:E-698 is 3%. The device structure is as follows:

[0588] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-698(3%,10nm) / H ATCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-698(3%,5nm) / Al(150 nm)

[0589] Device Example 93

[0590] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-705, and the Ag:E-705 evaporation rate ratio is 3%. The device structure is as follows:

[0591] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-705(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-705(3%,5nm) / Al(150nm)

[0592] Device Example 94

[0593] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-715, and the Ag:E-715 evaporation rate ratio is 3%. The device structure is as follows:

[0594] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-715(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-715(3%,5nm) / Al(150nm)

[0595] Device Example 95

[0596] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-722, and the Ag:E-722 evaporation rate ratio is 3%. The device structure is as follows:

[0597] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-722(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-722(3%,5nm) / Al(150nm)

[0598] Device Example 96

[0599] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-732, and the Ag:E-732 evaporation rate ratio is 3%. The device structure is as follows:

[0600] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-732(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-732(3%,5nm) / Al(150nm)

[0601] Device Example 97

[0602] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-739, and the Ag:E-739 evaporation rate ratio is 3%. The device structure is as follows:

[0603] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-739(3%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-739(3%,5nm) / Al(150nm)

[0604] Device Example 98

[0605] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Ag:E-749, and the Ag:E-749 evaporation rate ratio is 3%. The device structure is as follows:

[0606] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-749(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Ag:E-749(3%, 5nm) / Al(150nm).

[0607] Device Example 99

[0608] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Yb:E-1, and the Yb:E-1 evaporation rate ratio is 3%. The device structure is as follows:

[0609] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Yb:E-1(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Yb:E-1(3%, 5nm) / Al(150nm).

[0610] Device Example 100

[0611] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Zn:E-1, and the Zn:E-1 evaporation rate ratio is 3%. The device structure is as follows:

[0612] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Zn:E-1(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Zn:E-1(3%, 5nm) / Al(150nm).

[0613] Device Example 101

[0614] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Yb:E-9, and the Yb:E-9 evaporation rate ratio is 3%. The device structure is as follows:

[0615] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Yb:E-9(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Yb:E-9(3%, 5nm) / Al(150nm).

[0616] Device Example 102

[0617] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Zn:E-9, and the Zn:E-9 evaporation rate ratio is 3%. The device structure is as follows:

[0618] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Zn:E-9(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Zn:E-9(3%, 5nm) / Al(150nm).

[0619] Device Example 103

[0620] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Yb:E-626, and the Yb:E-626 evaporation rate ratio is 3%. The device structure is as follows:

[0621] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Yb:E-626(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Yb:E-626(3%, 5nm) / Al(150nm).

[0622] Device Example 104

[0623] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Zn:E-626, and the Zn:E-626 evaporation rate ratio is 3%. The device structure is as follows:

[0624] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Zn:E-626(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Zn:E-626(3%, 5nm) / Al(150nm).

[0625] Device Example 105

[0626] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Yb:E-634, and the Yb:E-634 evaporation rate ratio is 3%. The device structure is as follows:

[0627] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Yb:E-634(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Yb:E-634(3%, 5nm) / Al(150nm).

[0628] Device Example 106

[0629] The preparation method is the same as that of Example 54, except that the n-type doping layer and electron injection layer materials are replaced with Zn:E-634, and the Zn:E-634 evaporation rate ratio is 3%. The device structure is as follows:

[0630] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Zn:E-634(3%,10nm) / HAT CN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%, 24nm) / DPPyA(40nm) / Zn:E-634(3%, 5nm) / Al(150nm).

[0631] Comparative Device Example 8

[0632] The preparation method is the same as that of Example 46, except that the n-type dopant of the n-type doping layer and the electron injection layer is replaced by Cs2CO3, wherein the evaporation rate ratio of Cs2CO3:E-1 is 10%. The device structure is as follows:

[0633] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Cs2CO3:E-1(10%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Cs2CO3:E-1(10%,5nm) / Al(150nm)

[0634] Comparative Device Example 9

[0635] The preparation method is the same as that of Example 46, except that the electron injection layer material is replaced with the prior art compound LiF (1 nm). The device structure is as follows:

[0636] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-1(3%,10nm) / HATCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / LiF(1nm) / Al(150nm)

[0637] Comparative Device Example 10

[0638] The preparation method is the same as that of Example 46, except that the electron injection layer material is replaced with the prior art compound Liq (1 nm). The device structure is as follows:

