Organic compound, mixture, composition, organic electronic device and display panel

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic electronic device and a display panel. The chemical structural formula of the organic compound is as shown in the general formula (1): # imgabs0. The organic compound provided by the invention has relatively high electron transport performance and chemical structural stability, so that the luminous efficiency of the organic electroluminescent device can be improved, and the service life of the organic electroluminescent device can be prolonged.

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 electronic 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 contains a multilayer structure, and the organic material of each layer is different. Specifically, the organic 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, an electron injection layer, etc. When the organic electroluminescent element is working, by applying a voltage between the anode and the cathode, the anode injects holes into the organic layer, and the cathode injects electrons into the organic 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] The key to determining the luminous efficiency of organic electroluminescent elements is the luminescent layer material, which often needs to have properties such as high quantum efficiency, sufficient carrier mobility, and stability. In order to avoid aggregation quenching, the luminescent layer material usually adopts a combination of host and guest doping to achieve effective utilization of exciton energy. However, the existing organic electroluminescent materials have insufficient transmission and low stability, which can easily lead to the voltage, efficiency and life of the device failing to meet the requirements, severely limiting the application of organic electroluminescent elements. Summary of the invention

[0004] The present application provides an organic compound, a mixture, a composition, an organic electronic device and a display panel. The organic compound has good carrier transport properties, can adjust charge balance, and promote energy transfer. It can be used as a main material in organic electronic devices to improve the luminous efficiency and life of the device.

[0005] The present invention provides an organic compound, the chemical structure of which is shown in general formula (1):

[0006]

[0007] Among them, X 1 Selected from O or S;

[0008] X 2 Selected from O, S or NR 3 ;

[0009] Z 1 , Z 2 and Z 3 is selected from CH or N, and Z 1 , Z 2 and Z 3 At least one of is selected from N;

[0010] Ar 1 and Ar 2 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 4 to 20 carbon atoms;

[0011] R 1 is selected from hydrogen or deuterium;

[0012] R 2 is selected from hydrogen, deuterium, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 4 to 20 carbon atoms;

[0013] R 3 is selected from substituted or unsubstituted aromatic groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 18 carbon atoms;

[0014] m is selected from any integer from 1 to 6;

[0015] n is any integer selected from 1 to 7.

[0016] In one embodiment of the present application, Z 1 , Z 2 and Z 3 Selected from N.

[0017] In one embodiment of the present application, Ar 1 and Ar 2 At least one selected from the group consisting of phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl and phenanthrinyl.

[0018] In one embodiment of the present application, R 2 At least one selected from the group consisting of hydrogen, deuterium, phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, and phenanthrinyl.

[0019] In one embodiment of the present application, R 3 At least one selected from phenyl, biphenyl, deuterated phenyl, and pyridyl.

[0020] In one embodiment of the present application, the organic compound is selected from any one of the following compounds represented by formula (P-1) to formula (P-160), compounds represented by formula (Q-1) to formula (Q-160), compounds represented by formula (R-1) to formula (R-128), and compounds represented by formula (S-1) to formula (S-100):

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[0052] According to the above-mentioned purpose of the present application, an embodiment of the present application also provides a mixture, which includes at least one of the organic compounds and at least one organic functional material, 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, guest materials, host materials and quantum dot materials.

[0053] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition, which includes at least one organic solvent and at least one organic compound, or the composition includes at least one organic solvent and the mixture.

[0054] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides an organic electronic device, wherein the organic electronic device comprises:

[0055] a first electrode;

[0056] a second electrode, arranged opposite to the first electrode;

[0057] An organic functional layer is located between the first electrode and the second electrode, wherein the material of the organic functional layer includes at least one of the organic compounds, or the material of the organic functional layer includes the mixture, or the organic functional layer is made of the composition.

[0058] In one embodiment of the present application, the organic functional layer includes a light-emitting layer, and a material of the light-emitting layer includes a first host material and a guest material, and the first host material includes at least one of the organic compounds.

[0059] In one embodiment of the present application, the material of the light-emitting layer further includes a second host material, the second host material includes a hole transport type host material, and the HOMO energy level of the second host material ranges from -5.2 eV to -5.5 eV.

[0060] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a display panel, which includes the organic electronic device.

