Organic compound, light-emitting element and display panel

Abstract

An embodiment of the present invention discloses an organic compound, a light-emitting element and a display panel. The organic compound has a structure as shown in general formula (1): General formula (1). The present invention uses an organic compound containing an amine group, in which the organic compound has both a heterocycle and an amine group, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, increasing the luminous efficiency of the light-emitting element and extending the luminous life of the light-emitting element.

Description

Technical Field

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

[0002] At present, organic electroluminescent elements usually have a positive electrode, a negative electrode and an organic layer between the two, and use the organic material of the organic layer to convert electrical energy into light energy, thereby realizing organic electroluminescence. In order to improve the luminous efficiency and service life of organic electroluminescent elements, the organic layer is often multi-layered, and the organic material of each layer is different. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. A voltage is applied between the positive and negative electrodes of the organic electroluminescent element, the positive electrode injects holes into the organic layer, and the negative electrode injects electrons into the organic layer. The injected holes meet with the electrons to form excitons, and the excitons emit light when they transition back to the ground state, thereby realizing the luminescence of the organic electroluminescent element. Organic electroluminescent devices have the characteristics 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] Accordingly, the development of materials for organic light emitting diodes (OLED) has also attracted widespread attention due to its diversity in synthesis, simple composition and process, and other advantages. At the same time, in order to improve the luminous efficiency of organic electroluminescent elements, people have tried various material systems with energy transmission and conversion mechanisms, but the luminous efficiency, stability, and lifespan of the luminescent materials used in OLED elements (especially the luminescent materials of blue OLED elements) are still relatively low, resulting in limited performance improvements in OLED elements.

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

[0005] The present invention provides a method for alleviating the technical problem that the luminous efficiency, stability, lifespan and other performances of the luminescent materials currently used in OLED elements are relatively low, resulting in the difficulty in improving the performance of OLED elements.

[0006] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0007]

[0008] wherein Z is selected from CR1R2, NR3, O or S;

[0009] X and Y are independently selected from O or NR4;

[0010] R1-R4 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0011] R1, R2 are connected to form a ring or are independent of each other;

[0012] Ar1 is selected from H, D, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0013] Ar2-Ar3 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0014] Ar4 to Ar5 each independently represents a substituted or unsubstituted aromatic group of 6 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic group of 5 to 30 carbon atoms.

[0015] Preferably, the organic compound has a structure as shown in general formula (2) to general formula (7):

[0016] The organic compound has a structure as shown in general formula (2) to general formula (7):

[0017]

[0018]

[0019] Preferably, the organic compound has a structure as shown in general formula (8) to general formula (13):

[0020]

[0021] Preferably, the organic compound has a structure as shown in general formula (14):

[0022]

[0023] Wherein, Ar6 and Ar7 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms.

[0024] Preferably, the organic compound has a structure as shown in general formula (15):

[0025]

[0026] Wherein, Ar8 and Ar9 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms.

[0027] Preferably, Z is selected from CR1R2, O or S;

[0028] X and Y are independently selected from O or NR4, and X and Y are not O at the same time;

[0029] R1-R4 are independently selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms.

[0030] Preferably, R4 is selected from methyl, substituted or unsubstituted phenyl, naphthyl, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl.

[0031] Preferably, Ar1 is selected from H, D, methyl, isopropyl, tert-butyl, tert-amyl, substituted or unsubstituted phenyl, naphthyl, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl or amine.

[0032] Preferably, Ar2 and Ar3 are independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl or methyl;

[0033] Ar4 and Ar5 are each independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, and carbazolyl.

[0034] Preferably, the organic compound is selected from the following compounds:

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051] The present invention also provides a light-emitting element, comprising:

[0052] a pair of electrodes, including a first electrode and a second electrode;

[0053] an organic functional layer located between the first electrode and the second electrode;

[0054] Wherein, the material of the organic functional layer includes one or more of the organic compounds as described in any one of the above items.

[0055] Preferably, the organic functional layer at least includes a light-emitting layer, and the light-emitting layer includes a host material and a guest material, and the guest material is one or more of the organic compounds described in any one of the above items.

[0056] Preferably, in the light-emitting layer, the mass ratio of the host material to the guest material is 99:1 to 70:30.

[0057] The present invention further provides a display panel, comprising the light-emitting element as described in any one of the above items.

[0058] The present invention uses an amine-containing organic compound, in which both a heterocycle and an amine group are present, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, increasing the luminous efficiency of the light-emitting element and extending the luminous life of the light-emitting element. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without paying any creative work.

[0060] Figure 1 It is a structural schematic diagram of a light-emitting element provided in an embodiment of the present invention. DETAILED DESCRIPTION

[0061] The following will be combined with the drawings in the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments in the present invention, all other embodiments obtained by those skilled in the art without creative work belong to the scope of protection of the present invention. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present invention, and are not used to limit the present invention. In the present invention, unless otherwise specified, the directional words used, such as "upper" and "lower", generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the drawings; while "inside" and "outside" refer to the outline of the device. In the present invention, "optionally", "optional", and "optional" refer to optional, that is, to select any one of the two parallel solutions of "yes" or "no". If multiple "optional" appear in a technical solution, if there is no special explanation and there is no contradiction or mutual restriction, each "optional" is independent. In the present invention, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0062] In the present invention, aromatic groups, aromatics, and aromatic ring systems have the same meaning and can be interchanged. "Aryl or aromatic group or aromatic ring system" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which 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 aromatic groups having 6 to 40 ring atoms" refers to aromatic groups containing 6 to 40 ring atoms, preferably substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, more preferably substituted or unsubstituted aromatic groups having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted aromatic groups having 6 to 14 ring atoms, and the aromatic groups are optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understandable 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.

