Organic compound, mixture, composition and organic light-emitting device

Abstract

The invention relates to an organic compound, a mixture, a composition and an organic light-emitting device. The organic compound has a structure represented by a formula (1): # imgabs0 #. The organic compound provided by the invention can improve the hole transport capability of a hole transport material, improve the luminous efficiency of an organic light-emitting device and prolong the service life of the organic light-emitting device.

Description

Technical Field

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

[0002] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting diodes (OLEDs) that use organic electroluminescence usually have an anode and a cathode and an organic functional layer between the two. In order to improve the efficiency and life of organic electroluminescent devices, the organic functional layer may have a multilayer structure, each layer containing different organic substances, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In an organic electroluminescent device, by applying a voltage between two electrodes, holes are injected from the anode into the organic functional layer, and electrons are injected from the cathode into the organic functional layer. When the injected holes meet the electrons, excitons are formed, and the excitons emit light when they transition back to the ground state. This organic electroluminescent device has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast. OLED has the advantages of wide viewing angle, fast response time, low operating voltage, and thin panel thickness in the application of optoelectronic devices (such as flat panel displays and lighting), and therefore has broad development potential.

[0003] In order to realize efficient organic electroluminescent devices, in addition to developing high-performance luminescent materials, the development of transport materials is also very important. At present, most transport materials are small molecule materials based on carbazole derivatives, but such transport materials have the disadvantage of unbalanced hole and electron transport, which causes the light-emitting devices using such transport materials to have low luminous efficiency and short life. Summary of the invention

[0004] The embodiments of the present application provide an organic compound, a mixture, a composition and an organic light-emitting device. The organic compound provided in the present application can enhance the hole transport capability of the hole transport material and enhance the luminous efficiency and life of the organic light-emitting device.

[0005] An embodiment of the present application provides an organic compound having a structure represented by formula (1):

[0006]

[0007] in,

[0008] Ar1 is selected from any one of the following groups:

[0009]

[0010] X and Y are independently selected from O, S, NR3, CR4R5;

[0011] R1, R2, R3, R4, R5 are independently selected from H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 20 ring atoms.

[0012] In some embodiments, the Ar1 is selected from any one of the following groups:

[0013]

[0014] In some embodiments, R1, R2 are independently selected from H or tert-butyl.

[0015] In some embodiments, R3, R4, and R5 are independently selected from methyl or phenyl.

[0016] In some embodiments, the organic compound is selected from any one of formula (1-1) to formula (1-4):

[0017]

[0018] In some embodiments, the organic compound is selected from the compounds represented by the following structures:

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040] An embodiment of the present application also provides a mixture, which includes at least one organic compound as described above and at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, organic host materials or inorganic quantum dot materials.

[0041] An embodiment of the present application further provides a composition, which includes at least one organic compound as described above and at least one organic solvent, or the composition includes the mixture as described above and at least one organic solvent.

[0042] In some embodiments, the organic compound accounts for 0.01 wt % to 10 wt % of the composition, or the mixture accounts for 0.01 wt % to 10 wt % of the composition.

[0043] An embodiment of the present application further provides an organic light-emitting device, comprising:

[0044] a first electrode;

[0045] a second electrode, disposed opposite to the first electrode; and

[0046] an organic functional layer, located between the first electrode and the second electrode;

[0047] The material of the organic functional layer includes at least one organic compound as described above, or the material of the organic functional layer includes the mixture as described above.

[0048] The organic compound of the present application is an aromatic amine compound, the nitrogen atom of which is connected to a 2-position spirofluorene, a fluorene-like phenyl group and an aromatic group Ar1. The organic compound of the present application is based on an aromatic amine structure, and compared with existing carbazole derivatives, it can effectively improve the hole transport capacity. At the same time, the three chemical bonds of the nitrogen atom are respectively connected to the 2-position spirofluorene, the fluorene-like phenyl group and the aromatic group Ar1. The combination of the 2-position spirofluorene, the fluorene-like phenyl group and the aromatic group Ar1 improves the molecular stacking of the organic compound, increases the steric hindrance, and enlarges the gap between molecules, thereby improving the hole mobility of the material and improving the hole transport capacity.

[0049] In the organic compound structure of the present application, the fluorene-like phenyl group includes a fluorene-like group and a phenyl group, wherein the phenyl group is connected to the benzene ring of the fluorene-like group, the chemical connection bond is not easy to break, and the structure is stable. The Ar1 group is selected from a group with a more stable structure such as a phenyl group, a biphenyl group, a fluorene-like group, etc., so that the organic compound has a stable structure, thereby improving the rigidity of the molecule and further improving the hole transport ability of the material.

[0050] The present invention connects the aromatic amine group with the 2-position spirofluorene and the fluorene-like phenyl group, and the structure is stable, and the molecular stacking is improved, so that the organic compound molecules have greater rigidity, and the glass transition temperature of the organic compound molecules is increased. The organic compound is used as a hole transport material for a blue light organic light-emitting device, and is matched with a suitable light-emitting material to effectively improve the luminous efficiency and life of the organic light-emitting device. Therefore, the use of the organic compound of the present invention to prepare an organic light-emitting device can reduce the manufacturing cost of the organic light-emitting device, improve the luminous efficiency of the organic light-emitting device, and extend the life of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0051] Figure 1 A schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application.

