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

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The chemical structural formula of the organic compound is as shown in a formula M: # imgabs0 #. The organic compound has good performance of carrier transport and charge balance adjustment and has high thermal stability. The compound can be applied to an organic light-emitting device as a light-emitting auxiliary material, and can be applied to the organic light-emitting device as a light-emitting auxiliary material for reducing the working voltage, improving the light-emitting efficiency and prolonging the service life.

Description

Technical Field

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

[0002] At present, organic electroluminescent elements generally include an anode, a cathode, and an organic functional layer located between the two, and use the organic material of the organic layer to convert electrical energy into light energy, thereby realizing organic electroluminescence. In order to improve the luminous efficiency and service life of the organic electroluminescent element, the organic functional layer often includes a multilayer structure, and the organic matter of each layer is different. Specifically, the organic functional layer generally includes but is not limited to a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. When the organic electroluminescent element is working, by applying voltage to the anode and the cathode, holes are injected from the anode to the organic functional layer, and electrons are injected from the cathode to the organic functional layer. The injected holes meet with the electrons to form excitons, and the excitons emit light when they return to the ground state through radiation transition, thereby realizing the luminescence of the organic electroluminescent element. With the characteristics of self-luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response, the organic electroluminescent element has a wide range of application prospects and broad development potential.

[0003] In order to improve the luminous efficiency of organic electroluminescent elements and extend the service life of the elements, the development and matching of luminescent auxiliary layer materials are crucial. By adopting luminescent auxiliary materials with suitable transmission capabilities, organic electroluminescent devices can achieve a balance in carrier transmission, block reverse electron migration, and allow electrons and holes to recombine in the central area of ​​the luminescent layer, thereby reducing the quenching of excitons, effectively improving the luminous efficiency and extending the service life of the device. How to design new luminescent auxiliary materials with better performance to adjust the balance of hole and electron transmission in the device, thereby improving the luminous efficiency and service life of the device, has always been a problem that technicians in this field need to solve. Summary of the invention

[0004] The embodiments of the present application provide an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound has good performance in transmitting and adjusting charge balance, and can be used as a light-emitting auxiliary material in an organic light-emitting device to reduce the operating voltage, improve the light-emitting efficiency and extend the service life.

[0005] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, and the chemical structural formula of the organic compound is shown in Formula M:

[0006]

[0007] Among them, L 1 and L2 is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group;

[0008] R 1 and R 2 is selected from hydrogen, deuterium, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;

[0009] n1 is selected from any integer from 1 to 5;

[0010] n2 is selected from any integer from 1 to 7;

[0011] The L 1 and the R 2 At least one of them contains a substituted or unsubstituted benzene ring group;

[0012] The Ar is selected from any one of the following structures:

[0013]

[0014] R is selected from deuterium, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms;

[0015] n3 is selected from any integer between 0 and 3;

[0016] n4 is selected from any integer between 0 and 4;

[0017] n5 is selected from any integer between 0 and 5;

[0018] n6 is selected from any integer between 0 and 6;

[0019] n7 is selected from any integer between 0 and 7;

[0020] n9 is any integer selected from 0 to 9.

[0021] According to the second aspect of the present application, a mixture is provided, which contains at least one organic functional material and at least one organic compound as described above, and the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, luminescent materials, main materials, covering layer materials and organic dyes.

[0022] According to the third aspect of the present application, a composition is also provided, which comprises at least one organic solvent and at least one of the organic compounds mentioned above, or the composition comprises at least one of the organic solvents and at least one of the mixtures mentioned above.

[0023] According to a fourth aspect of the present application, an organic light-emitting device is also provided, the organic light-emitting device comprising:

[0024] a first electrode;

[0025] a second electrode, arranged opposite to the first electrode;

[0026] An organic functional layer is located between the first electrode and the second electrode; the material of the organic functional layer includes at least one of the organic compounds described above, or the material of the organic functional layer includes the mixture described above, or the organic functional layer is made of the composition described above.

[0027] According to a fifth aspect of the present application, a display panel is also provided, comprising the organic light-emitting device described above.

[0028] In the organic compound, mixture, composition, organic light-emitting device and display panel of the embodiment of the present application, the organic compound shown in formula M is an organic conjugated molecule based on an aromatic amine group, and the electrophilic hybridized nitrogen atom gives the organic compound molecule redox ability, and the 9,9-dimethylfluorene group double-substituted at positions 2 and 6 and the dibenzofuran group are matched together to bring suitable hole transport ability, exciton blocking ability and thermal stability, especially when the organic compound is used as a red light emitting auxiliary material, the suitable molecular orbital energy level can effectively reduce the energy level barrier between the hole transport layer and the light-emitting layer, optimize the carrier transport process, thereby increasing the carrier transport rate, and then effectively improving the luminous efficiency of the light-emitting device. At the same time, due to the high thermal stability of the organic compound, the service life of the light-emitting device to which the organic compound is applied can be effectively improved. Therefore, applying the organic compound shown in formula M to an organic light-emitting device can reduce the voltage of the organic light-emitting device, improve the luminous efficiency of the organic light-emitting device, and increase the service life of the organic light-emitting device.

