Organic electroluminescent device and display panel

By adopting a double-layer luminescent layer structure in organic electroluminescent devices, using the first host material improved by the pyrene ring and the anthracene compound material with good stability, the problems of low hole transmission efficiency and poor thermal stability of the blue light emitting layer are solved, and the device performance with high efficiency deep blue luminescent and long-life is achieved.

CN120456730APending Publication Date: 2025-08-08GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS LTD
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Patent Information

Application Number
CN202510488390.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-04-17
Publication Date
2025-08-08

AI Technical Summary

Technical Problem

The hole transmission efficiency of the blue light emitting layer of existing organic electroluminescent devices is limited, and the synthesis of blue fluorescent host materials is complex and the thermal stability is poor, resulting in low luminescence efficiency, short life and poor color purity, making it difficult to achieve dark blue luminescence.

Method used

A double-layer luminescent layer structure is adopted, wherein the first sub-luminescent layer material includes a first host material with fluorene, benzoanthracene and ion structures introduced into the pyrene ring, and the second sub-luminescent layer material uses an anthracene-based compound with good stability. The luminescent layer formed by the superposition of the two has a narrow luminescent spectrum and a dark blue fluorescence emission.

Benefits of technology

It improves the luminous efficiency and service life of organic electroluminescent devices, and at the same time realizes high-color purity luminescence in dark blue, improving the overall performance of the device.

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Abstract

The invention relates to an organic light-emitting device and a display panel. The organic light-emitting device comprises a first electrode, a second electrode opposite to the first electrode and a light-emitting layer located between the first electrode and the second electrode. The light-emitting layer comprises a first light-emitting sub-layer and a second light-emitting sub-layer which are stacked; the material of the first light-emitting sub-layer comprises a first host material, the first host material comprises at least one first compound represented by a general formula (1), and the material of the second light-emitting sub-layer comprises a second host material, the second host material comprises at least one second compound represented by a general formula (2): # imgabs0 # imgabs1 #; the light-emitting efficiency and the service life of the organic light-emitting device can be improved, and meanwhile dark blue light emitting is achieved.
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Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to an organic electroluminescent device and a display panel. Background Art

[0002] Organic light-emitting diodes (OLEDs) have great potential for applications in optoelectronic devices such as flat panel displays and lighting due to the diversity of organic semiconductor materials in synthesis, relatively low manufacturing costs, and excellent optical and electrical properties.

[0003] Organic electroluminescence (OLED) refers to the conversion of electrical energy into light energy using organic substances. OLED devices utilizing this phenomenon typically have an anode, a cathode, and an organic layer located between the anode and cathode. To improve the efficiency and lifespan of OLED devices, the organic layer has a multilayer structure, with each layer containing different organic substances. Specifically, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, which then emit light when they transition back to the ground state. Such OLED devices exhibit characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] In order to improve the luminous efficiency of organic light-emitting devices, various fluorescent and phosphorescent luminescent material systems have been developed. Currently, organic light-emitting devices containing blue fluorescent materials have higher reliability, but the development of excellent blue organic light-emitting devices still faces huge challenges. At present, the hole transport efficiency of the blue light-emitting layer of organic light-emitting devices is limited, which affects the improvement of luminous efficiency. In addition, the synthesis of current blue light-emitting fluorescent host materials is relatively complex, which is not conducive to large-scale mass production. Moreover, this type of fluorescent material has poor thermal stability and is easy to decompose, which in turn limits the service life of organic electroluminescent devices. In addition, the emission spectrum of most blue light fluorescent materials is too wide and the color purity is poor, making it difficult to achieve deep blue light emission, which is not conducive to improving the display effect. Therefore, there is an urgent need to develop organic light-emitting devices with good performance. Summary of the Invention

[0005] The present application provides an organic electroluminescent device and a display panel, which can improve the luminous efficiency and service life of the organic electroluminescent device and achieve deep blue light emission.

[0006] In order to achieve the above-mentioned object, according to a first aspect of the present application, an organic electroluminescent device is provided, comprising: a first electrode; a second electrode, disposed opposite to the first electrode; a light-emitting layer located between the first electrode and the second electrode, and comprising a first sub-light-emitting layer and a second sub-light-emitting layer stacked and adjacently arranged; The material of the first sub-light-emitting layer includes a first host material, which includes at least one first compound represented by the general formula (1), and the material of the second sub-light-emitting layer includes a second host material, which includes at least one second compound represented by the general formula (2): ; Among them, R 11 ~R 20 is selected from the group consisting of H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a substituted or unsubstituted silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a cross-linked group, a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy group having 5 to 40 ring atoms, and a heteroaryloxy group having 5 to 40 ring atoms, wherein R 11 ~R 20 In the case where two or more adjacent groups are not cyclic or form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and the R 11 ~R 20 There is at least one structure represented by formula (1-1), formula (1-2) or formula (1-3):

[0007] X is selected from CR 23 , N or C*; * is the substitution site; R 21 ~R 23a combination of one or more selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a substituted or unsubstituted silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinked group, a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy group having 5 to 40 ring atoms, or a heteroaryloxy group having 5 to 40 ring atoms, R 21 ~R 23 In the case of , two or more adjacent groups do not form a ring or form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system; L represents a single bond or a first linking group, wherein the first linking group is selected from one or more combinations of substituted or unsubstituted aromatic rings having 5 to 40 ring atoms, substituted or unsubstituted heteroaromatic ring systems having 5 to 40 ring atoms, aryloxy groups having 5 to 40 ring atoms, and heteroaryloxy groups having 5 to 40 ring atoms, and two or more adjacent groups in the L group are acyclic or form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system; L1 represents a single bond or a second linking group, the second linking group is selected from one or more combinations of substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, substituted or unsubstituted heteroaromatic ring systems having 6 to 40 ring atoms, aryloxy groups having 6 to 40 ring atoms, and heteroaryloxy groups having 6 to 40 ring atoms, and two or more adjacent groups in the L1 group are not cyclic or form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system; The hydrogen atoms in the first compound represented by general formula (1) are not substituted or are substituted by D; R 201 ~R 208 is selected from H, substituted or unsubstituted alkyl having 1 to 50 C atoms, substituted or unsubstituted alkenyl having 2 to 50 C atoms, substituted or unsubstituted alkynyl having 2 to 50 C atoms, -Si(R 301 )(R 302 )(R 303 ) represented by -O-(R 304 ) represented by the group, -S-(R 305 ) represented by the group, -N(R 306 )(R 307 ), a substituted or unsubstituted aralkyl group having 7 to 50 C atoms, -C(=O)R 401The group shown, -COOR 402 One or more of the groups shown, halogen atoms, cyano groups, nitro groups, substituted or unsubstituted aryl groups having 6 to 50 C atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; R 301 ~R 307 、R 401 and R 402 any one or more combinations selected from H, substituted or unsubstituted alkyl groups having 1 to 50 C atoms, substituted or unsubstituted aryl groups having 6 to 50 ring C atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; L 201 and L 202 Any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Ar 201 and Ar 202 Any one or more combinations selected from substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0008] In a second aspect of the present application, a display panel is provided, comprising the organic electroluminescent device.

