Organic compound, light-emitting element and display panel

Abstract

An organic compound, a light-emitting element and a display panel. The organic compound has a structure as represented by general formula (1).

Description

Organic compound, light-emitting element, and display panel Technical Field

[0001] The present application relates to the field of display, and in particular to an organic compound, a light-emitting element and a display panel. Background Art

[0002] Currently, organic electroluminescent devices typically have a positive electrode, a negative electrode, and an organic layer located between them. The organic material in the organic layer converts electrical energy into light energy, thereby achieving organic electroluminescence. When a voltage is applied between the positive and negative electrodes of an organic electroluminescent device, the positive electrode injects holes into the organic layer, while the negative electrode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state, thus achieving the organic electroluminescent device's luminescence. Organic electroluminescent devices offer the advantages of autonomous luminescence, high brightness, high efficiency, low-voltage drive, wide viewing angle, high contrast, and high response. Therefore, organic electroluminescent devices have broad application prospects.

[0003] To improve the luminous efficiency and extend the lifespan of organic electroluminescent devices, suitable hole transport materials are used in the organic functional layers of these devices. This allows electrons and holes to recombine in the center of the light-emitting layer, reducing exciton quenching. However, existing hole transport materials still have deficiencies in carrier transport and other performance, leaving room for improvement in the luminous efficiency and lifespan of organic electroluminescent devices.

[0004] Therefore, an organic compound, a light-emitting element, and a display panel are urgently needed to solve the above technical problems. Technical issues

[0005] The present invention provides an organic compound, a light-emitting element and a display panel, which can alleviate the technical problem of difficulty in improving the luminous efficiency and life of organic electroluminescent elements due to the current deficiencies of hole transport materials in carrier transport and other performances. Technical Solutions

[0006] To solve the above problems, the technical solutions provided by this application are as follows:

[0007] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0008] Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0009] R 1 、R 2 、R 3 、R 4 are independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

[0010] The present invention further provides a light-emitting element, comprising:

[0011] a pair of electrodes, comprising a first electrode and a second electrode;

[0012] an organic functional layer located between the first electrode and the second electrode;

[0013] The material of the organic functional layer includes an organic compound, and the organic compound has a structure as shown in general formula (1):

[0014] Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0015] R 1 、R 2 、R 3 、R 4 are independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

[0016] The present invention further provides a display panel, comprising a light-emitting element, wherein the light-emitting element comprises:

[0017] a pair of electrodes, comprising a first electrode and a second electrode;

[0018] an organic functional layer located between the first electrode and the second electrode;

[0019] The material of the organic functional layer includes an organic compound, and the organic compound has a structure as shown in general formula (1):

[0020] Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0021] R1 、R 2 、R 3 、R 4 are independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] FIG1 is a schematic structural diagram of a light-emitting element provided by an embodiment of the present invention.

[0023] FIG2 is a diagram showing the optimized molecular structure and HOMO energy level distribution of the organic compound M95 provided in an embodiment of the present invention. Modes for Carrying Out the Invention

[0024] The present application provides an organic compound, a light-emitting element, and a display panel. To make the purpose, technical solution, and effects of the present application more clear and explicit, the present application is further described in detail below with reference to the accompanying drawings and examples. It should be understood that the specific examples described herein are only used to explain the present application and are not intended to limit the present application.

[0025] In the present invention, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0026] In the present invention, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0027] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0028] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0029] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, , cyano, isocyano, nitro or halogen, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from but not limited to: a deuterium atom, cyano, isocyano, nitro or halogen, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0030] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0031] In the present invention, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, and can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0032] In the present invention, "heteroaryl or heteroaromatic group" means that at least one carbon atom on the basis of aryl is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidine 1-Hydroxy-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine,

[0033] In the present invention, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl at each occurrence. 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 1-Hexyl, 2 ...

[0034] In the present invention, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am pentyl, Hx hexyl, Cy cyclohexyl.

[0035] In the present invention, "amino group" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0036] In the present invention, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, an amino group refers to -NH2, a formyl group refers to -C(=O)H, a haloformyl group refers to -C(=O)Z (wherein Z represents a halogen), a carbamoyl group refers to -C(=O)NH2, an isocyanate group refers to -NCO, and an isothiocyanate group refers to -NCS.

[0037] In the present invention, the term "alkoxy" refers to a group with the structure "-O-alkyl", i.e., an alkyl group as defined above connected to another group via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0038] In the present invention, "*" connected to a single bond indicates a connection or fusion site.

[0039] In the present invention, 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.

[0040] In the present invention, when the fusion site is not specified in the 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 ortho position in the group are used as the fusion site.

[0041] In the present invention, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0042] In the present invention, the single bond connecting the substituent runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0043] According to the present invention, the cyclic alkyl group or cycloalkyl group has the same meaning and can be interchanged.

[0044] In the present invention, "adjacent groups" means that there is no substitutable site between two substituents.

[0045] In the present invention, "two adjacent R1 or R3 or R5 form a ring with each other" means a ring system formed by two adjacent R1 or R3 or R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0046] At present, due to the deficiencies of hole transport materials in carrier transport and charge balance regulation, there is still room for improvement in the luminous efficiency and lifespan of organic electroluminescent elements.

[0047] An embodiment of the present invention provides an organic compound having a structure as shown in general formula (1):

[0048] Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0049] R 1 、R 2 、R 3 、R 4 are independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

[0050] The present invention uses an organic compound having a structure represented by general formula (1), in which two fluorenyl groups are connected by a single bond to form a highly distorted conformation that is approximately orthogonal, and the two fluorenyl groups are respectively connected to an aromatic amine group to further distort the molecular structure, resulting in a more uniform energy level distribution of the molecule. The organic compound has a stronger hole transport capability and higher stability, and a stronger ability to adjust the transport balance between holes and electrons in a light-emitting element, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0051] In some embodiments, Ar 1 、Ar 2 、Ar 3 、Ar 4 They are independently selected from substituted or unsubstituted aromatic groups having 6 to 16 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms.