[0029] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same figure numbers represent the same parts in the following description.

[0031] Figure 1It is a schematic diagram of the structure of an organic light-emitting device provided in an embodiment of the present application.

[0032] Figure numerals: 100, organic light-emitting device; 1, substrate; 11, first electrode (anode); 12, hole injection layer; 13, hole transport layer; 14, light-emitting auxiliary layer; 15, organic light-emitting layer; 16, electron transport layer; 17, electron injection layer; 18, second electrode (cathode). DETAILED DESCRIPTION

[0033] The technical solutions in the embodiments of the present application will be described clearly and completely in conjunction with the accompanying drawings. 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 technical solutions of the present application, and are not used to limit the present application. In the present application, unless otherwise specified, the directional words used, such as "upper" and "lower", generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings; while "inside" and "outside" refer to the outline of the device. In the present application, "optionally", "optional", and "optional" refer to optional, that is, to select from any of the two parallel solutions of "yes" or "no". If multiple "optional" appear in a technical solution, if there is no special explanation, and there is no contradiction or mutual restriction, each "optional" is independent of each other. 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 containing the listed features.

[0034] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0035] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0036] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0037] 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.

[0038] 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 atom, cyano, isocyano, nitro, halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, , cyano, isocyano, nitro, halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro, halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups can also be further substituted by substituents acceptable in the art.

[0039] In the present application, "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) obtained by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "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.

[0040] 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 a polycyclic ring, 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 understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, diaryl ether system should also be included in the definition of aromatic group.

[0041] 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 can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, Pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0042] 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, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0043] 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)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0044] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0045] In the present application, the term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0046] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0047] 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.

[0048] 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.

[0049] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0050] 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 In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0051] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0052] The present application embodiment provides an organic compound, the chemical structure of the organic compound is shown in Formula M:

[0053]

[0054] Among them, L 1 and L 2 is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group;

[0055] R 1 and R 2 is selected from hydrogen, deuterium, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;

[0056] n1 is selected from any integer from 1 to 5;

[0057] n2 is selected from any integer from 1 to 7;

[0058] The L 1 and the R 2 At least one of them contains a substituted or unsubstituted benzene ring group;

[0059] The Ar is selected from any one of the following structures:

[0060]

[0061] R is selected from deuterium, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms;

[0062] n3 is selected from any integer between 0 and 3;

[0063] n4 is selected from any integer between 0 and 4;

[0064] n5 is selected from any integer between 0 and 5;

[0065] n6 is selected from any integer between 0 and 6;

[0066] n7 is selected from any integer between 0 and 7;

[0067] n9 is any integer selected from 0 to 9.

[0068] It is understandable that the benzene ring group mentioned above refers to phenyl, phenylene or other groups containing a benzene ring. 1 When it is a single bond, R 2 contains substituted or unsubstituted phenyl; when L 1 When R is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group, 2 The phenyl group may not contain a phenyl group, or may contain a substituted or unsubstituted phenyl group.

[0069] In the embodiment of the present application, the organic compound shown in formula M is an organic conjugated molecule based on an aromatic amine group, and the electrophilic hybridized nitrogen atom gives the organic compound molecule redox ability, and the 9,9-dimethylfluorene group and the dibenzofuran group at positions 2 and 6 are paired together to bring suitable hole transport ability, exciton blocking ability and thermal stability, especially when the organic compound is used as a red light emitting auxiliary material, the suitable molecular orbital energy level can effectively reduce the energy level barrier between the hole transport layer and the light-emitting layer, optimize the carrier transport process, thereby increasing the carrier transfer rate, and then effectively improving the luminous efficiency of the light-emitting device. At the same time, due to the high thermal stability of the organic compound, the service life of the light-emitting device to which the organic compound is applied can be effectively improved. Therefore, applying the organic compound shown in formula M to an organic light-emitting device can reduce the voltage of the organic light-emitting device, improve the luminous efficiency of the organic light-emitting device, and increase the service life of the organic light-emitting device.

[0070] In some embodiments, Ar is selected from any one of the following structures:

[0071]

[0072] In some embodiments, the R 1 Selected from hydrogen or deuterium.

[0073] In some embodiments, the R 2 is selected from hydrogen or phenyl.

[0074] In some embodiments, the L 1 At least one selected from a single bond, unsubstituted or deuterium-substituted phenylene, and naphthylene.

[0075] In some embodiments, the L 2 is selected from a single bond or phenylene.

[0076] In some embodiments, the organic compound is selected from at least one of Formula 1-1 to Formula 1-168:

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] The structures of the organic compounds represented by Formula M provided in the present application are not limited to the structures listed above, and these structures can be arbitrarily substituted.

