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 (I): # imgabs0. The organic compound provided by the invention connects a benzfluorene group with a diarylamine group; wherein Ar1 represents a naphthobenzofuran-like group, a naphthobenzothiophene-like group, a benzocarbazole-like group or a benzfluorene-like group, the structure effectively improves the accumulation of molecules, so that the molecules of the organic compound have higher rigidity, the glass transition temperature of the organic compound is further improved, the organic compound is used for preparing an organic light-emitting device, and the organic light-emitting device has a good application prospect. The luminous efficiency and the service life of the organic light-emitting device can be effectively improved.

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 semiconductor materials have diversity in synthesis, relatively low manufacturing costs, and excellent optical and electrical properties. Therefore, organic light-emitting diodes (OLEDs) have great potential for application in optoelectronic devices (such as flat panel displays and lighting).

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices that use organic electroluminescence usually have an anode, a cathode, and an organic functional layer located between the two. In order to improve the efficiency and life of organic light-emitting 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 light-emitting 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. When the excitons transition back to the ground state, light is emitted, thereby realizing the light emission of the organic light-emitting device. Organic light-emitting devices have the characteristics of autonomous luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response, and therefore have broad application prospects.

[0004] In order to make efficient organic light-emitting devices, in addition to developing high-performance light-emitting materials, the development of transport materials is also very important. At present, most transport materials are small molecule materials based on carbazole derivatives. Such materials have the disadvantage of unbalanced hole and electron transport, which results in a short life of organic light-emitting devices using such organic compounds. Summary of the invention

[0005] The present application provides an organic compound, a mixture, a composition and an organic light-emitting device to improve the luminous efficiency and life of the organic light-emitting device.

[0006] The present application provides an organic compound having a structure shown in formula (I):

[0007]

[0008] in,

[0009] Ar 1 Select one of the following structures:

[0010]

[0011] X is selected from O, S, NR 1 , CR 2 R 3 ;

[0012] R 1 , R 2 , R 3 is selected from D, H, substituted or unsubstituted alkyl having 1 to 20 C atoms, substituted or unsubstituted branched alkyl having 3 to 20 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0013] Ar 2 It is selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0014] In some embodiments, X is selected from O or S.

[0015] In some embodiments, Ar 2 Any one selected from the following groups:

[0016]

[0017] in,

[0018] Y is selected from O, S, NR 4 , CR 5 R 6 ;

[0019] R 4 , R 5 , R 6 is selected from D, H, substituted or unsubstituted alkyl having 1 to 20 C atoms, substituted or unsubstituted branched alkyl having 3 to 20 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0020] * indicates the attachment site.

[0021] In some embodiments, Ar 2 Any one selected from the following groups:

[0022]

[0023] Wherein, * indicates the connection site.

[0024] In some embodiments, the organic compound is selected from any one of the following structures:

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032] The present application also provides a mixture, which includes at least one organic functional material and at least one organic compound as described above, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials and inorganic quantum dot materials.

[0033] The present application also provides a composition, which comprises at least one organic solvent and at least one organic compound as described above, or the composition comprises at least one organic solvent and a mixture as described above.

[0034] In some embodiments, in the composition, the mass percentage content of the organic compound or the mixture ranges from 0.01 wt % to 10 wt %.

[0035] The present application also provides an organic light-emitting device, the organic light-emitting device comprising:

[0036] a first electrode;

[0037] a second electrode, disposed opposite to the first electrode; and

[0038] an organic functional layer, located between the first electrode and the second electrode;

[0039] 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, or the material of the organic functional layer includes the combination as described above.

[0040] In some embodiments, the organic functional layer includes a light-emitting layer and a hole transport layer, the hole transport layer is located between the light-emitting layer and the first electrode, or the hole transport layer is located between the light-emitting layer and the second electrode;

[0041] The hole transport layer includes a hole transport material, and the hole transport material includes at least one of the organic compounds.

[0042] The present application provides an organic compound, a mixture, a composition and an organic light-emitting device. The organic compound provided by the present application connects a benzofluorene group with a diarylamine group, wherein Ar 1 represents a naphthobenzofuran-like group, a naphthobenzothiophene-like group, a benzocarbazole group or a benzofluorene group. In the present application, an aromatic amine is used to convert a benzofluorene group and an Ar representing a naphthobenzofuran-like group, a naphthobenzothiophene-like group, a benzocarbazole group or a benzofluorene group into 1 The groups are connected to expand the conjugated system of the entire molecule. This structure effectively improves the stacking of molecules, makes the organic compound molecules more rigid, and increases the glass transition temperature of the organic compound. The organic light-emitting device prepared with this organic compound can effectively improve the luminous efficiency and life of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] Figure 1 A schematic diagram of the structure of an organic light-emitting device provided in an embodiment of the present application;

[0044] Figure 2 A schematic diagram of the structure of another organic light-emitting device provided in an embodiment of the present application.