[0063] In the present invention, heteroaromatic groups, heteroaromatics, and heteroaromatic ring systems have the same meaning and can be interchanged. "Heteroaromatic group or heteroaromatic group or heteroaromatic ring system" means that at least one carbon atom on the basis of aromatic group is replaced by non-carbon atom, and non-carbon atom can be N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and heteroaryl is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0064] In the present invention, "substituted" means that one or more hydrogen atoms in the substituted group are replaced by a substituent. When the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs, R can be independently selected from different groups. In the embodiments of the present invention, "substituted or unsubstituted" means that the defined group can be substituted or not substituted; when the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, and the substituents R are selected from but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogens, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and the above groups can also be further substituted by substituents acceptable in the art; wherein, R in -NR'R" R' and R" are independently selected from but not limited to: H, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1 to 10 C atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, and a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from but not limited to: a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen, an alkyl group containing 1 to 10 C 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 also be further substituted by substituents acceptable in the art.

[0065] In the present invention, "amino group" refers to an amine derivative having a structural feature of the formula -NR'R", wherein R' and R" have the same meanings as described above.

[0066] In the present invention, the "number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms bonding to form a ring; when the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same applies to the "number of ring atoms" described below 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.

[0067] In the present invention, "*" connected to a single bond indicates a connection or fusion site; when the connection site is not specified in the group, it means that any optional connection site in the group can be used as the connection site; when the same group contains multiple substituents with the same symbol, the substituents can be the same or different from each other, for example The six Rs on the benzene ring may be the same or different from each other; the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0068] At present, due to the low performance of luminous efficiency, stability and life of the luminescent materials used in OLED elements, there is a problem that the performance of OLED elements is difficult to improve.

[0069] An embodiment of the present invention provides an organic compound having a structure as shown in general formula (1):

[0070]

[0071] wherein Z is selected from CR1R2, NR3, O or S;

[0072] X and Y are independently selected from O or NR4;

[0073] R1-R4 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0074] R1, R2 are connected to form a ring or are independent of each other;

[0075] Ar1 is selected from H, D, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0076] Ar2-Ar3 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0077] Ar4 to Ar5 each independently represents a substituted or unsubstituted aromatic group of 6 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic group of 5 to 30 carbon atoms.

[0078] The present invention uses an amine-containing organic compound, in which both a heterocycle and an amine group are present, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, increasing the luminous efficiency of the light-emitting element and extending the luminous life of the light-emitting element.

[0079] In some embodiments, the organic compound has a structure as shown in general formula (2) to general formula (7):

[0080]

[0081] In some embodiments, the organic compound has a structure as shown in general formula (8) to general formula (13):

[0082]

[0083] In some embodiments, the organic compound has a structure as shown in formula (14):

[0084]

[0085] Wherein, Ar6 and Ar7 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms.

[0086] In some embodiments, the organic compound has a structure as shown in formula (15):

[0087]

[0088] Wherein, Ar8 and Ar9 are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms.

[0089] In the above embodiments, Z is selected from CR1R2, O or S;

[0090] X and Y are independently selected from O or NR4, and X and Y are not O at the same time;

[0091] R1-R4 are independently selected from substituted or unsubstituted alkyl groups with 1-12 carbon atoms, substituted or unsubstituted aromatic groups with 6-20 carbon atoms, substituted or unsubstituted heteroaromatic groups with 5-20 carbon atoms. Preferably, R1-R4 are independently selected from substituted or unsubstituted alkyl groups with 1-8 carbon atoms, substituted or unsubstituted aromatic groups with 6-15 carbon atoms, substituted or unsubstituted heteroaromatic groups with 5-15 carbon atoms. More preferably, R1 and R2 are independently selected from methyl, substituted or unsubstituted phenyl; R4 is selected from methyl, substituted or unsubstituted phenyl, naphthyl, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl.

[0092] In the above embodiments, Ar1 is selected from H, D, substituted or unsubstituted alkyl groups with 1-12 carbon atoms, substituted or unsubstituted aromatic groups with 6-20 carbon atoms, substituted or unsubstituted heteroaromatic groups with 5-20 carbon atoms. Preferably, Ar1 is selected from H, D, substituted or unsubstituted alkyl groups with 1-8 carbon atoms, substituted or unsubstituted aromatic groups with 6-15 carbon atoms, substituted or unsubstituted heteroaromatic groups with 5-15 carbon atoms. More preferably, Ar1 is selected from H, D, methyl, isopropyl, tert-butyl, tert-amyl, substituted or unsubstituted phenyl, naphthyl, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl or amine.

[0093] In the above embodiment, Ar2 and Ar3 are independently selected from substituted or unsubstituted alkyl groups with 1 to 12 carbon atoms, substituted or unsubstituted aromatic groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 20 carbon atoms. Preferably, Ar2 and Ar3 are independently selected from substituted or unsubstituted alkyl groups with 1 to 8 carbon atoms, substituted or unsubstituted aromatic groups with 6 to 15 carbon atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 15 carbon atoms. More preferably, Ar2 and Ar3 are independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl or methyl.

[0094] Ar4 and Ar5 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 20 carbon atoms. Preferably, Ar4 and Ar5 are independently selected from substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 15 carbon atoms. More preferably, Ar4 and Ar5 are independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuran, dibenzothiophene, fluorenyl, carbazolyl.

[0095] In some embodiments, the organic compound is selected from the following compounds:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111] The organic compound provided in the embodiment of the present invention forms a larger conjugated system and a larger rigid plane by connecting aromatic rings and heteroaromatic rings through heterocyclic rings, effectively suppresses the vibration relaxation caused by the vibration and rotation of the organic compound molecules, improves its luminous efficiency and thermal stability, and further enhances the conjugation and resonance effects of the organic compound by the introduction of amine groups, improves the performance of the organic compound, improves the luminous efficiency of the light-emitting element using the organic compound, and prolongs the luminous life of the light-emitting element.