[0052] Description of reference numerals:

[0053] 100, organic light-emitting device; 110, substrate; 120, first electrode; 130, organic functional layer; 131, light-emitting layer; 132, hole injection layer; 133, hole transport layer; 134, electron transport layer; 140, second electrode. DETAILED DESCRIPTION

[0054] It should be understood that the specific embodiments described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise stated, 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 accompanying drawings. In the present application, "optionally", "optional", and "optional" refer to being optional, that is, any one of the two parallel schemes of "yes" or "no". If multiple "optional" items appear in a technical scheme, unless otherwise specified and there is no contradiction or mutual restriction, each "optional" item is independent of each other. In the present application, the technical features described in an open manner include closed technical schemes composed of the listed features, and also include open technical schemes of the listed features.

[0055] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.

[0056] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0057] In the present application, 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.

[0058] In this application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen atoms, C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkylthio, C 6-30 The aromatic group, C 6-30 The aryloxy group, C 6-30 The arylthio group, C 3-30 Heteroaryl, C 1-30 Silane, C 2-10 The alkylamino group, C 6-30 Aromatic amine groups, or combinations of the above groups, etc.

[0059] In the present application, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed 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 is true for 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.

[0060] In the present application, "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, such as "C 1-9 “Alkyl” refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. 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, adamantane, and the like.

[0061] In the present application, "aryl or aromatic group" 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 group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, dinaphthylenediol, tetracene, pyrene, benzopyrene, acenaphthene, fluorene 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.

[0062] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom on the basis of an aromatic group is replaced by a non-carbon atom, and the non-carbon atom may be a N atom, an O atom, a S atom, or the like. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to 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 group is optionally further substituted. Suitable examples include, but are not limited to, triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and derivatives thereof.

[0063] In the present application, "amino" 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 amines include -NH2, -N(alkyl), -NH(alkyl), -N(cycloalkyl), -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.

[0064] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0065] In the present application, when a linking site is not specified in a group, it means that any linking site in the group can be used as a linking site;

[0066] In the present application, 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 fusion sites;

[0067] In the present application, 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] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0069] An embodiment of the present application provides an organic compound having a structure represented by formula (1):

[0070]

[0071] in,

[0072] Ar1 is selected from any one of the following groups:

[0073]

[0074] X and Y are independently selected from O, S, NR3, CR4R5;

[0075] R1, R2, R3, R4, R5 are independently selected from H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 20 ring atoms.

[0076] In some embodiments, R1, R2, R3, R4, R5 are independently selected from H, D, a linear alkyl group having 1 to 8 C atoms, a branched alkyl group having 3 to 8 C atoms, or a substituted or unsubstituted aromatic group having 5 to 10 ring atoms.

[0077] In some embodiments, R1, R2 are independently selected from H, a straight chain alkyl group having 1 to 8 C atoms, or a branched chain alkyl group having 3 to 10 C atoms.

[0078] In some embodiments, R1, R2 are independently selected from H or tert-butyl.

[0079] In some embodiments, R1 and R2 represent the same group.

[0080] In some embodiments, R3, R4, and R5 are independently selected from H, a linear alkyl group having 1 to 8 C atoms, a branched alkyl group having 3 to 8 C atoms, or a substituted or unsubstituted aromatic group having 5 to 10 ring atoms.

[0081] In some embodiments, R3, R4, and R5 are independently selected from methyl or phenyl.

[0082] In some embodiments, the Ar1 is selected from any one of the following groups:

[0083]

[0084] The organic compound of the present application is an aromatic amine compound, the nitrogen atom of which is connected to a 2-position spirofluorene, a fluorene-like phenyl group and an aromatic group Ar1. The organic compound of the present application is based on an aromatic amine structure, and compared with existing carbazole derivatives, the aromatic amine compound can effectively improve the hole transport capacity.

[0085] In the organic compound of the present application, the three chemical bonds of the nitrogen atom are respectively connected to the 2-position spirofluorene, the fluorene-like phenyl group and the aromatic group Ar1. The combination of the 2-position spirofluorene, the fluorene-like phenyl group and the aromatic group Ar1 improves the molecular stacking of the organic compound, increases the steric hindrance, and enlarges the gap between molecules, thereby improving the hole mobility of the material and improving the hole transport capacity.

[0086] In the organic compound structure of the present application, the fluorene-like phenyl group includes a fluorene-like group and a phenyl group, wherein the phenyl group is connected to the benzene ring of the fluorene-like group, and the chemical bond between the phenyl group and the fluorene-like group is not easy to break, and the structure is more stable. Compared with the 9-phenylfluorene structure, the phenyl group in the 9-phenylfluorene structure is connected to the 9-carbon atom of the fluorene group, and the bond connected to the 9-carbon atom is very easy to break, and the molecular structure is unstable, which easily leads to the decrease of the molecular rigidity, glass transition temperature, and thermal decomposition temperature of the material, thereby causing the overall hole transport capacity of the material to decrease, and the phenyl group in the fluorene-like phenyl group of the present application is connected to the benzene ring of the fluorene-like group, and the chemical bond is not easy to break, compared with the 9-phenylfluorene structure, the structure is more stable, the molecular rigidity is greater, and therefore the glass transition temperature and thermal decomposition temperature of the organic compound molecule are increased, and the hole transport capacity of the material is increased. In addition, in the fluorene-like phenyl group of the present application, only one phenyl group is connected to the fluorene-like group. Compared with organic compounds in which multiple phenyl groups or groups with larger molecular weight are connected to the fluorene-like group, too large a molecular weight is not conducive to hole transport, which will cause the efficiency, stability and life of the device to decrease. The fluorene-like phenyl group of the present application has only one phenyl group connected to the fluorene-like group. While improving the degree of molecular stacking, it will not make the molecular weight too large, and can effectively improve the hole transport ability.