[0061] The present application provides an organic compound, a mixture, a composition, an organic electronic device and a display panel. The molecular structure of the organic compound is composed of a plurality of electron-rich conjugated planar rigid groups, such as nitrogen heterocycles, oxygen / sulfur heteroatom fluorene rings, so that the organic compound has sufficiently strong electron transport and structural stability. When the organic compound is used in a light-emitting layer in combination with a hole transport type host material, effective transmission of excited state energy can be achieved, which is beneficial to improving the luminous efficiency and life of the organic electroluminescent device. In addition, when Z 1 , Z 2 and Z 3 When selected from N, the nitrogen heterocycle is directly connected to the No. 4 position of the dibenzoheterocycle, and is extended from the No. 1 position of the dibenzoheterocycle to connect to the second dibenzoheterocycle. The double substitution of the above positions makes the molecular conformation of the organic compound more compact, and the dihedral angle between the plane of the nitrogen heterocycle and the plane of the dibenzoheterocycle is reduced, so that the corresponding LUMO energy level orbital distribution area is more planar, thereby further improving the electron transport performance and chemical structure stability of the organic compound; therefore, the luminous efficiency and service life of the organic electronic device using the organic compound of the present application can be improved.

[0062] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0063] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application, and those skilled in the art can obtain other drawings based on these drawings without creative work.

[0064] 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.

[0065] Figure 1 It is a schematic diagram of the structure of the organic electronic device provided in the embodiment of the present application.

[0066] Description of reference numerals:

[0067] 100. Organic electronic device; 1. Substrate; 11. First electrode (anode); 12. Hole injection layer; 13. Hole transport layer; 14. Light-emitting auxiliary layer; 15. Light-emitting layer; 16. Electron transport layer; 17. Electron injection layer; 18. Second electrode (cathode). DETAILED DESCRIPTION

[0068] 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, unless otherwise stated, the directional words used, such as "upper" and "lower", generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings; 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 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 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.

[0069] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0070] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0071] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0072] 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.

[0073] 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 or 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 or 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 or 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.

[0074] 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.

[0075] 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 its derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, diaryl ether system should also be included in the definition of aromatic group.

[0076] 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, pyrimidine yl, triazine, 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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).

[0081] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0087] The present invention provides an organic compound, the chemical structure of which is shown in general formula (1):

[0088]

[0089] Among them, X 1 Selected from O or S;

[0090] X 2 Selected from O, S or NR 3 ;

[0091] Z 1 , Z 2 and Z 3 is selected from CH or N, and Z 1 , Z 2 and Z 3 At least one of is selected from N;

[0092] Ar 1 and Ar 2 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 4 to 20 carbon atoms;

[0093] R 1 is selected from hydrogen or deuterium;

[0094] R 2 is selected from hydrogen, deuterium, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 4 to 20 carbon atoms;

[0095] R 3 is selected from substituted or unsubstituted aromatic groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 18 carbon atoms;

[0096] m is selected from any integer from 1 to 6;

[0097] n is any integer selected from 1 to 7.

[0098] In the implementation and application process, the molecular structure of the organic compound provided in the embodiment of the present application is composed of a plurality of electron-rich conjugated planar rigid groups, such as nitrogen heterocycles, oxygen / sulfur heteroatom fluorene rings, so that the organic compound has sufficiently strong electron transport and structural stability. When the organic compound is used in the light-emitting layer in combination with a hole transport type host material, it can realize the effective transmission of excited state energy, which is beneficial to improve the luminous efficiency and life of the organic electroluminescent device; in addition, when Z 1 , Z 2 and Z 3 When selected from N, the nitrogen heterocycle is directly connected to the No. 4 position of the dibenzoheterocycle, and is extended from the No. 1 position of the dibenzoheterocycle to connect to the second dibenzoheterocycle. The double substitution of the above positions makes the molecular conformation of the organic compound more compact, and the dihedral angle between the plane of the nitrogen heterocycle and the plane of the dibenzoheterocycle is reduced, so that the corresponding LUMO energy level orbital distribution area is more planar, thereby further improving the electron transport performance and chemical structure stability of the organic compound; therefore, the luminous efficiency and service life of the organic electronic device using the organic compound of the present application can be improved.

[0099] In some embodiments, Z 1 , Z 2 and Z 3 Selected from N.

[0100] In some embodiments, Ar 1 and Ar 2Each of the at least one radicals is independently selected from the group consisting of phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl and phenanthrinyl.

[0101] Further, in some embodiments, Ar 1 and Ar 2 Each of the following is independently selected from any one of phenyl, biphenyl, pyridyl and isoquinolyl.

[0102] In some embodiments, R 2 Each occurrence is the same or different and is independently selected from at least one of hydrogen, deuterium, phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl and phenanthrinyl.