[0045] Explanation of the accompanying drawings: organic light-emitting device-100, substrate-101, first electrode-110, organic functional layer-130, light-emitting layer-131, hole injection layer-132, hole transport layer-133, first hole transport layer-1331, second hole transport layer-1332, electron blocking layer-134, electron transport layer-135, electron injection layer-136, second electrode-120. DETAILED DESCRIPTION

[0046] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application. In addition, it should be understood that the specific implementation methods 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, in the absence of any contrary instructions, the directional words such as "upper" and "lower" used 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", "optional" means optional, that is, it refers to any one of the two parallel schemes 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 application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions of the listed features.

[0047] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0048] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. 1 , then R 1 Can be independently selected from different groups.

[0049] In the present 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 the defined group may be substituted by one or more substituents R, wherein R is selected from 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 or a combination of the above groups.

[0050] 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.

[0051] 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, each occurrence of which can be independently C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9 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.

[0052] 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: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, 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.

[0053] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom may be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to In: triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthyridine, quinoxaline, phenanthridine, primary dine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and derivatives thereof.

[0054] In this application, "amino" refers to an amine derivative having the formula -N(X) 2 The structural features of wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amine groups include -NH 2 、-N(alkyl) 2 、-NH(alkyl), -N(cycloalkyl) 2 、-NH(cycloalkyl), -N(heterocyclic) 2 、-NH(heterocyclic group), -N(aryl group)2 , -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.

[0055] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0056] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site.

[0057] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in adjacent positions in the group are fusion sites.

[0058] 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; express Fused with any adjacent C atom on benzene.

[0059] The present application provides an organic compound having a structure shown in general formula (I):

[0060]

[0061] in,

[0062] Ar 1 Select one of the following structures:

[0063]

[0064] X is selected from O, S, NR 1 , CR 2 R 3 ;

[0065] R 1 , R 2 , R 3 is selected from D, H, substituted or unsubstituted alkyl having 1 to 20 C atoms, substituted or unsubstituted branched alkyl having 3 to 20 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0066] Ar 2It is selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

[0067] The organic compound provided by the present application connects a benzofluorene group with a diarylamine group, wherein Ar 1 represents a naphthobenzofuran-like group, a naphthobenzothiophene-like group, a benzocarbazole group or a benzofluorene group. Among them, the benzofluorene group and the naphthobenzofuran-like group, the naphthobenzothiophene-like group, the benzocarbazole group or the benzofluorene group all have a large conjugated planar structure, and the diarylamine is used as a connecting group, and its structure contains a nitrogen atom. The lone pair of electrons on the nitrogen atom can participate in conjugation, thereby increasing the stability of the entire molecule. In this application, the benzofluorene group and the Ar representing the naphthobenzofuran-like group, the naphthobenzothiophene group, the benzocarbazole group or the benzofluorene group are connected by aromatic amine. 1 The groups are connected to expand the conjugated system of the entire molecule, allowing the molecules to be arranged more closely and orderly, thereby effectively improving the stacking of the molecules. At the same time, it makes the organic compound molecules more rigid, increases the glass transition temperature of the organic compound, and makes the organic compound have higher stability.

[0068] In the present application, when the organic compound is used as an organic functional material in an organic light-emitting device, especially as a hole transport material, the above-mentioned structure of the organic compound enables it to have better charge transfer balance performance and higher stability, and can improve the problem of hole and electron transfer imbalance existing in traditional transport materials, thereby effectively improving the luminous efficiency and life of the organic light-emitting device.

[0069] In some embodiments, R 1 , R 2 , R 3 is selected from D, H, a substituted or unsubstituted alkyl group having 1 to 15 C atoms, a substituted or unsubstituted branched alkyl group having 3 to 15 C atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 C atoms, a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0070] In some embodiments, R 1 , R 2 , R 3is selected from D, H, substituted or unsubstituted alkyl having 1 to 10 C atoms, substituted or unsubstituted branched alkyl having 3 to 10 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 10 C atoms, substituted or unsubstituted aromatic group having 5 to 20 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0071] In some embodiments, X is selected from O or S.