[0087] In the structure of the organic compound of the present application, the Ar1 group is selected from structures such as phenyl, biphenyl, and fluorene-like groups, which can change the molecular stacking at the molecular level, increase the steric hindrance, make the molecular gap larger, improve the hole mobility of the material, and then improve the hole transmission capacity. At the same time, the Ar1 group of the present application is selected from more stable groups such as phenyl, biphenyl, and fluorene-like groups, so that the organic compound has a stable structure, thereby improving the rigidity of the molecule, and further improving the hole transmission capacity of the material. In addition, the Ar1 group of the present application will not make the molecular weight too large while improving the degree of molecular stacking, and can effectively improve the hole transmission capacity.

[0088] In summary, the present application connects the aromatic amine group with the 2-position spirofluorene and the fluorene-like phenyl group, and the structure is stable, and the molecular stacking is improved, so that the organic compound molecules have greater rigidity, thereby increasing the glass transition temperature of the organic compound molecules. The use of the organic compound of the present application to prepare an organic light-emitting device can reduce the manufacturing cost of the organic light-emitting device, improve the luminous efficiency of the organic light-emitting device, and extend the life of the organic light-emitting device.

[0089] In some embodiments, the formula (1) is selected from any one of formula (1-1) to formula (1-4):

[0090]

[0091]

[0092] In the present application, X in the fluorene-like phenyl group may represent O or S. When X in the fluorene-like phenyl group is O or S, the organic compound has better hole and electron transport capabilities, which is more conducive to improving the hole transport capability of the material.

[0093] In some embodiments, the organic compound is selected from the compounds represented by the following structures:

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] Wherein, H in the above structure can be further substituted arbitrarily.

[0116] In the present application, the organic compound is an aromatic amine organic compound, which can be used as an organic functional material in the organic functional layer of an organic light-emitting device, especially an OLED device. The organic functional materials include hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), luminescent guest materials (Guest Emitter), host materials (Host Emitter), etc. Among them, the host material includes phosphorescent host materials, fluorescent host materials, TADF luminescent materials, etc. The organic compound of the present application can be used as any one of the above-mentioned organic functional materials.

[0117] Preferably, the organic compound can be used as a hole transport material.

[0118] In some embodiments, the glass transition temperature of the organic compound is Tg≥100°C, preferably Tg≥120°C, more preferably Tg≥140°C, more preferably Tg≥160°C, and most preferably Tg≥180°C.

[0119] In some embodiments, the HOMO (Highest Occupied Molecular Orbital) energy level of the organic compound satisfies ((HOMO-(HOMO-1))≥0.2eV, preferably ((HOMO-(HOMO-1))≥0.3eV, more preferably ((HOMO-(HOMO-1))≥0.4eV, and more preferably ((HOMO-(HOMO-1))≥0.45eV. The LUMO (Lowest Unoccupied Molecular Orbital) energy level of the organic compound satisfies (((LUMO+1)-LUMO)≥0.15eV, preferably (((LUMO+1)-LUMO)≥0.25eV, more preferably (((LUMO+1)-LUMO)≥0.30eV, and more preferably (((LUMO+1)-LUMO)≥0.35eV.

[0120] In some embodiments, the organic compound is an aromatic amine organic compound, which can be used as a hole transport layer material for a blue light device. In order to achieve color display, the display device generally includes devices of three colors: red, green, and blue. Since the HOMO and LUMO energy levels of the light-emitting layer material of the blue light device are different from those of the light-emitting layer materials of the green and red light devices, in order to allow positive and negative charge carriers to fully recombine in the light-emitting layer, the hole transport material close to the light-emitting layer must have a suitable HOMO and LUMO energy level to block the flow of electrons from the light-emitting layer to the hole transport material. The organic compound of the present application introduces 2-position spirofluorene and fluorene-like phenyl groups on the aromatic amine group, which improves the stacking of the molecules and increases the rigidity of the molecules, so that the chemical structure of the organic compound is relatively stable, has a good device life, suitable HOMO and LUMO energy levels, good solubility, film-forming properties, and good solvent resistance after curing, so that the organic compound of the present application is suitable as a hole transport layer material in a blue light organic light-emitting device. The organic compound is used as a hole transport material for a blue light organic light-emitting device in combination with a suitable light-emitting material, which can effectively improve the light-emitting efficiency and life of the organic light-emitting device.

[0121] The embodiment of the present application also provides a mixture, the mixture includes at least one organic compound as described above and at least one organic functional material, the organic functional material is selected from hole injection material, hole transport material, electron transport material, electron injection material, electron blocking material, hole blocking material, luminescent material, host material or inorganic quantum dot material. For example, various organic functional materials are described in detail in patents WO2010135519A1, US20090134784A1 and WO 2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0122] In some embodiments, the organic functional material may be a small molecule material or a polymer material.

[0123] In one embodiment, the organic functional material may be an electron transport material, and the organic functional material may be mixed with the organic compound of the present application and used as a co-host in an organic light-emitting device.

[0124] In some embodiments, the organic compound can be applied to vapor deposition type OLED, and the molecular weight of the organic compound is ≤1100 g / mol, preferably ≤1000 g / mol, more preferably ≤950 g / mol, more preferably ≤900 g / mol, and most preferably ≤800 g / mol.