[0009] In the organic electroluminescent device and display panel provided by the present application, the light-emitting layer of the organic electroluminescent device is composed of an adjacent first sub-light-emitting layer and a second sub-light-emitting layer, the mother core structure of the first host material of the first sub-light-emitting layer is a pyrene ring, and at least one of fluorene, benzanthracene and chrysene structures is introduced into the pyrene ring, so that the first host material has a large molecular weight, strong conjugation and rigidity, which is beneficial to enhancing the solubility of the material, and reducing the singlet energy level S1 of the first host material, so that the overall performance of the organic electroluminescent device is significantly improved; at the same time, the anthracene compound with good stability is used as the second host material of the second sub-light-emitting layer, which can also enhance the solubility of the material, so that the singlet energy level of the second host material is reduced, thereby further improving the overall performance of the organic electroluminescent device. Not only that, the double-layer light-emitting layer formed by superimposing the first sub-light-emitting layer and the second sub-light-emitting layer, the host materials of which cooperate with each other, have a fluorescence emission with a luminescent wavelength at a short wavelength, and the luminescent spectrum is characterized by a narrow half-peak width, so that the light-emitting layer provided by the present application has a deep blue fluorescence emission, which is beneficial to improving the color purity of the organic electroluminescent device. In addition, one of the sub-light-emitting layers in the double-layer light-emitting layer can serve as a transition layer to better transfer holes, thereby improving the luminous efficiency and service life of the organic electroluminescent device. Therefore, the organic electroluminescent device provided in this application, which contains a double-light-emitting layer containing a first host material and a second host material, can deepen the blue light emission while improving the device's luminous efficiency and extending the device's service life. BRIEF DESCRIPTION OF THE DRAWINGS

[0010] To more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present application. Those skilled in the art can also derive other drawings based on these drawings without inventive effort.

[0011] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same drawing numbers represent the same parts in the following description.

[0012] Figure 1 This is a schematic structural diagram of an organic electroluminescent device provided in an embodiment of the present application; Figure 2 This is a schematic structural diagram of a light-emitting layer provided in an embodiment of the present application.

[0013] Explanation of the accompanying drawings: 100, organic electroluminescent device; 10, substrate; 20, first electrode; 30, hole injection layer; 40, hole transport layer; 50, light-emitting layer; 60, electron transport layer; 70, second electrode; 501, first sub-light-emitting layer; 502, second sub-light-emitting layer. DETAILED DESCRIPTION

[0014] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application.

[0015] In this application, composition, printing ink and ink have the same meaning and can be used interchangeably.

[0016] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0017] In the present application, heteroaromatic group, heteroaromatic group and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0018] In the present application, "substituted" means that the hydrogen atom in the substituted group is replaced by a substituent. "Substituted or unsubstituted" means that the defined group may be substituted or not. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to an alkyl group with 1 to 30 carbon atoms, a heterocyclic group with 3 to 20 ring atoms, an aryl group with 5 to 20 ring atoms, a heteroaryl group with 5 to 20 ring atoms, a silanyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, -NRR', a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, a nitro group or a halogen group, and the above groups may also be further substituted by The domain can accept substituents; it is understandable that R and R' in -NRR' are substituted by groups acceptable in the art, including but not limited to H, alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups with 3 to 8 ring atoms, heterocyclic groups with 3 to 8 ring atoms, aryl groups with 5 to 20 ring atoms or heteroaryl groups with 5 to 10 ring atoms, and the above groups can be further substituted by one or more of the following groups: alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups with 3 to 8 ring atoms, heterocyclic groups with 3 to 8 ring atoms, halogen, hydroxyl, nitro or amino.

[0019] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. 1 , then R 1 Can be independently selected from different groups. , 6 R on the benzene ring 1 They may be the same or different from each other. Also, the number of substituents satisfies the substitution rules, for example The o in represents the number of substituents, and o can be selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, The o in can be selected from 0, 1, 2, 3, 4, 5 or 6.

[0020] In this application, the term "ring atoms" refers to the number of atoms that constitute the ring of a compound (e.g., a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When a ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The term "ring atoms" used below applies unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thienyl ring has 5 ring atoms.

[0021] In this application, an aromatic ring system or aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic and polycyclic ring systems. A heteroaromatic ring system or heteroaromatic group refers to a hydrocarbon group (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S, and / or Ge, particularly preferably from Si, N, P, O, and / or S. These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., a fused ring. At least one of these polycyclic rings is aromatic or heteroaromatic. In this application, an aromatic group or heteroaromatic group includes not only aromatic or heteroaromatic systems, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N, or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, and diaryl ether are also considered as aromatic groups in this application.

[0022] Specifically, examples of the aromatic group include benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, naphthracene, fluorene, and derivatives thereof.

[0023] Specifically, examples of heteroaromatic groups include furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, dioxazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone and derivatives thereof.

[0024] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,3-dimethylheptyl, 2-ethylheptyl, 2-butylhept ...butylheptyl, 2-hexyloctyl, 3,3-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2-butylheptyl, 2- ,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0025] In the present application, "*" connected to a single bond indicates a linking site or a fusion site.

[0026] In the present application, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0027] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the adjacent position in the group are fusion sites.

[0028] In the present application, in the energy level structure of organic materials, the triplet energy level ET1, the highest occupied molecular orbital energy level HOMO, and the lowest unoccupied molecular orbital energy level LUMO play a key role. HOMO and LUMO energy levels can be measured by photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereinafter referred to as DFT), have also become effective methods for calculating molecular orbital energy levels. The triplet energy level ET1 of organic materials can be measured by low-temperature time-resolved luminescence spectroscopy, or obtained by quantum simulation calculation (such as by Time-dependent DFT). For example, it is obtained by simulation calculation using commercial software Gaussian 09W (Gaussian Inc.), and specific simulation methods can be found in WO2011141110 or the method described in the examples below.

[0029] It should be noted that the absolute values of HOMO, LUMO, and ET1 depend on the measurement or calculation method used, and even different HOMO / LUMO values can be given for the same method and different evaluation methods. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method. In the description of the embodiments of this application, the values of HOMO, LUMO, and ET1 are obtained based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0030] Currently, the light-emitting layer in organic electroluminescent devices (OLEDs) primarily utilizes a host-guest doped single-layer structure, which has limited hole transfer efficiency and affects luminescence efficiency. The host materials in these light-emitting layers are primarily fused-ring derivatives of anthracene. These compounds have poor thermal stability and are prone to decomposition, resulting in a short device lifespan. Furthermore, these compounds exhibit poor color purity, making it difficult to achieve deep blue emission. Consequently, current OLEDs face challenges in achieving full-color displays, hindering high-end displays.

[0031] In order to solve the above technical problems, the embodiments of the present application provide an organic electroluminescent device and a display panel containing the same. The organic electroluminescent device has a double-layer light-emitting layer structure, and its first sub-light-emitting layer adopts a compound with fluorene, benzanthracene and chrysene structures introduced into the pyrene ring. It is not only simple to synthesize, but also has the advantages of good stability, high solubility and low singlet energy level. When it is superimposed with a second sub-light-emitting layer with an anthracene compound with good stability as the main material, it can not only achieve deep blue light emission, but also improve the hole transfer efficiency, thereby improving the luminous efficiency and service life of the organic electroluminescent device.