[0052] In some embodiments, Ar 1 、Ar 2 、Ar 3 、Ar 4 They are independently selected from substituted or unsubstituted aromatic groups having 6 to 16 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 16 ring atoms.

[0053] In some embodiments, Ar 1 、Ar 2 、Ar 3 、Ar 4are independently selected from the following groups:

[0054] Among them, X 1 、X 2 are independently selected from O, S, N-Ph, CR 6 R 7 ;

[0055] R 5 、R 6 、R 7 are independently selected from hydrogen, deuterium, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 10 ring atoms;

[0056] n is selected from any integer from 0 to 9;

[0057] * indicates the attachment site.

[0058] In some embodiments, X 1 Selected from O, S, N-Ph, CR 6 R 7 , X 2 Selected from O, S, CR 6 R 7 .

[0059] In some embodiments, R 5 、R 6 、R 7 They are independently selected from hydrogen, deuterium, a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 10 ring atoms.

[0060] In some embodiments, R 5 、R 6 、R 7 are independently selected from hydrogen, deuterium, a substituted or unsubstituted straight-chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched-chain alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 6 to 10 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 10 ring atoms.

[0061] In some embodiments, R 5 Each occurrence is independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted branched or cyclic alkyl having 3 to 10 carbon atoms, substituted or unsubstituted phenyl, and substituted or unsubstituted naphthyl.

[0062] In some embodiments, R5 Each occurrence is independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, and substituted or unsubstituted naphthyl.

[0063] In some embodiments, R 5 Each occurrence is independently selected from hydrogen, deuterium, unsubstituted methyl, unsubstituted isopropyl, unsubstituted tert-butyl, unsubstituted cyclohexyl, unsubstituted adamantyl, unsubstituted phenyl, and unsubstituted naphthyl.

[0064] In some embodiments, R 6 、R 7 are independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

[0065] In some embodiments, R 6 、R 7 are independently selected from unsubstituted methyl, unsubstituted ethyl and unsubstituted phenyl.

[0066] In some embodiments, substituted methyl, substituted ethyl, substituted isopropyl, substituted tert-butyl, substituted cyclohexyl, substituted adamantyl satisfy the following conditions:

[0067] At least one hydrogen atom in the group is replaced by a deuterium atom.

[0068] In some embodiments, the substituted phenyl and substituted naphthyl groups satisfy the following conditions:

[0069] At least one hydrogen atom in the group is replaced by a deuterium atom; and / or,

[0070] At least one hydrogen atom in the group is substituted with a methyl group.

[0071] In some embodiments, R 1 、R 2 、R 3 、R 4 When any one of R is selected from substituted methyl, 1 、R 2 、R 3 、R 4 Any one of can be selected from: R 1 、R 2 、R 3 、R 4 When any one of the following is selected from substituted phenyl, R 1 、R 2 、R 3 、R 4Any one of can be selected from:

[0072] In some embodiments, n is selected from any integer from 0 to 9, and n can be selected from any one of 0, 1, 2, 3, 4, 5, 6, 7, 8, and 9.

[0073] In some embodiments, Ar 1 、Ar 2 、Ar 3 、Ar 4 are independently selected from the following groups:

[0074] In some embodiments, Ar 1 with Ar 3 Centrosymmetric, and / or, Ar 2 with Ar 4 Centrosymmetric. When Ar 1 with Ar 3 When the center is symmetrical, Ar 1 with Ar 3 With the same group, when Ar 2 with Ar 4 When the center is symmetrical, Ar 2 with Ar 4 Having the same group is beneficial to simplifying the synthesis of the organic compound.

[0075] In some embodiments, the organic compound has a centrosymmetric structure, or alternatively, the organic compound has a non-centrosymmetric structure. When the organic compound has a centrosymmetric structure, the structure of the organic compound can be completely superimposed after the organic compound molecule is rotated 180 degrees around a point. The centrosymmetric structure of the organic compound facilitates the simplification of its synthesis.

[0076] In some embodiments, the organic compound is selected from the following compounds:

[0077] In the structure of the organic compound provided by the embodiment of the present invention, the two fluorenyl groups are connected by a single bond to form a highly distorted conformation that is approximately orthogonal, and the two fluorenyl groups are respectively connected to an aromatic amine group to further distort the molecular structure, making the energy level distribution of the molecule more uniform. The organic compound has a stronger hole transport ability and higher stability, and a stronger ability to adjust the transport balance of holes and electrons in the light-emitting element, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0078] The present invention also provides a mixture comprising at least one organic compound as described above and an organic functional material, wherein the organic functional material is selected from at least one of hole transport materials, hole injection materials, hole blocking materials, electron injection materials, electron transport materials, host materials or guest materials.

[0079] Referring to FIG. 1 , the present invention further provides a light-emitting element comprising: a pair of electrodes, including a first electrode 101 and a second electrode 102; and an organic functional layer 103 positioned between the first electrode 101 and the second electrode 102. The material of the organic functional layer 103 comprises one or more of the organic compounds described above. The first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0080] In some embodiments, the light-emitting element can be used for organic light-emitting diodes, organic photovoltaic cells, organic light-emitting cells, organic field-effect transistors, organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes, etc., preferably organic light-emitting diodes, organic light-emitting cells and organic light-emitting field-effect transistors.