[0072] In some embodiments, Ar 1 Select one of the following structures:

[0073]

[0074]

[0075] Wherein, * indicates the connection site.

[0076] In some embodiments, Ar 2 Any one selected from the following groups:

[0077]

[0078] in,

[0079] Y is selected from O, S, NR 4 , CR 5 R 6 ;

[0080] R 4 , R 5 , R 6 is selected from D, H, substituted or unsubstituted alkyl having 1 to 20 C atoms, substituted or unsubstituted branched alkyl having 3 to 20 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0081] * indicates the attachment site.

[0082] In some embodiments, R 4 , R 5 , R 6is selected from D, H, substituted or unsubstituted alkyl having 1 to 10 C atoms, substituted or unsubstituted branched alkyl having 3 to 10 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 10 C atoms, substituted or unsubstituted aromatic group having 5 to 20 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0083] In some embodiments, Ar 2 Any one selected from the following groups:

[0084]

[0085] Wherein, * indicates the connection site.

[0086] In some embodiments, the organic compound is selected from but not limited to any one of the following structures:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] The hydrogen atoms on any group in the above structure may be substituted or unsubstituted. When the hydrogen atoms on any group in the above structure are substituted, the hydrogen atoms on any group in the above structure may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group, halogen atom, 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 or a combination of the above groups.

[0094] In some embodiments, the organic compound can be used as an organic functional material in an organic light-emitting device. The organic functional material can be a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a guest emitter, or a host emitter. Among them, the host emitter can be a phosphorescent host material, a fluorescent host material, or a thermally activated delayed fluorescence luminescent material (TADF).

[0095] In some embodiments, the organic compound can be used as a hole transport material in an OLED organic light emitting device.

[0096] 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. The organic compound has a higher glass transition temperature and thus has better stability, which can improve the stability of the organic functional material, thereby improving the stability, luminous efficiency and life of the organic light-emitting device.

[0097] The present application also provides a mixture, the mixture includes at least one organic functional material and at least one organic compound as described above, the organic functional material is selected from hole injection material (HIM), hole transport material (HTM), electron transport material (ETM), electron injection material (EIM), electron blocking material (EBM), hole blocking material (HBM), luminescent guest material (Guest Emitter), luminescent host material (Host Emitter) and inorganic quantum dot material. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated into the present application as a reference.

[0098] In some embodiments, the organic functional material includes small molecule compounds and / or polymers.

[0099] In some embodiments, the organic compound can be used as an organic functional material for an evaporation-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.

[0100] In some embodiments, the organic compound can be used as an organic functional material for a printed OLED, and the molecular weight of the organic compound is ≥700 g / mol, preferably ≥900 g / mol, more preferably ≥1000 g / mol, and most preferably ≥1100 g / mol.

[0101] The present application also provides a composition, which comprises at least one organic solvent and at least one organic compound as described above, or the composition comprises at least one organic solvent and a mixture as described above.

[0102] In some embodiments, the organic solvent is selected from one of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic compound, boric ester or phosphate ester compounds, or a mixture of two or more solvents.

[0103] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0104] Organic solvents based on 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- Isopropylbiphenyl, 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.

[0105] Organic solvents based on aromatic ketone 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.

[0106] Organic solvents based on aromatic ether 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 acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0107] Organic solvents based on aliphatic ketones or aliphatic ethers 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, 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, and the like.

[0108] Ester-based organic solvents include, but are not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkanolide, alkyl oleate, etc. Methyl benzoate, octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0109] It should be noted that the organic solvent may be used alone or as a mixture of two or more organic solvents.

[0110] In some embodiments, the composition further comprises at least one co-solvent. The co-solvent 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.

[0111] In some embodiments, the organic solvent is a solvent having a Hansen solubility parameter within the following range:

[0112] δd (dispersion force) at 17.0MPa 1 / 2 ~23.2MPa 1 / 2 range, especially at 18.5MPa 1 / 2 ~21.0MPa 1 / 2 scope;

[0113] δp (polar force) at 0.2MPa 1 / 2 ~12.5MPa 1 / 2 range, especially at 2.0MPa 1 / 2 ~6.0MPa 1 / 2 scope;

[0114] δh (hydrogen bond force) at 0.9MPa 1 / 2 ~14.2MPa 1 / 2 range, especially at 2.0MPa 1 / 2 ~6.0MPa 1 / 2 range.