[0103] Furthermore, in some embodiments, R 2 Each occurrence is the same or different and is independently selected from any one of hydrogen, deuterium, phenyl, biphenyl, naphthyl, phenanthryl and deuterated phenyl.

[0104] In some embodiments, R 3 At least one selected from phenyl, biphenyl, deuterated phenyl, and pyridyl.

[0105] Furthermore, in some embodiments, R 3 Any one selected from phenyl, biphenyl and pyridyl.

[0106] In some embodiments, the organic compound is selected from any one of the following compounds represented by formula (P-1) to formula (P-160), compounds represented by formula (Q-1) to formula (Q-160), compounds represented by formula (R-1) to formula (R-128), and compounds represented by formula (S-1) to formula (S-100):

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[0139] The aromatic amine organic compound described in the present application can be used as a functional material in the organic functional layer of an electronic device. The organic functional layer includes a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), an electron blocking layer (EBL), a hole blocking layer (HBL), a luminescent auxiliary layer (Prime) and an emission material layer (EML).

[0140] In some embodiments, the organic compound described in the present application is used in a light-emitting layer; further, the organic compound can be used as a host material in the light-emitting layer.

[0141] Accordingly, the present application also provides a mixture, which includes at least one organic compound described in the above embodiments and at least one organic functional material, 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, guest materials, host materials and quantum dot materials.

[0142] The present application further provides a composition, which comprises at least one organic solvent and at least one organic compound described in the above embodiments, or the composition comprises at least one organic solvent and a mixture described in the above embodiments.

[0143] 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, borate esters or phosphate esters.

[0144] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based organic solvents.

[0145] Examples of aromatic or heteroaromatic organic 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, Benzene, 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.

[0146] Examples of aromatic ketone-based organic 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.

[0147] Examples of aromatic ether-based organic 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 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.

[0148] Examples of aliphatic ketone-based organic 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.

[0149] Examples of ester-based organic 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.

[0150] 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.

[0151] Optionally, in some embodiments, an organic solvent particularly suitable for the present application is a solvent having a Hansen solubility parameter within the following range:

[0152] δ d (Dispersion force) 17.0~23.2MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 scope;

[0153] δ p (Polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0154] δ h (Hydrogen bond force) 0.9~14.2MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0155] In the composition provided in the embodiment of the present application, the boiling point parameter of the organic solvent needs to be considered when selecting. In the embodiment 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; optimally ≥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.

[0156] In some embodiments, the composition provided in the embodiments of the present application is a solution.

[0157] In a preferred embodiment, the composition provided in the examples of the present application is a solution.

[0158] In a preferred embodiment, the composition provided in the examples of the present application is a suspension.

[0159] In the embodiment of the present application, the composition may include 0.01wt% to 20wt% of the organic compound or the mixture. Further, the organic compound or the mixture may be 0.1wt% to 15wt% in the composition. Preferably, the organic compound or the mixture may be 0.2wt% to 10wt% in the composition. The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device, and a particularly preferred preparation method is by printing or coating.

[0160] 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, slot extrusion coating, etc. Preferred 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, improving film-forming properties, improving adhesion, etc.

[0161] The present application also provides an organic electronic device 100 , which comprises the organic compound described in the above embodiment, the mixture described in the above embodiment, or is prepared from the composition described in the above embodiment.

[0162] Please refer to Figure 1 The organic electronic device 100 includes a substrate 1, a first electrode 11, an organic functional layer and a second electrode 18; the first electrode 11 and the second electrode are arranged opposite to each other, and the organic functional layer is located between the first electrode 11 and the second electrode 18.

[0163] In some embodiments, the material of the organic functional layer includes at least one organic compound described in the above embodiments, or the material of the organic functional layer includes the mixture described in the above embodiments, or the organic functional layer is made of the composition described in the above embodiments.

[0164] In some embodiments, the organic functional layer includes a light-emitting layer 15 disposed between the first electrode 11 and the second electrode 18, the light-emitting layer 15 includes a first host material and a guest material, and the first host material includes at least one of the organic compounds described in the above embodiments, or the mixture described in the above embodiments, or the combination described in the above embodiments.

[0165] In some embodiments, the material of the light-emitting layer also includes a second main material, which includes a hole-transporting main material, such as an aromatic amine compound, and the HOMO range of the second main material is -5.2eV to -5.5eV; the organic compound provided in the embodiment of the present application has good electron transport performance, and can balance carrier transport when combined with a second hole-transporting main material, ensuring that the energy utilization rate of the light-emitting layer is high enough and the transmission is stable enough; in addition, by adjusting the ratio of the first main material to the second main material, the problem of biased electron transmission or hole transmission can be avoided.