[0086] The organic compound shown in Formula M provided in the present application can be used as an organic functional material in an organic functional layer of an organic electronic device. The organic functional layer includes but is not limited to a hole injection layer (HIL), a hole transport layer (HTL), an electron injection layer (EIL), an electron transport layer (ETL), a prime layer (Prime), a hole blocking layer (HBL), a capping layer (CPL), and an emission material layer (EML).

[0087] In some embodiments, the organic compound represented by Formula M provided in the embodiments of the present application is used in a light-emitting auxiliary layer of an electronic device. In other words, the organic compound represented by Formula M can be used as a light-emitting auxiliary material.

[0088] In some embodiments, the organic compound represented by Formula M can be used as a red light emitting auxiliary material, a green light emitting auxiliary material, and a blue light emitting auxiliary material.

[0089] In a preferred embodiment, the organic compound represented by formula M is a red light emitting auxiliary material.

[0090] It should be noted that the organic compound represented by formula M can be used as any one of red light emitting auxiliary materials, green light emitting auxiliary materials and blue light emitting auxiliary materials, especially as a red light emitting auxiliary material, which has a better effect on improving the luminous efficiency and service life of the device.

[0091] The embodiment of the present application also provides a polymer, wherein the monomer of the polymer includes an organic compound represented by formula M.

[0092] The present application also provides a mixture, which comprises at least one organic compound shown in Formula M and at least one organic functional material. The organic functional material can be selected from at least one of hole injection material, hole transport material, electron injection material, electron transport material, luminescent auxiliary material, hole blocking material, luminescent material, main material, covering layer material and organic dye. 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 herein by reference.

[0093] An embodiment of the present application also provides a composition, which comprises at least one organic compound represented by formula M or the above mixture, and at least one organic solvent (first organic solvent), wherein the organic solvent is selected from at least one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefin compounds, boric esters or phosphate compounds.

[0094] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0095] Examples of aromatic or heteroaromatic solvents suitable for the present application 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, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0096] Examples of aromatic ketone-based solvents suitable for the present application 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.

[0097] Examples of aromatic ether-based solvents suitable for the present application 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.

[0098] Examples of aliphatic ketone-based solvents suitable for the present application 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.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0099] Examples of ester-based solvents suitable for the present application 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, and isononyl isononanoate are particularly preferred.

[0100] In some embodiments, the composition further comprises a second organic solvent, and the second organic solvent is selected from 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.

[0101] In some embodiments, solvents particularly suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0102] 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;

[0103] δp (polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0104] δh (hydrogen bond force) is between 0.9 and 14.2 MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0105] For the composition provided in the embodiments of the present application, the boiling point parameter of the organic solvent should be considered when selecting. In the embodiments of the present application, the boiling point of the organic solvent 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 the inkjet print head. The organic solvent can evaporate from the solvent system to form a film containing a functional material.

[0106] In some embodiments, the composition is a solution.

[0107] In some embodiments, the composition is a suspension.

[0108] In the present application, the mass fraction of the organic compound or the mixture in the composition ranges from 0.01% to 20%. Further, the mass fraction of the organic compound or the mixture in the composition ranges from 0.1% to 15%. Preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.2% to 10%.

[0109] In some embodiments, the mass fraction of the organic compound or the mixture in the composition is 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.5%, 0.8%, 1%, 3%, 5%, 8%, 10%, 12%, 15%, 18% or 20%.

[0110] The present application also provides a use of the composition as a coating or printing ink in the preparation of an organic electronic device. A particularly preferred use is to use the composition as a coating or printing ink and prepare an organic electronic device by a printing or coating preparation method.

[0111] 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 or pad printing, slit extrusion coating, etc. The preferred ones are gravure printing, nozzle printing and inkjet printing. The solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. Relevant printing technology and its related requirements for relevant solutions, such as solvents and concentrations, viscosity, etc.

[0112] An embodiment of the present application further provides an organic electronic device, wherein the material of the organic electronic device comprises the organic compound represented by the above formula M or the above mixture, or the organic electronic device is prepared from the above composition.

[0113] The organic electronic devices include, but are not limited to, organic light-emitting diodes (OLED), organic photovoltaic cells (OPV), organic light-emitting cells (OLEEC), organic field-effect transistors (OFET), organic light-emitting field-effect transistors (OLEFET), organic lasers, organic spin electronic devices, organic sensors and organic plasmon emitting diodes (OPED), etc. Preferably, the organic electronic device is an organic electroluminescent device, such as OLED, OLEEC or OLEFET.

[0114] like Figure 1 As shown, an embodiment of the present application further provides an organic light-emitting device 100, which is an organic electronic device, and the organic light-emitting device 100 includes a first electrode 11, a second electrode 18 arranged opposite to the first electrode 11, and an organic functional layer located between the first electrode 11 and the second electrode 18, and the material of the organic functional layer includes at least one of the organic compounds represented by the above formula M, or the material of the organic functional layer includes the mixture described above, or the organic functional layer is prepared by using the organic compound, mixture or composition described above.

[0115] In one embodiment, the first electrode 11 is an anode, and the second electrode 18 is a cathode.