[0115] In the present application, the boiling point parameter of the organic solvent should be considered when selecting it.

[0116] In some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; further preferably ≥250°C; more preferably ≥275°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. Finally, the organic solvent can be evaporated from the solvent system to form a film containing an organic functional material.

[0117] In some embodiments, the composition can be a solution.

[0118] In some embodiments, the composition may be a suspension.

[0119] 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 15 wt %, more preferably 0.2 wt % to 5 wt %, and most preferably 0.25 wt % to 3 wt %.

[0120] In the present application, the composition can be used as a coating or printing ink for preparing an organic light-emitting device, and the organic light-emitting device is preferably prepared by a printing or coating preparation method.

[0121] Among them, suitable printing or coating techniques include, but are not limited to: inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing, pad printing, or slot extrusion coating, etc. Gravure printing, nozzle printing and inkjet printing techniques are preferred.

[0122] When the composition is a solution or a suspension, the composition may further include one or more other components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., which are used to adjust viscosity, film-forming properties, improve adhesion, etc.

[0123] For the printing technology and its related requirements for the related solutions, such as solvent, concentration, viscosity, etc., reference may be made to the prior art and no limitation is imposed here.

[0124] In the present application, the organic compound, the mixture and the composition can be used for preparing an organic light-emitting device.

[0125] Please refer to Figure 1 The present application also provides an organic light-emitting device 100, which includes a first electrode 110, a second electrode 120, and an organic functional layer 130. The second electrode 120 is arranged opposite to the first electrode 110, and the organic functional layer 130 is located between the first electrode 110 and the second electrode 120; wherein 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 the mixture as described above, or the material of the organic functional layer 130 includes the combination as described above.

[0126] In the present application, the organic light-emitting device may be, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode), etc. OLED, OLEEC, and OLEFET are preferred.

[0127] In some embodiments, the first electrode 110 may be an anode, and the second electrode 120 may be a cathode, but is not limited thereto.

[0128] In some embodiments, please refer to Figure 1 The organic functional layer 130 at least includes a light emitting layer 131 and a hole transport layer 133. The hole transport layer 133 may include one or more film layers. The hole transport layer 133 includes at least one organic compound.

[0129] In some embodiments, the light-emitting layer includes a singlet light emitter, a triplet light emitter, or TADF.

[0130] In some embodiments, please refer to Figure 1 The organic functional layer 130 further includes at least one of a hole injection layer 132 , an electron blocking layer 134 , an electron transport layer 135 , an electron injection layer 136 , a hole blocking layer, and the like.

[0131] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer, 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 organic light-emitting devices according to the present application.

[0132] In some embodiments, the cathode is an electrode that injects 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 light-emitting material in the light-emitting layer, or the n-type semiconductor material serving 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 application, and the materials of the cathode include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / at least one of Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the cathode 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.

[0133] In some embodiments, the hole injection layer is used to promote the injection of holes from the anode to the light-emitting layer, and the hole injection layer includes a hole injection material, which is a material that can receive holes injected from the anode 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 organic functional material of the film layer into which the holes are injected away from the anode side (such as: the hole transport material of the hole transport layer). The hole injection material includes but is not limited to at least one of 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.

[0134] In some embodiments, the hole transport layer can be used to transport holes to the light-emitting layer, and the hole transport layer includes a hole transport material, and the hole transport material 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.

[0135] In some embodiments, the electron transport layer is used to transport electrons, and the electron transport layer includes an electron transport material, which receives electrons injected from the cathode and transfers the electrons to the light-emitting layer. 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.

[0136] In some embodiments, the electron injection layer is used to inject electrons, and the electron injection layer 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 cathode, and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, and has the ability to prevent the excitons generated by the light-emitting layer 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 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. At least one.

[0137] In some embodiments, the hole blocking layer is used to block holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0138] For details, please refer to Figure 1 The organic light-emitting device 100 also includes a substrate 101, and the first electrode 110, the hole injection layer 132, the hole transport layer 133, the electron blocking layer 134, the light-emitting layer 131, the electron transport layer 135, the electron transport layer 135, the electron injection layer 136 and the second electrode 120 are stacked in sequence on the substrate 101 along the thickness direction of the substrate 101.

[0139] The substrate 101 may be a transparent substrate or an opaque substrate. The substrate 101 may be a rigid substrate or an elastic flexible substrate. The material of the substrate 101 may include but is not limited to plastic, polymer, metal, semiconductor wafer or glass, etc., which is not limited here.