[0112] The present invention also provides a light-emitting element, the light-emitting element comprising: a pair of electrodes, including a first electrode 101 and a second electrode 102; an organic functional layer 103 located between the first electrode 101 and the second electrode 102; wherein 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.

[0113] In some embodiments, the light-emitting element can be used in organic light-emitting diodes, organic photovoltaic cells, organic light-emitting cells, organic field effect transistors, organic light-emitting field effect transistors, organic lasers, organic spin electronic devices, organic sensors and organic plasmon emission diodes, etc., preferably organic light-emitting diodes, organic light-emitting cells, and organic light-emitting field effect transistors.

[0114] In some embodiments, the light emitting element can be applied to a variety of electronic devices, such as display panels, lighting devices, light sources, etc.

[0115] In some embodiments, the organic functional layer 103 can be a single layer. In this case, the organic functional layer 103 is a mixture layer, and the mixture layer includes a first compound and a second compound. 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 hole injection materials, hole transport materials, electron transport materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes.

[0116] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0117] When the second compound is a light-emitting guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0118] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multiple layers, the organic functional layer 103 at least includes 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 layer 107, an electron blocking layer 106, an electron injection layer 109, an electron transport layer 108 or a hole blocking layer.

[0119] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer 103, such as: the anode injects 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, the hole transport layer or the electron blocking 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 ordinary technicians in the field. The material of the anode 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 devices according to the present invention.

[0120] In some embodiments, the cathode is an electrode for injecting electrons, and the cathode can inject electrons into the organic functional layer, such as: the cathode injects electrons into the electron injection layer, the electron transport layer, or the 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 as the electron injection layer, the electron transport layer or the 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 of organic electronic devices may be used as cathode materials of the device of the present invention, and the materials of the cathode include but are 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.

[0121] In some embodiments, the hole injection layer 104 is used to promote the injection of holes from the anode to 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 (such as the hole transport material of the hole transport layer) into which the holes are injected away from the anode. The hole injection material includes but is not limited to at least one of metal porphyrin, oligothiophene, organic material based on arylamine, organic material based on hexanitrile hexaazatriphenylene, organic material based on quinacridone, organic material based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0122] 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, which receives holes transmitted from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and the hole transport material may include but is not limited to at least one of an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, and the like.

[0123] In some embodiments, the electron transport layer 108 is used to transport electrons, and the electron transport layer 108 includes an electron transport material, which receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material with high electron mobility known in the art, and the electron transport material 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.

[0124] In some embodiments, the electron injection layer 109 is used to inject electrons, and the electron injection layer 109 includes an electron injection material, and 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 the excitons generated by the light-emitting layer 107 from moving 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, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc.

[0125] 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 diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like.

[0126] Preferably, the light-emitting layer 107 includes a host material and a guest material, and the guest material is one or more of the organic compounds described above.

[0127] Preferably, 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. 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 is beneficial to inhibiting the crystallization of the light-emitting layer 107 and inhibiting concentration quenching caused by high concentration of the guest material, thereby improving the luminous efficiency of the light-emitting element.

[0128] Preferably, the host material may be an anthracene-based, boron-oxygen-based or exciplex-based host material.

[0129] The light emitting element may have a light emission wavelength between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 and 800 nm. The light emitted by the light emitting element may be red light, green light or blue light, preferably blue light.

[0130] In some embodiments, the light-emitting element further comprises a substrate, and the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking 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 on the substrate. The substrate may be a transparent substrate or an opaque substrate. When the substrate is a transparent substrate, a transparent light-emitting element may be manufactured; the substrate may be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate may include but is not limited to plastic, polymer, metal, semiconductor wafer or glass. Preferably, the substrate includes at least one smooth surface for forming the anode on the surface. More preferably, the surface has no surface defects. Preferably, the material of the substrate 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 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.

[0131] In some embodiments, the mixture layer or the luminescent layer can be formed by a printing or coating process of the composition. The printing or coating process includes inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slit extrusion coating, etc. Preferably, it is gravure printing, nozzle printing and inkjet printing.

[0132] 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.

[0133] In the composition, the mass fraction of the organic compound as described above may be 0.01% to 10%, preferably 0.1% to 15%, more preferably 0.2% to 5%, most preferably 0.25% to 3%.

[0134] Preferably, 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 The range of δh (hydrogen bond force) is 0.9~14.2MPa1 / 2 The range is preferably 2.0 to 6.0 MPa. 1 / 2 range.

[0135] Preferably, 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 is beneficial for preventing the nozzle of the inkjet print head from clogging during inkjet printing, and the higher the boiling point, the more beneficial it is for preventing clogging.

[0136] The dispersant may include at least one organic solvent, which may be evaporated from the solvent system to form a film containing a functional material. The organic solvent may include at least one first organic solvent, which 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.

[0137] 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.

[0138] 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 ethyl ether, 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.

[0139] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, such as 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, such as 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.

[0140] The first organic solvent may be selected from organic ester solvents. Specifically, the first solvent may 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.

[0141] 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.

[0142] In addition to the dispersoid and the dispersant, the composition may also include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0143] The exemplary preparation methods of the organic compounds provided by the present invention are shown in the following exemplary embodiments 1 to 15.

[0144] Example 1

[0145] Organic compound M1 Synthesis

[0146] The synthetic route of organic compound M1 is as follows:

[0147]

[0148] The specific synthesis steps of organic compound M1 are as follows:

[0149] Synthesis of intermediate M1-3: Under nitrogen environment, (30.8 g, 100 mmol) of intermediate M1-1, (28.1 g, 100 mmol) of compound M1-2, (2.76 g, 3 mmol) of compound Pd2(dba)3, (1.2 g, 6 mmol) of compound tri-tert-butylphosphine, (18.2 g, 200 mmol) of compound sodium tert-butoxide and 250 mL of anhydrous toluene solvent were mixed and heated to 60 ° C. The reaction was stirred for 6 hours, cooled to room temperature, quenched with water twice, and the reaction solution was rotary evaporated to remove most of the solvent. The reaction solution was dissolved with dichloromethane and washed with water 3 times. The organic liquid was collected and mixed with silica gel for column chromatography purification with a yield of 75%.