[0125] In some embodiments, the organic compound can be applied to printed OLEDs, and the molecular weight of the organic compound is ≥700 g / mol, preferably ≥900 g / mol, more preferably ≥1000 g / mol, and even more preferably ≥1100 g / mol.

[0126] An embodiment of the present application further provides a composition, which includes at least one organic compound as described above and at least one organic solvent, or the composition includes the mixture as described above and at least one organic solvent.

[0127] Wherein, the organic solvent comprises at least one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, boric acid esters or phosphate compounds. Preferably, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0128] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic solvents. Aromatic or heteroaromatic solvents include but are not limited to: 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-methyl isopropylbenzene, 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.

[0129] In some embodiments, the organic solvent is selected from aromatic ketone-based solvents. Aromatic ketone-based solvents include but are not limited to: 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.

[0130] In some embodiments, the organic solvent is selected from aromatic ether-based solvents. Aromatic ether-based solvents include but are not limited to: 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.

[0131] In some embodiments, the organic solvent is selected from a solvent based on aliphatic ketone or aliphatic ether. Aliphatic ketone-based solvents include but are not limited to: 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.; aliphatic ether-based solvents include but are not limited to: 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.

[0132] In some embodiments, the organic solvent is selected from ester-based solvents. Ester-based solvents include but are not limited to: 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.

[0133] In some embodiments, the composition further comprises at least one of the organic compounds or the mixture, at least one of the organic solvents and at least one cosolvent. The cosolvent includes but is not limited to: at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0134] In the present application, the above organic solvents may be used alone or in combination of two or more organic solvents.

[0135] In some embodiments, the organic solvent of the present application may be a solvent having a Hansen solubility parameter within the following range:

[0136] δd (dispersion force) is between 17.0 and 23.2 MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 scope;

[0137] δp (polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0138] δh (hydrogen bond force) is between 0.9 and 14.2 MPa1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0139] In the composition of the present application, the boiling point parameter of the organic solvent should be considered when selecting. The boiling point of the organic solvent of the present application is ≥150°C, preferably ≥180°C, more preferably ≥200°C, more preferably ≥250°C, and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of inkjet print heads. In the present application, the organic solvent can be evaporated from the solvent system to form a film containing organic functional materials.

[0140] In some embodiments, the composition can be a solution.

[0141] In some embodiments, the composition may be a suspension.

[0142] In some embodiments, the content of the organic compound or the mixture in the composition is 0.01 wt% to 10 wt%; preferably 0.1 wt% to 8 wt%; more preferably 0.2 wt% to 5 wt%; optimally 0.25 wt% to 3 wt%.

[0143] In some embodiments, the composition can be used as a coating or printing ink for preparing an organic light-emitting device, for example, the organic light-emitting device can be prepared by printing or coating.

[0144] The printing or coating method includes, but is not limited to, 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. Preferred are gravure printing, nozzle printing and inkjet printing.

[0145] In some embodiments, the composition may further include one or more other components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., to adjust the viscosity, film-forming properties, adhesion properties, etc. of the composition.

[0146] The organic compound, the mixture and the composition provided in the present application can be used in an organic light-emitting device.

[0147] In some embodiments, the organic compound can be applied to an OLED device; further, the organic compound can be applied to a hole transport layer of an OLED device.

[0148] See also Figure 1 , an embodiment of the present application provides an organic light-emitting device 100, comprising:

[0149] A first electrode 120;

[0150] A second electrode 140, disposed opposite to the first electrode 120;

[0151] An organic functional layer 130 is located between the first electrode 120 and the second electrode 140;

[0152] The material of the organic functional layer 130 includes at least one organic compound as described above, or the material of the organic functional layer 130 includes a mixture as described above.

[0153] The organic light-emitting device may be, but is not limited to, an organic electroluminescent element (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light-emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (OPV).

[0154] For details, please refer to Figure 1 , is a schematic diagram of the structure of an organic light-emitting device provided in the present application. The organic light-emitting device 100 includes a substrate 110, a first electrode 120 located on the substrate, an organic functional layer 130 located on a side of the first electrode 120 away from the substrate 110, and a second electrode 140 located on a side of the organic functional layer 130 away from the first electrode 120. The organic light-emitting device 100 may be an OLED device, but is not limited thereto.

[0155] The substrate 110 may be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device may be manufactured. The substrate 110 may be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 110 may include but is not limited to plastic, polymer, metal, semiconductor wafer or glass. Preferably, the substrate 110 includes at least one smooth surface to form the first electrode 120 on the surface. More preferably, the surface has no 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).

[0156] The first electrode 120 may be an anode, which is an electrode for injecting holes, and the anode may inject holes into the organic functional layer, 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. 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 a patterned structure, such as: patterned ITO conductive substrates are commercially available and can be used to prepare the organic light-emitting device of the present application.

[0157] The second electrode 140 may be a cathode, which is an electrode for injecting electrons, and the cathode may inject electrons into the organic functional layer, such as injecting 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. 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 light-emitting devices may be used as cathode materials of the device of the present application, 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.

[0158] The organic functional layer 130 includes one or more film layers, and the organic functional layer 130 may include at least one of a light emitting layer 131, a hole injection layer (HIL) 132, a hole transport layer (HTL) 133, an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL) 134, and a hole blocking layer (HBL). Detailed descriptions of various organic functional materials included in the organic functional layer 130 are detailed in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0159] In some embodiments, the organic functional layer 130 includes at least a light emitting layer 131 and a hole transport layer 133 .