[0116] Specifically, the organic functional layer is selected from at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a light-emitting auxiliary layer and an organic light-emitting layer. Preferably, the organic functional layer at least includes a light-emitting auxiliary layer and an organic light-emitting layer stacked.

[0117] Specifically, the organic light-emitting device 100 further includes a substrate 1 , and the first electrode 11 is disposed on the substrate 1 .

[0118] In a specific embodiment, the organic functional layer includes a hole injection layer 12, a hole transport layer 13, a luminescence auxiliary layer 14, an organic light-emitting layer 15, an electron transport layer 16 and an electron injection layer 17 stacked in sequence on the first electrode 11, wherein the material of the luminescence auxiliary layer 14 includes a luminescence auxiliary material, and the luminescence auxiliary material is selected from at least one organic compound represented by formula M.

[0119] In a specific embodiment, the luminescent auxiliary material is any one or more of a red light luminescent auxiliary material, a green light luminescent auxiliary material and a blue light luminescent auxiliary material. That is, the organic compound shown in formula M provided in the embodiment of the present application can be used as a red light luminescent auxiliary material, a green light luminescent auxiliary material and a blue light luminescent auxiliary material.

[0120] It can be understood that the organic compound provided in the embodiments of the present application can be applied to a red light emitting device, a green light emitting device or a blue light emitting device, and can be used as a light emitting auxiliary material in the device.

[0121] The organic light-emitting device 100 includes, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light-emitting field effect transistor (OLEFET), an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emission diode (OPED), etc., and particularly preferred are organic electroluminescent devices such as OLED, OLEEC or OLEFET.

[0122] In some embodiments, the organic light emitting device 100 is an OLED, which includes a substrate (eg, substrate 1 ), an anode (eg, first electrode 11 ), at least one light emitting layer, and a cathode (eg, second electrode 18 ).

[0123] Wherein, the substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting component. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. In some embodiments, the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred example, the substrate is flexible and can be selected from a polymer film or plastic, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0124] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the HIL or HTL or EML. In one example, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or EBL is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide, etc. Other suitable anode materials are known and can be easily selected for use by a person of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, or electron beam, etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.

[0125] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material as the EIL or ETL or HBL is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device of the present application. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation or electron beam, etc.

[0126] In some embodiments, in the organic light-emitting device provided in the embodiments of the present application, the light-emitting layer thereof is prepared by the composition provided in the embodiments of the present application.

[0127] Specifically, the light emitting wavelength of the organic light emitting device provided in the embodiment of the present application is in the range of 300 nanometers (nm) to 1000 nm.

[0128] In some embodiments, the light emitting device provided in the embodiments of the present application has a light emitting wavelength ranging from 350 nm to 900 nm. In other embodiments, the light emitting device provided in the embodiments of the present application has a light emitting wavelength ranging from 400 nm to 800 nm.

[0129] The embodiments of the present application also provide an application of the above-mentioned organic electronic device in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0130] The embodiments of the present application also provide an electronic device including the organic electronic device provided in the embodiments of the present application, including but not limited to a display device, a lighting device, a light source, a sensor, etc.

[0131] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the inventive concept of the present application, those skilled in the art should be aware that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific embodiments

[0133] The organic compound and its preparation method of the present application are further described in detail below in conjunction with specific examples. The raw materials used in the following examples are all commercially available products unless otherwise specified.

[0134] (I) Synthesis Examples of Organic Compounds

[0135] Example 1

[0136] The synthetic route of organic compound 1-1 is as follows:

[0137]

[0138] Synthesis of intermediate Sub-3:

[0139] Sub-1 (0.2 mol) and Sub-2 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100°C under a nitrogen atmosphere and refluxed for 4 hours; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-3 was obtained by column chromatography with a yield of 85%. The electrospray ionization mass spectrometry (ESI-MS) result of the intermediate Sub-3 was: m / z [H + ]=362.

[0140] Synthesis of organic compound 1-1:

[0141] Sub-3 (0.16 mol) and Sub-4 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-1 was obtained by column chromatography with a yield of 70%. The m / z [H + ]=604.

[0142] Example 2

[0143] The synthetic route of organic compound 1-6 is as follows:

[0144]

[0145] The synthesis of the intermediate Sub-3 can refer to the description in Example 1 and will not be repeated here.

[0146] Synthesis of organic compounds 1-6:

[0147] Sub-3 (0.16 mol) and Sub-5 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and organic compound 1-6 was obtained by column chromatography with a yield of 72%. The m / z [H + ]=604.

[0148] Example 3

[0149] The synthetic route of organic compound 1-10 is as follows:

[0150]

[0151] The synthesis of the intermediate Sub-3 can refer to the description in Example 1 and will not be repeated here.

[0152] Synthesis of organic compounds 1-10:

[0153] Sub-3 (0.16 mol) and Sub-6 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol), and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and column chromatography was performed to obtain organic compound 1-10 with a yield of 87%. The m / z [H + ]=604.