[0150] Synthesis of intermediate M1-6: Under nitrogen environment, (25.6 g, 60 mmol) of intermediate M1-4, (8.9 g, 60 mmol) of compound M1-5, (1.66 g, 1.8 mmol) of compound Pd2(dba)3, (0.72 g, 3.6 mmol) of compound tri-tert-butylphosphine, (11 g, 120 mmol) of compound sodium tert-butoxide and 150 mL of anhydrous toluene solvent were mixed and heated to 90 ° C. The reaction was stirred for 6 hours, cooled to room temperature, quenched with water twice, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved with dichloromethane and washed with water 3 times, and the organic liquid was collected and mixed with silica gel for column chromatography purification, with a yield of 68%.

[0151] Synthesis of intermediate M1-7: According to the synthesis method of compound M1-6, compounds M1-3 and M1-6 replaced compounds M1-4 and 1-5 respectively, with a yield of 72%.

[0152] Synthesis of organic compound M1: Under nitrogen environment, (20.2 g, 20 mmol) compound M1-7 and 100 mL anhydrous tetrahydrofuran were mixed, cooled to -30°C, and 25 mmol of tert-butyl lithium solution was slowly added dropwise. After the addition was completed, the reaction was heated to 60°C and stirred for 2 hours. The reaction was cooled to -30°C, and 30 mmol of boron tribromide was added at once. The reaction was naturally heated to room temperature for 1 hour. Then 40 mmol of N, N-diisopropylethylamine was added, and the temperature was slowly raised to 100°C for 3 hours. The reaction was terminated, cooled to room temperature, and sodium acetate aqueous solution was added to quench the reaction. Most of the solvent was evaporated by rotary evaporation, dissolved with dichloromethane and washed with water 3 times, and the organic liquid was collected and rotary evaporated for column chromatography purification. The yield was 27%. Atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M1: mass-to-charge ratio was 984 [M + ].

[0153] Example 2

[0154] Organic Compound M2 Synthesis

[0155] The synthetic route of organic compound M2 is as follows:

[0156]

[0157] The specific synthesis steps of organic compound M2 are as follows:

[0158] Synthesis of intermediate M2-3: Under nitrogen environment, add (28 g, 100 mmol) of compound M2-1, (6 g, 150 mmol) of NaOH and 100 mL of dimethylformamide into a 250 mL two-necked flask, stir and react for 1 hour, add (14.2 g, 100 mmol) of compound M2-2 at one time, stir and react for 4 hours, after the reaction is completed, invert the reaction solution into 400 mL of pure water, stir and filter to obtain a solid, and use ethanol and dichloromethane and a mixed solution for recrystallization and purification, with a yield of 84%.

[0159] Synthesis of intermediate M2-5: According to the synthesis method of compound M1-3, compounds M2-3 and M2-4 replaced compounds M1-1 and 1-2 respectively, with a yield of 70%.

[0160] Synthesis of intermediate M2-7: According to the synthesis method of compound M1-6, compounds M2-5 and M2-6 replaced compounds M1-4 and 1-5 respectively, with a yield of 74%.

[0161] Synthesis of organic compound M2: According to the synthesis method of compound M1, compound M2-7 was substituted for compound M1-7, and the yield was 26%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M2: mass-to-charge ratio was 957 [M + ].

[0162] Example 3

[0163] Organic Compound M3 Synthesis

[0164] The synthetic route of organic compound M3 is as follows:

[0165]

[0166] The specific synthesis steps of organic compound M3 are as follows:

[0167] Synthesis of intermediate M3-2: According to the synthesis method of compound M1-3, compounds M3-1 and M2-4 were used to replace compounds M1-1 and 1-2, respectively, with a yield of 71%.

[0168] Synthesis of intermediate M3-5: According to the synthesis method of compound M1-6, compound M3-3 and twice the molar amount of M3-4 were used to replace compounds M1-4 and 1-5, respectively, with a yield of 72%.

[0169] Synthesis of intermediate M3-7: According to the synthesis method of compound M1-7, compounds M3-5 and M3-6 replaced compounds M1-6 and 1-3 respectively, with a yield of 62%.

[0170] Synthesis of intermediate M3-8: According to the synthesis method of compound M1-7, compounds M3-7 and M3-2 were used to replace compounds M1-6 and 1-3, respectively, with a yield of 68%.

[0171] Synthesis of organic compound M3: According to the synthesis method of compound M1, compound M3-8 was substituted for compound M1-7, and the yield was 28%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M3: mass-to-charge ratio: 943 [M + ].

[0172] Example 4

[0173] Organic Compound M4 Synthesis

[0174] The synthetic route of organic compound M4 is as follows:

[0175]

[0176] The specific synthesis steps of organic compound M4 are as follows:

[0177] Synthesis of intermediate M4-2: According to the synthesis method of compound M1-3, compounds M4-1 and M2-4 were used to replace compounds M1-1 and 1-2, respectively, with a yield of 75%.

[0178] Synthesis of intermediate M4-3: According to the synthesis method of compound M1-6, compounds M4-2 and M2-6 replaced compounds M1-4 and 1-5 respectively, with a yield of 73%.

[0179] Synthesis of organic compound M4: According to the synthesis method of compound M1, compound M4-3 was substituted for compound M1-7, and the yield was 24%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M4: mass-to-charge ratio: 944 [M + ].