[0081] In some embodiments, the light-emitting element can be applied to various electronic devices, such as display panels, lighting devices, light sources, etc.

[0082] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer comprising a first compound and a second compound, wherein the first compound is selected from one or more of the organic compounds described above, and the second compound is selected from one or more of a hole injection material, a hole transport material, an electron injection material, an electron transport material, a hole blocking material, a luminescent guest material, a luminescent host material, and an organic dye. Detailed descriptions of the various organic functional materials included in the organic functional layer 103 are provided in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0083] The luminescent guest material is selected from a singlet light emitter (fluorescent light emitter), a triplet light emitter (phosphorescent light emitter) and a TADF material.

[0084] The organic compound may serve as a hole transport material.

[0085] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multi-layered, the organic functional layer 103 includes at least a light-emitting layer 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, a light-emitting auxiliary layer 106, a light-emitting layer 107, an electron injection layer 109, an electron transport layer 108, or a hole blocking layer.

[0086] In some embodiments, the hole transport layer 105 is located between the light-emitting layer 107 and the first electrode 101, the light-emitting auxiliary layer 106 is located between the hole transport layer 105 and the light-emitting layer 107, the hole injection layer 104 is located between the hole transport layer 105 and the first electrode 101, the electron transport layer 108 is located between the light-emitting layer 107 and the second electrode 102, and the electron injection layer 109 is located between the electron transport layer 108 and the second electrode 102.

[0087] In some embodiments, the light-emitting element can be a blue light-emitting element, a green light-emitting element or a red light-emitting element, and the light-emitting layer 107 can include a host material and a guest material, the guest material is one or more of the organic compounds described above, and the host material includes a fused aromatic derivative or a heteroaromatic compound.

[0088] The light-emitting wavelength of the light-emitting element is between 300 and 1000 nm; further, the light-emitting wavelength of the light-emitting element is between 350 and 900 nm; further, the light-emitting wavelength of the light-emitting element is between 400 and 800 nm; further, the light-emitting wavelength of the light-emitting element is within the wavelength range of red light, the wavelength range of green light or the wavelength range of blue light.

[0089] In some embodiments, the host material includes a fused aromatic ring derivative, a heterocyclic compound, or the like, such as at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. The host material can be a host material for a red light-emitting element, a host material for a green light-emitting element, or a host material for a blue light-emitting element. Preferably, the host material is a host material for a blue light-emitting element; when the host material is a host material for a blue light-emitting element, the host material is preferably an anthracene organic compound.

[0090] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc., and preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which helps to inhibit crystallization of the light-emitting layer 107 and suppress concentration quenching caused by high concentrations of the guest material, thereby improving the luminous efficiency of the light-emitting element.

[0091] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer 103, such as injecting holes into the hole injection layer, the hole transport layer, or the light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, hole transport layer, or light-emitting auxiliary layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which 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), etc. In some embodiments, the anode can be patterned, such as patterned ITO conductive substrates are commercially available and can be used to prepare the light-emitting element of the present invention.

[0092] In some embodiments, the cathode is an electron-injecting electrode, and the cathode can inject electrons into the organic functional layer, such as injecting electrons into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the luminescent material in the light-emitting layer, or the n-type semiconductor material serving as the electron injection layer, electron transport layer, or hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes for organic electronic devices may be used as cathode materials for the device of the present invention, including but not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may 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.

[0093] In some embodiments, the hole injection layer 104 is used to promote the injection of holes from the anode into the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material, which is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the functional material of the film layer on the side away from the anode (such as the hole transport material of the hole transport layer). The hole injection material includes but is not limited to at least one of metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0094] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transferred from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material can be selected from the organic compounds described above.

[0095] In some embodiments, the electron transport layer 108 is used to transport electrons. The electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material known in the art with high electron mobility, and may include, but is not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0096] In some embodiments, the electron injection layer 109 is used to inject electrons. The electron injection layer 109 includes an electron injection material. The electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material, and has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer, and also has an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0097] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0098] In some embodiments, the light-emitting element further includes a substrate 110, on which the first electrode 101, the hole injection layer 104, the hole transport layer 105, the light-emitting auxiliary layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked. The substrate 110 can be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent light-emitting element can be fabricated. The substrate 110 can be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 110 can include, but is not limited to, plastic, polymer, metal, semiconductor wafer, or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface is free of surface defects. Preferably, the material of the substrate 110 is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0099] In some embodiments, the light-emitting element may be a solution-type light-emitting element, that is, at least one of the organic functional layers is prepared by printing (eg, inkjet printing).

[0100] In some embodiments, the material of the organic functional layer, the material of the mixture layer, or the material of the light-emitting layer can be prepared from a composition, and the preparation process can be a printing or coating process. The printing or coating process includes inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slit extrusion coating, etc. Preferably, gravure printing, nozzle printing, and inkjet printing are used.

[0101] The composition may be a solution or a suspension, and may include a dispersant and a dispersant, wherein the dispersant is one or more of the organic compounds described above, and the dispersant is used to disperse the dispersant.

[0102] In the composition, the mass fraction of the organic compound described above may be 0.3% to 30%, preferably 0.5% to 20%, more preferably 0.5% to 15%, further preferably 0.5% to 10%, and most preferably 1% to 5%.

[0103] When the composition is used in a printing process, it can be an ink. The viscosity and surface tension of the ink are important parameters, and the appropriate surface tension parameters of the ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the ink at operating temperature or 25°C ranges from 19 dyne / cm to 50 dyne / cm, preferably from 22 dyne / cm to 35 dyne / cm, and more preferably from 25 dyne / cm to 33 dyne / cm, which is advantageous for use in inkjet printing processes. In some embodiments, the viscosity of the ink at operating temperature or 25°C ranges from 1 cps to 100 cps, preferably from 1 cps to 50 cps, more preferably from 1.5 cps to 20 cps, and most preferably from 4.0 cps to 20 cps, which is advantageous for use in inkjet printing processes.