[0639] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:E-1(3%,10nm) / HATCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Liq(1nm) / Al(150nm)

[0640] Comparative Device Example 11

[0641] The preparation method is the same as that of Example 46, except that the n-type doping layer and electron injection layer materials are replaced with Ag:D-1, and the Ag:D-1 evaporation rate ratio is 10%. The device structure is as follows:

[0642] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:D-1(10%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:D-1(10%,5nm) / Al(150nm)

[0643] Comparative Device Example 12

[0644] The preparation method is the same as that of Example 46, except that the n-type doping layer and electron injection layer materials are replaced with Ag:D-2, and the Ag:D-2 evaporation rate ratio is 10%. The device structure is as follows:

[0645] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:D-2(10%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Ag:D-2(10%,5nm) / Al(150nm)

[0646] Comparative Device Example 13

[0647] The preparation method is the same as that of Example 46, except that the n-type doping layer and electron injection layer materials are replaced with Yb:D-2, and the Yb:D-2 evaporation rate ratio is 10%. The device structure is as follows:

[0648] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Yb:D-2(10%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Yb:D-2(10%,5nm) / Al(150nm)

[0649] Comparative Device Example 14

[0650] The preparation method is the same as that of Example 46, except that the n-type doping layer and electron injection layer materials are replaced with Zn:D-2, and the Zn:D-2 evaporation rate ratio is 10%. The device structure is as follows:

[0651] ITO / HATCN(5nm) / NPB(35nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Zn:D-2(10%,10nm) / HA TCN(10nm) / NPB(75nm) / Be(bq)2:Ir(mphmq)2(tmd)(5%,24nm) / DPPyA(40nm) / Zn:D-2(10%,5nm) / Al(150nm)

[0652] The performance of the organic electroluminescent devices prepared in the above device examples and comparative device examples is shown in Table 2 below.

[0653] Table 2:

[0654] Comparison of Comparative Examples 8 to 10 with Example 54 reveals that, with other materials remaining the same in the tandem organic electroluminescent device structure, the compounds of the present invention exhibit a reduced voltage rise after 24 hours of operation in OLED devices prepared using the prior art compounds in Comparative Examples 8 to 10. Simultaneously, device stability and lifetime are significantly improved. This is presumably due to the fact that during heating and evaporation and device operation, alkali metal ions generated in the alkali metal n-type dopant and cathode interface material may migrate or diffuse into the p-type layer or light-emitting layer, leading to aging of the connecting layer and quenching of excitons in the light-emitting layer, resulting in reduced device efficiency and lifetime.

[0655] The prior art compound D1 used in Comparative Example 11 is 4,7-diphenylphenanthroline (Bphen), a commonly used electron transport material. It has excellent coordination properties and, after being doped with Ag, can serve as a highly efficient electron injection layer and n-type doping layer in the connecting layer. However, this compound has a molecular weight of only 332.41, resulting in a glass transition temperature of only 62°C. This poorly stabilizes the film, leading to the relatively low lifetime of Comparative Example 9.

[0656] The prior art compound D2 used in comparative example 12,13,14 is currently commonly used electron transmission material, by comparing with embodiment 54,99,100 using compound of the present invention E-1, it is seen that because E1 replaces bridging group by phenyl ring with the spirofluorene group with stronger transmission performance, thus is more conducive to electron transmission. Using Ag:E1, Yb:E1, Zn:E1 etc. as the n-type doped layer of series device connecting layer and electron injection layer material, electron generation, transmission, injection performance are significantly better than Ag:D2, Yb:D2, Zn:D2;Compared to D2, the voltage rise value after 24h of device operation using E1 as organic ligand is lower, and life span is also improved. Further comparing embodiment 54 and embodiment 54 to embodiment 61 can find that, when skeleton group is consistent, the electron donating performance of R1 and R2 is stronger, and the coordination performance of corresponding phenanthroline ligand is stronger, and the performance of the electron injection layer prepared accordingly is better, and then significantly reduces the driving voltage of device, improves the efficiency and life span of device. This also reflects that the selection of R1 and R2 in the core structure of the compound of the present invention has an important influence on the performance of this type of phenanthroline material when used in combination with a transition metal as an electron injection layer.