[0160] In some embodiments, the light-emitting material of the light-emitting layer 131 is selected from a singlet light-emitting body, a triplet light-emitting body or a TADF material, but is not limited thereto.

[0161] In some embodiments, the thickness of the organic functional layer 130 is in the range of 10 nm to 200 nm, preferably 20 nm to 150 nm, more preferably 30 nm to 100 nm, and most preferably 40 nm to 90 nm.

[0162] The organic light-emitting device 100 of the present application can be applied to various electronic devices, including but not limited to: display devices, lighting devices, light sources, sensors, etc.

[0163] The organic compound and the organic light-emitting device of the present application are further described below in conjunction with specific embodiments.

[0164] 1. Synthesis of organic compounds

[0165] Example 1: Synthesis of Compound M1

[0166]

[0167] Synthesis of intermediate 1-3:

[0168] Intermediate 1-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-3. The molar weight of intermediate 1-3 was 9.03 mmol, and the yield was 90.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 523.

[0169] Synthesis of intermediate 1-5:

[0170] Intermediate 1-3 (10 mmol), compound 1-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-5. The molar weight of intermediate 1-5 was 8.86 mmol, and the yield was 88.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS (ASAP) = 723.

[0171] Synthesis of compound M1:

[0172] Intermediate 1-5 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound M1 with a yield of 87.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M1 was: MS (ASAP) = 765.

[0173] Example 2: Synthesis of Compound M2

[0174]

[0175] Synthesis of intermediate 2-2:

[0176] Intermediate 1-3 (10 mmol), intermediate 2-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-2. The molar weight of intermediate 2-2 was 8.37 mmol, and the yield was 83.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS (ASAP) = 723.

[0177] Synthesis of compound M2:

[0178] Intermediate 2-2 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound M2 with a yield of 89.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M2 was: MS (ASAP) = 765.

[0179] Example 3: Synthesis of Compound M3

[0180]

[0181] Synthesis of intermediate 3-2:

[0182] Intermediate 1-3 (10 mmol), compound 3-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-2. The molar weight of intermediate 3-2 was 8.59 mmol, and the yield was 85.9%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS (ASAP) = 723.

[0183] Synthesis of compound M3:

[0184] Intermediate 3-2 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound M3 with a yield of 81.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of compound M3 was: MS (ASAP) = 765.

[0185] Example 4: Synthesis of Compound M4

[0186]

[0187] Synthesis of intermediate 4-2:

[0188] Intermediate 1-3 (10 mmol), compound 4-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 4-2. The molar weight of intermediate 4-2 was 9.13 mmol, and the yield was 91.3%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 4-2 was: MS (ASAP) = 723.

[0189] Synthesis of compound M4:

[0190] Intermediate 4-2 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M4 with a yield of 85.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M4 was: MS (ASAP) = 765.

[0191] Example 5: Synthesis of Compound M5

[0192]

[0193] Synthesis of intermediate 5-2:

[0194] Intermediate 1-1 (10 mmol), compound 5-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-2. The molar weight of intermediate 5-2 was 9.23 mmol, and the yield was 92.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-2 was: MS (ASAP) = 483.

[0195] Synthesis of intermediate 5-4:

[0196] Intermediate 5-2 (10 mmol), compound 5-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-4. The molar weight of intermediate 5-4 was 8.62 mmol, and the yield was 86.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 5-4 was: MS (ASAP) = 683.

[0197] Synthesis of compound M5:

[0198] Intermediate 5-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M5 with a yield of 88.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M5 was: MS (ASAP) = 725.

[0199] Example 6: Synthesis of Compound M6

[0200]

[0201] Synthesis of intermediate 6-2:

[0202] Intermediate 5-2 (10 mmol), compound 6-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-2. The molar weight of intermediate 6-2 was 8.74 mmol, and the yield was 87.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 6-2 was: MS (ASAP) = 683.

[0203] Synthesis of compound M6:

[0204] Intermediate 6-2 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M6 with a yield of 83.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M6 was: MS (ASAP) = 725.

[0205] Example 7: Synthesis of Compound M7

[0206]

[0207] Synthesis of intermediate 7-2:

[0208] Intermediate 1-1 (10 mmol), compound 7-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-2. The molar weight of intermediate 7-2 was 9.15 mmol, and the yield was 91.5%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 7-2 was: MS (ASAP) = 483.

[0209] Synthesis of intermediate 7-4:

[0210] Intermediate 7-2 (10 mmol), compound 7-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-4. The molar weight of intermediate 7-4 was 8.29 mmol, and the yield was 82.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-4 was: MS (ASAP) = 683.

[0211] Synthesis of compound M7:

[0212] Intermediate 7-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M7 with a yield of 83.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M7 was: MS (ASAP) = 725.

[0213] Example 8: Synthesis of Compound M8

[0214]

[0215] Synthesis of intermediate 8-2:

[0216] Intermediate 1-1 (10 mmol), compound 8-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-2. The molar weight of intermediate 8-2 was 9.07 mmol, and the yield was 90.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 8-2 was: MS (ASAP) = 483.

[0217] Synthesis of intermediate 8-4:

[0218] Intermediate 8-2 (10 mmol), compound 8-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-4. The molar weight of intermediate 8-4 was 8.36 mmol, and the yield was 83.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 8-4 was: MS (ASAP) = 683.

[0219] Synthesis of compound M8:

[0220] Intermediate 8-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M8 with a yield of 81.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M8 was: MS (ASAP) = 725.