[0180] Example 5

[0181] Organic Compound M5 Synthesis

[0182] The synthetic route of organic compound M5 is as follows:

[0183]

[0184] The specific synthesis steps of organic compound M5 are as follows:

[0185] Synthesis of intermediate M5-2: According to the synthesis method of compound M1-3, compounds M5-1 and M2-4 were used to replace compounds M1-1 and 1-2, respectively, with a yield of 73%.

[0186] Synthesis of intermediate M5-5: According to the synthesis method of compound M1-6, compounds M5-3 and M5-4 were used to replace compounds M1-4 and 1-5, respectively, with a yield of 75%.

[0187] Synthesis of intermediate M5-6: According to the synthesis method of compound M1-6, compounds M5-2 and M5-5 replaced compounds M1-4 and 1-5 respectively, with a yield of 71%.

[0188] Synthesis of organic compound M5: Under nitrogen environment, (28.5 g, 30 mmol) compound M5-6 and 50 mL o-dichlorobenzene were mixed, 35 mmol boron tribromide was slowly added under stirring, the temperature was raised to 180°C for reaction for 12 hours, the temperature was lowered to room temperature, 60 mmol diisopropylethylamine was added, the reaction was continued at room temperature for 1 hour, water was added twice to quench the reaction, the mixture was extracted with dichloromethane, washed with water three times, the organic liquid was collected and mixed with silica gel for column chromatography purification, and the yield was 26%. Atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M5: mass-to-charge ratio: 959 [M +].

[0189] Example 6

[0190] Organic Compound M6 Synthesis

[0191] The synthetic route of organic compound M6 is as follows:

[0192]

[0193] The specific synthesis steps of organic compound M6 are as follows:

[0194] Synthesis of intermediate M6-2: According to the synthesis method of compound M1-3, compound M6-1 was substituted for compound M1-1, with a yield of 76%.

[0195] Synthesis of intermediate M6-5: According to the synthesis method of compound M1-3, compounds M6-4 and M6-3 replaced compounds M1-1 and 1-2 respectively, with a yield of 72%.

[0196] Synthesis of intermediate M6-6: According to the synthesis method of compound M1-6, compound M6-5 was used instead of compound M1-4, with a yield of 70%.

[0197] Synthesis of intermediate M6-7: According to the synthesis method of compound M1-6, compounds M6-2 and M6-6 replaced compounds M1-4 and 1-5 respectively, with a yield of 73%.

[0198] Synthesis of organic compound M6: According to the synthesis method of compound M1, compound M6-7 was substituted for compound M1-7, and the yield was 24%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M6: mass-to-charge ratio: 958 [M + ].

[0199] Example 7

[0200] Organic Compound M7 Synthesis

[0201] The synthetic route of organic compound M7 is as follows:

[0202]

[0203] The specific synthesis steps of organic compound M7 are as follows:

[0204] Synthesis of intermediate M7-3: Under a nitrogen environment, (15 g, 100 mmol) of compound M7-1, (35.2 g, 100 mmol) of compound M7-2, (3.3 g, 3 mmol) of tetrakis(triphenylphosphine)palladium, (20.6 g, 150 mmol) of potassium carbonate in 40 mL of aqueous solution and 200 mL of toluene were mixed, heated with stirring to 110°C for 12 hours, the reaction was terminated, cooled to room temperature, the filtrate was filtered, the filtrate was collected, most of the solvent was evaporated by rotary evaporation, dissolved with dichloromethane, washed with water 3 times, the organic liquid was collected and mixed with silica gel for column chromatography purification, with a yield of 72%.

[0205] Synthesis of intermediate M7-5: Under nitrogen environment, (19.8 g, 60 mmol) of compound M7-3, (9 g, 60 mmol) of compound M7-4, (0.57 g, 3 mmol) of CuI, (13.8 g, 100 mmol) of potassium carbonate and 150 mL of dimethylformamide were mixed, heated to 110 ° C, stirred for 12 hours, cooled to room temperature, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved with dichloromethane and washed with water 3 times, and the organic liquid was collected and mixed with silica gel for column chromatography purification, with a yield of 61%.

[0206] Synthesis of intermediate M7-6: According to the synthesis method of compound M1-6, compound M7-5 was used instead of compound M1-4, with a yield of 72%.

[0207] Synthesis of intermediate M7-7: According to the synthesis method of compound M1-6, compounds M1-3 and M7-6 replaced compounds M1-4 and 1-5 respectively, with a yield of 70%.

[0208] Synthesis of organic compound M7: According to the synthesis method of compound M1, compound M7-7 was substituted for compound M1-7, and the yield was 29%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M7: mass-to-charge ratio: 957 [M + ].

[0209] Example 8

[0210] Organic Compound M8 Synthesis

[0211] The synthetic route of organic compound M8 is as follows:

[0212]

[0213] The specific synthesis steps of organic compound M8 are as follows:

[0214] Synthesis of intermediate M8-3: According to the synthesis method of compound M7-3, compounds M8-1 and M8-2 were used to replace compounds M7-1 and M7-2, respectively, with a yield of 58%.

[0215] Synthesis of intermediate M8-4: Under nitrogen environment, (18.8 g, 60 mmol) of compound M8-3 and (60.6 g, 150 mmol) of triethyl phosphine were mixed, heated to 190 °C with stirring for 12 hours. After the reaction was completed, most of the solvent was distilled off under reduced pressure from the reaction solution, dissolved in dichloromethane and washed with water 3 times, and the organic liquid was collected and mixed with silica gel for column chromatography purification with a yield of 76%.

[0216] Synthesis of intermediate M8-5: Under nitrogen environment, (11.2 g, 40 mmol) of compound M8-4, (3.2 g, 80 mmol) of NaOH and 80 mL of dimethylformamide were added to a 250 mL two-necked bottle, stirred for reaction for 1 hour, and (5.7 g, 40 mmol) of iodomethane was added at one time, stirred for reaction for 4 hours, and after the reaction was completed, the reaction solution was inverted into 300 mL of pure water, stirred and filtered to obtain a solid, which was recrystallized and purified with a mixed solution of ethanol and dichloromethane, with a yield of 80%.