[0032] like Figure 1 and Figure 2As shown, an embodiment of the present application provides an organic electroluminescent device 100, comprising a first electrode 20; A second electrode 70, disposed opposite to the first electrode 20; The light-emitting layer 50 is located between the first electrode and the second electrode, and includes a first sub-light-emitting layer 501 and a second sub-light-emitting layer 502 that are stacked and adjacent to each other; The material of the first sub-light-emitting layer includes a first host material, which includes at least one first compound represented by the general formula (1), and the material of the second sub-light-emitting layer includes a second host material, which includes at least one second compound represented by the general formula (2): ; Among them, R 11 ~R 20 a combination of one or more selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a substituted or unsubstituted silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinked group, a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy group having 5 to 40 ring atoms, or a heteroaryloxy group having 5 to 40 ring atoms, R 11 ~R 20 In the case of R, two or more adjacent groups are not cyclic or form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and R 11 ~R 20 There is at least one structure represented by formula (1-1), formula (1-2) or formula (1-3):

[0033] X is selected from CR 23 , N or C*; * is the substitution site; R 21 ~R 23a combination of one or more selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a substituted or unsubstituted silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinked group, a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy group having 5 to 40 ring atoms, or a heteroaryloxy group having 5 to 40 ring atoms, R 21 ~R 23 In the case of , two or more adjacent groups do not form a ring or form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system; L represents a single bond or a first linking group, wherein the first linking group is selected from one or more combinations of substituted or unsubstituted aromatic rings having 5 to 40 ring atoms, substituted or unsubstituted heteroaromatic ring systems having 5 to 40 ring atoms, aryloxy groups having 5 to 40 ring atoms, and heteroaryloxy groups having 5 to 40 ring atoms, and two or more adjacent groups in the L group are acyclic or form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system; L1 represents a single bond or a second linking group, the second linking group is selected from one or more combinations of substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, substituted or unsubstituted heteroaromatic ring systems having 6 to 40 ring atoms, aryloxy groups having 6 to 40 ring atoms, and heteroaryloxy groups having 6 to 40 ring atoms, and two or more adjacent groups in the L1 group are not cyclic or form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system; The hydrogen atoms in the first compound represented by general formula (1) are not substituted or are substituted by D; R 201 ~R 208 is selected from H, substituted or unsubstituted alkyl having 1 to 50 C atoms, substituted or unsubstituted alkenyl having 2 to 50 C atoms, substituted or unsubstituted alkynyl having 2 to 50 C atoms, -Si(R 301 )(R 302 )(R 303 ) represented by -O-(R 304 ) represented by the group, -S-(R 305 ) represented by the group, -N(R 306 )(R 307 ), a substituted or unsubstituted aralkyl group having 7 to 50 C atoms, -C(=O)R 401The group shown, -COOR 402 One or more of the groups shown, halogen atoms, cyano groups, nitro groups, substituted or unsubstituted aryl groups having 6 to 50 C atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; R 301 ~R 307 、R 401 and R 402 any one or more combinations selected from H, substituted or unsubstituted alkyl groups having 1 to 50 C atoms, substituted or unsubstituted aryl groups having 6 to 50 ring C atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; L 201 and L 202 Any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Ar 201 and Ar 202 Any one or more combinations selected from substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0034] It is understood that when different Xs appear, these Xs may be the same or different groups. If two or more Xs are CR 23 , R 23 Can be different or the same.

[0035] It is understandable that if there are two or more R 301 When R 301 Can be the same or different groups; if two or more R 302 When R 302 Can be the same or different groups; if two or more R 303 When R 303 Can be the same or different groups; if two or more R 304 When R 304 Can be the same or different groups; if two or more R 305 When R 305 Can be the same or different groups; if two or more R 306 When R 306 Can be the same or different groups; if two or more R 307 When R 307 Can be the same or different groups; if two or more R 401 When R 401Can be the same or different groups; if two or more R 402 When R 402 The groups may be the same or different.

[0036] In some embodiments, the first host material is selected from at least one compound represented by formula (3-1) to (3-9): .

[0037] Preferably, the L is selected from the group shown in formula (4-1), the L is selected from the group shown in formula (4-1), and the L1 is selected from any one of the structures shown in formulas (4-2) to (4-6):

[0038] Two or more adjacent R 23 is not cyclic or forms a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and when R 23 When not forming a ring, R 23 Select from H or D.

[0039] In one embodiment, two adjacent R 23 Can form a benzene ring.

[0040] In a specific embodiment, the first host material is selected from at least one of the following compounds:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] .

[0066] In the above compounds, Et represents ethyl, iPr represents isopropyl, tBu represents tert-butyl, Ph represents phenyl, and tAm represents tert-amyl.

[0067] It is understood that the organic compounds represented by the general formula (1) provided in the embodiments of the present application are not limited to the ones listed above.

[0068] In some embodiments, the second host material is selected from at least one compound represented by formula (5-1) to (5-9):

[0069]

[0070]

[0071]

[0072] .

[0073] In some embodiments, in the second compound represented by the general formula (2), R 201 ~R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 C atoms, a -Si(R 301 )(R 302 )(R 303 ) shown in the group. Preferably, in the second compound represented by the general formula (2), R 201 ~R 208 are all selected from hydrogen atoms. In some embodiments, the L 201 Select a single bond or a divalent benzene ring, the Ar 201 Any one of the structures shown in formulas (6-1) to (6-3): .

[0074] It can be understood that the two hydrogens in the benzene ring are substituted to form a substitution site, that is, a divalent benzene ring; any hydrogen at any position in the structure shown in formula (6-1) to (6-3) can be substituted to form a site with the L 201 connect.

[0075] In one embodiment, the second host material is selected from at least one of the following compounds: .

[0076] It is understood that the organic compounds represented by the general formula (2) provided in the embodiments of the present application are not limited to the ones listed above.

[0077] In some embodiments, the first organic electroluminescent device has an emission wavelength ranging from 430 nm to 480 nm.

[0078] In some embodiments, the material of the first sub-light-emitting layer further includes a first guest material, and the material of the second sub-light-emitting layer further includes a second guest material. The emission wavelength of the first guest material and / or the second guest material is in the range of 430 nm to 480 nm.

[0079] In this application, the luminescence wavelength is the wavelength range of the main peak of the spectrum.

[0080] In some embodiments, the first guest material and / or the second guest material is selected from at least one compound of formula (5):

[0081] wherein Ar3 is selected from a combination of one or more substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, and substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms; Ar4~Ar7 are selected from any of the following structures:

[0082] V is selected from CR5 or N; W is selected from NR6, CR6R7, SiR6R7, O, S, S=O or SO2; R5 to R7 are selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms.

[0083] It is understood that when V appears at the same time, they can be the same group or different groups. If two or more V are CR5, R5 can be the same group or different groups.

[0084] In some embodiments, the first guest material and / or the second guest material comprises at least one compound represented by Formula (5-1) and / or Formula (5-2): or

[0085] In one embodiment, the first guest material and / or the second guest material comprises at least one of the following compounds:

[0086]

[0087]

[0088] . It is understood that the organic compounds represented by the general formula (5) provided in the embodiments of the present application are not limited to the ones listed above.

[0089] In some other embodiments, the first guest material and / or the second guest material is selected from at least one compound of formula (6): (6) Ar8~Ar 11 One or more selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms and substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms.

[0091] In some embodiments, Ar8 to Ar 11 The group is independently selected from a substituted or unsubstituted aromatic group containing 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 14 ring atoms, or a combination of one or more thereof.

[0092] In some embodiments, the Ar8~Ar 11 Contains any of the following structures:

[0093] V1 is selected from CR8 or N; W1 is selected from NR9, CR9R 10 、SiR9R10 , O, S, S=O or SO2; R8~R 10 a combination of one or more selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms;

[0094] It is understood that when V1 appears at the same time, they can be the same group or different groups. If two or more V1 are CR8, R8 can be the same group or different groups.

[0095] Preferably, R8~R 10 A combination of one or more selected from H, D, an alkyl group having 1 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

[0096] Preferably, R8~R 10 A combination of one or more selected from H, D, an alkyl group having 1 to 10 C atoms, or a phenyl group.

[0097] In some embodiments, in the first light-emitting sub-layer, the mass percentage of the first host material is 95%, and the mass percentage of the first guest material is 5%; and / or, In the second light-emitting sub-layer, the mass percentage of the second host material is 95%, and the mass percentage of the second guest material is 5%.

[0098] In some embodiments, the first electrode 20 is one of a cathode and an anode, and the second electrode 70 is the other of a cathode and an anode.