[0221] Example 9: Synthesis of Compound M9

[0222]

[0223] Synthesis of intermediate 9-2:

[0224] Intermediate 1-1 (10 mmol), compound 9-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-2. The molar weight of intermediate 9-2 was 9.21 mmol, and the yield was 92.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 9-2 was: MS (ASAP) = 513.

[0225] Synthesis of intermediate 9-4:

[0226] Intermediate 9-2 (10 mmol), compound 9-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-4. The molar weight of intermediate 9-4 was 8.71 mmol, and the yield was 87.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 9-4 was: MS (ASAP) = 713.

[0227] Synthesis of compound M9:

[0228] Intermediate 9-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M9 with a yield of 87.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M9 was: MS (ASAP) = 755.

[0229] Example 10: Synthesis of Compound M10

[0230]

[0231] Synthesis of intermediate 10-2:

[0232] Intermediate 1-1 (10 mmol), compound 10-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 10-2. The molar weight of intermediate 10-2 was 8.96 mmol, and the yield was 89.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 10-2 was: MS (ASAP) = 507.

[0233] Synthesis of intermediate 10-4:

[0234] Intermediate 10-2 (10 mmol), compound 10-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 10-4. The molar weight of intermediate 10-4 was 8.52 mmol, and the yield was 85.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 10-4 was: MS (ASAP) = 707.

[0235] Synthesis of compound M10:

[0236] Intermediate 10-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M10 with a yield of 82.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M10 was: MS (ASAP) = 749.

[0237] Example 11: Synthesis of Compound M11

[0238]

[0239] Synthesis of intermediate 11-2:

[0240] Intermediate 1-1 (10 mmol), compound 11-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 11-2. The molar weight of intermediate 11-2 was 8.73 mmol, and the yield was 87.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 11-2 was: MS (ASAP) = 407.

[0241] Synthesis of intermediate 11-3:

[0242] Intermediate 11-2 (10 mmol), compound 10-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 11-3. The molar weight of intermediate 11-3 was 8.96 mmol, and the yield was 89.6%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 11-3 was: MS (ASAP) = 607.

[0243] Synthesis of compound M11:

[0244] Intermediate 11-3 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M11 with a yield of 85.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M11 was: MS (ASAP) = 649.

[0245] Example 12: Synthesis of Compound M12

[0246]

[0247] Synthesis of intermediate 12-2:

[0248] Intermediate 1-1 (10 mmol), compound 12-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 12-2. The molar weight of intermediate 12-2 was 8.98 mmol, and the yield was 89.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 12-2 was: MS (ASAP) = 457.

[0249] Synthesis of intermediate 12-4:

[0250] Intermediate 12-2 (10 mmol), compound 12-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 12-4. The molar weight of intermediate 12-4 was 9.14 mmol, and the yield was 91.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 12-4 was: MS (ASAP) = 657.

[0251] Synthesis of compound M12:

[0252] Intermediate 12-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M12 with a yield of 82.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M12 was: MS (ASAP) = 699.

[0253] Synthesis of compound 12:

[0254] Intermediate 12-3 (10 mmol), intermediate 1-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography to obtain compound 12 with a molar weight of 7.64 mmol and a yield of 76.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of compound 12 was: MS (ASAP) = 843.

[0255] Example 13: Synthesis of Compound M13

[0256]

[0257] Synthesis of intermediate 13-2:

[0258] Intermediate 5-2 (10 mmol), compound 13-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 13-2. The molar weight of intermediate 13-2 was 8.91 mmol, and the yield was 89.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 13-2 was: MS (ASAP) = 699.

[0259] Synthesis of compound M13:

[0260] Intermediate 13-2 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M13 with a yield of 85.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M13 was: MS (ASAP) = 741.

[0261] Example 14: Synthesis of Compound M14

[0262]

[0263] Synthesis of intermediate 14-2:

[0264] Intermediate 1-1 (10 mmol), compound 14-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 14-2. The molar weight of intermediate 14-2 was 8.54 mmol, and the yield was 85.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 14-2 was: MS (ASAP) = 572.

[0265] Synthesis of intermediate 14-4:

[0266] Intermediate 14-2 (10 mmol), compound 14-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 14-4. The molar weight of intermediate 14-4 was 9.01 mmol, and the yield was 90.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 14-4 was: MS (ASAP) = 772.

[0267] Synthesis of compound M14:

[0268] Intermediate 14-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M14 with a yield of 81.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M14 was: MS (ASAP) = 814.

[0269] Example 15: Synthesis of Compound M15

[0270]

[0271] Synthesis of intermediate 15-2:

[0272] Intermediate 15-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 15-2. The molar weight of intermediate 15-2 was 9.08 mmol, and the yield was 90.8%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 15-2 was: MS (ASAP) = 635.

[0273] Synthesis of intermediate 15-3:

[0274] Intermediate 15-2 (10 mmol), compound 7-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 15-3. The molar weight of intermediate 15-3 was 8.51 mmol, and the yield was 85.1%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 15-3 was: MS (ASAP) = 835.

[0275] Synthesis of compound M15:

[0276] Intermediate 15-3 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M15 with a yield of 81.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M15 was: MS (ASAP) = 877.

[0277] Example 16: Synthesis of Compound M16

[0278]

[0279] Synthesis of intermediate 16-2:

[0280] Intermediate 1-1 (10 mmol), compound 16-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 16-2. The molar weight of intermediate 16-2 was 8.87 mmol, and the yield was 88.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-2 was: MS (ASAP) = 407.