[0154] Example 4

[0155] The synthetic route of organic compound 1-28 is as follows:

[0156]

[0157] Synthesis of intermediate Sub-8:

[0158] Sub-1 (0.2 mol) and Sub-7 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-8 was obtained by column chromatography with a yield of 81%. The m / z [H + ]=412.

[0159] Synthesis of organic compound 1-28:

[0160] Sub-8 (0.16 mol) and Sub-6 (0.18 mol) were weighed and placed in a clean three-necked flask, Pd132 (5.0 mmol), X-Phos (10.0 mmol), and sodium tert-butoxide (0.32 mol) were added and dissolved in toluene, and nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was cooled naturally, it was washed with water and separated, the organic phase was dried and then spin-dried, and organic compound 1-28 was obtained by column chromatography with a yield of 86%. The m / z [H + ]=654.

[0161] Example 5

[0162] The synthetic route of organic compound 1-34 is as follows:

[0163]

[0164] Synthesis of intermediate Sub-10:

[0165] Sub-1 (0.2 mol) and Sub-9 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-10 was obtained by column chromatography with a yield of 87%. The m / z [H + ]=416.

[0166] Synthesis of organic compound 1-34:

[0167] Sub-10 (0.16 mol) and Sub-11 (0.18 mol) were weighed and placed in a clean three-necked flask, Pd132 (5.0 mmol), X-Phos (10.0 mmol), and sodium tert-butoxide (0.32 mol) were added and dissolved in toluene, and nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was cooled naturally, it was washed with water and separated, the organic phase was dried and then spin-dried, and organic compound 1-34 was obtained by column chromatography with a yield of 67%. The m / z [H + ]=654.

[0168] Example 6

[0169] The synthetic route of organic compound 1-50 is as follows:

[0170]

[0171] Synthesis of intermediate Sub-13:

[0172] Sub-1 (0.2 mol) and Sub-12 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-13 was obtained by column chromatography with a yield of 82%. The m / z [H + ]=438.

[0173] Synthesis of organic compound 1-50:

[0174] Sub-13 (0.16 mol) and Sub-14 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-50 was obtained by column chromatography with a yield of 79%. The m / z [H + ]=680.

[0175] Example 7

[0176] The synthetic route of organic compound 1-60 is as follows:

[0177]

[0178] The synthesis of the intermediate Sub-13 can be referred to the description in Example 6, which will not be repeated here.

[0179] Synthesis of organic compound 1-60:

[0180] Sub-13 (0.2 mol) and Sub-15 (0.22 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-60 was obtained by column chromatography with a yield of 73%. The m / z [H + ]=680.

[0181] Example 8

[0182] The synthetic route of organic compound 1-67 is as follows:

[0183]

[0184] The synthesis of the intermediate Sub-13 can be referred to the description in Example 6, which will not be repeated here.

[0185] Synthesis of organic compound 1-67:

[0186] Sub-13 (0.2 mol) and Sub-16 (0.22 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried. Column chromatography was performed to obtain organic compound 1-67 with a yield of 86%. The m / z [H + ]=680.

[0187] Example 9

[0188] The synthetic route of organic compound 1-73 is as follows:

[0189]

[0190] The synthesis of the intermediate Sub-13 can be referred to the description in Example 6, which will not be repeated here.

[0191] Synthesis of organic compound 1-73:

[0192] Sub-13 (0.2 mol) and Sub-17 (0.22 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried. Column chromatography was performed to obtain organic compound 1-73 with a yield of 76%. The m / z [H + ]=680.

[0193] Example 10

[0194] The synthetic route of organic compound 1-84 is as follows:

[0195]

[0196] Synthesis of intermediate Sub-19:

[0197] Sub-1 (0.2 mol) and Sub-18 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100°C under a nitrogen atmosphere and refluxed for 4 hours; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-19 was obtained by column chromatography with a yield of 80%. The m / z [H + ]=438.

[0198] Synthesis of organic compound 1-84:

[0199] Sub-19 (0.16 mol) and Sub-6 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol), and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried. Column chromatography was performed to obtain organic compound 1-84 with a yield of 88%. The m / z [H + ]=680.

[0200] Embodiment 11

[0201] The synthetic route of organic compound 1-113 is as follows:

[0202]

[0203] Synthesis of intermediate Sub-21:

[0204] Sub-1 (0.2 mol) and Sub-20 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-21 was obtained by column chromatography with a yield of 77%. The m / z [H + ]=438.

[0205] Synthesis of organic compound 1-113:

[0206] Sub-21 (0.16 mol) and Sub-22 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-113 was obtained by column chromatography with a yield of 52%. The m / z [H + ]=680.

[0207] Example 12

[0208] The synthetic route of organic compound 1-121 is as follows:

[0209]

[0210] The synthesis of the intermediate Sub-21 can refer to the description of Example 11 and will not be repeated here.