[0099] In some embodiments, as Figure 2 As shown, the first sub-light emitting layer 501 is directly connected to the second sub-light emitting layer 502 .

[0100] Specifically, the first organic electroluminescent device is an organic light emitting diode (OLED), such as Figure 1As shown, the organic electroluminescent device further includes a substrate 10 , which is connected to a side of the first electrode away from the light-emitting layer 50 .

[0101] In some embodiments, the organic electroluminescent device further includes a hole injection layer 30, a hole transport layer 40, and an electron transport layer 60 disposed between the first electrode 20 and the second electrode 70, the light-emitting layer 50 is disposed between the hole transport layer 40 and the electron transport layer 60, the hole injection layer 30 is disposed between the side of the first electrode 20 away from the substrate 10 and the side of the hole transport layer 40 away from the light-emitting layer 50, and the electron transport layer 60 is disposed between the side of the light-emitting layer 50 away from the hole transport layer 40 and the second electrode 70.

[0102] In some embodiments, the first electrode 20 is an anode, the second electrode 70 is a cathode, the first sub-light-emitting layer 501 is disposed close to the first electrode 20, and the second sub-light-emitting layer 502 is disposed close to the second electrode 70. Of course, in other embodiments, the first sub-light-emitting layer 501 can be disposed close to the second electrode 70, and the second sub-light-emitting layer 502 can be disposed close to the first electrode 20.

[0103] It will be understood that, in the present application, the substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting device, as described, for example, in Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and preferably, the substrate is free of surface defects. In a preferred embodiment, the substrate is flexible and can be selected from a polymer film or plastic, having a glass transition temperature (Tg) of 150°C or higher, preferably greater than 200°C, more preferably greater than 250°C, and most preferably greater than 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene (2,6-naphthalene) (PEN).

[0104] It is understood that, in the present application, the anode may comprise a conductive metal or metal oxide or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or hole transport layer (HTL) or light emitting layer.

[0105] It is understood that in the present application, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be easily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0106] It is understood that, in the present application, the cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light emitting layer.

[0107] It is understood that, in the present application, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting layer, or the n-type semiconductor material serving as the EIL, ETL, or HBL, is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes in OLEDs are possible cathode materials for the devices of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0108] In a preferred embodiment, the organic electroluminescent device provided in the embodiments of the present application is selected from solution-type OLED.

[0109] The organic electroluminescent device provided in the embodiments of the present application can also be applied to electronic devices, including display devices, lighting devices, light sources, sensors, etc.

[0110] An embodiment of the present application further provides an electronic device containing the above-mentioned organic electroluminescent device, wherein the electronic device includes a display device, a lighting device, a light source, a sensor, etc.

[0111] In the organic electroluminescent device provided in the embodiment of the present application, the light-emitting layer of the organic electroluminescent device is composed of an adjacent first sub-light-emitting layer and a second sub-light-emitting layer, the mother core structure of the first host material of the first sub-light-emitting layer is a pyrene ring, and at least one of fluorene, benzanthracene and chrysene structures is introduced into the pyrene ring, so that the first host material has a large molecular weight, strong conjugation and rigidity, which is beneficial to enhancing the solubility of the material, and reducing the singlet energy level S1 of the first host material, so that the overall performance of the organic electroluminescent device is significantly improved; at the same time, using an anthracene compound with good stability as the second host material of the second sub-light-emitting layer can also enhance the solubility of the material, so that the singlet energy level of the second host material decreases, thereby further improving the overall performance of the organic electroluminescent device. Not only that, the double-layer light-emitting layer formed by superimposing the first sub-light-emitting layer and the second sub-light-emitting layer, the host materials of which cooperate with each other, have a fluorescence emission with a luminescent wavelength at a short wavelength, and the luminescent spectrum is characterized by a narrow half-peak width, so that the light-emitting layer provided by the present application has a deep blue fluorescence emission, which is beneficial to improving the color purity of the organic electroluminescent device. In addition, one of the sub-light-emitting layers in the double-layer light-emitting layer can serve as a transition layer to better transfer holes, thereby improving the luminous efficiency and service life of the organic electroluminescent device. Therefore, the organic electroluminescent device provided in this application, which contains a double-light-emitting layer containing a first host material and a second host material, can deepen the blue light emission while improving the device's luminous efficiency and extending the device's service life.

[0112] The embodiment of the present application also provides a first mixture and a second mixture, wherein the first mixture includes at least one compound of the general formula (1) and at least another organic functional material, and the second mixture includes at least one compound of the general formula (2) and at least another organic functional material; the another organic functional material can be selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a light-emitting material (Emitter), a host material (Host) and an organic dye.

[0113] In one embodiment, the another organic functional material is selected from luminescent materials; further, the another organic functional material is selected from blue light luminescent materials.

[0114] The embodiment of the present application also provides a first composition and a second composition, wherein the first composition includes at least one compound of the general formula (1) or the first mixture and a first organic solvent, and the second composition includes at least one compound of the general formula (2) or the second mixture and the first organic solvent; the first organic solvent is selected from one or more combinations of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, boric acid esters or phosphate esters.

[0115] In some embodiments, the first organic solvent is selected from aromatic or heteroaromatic based solvents.

[0116] In some embodiments, the aromatic or heteroaromatic solvent comprises p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, At least one of benzene, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0117] In some embodiments, the aromatic ketone solvent includes at least one of 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone and derivatives thereof, and the derivative includes at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone and 2-methylpropiophenone.

[0118] In some embodiments, the aromatic ether solvent includes at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0119] In some embodiments, at least one of the first organic solvents is selected from aliphatic ketones, including 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, at least one of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.

[0120] In some embodiments, at least one of the first organic solvents is selected from esters, and the lipid solvents include alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0121] In a preferred embodiment, according to the first composition and the second composition of the present application, the first composition comprises at least one compound or polymer or mixture of the general formula (1) and at least one of the first organic solvents, and further comprises a second organic solvent; the first composition comprises at least one compound or polymer or mixture of the general formula (2) and at least one of the first organic solvents, and further comprises a second organic solvent; the second organic solvent comprises at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0122] In some embodiments, solvents particularly suitable for the present application are solvents having Hansen solubility parameters within the following ranges: δd (dispersion force) is between 17.0 and 23.2 MPa 1 / 2 range, especially in the range of 18.5~21.0 MPa 1 / 2 scope; δp (polar force) is 0.2~12.5 MPa 1 / 2 range, especially in the range of 2.0~6.0 MPa 1 / 2 scope; δh (hydrogen bond strength) is between 0.9 and 14.2 MPa 1 / 2 range, especially in the range of 2.0~6.0 MPa 1 / 2 range.

[0123] In the composition of the present application, the organic solvent should be selected based on its boiling point. In this application, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging in inkjet printheads. The organic solvent can be evaporated from the solvent system to form a film containing the functional material.

[0124] In one embodiment, the first composition and the second composition are a solution.

[0125] In another embodiment, the first composition and the second composition are a suspension.

[0126] The first composition in the embodiment of the present application includes 0.01 wt % to 10 wt % of the compound represented by the general formula (1) or the above-mentioned first mixture, and the second composition includes 0.01 wt % to 10 wt % of the compound represented by the general formula (2) or the above-mentioned second mixture.

[0127] In a preferred embodiment, the mass fraction of the compound represented by general formula (1) or the first mixture in the first composition ranges from 0.1 wt% to 15 wt%; in a more preferred embodiment, the mass fraction of the compound represented by general formula (1) or the first mixture in the first composition ranges from 0.2 to 5 wt%; in a most preferred embodiment, the mass fraction of the compound represented by general formula (1) or the first mixture in the first composition ranges from 0.25 wt% to 3 wt%.