[0104] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The range is preferably 18.5 to 21.0 MPa 1 / 2 range; δp (polar force) is 0.2~12.5MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa 1 / 2 range; δh (hydrogen bond force) is 0.9~14.2MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa 1 / 2 range.

[0105] In some embodiments, the boiling point of the dispersant is greater than or equal to 150°C, preferably greater than or equal to 180°C, more preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, further preferably greater than or equal to 275°C, and most preferably greater than or equal to 300°C. The boiling point of the dispersant is at least greater than or equal to 150°C, which helps prevent nozzle clogging of the inkjet print head during inkjet printing, and a higher boiling point is more effective in preventing clogging.

[0106] The dispersant may include at least one organic solvent, and the organic solvent may be evaporated from the solvent system to form a film containing functional materials. The organic solvent may include at least one first organic solvent, and the first organic solvent may be selected from aromatic or heteroaromatic. Specifically, the first organic solvent may be selected from 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-isopropyl Biphenyl, 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, ethyl 2-furoate, etc.

[0107] The first organic solvent can be selected from aromatic ketone solvents. Specifically, the first organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0108] The first organic solvent can be selected from aromatic ether solvents. Specifically, the first organic solvent can be selected from 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, ethyl-2-naphthyl ether, etc.

[0109] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, for example, 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, 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, tetraethylene glycol dimethyl ether, etc.

[0110] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from 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, isononyl isononanoate, etc. are particularly preferred.

[0111] The organic solvent may further include a second organic solvent, which may be selected from one or more 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, indene and the like.

[0112] In addition to the dispersoid and the dispersant, the composition may further 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.

[0113] Exemplary methods for preparing the organic compounds provided by the present invention are shown in the following exemplary embodiments 1 to 39.

[0114] Synthesis of intermediates I-1 to I-8

[0115] The synthetic route of intermediate I-1 is as follows:

[0116] Synthesis of intermediate I-1:

[0117] A-1 (71.0 g, 0.2 mol) and B-1 (61.5 g, 0.2 mol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (2.3 g, 2.0 mmol), potassium carbonate (55.3 g, 0.4 mol), toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The nitrogen atmosphere was replaced three times, and the temperature was raised to 80°C and refluxed for 12 h. After natural cooling, the separated liquid was washed with water, and the organic phase was dried and then spin-dried. Column chromatography was performed to obtain intermediate I-1 with a yield of 85.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate I-1 was: MS (ASAP) = 455 [M+H] + .

[0118] Synthesis of intermediates I-2 to I-8:

[0119] The intermediates IX were synthesized using the same method as intermediate I-1, except that substrate A-1 was replaced by Aa, and substrate B-1 was replaced by Bb. a, b, and X each represent a positive integer. The molecular structure, mass spectrometry results, and yield of each synthesized intermediate IX are shown in Table 1.

[0120] Table 1 Molecular structure, mass spectrometry results and yields of intermediates I-2 to I-8

[0121] Example 1

[0122] Organic compound M1 Synthesis

[0123] The synthetic route of organic compound M1 is as follows:

[0124] The specific synthesis steps of organic compound M1 are as follows:

[0125] I-1 (10.0 g, 0.02 mol) and M1-1 (8.5 g, 0.05 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.18 g), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (5.8 g, 0.06 mol), and anhydrous toluene (300 mL) were added. The nitrogen atmosphere was replaced three times, and the temperature was raised to 120°C and refluxed for 12 h. After natural cooling, the liquid was washed with water and the organic phase was dried and spin-dried. The organic compound M1 was obtained by column chromatography with a yield of 79.2% and MS (ASAP) = 721 [M+H] + .

[0126] Example 2 to Example 26

[0127] In Examples 2 to 26, the same synthesis method as M1 was used to replace I-1 with different intermediates IX, and MY-1 with M1-1 to obtain organic compounds MY, where Y is a positive integer. The molecular structure, mass spectrometry results, and yield of each organic compound MY are shown in Table 2.

[0128] Table 2 Molecular structure, mass spectrometry results and yield of organic compound MY

[0129] Example 27

[0130] Organic compound N27 Synthesis

[0131] The synthetic route of organic compound N27 is as follows:

[0132] The specific synthesis steps of organic compound N27 are as follows:

[0133] Synthesis of intermediate N27-1:

[0134] I-1 (10.0 g, 0.02 mol) and M42-1 (5.4 g, 0.02 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.18 g), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (4.2 g, 0.04 mol), and anhydrous toluene (300 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 90°C and refluxed for 12 h. After cooling naturally, the liquid was washed with water, and the organic phase was dried and spin-dried. The intermediate N27-1 was obtained by column chromatography in a yield of 56.0% with MS (ASAP) = 664 [M+H] + .

[0135] Synthesis of organic compound N27:

[0136] N27-1 (6.6 g, 0.01 mol) and N27-2 (2.5 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N27 was obtained by column chromatography in a yield of 76.8% with MS (ASAP) = 873 [M+H] + .

[0137] Example 28

[0138] Organic compound N36 Synthesis

[0139] The synthetic route of organic compound N36 is as follows:

[0140] The specific synthesis steps of organic compound N36 are as follows:

[0141] N27-1 (6.6 g, 0.01 mol) and M95-1 (2.2 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N36 was obtained by column chromatography in a yield of 81.0% with MS (ASAP) = 847 [M+H] + .