[0281] Synthesis of intermediate 16-4:

[0282] Intermediate 16-2 (10 mmol), compound 16-3 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the mixture was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 16-4. The molar weight of intermediate 16-4 was 9.34 mmol, and the yield was 93.4%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-4 was: MS (ASAP) = 633.

[0283] Synthesis of compound M16:

[0284] Intermediate 16-4 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M16 with a yield of 85.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M16 was: MS (ASAP) = 675.

[0285] Example 17: Synthesis of Compound M17

[0286]

[0287] Synthesis of intermediate 17-2:

[0288] Intermediate 16-2 (10 mmol), compound 17-1 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 17-2. The molar weight of intermediate 17-2 was 9.02 mmol, and the yield was 90.2%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 17-2 was: MS (ASAP) = 633.

[0289] Synthesis of compound M17:

[0290] Intermediate 17-2 (10 mmol) and intermediate 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added, and stirred at 100°C for 6 h under a nitrogen atmosphere; after cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M17 with a yield of 81.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound M17 was: MS (ASAP) = 675.

[0291] Comparative Example 1: Compound Ref-1

[0292]

[0293] Comparative Example 2: Compound Ref-2

[0294]

[0295] Comparative Example 3: Compound Ref-3

[0296]

[0297] Comparative Example 4: Compound Ref-4

[0298]

[0299] 2. Energy level calculation of organic compounds

[0300] The HOMO (Highest Occupied Molecular Orbital, the highest occupied molecular orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital, the lowest unoccupied molecular orbital) energy level, T1 (first excited triplet) energy level, S1 (first excited singlet) energy level of the compounds M1 to M17 obtained in Examples 1 to 17 and the compounds Ref-1 to Ref-4 in Comparative Examples 1 to 4 can be obtained by quantum calculation. TD-DFT (time-dependent density functional theory) can be used by the method of Gaussian09W (Gaussian Inc.), and the specific simulation method can be found in WO2011141110. First, the molecular geometry was optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge0 / SpinSinglet), and then the energy structure of the organic molecule was calculated by the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / SpinSinglet). The HOMO and LUMO energy levels were calculated according to the calibration formula below, and S1, T1 and the resonance factor f(S1) were used directly.

[0301] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0302] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385;

[0303] Among them, HOMO, LUMO, T1 and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1:

[0304] Table 1 Calculation results of compound energy levels

[0305] Material HOMO[eV] LUMO[eV] <![CDATA[E T1 [eV]]> <![CDATA[E S1 [eV]]> Compound M1 -5.31 -2.31 2.65 3.22 Compound M2 -5.29 -2.26 2.69 3.21 Compound M3 -5.30 -2.21 2.68 3.28 Compound M4 -5.27 -2.27 2.68 3.28 Compound M5 -5.31 -2.27 2.68 3.29 Compound M6 -5.31 -2.29 2.67 3.21 Compound M7 -5.29 -2.31 2.65 3.29 Compound M8 -5.28 -2.32 2.61 3.21 Compound M9 -5.29 -2.31 2.61 3.21 Compound M10 -5.31 -2.31 2.61 3.24 Compound M11 -5.32 -2.27 2.67 3.26 Compound M12 -5.30 -2.27 2.67 3.22 Compound M13 -5.26 -2.31 2.62 3.25 Compound M14 -5.28 -2.32 2.61 3.21 Compound M15 -5.29 -2.31 2.62 3.26 Compound M16 -5.23 -2.31 2.61 3.22 Compound M17 -5.27 -2.29 2.59 3.23 Compound Ref-1 -5.33 -2.28 2.54 3.01 Compound Ref-2 -5.28 -2.28 2.51 3.11 Compound Ref-3 -5.26 -2.29 2.55 3.08 Compound Ref-4 -5.29 -2.27 2.58 3.05

[0306] From the data in Table 1, it can be seen that the E T1 and E S1 The energy levels are higher than those of the compounds Ref-1 to Ref-4 of Comparative Examples 1 to 4. T1 and E S1 Energy level, indicating that the organic compound of the present application is better matched with the host-guest material of the light-emitting layer, and is closer to the E T1 and E S1energy level, thereby improving the hole transport capability.

[0307] 3. Preparation and characterization of organic light-emitting devices

[0308] The structure of the organic light-emitting device prepared in this embodiment includes: a substrate, an anode, a hole injection layer (HIL), a first hole transport layer (HT-1), a second hole transport layer (HT-2), a light-emitting layer, an electron transport layer (ETL), an electron injection layer and a cathode stacked in sequence. The organic light-emitting device in this embodiment is an OLED, and the steps for preparing the organic light-emitting device are as follows:

[0309] a. Cleaning ITO (indium tin oxide) conductive glass: using a solvent (such as one or more of chloroform, acetone or isopropyl alcohol) to clean the ITO conductive glass, and then performing ultraviolet ozone plasma treatment, wherein the ITO conductive glass includes a substrate and an anode formed on the substrate;

[0310] b. Forming the organic functional layer: Move the ITO conductive glass into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6 mbar), firstly, HATCN was evaporated on the ITO conductive glass to form a 10 nm hole injection layer (HIL), then a 60 nm first hole transport layer (the material of the first hole transport layer was HT-1) and a 60 nm second hole transport layer (the material of the second hole transport layer was any one of compounds M1 to M17 or Ref-1 to Ref-4) were sequentially evaporated on the hole injection layer (HIL), then BH and BD were co-evaporated on the second hole transport layer (HT-2) in a mass ratio of 97:3 to form a 25 nm light-emitting layer, then ET and LiQ were placed in different evaporation units on the light-emitting layer, and co-deposited in a mass ratio of 50:50 to form a 30 nm electron transport layer, and then 1 nm LiQ was deposited on the electron transport layer to form an electron injection layer;

[0311] c. Forming a cathode: depositing Al on the electron injection layer to form an Al cathode with a thickness of 100 nm;

[0312] d. Packaging: The device obtained in step c is packaged with ultraviolet curing resin in a nitrogen glove box.