[0217] Synthesis of intermediate M8-6: According to the synthesis method of compound M1-3, compounds M8-5 and M2-4 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 73%.

[0218] Synthesis of intermediate M8-8: According to the synthesis method of compound M1-3, compound M8-7 and twice the molar amount of M2-4 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 65%.

[0219] Synthesis of intermediate M8-9: According to the synthesis method of compound M7-5, compounds M8-6 and M8-8 replaced compounds M7-3 and M7-4 respectively, with a yield of 62%.

[0220] Synthesis of organic compound M8: According to the synthesis method of compound M5, compound M8-9 was substituted for compound M5-6, and the yield was 28%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M8: mass-to-charge ratio: 867 [M + ].

[0221] Example 9

[0222] Organic Compound M9 Synthesis

[0223] The synthetic route of organic compound M9 is as follows:

[0224]

[0225] The specific synthesis steps of organic compound M9 are as follows:

[0226] Synthesis of intermediate M9-1: According to the synthesis method of compound M1-3, compounds M7-2 and M2-4 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 68%.

[0227] Synthesis of intermediate M9-3: According to the synthesis method of compound M7-5, compounds M9-1 and M9-2 were used to replace compounds M7-3 and M7-4, respectively, with a yield of 65%.

[0228] Synthesis of intermediate M9-4: According to the synthesis method of compound M1-6, compounds M9-3 and M5-4 were used to replace compounds M1-4 and M1-5, respectively, with a yield of 71%.

[0229] Synthesis of intermediate M9-5: According to the synthesis method of compound M1-6, compounds M4-2 and M9-4 were used to replace compounds M1-4 and M1-5, respectively, with a yield of 66%.

[0230] Synthesis of compound M9: According to the synthesis method of compound M1, compound M9-5 was substituted for compound M1-7, and the yield was 26%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M9: mass-to-charge ratio: 854 [M + ].

[0231] Example 10

[0232] Organic Compound M10 Synthesis

[0233] The synthetic route of organic compound M10 is as follows:

[0234]

[0235] The specific synthesis steps of organic compound M10 are as follows:

[0236] Synthesis of intermediate M10-2: According to the synthesis method of compound M1-3, compounds M10-1 and M2-4 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0237] Synthesis of intermediate M10-5: According to the synthesis method of compound M1-3, compounds M10-4 and M10-3 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 65%.

[0238] Synthesis of intermediate M10-6: According to the synthesis method of compound M7-5, compounds M10-2 and M10-5 replaced compounds M7-3 and M7-4 respectively, with a yield of 70%.

[0239] Synthesis of organic compound M10: According to the synthesis method of compound M1, compound M10-6 was substituted for compound M1-7, and the yield was 26%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M10: mass-to-charge ratio: 829 [M + ].

[0240] Embodiment 11

[0241] Organic Compound M11 Synthesis

[0242] The synthetic route of organic compound M11 is as follows:

[0243]

[0244] The specific synthesis steps of organic compound M11 are as follows:

[0245] Synthesis of intermediate M11-2: According to the synthesis method of compound M1-3, compound M11-1 was substituted for compound M1-1, with a yield of 62%.

[0246] Synthesis of intermediate M11-4: Under nitrogen environment, (22.7 g, 100 mmol) of compound M11-3 and 100 mL of anhydrous tetrahydrofuran solvent were mixed, stirred to dissolve, cooled to -78 °C, 100 mmol of n-butyl lithium was slowly added dropwise, reacted for 2 hours, 150 mmol of deuterated water was added at one time, the reaction solution was slowly warmed to room temperature, and the stirring reaction was continued for 4 hours. After the reaction was completed, most of the solvent was evaporated from the reaction solution by rotary evaporation, dissolved with dichloromethane and washed with water 3 times, the organic liquid was collected and mixed with silica gel for column chromatography purification, with a yield of 72%.

[0247] Synthesis of intermediate M11-5: Under nitrogen environment, (9 g, 60 mmol) of compound M11-3, (9 g, 60 mmol) of compound M7-4, (39 g, 120 mmol) of cesium carbonate and 150 mL of dimethylformamide were mixed and refluxed for 12 hours. After the reaction, the reaction solution was cooled to room temperature, most of the solvent was evaporated by rotary evaporation, extracted with dichloromethane, washed three times with water, and the organic liquid was collected and mixed with silica gel for column chromatography purification with a yield of 62%.

[0248] Synthesis of intermediate M11-6: According to the synthesis method of compound M11-5, compounds M11-5 and M11-2 were used to replace compounds M11-4 and M7-4, respectively, with a yield of 73%.

[0249] Synthesis of organic compound M11: According to the synthesis method of compound M1, compound M11-6 was substituted for compound M1-7, and the yield was 35%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M11: mass-to-charge ratio: 723 [M + ].

[0250] Example 12

[0251] Organic Compound M12 Synthesis

[0252] The synthetic route of organic compound M12 is as follows:

[0253]

[0254] The specific synthesis steps of organic compound M12 are as follows:

[0255] Synthesis of intermediate M12-2: According to the synthesis method of compound M8-5, compound M12-1 was used instead of compound M8-4, with a yield of 78%.

[0256] Synthesis of intermediate M12-3: According to the synthesis method of compound M1-3, compound M12-2 was used instead of compound M1-1, with a yield of 76%.