[0128] In a preferred embodiment, the mass fraction of the compound represented by general formula (2) or the second mixture in the second composition ranges from 0.1 wt% to 15 wt%; in a more preferred embodiment, the mass fraction of the compound represented by general formula (2) or the second mixture in the second composition ranges from 0.2 to 5 wt%; in a most preferred embodiment, the mass fraction of the compound represented by general formula (2) or the second mixture in the second composition ranges from 0.25 wt% to 3 wt%.

[0129] For example, the content of the compound represented by the general formula (1) or the first mixture in the first composition is 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.12 wt%, 0.2 wt%, 0.25 wt%, 1 wt%, 3 wt%, 5 wt%, 7 wt%, 10 wt%, 12 wt% or 15 wt%; The content of the compound represented by general formula (2) or the second mixture in the second composition is 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.12 wt%, 0.2 wt%, 0.25 wt%, 1 wt%, 3 wt%, 5 wt%, 7 wt%, 10 wt%, 12 wt% or 15 wt%.

[0130] The first composition provided in the embodiments of the present application can be used as a coating or printing ink to prepare organic electronic devices.

[0131] The second composition provided in the embodiments of the present application can be used as a coating or printing ink to prepare organic electronic devices.

[0132] In some embodiments, the coating or the printing ink is used to prepare the organic electronic device by printing or coating.

[0133] Suitable printing or coating techniques include, but are not limited to, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roll printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slot die coating, etc. Gravure printing, spray printing, and inkjet printing are preferred.

[0134] In some embodiments, the solution or the suspension may include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0135] The first composition, the second composition, the first mixture or the second mixture provided in the embodiments of the present application can be applied to the organic electroluminescent device.

[0136] The organic electroluminescent device includes but is not limited to an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (OPED). Particularly preferably, the organic electronic device is an organic electroluminescent device, such as an OLED.

[0137] An embodiment of the present application further provides a display panel, which includes the organic electroluminescent device.

[0138] Specifically, the display panel further includes an array substrate and an encapsulation layer; the organic electroluminescent device is disposed on the array substrate and electrically connected to the array substrate; and the encapsulation layer covers the array substrate and the organic electroluminescent device.

[0139] It can be understood that the array substrate is used to replace the light-emitting device to emit light, and the encapsulation layer is used to protect the organic electroluminescent device.

[0140] Specifically, the display panel further includes an optical film and a cover plate located on a side of the encapsulation layer away from the organic electroluminescent device, wherein the optical film is located between the encapsulation layer and the cover plate. The optical film includes at least one of a polarizer, a light conversion layer, and a color filter.

[0141] In an embodiment of the present application, a display panel includes an organic electroluminescent device having a double-layered light-emitting layer. In the double-layered light-emitting layer, the host material of one layer has a parent core structure of a pyrene ring, and at least one of a fluorene, benzanthracene, and chrysene structure is introduced into the pyrene ring, which helps enhance the solubility of the material and reduces the singlet energy level S1 of the first host material, thereby significantly improving the overall performance of the organic electroluminescent device. The host material of the other layer is a stable anthracene-based compound, which also enhances the solubility of the material and reduces the singlet energy level of the second host material, thereby further improving the overall performance of the organic electroluminescent device. The double-layered light-emitting layer formed by stacking the first and second sub-light-emitting layers has a host material that cooperates with each other to produce a short-wavelength fluorescence emission. The emission spectrum exhibits a narrow half-width at half maximum, resulting in a deep blue fluorescence emission of the light-emitting layer, which helps improve the color purity of the organic electroluminescent device. In addition, one of the sub-light-emitting layers of the double-layered light-emitting layer can serve as a transition layer for better hole transfer, thereby improving the luminous efficiency and service life of the organic electroluminescent device. Therefore, the display panel including the deep blue organic electroluminescent device disclosed in the present application can have an increased color gamut and improved display effects, thereby achieving full-color display.

[0142] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the inventive concept of the present application, those skilled in the art should realize that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific embodiments 1. Synthesis of compounds Example 1 The synthetic route of compound 1 is as follows:

[0144] Synthesis of intermediate 1-3: Intermediates 1-1 (10 mmol) and 1-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The reaction mixture was heated to 100°C and stirred for 6 h under a nitrogen atmosphere. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 1-3 with a molar weight of 8.35 mmol and a yield of 83.5%. The MS (ASAP) value of Intermediate 1-3 was 428.

[0145] Synthesis of intermediate 1-4: Intermediate 1-3 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of THF and DMF (20 / 10 ml). Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 1-4 with a molar weight of 8.73 mmol and a yield of 87.3%. The MS (ASAP) of Intermediate 1-4 was 506.

[0146] Synthesis of compound 1: Intermediates 1-4 (10 mmol) and 1-5 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 1, with a molar weight of 8.37 mmol and a yield of 83.7%. Compound 1 had an MS (ASAP) of 620.

[0147] Example 2 The synthetic route of compound 2 is as follows:

[0148] Synthesis of compound 2: Intermediates 1-4 (10 mmol) and 2-1 (10 mmol) were dissolved in a mixed solvent of 21 ml of 1,4-dioxane and 2 ml of water, and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain compound 2 with a molar weight of 8.39 mmol and a yield of 83.9%. The MS (ASAP) of compound (2) was 670.

[0149] Example 3 The synthetic route of compound 3 is as follows:

[0150] Synthesis of compound 3: Intermediates 1-4 (10 mmol) and 3-1 (10 mmol) were dissolved in a mixed solvent of 21 ml of 1,4-dioxane and 2 ml of water, and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain compound 3 with a molar weight of 8.84 mmol and a yield of 88.4%. The MS (ASAP) of compound (3) was 670.

[0151] Example 4 The synthetic route of compound 4 is as follows:

[0152] Synthesis of compound 4: Intermediates 1-4 (10 mmol) and 4-1 (10 mmol) were dissolved in a mixed solvent of 21 ml of 1,4-dioxane and 2 ml of water, and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain compound 4 with a molar weight of 8.16 mmol and a yield of 81.6%. The MS (ASAP) of compound (4) was 670.

[0153] Example 5 The synthetic route of compound 5 is as follows:

[0154] Synthesis of intermediate 5-3: Intermediates 5-1 (10 mmol) and 5-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 5-3 with a molar weight of 8.79 mmol and a yield of 87.9%. The MS (ASAP) value of Intermediate 5-3 was 312.

[0155] Synthesis of intermediate 5-4: Intermediate 5-3 (10 mmol) and pinacol diboronate (11 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(OA)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 5-4 with a molar weight of 8.17 mmol and a yield of 81.7%. The MS (ASAP) of Intermediate 5-4 was 404.

[0156] Synthesis of intermediate 5-5: Intermediates 5-4 (10 mmol) and 1-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 5-5 with a molar weight of 86.7 mmol and a yield of 86.7%. The MS (ASAP) value of Intermediate 5-5 was 504.

[0157] Synthesis of intermediate 5-6: Intermediate 5-5 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 5-6 with a molar weight of 8.03 mmol and a yield of 80.3%. The MS (ASAP) of Intermediate 5-6 was 582.

[0158] Synthesis of compound 5: Intermediates 5-6 (10 mmol) and 5-7 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 5 with a molar weight of 8.84 mmol and a yield of 88.4%. The MS (ASAP) of compound 5 was 582.

[0159] Example 6 The synthetic route of compound 6 is as follows:

[0160] Synthesis of intermediate 6-2: Intermediates 5-1 (10 mmol) and 6-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 6-2 with a molar weight of 8.38 mmol and a yield of 83.8%. The MS (ASAP) value of Intermediate 6-2 was 312.