[0211] Synthesis of organic compound 1-121:

[0212] Sub-21 (0.2 mol) and Sub-6 (0.22 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-121 was obtained by column chromatography with a yield of 69%. The m / z [H + ]=680.

[0213] Example 13

[0214] The synthetic route of organic compound 1-136 is as follows:

[0215]

[0216] The synthesis of the intermediate Sub-21 can refer to the description of Example 11 and will not be repeated here.

[0217] Synthesis of organic compound 1-136:

[0218] Sub-21 (0.2 mol) and Sub-22 (0.22 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-136 was obtained by column chromatography with a yield of 67%. The m / z [H + ]=680.

[0219] Embodiment 14

[0220] The synthetic route of organic compound 1-143 is as follows:

[0221]

[0222] Synthesis of intermediate Sub-24:

[0223] Sub-1 (0.2 mol) and Sub-23 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the intermediate Sub-24 was obtained by column chromatography with a yield of 75%. The m / z [H + ]=462.

[0224] Synthesis of organic compound 1-143:

[0225] Sub-24 (0.16 mol) and Sub-6 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-143 was obtained by column chromatography with a yield of 78%. The m / z [H + ]=704.

[0226] Embodiment 15

[0227] The synthetic route of organic compound 1-152 is as follows:

[0228]

[0229] Synthesis of intermediate Sub-26:

[0230] Sub-1 (0.2 mol) and Sub-25 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the intermediate Sub-26 was obtained by column chromatography with a yield of 85%. The m / z [H + ]=488.

[0231] Synthesis of organic compound 1-152:

[0232] Sub-26 (0.16 mol) and Sub-16 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-152 was obtained by column chromatography with a yield of 87%. The m / z [H + ]=730.

[0233] Example 16

[0234] The synthetic route of organic compound 1-153 is as follows:

[0235]

[0236] Synthesis of intermediate Sub-28:

[0237] Sub-27 (0.2 mol) and Sub-12 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd2(dba)3 (1.0 mmol), tri-tert-butylphosphine (2.0 mmol) and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 100° C. and refluxed for 6 h under a nitrogen atmosphere; after the reaction solution was cooled naturally, it was washed with water and separated, and the organic phase was dried and spin-dried, and the intermediate Sub-28 was obtained by column chromatography with a yield of 88%. The m / z [H + ]=443.

[0238] Synthesis of organic compound 1-153:

[0239] Sub-28 (0.16 mol) and Sub-6 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol) and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-153 was obtained by column chromatography with a yield of 82%. The m / z [H + ]=685.

[0240] Embodiment 17

[0241] The synthetic route of organic compound 1-159 is as follows:

[0242]

[0243] The synthesis of the intermediate Sub-13 can be referred to the description in Example 6, which will not be repeated here.

[0244] Synthesis of organic compound 1-159:

[0245] Sub-13 (0.2 mol) and Sub-29 (0.22 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol), and sodium tert-butoxide (0.4 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 4 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-159 was obtained by column chromatography with a yield of 86%. The m / z [H + ]=684.

[0246] Embodiment 18

[0247] The synthetic route of organic compound 1-168 is as follows:

[0248]

[0249] Synthesis of intermediate Sub-32:

[0250] Sub-30 (0.2 mol) and Sub-31 (0.2 mol) were weighed and placed in a clean three-necked flask, and Pd(PPh3)4 (10.0 mmol), potassium carbonate (0.8 mol), toluene (1000 mL), ethanol (500 mL) and deionized water (500 mL) were added. The nitrogen was replaced three times, and the reaction solution was heated to 100 ° C and refluxed for 12 h under a nitrogen atmosphere; after the reaction solution was cooled naturally, it was washed with water and separated, the organic phase was dried and then spin-dried, and the intermediate Sub-32 was obtained by column chromatography with a yield of 91%. The m / z [H + ]=405.

[0251] Synthesis of organic compound 1-168:

[0252] Sub-3 (0.16 mol) and Sub-32 (0.18 mol) were weighed and placed in a clean three-necked flask, and Pd132 (5.0 mmol), X-Phos (10.0 mmol), and sodium tert-butoxide (0.32 mol) dissolved in toluene were added, and the nitrogen was replaced three times. The reaction solution was heated to 110° C. under a nitrogen atmosphere and refluxed for 6 h; after the reaction solution was naturally cooled, it was washed with water and separated, and the organic phase was dried and then spin-dried, and the organic compound 1-168 was obtained by column chromatography with a yield of 73%. The m / z [H + ]=730.