[0166] In some embodiments, the organic electronic device 100 includes a substrate 1, a first electrode 11, a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting layer 15, an electron transport layer 16, an electron injection layer 17 and a second electrode 18; that is, the organic functional layer may include a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting layer 15, an electron transport layer 16 and an electron injection layer 17

[0167] In some embodiments, the first electrode 11 may be an anode layer, and the second electrode 18 may be a cathode layer.

[0168] In some embodiments, the organic electronic device 100 includes a substrate 1 and a first electrode 11, a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting layer 15, an electron transport layer 16, an electron injection layer 17 and a second electrode 18 arranged in sequence on the substrate 1.

[0169] In some embodiments, the organic electronic device 100 includes 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., and particularly preferred are organic electroluminescent devices such as OLED, OLEEC, and OLEFET.

[0170] The organic electronic device 100 , especially the OLED, includes a substrate 1 , a first electrode 11 , at least one light-emitting layer 15 , and a second electrode 18 .

[0171] Substrate 1 can be opaque or transparent. A transparent substrate 1 can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. Substrate 1 can be rigid or elastic. Substrate 1 can be plastic, metal, semiconductor wafer or glass. It is best that substrate 1 has a smooth surface. Substrates 1 without surface defects are particularly ideal. In a preferred example, substrate 1 is flexible and can be selected from polymer films or plastics, whose glass transition temperature T g It is 150° C. or higher, preferably higher than 200° C., more preferably higher than 250° C., and most preferably higher than 300° C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene (2,6-naphthalene) (PEN).

[0172] The first electrode 11 may include a conductive metal or metal oxide, or a conductive polymer. The first electrode 11 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 first electrode 11 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 materials for the first electrode 11 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 materials for the first electrode 11 are known and can be easily selected for use by a person of ordinary skill in the art. The material of the first electrode 11 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, etc.

[0173] In some embodiments, the first electrode 11 is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare the device according to the present application.

[0174] The second electrode 18 may include a conductive metal or metal oxide. The second electrode 18 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 second electrode 18 and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer 15 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 the second electrode 18 materials of the organic electronic device in this application. Examples of materials for the second electrode 18 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 material of the second electrode 18 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, etc.

[0175] In some embodiments, the light-emitting layer 15 in the organic electronic device 100 provided in the embodiments of the present application is prepared using the composition provided in the above embodiments.

[0176] In some embodiments, the light emission wavelength of the organic electronic device 100 is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0177] In some embodiments, the organic electronic device 100 is applied in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0178] In some embodiments, the electronic device including the organic electronic device 100 includes but is not limited to a display device, a lighting device, a light source, a sensor, and the like.

[0179] The organic compounds provided by the present application will be described below in conjunction with preferred embodiments, but the organic compounds provided by the present application are 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 concept of the present application, technicians in this field should realize 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.

[0181] The organic compounds and preparation methods of the present invention 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.

[0182] Organic Compound Synthesis Examples

[0183] Example 1

[0184] The synthetic route of organic compound P-1 is as follows:

[0185]

[0186] Synthesis of compound P-1:

[0187] Weigh I-1 (0.5 mol) and I-2 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain compound P-1 with a yield of 80%. The electrospray ionization mass spectrometry (ESI-MS) result of compound P-1 is: m / z [H + ]=642.

[0188] Example 2

[0189] The synthetic route of organic compound P-14 is as follows:

[0190]

[0191] Synthesis of compound P-14:

[0192] Weigh I-1 (0.5 mol) and I-3 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound P-14 by column chromatography with a yield of 78%, m / z [H + ]=642.

[0193] Example 3

[0194] The synthetic route of organic compound P-35 is as follows:

[0195]

[0196] Synthesis of compound P-35:

[0197] Weigh I-1 (0.5 mol) and I-5 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound P-35 by column chromatography with a yield of 82%, m / z [H + ]=718.

[0198] Example 4

[0199] The synthetic route of organic compound P-63 is as follows:

[0200]

[0201] Synthesis of compound P-63:

[0202] Weigh I-1 (0.5 mol) and I-6 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound P-63, the yield is 73%, m / z [H + ]=718.

[0203] Example 5

[0204] The synthetic route of organic compound P-116 is as follows:

[0205]

[0206] Synthesis of intermediate I-9:

[0207] Weigh I-7 (0.8 mol) and I-8 (0.8 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 40 mmol), potassium carbonate (3.2 mol), toluene (4.0 L), ethanol (1.0 L), deionized water (1.0 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 10 h; after the reaction liquid is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain intermediate I-9, the yield is 75%, m / z [H + ]=435.