[0142] Example 29

[0143] Organic compound N45 Synthesis

[0144] The synthetic route of organic compound N45 is as follows:

[0145] The specific synthesis steps of organic compound N45 are as follows:

[0146] Synthesis of intermediate N45-1:

[0147] I-1 (10.0 g, 0.02 mol) and M1-1 (3.7 g, 0.02 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.18 g), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (4.2 g, 0.04 mol), and anhydrous toluene (300 mL) were added. The nitrogen atmosphere was replaced three times, and the temperature was raised to 90°C and refluxed for 12 h. After cooling naturally, the liquid was washed with water, and the organic phase was dried and spin-dried. The intermediate N27-1 was obtained by column chromatography in a yield of 60.2% with MS (ASAP) = 588 [M+H] + .

[0148] Synthesis of organic compound N45:

[0149] N45-1 (6.0 g, 0.01 mol) and N45-2 (2.7 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N45 was obtained by column chromatography in a yield of 79.5% with MS (ASAP) = 821 [M+H] + .

[0150] Example 30

[0151] Organic compound N75 Synthesis

[0152] The synthetic route of organic compound N75 is as follows:

[0153] The specific synthesis steps of organic compound N75 are as follows:

[0154] N45-1 (6.0 g, 0.01 mol) and M131-1 (2.7 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N75 was obtained by column chromatography in a yield of 78.0% with MS (ASAP) = 821 [M+H] + .

[0155] Example 31

[0156] Organic compound N95 Synthesis

[0157] The synthesis route of organic compound N95 is as follows:

[0158] The specific synthesis steps of organic compound N95 are as follows:

[0159] N45-1 (6.0 g, 0.01 mol) and M138-1 (2.9 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the liquid was washed with water and the organic phase was dried and then spin-dried. The organic compound N95 was obtained by column chromatography in a yield of 70.3% with MS (ASAP) = 837 [M+H] + .

[0160] Example 32

[0161] Organic compound N126 Synthesis

[0162] The synthetic route of organic compound N126 is as follows:

[0163] The specific synthesis steps of organic compound N126 are as follows:

[0164] N45-1 (6.0 g, 0.01 mol) and N126-1 (3.6 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N126 was obtained by column chromatography in a yield of 65.2% with MS (ASAP) = 913 [M+H] + .

[0165] Example 33

[0166] Organic compound N173 Synthesis

[0167] The synthetic route of organic compound N173 is as follows:

[0168] The specific synthesis steps of organic compound N173 are as follows:

[0169] Synthesis of intermediate N173-2:

[0170] I-1 (10.0 g, 0.02 mol) and N173-1 (5.4 g, 0.02 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.18 g), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (4.2 g, 0.04 mol), and anhydrous toluene (300 mL) were added. The nitrogen atmosphere was replaced three times, and the temperature was raised to 90°C and refluxed for 12 h. After cooling naturally, the liquid was washed with water, and the organic phase was dried and spin-dried. The intermediate N173-2 was obtained by column chromatography in a yield of 55.5% with MS (ASAP) = 678 [M+H] + .

[0171] Synthesis of organic compound N173:

[0172] N173-2 (6.8 g, 0.01 mol) and N27-2 (2.5 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N173 was obtained by column chromatography in a yield of 68.9% with MS (ASAP) = 887 [M+H] + .

[0173] Example 34

[0174] Organic compound N236 Synthesis

[0175] The synthetic route of organic compound N236 is as follows:

[0176] The specific synthesis steps of organic compound N236 are as follows:

[0177] N45-1 (6.0 g, 0.01 mol) and N236-1 (3.1 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N236 was obtained by column chromatography in a yield of 76.7% with MS (ASAP) = 861 [M+H] + .

[0178] Example 35

[0179] Organic compound N262 Synthesis

[0180] The synthetic route of organic compound N262 is as follows:

[0181] The specific synthesis steps of organic compound N262 are as follows:

[0182] N45-1 (6.0 g, 0.01 mol) and N262-1 (3.3 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N262 was obtained by column chromatography in a yield of 71.3% with MS (ASAP) = 877 [M+H] + .

[0183] Example 36

[0184] Organic compound N294 Synthesis

[0185] The synthetic route of organic compound N294 is as follows:

[0186] The specific synthesis steps of organic compound N294 are as follows:

[0187] I-7 (9.6 g, 0.02 mol) and M42-1 (12.3 g, 0.05 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.18 g), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (5.8 g, 0.06 mol), and anhydrous toluene (300 mL) were added. The nitrogen atmosphere was replaced three times, and the temperature was raised to 120°C and refluxed for 12 h. After cooling naturally, the liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N294 was obtained by column chromatography with a yield of 80.8% and MS (ASAP) = 901 [M+H] + .

[0188] Example 37

[0189] Organic compound N318 Synthesis

[0190] The synthetic route of organic compound N318 is as follows:

[0191] The specific synthesis steps of organic compound N318 are as follows:

[0192] I-8 (11.6 g, 0.02 mol) and M1-1 (8.5 g, 0.05 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.18 g), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (5.8 g, 0.06 mol), and anhydrous toluene (300 mL) were added. The nitrogen atmosphere was replaced three times, and the temperature was raised to 120°C and refluxed for 12 h. After natural cooling, the liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N318 was obtained by column chromatography with a yield of 81.6% and MS (ASAP) = 845 [M+H] + .

[0193] Example 38

[0194] Organic compound N341 Synthesis

[0195] The synthetic route of organic compound N341 is as follows:

[0196] The specific synthesis steps of organic compound N341 are as follows:

[0197] N45-1 (6.0 g, 0.01 mol) and N345-1 (3.1 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N341 was obtained by column chromatography in a yield of 80.8% with MS (ASAP) = 865 [M+H] + .