[0657] In summary, the connection layer design strategy of the n-type doping layer / n-type layer / p-type layer proposed in the present invention in the novel tandem OLED device helps to inhibit the diffusion and migration of metal n-type dopants in the tandem OLED device, helps to improve the stability of the connection layer and reduces the exciton quenching in the light-emitting layer. Therefore, it can be applied to the tandem OLED device, which helps the device achieve a longer life and a lower voltage rise during operation.

[0658] The above embodiments are merely examples for clarity of explanation and are not intended to limit the implementation methods. Guided by the concepts of the present invention, those skilled in the art may make various modifications and improvements. Other variations or modifications may also be made based on the above description. Obvious variations or modifications derived therefrom shall remain within the scope of protection of the present invention.

Claims

1. An organic compound having a structure shown in the following formula (1): In formula (1), ring C represents a benzene ring that is absent or fused to ring A and ring B. When ring C is absent, ring A and ring B are connected by a single bond; R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C4-C30 alkylsilyl, unsubstituted or R'-substituted C2-C30 One of alkylamino, unsubstituted or R'-substituted C4-C30 cycloalkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C60 aromatic boron, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R' is selected from the group consisting of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl; n is an integer of 2-8; Q is selected from the substituted or unsubstituted structure shown in the following formula (Q-1) or (Q-2): In formula (Q-1) and (Q-2), X is selected from C, Si or B, and Y is selected from C or N; "—*" represents the attachment site of Q in formula (1), and the number of "—*" is consistent with the selected value of n; The expression of "—" crossing the ring structure indicates that the connection site is at any position on the ring structure that can form a bond; When the above Q has a substituent, the substituent is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that The Q is selected from the substituted or unsubstituted structures shown below: When Q has a substituent, the substituent is selected from deuterium, halogen, cyano, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy one of a C4-C8 alkylsilyl group, a C2-C8 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C6-C60 aromatic boron group, a C6-C60 aryl group, and a C3-C60 heteroaryl group; Preferably, Q is selected from the substituted or unsubstituted structures shown below: When Q has a substituent, the substituent is selected from one of deuterium, halogen, cyano, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

3. The organic compound according to claim 1, characterized in that n is 2, 3 or 4; preferably, n is 2.

4. The organic compound according to claim 1, characterized in that The R1, R2, R3, R4, and R5 are independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C4-C10 cycloalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, dimethylamino, tetrahydropyrrolyl, piperidinyl, cyclohexylimino, cycloheptylimino, cyclooctylimido, methoxy, ethoxy, propoxy , butoxy, phenoxy, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternary, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroisotrimerized indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, tert-butylcarbazolyl, indenocarbazolyl, tetrahydroacridinyl, phenylthioyl, phenol, naphthylthioyl, naphthol, anthracenthioyl, anthracenol, indazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthracenol, benzoxazolyl, naphthoxazolyl, anthracenol, phenanthracenol, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, 1,5-diazepine Anthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, purinyl, pteridinyl, indolizinyl, 1,5,7-triazabicyclo[4.4.0]dec-5-enyl, 4-methoxyphenyl or a combination of two thereof.

5. The organic compound according to claim 1, selected from the following specific structural compounds:

6. Use of the compound according to any one of claims 1 to 5, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the organic compound is used as a doping material and / or an electron injection material in an organic electroluminescent device; More preferably, the organic compound is used as an electron injection material in a single-junction organic electroluminescent device, and as an n-type doping layer material and electron injection material in a connecting layer (n-type doping layer / n-type layer / p-type layer) in a tandem organic electroluminescent device.

7. A single-junction organic electroluminescent device, comprising a substrate and an anode layer, a plurality of light-emitting functional layers and a cathode layer sequentially formed on the substrate, characterized in that: The light-emitting functional layer includes a light-emitting layer and an electron injection layer, and also includes one or more layers of a hole injection layer, a hole transport layer, and an electron transport layer. The hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the light-emitting layer is formed on the hole transport layer, the electron transport layer is formed on the light-emitting layer, the electron injection layer is formed on the electron transport layer, and the cathode layer is formed on the electron injection layer, wherein the electron injection layer includes at least one compound having a structure shown in the following formula (1): In formula (1), ring C represents a benzene ring that is absent or fused to ring A and ring B. When ring C is absent, ring A and ring B are connected by a single bond; R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C4-C30 alkylsilyl, unsubstituted or R'-substituted C2-C30 One of alkylamino, unsubstituted or R'-substituted C4-C30 cycloalkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C60 aromatic boron, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R' is selected from the group consisting of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl; n is an integer of 2-8; Q is selected from the substituted or unsubstituted structure shown in the following formula (Q-1) or (Q-2): In formula (Q-1) and (Q-2), X is selected from C, Si or B, and Y is selected from C or N; "—*" represents the attachment site of Q in formula (1), and the number of "—*" is consistent with the selected value of n; The expression of "—" crossing the ring structure indicates that the connection site is at any position on the ring structure that can form a bond; When the above Q has a substituent, the substituent is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl.