[0140] In some embodiments, the thickness of the organic functional layer ranges from 10 nm to 200 nm, preferably from 20 nm to 150 nm, more preferably from 30 nm to 100 nm, and even more preferably from 40 nm to 90 nm.

[0141] In some embodiments, the organic light-emitting device can be applied to a variety of electronic devices, including but not limited to display panels, lighting devices, light sources, sensors, etc.

[0142] The present application also provides a method for preparing the organic compound described in the above embodiments, and illustratively provides Embodiments 1 to 13 to describe the method for preparing the organic compound in detail.

[0143] Example 1

[0144] Synthesis of organic compound C-1

[0145] The synthetic route of organic compound C-1 is as follows:

[0146]

[0147] The specific synthesis steps of organic compound C-1 are as follows:

[0148] Synthesis of intermediate 1-3: Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd (dba) 2(0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. The organic phase column chromatography obtained intermediate 1-3, the molar weight of intermediate 1-3 was 8.85mmol, and the yield was 88.5%. Atmospheric pressure solid phase analysis probe mass spectrometry results of intermediate 1-3: MS (ASAP) = 335;

[0149] Synthesis of organic compound C-1: Compound 1-3 (10 mmol), compound 1-4 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-1 with a yield of 86.2%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-1: MS (ASAP) = 551.

[0150] Example 2

[0151] Synthesis of organic compound C-2

[0152] The synthetic route of organic compound C-2 is as follows:

[0153]

[0154] The specific synthesis steps of organic compound C-2 are as follows:

[0155] Compound 1-3 (10 mmol), compound 2-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-2 with a yield of 89.3%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-2: MS (ASAP) = 551.

[0156] Example 3

[0157] Synthesis of organic compound C-3

[0158] The synthetic route of organic compound C-3 is as follows:

[0159]

[0160] The specific synthesis steps of organic compound C-3 are as follows:

[0161] Compound 1-3 (10 mmol), compound 3-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-3 with a yield of 82.6%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-3: MS (ASAP) = 551.

[0162] Example 4

[0163] Synthesis of Organic Compound C-4

[0164] The synthetic route of organic compound C-4 is as follows:

[0165]

[0166] The specific synthesis steps of organic compound C-4 are as follows:

[0167] Compound 1-3 (10 mmol), compound 4-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-4 with a yield of 84.4%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-4: MS (ASAP) = 551.

[0168] Example 5

[0169] Synthesis of organic compound C-5

[0170] The synthetic route of organic compound C-5 is as follows:

[0171]

[0172] The specific synthesis steps of organic compound C-5 are as follows:

[0173] Compound 1-3 (10 mmol), compound 5-1 (10 mmol), Pd (dba) 2(0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-5 with a yield of 79.3%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-5: MS (ASAP) = 551.

[0174] Example 6

[0175] Synthesis of Organic Compound C-6

[0176] The synthetic route of organic compound C-6 is as follows:

[0177]

[0178] The specific synthesis steps of organic compound C-6 are as follows:

[0179] Synthesis of intermediate 6-3: Compound 6-1 (10 mmol), compound 6-2 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. The organic phase was column chromatographed to obtain intermediate 6-3. The molar weight of intermediate 6-3 was 7.56mmol, and the yield was 75.6%. Atmospheric pressure solid phase analysis probe mass spectrometry results of intermediate 6-3: MS (ASAP) = 411;

[0180] Synthesis of organic compound C-6: Compound 6-3 (10 mmol), compound 4-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-6 with a yield of 83.7%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-6: MS (ASAP) = 627.

[0181] Example 7

[0182] Synthesis of Organic Compound C-7

[0183] The synthetic route of organic compound C-7 is as follows:

[0184]

[0185] The specific synthesis steps of organic compound C-7 are as follows:

[0186] Synthesis of intermediate 7-2: Compound 6-1 (10 mmol), compound 7-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. The organic phase was column chromatographed to obtain intermediate 7-2. The molar weight of intermediate 7-2 was 8.19mmol and the yield was 81.9%. Atmospheric pressure solid phase analysis probe mass spectrometry results of intermediate 7-2: MS (ASAP) = 411;

[0187] Synthesis of organic compound C-7: Compound 7-2 (10 mmol), compound 7-3 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-7 with a yield of 86.3%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-7: MS (ASAP) = 627.