[0208] Synthesis of intermediate I-11:

[0209] Weigh I-9 (0.5 mol) and I-10 (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 hours; after the reaction liquid is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain the intermediate I-11, the yield is 86%, m / z [H + ]=526.

[0210] Synthesis of compound P-116:

[0211] Weigh I-11 (0.4 mol) and I-12 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 22 mmol), potassium carbonate (1.2 mol), toluene (2.0 L), ethanol (1.0 L), deionized water (1.0 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain compound P-116, the yield is 85%, m / z [H + ]=643.

[0212] Example 6

[0213] The synthetic route of organic compound P-135 is as follows:

[0214]

[0215] Synthesis of compound P-135:

[0216] Weigh I-13 (0.5 mol) and I-14 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain compound P-135, the yield is 82%, m / z [H + ]=648.

[0217] Example 7

[0218] The synthetic route of organic compound P-146 is as follows:

[0219]

[0220] Synthesis of compound P-146:

[0221] Weigh I-1 (0.5 mol) and I-15 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound P-146 by column chromatography with a yield of 77%, m / z [H + ]=642.

[0222] Example 8

[0223] The synthetic route of organic compound P-158 is as follows:

[0224]

[0225] Synthesis of compound P-158:

[0226] Weigh I-1 (0.5 mol) and I-16 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound P-158, the yield is 75%, m / z [H + ]=718.

[0227] Example 9

[0228] The synthetic route of organic compound Q-3 is as follows:

[0229]

[0230] Synthesis of compound Q-3:

[0231] Weigh I-1 (0.5 mol) and I-17 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound Q-3 by column chromatography with a yield of 88%, m / z [H + ]=658.

[0232] Example 10

[0233] The synthetic route of organic compound Q-11 is as follows:

[0234]

[0235] Synthesis of compound Q-11:

[0236] Weigh I-1 (0.5 mol) and I-18 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound Q-11 with a yield of 81%, m / z [H + ]=658.

[0237] Embodiment 11

[0238] The synthetic route of organic compound Q-17 is as follows:

[0239]

[0240] Synthesis of compound Q-17:

[0241] Weigh I-19 (0.5 mol) and I-20 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound Q-17, the yield is 85%, m / z [H + ]=734.

[0242] Example 12

[0243] The synthetic route of organic compound Q-49 is as follows:

[0244]

[0245] Synthesis of compound Q-49:

[0246] Weigh I-1 (0.5 mol) and I-21 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 8 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound Q-49 by column chromatography with a yield of 91%, m / z [H + ]=734.

[0247] Embodiment 13

[0248] The synthetic route of organic compound Q-81 is as follows:

[0249]

[0250] Synthesis of compound Q-81:

[0251] Weigh I-1 (0.5 mol) and I-22 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, separate the liquid, dry the organic phase and spin dry it, and obtain compound Q-81 by column chromatography with a yield of 86%, m / z [H + ]=708.

[0252] Embodiment 14

[0253] The synthetic route of organic compound Q-102 is as follows:

[0254]

[0255] Synthesis of compound Q-102:

[0256] Weigh I-1 (0.5 mol) and I-23 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain compound Q-102, the yield is 81%, m / z [H + ]=758.

[0257] Embodiment 15

[0258] The synthetic route of organic compound Q-124 is as follows:

[0259]

[0260] Synthesis of intermediate I-25:

[0261] Weigh I-24 (0.8 mol) and I-8 (0.8 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 40 mmol), potassium carbonate (3.2 mol), toluene (4.0 L), ethanol (1.0 L), deionized water (1.0 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 10 h; after the reaction liquid is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain intermediate I-25, the yield is 71%, m / z [H + ]=485.

[0262] Synthesis of intermediate I-26:

[0263] Weigh I-25 (0.5 mol) and I-10 (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 hours; after the reaction liquid is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain intermediate I-26, the yield is 83%, m / z [H + ]=577.

[0264] Synthesis of compound Q-124:

[0265] Weigh I-11 (0.4 mol) and I-12 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 22 mmol), potassium carbonate (1.2 mol), toluene (2.0 L), ethanol (1.0 L), deionized water (1.0 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound Q-124 with a yield of 67%, m / z [H + ]=709.

[0266] Example 16

[0267] The synthetic route of organic compound Q-150 is as follows:

[0268]

[0269] Synthesis of compound Q-150:

[0270] Weigh I-1 (0.5 mol) and I-28 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound Q-150 by column chromatography with a yield of 69%, m / z [H + ]=658.