[0253] Comparative Example

[0254] The present application also provides comparative compounds REF01 and REF02, whose chemical structures are shown below:

[0255]

[0256] (II) Energy level calculation of organic compounds and comparative compounds

[0257] In the examples of the present application, the energy level of the organic compound plays a key role. The highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of the organic compounds obtained in Examples 1 to 18 of the present application and the comparative compounds REF01 and REF02 can be obtained by theoretical calculation. Specifically, the theoretical calculation part is mainly calculated by the Gaussian 09W (Gaussian Inc.) software package, and the specific simulation method can be found in WO2011141110 or described in the following examples. It should be noted that the values ​​of HOMO and LUMO depend on the measurement method or calculation method used, and even for the same method, different evaluation methods, such as the starting point and peak value on the CV curve, can give different HOMO / LUMO values. Therefore, a reasonable and meaningful comparison should be carried out with the same measurement method and the same evaluation method. In the embodiments of the present application, the ground state (S0) configuration is calculated according to the density functional theory (DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set, and the HOMO and LUMO values ​​of the material are calculated according to the optimized S0 structure using the time-dependent density functional theory (TD-DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set, and the unit is Hartree.

[0258] The calculation results of the HOMO energy level, LUMO energy level and S1 energy level of the organic compounds obtained in Examples 1 to 18 of the present application and the comparative compounds REF01 and REF02 provided in the comparative examples are shown in Table 1.

[0259] Table 1

[0260]

[0261]

[0262] As can be seen from Table 1, the HOMO energy levels of the organic compounds provided in Examples 1 to 18 of the present application are maintained at the same level as the HOMO energy levels of the comparative compounds REF01 and REF02, indicating that these organic compounds are suitable for luminescent auxiliary materials, which can optimize the hole transport capacity and reduce the energy level barrier between the hole transport layer and the light-emitting layer.

[0263] (III) Preparation and characterization of OLED devices

[0264] by Figure 1 Taking the preparation of the organic light-emitting device shown in the figure as an example, the preparation method of the OLED device using the organic compound of the present application is described in detail below through an embodiment of a specific device preparation method.

[0265] In the following method for preparing an OLED device, ITO conductive glass is used as an anode substrate, PD is used as a hole injection material, HT is used as a hole transport material, Host is used as a main material of the light-emitting layer, Dopant is used as a doping material of the light-emitting layer, HB is used as a hole blocking material, ET and Liq are used as electron transport materials, Liq is used as an electron injection material, and Al is used as a cathode material. In addition, the organic compounds of the aforementioned synthetic examples are used as light-emitting auxiliary materials to prepare corresponding OLED devices. The chemical structures of PD, HT, Host, Dopant, ET and Liq are shown below:

[0266]

[0267] The preparation process of an OLED device using the above materials is described in detail below through specific examples.

[0268] Taking the method for preparing an OLED device using organic compound 1-1 as a light-emitting auxiliary material as an example, the prepared OLED device is recorded as "OLED-1 device". The method for preparing the OLED-1 device includes the following steps:

[0269] Step a: ITO conductive glass substrate (equivalent to Figure 1 Cleaning of the substrate 1 having the anode 11 formed thereon. An ITO conductive glass substrate is provided, and the substrate is ultrasonically cleaned using one or more cleaning agents such as deionized water, acetone, isopropanol or chloroform to improve the work function of the anode 11.

[0270] Step b: forming a hole injection layer 12 on the anode 11. The hole injection materials PD and HT were evaporated on the anode 11 at a evaporation rate of 3:97, and the hole injection layer 12 with a thickness of 30 nm was obtained.

[0271] Step c: forming a hole transport layer 13 on the hole injection layer 12. The hole transport material HT was evaporated on the hole injection layer 12 at an evaporation rate of , to obtain a hole transport layer 13 with a thickness of 60 nm.

[0272] Step d: forming a light-emitting auxiliary layer 14 on the hole transport layer 13. The compound 1-1 provided in the above embodiment was evaporated on the hole transport layer 13 at an evaporation rate of to obtain a light-emitting auxiliary layer 14 with a thickness of 10 nm.

[0273] Step e: forming a light-emitting layer 15 on the light-emitting auxiliary layer 14. Host and Dopant are evaporated on the light-emitting auxiliary layer 14 at a evaporation rate of 98:2, and the light-emitting layer 15 with a thickness of 25 nm is obtained.

[0274] Step f: forming an electron transport layer 16 on the light emitting layer 15. In a vacuum chamber, the electron transport material ET and Liq are placed in different evaporation crucibles and placed in a high vacuum environment (1×10 -6 ET and Liq were co-deposited at a weight ratio of 5:5 at 30 mbar to form an electron transport layer 16 with a thickness of 30 nm on the light emitting layer 15.

[0275] Step g: forming an electron injection layer 17 on the electron transport layer 16. The electron injection material Liq is evaporated on the electron transport layer 16 at a evaporation rate of to obtain the electron injection layer 17 with a thickness of 1 nm.

[0276] Step h: forming a cathode 18 on the electron injection layer 17. The cathode material Al is evaporated on the electron injection layer 17 at an evaporation rate to obtain a cathode 18 with a thickness of 100 nm.

[0277] Step i: placing the device obtained by layer-by-layer deposition in a nitrogen atmosphere glove box and encapsulating it with a UV-curable resin to finally obtain an OLED-1 device.