[0198] Example 39

[0199] Organic compound N345 Synthesis

[0200] The synthetic route of organic compound N345 is as follows:

[0201] The specific synthesis steps of organic compound N345 are as follows:

[0202] N45-1 (6.0 g, 0.01 mol) and N345-1 (4.1 g, 0.01 mol) were weighed and placed in a clean three-necked flask. Pd2(dba)3 (1%, 0.09 g), X-Phos (0.5 g, 1.0 mmol), sodium tert-butoxide (2.0 g, 0.02 mol), and anhydrous toluene (150 mL) were added. The atmosphere was replaced with nitrogen three times, and the temperature was raised to 120°C and refluxed for 8 h. After cooling naturally, the separated liquid was washed with water, and the organic phase was dried and spin-dried. The organic compound N345 was obtained by column chromatography in a yield of 79.8% with MS (ASAP) = 961 [M+H] + .

[0203] Comparative Example

[0204] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 and Comparative Compound 4 were used as comparative examples for Examples 1 to 39 above. Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 and Comparative Compound 4 were respectively denoted as “Ref 1”, “Ref 2”, “Ref 3” and “Ref 4”, and their structural formulas were:

[0205] As shown in Table 3, the HOMO (Highest Occupied Molecular Orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital) energy level, E T1 (first excited triplet state) energy level, E S1 (first excited singlet state) energy level. Specifically, TD-DFT (time-dependent density functional theory) is used through Gaussian09W (Gaussian Inc.). Specifically, the software used to calculate the above energy levels is Gaussian 09W (Gaussian Inc.). The specific simulation method can be found in patent document WO2011141110A2. First, the optimized ground state molecular structure is calculated based on the density functional theory under the B3LYP / 6-31G (d) basis set, and then the E is calculated based on the optimized ground state structure using the time-dependent density functional theory under the B3PW91 / 6-31G (d) basis set. S1 and E T1 , HOMO and LUMO energy levels are calculated according to the following calibration formula, E S1 and E T1Used directly. HOMO (eV) = ((HOMO (G) × 27.212) - 0.9899) / 1.1206 LUMO (eV) = ((LUMO (G) × 27.212) - 2.0041) / 1.385

[0206] Among them, HOMO(G) and LUMO(G) are the direct calculation results of Gaussian09W, and the unit is Hartree.

[0207] Table 3 HOMO energy level, LUMO, E of organic compounds and comparative compounds 1 to 4 S1 Energy levels and E T1 Energy level calculation results

[0208] As can be seen from Table 3, the HOMO energy level of the organic compound provided in the embodiment of the present application is between -5.1eV and -5.3eV, which can meet the energy barrier requirements of different light-emitting elements, and the first excited state energy level is greater than 3.0eV, avoiding interference with the color of visible light emitted by the light-emitting layer of the light-emitting element.

[0209] In addition, please refer to Figure 2. The optimized molecular structure and HOMO energy level distribution of the organic compound M95 provided in the present application are shown in the figure. The molecular orbital distribution of the organic compound provided in the present application is uniform, and the two connected fluorene groups are connected by a single bond to form a nearly orthogonal molecular conformation, providing stable and good hole transport performance, which is conducive to its application as a hole transport material in light-emitting elements.

[0210] The exemplary manufacturing steps of the light-emitting element provided by the present invention are shown in the following exemplary embodiment 40.

[0211] Example 40

[0212] The light-emitting element provided in this embodiment includes an anode layer, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer, which are sequentially formed on a substrate. The specific preparation steps are as follows:

[0213] a. Cleaning of ITO anode: ultrasonic cleaning with deionized water, acetone, and isopropyl alcohol for 15 minutes, followed by treatment in a plasma cleaner for 5 minutes to improve the electrode work function;

[0214] b. Forming hole injection layer: vacuum evaporation method on ITO anode, The hole injection material HATCN is evaporated at a speed of 100 nm to form a hole injection layer with a thickness of 30 nm;

[0215] c. Forming the hole transport layer: vacuum evaporation is used on the hole injection layer. The hole transport material is evaporated at a speed of 100 nm to form a hole transport layer with a thickness of 60 nm;

[0216] d. Forming a light-emitting auxiliary layer: on the hole transport layer The light-emitting auxiliary material Prime is evaporated at a speed of 100 nm to form a light-emitting auxiliary layer with a thickness of 10 nm.

[0217] e. Forming a light-emitting layer: on the light-emitting auxiliary layer The light-emitting layer was formed by evaporation at a speed of 100 nm. BH was used as the host material and BD was used as the doping material. The mass ratio of BH to BD was 98:2, and the thickness of the light-emitting layer was 25 nm.

[0218] f. Forming the electron transport layer: In a vacuum chamber, the electron transport material ET and Liq are placed in different evaporation crucibles and placed in a high vacuum environment (1×10 -6 mbar) to co-deposit ET and Liq in a weight ratio of 5:5 to form an electron transport layer with a thickness of 30 nm;

[0219] g. Forming electron injection layer: An electron injection layer is formed on the electron transport layer by vacuum evaporating the electron injection material Liq at a speed of 1 nm.

[0220] h. Forming cathode layer: Al was deposited on the electron injection layer by vacuum evaporation at a rate of 100 nm to obtain an Al cathode with a thickness of 100 nm;

[0221] i. Packaging: The device is encapsulated with UV-curable resin in a nitrogen glove box.

[0222] Specifically, in this embodiment, the above steps were used to obtain light-emitting elements 1 to 39 and comparative elements 1 to 4. The hole transport materials used in light-emitting elements 1 to 39 were the organic compounds obtained in Examples 1 to 39, respectively, and the hole transport materials used in comparative elements 1 to 4 were Ref 1, Ref 2, Ref 3, and Ref 4, respectively.