[0257] Synthesis of intermediate M12-4: Under nitrogen, (19.6 g, 40 mmol) of compound M12-2 and 100 mL of dichloromethane were added to a 350 mL three-necked flask. 60 mmol of dichloromethane solution of boron tribromide was slowly added under ice bath, and the reaction was allowed to slowly rise to room temperature. The reaction was continued to stir at room temperature for 24 hours. Water was added to quench the reaction, and the mixture was extracted with dichloromethane, washed with water three times, and the organic solution was collected and mixed with silica gel for column chromatography purification, with a yield of 72%.

[0258] Synthesis of intermediate M12-5: According to the synthesis method of compound M7-3, compound M11-3 was used instead of compound M7-2, with a yield of 78%.

[0259] Synthesis of intermediate M12-6: According to the synthesis method of compound M11-5, compound M12-5 was used instead of compound M11-4, with a yield of 64%.

[0260] Synthesis of intermediate M12-7: According to the synthesis method of compound M11-5, compounds M12-6 and M12-4 were used to replace compounds M11-4 and M7-4, respectively, with a yield of 70%.

[0261] Synthesis of organic compound M12: According to the synthesis method of compound M1, compound M12-7 was substituted for compound M1-7, and the yield was 33%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M12: mass-to-charge ratio: 813 [M + ].

[0262] Embodiment 13

[0263] Organic Compound M13 Synthesis

[0264] The synthetic route of organic compound M13 is as follows:

[0265]

[0266] The specific synthesis steps of organic compound M13 are as follows:

[0267] Synthesis of intermediate M13-2: According to the synthesis method of compound M1-3, compounds M13-1 and M2-4 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 67%.

[0268] Synthesis of intermediate M13-3: According to the synthesis method of compound M1-3, compounds M11-3 and M2-4 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 65%.

[0269] Synthesis of intermediate M13-4: According to the synthesis method of compound M11-5, compounds M13-3 and M9-2 were used to replace compounds M11-4 and M7-4, respectively, with a yield of 62%.

[0270] Synthesis of intermediate M13-5: According to the synthesis method of compound M11-5, compounds M13-4 and M13-2 were used to replace compounds M11-4 and M7-4, respectively, with a yield of 60%.

[0271] Synthesis of organic compound M13: According to the synthesis method of compound M1, compound M13-5 was substituted for compound M1-7, and the yield was 33%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M13: mass-to-charge ratio: 765 [M + ].

[0272] Embodiment 14

[0273] Organic Compound M14 Synthesis

[0274] The synthetic route of organic compound M14 is as follows:

[0275]

[0276] The specific synthesis steps of organic compound M14 are as follows:

[0277] Synthesis of intermediate M14-2: According to the synthesis method of compound M1-3, compound M14-1 was substituted for compound M1-1, with a yield of 69%.

[0278] Synthesis of intermediate M14-5: According to the synthesis method of compound M7-5, compounds M14-4 and M14-3 were used to replace compounds M7-3 and M7-4, respectively, with a yield of 68%.

[0279] Synthesis of intermediate M14-6: According to the synthesis method of compound M7-5, compounds M14-2 and M14-5 replaced compounds M7-3 and M7-4 respectively, with a yield of 62%.

[0280] Synthesis of organic compound M14: According to the synthesis method of compound M1, compound M14-6 was substituted for compound M1-7, and the yield was 34%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M14: mass-to-charge ratio: 698 [M + ].

[0281] Embodiment 15

[0282] Organic Compound M15 Synthesis

[0283] The synthetic route of organic compound M15 is as follows:

[0284]

[0285] The specific synthesis steps of organic compound M15 are as follows:

[0286] Synthesis of intermediate M15-1: According to the synthesis method of compound M1-3, compound M3-1 was substituted for compound M1-1, with a yield of 70%.

[0287] Synthesis of intermediate M15-3: According to the synthesis method of compound M1-6, compounds M15-1 and M15-2 were used to replace compounds M1-4 and 1-5, respectively, with a yield of 73%.

[0288] Synthesis of intermediate M15-4: According to the synthesis method of compound M1-7, compounds M15-1 and M15-2 were used to replace compounds M1-3 and 1-6, respectively, with a yield of 64%.

[0289] Synthesis of intermediate M15-5: According to the synthesis method of compound M1-7, compounds M15-4 and M1-2 were used to replace compounds M1-3 and 1-6, respectively, with a yield of 69%.

[0290] Synthesis of organic compound M15: According to the synthesis method of compound M1, compound M15-5 was substituted for compound M1-7, and the yield was 30%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M15: mass-to-charge ratio: 990 [M + ].

[0291] Example 16

[0292] Organic Compound M16 Synthesis

[0293] The synthetic route of organic compound M16 is as follows:

[0294]

[0295] The specific synthesis steps of organic compound M16 are as follows:

[0296] Synthesis of intermediate M16-2: According to the synthesis method of compound M1-3, compound M16-1 was substituted for compound M1-1, with a yield of 72%.

[0297] Synthesis of intermediate M16-3: According to the synthesis method of compound M1-6, compounds M16-2 and M1-6 replaced compounds M1-4 and 1-5 respectively, with a yield of 74%.

[0298] Synthesis of organic compound M16: According to the synthesis method of compound M1, compound M16-3 was substituted for compound M1-7, and the yield was 28%. The results of atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) of organic compound M16: mass-to-charge ratio: 958 [M + ].

[0299] The exemplary manufacturing steps of the light-emitting element provided by the present invention are shown in the following exemplary embodiment 17.

[0300] Embodiment 17

[0301] In this embodiment, the preparation steps of the light-emitting element having anode (ITO) / hole injection layer (40nm) / hole transport layer (100nm) / light-emitting layer (host material: 3% (mass ratio) guest material) (50nm) / electron transport layer (25nm) / cathode (LiQ (1nm) / Al (150nm) are as follows:

[0302] a. Cleaning of the conductive glass substrate: When used for the first time, it can be cleaned with a variety of solvents, such as chloroform, ketone, isopropanol, and then treated with ultraviolet ozone plasma;

[0303] b. The hole injection layer (40 nm), hole transport layer (100 nm), light emitting layer (50 nm), and electron transport layer (25 nm) were sequentially deposited in a high vacuum (1 × 10 -6 mbar) medium heat evaporation film forming;

[0304] c. Cathode: LiQ (1nm) / Al (150nm) in high vacuum (1×10 -6 mbar) by thermal evaporation;

[0305] d. Packaging: The device is encapsulated with UV-curable resin in a nitrogen glove box.