[0188] Example 8

[0189] Synthesis of Organic Compound C-8

[0190] The synthetic route of organic compound C-8 is as follows:

[0191]

[0192] The specific synthesis steps of organic compound C-8 are as follows:

[0193] Compound 7-2 (10 mmol), compound 8-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-8 with a yield of 82.8%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-8: MS (ASAP) = 627.

[0194] Example 9

[0195] Synthesis of Organic Compound C-9

[0196] The synthetic route of organic compound C-9 is as follows:

[0197]

[0198] The specific synthesis steps of organic compound C-9 are as follows:

[0199] Compound 7-2 (10 mmol), compound 9-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-9 with a yield of 91.3%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-9: MS (ASAP) = 627.

[0200] Example 10

[0201] Synthesis of Organic Compound C-10

[0202] The synthetic route of organic compound C-10 is as follows:

[0203]

[0204] The specific synthesis steps of organic compound C-10 are as follows:

[0205] Synthesis of intermediate 10-3: Compound 10-1 (10 mmol), compound 10-2 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. The organic phase was column chromatographed to obtain intermediate 10-3. The molar weight of intermediate 10-3 was 8.69mmol, and the yield was 86.9%. Atmospheric pressure solid phase analysis probe mass spectrometry results of intermediate 10-3: MS (ASAP) = 451;

[0206] Synthesis of organic compound C-10: Compound 10-3 (10 mmol), compound 8-1 (10 mmol), Pd (dba) 2(0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-10 with a yield of 74.3%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-7: MS (ASAP) = 667.

[0207] Embodiment 11

[0208] Synthesis of Organic Compound C-11

[0209] The synthetic route of organic compound C-11 is as follows:

[0210]

[0211] The specific synthesis steps of organic compound C-11 are as follows:

[0212] Compound 10-3 (10 mmol), compound 2-1 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-11 with a yield of 84.6%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-11: MS (ASAP) = 667.

[0213] Example 12

[0214] Synthesis of Organic Compound C-12

[0215] The synthetic route of organic compound C-12 is as follows:

[0216]

[0217] The specific synthesis steps of organic compound C-12 are as follows:

[0218] Synthesis of intermediate 12-1: Compound 1-1 (10 mmol), compound 7-1 (10 mmol), Pd (dba) 2(0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. The organic phase was column chromatographed to obtain intermediate 12-1. The molar weight of intermediate 12-1 was 8.73mmol, and the yield was 87.3%. Atmospheric pressure solid phase analysis probe mass spectrometry results of intermediate 12-1: MS (ASAP) = 335;

[0219] Synthesis of organic compound C-12: Compound 12-1 (10 mmol), compound 12-2 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-12 with a yield of 76.9%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-12: MS (ASAP) = 567.

[0220] Example 13

[0221] Synthesis of Organic Compound C-13

[0222] The synthetic route of organic compound C-13 is as follows:

[0223]

[0224] The specific synthesis steps of organic compound C-13 are as follows:

[0225] Compound 12-1 (10 mmol), compound 1-2 (10 mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100°C for 6h in a nitrogen atmosphere. After cooling, the reaction solution was rotary evaporated to remove the solvent, and then extracted and washed with water to separate the liquid. Organic phase column chromatography was performed to obtain organic compound C-13 with a yield of 78.6%. Atmospheric pressure solid phase analysis probe mass spectrometry results of organic compound C-13: MS (ASAP) = 577.

[0226] Comparative Example

[0227] The structure of organic compound Ref-1:

[0228]

[0229] The HOMO (Highest Occupied Molecular Orbital) energy level, LUMO (Lowest Unoccupied Molecular Orbital) energy level, T 1 (first excited triplet state) energy level, S 1 (First excited singlet) energy level. Specifically, TD-DFT (time-dependent density functional theory) was used through 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" (Charge 0 / Spin Singlet). 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" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO energy level and the LUMO energy level were calculated according to the following calibration formula: S 1 Energy level, T 1 Energy levels and resonance factor f(S 1 ) is used directly.