[0161] Synthesis of intermediate 6-3: Intermediate 6-2 (10 mmol) and pinacol diboronate (11 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(OA)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 6-3 with a molar weight of 8.72 mmol and a yield of 87.2%. The MS (ASAP) of Intermediate 6-3 was 404.

[0162] Synthesis of intermediate 6-4: Intermediates 6-3 (10 mmol) and 1-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 6-4 with a molar weight of 78.6 mmol and a yield of 7.86%. The MS (ASAP) value of Intermediate 6-4 was 504.

[0163] Synthesis of intermediate 6-5: Intermediate 6-4 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 6-5 with a molar weight of 8.31 mmol and a yield of 83.1%. The MS (ASAP) of Intermediate 6-5 was 582.

[0164] Synthesis of compound 6: Intermediates 6-5 (10 mmol) and 5-7 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 6 with a molar weight of 8.52 mmol and a yield of 85.2%. Compound 6 had an MS (ASAP) of 582.

[0165] Example 7 The synthetic route of compound 7 is as follows:

[0166] Synthesis of intermediate 7-2: Intermediates 5-1 (10 mmol) and 7-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 7-2 with a molar weight of 8.66 mmol and a yield of 86.6%. The MS (ASAP) value of Intermediate 7-2 was 312.

[0167] Synthesis of intermediate 7-3: Intermediate 7-2 (10 mmol) and pinacol diboronate (11 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(OA)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 7-3 with a molar weight of 7.23 mmol and a yield of 72.3%. The MS (ASAP) value of Intermediate 7-3 was 404.

[0168] Synthesis of intermediate 7-4: Intermediates 7-3 (10 mmol) and 1-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 7-4 with a molar weight of 73.3 mmol and a yield of 7.33%. The MS (ASAP) of Intermediate 7-4 was 504.

[0169] Synthesis of intermediate 7-5: Intermediate 7-4 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 7-5 with a molar weight of 8.19 mmol and a yield of 81.9%. The MS (ASAP) of Intermediate 7-5 was 582.

[0170] Synthesis of compound 7: Intermediates 7-5 (10 mmol) and 5-7 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 7 with a molar weight of 8.08 mmol and a yield of 80.8%. The MS (ASAP) of compound 7 was 582.

[0171] Example 8 The synthetic route of compound 8 is as follows:

[0172] Synthesis of intermediate 8-2: Intermediates 1-1 (10 mmol) and 8-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 8-2 with a molar weight of 8.37 mmol and a yield of 83.7%. The MS (ASAP) value of Intermediate 8-2 was 402.

[0173] Synthesis of compound 8: Intermediates 8-2 (10 mmol) and 8-3 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 8 with a molar weight of 8.31 mmol and a yield of 83.1%. Compound 8 had an MS (ASAP) of 594.

[0174] Example 9 The synthetic route of compound 9 is as follows:

[0175] Synthesis of intermediate 9-2: Intermediates 1-1 (10 mmol) and 9-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 9-2 with a molar weight of 7.42 mmol and a yield of 74.2%. The MS (ASAP) value of Intermediate 9-2 was 418.

[0176] Synthesis of compound 9: Intermediates 9-2 (10 mmol) and 8-3 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 9 with a molar weight of 7.09 mmol and a yield of 70.9%. Compound 9 had an MS (ASAP) of 610.

[0177] Example 10 The synthetic route of compound 10 is as follows:

[0178] Synthesis of intermediate 10-2: Intermediates 1-1 (10 mmol) and 10-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 10-2 with a molar weight of 7.28 mmol and a yield of 72.8%. The MS (ASAP) value of Intermediate 10-2 was 477.

[0179] Synthesis of compound 10: Intermediates 10-2 (10 mmol) and 8-3 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 10 with a molar weight of 7.71 mmol and a yield of 77.1%. Compound 10 had an MS (ASAP) of 669.

[0180] Example 11 The synthetic route of compound 11 is as follows:

[0181] Synthesis of intermediate 11-2: Intermediates 1-1 (10 mmol) and 11-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 11-2 with a molar weight of 7.46 mmol and a yield of 74.6%. The MS (ASAP) value of Intermediate 11-2 was 428.

[0182] Synthesis of compound 11: Intermediates 11-2 (10 mmol) and 8-3 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 11, with a molar weight of 7.15 mmol and a yield of 71.5%. The MS (ASAP) of compound 11 was 620.

[0183] Example 12 The synthetic route of compound 12 is as follows:

[0184] Synthesis of compound 12: Intermediates 12-1 (10 mmol) and 12-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 12, with a molar weight of 9.05 mmol and a yield of 90.5%. Compound 12 had an MS (ASAP) of 528.

[0185] Example 13 The synthetic route of compound 13 is as follows:

[0186] Synthesis of compound 13: Intermediates 13-1 (10 mmol) and 12-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 13 with a molar weight of 9.21 mmol and a yield of 92.1%. The MS (ASAP) of compound 13 was 535.

[0187] Example 14 The synthetic route of compound 14 is as follows:

[0188] Synthesis of compound 14: Intermediates 14-1 (10 mmol) and 14-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 14, with a molar weight of 9.12 mmol and a yield of 91.2%. Compound 14 had an MS (ASAP) of 527.

[0189] Example 15 The synthetic route of compound 15 is as follows:

[0190] Synthesis of compound 15: Intermediates 15-1 (10 mmol) and 14-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 15 with a molar weight of 9.24 mmol and a yield of 92.4%. The MS (ASAP) of compound 15 was 475.

[0191] Example 16 The synthetic route of compound 16 is as follows:

[0192] Synthesis of compound 16: Intermediates 16-1 (10 mmol) and 16-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 16 with a molar weight of 9.34 mmol and a yield of 93.4%. Compound 16 had an MS (ASAP) of 430.

[0193] Example 17 The synthetic route of compound 17 is as follows:

[0194] Synthesis of compound 17: Intermediates 17-1 (10 mmol) and 17-2 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 17 with a molar weight of 9.18 mmol and a yield of 91.8%. Compound 17 had an MS (ASAP) of 506.

[0195] Example 18 The synthetic route of compound 18 is as follows:

[0196] Synthesis of compound 18: Intermediates 17-1 (10 mmol) and 18-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 18 with a molar weight of 9.11 mmol and a yield of 91.1%. Compound 18 had an MS (ASAP) of 506.

[0197] Example 19 The synthetic route of compound 19 is as follows:

[0198] Synthesis of compound 19: Intermediates 16-1 (10 mmol) and 18-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 19, with a molar weight of 9.16 mmol and a yield of 91.6%. Compound 19 had an MS (ASAP) of 506.

[0199] Example 20 Synthesis of Compound 20

[0200] Synthesis of intermediate 20-1: Intermediates 1-2 (10 mmol) and 1-5 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 20-1 with a molar weight of 8.71 mmol and a yield of 87.1%. The MS (ASAP) of Intermediate 20-1 was 420.

[0201] Synthesis of intermediate 20-2: Intermediate 20-1 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 20-2 with a molar weight of 8.33 mmol and a yield of 83.3%. The MS (ASAP) of Intermediate 20-2 was 498.

[0202] Synthesis of compound 20: Intermediates 20-2 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 20 with a molar weight of 8.95 mmol and a yield of 89.5%. Compound 20 had an MS (ASAP) of 620.

[0203] Example 21 The synthetic route of compound 21 is as follows:

[0204] Synthesis of intermediate 21-2: Intermediates 21-1 (10 mmol) and 1-5 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 21-2 with a molar weight of 8.32 mmol and a yield of 83.2%. The MS (ASAP) value of Intermediate 21-2 was 431.