[0306] In this embodiment, the guest materials are organic compounds M1-M16 to form light-emitting elements 1-16, and the guest material is Ref-1 to form a contrast element 1.

[0307] The structural formula of Ref-1 is:

[0308] In the light emitting elements 1 to 16, and the comparative element 1,

[0309] The structural formula of the material of the hole injection layer is:

[0310] The structural formula of the material of the hole transport layer is:

[0311] The structural formula of the host material in the light-emitting layer is:

[0312] The structural formula of the material of the electron transport layer is:

[0313] The structural formula of LiQ is:

[0314] In this embodiment, external quantum efficiency (EQE) and luminescence lifetime tests (T90@1000nits, which refers to the time it takes for the device to be tested to decay from 1000 nits to 900 nits) were performed on light-emitting elements 1 to 16 and comparison element 1, and the results are shown in Table 1.

[0315] Table 1: Performance data of light-emitting elements 1 to 16 and comparative element 1

[0316] OLED Devices Object material EQE T90@1000nits Light emitting element 1 M1 1.72 1.78 Light emitting element 2 M2 1.70 1.77 Light emitting element 3 M3 1.78 1.85 Light emitting element 4 M4 1.76 1.83 Light emitting element 5 M5 1.75 1.81 Light emitting element 6 M6 1.73 1.80 Light emitting element 7 M7 1.66 1.72 Light emitting element 8 M8 1.64 1.70 Light emitting element 9 M9 1.69 1.75 Light emitting element 10 M10 1.67 1.74 Light emitting element 11 M11 1.63 1.68 Light emitting element 12 M12 1.60 1.65 Light emitting element 13 M13 1.58 1.64 Light emitting element 14 M14 1.61 1.67 Light emitting element 15 M15 1.77 1.84 Light emitting element 16 M16 1.75 1.82 Comparison Component 1 Ref-1 1 1

[0317] It can be seen from the data in Table 1 that when the external quantum efficiency and luminescence lifetime of the comparative element 1 are taken as the reference value 1, the external quantum efficiency of the light-emitting element 1 to the light-emitting element 16 is significantly improved, and the luminescence lifetime is also effectively extended. This indicates that the introduction of the amine substituent enhances the resonance effect and the steric effect of the organic compound, improves the performance of the guest material, and effectively improves the luminescence efficiency and luminescence lifetime of the light-emitting element.

[0318] The light-emitting element disclosed in the present invention uses an organic compound containing an amine group, in which both a heterocycle and an amine group are present, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, increasing the luminous efficiency of the light-emitting element and extending the luminous life of the light-emitting element.

[0319] An embodiment of the present invention further discloses a display panel, which includes any of the above-mentioned light-emitting elements.

[0320] The display panel further includes an array substrate located at one side of the light emitting element, and a packaging layer located at a side of the light emitting element away from the array substrate and covering the light emitting element.

[0321] The display panel further comprises 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, and the color filter layer can include a plurality of color resists and a black matrix located on both sides of the color resists.

[0322] The display panel disclosed in the embodiment of the present invention uses a light-emitting element of an organic compound containing an amine group, in which the organic compound has both a heterocycle and an amine group, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, improving the luminous efficiency of the light-emitting element and extending the luminous life of the light-emitting element, thereby improving the luminous efficiency of the display panel and extending the service life of the display panel.

[0323] The embodiment of the present invention discloses an organic compound, a light-emitting element and a display panel. The organic compound has a structure as shown in the general formula (1): The present invention uses an amine-containing organic compound, in which both a heterocycle and an amine group are present, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, increasing the luminous efficiency of the light-emitting element and extending the luminous life of the light-emitting element.

[0324] The above is a detailed introduction to an organic compound, a light-emitting element and a display panel provided in the embodiments of the present invention. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core idea. At the same time, for those skilled in the art, according to the idea of ​​the present invention, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as a limitation on the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in general formula (14) or general formula (15): General formula (14); General formula (15); wherein Z is selected from CR1R2, NR3, O or S; X and Y are independently selected from O or NR4; R1-R3 are selected from alkyl groups having 1 to 20 carbon atoms; R4 is selected from substituted or unsubstituted phenyl; R1 and R2 are independent of each other; Ar1 is selected from H, D, an alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted phenyl group; Ar2, Ar3 and Ar4 are independently selected from substituted or unsubstituted phenyl; Ar5 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl; Ar6, Ar7, Ar8 and Ar9 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; The substituent used in the substitution is selected from an alkyl group containing 1 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized in that Z is selected from CR1R2, O or S; X and Y are each independently selected from O or NR4, and X and Y are not O at the same time.

3. The organic compound according to claim 1, characterized in that The organic compound is selected from the following compounds: 。 4. A light emitting element, characterized in that: include: 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; The material of the organic functional layer includes one or more of the organic compounds described in any one of claims 1 to 3.

5. The light emitting element according to claim 4, characterized in that The organic functional layer at least includes a light-emitting layer, and the light-emitting layer includes a host material and a guest material. The guest material is one or more of the organic compounds according to any one of claims 1 to 3.

6. The light emitting element according to claim 5, characterized in that In the light-emitting layer, the mass ratio of the host material to the guest material is 99:1 to 70:

30.

7. A display panel, characterized in that: The light emitting device comprises the light emitting element as claimed in any one of claims 4 to 6.

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