[0278] In the embodiment of the present application, the structure of the prepared OLED-1 device is: ITO / PD:HT(3:97,10nm) / HT(130nm) / organic compound 1-1(90nm) / host:Dopant(3%,40nm) / ET:Liq(5:5,30nm) / Liq(1nm) / Al(100nm).

[0279] The preparation of OLED-2 to OLED-18 devices refers to the preparation method of device OLED-1, and the organic compounds synthesized in the above-mentioned Examples 2 to 18 are respectively selected as the light-emitting auxiliary materials of the OLED devices, and OLED-2 to OLED-18 devices are prepared accordingly. It can be understood that in the preparation methods of the above-mentioned OLED-1 to OLED-18 devices, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0280] Further, referring to the preparation method of the device embodiment, comparative compounds REF01 and REF02 were used as luminescent auxiliary materials to prepare comparative example OLED-REF01 and OLED-REF02 devices. Compared with the preparation method of OLED-1 device, the preparation methods of OLED-REF01 and OLED-REF02 devices are the same except for the different luminescent auxiliary materials.

[0281] In the present embodiment, the current-voltage (JV) characteristics of OLED-1 to OLED-18, OLED-REF01 and OLED-REF02 devices were characterized, and important parameters such as luminous efficiency and service life were recorded. The results are shown in Table 2. Among them, the luminous efficiency is the current density of 10mA / cm 2 The relative value obtained when the device is used up, the service life (LT95) is the time taken for the device brightness to drop from the initial 1knit to 95% under constant current.

[0282] Table 2

[0283]

[0284] It can be seen from Table 2 that when the organic compounds provided in Examples 1 to 18 of the present application are used as light-emitting auxiliary materials, the operating voltage of the prepared organic light-emitting devices OLED-1 to OLED-18 is significantly lower than the operating voltage of the comparative devices OLED-REF01 and OLED-REF02. This indicates that the organic compounds provided in the present application have better hole transport capabilities, which can effectively reduce interlayer carrier accumulation and balance the overall carrier transport of the device. Therefore, using the organic compounds provided in the present application as light-emitting auxiliary layer materials for organic light-emitting devices can bring about lower operating voltage, higher luminous efficiency and longer device life.

[0285] 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 the specification of this application.

[0286] The above-described embodiments only express several implementation methods of the present application, which is convenient for understanding the technical solution of the present application in detail, but it cannot be understood as limiting the scope of protection of the application. It should be pointed out that for ordinary technicians in this field, without departing from the inventive concept of the present application, several modifications and improvements can be made, which all belong to the scope of protection of the present application. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments on the basis of the technical solutions provided in the present application are all within the scope of protection of the claims attached to the present application. Therefore, the scope of protection of the present application shall be based on the contents of the attached claims, and the specification can be used to interpret the contents of the claims.

Claims

1. An organic compound, characterized in that The chemical structural formula of the organic compound is shown in Formula M: Among them, L 1 and L 2 is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted naphthylene group; R 1 and R 2 is selected from hydrogen, deuterium, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; n1 is selected from any integer from 1 to 5; n2 is selected from any integer from 1 to 7; The L 1 and the R 2 At least one of them contains a substituted or unsubstituted benzene ring group; The Ar is selected from any one of the following structures: R is selected from deuterium, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms; n3 is selected from any integer between 0 and 3; n4 is selected from any integer between 0 and 4; n5 is selected from any integer between 0 and 5; n6 is selected from any integer between 0 and 6; n7 is selected from any integer between 0 and 7; n9 is any integer selected from 0 to 9.

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

3. The organic compound according to claim 1 or 2, characterized in that The R 1 is selected from hydrogen or deuterium; The R 2 is selected from hydrogen or phenyl; The L 1 At least one selected from a single bond, unsubstituted or deuterium-substituted phenylene, and naphthylene; The L 2 is selected from a single bond or phenylene.

4. The organic compound according to claim 1 or 2, characterized in that The organic compound is selected from at least one of Formula 1-1 to Formula 1-168:

5. 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 4, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, luminescent materials, main materials, covering layer materials and organic dyes.

6. A composition, characterized in that The composition comprises at least one organic solvent and at least one organic compound as claimed in any one of claims 1 to 4, or the composition comprises at least one organic solvent and at least one mixture as claimed in claim 5.

7. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; An organic functional layer is located between the first electrode and the second electrode; the material of the organic functional layer includes at least one of the organic compounds described in any one of claims 1 to 4, or the material of the organic functional layer includes the mixture described in claim 5, or the organic functional layer is made of the composition described in claim 6.

8. The light emitting device according to claim 7, characterized in that: The organic functional layer includes a light-emitting auxiliary layer and an organic light-emitting layer which are stacked. The material of the light-emitting auxiliary layer includes a light-emitting auxiliary material, and the light-emitting auxiliary material is selected from at least one of the organic compounds.

9. The light emitting device according to claim 8, characterized in that: The light-emitting auxiliary material is a red light-emitting auxiliary material.

10. A display panel, characterized in that: Comprising the organic light emitting device as claimed in any one of claims 7 to 9.

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