[0313] The above steps are used to obtain organic light-emitting devices 1 to 17 and comparative devices 1 to 4. The second hole transport layer materials used in organic light-emitting devices 1 to 17 are compounds M1 to M17, respectively, and the second hole transport layer materials used in comparative devices 1 to 4 are compounds Ref-1 to Ref-4. The other film materials of organic light-emitting devices 1 to 17 and comparative devices 1 to 4 are the same, and the preparation methods are the same.

[0314] The structures of the compounds involved in the above preparation steps are as follows:

[0315]

[0316] The organic light-emitting devices 1 to 17 and comparative devices 1 to 4 prepared as above were subjected to current-voltage (JV) characteristic tests. The current-voltage (JV) characteristics were characterized by a characterization device, and important parameters such as voltage, lifetime and external quantum efficiency were recorded. The specific data are shown in Table 2.

[0317] Table 2 Performance parameters of organic light-emitting devices

[0318]

[0319]

[0320] Table 2 is a comparison of the lifespan and external quantum efficiency of organic light emitting devices 1 to 17 and comparative devices 1 to 4, wherein the lifespan LT95 is the time when the brightness drops to 95% of the initial brightness @1000nits under constant current. Here, LT95 and external quantum efficiency are calculated relative to comparative device 1, i.e., the lifespan of comparative device 1 is 1 and the external quantum efficiency is 100%.

[0321] It can be seen from the data in Table 2 that the efficiency and lifespan of the organic light-emitting devices 1 to 17 obtained by using compounds M1 to M17 as hole transport layer materials are significantly improved compared to the efficiency and lifespan of the comparative devices 1 to 4 obtained by using compounds Ref-1 to Ref-4.

[0322] The reason why the external quantum efficiency and lifetime of organic light-emitting devices 1 to 17 are significantly higher than those of comparative devices 1 to 4 may be that in the structure of the organic compounds of the present application (such as compounds M1 to M17), the 2-spirofluorene and the fluorene-like phenyl group are simultaneously connected to the aromatic amine structure, which greatly changes the spatial structure of the molecule relative to the comparative molecule, that is, the space occupied by the molecular structure becomes larger, thereby improving the stacking of the molecules, increasing the steric hindrance, making the gaps between the molecules larger, and improving the hole mobility of the material. At the same time, the molecules have greater rigidity, the glass transition temperature of the molecules is increased, and the stability of the molecules is improved. Therefore, the efficiency, stability and lifetime of the organic light-emitting device are significantly improved.

[0323] The reason why the external quantum efficiency and lifetime of organic light-emitting devices 1 to 17 are significantly higher than those of comparative devices 2 and 3 may be that the fluorene-like phenyl group introduced into the organic compound of the present application can increase the efficiency, stability and lifetime of the device more than a single fluorene-like group. This is because the introduced fluorene-like phenyl group causes a significant change in the spatial structure of the molecule relative to the comparative molecule. A phenyl group is added to the benzene ring of the fluorene-like group in the fluorene-like phenyl group, which increases the volume of the entire molecule, increases the space occupied by the molecular structure, and increases the molecular gap, which is beneficial to hole transport, thereby improving the efficiency, stability and lifetime of the organic light-emitting device.

[0324] In summary, the performance of the organic light-emitting device prepared using the organic compound of the present application as the hole transport layer material is significantly better than the performance of the organic light-emitting device prepared using the compound of the comparative example as the hole transport layer material, and the luminous efficiency and life of the organic light-emitting device prepared using the organic compound of the present application as the hole transport layer material are significantly improved.

[0325] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0326] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. An organic compound, characterized in that The organic compound has a structure represented by formula (1): in, Ar1 is selected from any one of the following groups: X and Y are independently selected from O, S, NR3, CR4R5; R1, R2, R3, R4, R5 are independently selected from H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 20 ring atoms.

2. The organic compound according to claim 1, characterized in that The Ar1 is selected from any one of the following groups:

3. The organic compound according to claim 1, characterized in that R1 and R2 are independently selected from H or tert-butyl.

4. The organic compound according to claim 1, characterized in that R3, R4, and R5 are independently selected from methyl or phenyl.

5. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of formula (1-1) to formula (1-4):

6. The organic compound according to any one of claims 1 to 5, characterized in that The organic compound is selected from the compounds represented by the following structures:

7. A mixture, characterized in that The mixture comprises at least one organic compound as described in any one of claims 1 to 6 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, organic host materials and inorganic quantum dot materials.

8. A composition, characterized in that The composition comprises at least one organic compound according to any one of claims 1 to 6 and at least one organic solvent, or the composition comprises the mixture according to claim 7 and at least one organic solvent.

9. The composition according to claim 8, characterized in that The mass percentage of the organic compound in the composition is 0.01 wt % to 10 wt %, or the mass percentage of the mixture in the composition is 0.01 wt % to 10 wt %.

10. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; The material of the organic functional layer includes at least one organic compound according to any one of claims 1 to 6, or the material of the organic functional layer includes the mixture according to claim 7.

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