[0271] Embodiment 17

[0272] The synthetic route of organic compound R-6 is as follows:

[0273]

[0274] Synthesis of compound R-6:

[0275] Weigh I-29 (0.5 mol) and I-30 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound R-6, the yield is 87%, m / z [H + ]=658.

[0276] Embodiment 18

[0277] The synthetic route of organic compound R-16 is as follows:

[0278]

[0279] Synthesis of compound R-16:

[0280] Weigh I-31 (0.5 mol) and I-2 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound R-16, the yield is 88%, m / z [H + ]=810.

[0281] Embodiment 19

[0282] The synthetic route of organic compound R-27 is as follows:

[0283]

[0284] Synthesis of compound R-27:

[0285] Weigh I-29 (0.5 mol) and I-32 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound R-27, the yield is 91%, m / z [H + ]=658.

[0286] Embodiment 20

[0287] The synthetic route of organic compound R-33 is as follows:

[0288]

[0289] Synthesis of compound R-33:

[0290] Weigh I-29 (0.5 mol) and I-33 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain compound R-33, the yield is 84%, m / z [H + ]=734.

[0291] Embodiment 21

[0292] The synthetic route of organic compound R-52 is as follows:

[0293]

[0294] Synthesis of compound R-52:

[0295] Weigh I-29 (0.5 mol) and I-34 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound R-52, the yield is 92%, m / z [H + ]=664.

[0296] Embodiment 22

[0297] The synthetic route of organic compound R-72 is as follows:

[0298]

[0299] Synthesis of compound R-72:

[0300] Weigh I-29 (0.5 mol) and I-35 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound R-72, the yield is 86%, m / z [H + ]=674.

[0301] Embodiment 23

[0302] The synthetic route of organic compound R-95 is as follows:

[0303]

[0304] Synthesis of compound R-95:

[0305] Weigh I-29 (0.5 mol) and I-36 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound R-95, the yield is 91%, m / z [H + ]=724.

[0306] Embodiment 24

[0307] The synthetic route of organic compound R-121 is as follows:

[0308]

[0309] Synthesis of compound R-121:

[0310] Weigh I-29 (0.5 mol) and I-37 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, column chromatography to obtain compound R-121, the yield is 85%, m / z [H + ]=679.

[0311] Embodiment 25

[0312] The synthetic route of organic compound S-2 is as follows:

[0313]

[0314] Synthesis of compound S-2:

[0315] Weigh I-1 (0.5 mol) and I-38 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound S-2 by column chromatography with a yield of 88%, m / z [H + ]=641.

[0316] Embodiment 26

[0317] The organic compound S-6 route is as follows:

[0318]

[0319] Synthesis of compound S-6:

[0320] Weigh I-1 (0.5 mol) and I-39 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound S-6 by column chromatography with a yield of 56%, m / z [H + ]=717.

[0321] Embodiment 27

[0322] The organic compound S-24 is as follows:

[0323]

[0324] Synthesis of compound S-24:

[0325] Weigh I-1 (0.5 mol) and I-40 (0.5 mol) and place them in a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain compound S-24 by column chromatography with a yield of 81%, m / z [H + ]=717.

[0326] Embodiment 28

[0327] The synthetic route of organic compound S-49 is as follows:

[0328]

[0329] Synthesis of compound S-49:

[0330] Weigh I-29 (0.5 mol) and I-41 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water, dry the organic phase and spin dry, column chromatography to obtain compound S-49, the yield is 83%, m / z [H + ]=657.

[0331] Embodiment 29

[0332] The synthetic route of organic compound S-60 is as follows:

[0333]

[0334] Synthesis of compound S-60:

[0335] Weigh I-29 (0.5 mol) and I-42 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 10 h; after the reaction solution is cooled naturally, wash with water, separate the liquid, dry the organic phase and spin dry it, and obtain compound S-60 by column chromatography with a yield of 89%, m / z [H + ]=733.

[0336] Embodiment 30

[0337] The synthetic route of organic compound S-80 is as follows:

[0338]

[0339] Synthesis of compound S-80:

[0340] Weigh I-29 (0.5 mol) and I-43 (0.5 mol) into a clean three-necked flask, add Pd(PPh3)4 (5%, 25 mmol), potassium carbonate (2.0 mol), toluene (2.5 L), ethanol (1.25 L), deionized water (1.25 L), replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 12 h; after the reaction solution is cooled naturally, wash with water and separate the liquid, dry the organic phase and spin dry it, and obtain organic compound S-80 by column chromatography with a yield of 86%, m / z [H + ]=658.