[0223] Specifically, HATCN, Prime, BH, BD, ET, Liq, Ref 1, Ref 2, Ref 3, and Ref 4 are all commercially available or synthesized using known synthesis methods and existing raw materials. The chemical structures of Ref 1, Ref 2, Ref 3, and Ref 4 are shown above, and the chemical structures of the other compounds are as follows:

[0224] In this embodiment, the current-voltage (JV) characteristics of light-emitting elements 1 to 39 and comparative elements 1 to 4 were tested, and the JV characteristics of each light-emitting element and the comparative element at a current density of 10 mA / cm 2 The specific results are shown in Table 1: the voltage at the time of the luminance drop, the time required for the luminance to drop to 90% of the initial luminance @1000nits under constant current (relative lifetime), and the relative luminous efficiency.

[0225] Table 4 Performance data of light-emitting elements 1 to 39 and comparative elements 1 to 4

[0226] As can be seen from Table 4, in the light-emitting elements 1 to 39 obtained by using the organic compounds obtained in Examples 1 to 39 as hole transport materials in the hole transport layer, the two fluorenyl groups of the organic compound are connected by a single bond and are respectively connected to an aromatic amine group. The two fluorenyl groups form a highly distorted conformation that is approximately orthogonal, and the energy level distribution is more uniform, the hole transport ability is stronger and the stability is higher. It can also effectively reduce the energy level barrier between the hole injection layer and the light-emitting auxiliary layer, which is beneficial to carrier transport. Compared with comparative elements 1 to 4, the luminous efficiency and life are significantly improved.

[0227] Among them, when the organic compounds obtained in Examples 1 to 39 are used as hole transport materials, compared with Ref 1 and Ref 2 as hole transport materials, the organic compounds obtained in Examples 1 to 39 have a diaromatic amine structure, a larger molecular weight, a higher molecular twist, and a more uniform energy level distribution; when the organic compounds obtained in Examples 1 to 39 are used as hole transport materials, compared with Ref 3 as a hole transport material, due to the presence of nitrogen atoms, the energy levels of the organic compounds obtained in Examples 1 to 39 are more matched and have better hole transport performance; when the organic compounds obtained in Examples 1 to 39 are used as hole transport materials, compared with Ref 4 as a hole transport material, the two aromatic amine groups are each connected to a fluorenyl group, and the energy level distribution is more uniform.

[0228] The light-emitting element disclosed in the embodiment of the present invention uses the organic compound. In the structure of the organic compound, two fluorenyl groups are connected by a single bond to form a highly distorted conformation that is approximately orthogonal, and the two fluorenyl groups are respectively connected to an aromatic amine group to further distort the molecular structure. The energy level distribution of the molecule is more uniform, the hole transport ability of the organic compound is stronger and more stable, and the ability to adjust the transmission balance of holes and electrons in the light-emitting element is stronger, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0229] An embodiment of the present invention further discloses a display panel, which includes any of the above-mentioned light-emitting elements.

[0230] The display panel also includes an array substrate located on one side of the light-emitting element, and an encapsulation layer located on a side of the light-emitting element away from the array substrate and covering the light-emitting element. The display panel also includes a polarizer layer located on a side of the encapsulation layer away from the light-emitting element, and a cover layer located on a side of the polarizer layer away from the light-emitting element. The polarizer layer can be replaced by a color filter layer, which can include multiple color resists and a black matrix located on both sides of the color resists.

[0231] The display panel disclosed in the embodiment of the present invention uses an organic compound having a structure represented by general formula (1) in a light-emitting element. In the structure of the organic compound, two fluorenyl groups are connected by a single bond to form a highly distorted conformation that is approximately orthogonal, and the two fluorenyl groups are respectively connected to an aromatic amine group to further distort the molecular structure. The energy level distribution of the molecule is more uniform, the hole transport ability of the organic compound is stronger and more stable, and the ability to adjust the transmission balance of holes and electrons in the light-emitting element is stronger, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0232] The embodiments of the present invention disclose an organic compound, a light-emitting element, and a display panel. The organic compound has a structure as shown in general formula (1): The present invention uses an organic compound having a structure represented by general formula (1). In the structure of the organic compound, two fluorenyl groups are connected by a single bond to form a highly distorted conformation that is approximately orthogonal, and the two fluorenyl groups are respectively connected to an aromatic amine group to further distort the molecular structure. The energy level distribution of the molecule is more uniform, the hole transport ability of the organic compound is stronger and more stable, and the ability to adjust the transport balance of holes and electrons in the light-emitting element is stronger, thereby improving the luminous efficiency of the light-emitting element and extending the service life of the light-emitting element.

[0233] It is understandable that those skilled in the art can make equivalent substitutions or changes based on the technical solution and inventive concept of this application, and all these changes or substitutions should fall within the scope of protection of the claims attached to this application.

Claims

1. An organic compound, wherein, The organic compound has a structure represented by the general formula (1): Among them, Ar 1 , Ar 2 , Ar 3 , Ar 4 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms; R 1 、R 2 、R 3 、R 4 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

2. The organic compound according to claim 1, wherein, Ar 1 、Ar 2 、Ar 3 、Ar 4 are each independently selected from the following groups: wherein, X 1 and X 2 are each independently selected from O, S, N-Ph, CR 6 R 7 ; R 5 、R 6 、R 7 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkyl group or cyclic alkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms; n is any integer selected from 0 to 9; * represents a linking site.