[0230] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0231] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0232] Among them, HOMO (G) and LUMO (G) are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1:

[0233] Table 1 Energy level data table

[0234] Compound HOMO[eV] LUMO[eV] <![CDATA[E T1 [eV]]> <![CDATA[E S1 [eV]]> Example 1 C-1 -5.36 -2.49 2.31 3.18 Example 2 C-2 -5.38 -2.46 2.33 3.19 Example 3 C-3 -5.33 -2.43 2.39 3.18 Example 4 C-4 -5.33 -2.43 2.39 3.13 Example 5 C-5 -5.36 -2.41 2.31 3.15 Example 6 C-6 -5.35 -2.51 2.31 3.16 Example 7 C-7 -5.38 -2.50 2.38 3.19 Example 8 C-8 -5.37 -2.48 2.36 3.11 Example 9 C-9 -5.31 -2.49 2.39 3.13 Example 10 C-10 -5.31 -2.48 2.38 3.09 Embodiment 11 C-11 -5.38 -2.49 2.39 3.09 Example 12 C-12 -5.30 -2.48 2.38 3.12 Example 13 C-13 -5.30 -2.47 2.39 3.11 Comparative Example Ref-1 -5.48 -2.41 2.43 2.91

[0235] From the results in Table 1, it can be seen that the E of organic compounds C-1 to C-13 provided in Examples 1 to 13 of the present application is T1 The energy level is smaller than that of the comparative compound Ref-1. T1 Energy level, E of organic compound C-1 to organic compound C-13 S1The energy level is higher than that of the comparative compound Ref-1. S1 Energy level, indicating the E of the organic compound of this application T1 Energy Level and E S1 The difference between the energy level and the light-emitting guest material becomes larger, which makes the hole transport ability stronger, thereby improving the luminous efficiency and life of the organic light-emitting device.

[0236] The present application also provides exemplary manufacturing steps of the organic light-emitting device described in the above embodiments, as shown below.

[0237] Please refer to Figure 2 The organic light-emitting device of this embodiment includes: a substrate 101, a first electrode 110 (anode), a hole injection layer 132, a hole transport layer 133, a light-emitting layer 131, an electron transport layer 135, an electron injection layer 136 and a second electrode 120 (cathode) stacked in sequence. Among them, the material of the substrate 101 is glass; the material of the first electrode 110 is ITO; the material of the hole injection layer 132 is HATCN; the hole transport layer 133 includes a first hole transport layer 1331 and a second hole transport layer 1332, the material of the first hole transport layer 1331 is HT-1, and the material of the second hole transport layer 1332HT-2 is (HT-2 is selected from one of the organic compounds C-1 to C-13); the material of the light-emitting layer 131 is BH and BD; the material of the electron transport layer 135 is ET and LiQ; the material of the electron injection layer 136 is LiQ; the material of the second electrode 120 is Al. Specifically, the preparation steps of the organic light-emitting device are as follows:

[0238] a. Cleaning of the conductive glass substrate: First, the conductive glass substrate is cleaned with a solvent, and then subjected to ultraviolet ozone plasma treatment, wherein the conductive glass substrate includes a substrate 101 and a first electrode 110 formed on the substrate 101, and the solvent includes deionized chloroform, ketone, isopropyl alcohol, etc.

[0239] b. Formation of organic functional layer: The conductive glass substrate treated in step a is moved into a vacuum vapor deposition device and heated in a high vacuum (1×10 -6Under the condition of 1000 mbar, a hole injection material HATCN is evaporated on the first electrode 110 by resistive heating evaporation to form a hole injection layer 132 with a thickness of 10 nm; a hole transport material HT-1 is evaporated on the hole injection layer 132 to form a first hole transport layer 1331 with a thickness of 60 nm, and a hole transport material HT-2 is evaporated on the first hole transport layer 1331 to form a second hole transport layer 1332 with a thickness of 60 nm, wherein the first hole transport layer 1331 and the second hole transport layer 1332 together constitute the hole transport layer 133 ; An organic light-emitting material is evaporated on the hole transport layer 133, wherein the organic light-emitting material includes a main material BH and a doping material BD, and the weight ratio of BD to BH is 97:3, to form a light-emitting layer 131 with a thickness of 25nm; electron transport materials ET and Liq are evaporated on the light-emitting layer 131, ET and Liq are placed in different evaporation units and co-deposited in a weight ratio of 50:50 to form an electron transport layer 135 with a thickness of 30nm; electron injection material Liq is evaporated on the electron transport layer 135 to form an electron injection layer 136 with a thickness of 1nm.

[0240] c. Formation of cathode: Al is evaporated on the electron injection layer 136 by vacuum evaporation to form the second electrode 120 with a thickness of 100 nm.

[0241] d. Packaging: The device obtained in step c is packaged with ultraviolet curing resin in a nitrogen glove box.