[0341] Comparative Example

[0342] The present application also provides comparative examples, in which the organic compounds are correspondingly recorded as "comparative compounds REF01, REF02, REF03 and REF04", and the chemical structural formulas are as follows:

[0343]

[0344] Preparation and characterization of OLED devices

[0345] The organic electronic device 100 provided in the embodiment of the present application may be an OLED device, and Figure 1 Taking the preparation of the organic electronic device shown as an example, the preparation method of the OLED device using the organic compound provided in the embodiment of the present application is described in detail below through a specific device embodiment.

[0346] 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, Prime is used as a light-emitting auxiliary material, Host-1 or Host-2 is used as the first host material of the light-emitting layer, Dopant is used as a doping material of the light-emitting layer, 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 compound P-1 of the aforementioned synthesis example is used as the second host material to prepare the corresponding OLED devices. The chemical structures of PD, HT, Prime, Host-1, Host-2, Dopant, ET and Liq are shown below:

[0347]

[0348] The preparation process of the organic electronic device 100 using the above materials is described in detail below through specific embodiments.

[0349] Taking the method for preparing an OLED device using organic compound P-1 as the second host 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:

[0350] Step a: Cleaning of ITO conductive glass substrate (first electrode 11 ): Provide an ITO conductive glass substrate and perform ultrasonic cleaning on the substrate using one or more cleaning agents such as deionized water, acetone, isopropanol or chloroform to improve the work function of the first electrode 11 .

[0351] Step b: forming a hole injection layer 12 on the first electrode 11. The hole injection materials PD and HT are evaporated on the first electrode 11 at a evaporation rate of 3:97, and the hole injection layer 12 with a thickness of 30 nm is obtained.

[0352] 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.

[0353] Step d: forming a light-emitting auxiliary layer 14 on the hole transport layer 13. The luminescence auxiliary material Prime is evaporated on the hole transport layer 13 at an evaporation rate of , to obtain a luminescence auxiliary layer 14 with a thickness of 40 nm.

[0354] Step e: forming a light-emitting layer 15 on the light-emitting auxiliary layer 14. Host-1, organic compound P-1 and Dopant were evaporated on the light-emitting auxiliary layer 14 at a deposition rate of 63:27:10, and the light-emitting layer 15 with a thickness of 40 nm was obtained.

[0355] 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 under 300 mbar to form an electron transport layer 16 with a thickness of 30 nm on the light-emitting layer 15.

[0356] 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.

[0357] Step h: forming a second electrode 18 on the electron injection layer 17. The cathode material Al is evaporated on the electron injection layer 17 at an evaporation rate of to obtain a second electrode 18 with a thickness of 100 nm.

[0358] 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 device.

[0359] In this embodiment, the structure of the prepared OLED-1 device is: ITO / PD:HT(3:97, 30nm) / HT(60nm) / Prime(40nm) / Host-1: organic compound P-1:Dopant(10%, 40nm) / ET:Liq(5:5, 30nm) / Liq(1nm) / Al(100nm).

[0360] Preparation of OLED-2 to OLED-30 devices

[0361] Referring to the preparation method of device OLED-1, the organic compounds synthesized in Examples 2 to 30 were selected as the second host materials of the OLED device, and OLED-2 to OLED-30 devices were prepared accordingly. It can be understood that in the preparation methods of the above OLED-1 to OLED-30 devices, except for the different host materials, other functional layers and experimental conditions are the same.

[0362] Further, referring to the preparation method of the device embodiment, comparative compounds REF01 to REF04 were used as the second host material to prepare comparative example OLED-REF01 to OLED-REF04 devices. Compared with the preparation method of OLED-1 device, the preparation methods of OLED-REF01 to OLED-REF04 devices are the same except for the host materials.

[0363] In this application, the current-voltage (JV) characteristics of OLED-1 to OLED-30, OLED-REF01 to OLED-REF04 devices were characterized, and important parameters such as luminous efficiency and lifetime were recorded, as shown in Table 1. The voltage and luminous efficiency are calculated at a current density of 10 mA / cm 2 The lifespan (LT95) is measured at a current density of 50 mA / cm 2 The time taken for the device brightness to drop from the initial 1knit to 95% under the condition of .