[0205] Synthesis of intermediate 21-3: Intermediate 21-2 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 21-3 with a molar weight of 8.57 mmol and a yield of 85.7%. The MS (ASAP) of Intermediate 21-3 was 508.

[0206] Synthesis of compound 21: Intermediates 21-3 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 21 with a molar weight of 8.93 mmol and a yield of 89.3%. The MS (ASAP) of compound 21 was 630.

[0207] Example 22 The synthetic route of compound 22 is as follows:

[0208] Synthesis of intermediate 22-2: Intermediates 21-1 (10 mmol) and 22-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 22-2 with a molar weight of 8.21 mmol and a yield of 82.1%. The MS (ASAP) value of Intermediate 22-2 was 438.

[0209] Synthesis of intermediate 22-3: Intermediate 22-2 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 22-3 with a molar weight of 8.38 mmol and a yield of 83.8%. The MS (ASAP) of Intermediate 22-3 was 515.

[0210] Synthesis of compound 22: Intermediates 22-3 (10 mmol) and 22-4 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 22 with a molar weight of 8.13 mmol and a yield of 81.3%. Compound 22 had an MS (ASAP) of 646.

[0211] Example 23 The synthetic route of compound 23 is as follows:

[0212] Synthesis of intermediate 23-1: Intermediates 21-1 (10 mmol) and 22-4 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 23-1 with a molar weight of 8.67 mmol and a yield of 86.7%. The MS (ASAP) value of Intermediate 23-1 was 448.

[0213] Synthesis of intermediate 23-2: Intermediate 23-1 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 23-2 with a molar weight of 8.11 mmol and a yield of 81.1%. The MS (ASAP) of Intermediate 23-2 was 525.

[0214] Synthesis of compound 23: Intermediates 23-2 (10 mmol) and 22-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 23 with a molar weight of 8.59 mmol and a yield of 85.9%. Compound 23 had an MS (ASAP) of 646.

[0215] Example 24 The synthetic route of compound 24 is as follows:

[0216] Synthesis of intermediate 24-1: Intermediates 21-1 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 24-1 with a molar weight of 8.85 mmol and a yield of 88.5%. The MS (ASAP) value of Intermediate 24-1 was 439.

[0217] Synthesis of intermediate 24-2: Intermediate 24-1 (10 mmol) and NBS (15 mmol) were dissolved in a mixture of 20 ml of THF and 10 ml of DMF. Under a nitrogen atmosphere, the reaction solution was heated to 60°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The organic phase was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford Intermediate 24-2 with a molar weight of 8.08 mmol and a yield of 80.8%. The MS (ASAP) of Intermediate 24-2 was 516.

[0218] Synthesis of compound 24: Intermediates 24-2 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixture of 21 ml of 1,4-dioxane and 2 ml of water. Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100°C and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation. The resulting mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford compound 24 with a molar weight of 8.18 mmol and a yield of 81.8%. The MS (ASAP) of compound 24 was 630.

[0219] 2. Preparation and characterization of OLED devices (1) The energy levels of organic compound materials can be obtained through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian09W (Gaussian Inc.). For detailed simulation methods, see WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule is calculated using the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G (d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated using the following calibration formulas, and S1, T1, and the resonance factor f(S1) are used directly.

[0220] HOMO(eV) = ((HOMO(G)×27.212)-0.9899) / 1.1206 LUMO(eV) = ((LUMO(G)×27.212)-2.0041) / 1.385 HOMO, LUMO, T1, and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1 below: Table 1

[0221] As can be seen from Table 1, compared to BH-ref-1, the S1 energy levels of Compounds 1 to 11 and Compounds 20 to 24 are lowered, and compared to BH-ref-2, the S1 energy levels of Compounds 12 to 19 are lowered. Since the lowered S1 energy level makes it easier for the luminescent material to undergo radiative transitions when returning from the excited state to the ground state, it is beneficial to improve the luminous efficiency of the device. Therefore, the compounds provided in Examples 1 to 24 of the present application are all beneficial to improving the luminous efficiency of the device.

[0222] (2) Preparation of OLED devices The compound structures involved in preparing OLED devices are:

[0223] .

[0224] The following is a detailed description of the preparation process of an OLED device using the above compounds through a specific embodiment. The structure of the OLED device is: ITO / HIL / HTL / EML / EML2 / ETL / cathode. The schematic diagram of the OLED device is shown in FIG. Figure 1 As shown, 10 is a substrate, 20 is an anode, 30 is a hole injection layer (HIL), 40 is a hole transport layer (HTL), 50 is a light emitting layer, 60 is an electron transport layer (ETL), and 70 is a cathode.

[0225] The preparation steps of OLED-1 are as follows: a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrates: Use various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) to clean, and then perform UV ozone treatment; b. HIL (hole injection layer, 40 nm): 60 nm of PEDOT (polyethylenedioxythiophene, Clevios™ AI4083) was spin-coated as the HIL in a clean room and heated on a hot plate at 180°C for 10 minutes. c. HTL (hole transport layer, 20 nm): 20 nm of TFB or PVK (Sigma Aldrich, average Mn 25,000-50,000) was spin-coated in a nitrogen glove box using a 5 mg / ml solution of TFB or PVK in toluene solvent, followed by heating on a hot plate at 180°C for 60 min. d. EML1 (organic light-emitting layer, 15 nm): The EML was formed by spin coating in a nitrogen glove box using a 15 mg / ml solution of methyl benzoate (host / guest weight ratio of 95:5) and then heated on a 140°C hot plate for 10 minutes. The guest structure was BD-1, and the host was compound 1 from Example 1.

[0226] e. EML2 (organic light-emitting layer, 40 nm): The EML was formed by spin coating in a nitrogen glove box using a 15 mg / ml solution of methyl benzoate (host / guest weight ratio of 95:5) with different host and guest structures. The solution was then heated on a hot plate at 140°C for 10 min. The guest structure was BD-1, and the host was compound 15 from Example 15.

[0227] f. Electron transport layer and cathode: The heat-treated substrate was transferred to a vacuum chamber, and then ETL and Liq were placed in different evaporation units under high vacuum (1×10 -6 mbar) were co-deposited at a ratio of 50 wt % to form a 20 nm electron transport layer on the light-emitting layer, and then an Al cathode with a thickness of 100 nm was deposited.

[0228] g. Encapsulation: The device was encapsulated with UV-curable resin in a nitrogen glove box to obtain OLED-1.

[0229] The preparation methods of OLED-2 to OLED-25 and OLED-Ref-1 to OLED-Ref-4 are the same as the preparation method of OLED-1 above, except that the EML1 host material (BH1), EML1 guest material, EML2 host material (BH2), and EML2 guest material are selected as shown in Table 2.

[0230] The current-voltage (JV) characteristics of each OLED device were characterized using a characterization instrument. Important parameters such as efficiency (CE@1knits), lifetime (LT90 @ 1knits), and CIE color coordinates (x, y) were also recorded. The results are shown in Table 2.

[0231] Table 2

[0232] As can be seen from Table 2, the X values of the CIE color coordinates of OLED-1 to OLED-25 are in the range of 0.135 to 0.138, and the Y values are in the range of 0.042 to 0.051. Compared with the CIE color coordinates of comparative examples OLED-Ref-1 to OLED-Ref-4, the X and Y values of the CIE color coordinates of OLED-1 to OLED-25 are smaller. When the X value of the CIE color coordinate is reduced to close to 0.014 and the Y value drops to below 0.1, deep blue light emission can be achieved. Therefore, it can be seen that any organic electroluminescent device of the present application can achieve deep blue light emission.