[0242] Through the above steps, organic compounds C-1 to C-13 of the present application are used as hole transport materials HT-2 to form organic light-emitting devices 1 to 13, respectively, and organic compound Ref-1 is used as hole transport material HT-2 to form comparative device 1. Only the hole transport material HT-2 used in organic light-emitting devices 1 to 13 and comparative device 1 is different, and other materials and preparation steps used in organic light-emitting devices 1 to 13 and comparative device 1 are the same.

[0243] The structural formulas of other materials involved in the organic functional layer in the above steps are as follows:

[0244]

[0245] The current-voltage (JV) characteristics of organic light-emitting devices 1 to 13 and comparative device 1 were tested using a characterization device, and the voltage, life parameters and external quantum efficiency of the organic light-emitting devices were recorded at the same time, as shown in Table 2 for details.

[0246] Table 2 Performance data of organic light emitting devices 1 to 13 and comparative device 1

[0247]

[0248]

[0249] The lifetime LT95 in Table 2 is the time when the brightness drops to 95% of the initial brightness @1000nits under constant current. The LT95 and external quantum efficiency in Table 2 are calculated relative to the comparative device 1, that is, the lifetime of the comparative device 1 is 1 and the external quantum efficiency is 100%.

[0250] It can be seen from the data in Table 1 that the voltage of organic light-emitting devices 1 to 13 is lower than that of comparative device 1, and the lifespan LT95 and external quantum efficiency of organic light-emitting devices 1 to 13 are significantly improved compared with comparative device 1, indicating that using the organic compound of the present application as the material of the hole transport layer can effectively improve the luminous efficiency and luminous life of the organic light-emitting device.

[0251] The reason is that the organic compound provided in the present application connects the benzofluorene group with the diarylamine group, and the benzofluorene group and the Ar representing the naphthobenzofuran group, the naphthobenzothiophene group, the benzocarbazole group or the benzofluorene group are connected by the aromatic amine. 1 The groups are connected to expand the conjugated system of the entire molecule, so that the molecules can be arranged more closely and orderly, thereby effectively improving the stacking of the molecules, and at the same time making the organic compound molecules more rigid, increasing the glass transition temperature of the organic compound, and making the organic compound have higher stability. When the organic compound is used as an organic functional material in an organic light-emitting device, especially as a hole transport material, the above structure of the organic compound enables it to have better charge transfer balance performance and higher stability. Therefore, the organic compound of the present application can effectively improve the luminous efficiency and life of the organic light-emitting device.

[0252] 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.

[0253] The above-mentioned embodiments only express several implementation methods of the present application, 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 a person of ordinary skill in the art, several variations and improvements can be made without departing from the concept of the present application, and these all belong to the protection scope of the present application. Therefore, the protection scope of the patent of the present application shall be subject to the attached claims.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in general formula (I): in, Ar1 is selected from one of the following structures: X is selected from O, S, NR1, CR2R3; R1, R2, R3 are selected from D, H, substituted or unsubstituted alkyl having 1 to 20 C atoms, substituted or unsubstituted branched alkyl having 3 to 20 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms; Ar2 is selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of these groups.

2. The organic compound according to claim 1, characterized in that X is selected from O or S.

3. The organic compound according to claim 1, characterized in that Ar2 is selected from any one of the following groups: in, Y is selected from O, S, NR4, CR5R6; R4, R5, R6 are selected from D, H, substituted or unsubstituted alkyl having 1 to 20 C atoms, substituted or unsubstituted branched alkyl having 3 to 20 C atoms, substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms; * indicates the attachment site.

4. The organic compound according to claim 3, characterized in that Ar2 is selected from any one of the following groups: Wherein, * indicates the connection site.

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

6. A mixture, characterized in that The mixture comprises at least one organic functional material and at least one organic compound as described in any one of claims 1 to 5, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials and inorganic quantum dot materials.

7. A composition, characterized in that The composition comprises at least one organic solvent and at least one organic compound according to any one of claims 1 to 5, or the composition comprises at least one organic solvent and a mixture according to claim 6.

8. The composition according to claim 7, characterized in that In the composition, the mass percentage content of the organic compound or the mixture ranges from 0.01 wt % to 10 wt %.

9. 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 as described in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture as described in claim 6, or the material of the organic functional layer includes the composition as described in claim 7 or 8.

10. The organic light emitting device according to claim 9, characterized in that: The organic functional layer includes a light-emitting layer and a hole transport layer, wherein the hole transport layer is located between the light-emitting layer and the first electrode, or the hole transport layer is located between the light-emitting layer and the second electrode; The hole transport layer includes a hole transport material, and the hole transport material includes at least one of the organic compounds.

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