8. The single-junction organic electroluminescent device according to claim 7, characterized in that: The electron injection layer further includes an n-type dopant, which is selected from at least one of alkali metals, alkaline earth metals, transition metals and salts thereof; Preferably, the n-type dopant is selected from one or a mixture of lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, iron, chromium, niobium, cobalt, manganese, nickel, copper, zinc, silver, palladium, rhodium, ruthenium, iridium, tungsten, rhenium, platinum, gold, and ytterbium; The doping ratio of the n-dopant in the electron injection layer to the compound of the structure shown in formula (1) is 0.1 wt % to 50 wt %; preferably, the doping ratio of the n-dopant to the compound of the structure shown in formula (1) is 0.05 wt % to 20 wt %.

9. The single-junction organic electroluminescent device according to claim 7, characterized in that: The thickness of the electron injection layer is 0.1nm-20nm; Preferably, the electron injection layer has a thickness of 3-5 nm.

10. A tandem organic electroluminescent device, comprising the following structure: an anode, a cathode, and at least two electroluminescent units disposed between the anode and the cathode, wherein a connecting layer is disposed between two adjacent electroluminescent units, an electron injection layer is disposed between the light-emitting unit close to the cathode and the cathode, and each of the electroluminescent units comprises at least one electron transport layer and one organic light-emitting layer; Features: The connecting layer is a multi-layer structure, including an n-type doped layer, an n-type layer and a p-type layer; At least one of the n-type doping layer and the electron injection layer comprises at least one compound having a structure represented by the following formula (1); In formula (1), ring C represents a benzene ring that is absent or fused to ring A and ring B. When ring C is absent, ring A and ring B are connected by a single bond; R1, R2, R3, R4, and R5 are independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C4-C30 alkylsilyl, unsubstituted or R'-substituted C2-C30 One of alkylamino, unsubstituted or R'-substituted C4-C30 cycloalkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C60 aromatic boron, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R' is selected from the group consisting of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl; n is an integer of 2-8; Q is selected from the substituted or unsubstituted structure shown in the following formula (Q-1) or (Q-2): In formula (Q-1) and (Q-2), X is selected from C, Si or B, and Y is selected from C or N; "—*" represents the attachment site of Q in formula (1), and the number of "—*" is consistent with the selected value of n; The expression of "—" crossing the ring structure indicates that the connection site is at any position on the ring structure that can form a bond; When Q has a substituent, the substituent is selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C4-C10 alkylsilyl, C2-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aromatic boron, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the n-type doping layer and the electron injection layer both contain at least one compound having a structure represented by formula (1).

11. The tandem organic electroluminescent device according to claim 10, characterized in that: The n-type doping layer in the electron injection layer and the connecting layer further comprises an n-type dopant, and the n-type dopant is selected from at least one of alkali metals, alkaline earth metals, transition metals and salts thereof; Preferably, the n-type dopant is selected from one or a mixture of lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, iron, chromium, niobium, cobalt, manganese, nickel, copper, zinc, silver, palladium, rhodium, ruthenium, iridium, tungsten, rhenium, platinum, gold, and ytterbium; The doping ratio of the n-dopant in the electron injection layer and the n-type doping layer in the connecting layer to the compound of the structure shown in formula (1) is 0.1wt% to 50wt%; preferably, the doping ratio of the n-dopant to the compound of the structure shown in formula (1) is 0.05wt% to 20wt%.

12. The tandem organic electroluminescent device according to claim 10, characterized in that: The thickness of the electron injection layer is 0.1nm-20nm, and the thickness of the n-type doping layer in the connecting layer is 0.1nm-20nm; Preferably, the thickness of the electron injection layer is 3-5 nm, and the thickness of the n-type doping layer in the connecting layer is 1-10 nm.

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