[0233] Furthermore, as can be seen from Table 2, the luminous efficiency of OLED-1 to OLED-25 is in the range of 8 to 11 cd / A, which is superior. Compared with the luminous efficiency of OLED-Ref-1 to OLED-Ref-4 (4.5 to 6.5 cd / A), the luminous efficiency of OLED-1 to OLED-25 is significantly improved. It can be seen that any organic electroluminescent device of the present application can achieve an improvement in the luminous efficiency of the device.

[0234] Furthermore, Table 2 shows that, when the same guest material is used in the light-emitting layer, the service life of OLED-1 to OLED-25 is improved compared to that of OLED-Ref-1 to OLED-Ref-4.

[0235] Therefore, the light-emitting layer of the organic electroluminescent device of the present application is composed of an adjacent first sub-light-emitting layer and a second sub-light-emitting layer. The mother core structure of the first host material of the first sub-light-emitting layer is a pyrene ring, and at least one of fluorene, benzanthracene and chrysene structures is introduced into the pyrene ring, so that the first host material has a large molecular weight, strong conjugation and rigidity, and the solubility of the material is also enhanced. The singlet energy level S1 of the first host material is reduced, so that the overall performance of the organic electroluminescent device is significantly improved; at the same time, the anthracene compound with good stability is used as the second host material of the second sub-light-emitting layer, which can also enhance the solubility of the material, so that the singlet energy level of the second host material is reduced, thereby further improving the overall performance of the organic electroluminescent device. Not only that, the double-layer light-emitting layer formed by superimposing the first sub-light-emitting layer and the second sub-light-emitting layer, the host materials of which cooperate with each other, have a fluorescence emission with a luminescent wavelength at a short wavelength, and the luminescent spectrum is characterized by a narrow half-peak width. Therefore, the light-emitting layer provided by the present application has a deep blue fluorescence emission, which is beneficial to improving the color purity of the organic electroluminescent device. In addition, one of the sub-light-emitting layers of the double-layer light-emitting layer can serve as a transition layer for better hole transfer, thereby improving the luminous efficiency and service life of the organic electroluminescent device.

[0236] Furthermore, by comparing OLED-1 and OLED-25, it can be seen that when the guest material is BD-1, the lifespan of the organic electroluminescent device is improved.

[0237] In the above embodiments, the description of each embodiment has its own focus. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0238] The above is a detailed introduction to an organic compound, a light-emitting device and a display panel provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the technical solutions and core ideas of the present application. Ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. An organic electroluminescent device, characterized in that: include: a first electrode; a second electrode, disposed opposite to the first electrode; a light-emitting layer located between the first electrode and the second electrode, and comprising a first sub-light-emitting layer and a second sub-light-emitting layer stacked and adjacently arranged; The material of the first sub-light-emitting layer includes a first host material, which includes at least one first compound represented by the general formula (1), and the material of the second sub-light-emitting layer includes a second host material, which includes at least one second compound represented by the general formula (2): ; Among them, R 11 ~R 20 is selected from the group consisting of H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a substituted or unsubstituted silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a cross-linked group, a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy group having 5 to 40 ring atoms, and a heteroaryloxy group having 5 to 40 ring atoms, wherein R 11 ~R 20 In the case where two or more adjacent groups are not cyclic or form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and the R 11 ~R 20 There is at least one structure represented by formula (1-1), formula (1-2) or formula (1-3): X is selected from CR 23 , N or C*; * is the substitution site; R 21 ~R 23 is selected from the group consisting of H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a substituted or unsubstituted silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a cross-linked group, a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, an aryloxy group having 5 to 40 ring atoms, and a heteroaryloxy group having 5 to 40 ring atoms, wherein R 21 ~R 23 In the case of , two or more adjacent groups do not form a ring or form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system; L represents a single bond or a first linking group, wherein the first linking group is selected from one or more combinations of substituted or unsubstituted aromatic groups having 5 to 40 ring atoms, substituted or unsubstituted heteroaromatic ring systems having 5 to 40 ring atoms, aryloxy groups having 5 to 40 ring atoms, and heteroaryloxy groups having 5 to 40 ring atoms, and two or more adjacent groups in the L group are acyclic or form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system; L1 represents a single bond or a second linking group, the second linking group is selected from one or more combinations of substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, substituted or unsubstituted heteroaromatic ring systems having 6 to 40 ring atoms, aryloxy groups having 6 to 40 ring atoms, and heteroaryloxy groups having 6 to 40 ring atoms, and two or more adjacent groups in the L1 group are not cyclic or form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system; The hydrogen atoms in the first compound represented by the general formula (1) are not substituted or are substituted by D; R 201 ~R 208 is selected from H, substituted or unsubstituted alkyl having 1 to 50 C atoms, substituted or unsubstituted alkenyl having 2 to 50 C atoms, substituted or unsubstituted alkynyl having 2 to 50 C atoms, -Si(R 301 )(R 302 )(R 303 ) represented by -O-(R 304 ) represented by the group, -S-(R 305 ) represented by the group, -N(R 306 )(R 307 ), a substituted or unsubstituted aralkyl group having 7 to 50 C atoms, -C(=O)R 401 The group shown, -COOR 402 One or more of the groups shown, halogen atoms, cyano groups, nitro groups, substituted or unsubstituted aryl groups having 6 to 50 C atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; R 301 ~R 307 、R 401 and R 402 any one or more combinations selected from H, substituted or unsubstituted alkyl groups having 1 to 50 C atoms, substituted or unsubstituted aryl groups having 6 to 50 ring C atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; L 201 and L 202 Any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Ar 201 and Ar 202 Any one or more combinations selected from substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms.

2. The organic electroluminescent device according to claim 1, wherein The first host material is selected from at least one compound represented by formula (3-1) to (3-9): 。 3. The organic electroluminescent device according to claim 1 or 2, characterized in that: The L is selected from the group shown in formula (4-1), and the L1 is selected from any one of the structures shown in formulas (4-2) to (4-6): ; Two or more adjacent R 23 is not cyclic or forms a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and when said R 23 When not forming a ring, the R 23 Select from H or D.

4. The organic electroluminescent device according to claim 1, wherein The second host material is selected from at least one compound represented by formula (5-1) to (5-9): 。 5. The organic electroluminescent device according to claim 1 or 4, characterized in that: The L 201 Selected from a single bond or a divalent benzene ring, the Ar 201 Any one of the structures shown in formulas (6-1) to (6-3): 。 6. The organic electroluminescent device according to claim 1, characterized in that The light-emitting wavelength of the organic electroluminescent device is in the range of 430 nm to 480 nm.

7. The organic electroluminescent device according to claim 1, wherein The material of the first light-emitting sub-layer further includes a first guest material, and the material of the second light-emitting sub-layer further includes a second guest material. The light-emitting wavelength of the first guest material and / or the second guest material is in the range of 430 nm to 480 nm.

8. The organic electroluminescent device according to claim 7, characterized in that: The first guest material and / or the second guest material is selected from at least one compound represented by formula (5): wherein Ar3 is selected from a combination of one or more substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, and substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms; Ar4~Ar7 are selected from any of the following structures: V is selected from CR5 or N; W is selected from NR6, CR6R7, SiR6R7, O, S, S=O or SO2; R5 to R7 are selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms.

9. The organic electroluminescent device according to claim 7 or 8, characterized in that: In the first light-emitting sub-layer, the mass percentage of the first host material is 95%, and the mass percentage of the first guest material is 5%; and / or, In the second light-emitting sub-layer, the mass percentage of the second host material is 95%, and the mass percentage of the second guest material is 5%.

10. A display panel, characterized in that: The display panel includes the organic electroluminescent device according to any one of claims 1 to 9.

Citation Information

Patent Citations

  • Photo-stabilizing agents

    WO2011141110A2