[0364] Table 1

[0365]

[0366]

[0367] It can be seen from the results in Table 1 that when the organic compounds provided in Examples 1 to 30 of the present application are used as the second host material, the voltage, luminous efficiency and life of the OLED device prepared by combining with Host-1 or Host-2 show excellent effects. This is because when the disclosed first host material Host-1 or Host-2 is combined with the organic compound provided in the examples of the present application, the energy transfer from the host to the dopant is better achieved compared with the combination used in the comparative example. Therefore, when Host-1 or Host-2 is used in combination with the compounds of the present application and used as a host for the green light emitting layer by co-evaporation, the driving voltage, luminous efficiency and life of the organic light emitting device can be improved.

[0368] In addition, an embodiment of the present application further provides a display panel, which includes the organic electronic device described in the above embodiment.

[0369] In summary, the embodiment of the present application provides an organic compound whose molecular structure is composed of a plurality of electron-rich conjugated planar rigid groups, such as nitrogen heterocycles, oxygen / sulfur heteroatom fluorene rings, so that the organic compound has sufficiently strong electron transport and stability. When the organic compound is used in a light-emitting layer in combination with a hole transport type host material, it can achieve effective transmission of excited state energy, which is beneficial to improving the luminous efficiency and life of the organic electroluminescent device. In addition, when Z 1 , Z 2 and Z 3 When selected from N, the nitrogen heterocycle is directly connected to the No. 4 position of the dibenzoheterocycle, and is extended from the No. 1 position of the dibenzoheterocycle to connect to the second dibenzoheterocycle. The double substitution of the above-mentioned positions makes the molecular conformation of the organic compound more compact, and the dihedral angle between the plane of the nitrogen heterocycle and the plane of the dibenzoheterocycle is reduced, so that the corresponding LUMO energy level orbital distribution area is more planar, thereby further improving the electron transport performance and chemical structure stability of the organic compound; therefore, the luminous efficiency and service life of the organic electronic device using the organic compound of the present application can be improved.

[0370] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, the meaning of "plurality" is two or more, unless otherwise clearly and specifically defined.

[0371] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0372] The embodiments, implementation methods and related technical features of the present application can be combined and replaced with each other without conflict.

[0373] The above are only preferred embodiments of the present application and do not constitute any form of limitation to the present application. However, any simple modifications, equivalent changes and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application are still within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that The chemical structural formula of the organic compound is shown in general formula (1): Among them, X 1 Selected from O or S; X 2 Selected from O, S or NR 3 ; Z 1 , Z 2 and Z 3 is selected from CH or N, and Z 1 , Z 2 and Z 3 At least one of is selected from N; Ar 1 and Ar 2 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 4 to 20 carbon atoms; R 1 is selected from hydrogen or deuterium; R 2 is selected from hydrogen, deuterium, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 4 to 20 carbon atoms; R 3 is selected from substituted or unsubstituted aromatic groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 18 carbon atoms; m is selected from any integer from 1 to 6; n is any integer selected from 1 to 7.

2. The organic compound according to claim 1, characterized in that Z 1 , Z 2 and Z 3 Selected from N.

3. The organic compound according to claim 1 or 2, characterized in that Ar 1 and Ar 2 At least one selected from the group consisting of phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl and phenanthrinyl.

4. The organic compound according to claim 1 or 2, characterized in that R 2 At least one selected from the group consisting of hydrogen, deuterium, phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, and phenanthrinyl.

5. The organic compound according to claim 1 or 2, characterized in that R 3 At least one selected from phenyl, biphenyl, deuterated phenyl, and pyridyl.

6. The organic compound according to claim 1 or 2, characterized in that The organic compound is selected from any one of the following compounds represented by formula (P-1) to formula (P-160), compounds represented by formula (Q-1) to formula (Q-160), compounds represented by formula (R-1) to formula (R-128), and compounds represented by formula (S-1) to formula (S-100):

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

8. 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 6, or the composition comprises at least one organic solvent and the mixture according to claim 7.

9. An organic electronic device, characterized in that: The organic electronic device comprises: 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, wherein the material of the organic functional layer includes at least one organic compound as described in any one of claims 1 to 6, or the material of the organic functional layer includes the mixture as described in claim 7, or the organic functional layer is made of the composition as described in claim 8.

10. The organic electronic device according to claim 9, characterized in that: The organic functional layer includes a light-emitting layer, and a material of the light-emitting layer includes a first host material and a guest material, wherein the first host material includes at least one of the organic compounds.

11. The organic electronic device according to claim 10, characterized in that: The material of the light-emitting layer further includes a second host material, the second host material includes a hole transport type host material, and the HOMO energy level of the second host material ranges from -5.2 eV to -5.5 eV.

12. A display panel, characterized in that: The display panel comprises the organic electronic device according to any one of claims 9 to 11.

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