3. The organic compound according to claim 2, wherein X 1 Selected from O, S, N-Ph, CR 6 R 7 , X 2 Selected from O, S, CR 6 R 7 ; R 5 Each occurrence is independently selected from hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted naphthyl group; R 6 and R 7 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

4. The organic compound according to claim 3, wherein, R 5 Each occurrence is independently selected from hydrogen, deuterium, unsubstituted methyl, unsubstituted isopropyl, unsubstituted tert-butyl, unsubstituted cyclohexyl, unsubstituted adamantyl, unsubstituted phenyl, and unsubstituted naphthyl; R 6 、R 7 are each independently selected from unsubstituted methyl, unsubstituted ethyl, and unsubstituted phenyl.

5. The organic compound according to claim 3, wherein, Ar 1 、Ar 2 、Ar 3 、Ar 4 are each independently selected from the following groups:

6. The organic compound according to claim 1, wherein, Ar 1 is centrosymmetric with Ar 3 .

7. The organic compound according to claim 1, wherein, Ar 2 is centrosymmetric with Ar 4 .

8. The organic compound according to claim 1, wherein, The substituted methyl, substituted ethyl, and substituted phenyl satisfy the following conditions: At least one hydrogen atom in the group is replaced by a deuterium atom.

9. The organic compound according to claim 1, wherein, R 1 、R 2 、R 3 、R 4 are each independently selected from unsubstituted methyl, unsubstituted ethyl, unsubstituted phenyl, 10. The organic compound according to claim 1, wherein, The organic compound is selected from the following compounds:

11. A light-emitting element, wherein, Comprising: A pair of electrodes, including a first electrode and a second electrode; An organic functional layer located between the first electrode and the second electrode; Among them, the material of the organic functional layer includes an organic compound, and the organic compound has a structure shown in the general formula (1): Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms; R 1 、R 2 、R 3 、R 4 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

12. The light-emitting element according to claim 11, wherein, The organic functional layer includes a light-emitting layer, a hole-transporting layer located between the light-emitting layer and the first electrode, a light-emission assisting layer located between the hole-transporting layer and the light-emitting layer, a hole-injecting layer located between the hole-transporting layer and the first electrode, an electron-transporting layer located between the light-emitting layer and the second electrode, and an electron-injecting layer located between the electron-transporting layer and the second electrode; Wherein, the hole-transporting layer includes the organic compound.

13. The light-emitting element according to claim 11, wherein, Ar 1 、Ar 2 、Ar 3 、Ar 4 are each independently selected from the following groups: Among them, X 1 and X 2 are each independently selected from O, S, N-Ph, CR 6 R 7 ; R 5 、R 6 、R 7 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkyl group or cyclic alkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms; n is any integer selected from 0 to 9; * represents a linking site.

14. The light-emitting element according to claim 13, wherein, X 1 Selected from O, S, N-Ph, CR 6 R 7 , X 2 Selected from O, S, CR 6 R 7 ; R 5 Each occurrence is independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted branched or cyclic alkyl having 3 to 10 carbon atoms, substituted or unsubstituted phenyl, and substituted or unsubstituted naphthyl; R 6 、R 7 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

15. The light-emitting element according to claim 14, wherein, R 5 Each occurrence is independently selected from hydrogen, deuterium, unsubstituted methyl, unsubstituted isopropyl, unsubstituted tert-butyl, unsubstituted cyclohexyl, unsubstituted adamantyl, unsubstituted phenyl, and unsubstituted naphthyl; R 6 、R 7 are each independently selected from unsubstituted methyl, unsubstituted ethyl, and unsubstituted phenyl.

16. A display panel, wherein, Comprising a light-emitting element, the light-emitting element includes: A pair of electrodes, including a first electrode and a second electrode; An organic functional layer located between the first electrode and the second electrode; Among them, the material of the organic functional layer includes an organic compound, and the organic compound has a structure shown in the general formula (1): Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms and substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms; R 1 、R 2 、R 3 、R 4 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

17. The display panel according to claim 16, wherein, The organic functional layer includes a light-emitting layer, a hole-transporting layer located between the light-emitting layer and the first electrode, a light-emission assisting layer located between the hole-transporting layer and the light-emitting layer, a hole-injecting layer located between the hole-transporting layer and the first electrode, an electron-transporting layer located between the light-emitting layer and the second electrode, and an electron-injecting layer located between the electron-transporting layer and the second electrode; Wherein, the hole-transporting layer includes the organic compound.

18. The display panel according to claim 16, wherein, Ar 1 、Ar 2 、Ar 3 、Ar 4 are each independently selected from the following groups: Among them, X 1 and X 2 are each independently selected from O, S, N-Ph, CR 6 R 7 ; R 5 、R 6 、R 7 are each independently selected from hydrogen, deuterium, substituted or unsubstituted groups having 1 to 20 carbon atoms A straight-chain alkyl group of the formula, a substituted or unsubstituted branched alkyl group or cyclic alkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms; n is any integer selected from 0 to 9; * represents a linking site.

19. The display panel according to claim 18, wherein, X 1 Selected from O, S, N-Ph, CR 6 R 7 , X 2 Selected from O, S, CR 6 R 7 ; R 5 Each occurrence is independently selected from hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted naphthyl group; R 6 、R 7 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, and substituted or unsubstituted phenyl.

20. The display panel according to claim 19, wherein, R 5 each occurrence is independently selected from hydrogen, deuterium, unsubstituted methyl, unsubstituted isopropyl, unsubstituted tert-butyl, unsubstituted cyclohexyl, unsubstituted adamantyl, unsubstituted phenyl, and unsubstituted naphthyl; R 6 and R 7 are each independently selected from unsubstituted methyl, unsubstituted ethyl, and unsubstituted phenyl.

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